20VC: The Biggest Mistakes Startups Make Hiring, The 2 Reasons Startups Fail and How to Avoid Them, Why Most Startup Equity Plans are F****** and Why You Should Scrap Titles From Your Company with Eddie Vivas, Founder & CEO @ Curated

Eduardo Vivas is the Co-Founder and CEO @ Curated, a network where product experts monetize their passion and help consumers make the perfect purchase. To date, Eddie has raised over $141M from some of the best including CapitalG, Greylock and Forerunner to name a few. Eddie is also a stellar angel investor with a portfolio including Telegram, Truebill, AppLovin and Dollar Shave Club among others. Prior to Curated, Eddie spent 3 years at Linkedin as Head of Talent Solutions, following his startup, Bright, being acquired by them in 2014. In Today’s Episode with Eddie Vivas You Will Learn: 1.) The Founding of Curated: What was the aha moment for Eddie with Curated? What were Eddie's biggest takeaways from his prior companies? What did he take with him that worked? What did he disregard that did not work? What were some of Eddie's biggest lessons from Linkedin? How did it impact his mindset? 2.) The Compound Startup: Why did Eddie decide it was right to build so much of the tooling themselves? How does Eddie determine when to buy vs build? What are the biggest mistakes Eddie sees founders making when building multiple internal tools at the same time? How does build a compound startup increase the strategic value of a company? 3.) Hiring: Missionaries not Mercenaries How does Eddie structure his hiring process at Curated? Why does he not believe that startups are for everyone? What are the biggest signals that a person is a missionary and not a mercenary? How do mercenaries act in a way that is different to missionaries? What questions in an interview process show these traits? What are some of the biggest mistakes Eddie has made when hiring? 4.) Equity and Compensation: What is Eddie's biggest advice to founders when it comes to equity allocations for the team? Why does Eddie believe it is crucial to offer and provide secondaries for the team? How does Eddie feel about the amount of secondaries founders take today so early? Item’s Mentioned In Today’s Episode with Eddie Vivas Eddie’s Favourite Book: Predictably Irrational: The Hidden Forces That Shape Our Decisions

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

• 0:00Harry Stebbings?

  Welcome back. This is 20VC with me, Harry Stebbings. And today, we're joined by a phenomenal serial entrepreneur, Eddie Vivas, founder and CEO of Curated, a network where product experts monetise their passion and help consumers make the perfect purchase. To date, Eddie's raised over $141 million for Curated from some of the best, including Capital G, Greylock and Forerunner, to name a few. Eddie's also a stellar angel investor with a portfolio including the likes of Telegram, Truebill, AppLovin and Dollar Shave Club, among others. And prior to Curated, Eddie spent three years at LinkedIn as Head of Talent Solutions, following his startup, Bright.com, being acquired by them in 2014. And I do also want to say a huge thank you to Kirsten at Forerunner, Leila at Capital G and John Burbank for some amazing question suggestions today.

• 0:44Harry Stebbings?

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• 1:28Harry Stebbings?

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• 2:10Harry Stebbings?

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• 2:55Harry Stebbings?

  AngelList handles your company's incorporation, banking, cap table and fundraising processes, all in a single place. This allows founders to focus on building. If you're a founder, you can launch your company at stack.angellist.com/20vc. Whether you're a founder or a funder, you're in great hands with AngelList. But that's enough from me. So now I'm so excited to hand over to the one and only Eddie Vivas, founder and CEO at Curated.

• 3:25Speaker 01

  You have now arrived at your destination.

• 3:28Harry Stebbings?

  Eddie, this is such a joy to do. As I said, I heard so many great things from John Burbank, from Leila Sturdy. So thank you so much for joining me today.

• 3:36Speaker 02

  Excited to be here.

• 3:37Harry Stebbings?

  Well, I want to start, I always love a good story, Eddie. So how did you make your way into the world of startups? And then most recently, how did you come to found curated? Let's start there.

• 3:45Speaker 02

  Sure. So my journey into tech was a little different than most. I dropped out of high school, which didn't go over incredibly well in my family, as both my parents were first-generation immigrants and doctors.

• 3:55Harry Stebbings?

  Can I ask, sorry, I'm going to interrupt you. How did you get that through to them in a way that they would accept?

• 4:01Speaker 02

  I didn't get it through to them and they didn't accept it. They were pissed as all hell. Yeah, we got into a big disagreement. I held my ground, they held their ground. And so I grew up in this small town and I moved to Miami to go live with my grandparents. And my whole family was like, essentially like, had cut me off, which was the right decision in hindsight, obviously. And so I spent the next three years. Working in a warehouse packing boxes. And then I woke up one day and I was like, this doesn't work. This sucks. And so I was like, I need to figure out a way to make some money. I'd always been quite technical. So I started building websites. I built a recipe cookbook website and I went from making like, I don't know, eighteen hundred dollars a month to like twenty thousand dollars a month in a matter of six months. And I took all of the money that I made from this website that I had and I just kept reinvesting it. And I started my first company.

