EP 101: Andrew Bialecki (CEO, Klaviyo) on Building a $6B Software Company - Klaviyo’s Uncharted Path

Before Andrew Bialecki took Klaviyo public and scaled the company to $6B, he bootstrapped it to over $1M in ARR. In our discussion, Andrew reveals his philosophies around fundraising, finding the best talent, cultivating entrepreneurship inside Klaviyo, scaling culture, and more. (00:00) Intro (01:13) Klaviyo's Bootstrap Beginnings (09:37) The Strategic Pivot to E-commerce and Retail (15:02) Narrow Focus as a Catalyst for Growth (25:48) Building a Culture of Learning and Growth (34:02) The Entrepreneurial Path: From Engineer to Founder (37:09) The Commute to Innovation: A Startup Journey (37:57) From Performable to HubSpot: A Tale of Acquisition and Growth (39:26) Building Klaviyo: Lessons in Entrepreneurship and Team Building (40:40) Scaling a Startup: The Challenges of Leadership and Hiring (47:04) Fostering a Culture of Experimentation and Entrepreneurship (53:15) The Art of Hiring: Identifying Entrepreneurial Spirit (58:39) Chronological Resumes and the Power of Storytelling in Interviews (01:06:16) Embracing the Unsexy: The Philosophy of 'Eating Your Vegetables' (01:13:33) Klaviyo University: Training Future Founders and Leaders (01:15:25) Cultivating a Culture of Learning at Klaviyo (01:16:17) The Genesis of Klaviyo University (01:17:05) Core Curriculum and Electives: A Deep Dive (01:20:46) Adapting Learning Programs in a Remote World (01:21:56) The Art and Science of Effective Business Writing (01:28:35) Recruitment and Onboarding: Strategies for Success (01:38:05) Building and Sustaining Company Culture (01:41:28) Leveraging Boston's Ecosystem for Growth (01:47:06) The Future of Software: Productivity vs. Output (01:52:33) Closing Thoughts and Acknowledgements Executive Producer: Rashad Assir Producer: Leah Clapper Mixing and editing: Justin Hrabovsky Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow 📱 X - https://twitter.com/loganbartshow 🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow About the Show Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member. Tap follow and enable notifications to stay ahead of the game.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:04Logan Bartlett?

  Welcome to the Logan Bartlett Show. On this episode, what you're going to hear is a conversation I have with CEO and co-founder of Klaviyo, Andrew Byelucki. We talk about a number of different things over the course of this conversation, including building an entrepreneurial mindset among your employees, why there's magic in obsessing over details, why culture is a product that you actually ship, as well as his philosophy on fundraising, which included nearly bootstrapping the business for a while before raising significant outside capital. Klaviyo has grown into a $6 billion-plus public business. Andrew has a number of different lessons that are helpful to any entrepreneur or operator that you'll hear now.

• 0:42Logan Bartlett?

  Andrew, thanks for doing this.

• 0:43Speaker 02

  Yeah.

• 0:44Logan Bartlett?

  So I want to start off talking about the benefits of constraint. And I think either by your own decisions, or maybe initially the venture capital ecosystems decisions, there were constraints that you either chose or were forced on you. And I think, I think that, that those constraints, it sounds like benefited you guys in a number of different ways, maybe related to focus. But how do you think about constraints and like the advantages around them and how it's benefited you guys in your journey?

• 1:17Speaker 02

  Yeah. So, well, first, I mean, what constraints were kind of like born through constraint? So, you know, Klaviyo was a bootstrap business.

• 1:27Speaker 02

  We, we founded the business in 2012. I remember quit my job, you know, cornered my then was going to be co-founder Ed. He was at business school and said, hey, like, let's start working on things. We start working on things while he was graduating from business school.

• 1:41Logan Bartlett?

  And then it was-

• 1:42Logan Bartlett?

  Which probably wasn't doing much anyway at that point.

• 1:44Speaker 02

  Well, I had a hot, so one of my, he can advocate for an MBA, but I'm a very big believer that MBAs are a waste of money. Like, just go work at a startup. Like, you'll get paid, so you hopefully can save up a little bit. Don't have to take on the loans and the debt, and you'll learn just as much, right? And I'm a huge reader, so I kind of feel like if you want to read the case studies or the business books, like, you can, you can do that in your spare time.

• 2:11Speaker 02

  But anyways, yes, we started in 2012, and we didn't raise any venture capital until, you know, we were already profitable. And I think it was 2015, 2016. So we're kind of born out of constraint. And before I hit on that, like a lot of people ask like, well, gosh, why didn't you do that? And there are really like two reasons. The the kind of, you know, the the one was, you know, and I had both come from families with small business backgrounds. And I always felt it was kind of weird that technology companies were the one companies where it's like, yeah, it's okay to just be a cash incinerator.

• 2:46Logan Bartlett?

  Yeah.

• 2:47Speaker 02

  But every other business is like, no, you have to turn a profit. You know, maybe not day one, but you can't wait that long. So and especially, you know, the marginal cost of building software. I mean, it's like, you know, we had, there was cloud compute and AWS was a thing at that point. Like, it just was way easier than it was in the 2000s. So that was one is like, we felt it was possible. And the second one was, so I mentioned, you know, Ed was at business school. He was at, he was in MIT. And, you know, all the, a bunch of the, you know, private equity venture capital groups would do these kind of summer at X. And so they have these programs where they give you $20,000 for the summer. And you had to put together a little pitch video and, you know, they just give you like, kind of like, you know, they give you a no equity funding and, you know, a place to work. And we thought that was awesome.

• 3:32Speaker 02

  It was $20,000. I got to get some fun for the next year with that. We applied to like three or four of those and got into none of them. Despite the fact we're like, we have a product, we have customers. And, you know, so I remember telling Ed, I was, if we went and tried to pitch, you know, the actual like, you know, VC fund, we're like, gosh, Ed, we're like batting zero. You know, I mean, I mean, maybe we're just not there yet. So anyways, he kind of took it as like, all right, we're going to figure out how to make this work with just the two of us.

• 3:56Logan Bartlett?

  What in retrospect, what was, was the articulation not fully?

• 4:01Speaker 02

  I think so. Yeah. I mean, we had this, so we had this point of view that we were just going to obsess about products. You know, my background was in software and a little bit in product design. And Ed was in product design. And we said, like, look, we're going to obsess about building product. We thought we were really good at that. And we were just gonna, we both believed in, you know, lean startup was a thing at the time. And so it was getting close to customers and we're going to find real revenue. And so, yeah, we just put like no time into, you know, the pitch, pitch decks. And, yeah, I thought it was funny because, you know, folks be like, well, I don't really get it. I'm like, well, here, I've got like, got like 20 customers, you know, paying us, I don't know, a thousand bucks, like. I mean, there's, there's, there's something here, but what we just didn't, we didn't invest in that part of it.

• 4:45Logan Bartlett?

  Yeah.

• 4:46Speaker 02

  It wasn't actually until we did some more formal, you know, fundraising that was like, okay, we probably should like clean this up. The actual pitch.

• 4:52Logan Bartlett?

  So some of the constraints were forced on you, or at least you were guided towards the.

• 4:57Speaker 02

  We like to, you know, the, the, the rosy picture was, you know, well, we're going to do this because this is the right way to build a business. And then there's this other side of like, okay, well, maybe there are, maybe there are no other capital sources. So we just got to figure it out.

• 5:07Logan Bartlett?

  And you were technical by background and most of the, at least the, the biggest costs of starting tech companies are usually hiring developers to go do it. So you could, you could do it yourself and execute on that.

• 5:18Speaker 02

  Yeah. Another, another thing I advise, uh, you know, founders are, I tell folks is like, it's like, look, if you are a non-technical founder, then you should go find a technical co-founder.

• 5:27Logan Bartlett?

  Yeah.

• 5:29Speaker 02

  If you are, you know, two or three technical co-founders, raise as little capital as you need. You know, one of the good things, it's not really a constraint thing, but we've had this rule inside of Klaviyo that we don't celebrate fundraises.

• 5:43Speaker 02

  So, you know, other than our, other than our IPO, which, you know, we're like, yeah, we'll have a party for that, but otherwise we're like, well, it becomes kind of a vanity metric. It's like, well, nobody really cares and it's, you know, it makes you feel good because that's a little bit of validation.

• 5:57Speaker 02

  But we had this point of view that it's like, you know, we're just not, we're not going to, we're not going to focus on that.

• 6:01Logan Bartlett?

  Yeah. No one celebrates, uh, taking out mortgages on your house. I don't think.

• 6:06Speaker 02

  Exactly. Same mentality.

• 6:07Logan Bartlett?

  Yeah. It's sort of like you're, you're giving up. I mean, there, there's, there's elements to be celebrated that there was outside independent validation. And, you know, your parents say congrats or whatever. Your, your, your spouses think that you can stay employed for longer. But it's not inherently in and of itself, a point of validation on the actual terminal value that you're going to create.

• 6:29Speaker 02

  That's right. That's right. That's right. So anyways, back to constraint. So when we started, you know, one of the great viral loops in any product company, uh, technology, software company.

• 6:42Speaker 02

  We always felt like there was, there was, you know, there's kind of building and there was selling and we used selling as like, really like just working with customers, right? Doing the, you know, okay, well, what do you think of what we built? How could it be better? Getting them to adopt it, like figuring out that kind of, there's a real great flywheel back and forth between those two. So I'll give you like, there were a bunch of great patterns that we developed and then carried forward. Like for instance, one was, um, we had this shared, you know, um, email inbox that we used to do support. So after we got a couple dozen customers, you get questions, you know, every day, every week. And we had this rule that every morning we'd wake up and we weren't allowed to work on anything else until we'd like cleared that inbox.

• 7:23Speaker 02

  So, you know, that was especially interesting as we got to, okay, now you've got a dozen, now you've got a couple dozen. You know, when something broke, you heard about it. If something was hard to do, you heard about it. And, you know, for me, a lot of my days were, all right, I mean, solve for that stuff in the morning and then I'm going to go code and build the next, you know, the next stuff in the afternoon, right, in the evening. And if a lot of my day was sucked up by responding to these questions, I was like, okay, well, the first thing I'm going to go fix is whatever those problems were. That created a lot of great discipline about building good products that it's interesting, like as we've grown, we've had to work hard to kind of keep that loop tight because it's natural that, you know, if you, if you split up into, okay, well, I have a support, support

• 8:06Speaker 02

  team or a customer success team and I have a product engineering team, it's easy for there to become this like kind of like, you know, buffer zone, right? And then those things just don't get resolved as quickly and the product actually suffers for it. So we think a lot of the reason we were able to go so fast was because that loop was super tight with us because it just, it had to be.

• 8:23Logan Bartlett?

  There's the cultural principles of that, which you've tried to maintain and we'll go into, I definitely want to ask questions about like how you maintain that over time and as you scale and when you get to hundreds of people and hundreds of millions of revenue and all that stuff, which I think is interesting. But then there's the, there's, there's a very counterintuitive element about what, what focus breeds in that. And so like finding your end market as potentially an accelerant to what you've done or limiting headcount. And so there was less silos of communication, which is partially tied to what you just said, but maybe a little distinct as well. Can you talk a little bit about that?

• 9:07Speaker 02

  Sure. Yeah. So, you know, I mentioned that, you know, my background is like building products and the idea for Klaviyo, when we started and still is today is I think the future of the way that businesses and consumers interact with each other, you know, I grew up in the, you know, the 90s. And I remember when it's like, if you wanted to go deposit a check, like you went to a bank teller and there was a person you had to give it to. You couldn't deposit an ATM, you could take a picture on your phone. If you wanted to change something about, you know, if you wanted to add HBO to your cable bill, you had to call somebody. That wasn't something you could just do yourself. So everything was, the idea was if you're a consumer of some service, you have to call somebody, you have to interact with a person.

• 9:47Speaker 02

  Okay, but our belief is that is, you know, the old school, it's going to be anachronistic. Everything is going to be mediated by software. And so then the question is, is like, okay, well, how do you build software that can be the, you know, automated version, the scalable version of a business or of a person? So like to think like whether you're a solo entrepreneur or your business, there's kind of this, this, you have this brand, this way you want to interact with the world. And we look at Klaviyo as that kind of surrogate that makes you infinitely scalable, right? We talk about being yourself at internet scale. So we're that scalable brain for business, that scalable voice. So that was the concept behind Klaviyo. So when we built it out, it was, it was very abstract. We actually started, you know, we wanted to sell to other startups.

• 10:32Speaker 02

  So we did what every good startup did back in the 2010s. And we posted on Hacker News and tried to get a bunch of startups to use us. Once we had the product going, the next question was like, well, where are the, where's the demand going to come from? Where are the customers going to come from? And we looked at it as like, well, there's tons of businesses that could use us. We just have to figure out where the right pockets are. So it's interesting, the startup thing worked okay, but we found that there were a lot of, a lot of software businesses that didn't really know, you know, how their customers were even supposed to use their software. So there's a lot of consulting we had to do and it was very slow.

• 11:03Speaker 02

  Would that have been more B2B in that regard? Yeah, exactly. Yeah. Yeah, I mean, we're kind of selling to businesses like us. You think of like the normal onboarding flow, somebody signs up, you say, all right, so what are the actions that make this person successful with your, you know, with your software? And we, you'd go talk to a bunch of founders or teams and they're like, well, that's a really good question. We have to figure that out. Can you guys answer that for us? And you're like, oh, okay, gosh, like you guys haven't, you haven't solved this problem yet.

• 11:25Speaker 02

  Then a friend of mine had a Had an e-commerce business and he started around the same time as us. And of all things, he was, he was, he was creating T-shirt quilts on the internet. So you'd send like, you'd literally collect like old T-shirts, right? Say from high school or college or, you know, activities you're part of. And they would collect them for you and turn them into like a blanket, right? Into a quilt. And so he's like, yeah, well, I'm on this, this platform Shopify like, and I was like, okay. Well, like, do you think this is like relevant too? I mean, you've got all these, it's pretty customized products. And they had a lot of repeat purchases, right? Like, you know, you end up with like a parent that would buy for their kids as they graduated college and all this kind of stuff. And he's like, yeah, totally.

