EP 83: Silicon Valley Legend Claire Hughes Johnson (Advisor, Stripe) Unveils Her Best Operating Advice

Claire Hughes Johnson is known as one of the top operators in Silicon Valley. Claire shares the most interesting lessons and stories from her time as COO of Stripe and as an early senior executive at Google. We discuss leadership versus management, how to have difficult conversations with members of your team, lessons she's learned from hiring thousands of people over the years, and much more. Show notes: Claire’s Book, Scaling People: https://press.stripe.com/scaling-people Running an Effective Staff Meeting: https://www.youtube.com/watch?v=GIiaFW874q8 (0:00) Intro (0:42) Joining Google vs Stripe (14:17) Holding yourself to a high standard (21:03) Making the hire (24:32) Player vs Victim (28:52) Balance of discussing accomplishments (30:51) Org structure in job interviews (34:07) The most successful hires drove me crazy (37:12) Running a team with inclusivity (41:01) Operating principles (48:06) Say the thing you think you cannot say (53:31) Distinguish between management and leadership (58:32) The golden rule is not a great tactic for a leader or manager (1:03:01) Job titles are cheap (1:11:36) Too many companies make their principles so idealistic that they don't resonate with employees (1:18:57) Don't let perfect be the enemy of good (1:23:38) Disappointing people at the rate they can absorb (1:30:07) Manage people out of seats earlier (1:37:03) Being on the board of a company built to last (1:42:38) What makes the Collison's so special? (1:45:08) You pack it, you carry it Mixed and edited: Justin Hrabovsky Produced: Rashad Assir Executive Producer: Josh Machiz Music: Griff Lawson 🎙 Listen to the show Apple Podcasts: https://podcasts.apple.com/us/podcast/the-logan-bartlett-show/id1606770839 Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1 Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow 🐦 Twitter - 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, Logan goes behind the scenes with world-class entrepreneurs and investors. If you're interested in the real inside baseball of tech, entrepreneurship, and start-up investing, tune in every Friday for new episodes. 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.

• 0:05Logan Bartlett?

  Welcome to Logan Bartlett Show. On this episode, what you're going to hear is a conversation I had with Claire Hughes Johnson. Claire was a longtime COO of Stripe and before that, a senior executive at Google. Claire and I have a conversation that goes in a bunch of different directions, including the distinction between leadership and management, how important self-awareness is as a leader, how to have difficult conversations with members of your team, lessons she's learned from hiring thousands of people over the years, and what makes the Collison Brothers so special. Claire recently wrote a book on operating and is known as one of the top operators in all of Silicon Valley, which you'll hear in this discussion now. Claire, thanks for doing this.

• 0:43Speaker 01

  Thank you for having me, Logan.

• 0:44Logan Bartlett?

  So you joined Google in what year?

• 0:47Speaker 01

  2004.

• 0:48Logan Bartlett?

  And how many people was that?

• 0:50Speaker 01

  Google was like five or six months from the IPO and about 1,800 people.

• 0:56Logan Bartlett?

  Being pre-IPO, you get so much credit.

• 0:58Speaker 01

  I had nothing to do with any of that. Yeah, absolutely.

• 1:01Logan Bartlett?

  I mean, there was so much value created after the IPO for Google that not having any.

• 1:04Speaker 01

  It was. In retrospect, it was really early.

• 1:06Logan Bartlett?

  But being able to say pre-IPO is just like such a point of validation. It was like, yeah, I was there pre-IPO.

• 1:11Speaker 01

  Yeah, it was funny though, because I mean, I think rightly so, Google was super suspicious of hiring in that final sort of six months right before, because you know, there was some probably mercenary behavior going on with candidates. So I felt kind of like a miracle to get hired, but I was so naive. I had no idea what I was walking into.

• 1:29Logan Bartlett?

  And your hire at that point was, your background prior to that was very unusual?

• 1:34Speaker 01

  Yeah.

• 1:35Logan Bartlett?

  Maybe not unusual to go to Google.

• 1:37Speaker 01

  I think, yes, I think eclectic. I mean, I worked in politics and government. I ended up going to business school instead of law school, ended up working in like a sort of a startup consulting firm that was actually sort of one of those tech strategy mashups that happened in the pre-bust, early 2000s, end of the 90s. And so in fact, my work. With some consulting engagements that were really about like CRM and doing data work. And back in the days of data marts and data warehouses and how do you get insights on your customer base? Anyway, so that was sort of relevant in that I was used to working with some, I think, calling them engineers or developers would have been advanced then.

• 2:19Logan Bartlett?

  Yeah.

• 2:19Speaker 01

  But some folks, it was more integration. It was a lot of ETL stuff. But point is, I worked at this consulting firm that had some technical aspects to our work, though I was on the strategy side, obviously. But in the end, I was running engagements that was a mix of technical people and strategy people.

• 2:35Logan Bartlett?

  So more relevant.

• 2:36Speaker 01

  So it was a little more relevant, but yeah, I get to the West Coast and.

• 2:40Logan Bartlett?

  And Sheryl Sandberg hired you.

• 2:41Speaker 01

  Sheryl hired me and I knew some people who, I mean, you know, this is how the world works. I went to business school with some folks who were friends of hers or friends of friends of hers from Harvard. She hired some folks from that time in her life as early operations managers, essentially in her online sales and operations group. And I thought I was doing a friendly call with one of them who was a friend of a friend. And she grilled me for like 45 minutes. And I said, I was like, Laura, is this an interview? I mean, I, I'm like driving in California with my husband going away for the weekend. He was then not my husband, but, and she grilled me and she's like, well, if I'm going to refer you, I have to believe you're going to be good. And I, because Google, like, it was very serious in a good way.

• 3:26Speaker 01

  Now, you know, now I wrote about it in my book. I'm like, you got to take your hiring very seriously.

• 3:30Logan Bartlett?

  Totally.

• 3:30Speaker 01

  So she didn't want to refer me if she didn't think I was good.

• 3:32Logan Bartlett?

  It's an interesting lesson that like, you're kind of always being interviewed in some way.

• 3:36Speaker 01

  That's right. Oh, yeah.

• 3:37Logan Bartlett?

  Just because there's a microphone here. Yeah, yeah. It's just like you're talking to your friend. That's what I tell founders as well is like, if you're talking to an investor, you're fundraising.

• 3:45Speaker 01

  You're getting assessed.

• 3:47Logan Bartlett?

  It might not be a process of you fundraising in some way, but they are definitely putting inputs into how you assess things.

• 3:53Speaker 01

  Oh, for sure.

• 3:54Logan Bartlett?

  And it's just general. So then you were, you were at Google for how long?

• 3:57Speaker 01

  Almost 11 years.

• 3:59Logan Bartlett?

  Wow.

• 3:59Speaker 01

  So I left in 2014.

• 4:01Logan Bartlett?

  And then joined Stripe in 2014.

• 4:04Speaker 01

  I did.

• 4:04Logan Bartlett?

  And you did full time at Stripe for, is that right? One week later. And you were there for six and a half years full time?

• 4:11Speaker 01

  I was, yeah, six and a half years full time as COO. And then now part time for the last few years.

• 4:16Logan Bartlett?

  And Stripe was 162 people.

• 4:18Speaker 01

  It's about 160, yes.

• 4:20Logan Bartlett?

  About?

• 4:20Speaker 01

  Precisely.

• 4:21Logan Bartlett?

  No, no, no, yeah.

• 4:21Speaker 01

  I was gonna say about 160, it was 162.

• 4:25Logan Bartlett?

  When you, uh, when you look back on both Stripe and Google, like, what are one or two takeaways from the cultures themselves, very distinct cultures, but, uh, and I'm sure they involved, but from the times that you were there?

• 4:36Speaker 01

  Yeah.

• 4:37Logan Bartlett?

  Is there a thing or two that really stands out, uh, about the cultures that you think all companies should internalize?

• 4:42Speaker 01

  I think all companies should internalize that there is a culture and to try to understand it. And some of it is intentional and some of it's not, right? I mean, young companies are mirrors of their founders. And so a lot of the culture that you is maybe less conscious is often that mirror of the founder and their behaviors, more their behaviors, right? It's your actions and less your words. You can be aspirational with your words, but it's what do you spend your time on? What do you value? Um, you know, what draws your attention, uh, in terms of decisions you're making? But Google and Stripe have had some things in common that resonated for me and had some things that were quite different, actually.

• 5:24Speaker 01

  I would say in common, uh, both sets of founders had very big ambitions, but, but not completely pie in the sky. Like ambitious, but realistic to a point. But, you know, this, I mean, the thing that's amazing about both those companies is on the B to B side of the businesses, obviously Stripe is all pretty much B to B and Google, everyone thinks it's a B to C because of the search, right? But it's AdWords that it was the revenue business. Uh, and now, you know, Google Cloud and all of that. But, um, to have millions of B to B customers, right? Multi-segment, uh, from pretty early on is pretty astonishing.

• 6:06Speaker 01

  Like you have to have a very big ambition, a global ambition, one where you believe you're building a product that appeals to millions of other businesses. And that was in common and it was not just this is the starting place and we're just going to figure it out. It was like, no, you know, this is commerce infrastructure in the case of Stripe. This is not just payment processing. And there were credible details behind that on plans that the company had and things that Patrick and John saw that needed to be addressed.

• 6:35Speaker 01

  Really to like bring technology to the financial services world, which has is a challenge because it's really pretty entrenched, not in every country, but in a lot of countries around the world. And Google similarly clear missions for both of them, high, high value on individual talent, like, but very different. Google was using a lot, as you probably remember, pedigree to filter out. So what school did you go to? I mean, I had to share my college transcript. Wow. When I was in that process for Google and I was Is that even allowed now? 10 years out of college, right? Like that, to me, it was like, well, haven't I done some

• 7:16Speaker 01

  things since then? But they were really, I was writing essays, but so not only was it where, where did I go to school and where did I go to business school? And, you know, actually, business school was a knock on me at Google. But Stripe much more open to really very different sources of talent. And I think Patrick and John themselves were such active, are such active participants in so many internet communities, which in Google's defense, were not as active Sure. in the late 90s, right? When they started, but whether that's IRC or Hacker News or Twitter, in the more of the heyday of Twitter. But Patrick especially would see someone who had interesting ideas or who seemed talented, maybe that's a designer, maybe it's an engineer

• 8:00Speaker 01

  who's like shouting some stuff out into the Twitter sphere and contact them and be like, hey, let's meet.