• 4:44Speaker 02

  And so that was an ad tech business, ran that business for about seven years and one day realized like my heart just wasn't in it. So we sold that company. But before we did, we spot out a few assets. One of them was called Bright, which I went to go focus on. And then another one was called AppLovin, my brother and my co-founder Adam Fergie went to go focus on.

• 5:03Harry Stebbings?

  I'm just too interested, you know, you said there about kind of packing boxes in the warehouse to making twenty grand a month and founding company, reinvesting. This sounds awful. From a small kid, I always knew that I would be successful and it's not arrogance. I just kind of just always believed it. Not that I am successful, but you know what I mean? Like, did you always believe you would be when you were packing boxes in the warehouse? Did you think this isn't me? I can do more. And did you always have that? I can be successful.

• 5:27Speaker 02

  I think I probably had more resentment early on. The system had done me wrong. And then one day I woke up and was just like, I gotta figure my own thing out because no one's gonna solve this problem for me. And so as a kid, I was always super entrepreneurial. I mean, I started a T-shirt company, designed websites for people. I always was trying to figure out a way to build my own little businesses. But there was definitely some tough years there where I, yeah, I was questioning myself as to what was gonna happen.

• 5:52Harry Stebbings?

  Can I ask, what was that transition then to founding Curated? What was that aha moment?

• 5:56Speaker 02

  Curated had an interesting path. I had been at LinkedIn for four years. I had given them nine months notice that I was gonna be leaving. And about a month into that, Microsoft acquires the company. I had this opportunity all of a sudden to work with a bunch of people that I had been working with the past couple of years. Who said, I love LinkedIn. I've been here five years, some of ten years. I love this company, but I'm not ready to go be part of Big Co. And so I had ten people who I really, really respected, who has essentially become like my founding team. And the team knew that they wanted to work with each other before we actually even had an idea. And so then I went back to what was One of the most ambitious ideas that I've ever had, but that I candidly just thought was too hard to to work on. And the idea is one that I think a lot of people have had before.

• 6:37Speaker 02

  When I'm trying to make a major decision, I wish that I could talk to somebody who knew a lot about that. Google has indexed all the world's published knowledge, but there is somebody out there that I wish I could talk to. When I'm trying to make a specific decision and I often leverage my network to do this today. I call the people that I know, but I only know so many. And so we just went all in and and the idea, the aha moment, I guess you could say that I always reference is I'm from Florida. So didn't grow up skiing much or spending much time in the snow. But 10 years ago, I used to go on this ski trip all the time with my friends once a year. And candidly, it was miserable. Like, I loved hanging out with my friends, but like I was just getting my ass kicked out there all the time. At some point, I'm like, all right, I'm gonna get an instructor, go to the top of the mountain, ride down with the instructor. We meet at the base and the guy's like, this is all wrong.

• 7:20Speaker 02

  And essentially, like, I had gone into a ski shop, bought a bunch of high-end gear because they just sold me the most expensive stuff. Me assuming more expensive is better. Turns out like that was for experts. I'm a beginner. Guy goes into a shop, rents me a bunch of like the most basic stuff. I go back out, absolutely have an incredible time. And so that was kind of this aha moment where like I wish that I would have been able to talk to somebody who would have pointed me in the right direction. And how do we help with curating to actually make that happen?

• 7:43Harry Stebbings?

  I do want to touch on some elements that pre-curated, which I think are really important, which is, you know, when we think about serial entrepreneurship today and you look at that time, you know, pre-curating the entrepreneurial endeavors you had before. What were some things that worked with them that you took with you to curate it? And then what were some things that did not work that you disregarded, having seen them not work?

• 8:02Speaker 02

  At Bright, the biggest thing that I was known for was I cared a lot, but I was very intense. We were at the office till nine, 10 o'clock at night. That was my badge of honor. Like, if you were working your ass off, I was happy. And I thought that like being late at the office meant creating impact. And it turns out like, not really. That's just a quick way to burn out people. And the people who stick around will end up just being the people who aren't your stars in the first place. Because your stars want to be learning and they want to be happy and they want to be creating impact. So I'd say that's probably the biggest thing. It's just a much longer term focus, right? Like, I'm not worried about the next month. I'm worried about the next year. I'm worried about the next 10 years. Worried more about building. Right foundations.

• 8:40Harry Stebbings?

  I do want to ask, when you think to like the serial entrepreneurship, I had Joe Fernandez, a founder on the show before, and he said that serial entrepreneurship is overrated. Would you agree with that, having had many lessons in entrepreneurship and others before?