• 12:10Speaker 02

  And so we started there, there was another business, you know, so that was one business. We found a couple of other ones in around the Boston area where we was, where we founded Klaviyo. And they all had the same thing. And so our goal the whole time though was how do we get like scalable demand? So after we kind of hustled for those first 10, maybe in retail and e-commerce.

• 12:32Speaker 02

  We had this idea that was, gosh, we need to find a way to get people to come to us. And we don't have a lot of, you know, dollars to spend on advertising. And so we had this idea that, well, gosh, there's, you know, SaaS is kind of becoming the thing. People were shifting away from open source and hosting, self-hosting to software as a service where they have to set up the software. We said, well, why don't we just go build partnerships with those platforms? Like, what if we say, hey, look, we kind of complement your software and, you know, we kind of, we complete this picture. Maybe that could give us a way to get, you know, at the time for us, it would have been like hundreds of businesses to come to us, um, you know, in a week or in a month. And then at that point, I was like, okay, if we have enough customers, we can keep, go back to working on the product and kind of expanding it. And that strategy worked great.

• 13:14Speaker 02

  Cause what we initially built was, you know, almost like we built, you know, uh, this database and marketing software. But you had to connect all your data through these APIs. And we said, what if we just go partner with those platforms? We build all these connectors, kind of build once, run, you know, hundreds of thousands of times. And that strategy worked great for driving demand. And so that's one of the ones where, you know, I think a lot of, let's say, software companies. A lot of them still, you know, it's either it's either just find the call list and go start calling down, you know, start calling folks or it's do advertising. And I think we thought a little more creatively about it, really about this idea of partnerships and how you could use those to do, you know, awareness and demand gen.

• 13:57Speaker 02

  And it turned out to be really scalable and also really efficient. That's one of, you know, the first kind of little S curves that, you know, we took off.

• 14:05Logan Bartlett?

  And so that took you into e-commerce and retail as kind of an end market. And at that point in time, so now you're building distribution, but you're opting into these partnerships that service a narrower subsegment of the overall economy. Your tool's broadly applicable, but now, and so then you're facing the decision, I assume of like, do we tailor our website copy? Do we tailor the product considerations a bit more to that? And so maybe, maybe talk through that decision tree of like, okay, well, we have this tool that could be broadly applicable and we're actually narrowing our end market in some ways.

• 14:42Speaker 02

  Yeah, yeah, I remember it was, I would, uh, fights, probably too big of a word, big, big debates. My co-founder and I had where I remember our homepage, I had, we very intentionally designed it to be very generic. Right. Klaviyo were the brain for your business, you know, store everything you know about your customers. And then like, you know, treat them the right way, message them at the right time. And importantly, it didn't have any of these things of like, oh, there's nothing for e-commerce or retail on there. But we were starting to get this growing swell of e-commerce businesses that were coming to us. And we had these great quotes from customers like, uh, you know, I remember there was a, a backpack company that said, oh, you know, other softwares for open clicks, Klaviyo's for sales.

• 15:26Speaker 02

  And it was like, oh, great. It's like the best tag. We just put that on the website.

• 15:29Logan Bartlett?

  Which is great about e-commerce is like, there's actual Tardor or Y that you've been tied to.

• 15:34Speaker 02

  It's a very direct response.

• 15:35Logan Bartlett?

  It's not B2B sales where it's like, yeah, we got, you know, 5% better leads coming in.

• 15:40Speaker 02

  I agree. Yes. Yeah, yeah, totally right. Right. The conversion cycle is very quick. Totally. So I remember Ed and I give him all the credit for this. You know, kind of, came to you one day, we used to have these like, you know, these like, I guess, I don't know, weekly roundup staff meetings when there were like three of us. But it was like, it was like the two of us, we'd sit and we'd have a beer and pizza at the end of the day, at the end of the week on a Friday. And he's like, look, Andrew, I really think we should, you know, I think we should change the website and really focus on this vertical. We're getting a lot of traction there. We'll just go faster. I know how much you care about going broad, but like, we can go do this and then, you know, make it more horizontal. And I remember going home and thinking about it for the weekend and being like, you know, kind of grumble, I really don't want to do this, but he was totally right.

• 16:24Speaker 02

  And so we did it. We did it the next week and it was 100% the right decision. And yeah, I think, you know, we had not done a ton of market sizing at that point. I mean, we knew it was a big market. Cause we'd studied some of our competitors and like where their, you know, who their customers were. So it was plenty big enough to say, get us to, you know, 100 million in run rate.

• 16:46Speaker 02

  But I think, you know, we've been, you know, as we've studied it more now, it's, I mean, it's obviously a growing segment. But retail is just such a huge part of the economy. And, and we also realized how underserved it was. So going vertical really helped. The other thing that really, I mean, I, part of what Ed, you know, pitched me on and part of it is I thought this was a great idea. Was if you looked at our competitors at the time, whether they were kind of the traditional newsletter type companies or, you know, some of the bigger B2B SaaS companies had their kind of marketing clouds, marketing suites.

• 17:20Logan Bartlett?

  The MailChimp on one side and Salesforce Marketing Cloud.

• 17:23Speaker 02

  Right. So they're all like, and they're all very horizontal. And we did think there was some kind of arbitrage of, you know, we were all about, okay, we're going to do more personalization, more targeting. We're going to be more focused on conversions and return. And you kind of do want to go like vertical by vertical, use case by use case for what does that mean for you? And we felt like there was some arbitrage of, okay, they're going very wide. If we focus in one area, we can kind of, you know, go win that market. And then we can take that playbook and do it for others. And in fact, that's, you know, we've got a whole team internally. That that's what they're doing is they're basically standing up effectively, you know, industry by industry. So. I tend to think that like, you know, when you, when you, when you, when you pick which markets you're going after.

• 18:09Speaker 02

  I think generally speaking, you should try to build a product that is horizontal. I mean, there's obviously a lot of judgment there in how wide you go, but something that's a little more abstract, but you have a lot of degrees of freedom on the, you know, marketing and go to market side. And I think you have to choose whether you're going to go horizontal, which can work if it's kind of a newer category. It's a little bit of like, hey, everybody needs this and there's, you know, potential for lots of, lots of demand. Or you can go kind of vertical by vertical. And either, either way, I think, once you get to scale, you end up with this, you have some sort of, you know, horizontal product marketing and then an overlay on top of that, that's kind of like, okay, use case by use case, industry by industry. So you can get to it in two different ways. And I think in our case, I think one of the really smart things was, we're like, well,

• 18:52Speaker 02

  because everybody else has gone broad, if we focus more, you know, vertical by vertical, that will stand out relative to them. That'll give us a little bit of a competitive advantage.

• 19:02Logan Bartlett?

  More resonance with the end customer?

• 19:03Speaker 02

  Yeah.

• 19:04Logan Bartlett?

  And I guess, I don't want to speak for you, but I would guess that had venture capital been raised or a meaningful part of, of, you know, the underlying business consideration, both the distribution of how you were thinking about going through partners and then also the narrowing of the TAM, I assume you might not make those two decisions on the same tree. It's like, okay, we're gonna, you're, you're gonna control less of your own destiny from a accelerating growth standpoint and we're going to narrow the TAM that you're going to target. And so both those decisions, I maybe would have come at odds with venture capital.

• 19:45Speaker 02

  So I'd say like, yeah, I'd be two things. One, uh, you know, it's hard to start a company. It's hard to start a company and, because there's so many decisions you have to make, right? And it's, uh, and, you know, and I think there's a lot, you know, everybody starts out in mirrors, like, you don't always have 100% confidence that you're going to be right about those, right? So one pattern I've seen from some entrepreneurs, founders is they sort of want some help making those decisions and I think they can overfit to their investors, right? Because investors, I mean, really great ones are great advisors. We've had some excellent ones. We had very good, say, investor or founder fits with our seed investors.

• 20:25Speaker 02

  But yeah, I think that's right because I think there's, generally speaking, a lot of venture capital investors would say like, well, look, bigger than better. So don't narrow things if you don't have to. And that might be right. It's just there's some nuance to it. And I think people want helping decisions. So sometimes you kind of have to have your own point of view and not wait for other people to tell you what the right answer is.

• 20:48Speaker 02

  What was good for us on that front is actually our seed investors had a bit of a contrarian view on that, which was, hey, I actually think there's room to start going, you know, kind of vertical by vertical and that you can build a big business that way. This concept of vertical SaaS was like, you know, say newer 10 years ago. And I think that was very much our benefit because like we were actually very much like on the same page.

• 21:14Speaker 02

  The other thing I'll say is I, you know, I, in the last 10, 15 years, there's been a lot of software companies that I feel like have, you know, they've, they've kind of, their ambition has gotten smaller. There's been a lot of like unnecessary niche-ification of, well, I'm going to go after this one little thing and that's going to be my pocket. It's a fine place to start, but I do think you need to have the broader ambition of, okay, well, how is this going to scale out? Like, I'll give you one example that was relevant to us and our product. You know, when we built Klaviyo, this notion of like conversions, like what happens after you run a marketing campaign? Well, what was interesting was we saw a lot of other companies that even tried to do something similar to us, but they really overfit to this idea that like a conversion meant like a retail transaction.

• 21:58Speaker 02

  And that was the only thing that it would ever matter. And we were actually able to take a lot of market share from those folks because they had so pinned themselves to this idea that the only thing that matters is this conversion event. Right. And what we found from retailers is they're like, well, sometimes it's like getting somebody to sign up for a loyalty program that matters. Or sometimes, you know, we're seeing increasing a lot of retailers where retail is one part of the business, but they also offer services. And so keeping that more abstract in generic made a big difference to us. So I think there's also like a little bit of, you have to know the game plan, right? Is the game plan to start vertical and then go broad or is the game plan just to be vertical?

• 22:39Speaker 02

  And in that case, I actually think like for us, we, you know, we, we knew that it's like, okay, we're going to start here, but that will never be the end goal. Right. So the ambition is still big. So that's the other thing I kind of look for in companies is do they have this greater purpose? Is this like a stepping stone? It's like part A of this like greater master plan or is that like the whole thing?

• 22:57Logan Bartlett?

  Yeah. And I guess at the time you were getting going too, it was a lot of, I mean, there's the Jim Barksdale quote of, you know, bundling and unbundling. And but, but at that point in time, there was a lot of best of breed niche functionality. And now it's probably come a little bit more in vogue. I think Parker Comrade started the compound startup as like the, the adage around it. But being broader in your ambitions rather than we'll let us take the ATS part of the market and someone else will take the, you know, the LMS side of it or whatever. All those different things that I think you guys have done a great job. HubSpot has built out like a lot of these different modulators within a broader suite.

• 23:38Speaker 02

  Yeah.

• 23:39Logan Bartlett?

  I think what do they, I mean, this is a total separate thread on this, but it is interesting when I get asked the question. I'm sure, sure you do as well, but like the, the, someone 22, 23, 24, five has the question of like career advice, right? And. And it's counterintuitive to tell them to be like, no, no, no, limit your options. I'll get a lot of ex bankers or consultants or whatever. And they're like, how do I get a job in investing? And I'm like, the best way to get a job in investing is pick the most narrow part of investing and go as deep as you possibly can in it. Because it's really hard for people to want to do this because they feel like they're limiting themselves from the optionality of, well, I don't know if I want to do private

• 24:23Logan Bartlett?

  equity or hedge fund or like early stage venture or late stage venture. If I want to be a biotech investor or whatever, all of those things sound potentially interesting because I want to get into investing. But the problem is when you interview for any of those jobs, you're an inch deep in a mile wide in your competency. And so you don't, you don't give people the narrowness of, oh, well, I just talked to a guy who was thinking about biotech investing. He was really good at this. And that was actually a fortunate thing in my career is like I, early on, I was like, I want to do software and I want to do software, series B investing. And I was so specific in it. And then you learn all the little loops about it. So by the time you're actually qualified to interview for it, you're so much better equipped to have a conversation with someone about it.

• 25:08Logan Bartlett?

  And I think it's, it's true of startups as well, that like narrowness actually is the answer, at least initially, right? And then gives you the opportunity to kind of build those certain concentric loops around it.

• 25:18Speaker 02

  Definitely, yeah. So I would say, one, I think five year plans are underrated. People should have those. Two is, yes, going deep matters and actually like in learning as kind of a meta skill and being good at that, acquiring new, you know, knowledge about things matters. So maybe just to comment on each of those. So first, my dad was a big five year plan guy. He said, sure, I don't think they ever shared his five year plan with me, but he was always a, you know, think, think longer term. And it sounds a little contrarian to the whole, you know, kind of move fast startups, like experiments a lot. But I do think in general, people should think further out of like, well, where do you want to be in a few years? And it, you don't necessarily have one goal.

• 26:02Speaker 02

  You could have like, well, there's a couple thing candidates and you know, you don't have to stick to them. You can change them, you know, in six months or a year. But thinking forward and then working backwards is like a real thing.

• 26:14Speaker 02

  You know, when I got out of school, You know, I was a physics major and I had taken a couple CS classes, but didn't have a programming degree and wanted, joined a software company and was like, okay, my, my kind of goal over the next few years is I want to be an amazing software engineer and I need to figure out what that means and get good at those skills. And so that was the goal, right? And then when we, when I started to think about startups, I was like, okay, well, our, you know, we're going to build a sustainable startup. That's the goal. And for us, that meant, you know, profitable, you know, and, you know, I was going to use the fact that I was a really good engineer as like, okay, that's going to be my, my one kind of like, that's my niche that's going to like help power towards that. So I think five year plans,

• 26:58Speaker 02

  you know, three, five year, like having a point of view on that is underrated. More people should step back and think about where do you want to be? And then on like the going deep in places. Yeah. I mean, when I started, the first company I worked at was this big, you know, what we now call machine learning and AI, we used to call it very unsexy, like we called data mining. So it's got a, it's got a brand overhaul, but like we were doing ML and AI with these big Fortune 500 banks, retailers. Okay. So there was a lot of really smart folks in the data side, but nobody knew anything about UI and UX. Well, I got lucky. I happened to report to the woman that was kind of the UI person. And this was all very early web software days, right? Versus there's no Chrome.