• 8:05Logan Bartlett?

  It's an interesting lesson for startups.

• 8:07Speaker 01

  And then we would hire them.

• 8:08Logan Bartlett?

  Well, so that's the thing. If Stripe did it, you sort of need to take chances on the why this person would join your company. Because Google maybe is on a short list of best businesses of all time, at least in terms of Google search and the product market fit around that. And Stripe's on a very short list of like best product market fit of all time as well. And if they're going to join your startup as a Mr. or Mrs. Startup Company CEO, you probably need to evaluate like, what's the reason for them picking you? Are you taking a chance on them in some way? Like, it's not just going to be the pedigreed person with the background that you're seeking out.

• 8:48Speaker 01

  Well, yeah, I mean, I would say early, early Google, it was like, let's find some smart people from Stanford, essentially, because Larry and Sergey had dropped out of there and that was their network. And then fairly quickly, you're right, I think the product market fit for the search side of the business. And then AdWords got built, you know, not immediately, but soon enough that they did have their pick. They also were in a, I mean, again, we just talked about this, the economy wasn't in great shape. I mean, Google was founded at a time where there wasn't so much traffic in San Francisco, as people pointed out to me when I moved there.

• 9:26Speaker 01

  Because there were a lot of businesses that were suffering in that sort of turn of the 2000, 2001, 2002. And I joined Google in early '04, right? So coming out of that, but Google was definitely the shining star in that moment. So they had their pick. I would argue that Stripe, less so. When I joined Stripe, so I feel like I look back now, I'm like, gosh, I felt like every Friday, if not multiple days of the week, I was taking lifts or Ubers either down back into the South Bay or around San Francisco, having coffee with everyone I could meet and selling them and convincing them.

• 10:02Logan Bartlett?

  To join the company.

• 10:02Speaker 01

  Yeah, because. Yes, we were, we had really nice growth rates. I mean, it was an API through which you could wire up your payment acceptance and a little bit of paying out. But at that time, that was very compelling to developers. But it wasn't understood by a broader set of potential candidates you'd hire necessarily. And even engineers beyond people who were having to wire up payments for a startup. And so it was a lot of education. It was more, I mean, Patrick, when he reached out to people, I think them taking the time to meet him was about him more than Stripe, at least in those first years. And then Stripe started to get more of a reputation.

• 10:47Speaker 01

  But for having, yeah, strong product market fit, strong trajectory. But it was like a while.

• 10:54Logan Bartlett?

  Is there anything about like doing things that don't scale on the candidate side? You remember from the Stripe days of like, hey, here's a candidate and here's what we did that went above and beyond to convince them to join?

• 11:06Speaker 01

  Oh, yes. I mean, I think so many things come into my mind. I think it was really that bespoke outreach and personally from executives or from the founders was the number one thing, but being willing to travel and even meet people. Or we had some really active early users, some of those developers who were integrating Stripe, who were giving a lot of good feedback. And Patrick and John just turned around and were like, why don't you come in the office? And like, sit with us and maybe work with us. And then they hired a few of those people. We had this role called support engineer early on. And a bunch of those folks were just early users who were just really smart about here's the bugs, here's the things we need to change. And they came in and started changing it from the inside.

• 11:46Speaker 01

  Stripe also ran this capture the flag contest that some early engineers built. They did it twice, but it was basically this sort of buzzy set of problems to solve. One was very security oriented. And yeah, we happened to need some security engineers. And, but it was hard and it, and it like took a lot of work to build. But it also said a lot about the kind of company it was, which is true. Like incredibly smart people. Willing to use their technical prowess to sort of have fun, but solve hard problems. So capture the flag was very big. Some of the comments that you would find from Stripe founders and Quora, again, and Hacker News,

• 12:27Speaker 01

  like their amount of activity communicating themselves directly in different channels was really high. And I think, and including directly to candidates. So that was the main thing was that bespoke. There were also some instances of, you know, aqua hires that were really, again, targeted, like a really talented young designer, so young that, how did we hire him? I wonder, and relocate him from his Scandinavian home.

• 12:58Logan Bartlett?

  From his parents.

• 12:58Speaker 01

  As an example, yeah, just Logan, that like, like that kind of a situation. Uh, where we're like, oh, we acquired a company that is really a kid who was amazing. I mean, you have to take some, that's a risk.

• 13:10Logan Bartlett?

  Totally. It's an interesting lesson of like, when you're competing against today, if you're a startup with 20 people, 25 people, and you're competing against Stripe or Google or whoever it is, like X company that has hundreds of, or thousands of people and, and everyone's parents and their friends and their family will pat you on the back for joining that company. You have to use what you have to your advantage. And CEO outreach can be one of those things, right? Like what can?

• 13:36Speaker 01

  Same with early sales.

• 13:37Logan Bartlett?

  Same with early sales. What can you do to, to beat Stripe in a sales cycle? Well, you can reach out to that person individually and Patrick and John, I mean, they're doing a bunch of other things and they probably can't spend all the time they did in the early days of reaching out first cold calls to individuals, right? And so using those things, if Stripe had to do it, I guarantee you should probably be doing it as an early stage founder.

• 14:02Speaker 01

  You would still find it Stripe, senior members of the executive team and the founders helping to close candidates.

• 14:06Logan Bartlett?

  Totally.

• 14:07Speaker 01

  But you're right, not anymore. Like they're not doing the cold, they're not doing a lot of cold DMs on.

• 14:13Logan Bartlett?

  Yeah, it works.

• 14:14Speaker 01

  Now I guess you have to pay for it anyway.

• 14:15Logan Bartlett?

  Yeah, exactly. Who knows? The old Twitter. One of the things you said was that you were rated at different times at Google of holding people to a high standard, that your rating like would be variable sometimes.

• 14:27Speaker 01

  Me individually.

• 14:28Logan Bartlett?

  You personally. Sometimes you get good ratings and sometimes you get bad.

• 14:31Speaker 01

  At Stripe. No, generally not that good.

• 14:33Logan Bartlett?

  Okay, well.

• 14:34Speaker 01

  I had very positive manager feedback for every Google Geist, which is our sort of survey, engagement survey, but also had a manager 360 component.

• 14:42Logan Bartlett?

  So you as a manager.

• 14:43Speaker 01

  However, me as a manager. However, there was one question was about consistently holds my work to a high standard, where that was not my highest scoring.

• 14:51Logan Bartlett?

  But at Stripe, you were scored well on it.

• 14:53Speaker 01

  Highly, yes.

• 14:54Logan Bartlett?

  And what do you think you changed in between the two?

• 14:56Speaker 01

  Yeah, I really, I mean, I think part of it was having the revelation and the maturity, the process of maturation at Google, where I went from being, you know, and this happens to a lot of folks in high-growth companies, which is elevated from, I mean, I started as a manager, not as an IC, but I was like a entry-level manager. I got pretty quickly moved into like more of a senior-level manager, which actually I did have some management experience, which was unusual at the time for people. And then was made a few times in my career at Google, the manager of my peers. And that's a hard thing to navigate. And the first thing you think was, well, I don't want to change a lot here. I, they're my peers. Like, we're going to collaborate. I'm going to be their partner.

• 15:38Speaker 01

  I'm not going to, not going to, you sort of, unfortunately, you don't consciously say, I'm not going to hold a high bar, but you do consciously say, I want to be friends. Unfortunately, I don't think managers are friends with their team. Not in the way that I think I was picturing, like, nothing's going to change. It's all going to be fine. And also, you just don't want people to be turned off by your behavior when you all suddenly become their boss. And then I sort of had that happen a few times, and I don't think I learned the lesson quickly enough, which is actually now I am the one responsible for holding the bar, driving the work product. And, and then the other, and there were some instances where I started to see that my team wasn't stepping up.

• 16:18Speaker 01

  And it was a wake up call for me, not just in the feedback I was getting, but in our performance, or in I would see my team with another executive, kind of bringing their A game and with me, sort of taking it easy and having a laugh. And yeah, I was well liked, but guess what? It's not a popularity contest. So it took me some time to just get out of that mode. And also, people like to be challenged. People want to be on winning teams. By the way, our teams did fine, but like, was I driving results at the right level? I think I was driving more the process. And I think the thing that clicked as I went to Stripe. So one, I matured out of that and I started to drive more. At the end of my career at Google, I would say I was

• 16:59Speaker 01

  more comfortable being that leader and setting the bar and focusing on results. But at Stripe, I stepped into a culture that was also more dialed into that. John and Patrick are very clear about that being critical for any manager and leader. With a caveat, when I first joined the company, management was a fairly new concept. And there were a couple of people who'd been hired, one in a sort of engineering leadership role, who seemed to have this construct in his mind, that there was like, almost like the tech lead, and that you see this at some companies, the tech lead, he was driving the work product and work plan and work results. And then the

• 17:42Speaker 01

  manager was more of this one on one coach buddy. And I took him aside and I was like, I just want you to know, we disagree on this. Like, it took me a moment to, first of all, unravel what I think, I was like, what is culturally going on here where the managers seem like a side job? And also more of a coach not holding the bar. And I, of course, had just gone through my own learning process where I was like, this is what leadership and management is. And, and I would say Patrick and John certainly had the leader element of holding the bar. They hadn't thought as much about what, who they were as managers, right? Which makes sense. They'd barely been managing people that long. But anyway, I took this guy aside and I said, I think I've diagnosed what's going on here. And I want to just voice to you that I think it's gonna have to change.

• 18:26Speaker 01

  And I also talked to the founders about it. And they were totally on board. I mean, Patrick, being Patrick, was like, you know, started to read up and look at some research studies. He's like, turns out management matters. Like this is actually one of the things the United States on like economic indicators. We outperform other countries because we have, we value management and, and have management structures that we use and have so for, for, you know, hundreds of years. And it does create some output advantage, again, if done well, ideally.

• 18:58Logan Bartlett?

  Totally.

• 18:59Speaker 01

  But.

• 18:59Logan Bartlett?

  That's funny. Now, talk to me a little bit about hiring. I've heard you be fairly self-critical about your executive hiring versus your, your team member hiring. I guess, can you, can you, I guess, articulate that? And then also, what do you think that is exactly?

• 19:15Speaker 01

  That's a great segue because it's the same problem.