• 8:52Speaker 02

  I disagree. So a couple of things. When I invest, I very much look at failed entrepreneurs. I think it's incredibly humbling. I think anybody who's, I think you go into building your first startup thinking all the stuff that you read on the internet about how great it is and how easy it's going to be. And the reality is it's really tough. I think one of the benefits of being a serial entrepreneur, and it's very much a luxury, is you're given the benefit from an investor that you'll figure things out. So you can approach things with a much longer term mindset, right? I'm not worried about like, do I hit this number this month? I'm worried about like, am I on the right path towards the big outcome? That difference between being able to be long-term focused versus short-term focused is a huge, huge, huge advantage. I always tell entrepreneurs, like, don't take this advice from me because what I do as a repeat entrepreneur is different than what you're going to do from somebody who's just getting started. But I think serial entrepreneurship is a big advantage.

• 9:36Harry Stebbings?

  Is it difficult to create a sense of urgency with long-term focuses? I like that kind of go slow to go fast, you know, you go far or you go fast. I love all these things. But you also do need to create interim velocity and execution. How do you think about having that long-term mindset, but also creating a sense of urgency within the team to execute on plan?

• 9:55Speaker 02

  We're going after something, at least with Curated, that's really ambitious. And that's about going slow. It's about doing things the right way. Because we're doing something in a place where a lot of people have failed in the past because they didn't actually build the right foundations. And if you scale a business that doesn't have the right fundamentals, you're either just going to raise a ton of money in a hope that you get yourself out of that hole, or you're going to blow up eventually anyways. So it's less about going slow. It's more about like building the right things to actually build a sustainable, strong business.

• 10:21Harry Stebbings?

  Sorry, I'm going to interrupt you. How do you determine the right things?

• 10:24Speaker 02

  The right things are, what are the things that you have to get right for your business to work, right? There's a lot of things that are nice to haves and there's a lot of things that are must haves.

• 10:31Harry Stebbings?

  What are the right things for you?

• 10:33Speaker 02

  For Curated, the thing that we learned was if you're coming to us to be able to chat with an expert, we need to make sure that every time you're connected to an expert, they're an incredible expert. And that's actually quite a hard problem because we'll receive a hundred applications and we've learned we can only really accept one. We have to vet somebody on technical competencies. We have to make sure. They're a strong communicator. We need to make sure that they're actually reliable and available. The amount of tooling that we had to build, because we had, we learned, we don't know who a good expert is. Our experts know who good experts are. So we had to build a social hiring platform. Then we had to build a platform to figure out, okay, well, how do we measure the supply and demand of when customers are coming in? And when we're going to schedule experts? And how do we determine which experts get which time slots? Because not all experts are created equally. Some are better than others. Because when you come in, we like to, we call it a real time connection rate.

• 11:16Speaker 02

  Ninety five percent of the time, we're connecting you with somebody in under a minute. There's just so much infrastructure that has to exist. When you, when you look at curated from the outset, you're like, oh, this is a simple site. I just chat with somebody. But there's really like seven SaaS companies worth of technology that we had to build to get this, the experience to actually work.

• 11:33Harry Stebbings?

  Would you say you're building what Parker Conrad says, a compound startup? One, and two, how do you determine between buy versus build? Bluntly, the joy of inventing in today is you can buy a lot. Why did you feel the need to build so much?

• 11:47Speaker 02

  We tried to buy wherever possible. The challenge for us is we have a very B two B approach in a B two C business. When you chat with somebody at curated, that expert has their own phone number. They have their own email address. That's the way you would think of like a B two B company selling SaaS software. Like all the tools that are out there were I chat with Curators as a company, not I chat with Kelly or Jack who work at Curated. And so all of the tooling was just going to be slightly off. One of the things we've come to terms with is if I stack a bunch of ninety percent solutions on top of each other, it gets really mediocre really quickly. It feels like I'm making just a small compromise with the first, but I'm actually making a lot of compromises. It really depends, is this thing nice to have or must have? There are certain things I have to get right. And for the things I have to get right, you should build them.

• 12:29Speaker 02

  And for the things that you need to get right, then it's a matter of like, if you have to build, then great, but otherwise absolutely buy. And we definitely went into this expecting it would take half the time to build everything. The benefit is if you've built everything and you've built it the right way, then all of the toys play together really nicely and you can do some really cool shit.

• 12:46Harry Stebbings?

  I totally agree with you and you build real strategic value in any case of an acquisition that is attractive for any incumbent. We're going back to the right things. I cut you off there when you said, you know, determining nice to have versus must have. There are any other elements that are crucial in determining the Right things.

• 13:00Speaker 02

  The nice to haves are often things that are shiny but aren't core to the success of the business. So in the challenge with this, you don't really figure out those things until multiple years into your problem. My old boss, David Thacker, who led our series B, used to tell me startups fail for one of two reasons. They either scale before they find product market fit, or they never find product market fit. But it's all not with time. And so what's the nice to have and must have? Unfortunately, the real answer there is it just takes time to figure those things out and then to become obsessed with just solving those problems and having a ton of clarity. Because the biggest challenge that most companies have is they've just spread their resources over way too many things. And there's people constraints, there's capital constraints, and you don't get to focus the right amount of energy on those things.