• 27:39Speaker 02

  There was barely Firefox, you know, we were selling, it was all Internet Explorer. Well, I just decided I was like, okay, I'm going to become great at, you know, designing for the web. Well, in early 2000s, that turned out to be a great idea because that would become like the next decade's worth of stuff. So I obsessed about that and became like the expert at the company.

• 27:58Logan Bartlett?

  Did you see that trend or was it like, hey, you know, I'm going to try to?

• 28:04Speaker 02

  Yeah, it felt like it. I mean, more and more things were coming out where it was, okay, you know, I mean, the company I was at, I think it moved away from Java applets to, you know, okay, we're going to deliver our software through a browser. And it was enormously painful to develop for, you know, and it's actually, and yeah, it seemed like, and there was a lot of momentum, you know, big companies, like I remember, you know, Yahoo at the time was really invested. And you know, UI and how to design for the, you know, for the web. And I remember I would go to like these early, really early days, like JavaScript conferences with like, you know, it was like John Rezig, who created jQuery, which nobody knows who that is. Like the founders of GitHub were there because this was like a big part of their ecosystem.

• 28:47Speaker 02

  You know, the folks that ran like the Facebook front end. So it was a very small, like, you know, 40, 50 people. And this is like, yeah, we're just all nerding out on this tech. So I think trying to pick those pieces of technology that you think are going to go forward is a really good idea. And then, yeah, I mean, like you get good at that. And I think there's this, this gets this meta skill of learning. I think really good entrepreneurs, founders, you know, just you gotta be, or frankly, everybody, you gotta be really curious. So we talk about at Klaviyo, we like people that are fat T-shaped. So you know how people talk about T-shaped? Hey, I go really deep in an area, then I kind of go a little bit in everything else. We say that's good, but ultimately, you know, if you can have like a couple of areas where you go really deep,

• 29:31Speaker 02

  you know, it's the intersection, intersection between those things, the overlap. I mean, that's what makes you even better. There's really access multiplier. So yeah, I love this idea of go deep somewhere, become the expert at something, and then start to add up a couple of those areas. And then that you can then parlay into like the next thing. And that, you know, for me was, okay, well, how do I get to be a good engineer? I'm going to get good at like, you know, building for the web. I'll also learn how to do the backend parts. Now I want to start a startup. Great. I feel like I've got the products and the engineering part locked down. And then I would just corner people about, okay, well, how do you do the sales and marketing side? How do you drive demand? What does it mean to run a sales team? And you start to just aggregate more and more of these skills. And then, you know, once you've kind of reached that next stone, we have this saying internally inside of Klaviyo, you know, we're always 1% done.

• 30:15Speaker 02

  Every time you have a little bit of success, it's like, great, now you gotta move the goalpost further out. So that there's like a, you know, a bigger thing to aim at.

• 30:23Logan Bartlett?

  In that pursuit, so went to go work at APT, sold MasterCard for 600 million bucks. Were you there when they sold or was that after?

• 30:32Speaker 02

  No, but I'll tell you like the, so another thing is, you know, for folks that are, you know, in their early twenties just graduating school, like I think if you've got an idea and you want to go pursue a great, but if you don't, I think joining great companies is a great idea. That, you know, this company I worked at, Applied Purge Technologies.

• 30:47Logan Bartlett?

  Which is like the most generic boring name.

• 30:50Speaker 02

  It's a mouthful. It was a very fun fact. We tried to get APT.com. It turned out like, the only thing we could get, it was APT7. The other numbers were already, so very fun company, but really super well-run.

• 31:02Logan Bartlett?

  Do you remember how you even found it?

• 31:04Speaker 02

  Yeah, I mean, so they were, one of the things that I took from them is they were very big into campus recruiting, something that we've carried forward. They would just get, they were, they had a policy of they were almost exclusively going to hire from campus and then they were going to grow folks up. It's become a little bit, that's another thing that I have a very strong perspective on is in general, you should prefer to hire folks that are either early in career or out of school and then really build a program where they can grow up there. If you look at a lot of the all-time great companies, that's how they, that's how they have built culture.

• 31:36Logan Bartlett?

  And why do you think that's the case? Is it just that like that's the, you're pulling from the broadest pool of talent and you get to refine that within your own, you know, vision?

• 31:47Speaker 02

  I think there's, I mean, you know, look, recruiting is hard, right?

• 31:50Logan Bartlett?

  Yes.

• 31:50Speaker 02

  You know, we all know that. I think everybody in their heart of hearts is like, I want to hire the person that knows how to do the thing and then I'm going to hire them and I'm just going to leave them alone and I never have to talk to them and it's great because they're just going to figure everything out themselves. That is just practically not possible.

• 32:05Logan Bartlett?

  Yeah.

• 32:06Speaker 02

  So I think if, once you make the decision that you're like, okay, well, there's a way that we want to work and it's not inflexible. I mean, you can obviously, you could, you could work as a team to redefine it over time, but there's a way that we want to work, you know, and let's call that culture. I think the more that you're intentional about defining that, I think folks find there's this balance of people that bring existing skills to the table and then sort of like you have to get them to adopt your culture versus people have maybe relatively fewer skills, but you can teach them and they're good learners. And I think you can decide which is for you. I think a lot of folks tend to think that it's easier to find the ready-made kind of version of people. I tend to think it's actually, well, it takes more time and you have to set up the infrastructure. It's a competitive advantage if you can do

• 32:51Speaker 02

  both. So anyways, we obviously do that a lot in disciplines like product. Product's one of my favorite ones. Every time I interview somebody for a product job, say, so why are you interested in this? Because nobody goes and gets a degree for like product and design. So how did you get here? And that's an example of one where we just have a curriculum internally and say, okay, if you come here, I assume you're going to be, say, a future founder, entrepreneur, future chief product officer, and we are going to put you through a bootcamp to get you there, right? And it's going to be hard. It's going to be intense, but we will give you our opinionated version of what it takes to do great things. And I think if you look at a lot of great product, I mean, they've got similar things, right? For each Indian, obviously you can then extend that to other functions.

• 33:32Logan Bartlett?

  So APT was recruiting on campus and so they pulled you down into that and you had a nice run there, but then you were also purposeful in pursuing performable and trying to learn. I guess as you were thinking through your journey, at what point were you like, hey, I want to be a founder and so I'm going to go round out all these skills? And then how'd you get looped in with performable to round out the sales and some of those other?

• 33:58Speaker 02

  So the first thing was, you know, at school, I just want to be a great engineer. You know, I tried to join a company where there were other people I felt I could really learn from.

• 34:05Logan Bartlett?

  I heard big tech, by the way, like wouldn't even have a conversation with you when you applied.

• 34:10Speaker 02

  Well, I mean, there's two things. Why? I had done an internship at Microsoft, which was great, but I also, you know, I'd heard these like horror stories, and this is like early 2000s, of, hey, you want to be like on a team that has a bunch of like of good people, but not great people, because we have this thing called stack ranking. If everybody's awesome, well, there's only, I don't know, one five star, one like, you know, you're the best of the best.

• 34:38Logan Bartlett?

  Sure.

• 34:38Speaker 02

  Ratings. So you want to be with good people, but not great.

• 34:41Logan Bartlett?

  That was within Microsoft?

• 34:42Speaker 02

  Yeah.

• 34:43Logan Bartlett?

  Back in culture.

• 34:43Speaker 02

  And again, I don't know, it was a pocket team, but somebody had mentioned that that was a kind of a thing. And I was, that was like, I was horrified by that.

• 34:49Logan Bartlett?

  Yeah.

• 34:49Speaker 02

  I was like, that sounds horrible. Like, I want to be at a company where it's, it's all all-stars and it's growing so fast. Like, the pie is just expanding, right? So that's been a very key tenet of mine, like for us at Klaviyo and like all places I chose. Um, so it was, you're a great engineer. By the time I left there, um, I intentionally wanted to join a startup because, you know, I was thinking, I was like, you know, I had these, as I got into programming, I'd been doing a lot, like nights and weekends. Um, I'd spun up a couple of little side projects. I wouldn't call them companies. I never really tried to monetize them. But I was like, okay, this is kind of interesting. I think I may want to try this. This whole entrepreneurship thing. Um, I was like, well, I want to, I want to front receive to see how it's done. So I want to join a really small company, sub, you know, 10 people. And so when I, I decided I was going to stay on the East Coast and it was either Boston or New York.

• 35:34Speaker 02

  And I obviously had a bias to Boston, because that's where I was from. Uh, and so when I, you know, was back, you know, visiting family and friends, I, I asked around, um, and did a little research on like, before this, before there was Angel List, it's like, where do you go find startups? And, uh, and found this company called Performable. And I'd asked around about the CEO and the CTO, because at the time, you know, I would have been like their first or second engineer. I said, I don't even really care what they're doing.

• 36:02Speaker 02

  I just want to work with people that are really good at the craft. And everybody told me, they're like, well, I mean, you know, David Cancel, who was the CEO, and Elias Torres, who was the CTO. Uh, they're like, well, they're multiple time founders. And, uh, you know, David's had a bunch of like success, um, uh, at these other companies. I said, okay, great. Like, that's, that's all I want. And so I met them, uh, and, uh, ended up joining. I even made the mistake of, I was so into it, I was like, I don't even really care what you're building. Like, I just want to work with really smart people. Uh, I also didn't even care where you're working. I had assumed, you know, their Boston company is like, oh, you must be in Cambridge or somewhere in like the kind of suburbs. Oh, no. Like, David at the time was living almost, you know, in New Hampshire, so about

• 36:46Speaker 02

  an hour outside the city. So I realized two weeks before, I was like, oh crap, this is a commuting job, right? But it was totally worth it because they hired exceptionally well, learned a ton there. And we'd have these, you know, it feels a little bit like a movie, but like, we have these, you know, whiteboarding sessions, right? Where, you know, the engineering, the product folks would get together and, you know, David would have an idea about what he wanted to build and we'd kind of like, we'd hash it out and then literally be like, okay, cool. Like, just go prototype it out, go code it. And so it was just very rapid, right? You know, day over day, week over week, like that. And, you know, you're on the front lines with customers. And it was a great experience and it kind of demystified for me what it takes. And you got to see like, you know, well, how, you know, you would

• 37:30Speaker 02

  share, like, here's the revenue numbers and here's how we're finding customers and here's why we're changing our strategy. And by the time after, you know, Performable got acquired by HubSpot, and so, and I said, I'm still very close with the entire team there. But that, at that point, I was like, well, okay, now I've seen what success looks like. Like, this doesn't feel, I mean, like, there's still a lot of risk, like, you can make good decisions, but now I've seen the patterns. Now I think I can really go for it.

• 37:58Logan Bartlett?

  How long was the Performable time?

• 38:00Speaker 02

  I mean, that's great. You know, you can learn a ton in a really short period of time. I was there for about 12 months.

• 38:07Logan Bartlett?

  Wow.

• 38:07Speaker 02

  Yeah. And that was, yeah, it went from, I mean, it was very fast. I think they made maybe even working for like six, 12 months before that. But yeah, it was very, I mean, we did, we accomplished a lot a year.

• 38:16Logan Bartlett?

  Sure. And for people that know now, Performable got acquired by HubSpot, Cancel became Chief Product Officer of HubSpot. And sort of, I mean, I think Alligan gives him a lot of credit for really rebuilding. People sort of forget, but HubSpot was like,

• 38:31Logan Bartlett?

  Sort of a feature-ish initially and David, I think, had a pretty heavy hand performables business and building out into the full modular suite of products that it became today. But that was a pretty linchpin moment, I feel like, in HubSpot's journey from a few products or like a discrete thing into the journey. And then David, obviously, both of them went on to start Drift, which Vista bought for over a billion dollars as well. So repeat entrepreneurs.

• 38:57Speaker 02

  Yeah. And one other thing, I mean, the other reason I recommend going and finding great companies and really great people to work and learn from is, I mean, those folks become, when you want to start something, I mean, when we actually went and raised capital, so after that, we started Klaviyo, we did our two years, getting it to profitability, all this kind of stuff. And when I went and said, like, okay, I think we're going to raise a venture round, I went back to David and Elias and said, well, who do you like? Because they knew who all the, by the way, would you guys be willing to back us? And of course, they were like, yeah, of course. And so that was a really helpful thing because

• 39:40Speaker 02

  they acted as mentors and advisors. And then that's how that introduced me to Brian and Dharmesh and the HubSpot team. And we very much look at there's a lot that I think that that company actually really well, that we've been able to learn from them. So very big fan of this, find great people that like know how to do it and they'll probably surround themselves with other great people. It's a great way, if you're not a big networking, I'm not the big like go to conferences kind of person. It's a great way to meet the people that can actually help and serve as, you know, those could be angels, could be advisors.

• 40:11Logan Bartlett?

  I want to put a pin in the founding story and maybe come back to that. But one of the things, how many people is Klaviyo today?

• 40:18Speaker 02

  We're just about 2,000.

• 40:20Logan Bartlett?

  Oh, I know. That's a vanity metric that you guys.

• 40:22Speaker 02

  We have two vanity metrics. We don't celebrate. We don't celebrate fundraising. We do not celebrate how many people.

• 40:26Logan Bartlett?

  Yeah, but it's still, it's a lot of people within the organization. And along the way, I know your role, like anything that happens with a CEO, growing as the company grows, your rate of learning and development. And skills need to outpace that by which the company is growing. And as you guys have grown really quickly, your skills have had to grow very quickly as well. I guess there's been a number of different functional responsibilities that you've probably had to see it along the way. And I've heard you use the phrase giving up your Lego blocks or whatever it is to describe.

• 40:59Speaker 02

  It's a great talk somebody does about like, right, giving up your toys, which is totally the right mental model for like, you know, growing as a leader. Yeah.

• 41:06Logan Bartlett?

  What did you hold on to longer than you should have in that journey?