• 19:19Logan Bartlett?

  It sounds like.

• 19:20Speaker 01

  It's the same problem.

• 19:20Logan Bartlett?

  The likability thing.

• 19:22Speaker 01

  So the, yeah, the likability slash, like if anyone, if you asked anyone on any team, either a team of colleagues or a team under me, they would call me, I think, a very collaborative leader. Like I am not out front. I will set the pace in some of my behaviors, but I am all about the sum of the parts. I'm like, give me your ideas, give me your idea. Like, I don't think, I mean, part of the value of, look, I've worked with some really, really smart people, Logan. I'm like, am I the smartest person in the room? No. Am I good at some things? Yeah. But like, I need all of you. And so I think part of it is the likability, though I think I've gotten over more of that. But there's a big part of it, which is, I want to collaborate with someone. I want their ideas. And I'm an optimist.

• 20:06Speaker 01

  I want to, like, if I like, I want to like them, right? I want to be like, let's, you, let's give each other energy and we're going to be better. And so I think my optimism, combined with the collaborative instinct and default, um, yeah, leads me to, has led me to some, it's, it's, I mean, I think I just have better ma, pattern match on hiring teammates and, uh, hiring executives is hard because.

• 20:31Speaker 01

  There's also how they show up with you versus how do they show up with, you know, whether they're, if they're a sales leader with prospects, how they show up with their team. Like, how do you get at them inspiring followership? And I think I hadn't got my tools built well enough on some of the hires I made, where in fact, they were actually decent colleagues, like great to, great to have a one on one with, but were falling down on some of their own leadership stuff for the people below them. Right? Which I wasn't assessing very well.

• 21:03Logan Bartlett?

  Do you think you, you determined at some point too early in the process to make the hire? And that you liked the person and you moved into selling mode?

• 21:12Speaker 01

  I think that's also, I, I think that's, it's always a tricky balance. You know this because you're selling them to get them into the process.

• 21:18Logan Bartlett?

  That's the hardest part of venture is like, it's this buying and selling.

• 21:21Speaker 01

  Yeah, you're selling to get them in because again, at the point that Stripe was, we were looking around the corner and saying, we need some really experienced leaders. So I'm trying to pull people who've got pretty nice jobs at pretty great companies. And so you're selling and then you try to flip into assessing and being discerning, which is a hard flip after you've been selling. And then at the end of the process, you're selling again and you're a hundred percent right. If you aren't really intentional about, wait a minute, wait a minute. I am going to really assess. Now, I would say, yes, that was part of my mistakes. But actually Stripe, we are, if anything, a little over rigorous on hiring and process. Like I wasn't hiring alone. Patrick and John are meeting these candidates. Multiple people are meeting them. We do do reference calls.

• 22:06Speaker 01

  So I didn't feel like I didn't have some of the mitigate, risk mitigators in place. I think I did, but this does come down to me. Like ultimately, I think my opinion became too favorable too quickly, to your point. I didn't rush to hire them too quickly, but my opinion became favorable too quickly. And it was often based on, again, a, a good chemistry, one to one, but also, you know, these folks had track records and I'm looking at the track record. I'm thinking, I'm believing it, right?

• 22:37Logan Bartlett?

  Yeah.

• 22:37Speaker 01

  Which sometimes, sometimes people fail up.

• 22:40Logan Bartlett?

  Totally.

• 22:40Speaker 01

  Sometimes also, you know, people get lucky, they're in the right place at the right time.

• 22:45Logan Bartlett?

  If you're looking back on all the lessons you've learned, is there, is there a point to take away from all of that? Like if, if, if someone were to hear that and say, maybe I, they have a bias to all the things you just said, is there anything you would encourage them to think about?

• 23:01Speaker 01

  Yeah, I, I think one is, I mean, Cheryl did this well. She had someone who was really opposite to her, who she had on basically every hiring committee with her, uh, who I, by the way, was my scariest interview for Google. And I was like, geez, this guy is poker face, so like, all in the details, very analytical, high pressure interview. Um, and Cheryl's so charismatic and so, you know, like, let's talk about you, you know? And he was like the opposite. And I think she was smart. She's like, this, this person is going to pull stuff out of the candidates that I'm not. And I need that foil. I mean, my book talks a lot about self-awareness. Like, you gotta know your blind spots. You gotta know what you're not going to do in the interview and what you're not going to get at. And you've

• 23:44Speaker 01

  got to find someone who's going to get at it. And I think that what I did is I maybe over-trusted Stripe, some of my executive colleagues to be that. But if I really thought about it now, I'm like, hmm, there's probably someone I worked with in a different part of the company who could have been my buddy in that way. So that's one tactical thing that I, I probably should have done differently and more consistently, frankly. Um, so that, that's one. I think another was, I did a lot of reference calls. Did I talk to people who'd worked for the person? Not enough. Maybe not at all. I talked to their manager. I talked to former colleagues, but I think, and, and occasionally I would talk to former team members, but you know, pretty selectively, people they provided. I wish I'd gotten more

• 24:29Speaker 01

  of that view of them as leaders. That would be another tactic.

• 24:32Logan Bartlett?

  That's interesting. One of the things I heard you say is that the hardest mindset thing to overcome as an employee or with an employee is if, uh, that they're, they're a player, I think was the term you used, or a victim.

• 24:44Speaker 01

  Yeah.

• 24:44Logan Bartlett?

  Can, can you elaborate on, on what that difference is and how you were maybe able to tease that out in an interview process? Or like, what questions kind of lead to being a player versus a victim?

• 24:56Speaker 01

  Yeah. So credit where credit's due. So Fred Kaufman, um, wrote this book Conscious Business, which is one of the, like, I don't read that many business books, like, all the way through.

• 25:07Logan Bartlett?

  You write, you write business books.

• 25:09Speaker 01

  I now write them, but even my book is written more as a reference manual. I'm like, I don't expect you to read all the way through. Just look in the table of contents. That's why it's so detailed and read what you want to read. But Fred's book is really strong and he has a few frameworks. Fred founded this company, Excellent, that was sort of a consulting, he had been in MIT, been an accountant, then he was an MIT professor. Then he founded this consulting company, working with leaders. And then he ended up as like the in-house leadership coach at LinkedIn. I think he's still there. And Fred had this, a bunch of frameworks. The book has some great frameworks, but one of them is victim-player. And it is, I think, a very common framework you see at all levels, not just executives, anyone in a company, basically any of your friends, too. Like, we have, I have friends who are

• 25:52Speaker 01

  victims and who are players. I tend to like the players better, but, and the victim is either the, the example Fred would give is when your kid, you know, comes home from school with some, you know, they lost something, you know, they left their sweater at school, or they had a toy they brought to school for show and tell and it's broken. And they don't say, they don't take responsibility. They don't say, I left my jacket at school. They say, the jacket is at school. Or they say, well, the toy is broken. Or the, they kind of imply it broke itself. And it's, and it does happen early in your life where you, you kind of don't, it's embarrassing to fail. It's hard to make a mistake. And pretty early on, kids and adults, like the adults we become are programmed to sort of

• 26:35Speaker 01

  not want to say, I failed. And the victim part of that framework is people who blame others, or who have trouble taking responsibility or accountability. And the really overt version of it is the, no, no, no, Joe didn't deliver, like, we had a dependency on Joe's team. His team didn't deliver, and that's why we missed the goal. And you kind of say to the person, wow, and was there nothing you could have done differently? Oh, no. Joe's total failure by Joe. You know, you're like, what?

• 27:06Logan Bartlett?

  And you could actually-

• 27:07Speaker 01

  How, how are you even-

• 27:08Logan Bartlett?

  If you ask-

• 27:09Speaker 01

  Like, have a straight face?

• 27:10Logan Bartlett?

  It's actually crazy if you ask someone, like, what's a project you failed at in your last job? How quick- They are to shun responsibility because it's an interview setting and you want to put yourself

• 27:19Speaker 01

  Exactly, it's actually.

• 27:21Logan Bartlett?

  But if they don't highlight any self-reflection, like you, you have blame in it.

• 27:25Speaker 01

  No learning. By the way, this is also not a high-learn person. It's like you really learn from mistakes.

• 27:32Speaker 01

  You know, like actually my son came home last night and he's like, we got a pop quiz in science and I got one of the questions, only three questions, I got one wrong. And I said, I tried to like, as a parent, you try, I say, oh, well. And what did that do for you? Like, you know, that's probably why it was a pop quiz. He goes, yeah, now I really know that thing. And I was like, yeah, you do because you screwed up. And I mean, I think the best, the people, and so Logan, to answer your own question you just did, which is in an interview setting, you're saying, tell me about a time you failed. Tell me about one of the biggest lessons you learned. Describe the project. What was your role in it? And the victim people, again, they'll be less overt than, I mean, some of them just blame everyone and vent and you're like, okay, you're, you're just a downer to interview with.

• 28:16Speaker 01

  But they'll be less overt, but it'll be a lot about other people involved. It'll be about constraints. It'll be about dependencies. Of the, you know, the thing I learned is I was spread too thin. I didn't delegate. But, but, but they won't take responsibility. It'll be very hard to get them to say, it was my project and ultimately I, and I was responsible. And yes, I should have delegated better, but that was on me. That's what you're waiting for, someone to say, yeah, I look back. I mean, I could say, I look back and say, well, some of my worst hires were people that I just wanted to like. And I didn't like hold them to a high enough bar in the interview process.

• 28:52Logan Bartlett?

  Do you find the opposite to be a problem if someone tells you accomplishment and there's too much like, well, I did this and I did that.

• 29:00Speaker 01

  Yes, yeah. I, I, I mean, I think there's this balance. This is where having the pattern match of thousands, I think I've done, I have, I've done thousands of interviews. And, and I wish I could totally distill this, but it's about balance. There's a lot of, the best candidate to me, the best interview, there's a lot of we actually. There's a lot of, because that's the thing that the, the player, by the way, construct is not. It's all about me and I take all responsibility and I'm the, the, the star of the show. Cause that's like a narcissist, right? It's someone who is all about understanding their role, understanding what they could have done differently, but also giving credit and collaborating and being like, oh, if I hadn't had this person on my team, I don't know if we would have made it, you know? I love, it's a self-awareness thing.