• 13:44Harry Stebbings?

  Would you say you have product market fit today with curated?

• 13:46Speaker 02

  Absolutely. If I always tell people, if this business doesn't work out, it's because I messed up. It's because basically we accelerated too fast and blew the plane up midair. When you read our reviews online, they almost look cooked or fake.

• 13:57Harry Stebbings?

  How did you know when you had it? One, two, I'm too intrigued. I know you, you're an analytical guy. How do you determine the ways that you could fuck it up?

• 14:05Speaker 02

  So it was a couple of things. So some were data driven and some were gut intuition driven. On the analytical side, it was just purely that our conversion rate was so high, right? When we connected somebody to an expert, they just converted at such a high rate. It was the fact that it increases conversion rates, it decreases return rates. So a big challenge in e-commerce is return logistics. Our return rate is between one and two percent, meaning people shipping the items back. So that's a huge benefit to us. And then the third is that from our second sale, we had consumers reaching out to us saying, I'd like to tip my expert. And so half of expert compensation is actually covered by the consumer via tips. When somebody goes and says, hey, this is a nice thing in terms of ratings and reviews, that's one thing. Another thing is when 90% of consumers are going and tipping experts.

• 14:47Speaker 02

  On the gut side, again, just observing these conversations that were happening. And one of the things that we saw was when you bring someone together or people together who have equal passions, one party respects the other one and one's actually looking for advice from the other. Just these like very magical things happen, like it's actually a very enjoyable experience. And so our experts love the work they do, not to criticize Instacart or Uber, but if you think of a spectrum of. Like I work in a good economy or passion economy. One is I'm delivering a good or a person somewhere. And the other one is monetizing my passion and my knowledge and I'm teaching somebody something. People very, very, very much prefer focusing on the things they're passionate about. The fact that like people were having these amazing conversations, experts were making money, talking about the things they loved. Our retention rates were so high.

• 15:30Speaker 02

  It's a combination of both analytical and intuitive, but we knew from very, very early on that we had a good business. The challenge was that magic moment was happening like 20% of the time. Because it was taking us 30 minutes to connect you with an expert or we were connecting you with the wrong expert. Or we weren't bringing in the right type of consumer. And we spent the last couple of years really dialing in and building all the infrastructure to make that happen in a repeatable manner. And now we're in a place where we're very much ready to scale.

• 15:56Harry Stebbings?

  Tell me, when we said about kind of how one could fuck it up, I'm most worried bluntly about companies raising too much money too soon. Not having repeatable playbooks and then scaling pre-product market fit, hiring a ton of people, having shit culture because they've hired a ton of people that fail, hate it and churn. How did you think you could fuck it up?

• 16:15Speaker 02

  By exactly what you just said, right? Like literally you just dictated the playbook on how people fuck it up. I worry like crazy that because capital is so ubiquitous, that you can become too comfortable and start to scale up before a business is ready and or bringing the wrong people. One of the things that I'm really passionate about hiring a team of missionaries, not mercenaries. Because I think that like you need people who genuinely believe in your mission. Because especially when you're working on a really hard problem, it's not a matter of hiring somebody who to solve, like to build this feature, this tool, roll up this program. It's somebody who's genuinely going to help figure out like fundamental problems the company has. Somebody who, when you hit roadblocks along the way, they're going to be able to weather the storm. Those people take a long time to hire, like they don't come quickly.

• 17:00Speaker 02

  Fucking it up for me was lowering my bar on trying to like get people to join my company because we were slow on hiring.

• 17:07Harry Stebbings?

  Can I ask, how do you determine a missionary versus a mercenary? People are often very good at selling themselves. They're very passionate in the interview. How do you really determine a missionary and a mercenary? What questions do you ask? What are the Signals. What suggests true missionary?

• 17:22Speaker 02

  Missionary people ask a lot of questions about the business. They really want to understand it. I agree with you that people sell it well, but people often reveal their cards pretty quickly too on what actually matters to them. One of the things for us is our compensation model solves for a lot of this. I'm a very big believer that if you're gonna go join a startup, you should be focused on equity. And so the people who are equity focused are already more missionary focused than the very much more cash oriented people. And I tell people, if you're trying to solve for cash on a risk adjusted basis and you want stability in life, you should go to a FAANG. Like VP at a FAANG is the most sustainable way to make considerable amount of wealth. Startups you should go to because you want to have happy, right? And maybe, yeah, sure, there's upside, maybe the thing works out. And if it does work out, you should be incredibly vulnerable. The compensation model solves for a lot of it.

• 18:06Harry Stebbings?

  On the comp model, sorry, but if I'm a startup founder and you're invested in me, how should I literally structure my comp model then, given what you've just said?