• 41:10Speaker 02

  Gosh, probably too many. I mean, like, well, the earliest from the early days, something I would, you know, we talked about how like constraint breeds creativity. I think that's, I think it's very true. Something I think I would have done differently is we probably waited too long to hire, you know, other engineers. You know, for the first few years I was, you know, owned all the code and I was like, okay, well, I've kind of, I figured out a way to make this work, you know, by myself. Man, there was such a massive unlock. Once we actually started to grow that team. And I think that was, I think that's usually been, you know, I, I generally would say I'm very slow to hire.

• 41:45Speaker 02

  And, you know, I think there's, there's this norm in startups, you know, I know this is entirely intent of like, you know, Reid Hoffman's book Blitzscaling. But there's this concept, you know, this concept of like, just go fast, right? Like the idea is speed, go win the market. Because, you know, there's sort of first mover advantage. I have often says like, no, I'd rather not do that. Like I'll, I'll be slow. And I think that's generally worked well for us. But I think my biggest mistakes, like the things I've held on to are things that, yeah, we either, I should have delegated that to somebody, let them run with it.

• 42:20Speaker 02

  And, or we should have just grown a certain team faster. So, I mean, I think for years we were a very lean, you know, product engineering group, which is good. Cause I mean, you get some people that really understand everything.

• 42:36Speaker 02

  But in retrospect, it's like, boy, we could have gone a lot faster.

• 42:40Speaker 02

  Yeah, after that, I mean, my, my, this isn't quite like which things to give up, but I, uh, somebody once is probably four or five years ago, gave me the advice, they're like, look, Andrew, there's, there's effectively three jobs you can have. One is when you're the person doing the work. Okay. So we think of like the, you know, the quote, quote, I see, right? You're, you're the expert, you're getting the work done. Okay. So that's level one. Level two is now you're like the leader of a group of people that's doing that, right? So you're the, you're the manager. And that's now there's one level of indirection. And then the third is like, okay, now you're the, you know, you're the, there's one more level of indirection, right? You're the like lead of lead, leader, leader of a bunch of leaders who in themselves have teams. I think that's actually a really good mental model to think about like what gets challenging.

• 43:23Speaker 02

  Cause for a lot of new leaders, I think the challenge is like, well, gosh, I was really good at this. Like, how do I, you know, coach and mentor and evaluate and like, gosh, I have to set the goals, but make sure I don't do the work. And I think that's a, that's a, that's a skill. And then there's this like level of indirection where it's like, okay, gosh, well, how do I, you know, influence and inspire a really large group? Where I may not know what's going on. Or, or what's my, what's my operating system such that I can inspect? What's going on several layers down the stack quickly? When there's more complexity. That I think developing that, you know, kind of like that tier three model.

• 44:03Speaker 02

  Is something that, you know, the, if you realize that's coming, sort of getting in front of that and starting to build that faster will help. You know, feedback that I've gotten over the years is, you know, the clearer, you know, that I make my operating system, like the way the interfaces that I'm going to have, the way that I want to work. To others, you know, the easier it is for folks to go execute. And when there's not clarity on that, not just like what the strategy is, but literally like, okay, so when are we going to look at that and review that and who makes decisions? That's often where things slow down the most. And I've often felt like, okay, well, I feel like if I tell you what I'm going to do, like, that's like constraining you too much, but actually be like, no, no.

• 44:45Speaker 02

  We actually want that constraint and then we'll operate within whatever bounds it is. So for instance, our product team, you know, we just have a norm of, hey, here's how we're going to evaluate which projects we're going to work on, what our strategy is going to be, what goes on the roadmap. And it's very clear about like, hey, these are the check-in points, right? And that actually gives a lot of freedom for folks to experiment with ideas, you know, and off they go. And then we have another process by which it's like, if you want to spin up a whole new product inside of Klaviyo, great, the doors are always open. But these are the requirements, right? Here's the sweat equity you got to put in. Here's the prototype you got to bring. You got to have some idea of the projections of like, what does usage or revenue look like 12, 24 months? Not any different really from like, you know, pitching, right? If you're going to go

• 45:29Speaker 02

  raise outside capital. But the fact that we have that has been an enormous accelerant. So it's a lot of like, setting up those structures, you know, lightweight enough, but deterministic enough, that folks can then, you know, operate within that.

• 45:41Logan Bartlett?

  So there's, I guess, two components of that. I think in the higher abstraction of being a manager of managers, and one of them is the operating principles and some of those gaining milestones. And I think the other one is probably some culture tenants related. And the two aren't totally disparate from one another. But I'm curious, when going back and prepping for this, I was listening to some of the older podcasts you had done. And one of the things that you, you mentioned that you wanted to get better at, or one of the learning things that you had maybe talked about four years ago, was actually setting up a culture of, it's not experimentation, because I think you guys have probably always had a culture of experimentation, but product development or founding development with it for new business units and all that within the, within the business.

• 46:26Logan Bartlett?

  How have you, it sounds like you've made progress on it, given what you just said, but how have you sort of set up those frameworks and milestones and like, the discrete points of the journey along the way?

• 46:35Speaker 02

  Yeah, so I think there's, we have this concept internally of like, you want, you want A culture to have high entrepreneurial density. What does that mean? It doesn't necessarily mean somebody has to have gone and founded a business. But you want folks that will take ownership and sort of say, hey, if there's a problem, I'm going to go solve it. So, okay, if you've got, say, then a, you know, high density of folks that want to do that, you know, a lot of them are going to come. They're going to bring, they're going to bring problems or solutions and say, hey, can we just go do this? How do I fund this? So, yeah, well, we, we're not, we're not perfect at this yet. We've done a better job on the product side than we have in other places like, um, but, uh, but yeah, you want to say it's like, okay, cool. Well, how, because the question everybody comes back is like, how do I get this funded? Right. Cause I have this idea and I want to go do it. Like, how do I make it my full-time job?

• 47:19Speaker 02

  And how do I get other people to come with me and work on it? So, uh, it's interesting. We've taken, I mean, really just off of the way that, you know, uh, venture capitalists or investors make decisions. We've taken the same kind of like seed, series A, B, C model and just set that up internally. So I was actually doing this a few months ago is, uh, you know, we, we do check-ins. We have a sort of a different cadence than we do with our regular like kind of core product roadmap. In those cases, I treat those very much like, yeah, you're a startup. So that's, I mean, you know, when we were the first, I don't know, three, four, five, six years, we didn't have board meetings. We would just check in, you know, every six, eight weeks. And there was kind of like a standard little format we have of like, okay, you know, like what are our, what are our core metrics of our business? And even to those folks, we'll expose to them like their P and L.

• 48:04Speaker 02

  We'll say it's like, look, this is how many people are working on this project. This is how much you cost. This is how much revenue you're bringing in. And what was interesting is we, I, I don't think I was a really, we found that people are very motivated by that. When they can see that and they can see their burn rate and they know, okay, gosh, here's how I'm trending. It, I think it even more first forces this like ownership of an urgency around what they're trying to accomplish. So we've done that and we now have, uh, gosh, probably like, you know, half a dozen kind of like at scale. Like, you know, like there's, there's a meaningful number of people, like not hundreds, but like, you know, tens of folks work on things. And, uh, since we started that a couple of years ago, and, uh, yeah, I mean, I think that's, we talked about like, you know, uh, evolving into offering more products.

• 48:49Speaker 02

  You know, for instance, we believe Claudio on top of, um, You know, this database that we built, like, marketing is just the first interface. I mean, there's plenty of other interfaces between a business and a consumer. You know, like, what about customer service? Like, what about the actual, like, the website or the mobile experience? Like, there's plenty of these things. And we have people that are working on all of those, right? And we've followed this model and it's, we've tried to resist hard this urge to kind of centrally plan those. So it's a discussion debate we have a lot of, like, when does it make sense to kind of centrally plan them because we have to move quickly versus when is it good to have this kind of, like, startup model? And I think our general philosophy is it's better to aim for the, you know, kind of startup model where we can. If it's really urgent, then I think we should have urgency in finding the right, you know,

• 49:34Speaker 02

  founder, so to speak, for that business, you know, to kind of drive it.

• 49:38Logan Bartlett?

  In terms of giving autonomy to the people, the founder within it versus the considerations that lead to the shared service on the backend, so it's not discrete products? Like, I assume you're not allowing people to be picked between the cloud providers or the databases that they want? Like, how do you sort of think about where you're going to make it autonomous and empowered versus shared?

• 50:03Speaker 02

  It's a great question. I mean, it's something that we've, we've learned a lot, a lot of battle scars from that over the last few years. I give a lot of credit to the, like, you know, to the Klaviyo that, like, kind of were on the first teams that did this.

• 50:16Logan Bartlett?

  Klaviyo is our employees.

• 50:18Speaker 02

  Yeah, yeah, yeah, our employees. Yeah, so, for instance, actually, the first, the first team that did this actually set up a whole nother cloud hosting accounts because, you know, they branded it differently and everything, right? Because they want to be totally different. I think they found, actually, that it was easy. There was a lot of, like, I mean, there was some freedom from that and some things that were like, oh, gosh, this is redundant. So, yeah, I mean, look, when it comes to, there's primitives that we want to offer, you know, we're, I think our customers expect of products that come from us. So, things that are secure, things that are reliable, things that will scale. And so those are primitives that we have a platform team that just, yep, here's what you get for building blocks. I think a lot of what we learned was, well, what are those core building blocks? And what

• 51:03Speaker 02

  What are the interfaces that teams need to go be successful so they can have autonomy?

• 51:09Speaker 02

  That's probably was the biggest one. There's, you know, there were some other things of, you know, hiring was very interesting. Well, do you have to follow the same hiring process or not? And so we've largely said, yes, we should have some norms around hiring, but like, you know, you can make the decisions, you know, somewhat, somewhat more autonomously than maybe our core, core teams do. So there's a lot of little things like that that we've had to sort out. But I think once you do, I mean, we really tried to, I've tried to put people in the, because I, there's, there's no doubt in my mind, I would have potentially stayed if a program like this had existed at the first company I worked at, APT. And, you know, it's no fault of theirs, but like, I think back to this, if there had been a program like that where they said, hey,

• 51:54Speaker 02

  we're really going to put you out on an island here. You got to sink or swim all by yourself, but you're going to do in the confines of this organization. There's probably a good chance I would have stayed for a lot longer. And I just, it wasn't really something that they were anticipating or considering, but it's, it's definitely made me think about Klaviyo. Cause I, I mean, we've had now dozens of people go off and start companies outside of Klaviyo, which is great. It's one of these like kind of very bittersweet conversations when somebody says,

• 52:18Logan Bartlett?

  Sure.

• 52:19Speaker 02

  I'm sorry, but I've been working on this thing and I'm leaving. And it's like, okay, Godspeed. Like, have that. I think a lot more of those folks, you know, a bunch of folks that are very unfamiliar will say, well, actually, maybe I don't want to strike it on my own. I actually like this, you know, product category. I just need a construct that gives me more of this like freedom because I do want more risk reward.

• 52:37Logan Bartlett?

  Yeah. It's a double, it's sort of recruiting the entrepreneurial person that, that, that might leave the confines of the organization at some point. It sounds like you guys, if there's two things in hearing you talk here and then also in doing prep for this, that you maybe uniquely solve for is, and I'd love to talk about how you, because you alluded to hiring, how you tease this out in interviews. One is kind of this individualistic empowerment entrepreneurial side of things. And figuring that out, most people I've found, it's much more comfortable. To be told what to do than to stare at a blank piece of paper and figure out what to do.

• 53:18Logan Bartlett?

  It's just, I think 95%, 99%, 90%, I don't know what the right number is. But are people that, I'll colloquially call it football players versus basketball players. Like football players, they get told what to do, they do their job and they do it well. They can be great team members, but they're not creating in space the way like a basketball player, soccer player will do. I think Keith Roy has something barrels and ammunition. The people that are firing versus the people that are aiming and all that. How do you go about teasing out the people that are individualistic enough, empowered enough in an interview process? Cause I've always just found it's a, it's a very hard, everyone says the right lip service of like, oh yeah, I'm a self-starter and all that. But how do you guys go about actually finding that?

• 54:01Speaker 02

  Yeah, it's a good question. I don't think you can kind of manufacture a, you know, a question or a case study and say, here, kind of solve this, prove to me, it's all a track record thing. So there's some skills that I think, you know, you can only show by having done them. And you can end up in these spots where somebody's like, well, no, I'm telling you, I really am. And I'm like, well, if you were, you would have done it already.

• 54:23Logan Bartlett?

  Yeah.

• 54:24Speaker 02

  So our trick for that is, I, or our technique is I'm a very big fan of like kind of, you know, the resume walk or kind of the life story. I think a lot of people, when you boil it down, like if you tell them, tell me about the projects you've worked on. And if you ask kind of really kind of like detailed questions about like, well, how did you make that decision? Or why did you decide to do that? You know, entrepreneurial folks, I find like, they won't go to others to, you know, ask, well, what should I do in this situation? They'll, they'll have a higher percentage of times where they're like, well, I wasn't sure what to do here. And so here's how I came up with a strategy, here's the research I did. And here's the, here's how I thought about the options. Here's what I experimented with, didn't work, so I went back and did this other thing. They have lots of stories like that.

• 55:07Speaker 02

  And I think one of the things that we're careful about is it doesn't, you know, Entrepreneurship does not equate to like you have to run a business.

• 55:15Logan Bartlett?

  Oh, sure.

• 55:15Speaker 02

  It can, it can, I mean, there's, it's everywhere. And so it's just sort of asking those questions. And the fun part is, I think most entrepreneurs, I mean, look, they kind of wear as a badge of honor of, you know, well, yeah, let me tell you all the things I tried and this one failed and like, but then I succeeded. I mean, they almost can't help but talk about it. So we love that kind of, you know, a little bit life story. And we look for those folks that are kind of proactively decisive. And if they're doing that, then I think there's a good chance that when you put them in those spots in the future, hey, they'll, you know, they'll, they'll sort of surprise you with what, with what they've done.