• 29:42Speaker 01

  It's like, it's going to be the combination of things, but when the chips are down and they did have a role to play, do they own what their role was and what they learned from it? And were they accountable? And you, and you want a little bit of eye. And if they're not, if they're bringing a lot of we, you stop them and you say, I really appreciate actually that you're bringing a lot of the we to this conversation. You're giving examples of your whole team. Tell me what you specifically did. What was your role? And they'll kind of look at you like, yeah, you caught me out. And then they will, if they're good, they'll go there and they'll say, look, I, it was my idea. I did come up with that idea and, you know, but you kind of have to force them into it. Uh, and, and I like that. I like people like that.

• 30:23Speaker 01

  But if they don't go there, that's also a flag.

• 30:28Logan Bartlett?

  Hi, I'm Logan Bartlett, the host of this podcast. This is not an ad, as you may know, we do not advertise or monetize this podcast in any way. I just wanted to take a quick second to tell you that we have a bunch of killer guests coming on over the course of the next few weeks. And so if you're enjoying these conversations behind the scenes with both entrepreneurs and investors, please do subscribe to our channel so you don't miss out. Now back to the episode. One of the things I've heard you also interview or use as an interview tactic is an org structure.

• 30:57Speaker 01

  Yeah.

• 30:57Logan Bartlett?

  And pulling people on their, their org structure, which I thought was so fascinating. Can you talk a little bit about why asking someone about their org structure, how it came to be, how that can be used as an interview tactic?

• 31:10Speaker 01

  On the good parts of my executive hiring, I, I want to say it wasn't all disasters. One of the best questions I, I found I came up with was, this is the days where ideally you're in person with the candidate, but you could do it over Zoom, which is let's get it a whiteboard and just, can you just map out your current team for me? So there's you and then like, tell me the roles. And, you know, you don't have to name all the names, but like, I'd love, you know, Joe, Teresa, you know, Mahak, whatever. Give me the names and then I'd love to walk through a couple of things like, well, one, why this org structure? Because um, one of the traps there is your org structure should really reflect your priorities and your strategy and it should have clean accountability lines. And when you hear an org structure, they're like, wow, this guy was gonna leave.

• 31:56Speaker 01

  So I had to give him like two jobs, basically. You're like, hmm. So you didn't really have the hard conversation with that guy, did you? Or, or there'll be a, well, I inherited that person and I don't love this structure, but I don't want to rock the boat. You know, you're like, hmm. And why not? Like, what, what are you afraid of? Right? So one is why that org structure isn't logical based on what you are, your objectives are and your strategy is within the broader company. The other is tell me about the individuals. And the trap there is people, leaders who come in, and I'll, I'll put it in context. I'll say, well, how long you been in the role? Say they've been in the role three years. It's the same team they got. I, I mean, maybe you, once in a while, you inherit the perfect team.

• 32:39Speaker 01

  But I have never seen that happen, like, perfect, especially if you come in as a leader and reset the strategy. Like, they could be great people, but do you have the right capabilities for that strategy? That's really the perfect team? So big red flag if they've made no changes. Uh, also a red flag if everything is different, like everyone is new. I'm like, did you just churn every single director? Like, did no one want to follow you? This goes back to followership, right? You want this mix. You want thoughtful, you want a story. By the way, my favorite is, well, there was this person in the org I found incredibly talented. You developed them into a role, like you didn't just hire from the outside or you did change the team, but part of the team are people you identified who were talented, who were getting squelched in the org and you wrote, you know, lifted them up.

• 33:23Speaker 01

  And what will happen is also you'll see how the person is, and this is the more nuanced part of this question. Do they get energized talking about the people and their development and their stories? The people under them as leaders? Or are they kind of a little dry about it? They're like, yeah. She's been in, you know, at the company for 10 years. I do wonder if she's gonna leave. But, you know, if she does, she does. Like, right? You're kind of like, well, what have you done about that? So some people are more energized as managers in that moment when they're describing their people and they almost get into it. And some people, you can tell that that's not how they lead. That doesn't mean they're a bad hire, by the way. But they're not leading with the people element of management.

• 34:07Logan Bartlett?

  I, I, I heard you say some of the most successful hires you've made. I think they

• 34:12Speaker 01

  Drove me crazy.

• 34:13Logan Bartlett?

  Yeah, annoyed you. You knew exactly where I was going. Did they drive you crazy in the interview process?

• 34:17Speaker 01

  In the interview.

• 34:18Logan Bartlett?

  Hey, but, but

• 34:19Speaker 01

  And also closing.

• 34:20Logan Bartlett?

  At closing, okay.

• 34:21Speaker 01

  Some of the hardest closes I've ever had. Candidates who were driving me up a wall, questioning every number of the business, the role, the JD. What do I expect? What am I like to work with? Like, you're through the wringer. And you're like, do you even want a new job? Like, what? They were some of the best hires I ever made.

• 34:40Logan Bartlett?

  It is that because

• 34:41Speaker 01

  They were just like hyper analytical, different brain thing. You know, I'm very intuitive.

• 34:47Logan Bartlett?

  Is that because it was at a compliment to you?

• 34:50Speaker 01

  Yes, huge compliment. Yeah. Huge compliment. Brought out some stuff in me that needed to be brought out. It's not like I don't have it, but I don't lead with it. I'm much more intuitive. These are just like hyper data driven people. Some of them are actually a little bit risk averse. Some of the compliments to me, I'm not afraid of change. I'm not afraid to make a decision and, and like drive to action. And some of the compliments to me are people who are like, hey, wait a minute. Do you really have all the data you're gonna want to make that decision? And, and sometimes they're right. Like, I should stop. Like, why? What's the rush? I mean, and, and so, yes, they drove me crazy. They were hard to connect to in the interview.

• 35:29Speaker 01

  And, but they did well on the questions, but I had to sort of, you know, this is where you have to check your biases. I'd be like, wow, this is like sort of annoying, but actually when I read the answer back and I think about my frame, my rubric for what is a good answer, these were great answers. They just didn't deliver them in a connected way to me because they thought about it very differently than I did. And then in the process of answering their questions and closing them as candidates, that they're very different. Yeah, some of my best hires were completely the opposite of me.

• 35:58Logan Bartlett?

  That's a compliment point to like, sometimes you need a hire to augment your own weaknesses. And we'll talk about self-awareness in a second.

• 36:06Speaker 01

  All the time.

• 36:07Logan Bartlett?

  Hiring the exact same profile that you have is going to lead to duplicity.

• 36:11Speaker 01

  Well, it's going to lead to a team with a giant amount of blind spots. I mean, I think diversity gets used as a word meaning certain things, but I actually think fundamentally, a diverse team, meaning in all the ways, whether that's, you know, gender and racial, but I'm talking about, you know, really work styles and preferences and what part of your brain do you lead with or what, or even your socioeconomic background? How hard did you have to work to get to where you are? What's your perspective on our users? Like, what, how have you experienced life? Like, that kind of diversity is how you get a team that's going to outperform other teams. But it's not going to be as comfortable a team for you to hire and lead. And the minute you recognize that, the better.

• 36:57Speaker 01

  Like, it will not be, it's easy to hire a bunch of your friends.

• 37:00Logan Bartlett?

  Totally.

• 37:00Speaker 01

  Right? But you're just not going to be, you're going to be a team that can move pretty comfortably, quickly, within a very narrow band. If you want a team that can outperform, you're going to have to dig.

• 37:10Logan Bartlett?

  And there's empirical evidence, maybe the hospital, the hospital story.

• 37:13Speaker 01

  No, I mean, I think one of the interesting things to look at is if you have inclusive, this is a big if, if you lead a team with inclusive practices, you can get a three to five X return on that team. So they're diverse and there's inclusive practices. If there's not inclusive practices, we can talk about a homogenous team can actually get pretty far, pretty fast, just not outperform. But yeah, I thought Amy Edmondson, who's the psychological safety researcher and writer, which she now wishes she hadn't called it psychological safety because I think it's a term that like, doesn't really mean anything anymore. But Amy Edmondson has been part of some research studies. There's a whole field now that looks at this. And one of them that I thought was fascinating was about ICUs.

• 37:55Speaker 01

  So in intensive care units and hospitals, which are actually all pretty similar. They'll run quite Similarly, an intensive care is essentially the patient is monitored 24 hours a day. And there is a team of care. There is like a nurse, a physician's assistant. There's often the person in charge of anesthesia or drug administration. There's the doctors, multiple doctors. And there's power dynamics in that team. You can all imagine them, like I don't have to describe them, but you know, there are the people who see the patient the most, though, are more the nurses, the medical assistants and less the doctors, right? That's just the way it is. They're sitting in the room practically with these patients. And the ICUs that had high inclusion, there were 18% fewer deaths.

• 38:41Speaker 01

  Like people died when there was a lack, when there was a diverse team and lack of inclusive practices. What was inclusivity in this? So inclusivity in this case is comfortable, like think about this, comfortable speaking up to power, comfortable sharing ideas, like the nurse saying, actually, I don't know if that drug agrees with that patient. Or I saw you come through yesterday and make this observation. What happened? Like this is a team that is putting it on the table to each other and is actually doing it to get the best outcomes as opposed to not rock the boat with egos and power dynamics. And by the way, these are people under a lot of stress and pressure.

• 39:21Speaker 01

  And you know, these doctors are buzzing through and this is a team where you stop and you say, I think I see a problem. I mean, it's like the Japanese pull the combo cord, right? But this is the equivalent in day to day operations around people who are very sick. And I think that, so how do you create that? It's how do you create an environment where people are unafraid, no matter what, where they feel they fall in the status stack to speak up? Ideally, obviously with a great idea or with an observation or a question. And that is a thing that is very important tactically, day to day to do well. And it's hard to do well, but it is about how do I make sure, you know, the right people are in the meeting, that they're all participating?

• 40:04Speaker 01

  You can use check ins and check outs, which I talk about in my book, that if you're the leader, it's probably going to be a killer if you give your opinion first. Like if you lead with, here's what I think we're gonna do. We're gonna launch product X next week. You know, like, are you really? You've got to have a pretty great team environment for someone to say, I don't agree with you, boss. You just started with, you just started with the punchline. Like, you should instead say, we've got this decision in front of us. I want all of your opinions. I want to go around the room and hear them all. Or even better, let's all write them down so we don't group think. Like, everyone write them down on a piece of paper in front of you, or in the doc, or in your own doc, and then let's all at once load them in and see what we think, right? Like, how do you build these ways to prevent human behavior?