• 18:14Speaker 02

  Be incredibly generous with people on the equity side, right? There's nothing, in my opinion, that's more fucked up than when a company gets acquired and you find out that the team just owns such a small percentage of it. If your team are large equity holders in the business, your problems are now their problems. We've got to figure this thing out together. It's no longer just Eddie's problem. And it's hard, right? Because people talk about how competitive the market is and how people are churning a ton. I mean, I don't want to jinx myself. I think we've lost one person in the last 12 months, right? And we're 135 people. I think over the course of the history of the company, we've lost less than I can count on my hand. And a large part of that is, is we don't hire mercenaries. We really make sure people are bought into what we're doing. I sure as hell don't try to sell them on the company. I'm like, let me talk to you about all the things you're gonna run into and all the challenges.

• 18:58Speaker 02

  Isn't this gonna be hard? At times, it's gonna suck. It's also gonna be really fun. But it's only gonna be fun if you really believe in what we're doing. If I'm starting a company, like leaning heavily into being generous with people on the equity front, be thoughtful about conserving capital because things always take longer than you think.

• 19:12Harry Stebbings?

  You've got two founders in my metaphorical startup. What does being generous with equity, like, what does it actually look like?

• 19:19Speaker 02

  Well, irrespective, if I'm founding a company, I'm a really big believer in equal partnerships. I actually don't like the idea of, as much as possible, I don't like the idea of the CEO having always the largest amount. I always think that means you brought in somebody who you don't believe is equal to you. Broader speaking, like, we just look at comp data and we go 99 percentile on equity and we lean in there.

• 19:38Harry Stebbings?

  Have you made any mistakes when it comes to comp plans?

• 19:41Speaker 02

  Good question. I'm sure I've made mistakes. Yes, I'm sure, but I can't think of any of them right now. I mean, I think that we may have been slightly too conservative, but I'm a really big believer that startups aren't for everybody. And if you try to make them for everybody, it makes it for those who it's really good for, not as good. If that makes any sense, you're like watering it down. I think in my past, I was very cash focused and I learned that like, people only cared about the next month's paycheck versus today. It's by getting people to really fundamentally care about the health of the business and I just think that's better.

• 20:11Harry Stebbings?

  How do you feel about transparency? Should everyone in the team know how the company's doing?

• 20:14Speaker 02

  Yes, because, and so here's why. If you hired smart people, they're going to figure the shit out of it anyways. You can hide things from dumb people. Smart people are going to figure it out. So you might as well be straight up with them. And because if I have a sense of urgency behind certain decisions, it's because, hey, here's so much cash we have left in the bank. Here's where we're progressing towards numbers. If they understand we're doing well or we're doing poorly this month, this quarter, they have context on decision making, they're going to change their decisions accordingly. They're going to think about spending capital differently. And so I'm a really big believer in transparency. I think you can fool mediocre teams, but smart people always will figure your bullshit out.

• 20:47Harry Stebbings?

  Have you made mistakes in hiring before and how did those mistakes impact how you hire today?

• 20:52Speaker 02

  I made a ton of mistakes hiring. The biggest mistake I've made in hiring is trying to convince people to join us. And I think it's that if I sell the dream and I convince you to come, and inevitably the dream doesn't come true, you're going to be demoralized. You weren't really that bought in in the first place and you're not going to be that high of an impact. That's probably been my biggest learning lesson. My second learning lesson, and I think that everybody builds this gut intuition over time, is sometimes you just have to trust your gut, where there's a few yellow flags about somebody. And just because they have incredible pedigree doesn't mean they're the right person for you. But I think that the first is probably more important than the second. The second is, and sometimes I'm wrong, by the way. Sometimes I've taken risks on people and I've been like, ah, I'm not sure. And they actually end up being great.

• 21:35Speaker 02

  I do think there's a, I'm a really big believer in the, if hiring slow, really making sure that this makes sense for both the person and for us. Cause if it doesn't make sense for either, here's where things really go wrong, especially at a startup, when you lose people, it really impacts the morale of the team. And you can lose a few people and it's okay, but if you start losing quite a few people, everyone starts to question themselves. And like, is this business actually working? Why is this person leaving? And so I'm all about like getting it right from the beginning and making sure I trust that person.

• 22:03Harry Stebbings?

  So I agree on the going slow. I tweeted this the other day and I got quite a lot of pushback from founders being like, great idea. Bit of a luxury position you're taking. Sometimes you need to get bums on the seats and people working. Thanks for go slow, but we've got runway that's going down and we've got investors expecting results.

• 22:20Speaker 02

  I'm not sure that spending my money faster is going to help my runway, right? And getting bums in seats, like that's full transparency. Like I think that's stupid. If you're a good entrepreneur, like you don't only have to rely on metrics to convince your investors that you're making progress in the business. If you're super clear about like, here's what we're setting out to achieve, here's the progress you've made, here's where we're going. I think a big mistake first time entrepreneurs and just entrepreneurs make in general, is they're overly focused on showing progress towards vanity metrics versus building actual value in a company.