• 55:49Speaker 02

  But it is one of those things, I mean, there's a couple of skills like this, like, you know, that's one of them where, you know, our advice to folks is like, you, you kind of can't, you, the only way you can prove to somebody you do it is by doing it. You have to have a track record. You know, another one that we, I often look for, you know, is folks that are, what we look for all the time is like folks that are like super curious, they're really good learners. And it's one of those things where it's, it's actually really easy to vet. You just say like, that's awesome. So I'm sure you're learning about something right now. What are you nerding out on? And you get sometimes people that give you the answer of like, well, for my job, like I have to read this page. And I'm like, hang on, like, that sounds like a everyday thing. And then you get the people that are just naturally, well, yeah, I'm reading this book and I think that's really interesting.

• 56:32Speaker 02

  Or I listened to this podcast or I watched this video the other day. And sometimes it has nothing to do with their day to day. So it's just something that they're passionate about, they got into. And I think what's hard is we all, you want people that are like that. And oftentimes when, you know, I think you hear people, it's like, well, I don't, well, they don't, they don't bring it up. You're like, well, that's okay. Maybe I just asked a question the wrong way. It's like, no, like the folks that are truly curious and are learners or entrepreneurial, it'll be so self-evident. The real challenge is, I think, just, you know, showing that, like, is finding those folks. So one, in our, one of our, you know, one of our strategies for that is we just advertise straight up. You know, on our website, like when I go talk to folks, I'm like, look, I'll tell you the cheat code to get into our company, right?

• 57:16Speaker 02

  But you have to have, you have to, you have to, you have to be able to tell me you have a track record of these things. So if you don't. Like great, like tonight is a good night to start working on this. And if you don't want to, that's fine, but like basically we'll tell you what the test is going to be, so to speak, what our bar is. And then you just need to bring the track record. And I think actually advertising that we're for that, there's a lot of people that are like, you know, gracious learners or they're They actually, I think those people like to cluster around each other. And so if you just kind of advertise it like, hey, we're going to be this beacon of that. Then actually you'll get a lot of people that are like, oh, that's good because I was looking for that and a lot of companies, I mean, a lot of companies frankly, don't want people to be entrepreneurial.

• 57:54Logan Bartlett?

  Yeah.

• 57:54Speaker 02

  Hey, we've got the plan. We kind of just need you to do your job. As long as you do your job, you get rewarded. And so I think by us saying like, no, we actually, we want, we want you that you're a little rebellious and you think outside the box. It's actually, you can get people to attract themselves and, you know, their friends.

• 58:10Logan Bartlett?

  You believe that resume should be laid out in chronological fashion rather than reverse chronological fashion? And we talked a little bit about the narrative of the journey and hearing about the inputs. Can you just, I think it's an interesting point, or it's something that I hadn't thought of because normally resumes, okay, here's where I was. And then here's where I was before that. Here's where I was before that. And then your eyes sort of drift and by the end you've lost the plot.

• 58:35Speaker 02

  Nobody really looks at the first step, right?

• 58:37Logan Bartlett?

  Yeah, exactly. By the end you're like, okay, you did that seven years ago and let's talk about this thing. But your eyes gravitate to what's top of the page. So it's, it's an interesting point. Why, why do you think that laying it out in that way is more?

• 58:52Speaker 02

  Yeah. I mean, look, I mean, like obviously somebody's like recent experience may be the most relevant to this thing.

• 58:58Speaker 02

  I just love asking folks, you know, I love asking folks like, okay, cool. So, you know, tell me about like after school, you got this, you got your first job. Like, tell me, why'd you decide to do that?

• 59:10Speaker 02

  You know, what, why'd you pick that company? And, you know, what'd you accomplish there? And then I find that when you do it in this kind of, you know, chronological way, folks actually open up a lot more. They're like, oh, well, let me go back in time. Yeah, the reason was this. And it's like, okay, now think about that stretch, right? Say it's a couple of years. What are you most proud of from there? Oh, okay. Well, that project was really interesting. What'd you learn? And so I feel like it's actually easier to kind of unpack, you know, so I often guide folks when I meet them, I'm like, hey, look, I'd love to talk through your kind of story, but like, let's, let's do it from the start. It's actually very disarming. A lot of people are like, oh, you mean like where I got my first job there? I mean, especially if somebody has like a, you know, say 10, 20 year career. Oh man, it's so long ago. I mean, you know, it really takes the pressure off and feels less like an interview.

• 59:55Speaker 02

  I mean, there's obviously merits to like the things that are maybe most relevant, you know, are, you know, more local, but I take that. Part of the reason I believe that when you're actually trying to understand somebody, you have to look at their whole body of work. And if you're just looking at the last, you know, say the last thing they did, the last year or two, it's very transactional. It's just like, look, I need, I need somebody that does this job. Can you just tell me if you've done this job recently and if you have grades? And it's like, well, I mean, you know, I'll say somebody's, uh, you know, uh, 30 or 40 years old. I mean, you're literally looking at like three, you know, like, you know, three or 4% of their life.

• 1:00:28Logan Bartlett?

  Yeah.

• 1:00:29Speaker 02

  It's like, that's not a very, you could just, people are actually willing to share more than that. And if you just, you know, give them a chance.

• 1:00:34Logan Bartlett?

  Throw about it. Yeah, there's a derivative consideration of it, which I, I, I thought maybe you're going to say, and maybe is implicit in this is the rate of learning and the inputs into the deciding of each step along the way. Like I, people would jump jobs and that's fine and you can switch, but like hearing the input and the process by which they, they did that, did they learn new things in that job that led them to taking the next chance along the way? And what were the inputs into it? What did they hope to accomplish? What were right or wrong along the journey? And then what did they then leverage from there? And generally it doesn't need to be a linear path, right? It can be step functions along the way and a nonlinear one.

• 1:01:17Logan Bartlett?

  But it is very informative to talk through each discrete decision and you don't get that in the reverse looking way of, of, you know, what you've done most recently.

• 1:01:27Speaker 02

  Yeah, definitely. Yeah. I mean, first of all, I'm a big advocate for, I mean, both my parents have had, I mean, I think they've had like one or two jobs in their entire careers. I think it's a little crazy. I mean, it's just, but it's certainly now it's a lot easier, uh, to. I think you should try different things. Um, there's a Richard Feynman physicist, I can't remember, I always get this wrong, but he went to undergrad on either the east coast or west coast and then switched for his grad work. And it was the fact that he did both that he understood he's like two great departments. I think it was like, I think it was Berkeley and Princeton were the two. And he learned, he's like, they were very different cultures, ways of working, but like, it was actually doing both that like made him who he was.

• 1:02:08Speaker 02

  So there's nothing wrong with like, I mean, you should, I think you should have a lot of different projects, whether it's inside a company or just try different companies. But it's, that's exactly right. It's this, what is your logic for why you made these decisions? And, you know, it doesn't have to be a master plan and the master plan doesn't have to like necessarily work out the way you thought it would. But having a point of view on, you know, oh, I was intentional about going from this to that because of, you know, for this reason, I wanted to learn or try this thing. Is a massive tell and like, yeah, I mean, all the, all the great people, when you ask them about that, I mean, they're, they're happy to tell you about this because they're like, yeah, I was thinking through this and maybe this, this works. I learned I didn't like that, but I really liked this.

• 1:02:46Logan Bartlett?

  Cause if you're not purposeful or considerate about your own career, which maybe outside of who you marry or whatever, a few other considerations. It's probably on the discrete project I give you, you're probably not going to be like, if you didn't choose in a purposeful manner around that, have you ever read the book Range?

• 1:03:03Speaker 02

  Yes.

• 1:03:03Logan Bartlett?

  It's, it's interesting. I mean, what you said about east coast and west coast and, and pulling from different threads together to, to, to solve problems. It's, it's very, um, it's, it's, uh, it just reminds me of, of that, of how, how the, some of the breakthroughs we have as society come from broad experiences and pulling all that stuff together.

• 1:03:25Speaker 02

  Oh yeah, the crosswalks.

• 1:03:26Logan Bartlett?

  Yeah, there's a number of things. I mean, I found in some ways the, the venture capital job itself actually lends itself to two of the character, both those characteristics. Curious for obvious reasons, you're going to look at a bunch of different things, but then also, um, There's, you can justify, your day is going to start blank for the most part. Like, and you can do any, you could have a podcast, you can, whatever, go to networking events all day. You could fly to a conference, like you can justify all these different things. And most people are actually pretty, it's, it's discomforting to not really be told what to do in general and how to spend your time, especially when there's a whole bunch of mental models of how people have been successful in the venture capital industry.

• 1:04:10Logan Bartlett?

  But I found it's interesting, you could find people that are entrepreneurial in anything that you can just ask the question of like, what in your job was kind of broken or at your school was kind of broken? And what did you create to fix that, right? And maybe they started a club, right? Or maybe they redid the comps, they're an investment banker and they, the way they were doing comps didn't make sense and they redid it from the scratch. Or maybe the recruiting process was broken and they just took over the high school or the junior, or whatever, the college recruiting process or something. I found that all of those little things, it's really hard to fake that stuff, that you just saw something where there's smoke, you yelled fire and you went and fixed it, right?

• 1:04:52Logan Bartlett?

  And like, that manifests itself no matter what the job is, or even if it's not a job. If you're in college or, those types of people tend to find a lot of different stoves to touch.

• 1:05:01Speaker 02

  Yes.

• 1:05:02Logan Bartlett?

  And fix those problems. And so teasing it out is always a little hard, but generally they go deep.

• 1:05:06Speaker 02

  Well, the good news is, like I said, I think most people don't like, I mean, they like to gush about those things. They won't hide them. So if people have those stories, that's right, and you kind of pro offer it up. Hey, give me time, if something was broken, you fixed it. I mean, folks that have those would be like, well, let me tell you, right? So it's, yeah, it just, you just kind of have to ask and you have to be, look, I mean, not everybody, like you said, not everybody operates that way. You just have to be willing to, that, hey, if somebody doesn't, you know, if somebody doesn't give you any evidence of that, it's not probably because you asked a bad question. It's probably just because maybe they haven't done it.

• 1:05:35Logan Bartlett?

  Which is, which is fine. And there's a lot of great companies that people can go work at, but it's not going to be the same individualistic and empowering of that. Now, so operating principles and like different things you guys espouse internally. And we've been, we've been talking about some of them related to hiring and maybe I'll circle back to hiring. A second, but eating your vegetables is is an adage, I guess, or something of a core principle that you guys speak to. Can you elaborate on what that is? When I heard it referenced, I didn't hear the full depth of where it comes from and what the purpose of it is. So I'm curious.

• 1:06:09Speaker 02

  A little bit from when and I where there's just the two of us. I think a lot of it's, you know, it's, it's always kind of sexy to work on, you know, the flashy, you know, it's the net new project, products, open up a new market.

• 1:06:23Speaker 02

  You know, we, we talk about like fixing the kind of the, whether you call them paper cuts or the loose nails like, but going and doing that work, which is entirely unsexy. That's where this eat your vegetables kind of comes from is, yeah, that's actually celebrated inside of. We have a whole thing, this kind of ever, evergreen, you know, I guess, theme initiative inside the company, which is like, how do we just automate more stuff away? And just like teams that go around and are just like, just constantly finding problems where it's like, well, that, that seems silly and like, let's just automate it. And, you know, we have to do an all hands every week and I love when we celebrate things like, hey, here's this thing that's maybe it was like an employee process, or maybe something for our customers or whatever, it's just something that's, that just sucked.

• 1:07:08Speaker 02

  And it's like, oh yeah, that used to cost, I don't know, it used to cost somebody an hour every time they did it. And now it costs a minute or now it's actually just zero. And it's just celebrating that. And so the, the kind of eat your vegetables is a little bit like, hey, we're going to celebrate that. But also the best time to solve those problems, if you're scaling, is today.

• 1:07:27Speaker 02

  So this comes up all the time, you know, it's, you know, I'll use an engineering analogy, but like it's, it's everywhere. Is if you have some process or system that's not scaling and it's, you know, kind of on fire. And I remember in the early days, like, gosh, you'd built some system and it, you know, it would break every now and then. And it's like, every time, you know, you two X would break twice as often. And at some point you're like, well, this is silly, we just need to fix this. And we've always had this mentality, it's like, if you, you just want to go solve and eliminate those distractions. So, you know, before you like eat the dessert or eat your makeup, like just go do the stuff that feels like it's going to stink. Because it's going to free you up to do a lot more. So I really, I love that. And then there's maybe a side thing for us, which is it's not quite the same, but it's, we have a very humble culture.

• 1:08:15Speaker 02

  And I think there's, you know, you want to have enough confidence that like, hey, you know, you know, you're, you know, you're going to win, you've got a strategy you really believe in, right? But we have the humility to say that it's like, look, the unsexy stuff like is not, you know, beneath us, right? It's not somebody else's job, right? Like I get excited about that stuff. And in general, this kind of like, we're going to roll up our sleeves to do the things that we know are going to long-term, you know, give us the most leverage. Be most impactful. Like, I think that's, that's a big part of just how we, how we, the kinds of people we, uh, you know, like to have at Klaviyo and then how we like to work.

• 1:08:48Logan Bartlett?

  The companies I have that have the most, I would say entrepreneurial employees within the organization. That, that, that spin out the most future companies and all that, that there's a risk or a potential tension that, um, that taking things from zero to 90% done is a lot more fun than 90 to rounding out all those edges at the end. And so do you hire for different people that enjoy chewing the glass of the final 10%? Or is it just simply the celebrating of it that gets the people that are entrepreneurial to go do it?

• 1:09:27Speaker 02

  We try to avoid this like, you know, hey, there's folks that get to do the fun part and then the other part that has to front the chew glass at the end. Yeah, I think a lot of it boils down to, sorry. So for example, like, uh, one of my favorite things to do is when we're nearing the end of a project. You know, I make this analogy of like, if you're, you know, you say you build a new house. And, you know, you're, you're the master builder and you're walking through and you're like, okay, well, there's like a loose nail there and ah crap, this faucet's not, you know, doesn't work quite right. And you make this big punch list of all the stuff that you're going to do, but they're all like easy things. So one of the things we do, because when you get towards the end of a project, you're like, oh man, what do we have to do to ship a ship? We have this moment where we like to just build that like, you know, that house walkthrough. And we give everybody, it's like, okay, cool. Just go through, like, let's find all the loose nails.