• 40:49Speaker 01

  Human behavior is about, you know, we're, we're animals. It's about status. It's about how comfortable we are. It's about group, you know, group think is real. And it has really good reasons behind it, but you've got to prevent it.

• 41:01Logan Bartlett?

  Totally. I want to talk about your operating principles in your, in your book. So number one, build self-awareness to build mutual awareness.

• 41:09Logan Bartlett?

  Can self-awareness be learned?

• 41:11Speaker 01

  Oh, 100%. Yeah. I mean, I think that, um, look, the thing that, so true. I've observed this. First of all, the thing that you, Logan, are probably really the most amazing at as a human. I know for me is like breathing. Like I have no, I, my actual best strength. I had, I had no knowledge of for most of my career. Uh, because I was like, well, doesn't everybody experience things this way? No, not everybody experiences information, data, communication, whatever it is. That way, like, but it's like breathing. So one, don't forget self-awareness is about your strength as much.

• 41:54Speaker 01

  The other is blind spots are blind spots because they're blind. Like you do not know the thing that you don't know. Like, and so that feels easy to say, but hard to admit and actually see because you're blind. So how do you learn it? I mean, there's a ton of different assessment tools. They're not all perfect. And they're not all specifically custom. I know in the world of AI, actually. Maybe we'll have a tool that is much more built and trained on your model. That can reveal these and other models, right? And can reveal, hey, by the way, the other models have this thing that you don't have. But, but let's say these tools. So I'm talking about Myers-Briggs, DISC.

• 42:35Speaker 01

  Uh, there's this insights discovery tool that I really like. Enneagram, some people use in a professional setting. The big five personality test is one that has a more proven track record in research to actually determine some outcomes in terms of you as an individual. I don't really care. I've actually taken Hogan assessment. It's this like really long intensive questionnaire that you can take. I don't really care which one. I've taken them all, I think, pretty much. But every single time I take one, the point of the exercise is to like, one, listen to it. What, and ideally, someone who has some experience with the tool is giving you some readout on your results, but you can also read it yourself. You're listening and self reflecting and you're like, huh, what did

• 43:17Speaker 01

  I learn that I didn't really know about my, it's really about preferences. It's about your defaults. Like, all humans have some default settings. Like, what are my default settings? And if those are my default settings, what are my not default settings? What do I not do naturally? And I think, so yes, you can learn, you can take the tools, you can be better even when it's not fun asking for feedback. And actually, instead of saying, especially if you're the leader, you can't end a meeting or make a decision and be like, hey, what'd you think of that decision? Like, what do you think of me? Like, of course, the people are gonna be like, that was great. That's great. You have to say things like, what could I have done differently to make that thing better? Or what do you wish I'd done? Now that we looked, look back and we made that decision, what do you wish I'd

• 44:00Speaker 01

  done that would have made it better? Right? Like, you have to get pretty specific. But asking for feedback, and then, by the way, listening to it, like, writing it down, self, self-reflection is underrated. Like, why don't people at the end of the week, like, sit down for 15 minutes and just write, what do I think went well this week? What didn't go well? And why? Why do I think those things went well, but or didn't really go well? And if you've done some work on your default settings, I bet you'll find, by the way, most of the time I'll find, I was under stress, and I went to my default settings, and I screwed that thing up. But if you don't sit and think about it for a minute, you're not learning.

• 44:40Logan Bartlett?

  I would encourage people if they want to build self-awareness as well, if you have a podcast, YouTube Commenters will make you very self-aware.

• 44:46Speaker 01

  Oh, they sure will.

• 44:47Logan Bartlett?

  They give you, any insecurities you have, they're very quick to point out.

• 44:51Speaker 01

  Yeah, I don't know.

• 44:51Logan Bartlett?

  Issues, yeah. So that's another way.

• 44:53Speaker 01

  Always dangerous to read.

• 44:54Logan Bartlett?

  Myers-Briggs, Enneagram, YouTube Commenters. You can each find your own. Do you try to hire for self-awareness or do you understand then that you can develop that over time? How much of that do you think you can?

• 45:06Speaker 01

  That's a great, I mean, I think earlier in the career, the less you're going to expect that someone's really developed that. But I do hire for it in that I think people, this goes to kind of core, core instincts, which is I think people who are fundamentally curious and learning oriented, you want to hire. And I mean,

• 45:29Logan Bartlett?

  Can you tease that out? Like, how do you ask that question or get to that?

• 45:32Speaker 01

  Yeah, I think you ask. I mean, I have some sections in the book where I have a bunch of like interview question suggestions, but I think there's one, you know, tell me something that you learned about recently that surprised you or that you're passionate about or, you know, like there are people who just are like, I don't even know what to do with that question. And you're like, hmm, do they not read? Do they not talk to people? Do they not study something new in their, look, we're in tech, I mean, I've worked in tech, like there is something new happening in literally the underpinnings of technology. Like there is a new AI model with significant improvements every like 18 months right now, and it's getting

• 46:13Speaker 01

  faster. Like, if you're not aware, and then if you think about compute power and cost of that, like, if you're not thinking about, like, what are the underpinnings of the capabilities we have to deliver the product? Even if you are a English major who has not ever, like, I've written some HTML, but not a lot of code. I think a lot about the macro environment of the underpinnings of technology and how it's changing and what does that mean? For my company, my product, my team, right? Like, I better be curious. I better be educating myself. And by the way, bonus points if I'm also doing that in something else that's outside of tech that I'm passionate about, you know, maybe it's gardening, maybe it's, you know, Taekwondo. I don't really care, but like, are you curious? Do you care? Are you like a developing human?

• 46:56Speaker 01

  So self-awareness may, I think can be learned, but it's very hard for someone to learn if they're not curious, if they're not a learner. And one of the things in the book that I talk about, I think the hardest employee situation I faced is someone who is a good performer, but could be great, but they have what I call a self-awareness gap, where you're sort of trying to give them feedback and they don't see it. They're like, no, I'm pretty great at that, actually. Yeah, like, I mean, I don't know what you're talking about. Like, what, what? Are we talking about the same thing? And most people I find when you give them the feedback and you have to be direct, are totally with you. They're like, wow, yes. If only I'd communicated more crisply in that moment,

• 47:41Speaker 01

  or if only we'd done the analysis, like, and scoped the problem in the way that made that analysis more helpful. Like, they totally get it. But then there are people who are saying, yeah, no, I feel pretty good. Like, I don't know what you're talking about. It's so hard to close that gap. Like, I, so, so I think to a point, it's learnable if they're curious and they're a learner, but there are some individuals who cannot get at the blind spot.

• 48:05Logan Bartlett?

  Interesting. Operating principle number two, say the thing you cannot, or you think you cannot say.

• 48:11Speaker 01

  Yeah.

• 48:12Logan Bartlett?

  Can you share an example of ways in which you can approach difficult conversations in a slightly more comfortable way? It's human nature to try to be agreeable, I think.

• 48:22Speaker 01

  It is. No, it is. And it's also human nature to not feel confident about an intuition or a hypothesis you have, especially if you're more data-driven, especially if you're, you know, sort of in an engineering or finance mindset. But what, say the thing you think you cannot say is really about is taking some risk. In putting out an observation, idea you have, a question you have. And I think doing so as a manager is part of what I talk about in the book, but I actually, I don't care what your job is. Like, this is how breakthroughs happen for individuals, like whether it's out to dinner with someone or in a meeting or in a project, which is the person who like pokes at, but wait a minute, did we think about this all wrong?

• 49:04Speaker 01

  Or why haven't we thought about X? You know, why are we talking about this when the real problem is that? Right? But if you don't say that, there's no breakthrough. And so as a manager, you get nervous because like, I think I'm issuing some kind of judgment on someone when I say the thing I think I shouldn't say.

• 49:22Speaker 01

  And you have to, I think, step back from that and say, no, what you're doing is sharing a hypothesis you have and asking someone to react to it. And then you can refine the hypothesis. And I think that the safest, to your question, the safest thing to do is just ask a question. Now, maybe that's in a meeting, which is like, maybe in the meeting, it's like, well, why aren't we talking about the fact that we have missed this milestone on our roadmap for three quarters in a row? And everyone's like, awkward. But hey, if I'm, if I'm a good leader in that room, I jump all over that. I'm like, yeah, I should have said that. You know, I'm like, why did we? And then you're having a really rich conversation about a huge blind spot, probably, by the way, that your team has,

• 50:07Speaker 01

  which is we keep saying we're going to prioritize that thing and then we're not. Why are we not? Like, be the person who creates that breakthrough conversation. Or with the individual, by the way, yes, you're taking a risk. It's a one-on-one. You're giving someone feedback. They might get to a breakthrough. They might get defensive and that is okay. They might say, what do you mean you thought I was nervous? You say, I'm sorry, like totally my perception. I just experienced you in that meeting, like not as confidently as I normally see you with that material. And they're saying, well, I don't know, I don't know. You say, great, if that's, you know. Totally could have been just my, again, you're just a mirror holding up to someone. You say that's just could be my perception. But what I do find is people will then think for a minute, they'll sit on it.

• 50:50Speaker 01

  The next day they'll be like, maybe I was nervous. Like, why do you think I was? I'll say, well, why do you think, you know, you'll still, the breakthrough might not happen quickly. Uh, and you can be wrong, like, uh, believe me, I've been in the meeting where I've put a, a, a theory out on what's not being said. And I've gotten looks of horror from people. They're like, oh, and then I'll look around the room. By the way, you gotta read the body language and the faces. This is not usually a verbal exchange when there's look. And I'll say, hey, from the look on all of your faces, it looks like I'm wrong about that theory. And there'll be some nodding and someone though, will then jump in and say, no, no, no. What it is, is this, because so what I've done is I've provoked opinion.

• 51:30Speaker 01

  And ultimately saying the thing you think you cannot say is trying to provoke someone to share an opinion. Uh, or some data that backs up an opinion ideally, uh, that wasn't out on the table.

• 51:41Logan Bartlett?

  Do you find it's easiest to do that in close proximity to when it occurred? Or giving a little bit of time so that there's less defensiveness? Uh, but, but if you give too much time, then it seems like it's more of a affront to them. Uh, like, is it better to do it closer or further away?