• 22:49Harry Stebbings?

  Do you think they know the difference in vanity metrics and actual value?

• 22:53Speaker 02

  The issue is that the line is a bit blurred. Everybody can generate more revenue by just burning more money, right? And so you hit X revenue goal, but what did that actually do for the business? Did the unit economics of the company actually get any better? Investors know there are levers that you can pull that generate short-term revenue. In many cases, those levers are unhealthy. So to the person that's filling bums in seats with mediocre hires to hit goals, I don't have a ton of sympathy for.

• 23:16Harry Stebbings?

  Do you not blame funding markets for that? You mentioned obviously you were angel investing earlier. Do you not blame funding markets? I'm obviously a VC and in every VC chat there is, when it's like, oh, they scaled to three million in ARR in six months. Wow. Everyone gets excited and rounds happen. Do you blame the VC?

• 23:32Speaker 02

  No, not really. I mean, I think that, listen, the pendulum is in absolutely the core of the entrepreneur right now. Capital is super ubiquitous. People want to hit certain goals because they want to puff up their valuations even higher. I think different times call for different approaches. And so this advice is not timeless. There will be times where it is completely irrelevant, what I'm saying. But right now, there is a lack of high-quality entrepreneurs and there's an excess of capital. And so investors are trying to fund whatever they can. And so to the person that's trying to hit X goal because they're trying to do six million dollars in ARR in X period of time, so they can get some silly high round number, good for them. I mean, I think that there's pros and cons to that model. I think it becomes really hard to build a high-quality, sustainable business from it.

• 24:15Speaker 02

  And I think the most important thing here, raising capital does not equal success at all, right? Like, it doesn't mean anything, actually. It just means you were able to convince some people to fund your business. But until you actually sell the business or you turn a profitable business, it's just capital being raised.

• 24:29Harry Stebbings?

  Do you get worried by the state of secondaries today? I see companies stay, raise Series Bs pre-going live, where the founder can take five to 10 million bucks off the table.

• 24:37Speaker 02

  So one thing I'm super proud about is we've offered our team a few secondaries and the take rate has been less than 10%. In one case, we didn't even have enough secondary demand to fill, to cover the legal fees. And I think strong companies and strong founders and the people who work at those companies who believe in the companies should want to keep their ownership. That's it. My, my, my thinking on this has evolved some. Life happens and if you have a very long journey, you need liquidity points. And I think as a company, for example, for us, I want to stay private as long as possible. So I want to create secondary opportunities. I don't want my team taking half of their equity off the table. But if they need to buy home or they're having a child or whatever it might be, I think it's a healthy thing for companies to be able to introduce some of that.

• 25:19Speaker 02

  But to your point, early companies, founder taking 10 million dollars off the table, personally, I think it sends a lot of weird signals.

• 25:25Harry Stebbings?

  Charles, you've had success before, though, you know, with the prior companies. How do you think about your relationship to money today?

• 25:31Speaker 02

  It's gonna sound cliche, but I think the biggest relationship that I've, shift I've had with money is that I've realized it doesn't bring happiness. It empowers you to do a lot of really interesting, cool things, but everybody kind of goes. Not everybody, but a lot of people go through life and they're like, I have this goal and then I have that goal and then I have that goal. And then all you realize is my, my goal continues to go up and that becomes a hamster wheel. And so what's more important is to actually find purpose. I love what I do and I do it for the love of the game and the love of building things. And I personally generate happiness, creating wealth for others than for myself. And that ends up being actually a really virtuous cycle because if you care about doing right by others and helping them out, then they help you out and it compounds really quickly. Money obviously like solves a lot of problems at the early onset, like financial stress sucks.

• 26:13Speaker 02

  But like, once you've covered certain needs, like I don't have to worry about my house, I don't have to worry about my kid's school. I don't have to worry about like my ability to travel. It's diminishing returns really quickly.

• 26:23Harry Stebbings?

  How did having children change how you think about operating? It's such a big life change.

• 26:28Speaker 02

  I don't have kids. What's changed probably the most is that I went from having very few people I worked with that had kids to a lot of people that had kids. And the one thing I've learned is don't screw with people's kids. Like, don't ever push somebody to prioritize work above their family. I think family should always come first. And if someone's got a kid's soccer game or they need to do some school thing, like do not create pressure in making them feel guilty by not going to do it. I've been burned a few times and learned that never ends well.

• 26:55Harry Stebbings?

  You have a lot of lessons and when I listen to your very calm and composed as a leader today, where do you think you still suck as a leader? And what are you doing to work on it?

• 27:04Speaker 02

  I suck in more places than I'm good at, but what I'm very good at is surrounding myself with a team that covers my weaknesses. And I think that's really important. I think it's very, very, very hard to be such a well-rounded leader that you're just great at everything.

• 27:16Harry Stebbings?

  What are your weaknesses?