• 1:10:12Speaker 02

  And like, let's, we're going to bang down all the ones we can. Anything that's not, we're going to put in like version two, right? And we're just going to ship this thing. So I think that, that. Putting that in there and then kind of celebrating that as a moment and then having that that ship date makes a big difference. Also, very big fans of you just got to ship. I mean, there's nothing like the, you know, endorphin rush of things out the door. And it's not just a product, right? It could be, um, you know, hey, we're working with a customer on a project and we want to give us advice like, let's just get that out the door. So, uh, one of the things that I think is it feels a little paradoxical, but the folks that do the highest quality work, either individuals or teams, also are the ones that ship most frequently. Uh, it's something we talk a lot about. Like, there's a thing of

• 1:10:55Speaker 02

  like, oh, no, no, you know, because you see sometimes outside, like, well, they do really high quality work, but it only comes out every now and then. And so, boy, they must just take a long time on every decision. It's like, no, I don't think that's right. It's just they're iterating in private. You can't see it, but they're really moving fast. And so that's a thing that we try to, you know, coach folks is, hey, look, if you want to do really high quality work, the best way to do it is lots of reps and sets. Like, you're going to make mistakes and we can do that in private, but the idea is, you know, like, cycle time matters. So, hey, if we're, you know, uh, you know, we have a big writing culture inside of Clivio. If you're going to write up a narrative, uh, or a memo on something, great. It's like, well, I'll give you the draft in two weeks. Two weeks? Give me, give me the outline, you know, tomorrow, right? And let's iterate

• 1:11:38Speaker 02

  on it three, four times and or you should iterate on it three, four times. And that's how we get things better. And then this really pushing cycle time, I think, makes, makes a difference. Um, I think it was, I can't remember who said this, but, uh, but this idea of, you know, companies all have their kind of internal clocks and they can totally be tuned. But there's a difference between companies that are like, okay, I'll get back to you next week versus I'll get back to you tomorrow versus I'll get back to you later today.

• 1:12:04Logan Bartlett?

  Yeah.

• 1:12:04Speaker 02

  And I think we would all bet on, it's like, oh, okay, the team that has like just the faster cycle time. Like, again, they may not get it right the first time, but they're probably getting more shots on goal and ultimately be more successful.

• 1:12:15Logan Bartlett?

  Yeah, it's a trying to do this within a venture firm, which is a weird organization in general to do it. But I'll say, um, like, schedule a meeting, uh, particularly soon and, uh, and people will, well, that's too soon. I was like, well, we, we have to have the first meeting to have the second meeting. Because the first meeting is like, okay, none of this stuff is going to be totally fleshed out. The learning thing, we've talked a little bit about the founder experience and the journey that you guys are, you want to impart to the different employees along the way to set them up. I've heard you say, I mean, we've talked a little bit about this, but like you philosophically are training people to be

• 1:12:56Logan Bartlett?

  future founders, even if not outside the four walls of Klaviyo. Like you want to build that skill set. Klaviyo University is a thing that you guys have started. Can you talk a little bit about that? And like, what are the systemized, systematized elements of like actually training people to be future founders? How do you think about it?

• 1:13:19Speaker 02

  Yeah, and look, you know, you go through this progression, or at least I have of, you know, what does success look like? And again, you kind of can just find it, but this goes back to like, you know, a five year plan is a good thing.

• 1:13:30Speaker 02

  You know, when we started was like, okay, let's make sure Klaviyo is a successful company, like it's viable. And then you start to say like, okay, well, great, well, how much impact can we have? How many customers can we have? I mean, we definitely think we can have millions of customers. Okay, well, how core can we be to, you know, how they run their business, how they evolve their business? Oh man, we can do a lot more than we're doing today. She started to build a bigger business. And then at some point, I mean, I've had this experience now a couple of times with working with other folks that built great companies. But then they have their kind of tree of folks that, you know, they had an impact on. And, uh, you know, we very much look at like, how do we pay that forward? So I think part of that is the world just literally needs more people creating, creating companies, creating businesses, more entrepreneurs.

• 1:14:15Speaker 02

  And so we want to demystify that as much as possible. So that's part of it. We're also very happy is, you know, we've had folks go off and become leaders at other companies and that's great. So I think, you know, a lot of companies get admired because like, wow, they have such a great leadership development program. So whatever those skills are that matter, right? They're like, oh, um, folks go off, they start new businesses, that's great, they must be really creative. Or man, those are great operators, leaders of businesses. And so we aspire to, you know, have a lot of folks go do both. So Klaviyo University is something we, a concept we started a while back, which was, you know, built this idea of, okay, well, if you're going to hire people that want to learn a lot. I mean, one of the things that actually happens pretty quickly is folks start to say, well, what should I learn? Like, help me aim. You know, one of the first things we have is policy inside of Klaviyo. It's our free book policy.

• 1:15:00Speaker 02

  One of the things David Cancel gave me at Performable that I was like, oh, this is a great idea. I'm gonna definitely gonna borrow this. He said, Andrew, nobody has ever gone broke buying books. So if you are a, if you are a learner, like you should just read as much as you can. And I think one of the things he suggested, but we did, he might have done this at Drift. We then pulled into Klaviyo was like, okay, we're gonna make it really easy. If you wanna go learn about something, like you can go order that book. You know, I don't even want you to worry about the fact that it costs 10 bucks, right? Um, now, the secondary effect of that was almost instantly you're like, well, this is great, but like, what's our reading list? You know, what books do you recommend? And so we had to build out this whole library of like, okay, well, if you're trying to learn about this, like,

• 1:15:42Speaker 02

  these are good biographies or autobiographies of founders. These are like the business-y books that we think are actually worth the time. All this kind of stuff. Um, so, uh, that became kind of the start of Klaviyo University and he said, okay, well, how can we formalize this even further? And I always liked the idea of, you know, in college or, you know, in school, there's always like kind of the core curriculum that you have to do. And then there's like a bunch of electives. And, you know, I looked at those courses as, I'm like, okay, well, it's like, oh, what does somebody do? Somebody just basically curated like, look, if you do the following exercises or the following stuff, like you'll gain this skill. And it's like, okay, well, we should try to systematize that rather than just expect people to go figure it out themselves. Like, let's, you know, let's figure out how we do that. We can build the content ourselves. There's so many, you know, L M, like, you know,

• 1:16:26Speaker 02

  systems or content online. We can pick out and curate what's best. We've had folks come in from the outside to effectively be like professors inside of our university. And so what we started out with was, well, what's the core curriculum of Klaviyo? And, uh, it started actually a bunch of years ago where we said like, okay, well, let's give you two classes you must take. The first is you have to know our customers, right? I think every company should have something like it. So we literally would say it's like, okay, everybody has to spend two days a year and we're gonna haul a bunch of our customers in or invite them in. And they're gonna do a panel and they're gonna give you all the nitty-gritty of like how their business actually works. And most of it has nothing to do with our software. So because we work with a lot of retailers, e-commerce, we like literally would ask them,

• 1:17:10Speaker 02

  how do you go about sourcing products? How do you do manufacturing? How do you do design? How do you decide what the next product is? Fascinating conversations that kind of gets you to be a follow up like, you know, we talk about these like these iconic businesses, you know, whether they're like, you know, doing clothing and apparel or toys or other electronics. How do you figure this stuff out? So you learn about that process. Then you think about how do they do distribution? And you start to realize, oh, my gosh, like a lot of these businesses are so dependent or reliant on, you know, wholesaling, on these distribution networks. And a big part of their strategy is to shift that towards more, well, we want to go direct to the customer.

• 1:17:52Speaker 02

  We want to at least have that relationship with them so that we can tell them about what's new and, you know, and personalize that experience. And so then people can start to tie it back to, okay, God, I kind of see where we started. So that became class, you know, number one, right? And we literally put this little like course catalog book. Then we started to think like, what are other things we just want to level people up on? Another one that was kind of obvious was like writing. Gosh, a lot of people go to school and they write and maybe take one class in college and they never write again. And I've seen this thing where folks join, you know, I don't know, like the business world and all of a sudden they're writing just like, they don't write like they'd write to their, their mom, their dad, their friends. They write in this like business.

• 1:18:30Logan Bartlett?

  Yeah.

• 1:18:30Speaker 02

  And it's like, where did that come from? They're like, hang on, we can fix this, you know, like rather than, and rather than coach it one by one, because it's like very painful. It's like, let's just, let's just go back to like, you know, it's not quite how to write a five paragraph essay, but something like that, right? So writing became a thing. And we just said like, look, there's going to be a couple of these core classes. Part of the contract of working at Klaviyo is you're invested in learning. We're going to help level you up on skills that are going to be useful here or somewhere else. But you, you know, our commitment to you is we'll, we'll set the table, but you have to go take them, right? And this is like, you know, it's, it's a little bit outside of, you know, the normal like, Office hours, all this kind of stuff. And so we started with that and that went really well. And then we expanded that to say, hey, we've got some kind of electives.

• 1:19:15Speaker 02

  So, you know, this was, you know, four or five years ago. We had a lot of folks who were really interested in like machine learning. Hey, I just want to get deeper into that. A lot of folks in the engineering team, but also like folks on our ops team. So we're just like, I've got all this data. I know I should be doing more, but I, how do I do this? We're like, well, look, it's more fun to do it together. So we, in that case, we just, we hired somebody to come in and we're like, look, I want you to teach a class for three months. We'll meet every Tuesday, Wednesday evening and off you go. So we're very big fans of this idea of, you know, great companies have these kinds of behind the scenes, like training, you know, universities or like, you know, kind of curriculums. So we should build out our own and it's the kind of thing, it's not, it's not very sexy, like something you talk about all the time.

• 1:19:57Speaker 02

  But I think it's one of the things that how you could build up some of this entrepreneurial talents.

• 1:20:01Logan Bartlett?

  And so how often?

• 1:20:01Speaker 02

  Just like the mentoring.

• 1:20:02Logan Bartlett?

  Yeah. How often do these things run? Like what is, it sounds like the customer thing everyone does. Is that a part of the onboarding process? Like the writing thing sounds like everyone does. Is that a part of like, when did these fit in? How has it been systematized?

• 1:20:16Speaker 02

  Yeah, it's a good question. So we've actually, I mean, we, we were really good at this right up until COVID. It got a little harder when everybody was, went remote. So now, yes, everybody meets customers, learns customers as part of onboarding. And we're actually right now in the process of like revamping that now that we're going back more into offices where we can say, hey, okay, now we can pick the days. And in the writing class is like, yeah, I mean, we basically, we have a curriculum for that now. And I think we're going to start picking that back up as like a formal thing of like, hey, you can be in a cohort. One of the, one of the things we found is this idea of like learning as a group is like very powerful.

• 1:20:57Speaker 02

  You know, a lot of folks, and we look at like, why do they stop doing kind of self paced stuff? It's because, well, I'm not, it's not sort of like the pure accountability. So we found there's a big social element of this of like, okay, cool. Like we're all going to lean into, great, we know we've got to take this like, you know, we got to, you know, we're going to take this writing class. We're going to level up on this. It's like, okay, great. Well, why don't you just get a cohort of, I don't know, it could be 20, 50, 200 people and we're all going to do it together. There's like real camaraderie around that.

• 1:21:23Logan Bartlett?

  Sure.

• 1:21:24Speaker 02

  Yeah.

• 1:21:24Logan Bartlett?

  On the writing side, like, is there anything that in, in, in studying this and turning it into an actual practice? Is there anything that's been particularly interesting or anything that, that you would impart on people listening about like business writing and the style and not the five paragraph essay that you alluded to? But like, what's been, what's been perhaps interesting in turning this into an actual program?

• 1:21:47Speaker 02

  I think the two biggest ones are, one is getting people in, you know, just getting yourself in the habit of writing down your thinking more often. You know, so we have a norm internally, uh, you know, that it's like, nobody wants to go sit through like slides for 45 minutes. And by the way, it puts a lot of, uh, it puts a lot of pressure on the person presenting because like, God, I hope you practiced last night. Cause if you say the wrong thing, I mean, it's not written down anywhere. This is your one shot. I think that's kind of a silly way to go about like sharing ideas, especially if they're important.

• 1:22:21Speaker 02

  So one of the big learnings there was, uh, just a lot of folks are like, okay, cool. I don't actually know where, if I have a thought or an idea, you know, a lot of companies have gotten into it's like, oh, okay. Well, I'm so used to like the slide, slides being the thing. It's like, well, no, no, actually, why don't you write down your thinking first? And actually even stream of consciousness is fine. A lot of people get very nervous, you know, it's kind of a blank canvas problem of like, well, if I start, you know, if I write this down, it may not be very good. And it's like, well, actually it doesn't matter. Like just, you know, it's a little, just get draft one done. And then the editing process is actually a lot easier, right? I mean, it's what makes it better, but your ideas will be out there and then yeah, we can, you can get feedback, we can harden them. So one is just building this into your ideation or your like thing, but hey, I have this thought, how do I do that?

• 1:23:04Speaker 02

  Part of it's realizing too, it's that, you know, whether you're writing it in a, you know, Word doc or Google doc or an email, it's not really different. Like you just want to spend some time and, uh, so email writing is not all that different. I mean, there's obviously like the quick back and forths, but it's not all that different. We really try to avoid the long, you know, the big essays in like Slack or Teams. Uh, I think that's like, sort of like counterproductive. You want them to have like a place, like a linkable spot. So the practice helps and the other is, is, you know, it's a little bit like that Hemingway app that's out there, but just write as if you were, you know, talking to, you know, a smart, you know, friend or family member.

• 1:23:43Speaker 02

  I think there's, there's a lot of like business jargon that floats in and folks feel like they need to include that for some reason. That was the other thing that I think was very helpful is just, hang on, just explain it, you know, it's a little bit like that Reddit, you know, explain, explain like I'm five, like, just explain it like I'm a smart person that understands this and who will ask questions. So that, those two things, the practice plus like, let's strip out that as honestly makes people a lot, I think a lot more confidence. And better. And we've gotten feedback that it's like, man, nobody's ever really critiqued my writing since like high school. The way we're doing now and for such a critical skill, it's like, okay, I'm glad you're getting some feedback.