• 51:59Speaker 01

  If I had to give one answer, I'd say closer in the same way that like giving feedback to someone, ideally pulling them aside immediately and saying, hey, how did you think that went? Here's some, like ideally closer, but I'll, like one of my, um, one of my strengths that's like breathing is I kind of have like fast processing speed in moments. And I'm like unafraid to go there real time. And that is not the case for a lot of people and that is totally normal. And so I would say you have to read the context, read the individual. Maybe close proximity is the next day. And to your point, sometimes things are heated, right? Sometimes you're in an executive team meeting, maybe you're the founder, they're all disagreeing. Everyone's looking at you, I want a decision right now, right?

• 52:42Speaker 01

  You feel like I've gotta call peace. And, and the best thing you can say, cause you need some space is say, wow, a lot of disagreement. Appreciate all the opinions. It's looking to me like I'm gonna be the one who has to make this decision. And I'm going to take some time and gather my own data and think about it and I will make it by Friday. Now, the danger of doing that, by the way, is everyone starts lobbying you. So, so good if you also lay out a process and you say, if anyone has opinions and you clearly do, please send me an email, you know, or send it to the group by the end of the day. But right, like, but try to, it's totally legitimate to say, you know what, the thing I think I cannot say, I'm not going to say right now, because there's a lot of emotion in the room, but I am going to commit to saying it.

• 53:27Speaker 01

  And, and that, you know, again, is a risk because you might not be ready.

• 53:31Logan Bartlett?

  Operating principle number three, distinguish between management and leadership. Can you expound on that?

• 53:35Speaker 01

  Oh, yeah. So I think there are some schools of thought that man, you can be a great leader and you don't need a lot of management skills. I think Reid Hoffman would cop to believing that and he, I interviewed him for the book and he talks about it. I actually believe you do need both ultimately in your career. Often I think people lead with one or the other. I probably led my career as a great manager and then became a leader and I'd say probably the opposite for some, a lot of founders that I work with. But ultimately, if you're a founder who's the CEO, you're going to have to manage executives and an executive team and that's going to take some skills in that area. Here's the good news, management is really knowable, it's learnable. I mean, a lot of what's in my book is just me sort of saying like, here's some basics,

• 54:20Speaker 01

  here's some checklist, here's some things, like you, they happen behind closed doors, but they're very learnable. You know, management is about like, I, how do I get from point A to point B? Like, look at my talent, make a roadmap, milestones, metrics, like, it's like, very, very doable. I think leadership is actually harder to learn and very different because I think management is a lot about moving people through time and space to accomplishments, whereas leadership is making people pretty uncomfortable. Fundamentally, I think great leadership is setting a vision that doesn't seem possible often, or setting a bar that doesn't seem achievable.

• 55:05Speaker 01

  And, and as we talked about, like, one of my I guess areas for development or blind spots is like, I'm pretty empathetic. I'm pretty collaborative. I look at a group of people and to say to them, and now we are going to do a thing we have never done before without any real knowledge of how we're going to do it. And we're going to do it by December is very uncomfortable for me because I am so empathetic to the people in that room. I'm like, how the hell are we going to figure this out? I remember when I started at Stripe and our support situation was kind of a tire fire for good reasons. We were growing quickly, et cetera, et cetera. The team was small. We didn't have our processes. We didn't have good tooling, all the, all the things. And at some point, but admittedly under pressure from Patrick, the CEO and co-founder of Stripe,

• 55:49Speaker 01

  I ended up having to say to the whole company, this is going to be fixed. We are going to have 24/7 chat, phone and email support in seven languages by the end of next year, you know, whatever. And I'm sitting there going, how the hell are like, you're putting out a vision and you're putting people on the line. You're putting people who report to you on the line and saying, we're going to deliver this thing and you have no idea how it's going. I mean, you have some idea, but it, it seems impossible. Like leadership is uncomfortable and it's also turning up the heat on some people who are often very good. You're like, you know what? That still isn't good enough. Um, so you can learn it, but it's much more psychological. It's much more about, can I feel like, can I do that

• 56:31Speaker 01

  confidently? And, and by the way, when you do and your team, maybe you don't hit like the crazy goal you set for December, but they're going to do better than you expected. And that's when you start to get this virtuous cycle of wow, leadership actually works. Like I articulated a vision and people colored in the lines. People figured out how to get there. I didn't have to figure it all out. I just had to articulate where we were going roughly. That is so rewarding, such a payoff. But I say you need to distinguish between those things because there's moments when your team needs you to manage them. Like, do the work assignment. Like Logan, you are accountable for this goal and I will

• 57:15Speaker 01

  hold you accountable. Please come back to me with the underlying metrics that we are going to track. You know, like you are man, I'm managing. I'm making it clear who the owner is. I'm making it clear what the goal is and I'm tracking your progress. And then there are other times where I'm saying, Logan, what your team is delivering is just not good enough right now. And you're like, well, what? Tell me what to do. I'm like, no, you got, because I'm treating you in this case as a leader. I'm like, I'm a leader managing a leader. And I'm like, you're not leading hard enough. Right? And that's very amorphous. I'm not defining it for you, but I just know that it could be better. And I'm challenging you to push your team to make it better.

• 57:54Logan Bartlett?

  Yeah, I've always thought that like, there are innate leaders, or that can come naturally. And management's much more of like a learned skill over time. I never really thought about learning leadership as something that you can, you can do. It's an interesting.

• 58:08Speaker 01

  You can do. And the other thing, I think a lot of leadership is storytelling. And that's another thing you can learn, right? People don't remember all the substance of the plan you articulated as a manager. They remember, yes, you know, Maya Angelou, how they felt, but they remember the stories you told them. And I feel like that's also very learnable.

• 58:32Logan Bartlett?

  Golden rule, treat others the way that you want to be treated, not a great tactic for a manager or a leader. Why is that?

• 58:40Speaker 01

  Yeah, it's too bad because I'm a big believer in the golden rule generally for humans.

• 58:45Logan Bartlett?

  Humanity.

• 58:46Speaker 01

  Yeah, let's treat people the same way we'd like to be treated all around the world. For management and leadership, not a good rule because you as an individual are motivated quite differently than I am, Logan, I bet. Like if you and I sat down and say, what really motivates us? How, what is our, how does our ambition show up? What does success look like for you versus me? Our answers would be pretty different. And so your job, if I'm the manager of these two different people, my job is to kind of interview them. I call it the career conversation, but it's really the, I need to get to know your motivators conversation. Tell me why you made these choices in your career, maybe even in your life. Why did you major in that thing in college? Why did you choose that first job out of college? Why, why, why? What are you, you're trying to get at?

• 59:29Speaker 01

  What are they trying to do? What are they trying to accomplish? What are they trying to learn about themselves? And you're taking that data and you're saying, okay, this is someone, and by the way, this is a very real thing. I have.

• 59:43Speaker 01

  Worked with people and including a child of mine, like some people are motivated by being recognized by positive feedback. Like you're basically cheer, cheer, cheer for all the good stuff. And, and actually, there's a lot of human behavior change that positive feedback, highlighting, these are the things I want more of, is way more effective than nitpicking and the, and the negative. But there are people who I've worked with who are like, tell me the thing I did wrong. Cause I'm so, they're so self-directed. Unfortunately, they're probably a little bit perfectionist, which is not an easy problem to have. It's not an easy burden. But they're so perfectionist that you're like, you know, I thought that, you know, that work you did last year was like, excellent. Like you hit every goal except for that one. And they're like, I know, I'm obsessed. I'm obsessed with that one goal.

• 1:00:29Speaker 01

  And, and like, there are people like that. They're like, trying to get the brass ring all the time. And all you're doing is being like, all right, let's talk about how we get the brass ring. Right. But that, that may not, there was another person who spends the rest of the year demoralized that you pointed out, that they didn't get that one goal out of eight. Right. You gotta know which you're dealing with, or else you could completely undermine them. Uh, so it's about, it's about, um, interviewing them, observing them, collecting data, and managing them differently than you would like to be managed. I mean, what drives me crazy is I manage, there are some people you manage who are obsessed with compensation. And they're really obsessed with compensation because they're keeping score. Cause they want, they're very competitive and that's how they score points. Right. And I'm like,

• 1:01:12Speaker 01

  oh my gosh, I do not want to talk about compensation with people all the time. And you should try to restrict it. But I've come to sort of get zen about it. I'm like, oh, this is just them keeping score. And this is a way they're looking for feedback. And this motivates them. It motivates them to know that yes, there are compensation outcomes for good work. And so we will now talk through that yet again, because that is what they want. And it helps them. And it is not for me.

• 1:01:39Logan Bartlett?

  Yeah, we did away with bonuses and then there is no way of recognizing outperformance. So we put bonuses back and then people were upset about not getting 150% of the bonus target. And I was like, this whole thing's very circular. It just, some people though, they even, it doesn't matter the dollar amount. It's just the recognition that

• 1:01:58Speaker 01

  That's exactly right.

• 1:01:59Logan Bartlett?

  Like that they are doing that good of a job. And that the dollars could be totally nominal.

• 1:02:05Speaker 01

  This is, this is like a worker segment, the scorekeepers. And it is really about that. And they also have their own score in their head. And what they're really checking with you is, do you and I see the same score? I mean, this actually goes almost to the self-awareness gap. Sometimes, yeah, we see the same score and I will celebrate it with you. Yes, you got 150%. But sometimes it's about, okay, why do you think you should get 150%? Are we looking at the same performance? Like, it can be actually a really rich conversation. If you can flip their sort of, like, why are you so obsessed with that score? What's going on there? I mean, especially for high performers, actually. They sometimes need to be challenged even harder than they've been. And they're kind of telling you that in a weird way when they're scorekeeping.

• 1:02:48Speaker 01

  But yeah, compensation headaches on the bonus, bonus in, bonus out is a whole other book.

• 1:02:53Logan Bartlett?

  Yeah, it's a great, yeah.

• 1:02:54Speaker 01

  It's fascinating.

• 1:02:56Logan Bartlett?

  Infinite rabbit hole to go down. Yeah, and how people are incentivized and motivated and all that stuff.

• 1:03:00Speaker 01

  Yes.

• 1:03:01Logan Bartlett?