• 27:17Speaker 02

  How much time do you have? Probably the thing that I would say I suck at the most is I'm very disorganized. I need to surround myself with people who can take my unstructured thoughts and understand when is there something good here versus it's just an unstructured thought. One of my leadership skills that I've built over time is building a team that feels very comfortable pushing back on me. Like just because I give them an idea doesn't mean that they're expected to go do it unless I tell them, hey, like I'm making an executive decision here. And that's really important for somebody like me. And I think a lot of product-minded, creative entrepreneurs can be. The type that they've always got a lot of ideas like we could do this and we could do that and that only works successfully if you surround yourself with super high quality

• 28:01Speaker 02

  people who understand when there's value there and when there's not and they have to feel confident to be able to push back on you. Our company culture is one where literally it doesn't matter if you're an intern or you're one of my co-founders, you'll push back on me in public. And again, that doesn't mean that like I'm gonna agree with you. I might go and say, that's great, but we have to for X, Y, and Z. We're doing this, we're going down this path. But I think creating a culture where people feel very comfortable pushing back and people feel very comfortable voicing their decision is important.

• 28:24Harry Stebbings?

  What does it take to do that? Is it rewarding them for pushing back? How does one create that as a founder today?

• 28:30Speaker 02

  Well, a couple of things. For starters, one of the things we did was we don't have titles of the company. One thing I observed when I worked at LinkedIn was if a director said something and an associate was in the room, the director was always right, but the associate often was the one who was right, but just because the more senior person was the one who said something. The second thing is, is we interview just very, very aggressively for people who feel comfortable with debate. If you don't feel comfortable in conversations, this is not gonna be a place for you. We rarely leave a meeting, in fact, I can't think of one where people left heated, but we debate things like all hell.

• 29:00Harry Stebbings?

  Do you document the meetings as well?

• 29:02Speaker 02

  We do, especially our key meetings are all very documented and we're very analytical as a company. Whenever possible, people are very cautious about making broad statements without being able to back them up. If you better know your answer, if you just, you know, if you say 50% of users are doing something and it's not actually 50% of users as an example, because you're using some like you're overestimating something, people will call you out very quickly because we're all very deep in the data.

• 29:24Harry Stebbings?

  Do you want people to, because I think one thing that I I struggle with now is like sometimes it's like, hey, only come and be forward with your ideas when they're fully formed ideas and you have data to back it up and support it. And then part of me is like, no, I want people to ideate and be like, hey, what about this? And they may not have thought about it that much and they may not have data, but it might be great, actually. Do you want people to come with fully formed ideas, structured, data oriented? Or do you mind much more natural and organic, hey, what about this? We could do this.

• 29:51Speaker 02

  There's a time and place for both. The worst thing that you can do, in my opinion, is take somebody who comes in and they're super excited when they join a company, they have all these big ideas and they get shut down and they're like, you know, you ask them 18 questions. Basically just shut it down and you make the path towards getting whatever they're thinking about to turn it into reality, made it very long. On the flip side, an idea, an hour, people are just constantly meeting about ideas but not actually executing on them is not good. And so I think that a way of solving is what we do is we have operating priorities as a business. We say these are the most important things for the company to solve. Here are the metrics that we're trying to move. Here's what we're trying to accomplish. When those ideas map to those initiatives, it makes it a much easier conversation because typically you could have a measurement of like, how much is this stuff going to actually move the needle?

• 30:33Speaker 02

  Like, does this actually matter? And then those ideas truly get ideated on. Either extreme is bad at everybody, but people have been in companies where it's impossible to get anything through and that sucks. And then they've also been on the flip side of companies where people are always thinking about something and never actually executing on it.

• 30:48Harry Stebbings?

  You know, when we think about the people we mentioned before, which is Leila and John on some of the cap table, I do just want to ask, you know, you've got this incredible perspective with the prior companies, with curated, with angel investing. What are the core ways that you see founders fuck up fundraising today? And are there commonalities in how you most often advise your angel investments around fundraising?

• 31:08Speaker 02

  Yeah, I think that people over-index on valuations and not on finding the right partner. And I try to find the right balance of what's fair for my team and what's fair for the investors. I'm not a really big believer in running an auction process, right? And going and bidding everybody against each other. Historically, we've said like, here's the price that we believe is fair and that's just what we've gone with. I think where entrepreneurs get it wrong is they're very focused on who's going to pay them slightly more, but you're stuck with this person for the next five to seven years. And does that half a point or point of dilution justify not working with somebody you love? Because if they're actually a good investor, they should add substantially more value than that. Otherwise, it's just dumb money. And I think especially in the early stages of a business,

• 31:49Speaker 02

  dumb money is just giving you a longer rope to hang yourself with versus smart money and really strong investors will really call you out on your bullshit, push you on, do you have a good business here and guide you in the right direction? And they're very, it can be hands-on in a good way. I call my investors very often. It's not that they're reaching out to me and they want weekly check-ins and things like that. I'm constantly going to them. I'm seeing this problem. How have you seen this solved before? Can you introduce me to this person? Surrounding yourself with the right people, both your own team and your investors is really important.