• 1:24:20Logan Bartlett?

  It's funny, one of the, I had a boss early in my career who was a very interesting personality, but he used to make me write all of his emails and he would, he would make me print them out when he didn't like them and he would go back through and he would mark it up and strike it and it was so painful and I, I wouldn't recommend this as a learning skill, but it forced me to write very simply. And just very direct and communicative and I hated it and I, I don't want to work for him ever again, nor would I ever make anyone do that. That works with me, but it was actually a really good skill of how to send emails, how to speak clearly. I found that there's a very natural

• 1:25:03Logan Bartlett?

  desire for people to try to speak circuitously or like verbally. And it's actually just not direct and to the point. And so learning that skill, it was forced on me. Talking about eating vegetables, that was definitely eating vegetables and then maybe some eating shit as well. It was, it was not something I would recommend, but it was a really good skill to learn of like how to spend, send emails, how to communicate their thoughts clearly and all that stuff.

• 1:25:27Speaker 02

  I just, I mean, so first of all, I did, I was, it wasn't my boss, but my mom did the same thing, you know, probably from, gosh, when I was in third grade.

• 1:25:34Logan Bartlett?

  It's kind of your boss growing up.

• 1:25:35Speaker 02

  Yeah, very much so. Yeah. But no, I mean, it was, it was, you know, you print it out, you'd hand it to her and she would go through it and edit. And yeah, I think, look, a lot of this stuff, we talked about the craft of whether it's writing or otherwise. You know, it's this, this obsession about details and you know, a little bit knowing like when, you know, when you're kind of over the line or sort of in mission returns. I think that's the magic. I think a lot more people, uh, you know, when you talk about honing skills, you know, something, something we try to do is it can feel, I think folks sometimes say like, ah, it feels like a little bit like micromanagey, like you're too much like kind of in the weeds. But I think for some of these core skills, everybody should have that experience where somebody's really, you know, editing your work. Um, and if you're

• 1:26:19Speaker 02

  really open to it and they're, you know, they're, they're kind of, you know, they're a master crafts person, right? Um, that's like invaluable. So I think it's something, there's a lot of this stuff that, uh, I mean, recruiting is maybe another good example. Like, I obsess about the way that we interview people. And, cause I had this experience, you know, the first job, you know, I remember being kind of thrown in the deep end about like, hey, Andrew, uh, we need you to interview some folks. So here, just, you know, figure out something to ask some questions, ask them in here, go get in a room and go do it. And being like, my gosh, this is such an interesting situation. Like I've gotten, like, I don't have any experience on this. I've gotten like no tips and we haven't role played this or practiced. It's just like, go do it. And, you know, I think, you know, I probably was not very good for a while. I think a lot of these things, you get a

• 1:27:04Speaker 02

  lot better if you have somebody that's like really going to put you through your paces. And, uh, you know, look, I mean, obviously you look at things like sports, um, you know, you watch all like the kind of behind the scenes things and you look at how much they just obsess over, you know, it might be the angle of a pitcher's arm or like, you know, the way, you know, I don't know, the way a football lineman blocks. And it's like, yeah, why don't you do the exact same thing, you know, but in business and yeah, whether it's writing or otherwise, I think it's just a super important thing for folks to, you know, hopefully everybody has an experience, you know, maybe it's not as harrowing as yours, but like you should, everybody should go through that, like kind of like that, like that line of fire.

• 1:27:41Logan Bartlett?

  Yeah, there's, there's, there's something about like, uh, I don't know what it is, but enjoyment of the process or the inputs into stuff that is true. And if all you focus on are the outputs, you're going to drive yourself crazy in pursuit of, of those. And it's all the little. Things that add up to the totality of successes or not along the way. So it's an interesting kind of meta meta point as well. I guess on the recruiting side, like, what what have you learned about interviewing or setting up the recruitment pipeline? And in all of the things around that, that might be interesting.

• 1:28:20Speaker 02

  First, when we started hiring folks to join Klaviyo, I remember my batting average of the first six people I hired, I think like, I think one or two lasted three months. You know, some decided it wasn't right for them, some it wasn't right for us. And I remember thinking it's like, my gosh, this is such an expensive process. And to be so wrong is like killer. It's just so inefficient.

• 1:28:46Speaker 02

  So I talked to, I'd met somebody who was in recruiting. And they they gave me this book. I think the author's name was like Smart. And it was, I think it was a book was called like Top Grading or something like that. But it had this very like systematic process about how to do recruiting. So set aside the operational side. One of the things I loved was there was a line. It was like, look, the purpose of recruiting is if you want, it starts by defining what is the what is the job? And I think that's honestly like something a lot of folks don't always do. So a norm we have inside of Klaviyo is, you know, before we even start recruiting for somebody, you say like, okay, let's spend some time and figure out like, if we hire this person, what is their mission for the next, you know, year? Like, what does success look like?

• 1:29:30Speaker 02

  And let's be really specific. Because at the end of the day, like, an organization, a company, it's like, it's a machine, right? And there's everybody's playing their role. And it's like, okay, well, what do I need this this person to do? And I think the more specific you can get, you can do a better job of vetting for that. So one is we try to be very specific about that. And we'll kind of debate it out, right? Hey, is this responsibility, you know, this person's responsibility or is it belonging to that other team? So in really figuring that out and like, how much progress do we want to see made? And how do we think we're going to go about that? So defining that matters. And then the other thing I took away was if you can get it right 80, 90% of the time, you are like, like, that's the gold standard.

• 1:30:10Logan Bartlett?

  Oh, yeah.

• 1:30:11Speaker 02

  So it's not, you know, I've seen folks like, well, I need 100% of my hires to work out. And it's like, no, no, that's not right. Like, it's, it's, it's, you know, it's impossible. You know, this is a little bit like baseball, right? You know, 300 is a good batting average, right? So if you can bat 80, 90%, that's a good number. And then we just measure against that. So that I think helped a lot. The other thing that was a little You measure against people's success on the hiring side? Yes, yes, yes, yes. And I think one thing is actually the 80, 90% really helps with is especially for folks that are that it's, I don't know, the first time being a hiring manager, or maybe if it's like, you know, a lot of people take a lot of ownership over their, over their success and their perfectionists.

• 1:30:53Speaker 02

  Side note is we have a saying inside of Klaviyo, it's like Klaviyo is a terrible place for straight A students because you're going to get some Cs and Ds and like, it's how you figure that out. So anyways, but the 89% paradigm really helps because I think people were afraid to acknowledge like a mistake. Hey, this didn't work out. If folks have been through it before, they're like, okay, gosh, this just isn't working. And you know, it's, it's, you know, it's, it could be, you know, it could be we didn't find the role. There's all sorts of failure modes, right? Like a person's not working out, like team structure, anyways, not right. But acknowledging that and then resolving that really matters. So it's hard because if you ask people to kind of self grade, like, are you, I mean, obviously, everybody will fit to the test. But just giving them that buffer that it's like, okay, well, things shouldn't always work out. Like, so let's just be really honest with ourselves about what's going on.

• 1:31:36Speaker 02

  The last thing on recruiting is I think the experience of like a candidate really matters. So, you know, we have this value inside of Klaviyo about being customer first, which is all about, you know, put yourself in the shoes of the customers. In this case, somebody that's joining the company and, you know, work backwards from there. I had this experience that first company I joined, amazing company. One of my big lessons from them was they hired me on campus. And so, you know, the way college recruiting works is often, you know, it's, it's your senior year. A lot of the recruiting happens early in your senior year. So you've got, you know, you, you might go do the interviews in September, October, and then you have six, seven months before you actually graduate.

• 1:32:15Speaker 02

  And so you get this job and you're like really excited, you know, because it's kind of like, you know, a little bit like you're picking your next team. And you're, you're proud of it. You want to show it off. And so they did a really smart thing, which is like, great, we're going to send you some swag. And I was like, that's awesome. Like, because whatever you send me, like, of course I'm going to wear it around. And then like, I'll be your free billboard, right? But they made this huge mistake and They sent me this like double XL jacket. I was like, well, this thing, I'm like swimming in this thing. I'm like, of course I can't wear this around. And I'm like, oh, what a like painful mistake on a detail. So when I think when it comes to like recruiting brands, I think that experience of like how you, you know, get somebody excited about a company, you know, all the way from when they first learn about it, all the way to like when they start.

• 1:32:59Speaker 02

  It really, really matters. So we have this norm like, I'm like never miss size the like swag that we send people. In the early days of Klaviyo, I don't think we tell folks like you can't, you know, I mean, nearly could afford recruiters or anything like that, like internal or external. So you had to go do all your own work, you know, so I had this norm of like, I need to get people excited about. A lot of the cold emails I wrote, if they weren't to customers, were to candidates to get them excited. And I had this process of how am I going to get somebody so fired up that they're going to be excited to put in time to interview with us? And so I had this coffee shop that was around the corner. And this whole playbook about like, all right, you know, I would invite you and say, hey, I've seen some really great stuff, some work you've worked on.

• 1:33:43Speaker 02

  I'd love to chat. I was willing to like, I will come to you. So you just tell me where you work and I'll meet you at the coffee shop outside. Or I've got this spot and I'll meet you there anytime you want, right? I was very, very open. And folks, you know, almost always be like, no, no, I'll come to you. That's fine. And I have this whole strategy around like, okay, well, how am I going to ask them about like, you know, what they've worked on, learn a little bit, like, is there a good fit here? But also, you know, kind of correlate the work they've done to what we're doing and really customize that. So this idea, like this idea of getting people excited about what you're doing, and that was very one to one. And now we have more ways we do that at scale. I think is super underdeveloped. You know, one of the questions I have when I interview somebody that's going to be building a team is tell me about how you, you know, one, great folks you've hired, but also two, how do you go about sourcing folks?

• 1:34:29Speaker 02

  And if somebody tells me like, well, I wait for the hiring manager to show up and like they give me a slew of people and I pick, right? As if I'm at the deli counter, right? It's like, that is not the right paradigm. Like you need to put in your own hustle, like team building is hard. And so I think folks that have figured that out, like, I mean, it's not surprising, they tend to have the best. Track records of like, oh yeah, they build great teams. They hire really well. So that's another skill that we just like, you know, tell these, hey, look, I know this is expensive, but yeah, I mean, if you're a manager, like 10, 20% of your time is just on, I mean, just getting out there in the community and hiring.

• 1:35:01Logan Bartlett?

  Does the person that makes the decision on hiring, are they also the person that assesses the success? There's, there's some principal agent problem about, you know, if, if I signed off on the person, I might be more biased to try to give them longer rope. So that it doesn't hurt my performance ratio of my hiring success. Or is that done independently?

• 1:35:21Speaker 02

  Yeah, it's a good question. So we, uh, so, uh, it's a little bit of both.

• 1:35:25Logan Bartlett?

  Yeah.

• 1:35:26Speaker 02

  You know, I think that's, it's a hard problem to solve. It's a little bit where like the, the kind of, I don't know, the entrepreneurialness of like, I mean, you are asking people, that's why the eight or the 80%, 90% kind of helps. Cause you want to give people buffer for, hey, like, okay, like devil's advocate, let's say things aren't going great. Like what's the thing? You know, I'm known for inside of Klaviyo is like, I work on being a little more positive, but we're very quick to be like, okay, cool. That was awesome. Let's celebrate that. But then like, okay, what are the ways this could fail? Right? And we do that for projects, for teams, we do it for people. Like when I'm giving somebody a review, I always, you know, I look at it like, look, I want you to be the best you can possibly be.

• 1:36:03Logan Bartlett?

  Yeah.

• 1:36:04Speaker 02

  And so therefore these are some things that like, maybe they're hard to hear or not, but like, if you, if you advance, you know, the ball on these dimensions, you're going to be even better. Than what you are today. It's like, let's, let's, let's, here's a, how do we build a plan to go do that? That's a lot of the best feedback I've gotten has been from, you know, having folks, you know, advisors, um, you know, folks on our team give me that kind of like, yeah, hey, you'd be better if. And so we try to do the same thing. And then like, I think if you do that, you can kind of figure out like, okay, like are some of these, you know, if somebody's like kind of not working, oftentimes I find when we have that conversation, sometimes you can unearth, it's like, oh man, there's like a big kind of, there's maybe there's a big issue there. Okay. So what are we doing about it? Helps us like dig into that a little bit.

• 1:36:44Logan Bartlett?

  Once people come in the doors, there's the the element of onboarding and and culture and and all of that. And we talked about the different layers of individual contributor manager, manager of managers and all of that. Culture is kind of the other side of of the the coin or the way that you espouse or codify some of the ethos that the company is going to be and what's what is culture is what is done when people aren't watching or whatever that phrase is. What we we've talked about some of the cultural premises that you guys operate on. Are there other things that you've you've learned about?

• 1:37:26Logan Bartlett?

  Not not specific cultural elements of Klaviyo, but building a culture and and having it manifest throughout an organization and some of the benefits that come along with it?

• 1:37:36Speaker 02

  Yeah, one of my beliefs is culture is a product. And we say that because you can think of culture as like you can either be intentional about it, like a product, or you can just kind of let whatever happens, happens. So we say, no, culture is a product, we're going to be intentional about it. The other thing that happens with products is the goal is not to say, you know, you go talk to customers about what products they want, but then you have to, you know, you have to build the product that actually solves their problems, not necessarily what they ask you to build. I think it's very important. I think that the two biggest, the two biggest failure modes I see with culture or like, you know, inefficiencies is one, not being intentional about it. You don't have a roadmap the same way you would with a product. And then two is overfitting for, hey, well, this is what I'm hearing, you know, from surveys we run, et cetera.

• 1:38:21Speaker 02

  And then just literally taking verbatim, like, what should we do? It's like, oh, well, we should have program X and it's like, hey, let's go do program X, right? Instead, you say like, no, this is what we stand for. And therefore, like, we're going to then go build a culture program, et cetera, around it. So culture is a product. Then as part of that. Two other things that maybe we're a little pretty opinionated on. The first is when you think about like, you know, people, there's so much on values and all this kind of stuff. Two things I think people often get wrong in that. One, you know, values that a company has, and we think of those as like the way you want people to act, work, behave.