  What about titles? There's, there's kind of two concepts in Silicon Valley. One is that titles are free, cheap, give them away. And the other one is titles are very, very expensive because it leads to a lot of complications. I get the feeling Stripe was much more on the titles are very expensive. Like, that costs a lot of internal damage dealing with different promotions and hierarchies and all this stuff. Or at least that's what it was in the early days.

• 1:03:25Speaker 01

  Yeah, I mean, Patrick and I really, this was one of the things we aligned on pretty early, which was titles. It's like a little, to me, I'm really going to display my opinion here. Giving out pretty high-level titles in a young, smaller company is a little bit like eating junk food. It feels really good to eat that bag of Cheetos for about 10 minutes. You're like, you know, I love those flavors, you know? And then you're like, oh my God, I just mailed myself a letter bomb. Because if you are sub 40 people, sub 100 even, and you've got a bunch of C-levels.

• 1:04:06Speaker 01

  Are those going to be your chief marketing officer, your chief revenue officer, your C O O even in three? And you're doing well as a company, by the way, in three years, three to five years? Probably not. Maybe a few will scale with you. So you will then have a conversation in front of you where you're saying, actually, you're no longer the C M O. I'm hiring a C M O. And you are a lot more likely to lose that person. Then who might be a really good employee, by the way, but not the C M O. Then if you had just called, you know, called them marketing lead, maybe head of marketing, but. And now I'm bringing, you know, so I think for C level titles, like the, the more you can wait, like,

• 1:04:51Speaker 01

  it's also you look at a small company or like, how can you have that many V Ps? I mean, it's sort of silly looking. Now I totally get sometimes you need a title because that's important for your sales process. But at Stripe, we would sort of try to come up with a title like growth lead or something that was hard for the prospect to, to grok. They'd be like, well, it sounds important. You're like, exactly. Sounds important, but you can't pin me down on exactly what the job is. But I think titles back you into a future corner, essentially.

• 1:05:22Speaker 01

  As you evolve your org structure and it'd be nice not to back yourself into it. I do think we took it too far at Stripe. I'm going to be honest and own that. For example, we got a lot of feedback, which I thought was really legitimate that a lot of the engineer, I mean, it was just like engineer, right? And we did have job levels on the backend. We had sort of level four or five, really senior engineers. But no one knew that except for, you know, the people who were leading those teams. And a bunch of the, the less experienced engineers were like, who are our mentors? Like, who are we supposed to look to? Who, who do we listen to in code review? And we realized, oh, we need to actually, when someone achieves the staff engineer level, which for us is level four,

• 1:06:04Speaker 01

  we should really tell people because one, it's, it is an accomplishment. It is recognition for them. But also it's a signal. This is someone you should watch their work, let, listen to their feedback, use them as a mentor. So that was a miss. And I think there's a similar miss we had on the sales equivalent of that. And so I think there's different, like, there's one thing we're talking about mailing yourself the letter bomb on sort of senior titles of leaders. There's another, which is how do you think about organizational structures? And there's a. We were trying to avoid basically hierarchy. We're trying to do the inclusive thing, right? In the room, if you don't know who's the most senior, everybody's going to show up pretty equally. It's almost a cheat code for inclusivity in a way.

• 1:06:44Speaker 01

  You still have to do the work to get that meeting, to get everyone participating, engaging in that meeting. Let's say it's a meeting. But there's a time when the org starts to get big enough that it's just confusing. Like you're like, I don't even know who to go to. Like, I don't even work with that team. And who do I even call, right? Or who's the best example? But we were trying to avoid also some hierarchical behavior, which just is not what Stripe is about.

• 1:07:08Logan Bartlett?

  We're talking about it from the company side. It's also tough from an employee side as well. It feels good to get called the C level of whatever company you're at. But then weirdly, you might have to take a step back. Let's say you get moved out of that job and you decide to move on to a different company. Now are you addicted to being the CMO or the CRO or the COO, right? But actually, if it were apples to apples versus the next company, you're not C level. And so from the employee side, it actually can be problematic as well.

• 1:07:41Speaker 01

  It can do you a disservice at the wrong moment in your career. It's actually a great point.

• 1:07:46Logan Bartlett?

  Yeah.

• 1:07:46Speaker 01

  People almost won't want to hire you because they're like, well, they're going to want that title.

• 1:07:49Logan Bartlett?

  Yeah, they're going to want a C level. Or what happened in your career where you went from this to that, right? Actually, I've told the story, but one of the, I took a step back when I joined Battery from where I was title wise at investment banking. And I thought, I was like, what am I doing? What is this? Why would I do this? And it was actually the best thing in the world because I got comped against everyone else at this level. And I was a little bit older and a little bit more experienced. And so the apples to apples comparison, I just looked so much better.

• 1:08:15Speaker 01

  You really stood out.

• 1:08:16Logan Bartlett?

  And it was actually a good thing was starting over, right?

• 1:08:19Speaker 01

  And you were in a slightly different field.

• 1:08:20Logan Bartlett?

  A slightly different field. And so, but perceptions are defined early. And if you, if I had had that slight, the higher level, I probably wasn't quite there. And so people would have questioned if I was of that caliber versus I was really good at that level. And it allowed me to accelerate.

• 1:08:36Speaker 01

  By the way, this is another example of like inclusive choices, which is like, actually, you would rather someone, especially moving into a new company, a new kind of role for them, to be exactly in your situation, which is slightly more experienced than the others, but in a learning mode and, you know, much more likely to succeed.

• 1:08:55Logan Bartlett?

  Well, what was your title when you joined Stripe?

• 1:08:58Speaker 01

  Oh, my title was Chief of Business Operations. Yes.

• 1:09:03Logan Bartlett?

  Which, which was because of a similar-ish reason, right?

• 1:09:06Speaker 01

  Yes, there was a, the reason was, we had a lot of conversations about being the COO. And the current, Stripe had a COO at the time, which people forget. And it's funny how companies rewrite their history. People forget that, but my colleague Billy, who's amazing, who is also still with Stripe, but he was the COO and he helped recruit me, which says a lot, by the way, about him and the company. And the parts of the, there were parts of the role where he was like, this is not my, talk about self-awareness. He's like, I'm not a scale, big operations guy. I'm not going to build the sales team. He was really like, he's a brilliant payment strategist, brilliant at like BD and that kind of work, partnerships work.

• 1:09:46Speaker 01

  But point is Billy helped recruit me, but then Patrick and John were like, well, two things happened. I think one is a true founder moment. Two things happened. One was they realized that they'd not told anyone internally that, that this was a decision they'd made, that I was going to be the COO. And they felt if I came in and it looked like I'd taken Billy's job from him, and Billy was very popular, that it would have been, that I would have been unpopular. They're like, we were not setting you up for success. If you walked in the door being like, and I'll just take that title. Thank you very much. And so we kind of made this other innocuous title. And then after about, I don't know, not even that many months in the job, Patrick just, people had gotten to know me though, and seen my work. And Patrick sent out this note like, by the way, Billy's going to be Chief of Business

• 1:10:31Speaker 01

  and Claire's going to be COO. And isn't that great? We all sometimes switch titles and switch responsibilities. And everyone's like, great, you know, it was, it was nothing. The other reason was more, I think John and Patrick had a title, because they were very in the camp of titles, you've got to be stingy with that. They were like, maybe if you could just come in as Head of Business Operations. Like, because I think they got nervous. They're like, this is, it's a big deal to bring someone in as basically COO. And you're trusting, I mean, now I look back, I'm like, that was a big decision for them. I was going to have a big impact on the culture and the results and the outcomes for Stripe. And I think they wanted an out. And but I said to them, I was like, guys, I was like, I think in this case, if you look at my

• 1:11:16Speaker 01

  career and where I'm at in my career and my track record and the conversations we've had, I was like, you do need to give me a title. Like, I'm not going to walk in, I'm not going to leave the job I have at Google for a head of business operations job at your company. And they're like, yeah, right. Okay.

• 1:11:33Logan Bartlett?

  Yeah, it's a balance. It's a balance. Now, one of the things I heard you say, too many companies make their principles so idealistic that they don't resonate with employees because they have no connection to how the company actually operates. How do you think about principles in general for companies and like how to make them balance tangibility with the idealism?

• 1:11:55Speaker 01

  Yeah, so we're talking about Stripe calls them operating principles. Some companies call them values. I mean, the first thing I'll say is there's a lot of work that needs to be like before you get to some of the content in my book, you're you're just trying to stay alive. You're looking for product market fit. There's a lot of stuff you could start to build for that. Like, it's product building more than company building. And really, that's the right place to focus. Like, you shouldn't have a long term goals because you're just like trying to make it the next

• 1:12:20Logan Bartlett?

  Surviving is your long term goal.

• 1:12:22Speaker 01

  Right. And so then, though, you start to get traction. You should got check, is it real? And this is where it's good to have investors and advisors and like, it feels like this is real. And all of a sudden, whoa, you got to think about, I think I might be building a company here because we have a product and people are buying it and ARR is X or whatever metric, you can be the expert, Logan, on on what benchmarks you want to start to see. And so then, as the leader, you're thinking, all right, so for company building, I think there's a set of things you want to start to put in place. And and this is where a lot of the early chapters of my book, the operating structures. But one of them that I argue is really important, again, at this point more, are these founding documents, including articulating what are your your company values? And if I was going to simplify it, I'd say,

• 1:13:06Speaker 01

  look, start with what's your mission slash vision, which is the why? Why do we exist? And by the way, why you exist is probably beyond that initial product that you've built. It's a bigger vision that you have. And you may not exactly know it all, but this is it's time to start thinking about it. Because it's going to matter to people that you bring on board. Right? So, you know, why are we in the world today? Employees care about this. So why do we exist? What's our mission? And then the next thing is the how. How do we want to work together? And this is where the values are. Like, what do we value? When the chips are down, are we going to choose the user? Or are we going to choose our growth? You know, by the way, sometimes you'll have those choices. And you really want to have established when we make hard decisions,

• 1:13:51Speaker 01

  what are the values we're using? And sometimes you can inductively get there. You can look at some hard decisions you made and say, oh, it's interesting. What we really valued, by the way, was speed maybe over quality. I don't, there's no judgment from me. But the thing that I see too often, which you alluded to, Logan, is that someone, executive team, a founder, even a focus group in a company, sits down and writes a bunch of values that are really aspirational. Like, customers first is a common value. I'll be honest, like, Google was not a particularly customer-oriented company. And would sometimes talk about being one. And I would be like, but we're not really.