• 32:18Harry Stebbings?

  But I do want to move into my favourite, Eddie, which is a quick fire answer. I say a short statement, you give me your immediate thoughts. Does that sound okay?

• 32:24Speaker 02

  Absolutely.

• 32:25Harry Stebbings?

  So what's the favourite book and why?

• 32:27Speaker 02

  Predictably Irrational by Dan Ariely, and it's just about why we're all irrational in a very predictable way.

• 32:32Harry Stebbings?

  One of my favourites, I love Dan Ariely. Tell me, what's the hardest element of your role with Curated today?

• 32:37Speaker 02

  Saying no.

• 32:38Harry Stebbings?

  What's been the hardest thing to say no to recently?

• 32:40Speaker 02

  Headcount hiring.

• 32:42Harry Stebbings?

  Tell me, what's the hardest role to hire for today and why?

• 32:44Speaker 02

  Our head of brand. It's just because it's such an important role and you can't afford to get it wrong.

• 32:48Harry Stebbings?

  There's also very few good ones and also the majority are pretty good at selling.

• 32:52Speaker 02

  That's very true. That's a challenge in hiring for that role is everyone is an incredible salesperson.

• 32:56Harry Stebbings?

  Totally with you on that. And honestly, a brand and obviously it's what I do, that's just shit, most of them. Sorry, we can take out most things. Tell me, what would you most like to change about the world of startups, Eddie?

• 33:06Speaker 02

  Less smoke and mirrors. I think most people paint this picture that it's perfect and we're all crushing it. And the reality is, is it's an awesome journey, but it is hard as hell.

• 33:14Harry Stebbings?

  In thirty years' time, wherever Curated is then, how would you most like to be described by your team in a couple of words?

• 33:21Speaker 02

  Fair, caring and hardworking.

• 33:23Harry Stebbings?

  You can have a billboard anywhere in the world. Where is it and what does it say on it?

• 33:27Speaker 02

  No mercy, and it's in front of our competitors' buildings.

• 33:29Harry Stebbings?

  What's the biggest weakness for you and what are you doing to change it?

• 33:32Speaker 02

  I've got a lot of weaknesses. Instead of trying to change it, I just surround myself with people who can cover my weaknesses.

• 33:38Harry Stebbings?

  How do you decompress, Eddie? You seem to be pretty on all the time. We chatted about Adam before. How do you decompress?

• 33:44Speaker 02

  I can give you the real answer or the fake answer?

• 33:46Harry Stebbings?

  Give me the real answer. I sit down with a bottle of wine and call my mates in the US.

• 33:50Speaker 02

  Yeah, exactly. I think the real answer for decompressing is three things maybe really decompress me. One is just spending time with any kind of physical activity. That has been a really key part of my regiment. The second is extended periods of time off, like a weekend doesn't do it for me. Like, I need at least a week for me to actually start to like slow down and chill out. And the third thing is spending time with people who like truly get me and can help me think through problems. When I leave a weekend or some period of time where like I've talked through my problems with people and we've made progress, that goes a long way.

• 34:22Harry Stebbings?

  Tell me, final one. What do the next ten years hold for you and for Curated? If we do this again in 2032? Where will we be?

• 34:28Speaker 02

  We want to be the place you go to for all expert advice, able to help as many experts as possible monetize their passions. And hopefully it's not just helping you buy things, right? So we sold you a set of skis and hopefully we're helping you plan your ski trip. We sold you baby stroller, baby crib, and we're helping you with sleep training for your, for your kid. We sold you a coffee maker and we're teaching you how to make your first cup of coffee. The fact that we have a live human in the loop means that you can do so many things that haven't been done in the past. And we're always thinking about ways we're going to unlock that.

• 34:57Harry Stebbings?

  Eddie, thank you so much. As I said, John said so many great things and I'm just thrilled that we got to do it.

• 35:02Speaker 02

  Absolutely. I really appreciate it here. It's great. Thank you.

• 35:06Harry Stebbings?

  My word, that was such a fun episode for me, Stu. Poor Eddie had no idea of what the questions were coming there. It was completely different to the schedule, but he was incredibly accommodating and putting up with me. If you'd like to see more from us behind the scenes, of course you can on twenty vc dot com. But before we leave you today. From websites and online stores to marketing tools and analytics, Squarespace is the all in one platform to build a beautiful online presence and run your business. Now, there are three things for me that really stood out about why I love Squarespace. First, mobile optimized websites. All websites are optimized for mobile with Squarespace. So content automatically adjusts so your site looks great no matter what device it's on. Pretty awesome. Second, email campaigns. Squarespace makes it super easy to grow and engage your audience with Squarespace email campaigns.

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• 37:13Harry Stebbings?

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