• 1:38:59Speaker 02

  Those are in support of a mission. I've seen a lot of companies where it's like, well, we kind of made them. And you're like, okay, but why'd you pick that? And the answer that I'm always looking for is, well, because that will advance our like mission. This is our purpose, this is what we're trying to solve for, and that's the reason it matters. A lot of people like lose that linkage. So I think that's very important. And then there's like, there's some evergreen things that everybody should do. For instance, every company should care about their customers. You know, it's a little spinal tappy. It's like, I think the difference there is there's companies that sort of say it, but they sort of turn the dial. It's like a two and there's companies that like turn to an 11, right? So this, we talked about this, you know, uh, hey, engineers are responsible for doing support. Like there are not many companies that, where that's a norm.

• 1:39:39Speaker 02

  And that's like one of the examples where we're trying to like, okay, how are we going to turn this up to 11 and really be extreme about it? So I think you need to, you need to figure out like, one, it's a product, figure out what you stand for. And then like what those things are, why they tie back to a greater purpose. And then turn it up to 11 and the 11 is we just think of like, what are the rituals that we have? Right? So, you know, the customer first one is like, yes, spending time with customers. You just got to show up. There's a lot of other ones about, um, you know, uh, you know, we, we highlight, we talk about doing remarkable work, high quality work. People want, people just want to rave about. Every week we highlight a project. I mean, one of the great parts about being 2000 people is there's all this serendipity of great work happening. You just have no idea it's there. Yeah.

• 1:40:23Speaker 02

  So we have this like, every week we highlight a project, somebody's done where you're just like, oh my God, that like is literally something you'd want to go home and like, tell your friends and family about. And that takes actually a bunch of work to source because it's like hard to like find those stories and get people to tell them. But building those in is like that you have rituals that reinforce those. I often think like, when you talk about folks and you say, oh, XYZ has such a great culture. And you say, well, explain it. They'll always explain it through examples. Well, here's an example of when or here's a ritual that we have. So I think if you do those things, like that's, that's kind of the path to, you know, really defining it and treating it like product.

• 1:40:59Logan Bartlett?

  Building a company in Boston, obviously Boston's had a ton of successes over the, the years. But there's this element of, of companies outside of Silicon Valley and New York and Boston, I think suffer for elements of this. Maybe less so now than they have in the past of just, uh, and it's certainly true of companies that I've seen in Atlanta or, or Raleigh or Denver, or whatever it is. Where when you're at the scale you guys are at now, it's when people leave and they talk to their coworker or their, their friends and families and all that. Like you guys are in rarefied air in general, right? But certainly in the Boston ecosystem now, there's Wayfair and there's HubSpot and there's, you know, other, other PTC or whatever it is.

• 1:41:42Logan Bartlett?

  But like definitely rarefied air, but I, I can tell that your ambition of where you, you want to take this is nowhere near what the business is today. When you're in the Bay Area, there's, there's, or even Seattle, there's trillions of dollars of companies in equity value. And, you know, if you're not at OpenAI right now, probably in the Bay Area, everyone else is sort of like, oh gosh, well, we're not the cool kids or whatever. But I assume a lot of your employees are the cool kids for, you know, if they're, they're, they're friends and all that. How do you maintain, how do you use Boston to your advantage or that culture? But also maintain the ambition of, no, we want to be a hundred billion dollar business. We want to be whatever hundreds of billions of dollars for your employee base and have that manifest all the way through.

• 1:42:27Speaker 02

  Yeah. Um, well, so I mentioned this, you know, having this mentality of, you know, the progress bar is always at 1%. And I think that you got to think about, well, what would it mean to be 100, what was 100x where you are?

• 1:42:40Logan Bartlett?

  I know you like abstractions, like higher and higher abstractions.

• 1:42:43Speaker 02

  So, and it's, it's interesting. I think one of the things that happens to a lot of companies, uh, after, you know, there's always this kind of like existential dread when a startup company starts of like, oh my God, we're not going to make it. And you know, I'd say there's a little bit of this like, you know, thing that happens to for some companies. It's like, oh, this, you know, it's a fundraising round or it's going public, but it's these kind of artificial moments. And I think what those often, what those can expose is, is there this greater ambition? Like, do you have this point of view of like, hey, in five years, 10 years, we could be, we could do this. You know, for us, it's about being this like scalable brain, the scalable interface, you know, way that any business, organization can interact with any consumer, right? You know, I think about all the dozens of organizations, you know, whether they're

• 1:43:27Speaker 02

  a retail brands or any kind of company that I interface with. And I'm like, yeah, I want every single one of those interactions to be awesome. Like, I want to love it. And I want those companies to feel like they've got like the tech where it's very cheap and easy for them to like go deliver that. So you gotta have, I think you gotta have that ambition. I think that just, actually folks just gotta step back and, you know, you just gotta think it through, right? A little bit like our five-year plan thing. The other part is, it's interesting, like we've, I think there's a lot of value to like, brand PR, especially when it comes to like, you know, employees. We have taken a tact of humility matters. And so in some sense, it's if you believe in what you're trying to build

• 1:44:11Speaker 02

  towards, and that's the exciting thing. And you're kind of like, you're shoulder to shoulder with other people to care about it. You're, you know, getting in there with like the people that are actually the users, customers, partners. The rest is kind of just noise. And it's fun noise, don't get me wrong, but it's kind of just noise. You know, for a lot of years, Claudio, we didn't, there wasn't, well, we didn't have a PR function, but we just didn't do much press or really anything. And it's interesting, because I always had this kind of like double point of view about it, where I was like, ah, kind of lamented, because you're like, ah, it's not like there's just, everybody's like lining up to, you know, interview and all this kind of stuff. But at the same time, we built an awesome team.

• 1:44:50Speaker 02

  And a team that was very committed, you know, to each other and towards what we wanted to build. And I, I think when companies get more successful, it, there's actually this real risk that all of a sudden it's like, well, there's folks that want to join just because it's the cool thing. You know, I had friends that, uh, you know, went to the Bay Area and, you know, when I talked to them about like, oh, so what's going on? Like oftentimes they talk about, it's like, well, here's where the cool thing is. And I'm trying to decide if I should join it or leave it, but it was very like, you know, every 18 months, every 24 months, there was a new thing.

• 1:45:21Logan Bartlett?

  Yeah, ephemeral.

• 1:45:22Speaker 02

  Yeah. And I'm like, that's exhausting. Don't you just want to like build towards something? I mean, like, look, if something's not working, sure, like go, you know, of course, like you can experiment different things, but it feels exhausting to play this kind of like social game of like, what's the most exciting hyped thing right now? And you know, again, like a lot of it's, I mean, a lot of these great companies, I mean, they're, they're real, like OpenAI is a real, that's real tech.

• 1:45:44Speaker 02

  But it's like, but the reason to join is because, you know, let's say, I don't know, if the mission of theirs around like, you know, uh, you know, LLMs and AGI, then great, join for that. But, you know, do the mental thing of like, well, what if that whole thing, you know, I don't know, what if, what if things don't go as well as planned, right? What if, I don't know, GPT-5 takes a lot longer to build than we think, like, would you still do it? And if your answer is no, then like, well, gosh, maybe that's not the right place to do it. So I, I think actually it's gotten harder for us to recruit. Because it's a constant check you have to run of, you don't want to be the, I mean, some, I'm like, we don't want to be the cool kids. We want to be like, we're here to do our thing. And it's sort of, I often try to, you know, how do, how can I sell against that? Ah, we're actually not going to be a cool company.

• 1:46:30Speaker 02

  In five years. And that's like, gee, would you still want to be here? Cause if you do, then that's probably a good fit. If you don't, then like, I'll save you some time, right? Go try something else.

• 1:46:36Logan Bartlett?

  Interesting. I was curious about, you've talked about productivity as software versus output as software. And I assume moving more to artificial intelligence and that we're going to move less on the pure productivity and more on the, the outputs. But I guess, was that actually a founding tenant of Klaviyo in the early days?

• 1:46:55Speaker 02

  Yeah. I mean, like I had a, um, you know, I, I mentioned that, so I've worked, I think, you know, if you're, if you want to be a founder entrepreneur, right?

• 1:47:04Speaker 02

  I think there's a lot of mythology around, oh, I had this idea and the media does not help with this. It's like mythology around like, I had an idea, I like dropped everything, quit my job, dropped out of school, started working on it and it just poof worked. Lightning struck. Yeah. I mean, the reality is if you talk to almost any successful entrepreneur, founder, they'll be like, oh, my God, it wasn't the first one that worked. It's like, are you kidding me? I've been experimenting with ideas for years. Right? So for me, I mentioned, it's like, okay, so I did a little bit of that experimentation inside of other companies, but you know, then nights and weekends I was working on other stuff. And I had this, um, so I'm a pretty big runner and I, you know, one of my pet peeves is it's like, there's no great search engine for finding 5Ks and marathons and this kind of stuff. It feels like there should be, but there's all these like very old websites,

• 1:47:49Speaker 02

  like, uh, early 2000s era. So it's very hard to filter. So, um, anyway, so I had this idea of like, oh, I'm going to build a search engine for that. And then I'm going to, you know, maybe I can get some of these races to advertise and like, that could be a business model. And so while I was playing with this, I, uh, you know, I would, I made a list of all these like little local 5Ks or, you know, maybe it's like, we're, you know, we're here in New York, it's like New York marathon, the Boston marathon and like to talk to the big, big events too. And I was doing all these calls and anybody that's, you know, look at anybody that's been on a sales, sales team, BDR team has done the same thing, right? And do all these discovery calls. And I'm just going through one by one by one. And I was like, this is insanity. I like, I more or less have my playbook. Like, I know the kind of things, questions I want to get. Like this ought to be the kind of thing that like, I want to provide a good experience to somebody, but like, I do not

• 1:48:33Speaker 02

  need to be doing this myself. I can't send them a form because it's way too impersonal. I'm like, why can't I, like, why isn't there a way for me to just take a part of myself, clone it and be like, look, I want you to go talk to all these people, like maximize for whatever we're trying to solve for. In this case, maybe it's information gathering or whatever. And, uh, but I want it to feel very human. Like, I think we're not far off from, you know, when you, you know, somebody could call, call, or you could do a Zoom and it's like, it's not actually me there or you. It's like our surrogate. It's our like avatar, but it is us in terms of how we think and how we want to act. Um, and this is certainly works for a business where a business effectively like, well, there's no one person, right? A business, you know, they write these training manuals on, this is our.

• 1:49:14Speaker 02

  This is, this is, these are our brand values. This is how we behave. So, but I think that can get encoded in software. And I think when you do that, what's, what's interesting is you're like, well, how would you know if it's any good if it's being successful? And it's like, well, if you can measure some output metric, I mean, all of machine learning is based on this idea of like, there's some reward function output metric that we're like trying to maximize for, right? We're fitting our regression to or whatever. I think if you have that, I think we're not far off from having software that you can say, look, I don't want to treat this as like user goes in and just, you know, put packs at the buttons based on what they think is the best way to maximize for whatever they're trying to solve for. Just have the user declare what they're trying to solve for, and then like the software should just run itself.

• 1:49:56Speaker 02

  And I have been a very big believer of that for like the last 15 years. You know, we definitely have a lot of the data to do that. The hard part actually is a lot of applications is finding the like, being able to measure that, you know, output function. You know, we go back to writing like, good God, like, how are you going to measure like, is this a good email or not? It's like, well, I don't know. I mean, like somebody needs to score it, label it. Now it happens like for the domain that we're in right now, um, marketing, it's much more measurable. You can measure conversions and that's much easier. But I do think that's a paradigm that's coming to software. So we're very interested in this, like, how do you do attribution? How do you do this reward function discovery? How do you then build the systems to take all of the like dependent variables and correlate those? And how can you make the machine, you know, make the software learn on the fly?

• 1:50:41Speaker 02

  I think that's very interesting. The, uh, what's, you know, the, we'll see if the L L Ms really help with this. Maybe they do, right? If they can get to reasoning. They've been especially helpful in our domain on like the content creation side, like just, you know, that, that's because that's a real part of marketing. But anyways, I, I do think that's like, you know, the Steve Jobs quote of like, hey, the, you know, the, uh, the, you know, the computer is like a bicycle for the brain, right? It's a great one, but it's really, it's like, it's, it's, yeah, it's like productivity tool. I think we're close to, because we can measure these reward functions, we now have the algorithms to do this. That like, we can discover some of the algorithms that we ourselves are using. And I think it's super interesting that we talk about learning, right? I mean, so much for us is guess and check. I think it's very interesting. It's like, my gosh, but what if you could take the algorithms we're using today?

• 1:51:25Speaker 02

  Put that in statistical software, have it, you know, then go kind of train up and learn like, maybe it could learn faster than we could. Maybe it could teach us back. You know, how to, you know, how to improve things. So I could have a business and say, this is the way I think I should treat my customers. It's fascinating. Like when I talked to a lot of brands, they're like, yeah, I think that's the right idea, but I don't know. I'm a little bit making it up as I go. What we've said, it's like, okay, cool. You tell us the ethos, what you want to stand for, and then we'll really, you know, we'll harden it, we'll optimize it. Anyways, I think we're, we're close to a lot of software doing that. And we're, one of the things we're working on is the patterns by which, you know, software of the future will be built to, you know, accomplish that.

• 1:52:03Logan Bartlett?

  Super cool. Well, Andrew, thanks for doing this.

• 1:52:06Speaker 02

  Cool. Thanks for having me.

• 1:52:06Logan Bartlett?

  Awesome.

• 1:52:10Logan Bartlett?

  Thank you for listening to this episode of the Logan Bartlett Show with CEO and co-founder of Klaviyo, Andrew Bialecki. If you enjoyed this discussion, we'd really appreciate it if you shared with anyone else that you think might find it interesting, as well as subscribed on whatever podcast platform you're listening on. We'll see you here next week with another great guest.