• 1:14:31Speaker 01

  Like, we're actually about the technology first and the customers later. And so no judgment. Like, I actually think, but just kind of own it. Like, own what your actual values are. And if they're too aspirational and they don't resonate with employees or with your customers, by the way, eventually, it's going to actually undermine you. It'd be better to have none, in my opinion. So, you know, this is the sort of, there's the mother had an apple pie version of this, which is like, they're so abstracted up that you're like, yes, we collaborate well. I mean, yeah, everyone wants to collaborate well. If they can be kind of specific and kind of true and even stack ranked, like, what do we value? It's a really good exercise.

• 1:15:14Speaker 01

  I wouldn't overdo it or overthink it. But try, one thing we did at Stripe when we wrote the initial draft was we came up with stories and examples of those values in practice. And there were a few where we were like, hmm, we don't have a lot of examples. Maybe this isn't a value. Maybe it's something we want it to be true. And then we actually had to think about, how do we make this more true? Right? Or some that we put out there got misinterpreted.

• 1:15:39Logan Bartlett?

  And sometimes weaponized, right?

• 1:15:41Speaker 01

  Yes. Oh, yes. There was, there's few, I feel like I've suppressed them at this point, but we had some around trust and people were really interpreting with something along the lines like trust but verified. There was a lot of verification going on, not, not as much trust. Or we had the, does it pass the front page test, which is really about integrity and ethics. But people, I think, kind of turned it into like a more broad application of, oh, we can't do that. What if it was on the front page? And it's like, well, no, it's like, you can still be bold. Like, you want to be on the front page sometimes.

• 1:16:18Logan Bartlett?

  I'm just saying.

• 1:16:19Speaker 01

  You don't want to be arrested.

• 1:16:21Logan Bartlett?

  I'm just saying the thing that you think I cannot say. It's like, you're being an asshole.

• 1:16:24Speaker 01

  Yeah, exactly.

• 1:16:25Logan Bartlett?

  You're being a jerk, actually, is what you're doing.

• 1:16:27Speaker 01

  Exactly. So really try to apply the values and see if they, if they stick.

• 1:16:30Logan Bartlett?

  It's interesting because everything does have, there's two sides of every coin, right? And if we were to say, we're founders first, right? And Founder's Fund does a great job. They say they're founders first. Now, that comes at times at the expense of limited partners, right? That is a, there's, there's two sides to these. You can't just say platitudes without thinking through the other side of that, right? And there's everything, it's not hollow. It sounds hollow to say, oh, we're founders first, or like Google, we're customers first. Are you though? Are you actually customers first? When push comes to shove, and you have to make a technological trade off of what the future roadmap's going to be, and it's going to piss off a bunch of customers, are

• 1:17:13Logan Bartlett?

  you actually customer first, right? And there's no real platitudes. All these things have another side of the coin.

• 1:17:17Speaker 01

  And then that's when you know you have a good one because it has an edge. You're like, this is going to have a downside at some point. We are going to have a decision we have to make that it's going to hurt. I say a strategy should hurt, so should some of your values. Should feel pretty painful, but it should be, I mean, Patrick, in a different context, and I talked about this, I talked to him a lot about. Expectations of leaders and how they should, they should be higher. And this is a sort of behavioral expectations, leaders, you know, ethics expectations. And I said, there's going to be a time when a leader who we highly value, who's incredibly talented and incredibly impactful, does something humanly with poor judgment. And you all can color in whatever story that is. And I said, and I will tell you, it is going to hurt like hell, but we should, they should,

• 1:18:02Speaker 01

  if it's bad enough, they should leave, even if they're the best person at that job. And he was like, and we actually like went pretty deep on examples I'd seen and what I thought, because culturally you've then taken someone who you've elevated to a leadership role and they've done something like with horribly bad judgment and said, it's okay. And even if it's private, it still gets known. In my opinion, at a big enough company, it still gets known. And we kind of locked arms on it and we had to act on it. Okay, you know, there's times when you're like, oh my goodness. And now we're like, it feels like you're stabbing yourself, but you're not. In the long term, you're live, you're honoring the culture you're trying to set.

• 1:18:41Logan Bartlett?

  Yeah.

• 1:18:41Speaker 01

  Which is we hold leaders to a higher bar.

• 1:18:43Logan Bartlett?

  Sometimes you need to have surgery to, you know, if you tear your ACL, you have to have surgery to rehab yourself forward, right?

• 1:18:50Speaker 01

  Yeah.

• 1:18:50Logan Bartlett?

  And it could be painful.

• 1:18:52Speaker 01

  It's not like the payoff is tomorrow.

• 1:18:54Logan Bartlett?

  No.

• 1:18:54Speaker 01

  It actually hurts soon.

• 1:18:55Logan Bartlett?

  It's a long time in the future.

• 1:18:57Speaker 01

  Yes.

• 1:18:57Logan Bartlett?

  Now, don't let perfect be the enemy of good. I know that's something you believe and I happen to share. How do you think that manifests itself in like startup and high output companies?

• 1:19:08Speaker 01

  Yeah, I think there's this continuum that is so interesting. And you probably see, you see more companies than I do where the sort of move fast and break things, Facebook, whatever. And then there's the perfect is the, is actually starting to kill the good. And I think that some companies, and it's really about the founders and their. Their proclivities or their instincts, their defaults, which is our get, I'm not saying analysis paralysis, but like are so intelligent. Often they think of so many angles. They're trying to preserve optionality and they're like, hmm, how do I get more data? How do I know? Who do I also check with? Like, you know, and they're making some decisions or choices for the first time in their lives and they're waiting or they're waiting for

• 1:19:53Speaker 01

  this candidate who's perfect, right? And you can be too far on that continuum and you can also be too far on the, you know, outcome be damned. I am running up the mountain and I don't care who I hurt. And that could be a user, a partner, you know, you could have bad behavior, but you're getting the goal, you know, like that's also not good. That is, you know, not even the good being the enemy of, of the, you know, I don't know, the bad winning in that case. So I think on that continuum, being aware of where you fall, this is self-awareness, actually, in the end, be aware of where you fall in like in your defaults as a founding team, as an executive team, and then think about how do I push myself? How do I make sure I don't fall on the wrong side of that? That I'm way often for the perfect being the enemy of the good. It's like taking too long to make

• 1:20:37Speaker 01

  a decision, to make a hire, to, to sign a partnership. Like you're gonna, there's this quote from either Hewlett or Packard, which is after a certain point, there are some companies that die more of indigestion than starvation. I think perfect being the enemy of the good is like you've gotten to product market fit, you're starting to steam ahead, and then all of a sudden you're starting to die of indigestion. You cannot get stuff through the system because you're just examining every damn thing too closely.

• 1:21:04Logan Bartlett?

  And it's important to analyze yourself and where you fall. And then not every end market is going to be the same either, right? I would be glad self-driving cars take a little bit of time to be perfect or and roll.

• 1:21:15Speaker 01

  I was just gonna, I was just gonna bring that up. Yeah. It does depend on your market and who your customers are and what they, I mean, gosh, Stripe's dealing with payments. We better be on that side of the continuum. And we are. But sometimes we flip too far over to like, ooh.

• 1:21:29Logan Bartlett?

  Yeah. If you're Canban board, a workflow software, you can get by a little bit more.

• 1:21:33Speaker 01

  Right. But I was actually, I was in this funny, I was at a conference, running a roundtable discussion as a breakout. This was with another venture capital firm sponsored this, but it was all founders. We were all talking and it was me and a couple of leaders from some other companies talking to a group of founders. And I was saying how when the chips are down at Stripe. If we are doing a launch review for something, we may have even publicly said we're launching, maybe at least to some customers, and we don't think the quality is there, we will delay the launch. Like, there is no question. And if you think about it, yeah, we're dealing with people's money with payments. If we don't like, and even if it works, but we don't like the quality and the craftsmanship, that's also what we like to be known for, right? We'll delay the launch.

• 1:22:15Speaker 01

  And this guy across the room from another, I'm not going to name the company, starts laughing. He's like, are you kidding? And I was like, yeah. He's like, we would do the opposite. If we weren't liking something, we would move the launch date up. I was like, excuse me? He's like, well, we have this whole idea of these test markets. And he named a city in Canada. He's like, if you live in Canada, you have seen some crazy stuff from our product. I was like, are you serious? And he was like, oh, yeah, we'll move it up because we're trying to understand, like, why is it not working the way it should?

• 1:22:43Logan Bartlett?

  Hopefully, this business isn't healthcare or self-driving.

• 1:22:46Speaker 01

  It's not a safety critical system. But the founders were like, watching us like we were playing tennis match. And I think it was actually probably the best thing that could have happened. Because it was like, these are equally reasonable choices that you make in the face of something that you're not happy about launching. And it really depends on your product, your market, but also your appetite for risk, who you are, your value system. And by the way, good on them that they have some test markets that they learn from, right? Like, I was kind of jealous. But like this-

• 1:23:18Logan Bartlett?

  Sorry, Canada.

• 1:23:19Speaker 01

  Yeah, yeah. Sorry to that one city in Canada. But you know, I think that that's, that's what's kind of fun about working with different companies in different markets. But the key is self-awareness. Know where you fall. And then, to the point we talked about earlier, have some people around you who will call it when they think you're dying of indigestion.

• 1:23:38Logan Bartlett?

  You'd said leadership is disappointing people at the rate that they can absorb. And I, I guess it's an interesting line. I actually didn't know what you meant by it. What does that mean?

• 1:23:49Speaker 01

  This is a quote from Ron Heifetz, and also probably Marty Linsky. These are some, some researchers, academics, and I guess, sort of, leadership gurus at this point, who've written about adaptive leadership, which I actually, back to books that are worth checking out. I think some of Heifetz and Linsky's work on adaptive leadership is worth checking out. Because it's about, like, distinguishing between the fact there's technical, this is almost management versus leadership. There are technical problems, like, we can't meet our SLAs. You can work your way to fixing that problem. There is like not a right or perfect answer, but there's answers. Adaptive problems never stop. Like you are never like something is happening in the competitive landscape. Always like it is adaptive.

• 1:24:33Speaker 01

  Or is your go to market product interlock? Perfect. No, it is never perfect. You'll be adapting constantly. Right. And getting comfortable as a leader with adaptive problems. And they talk about various tactics, like one of their favorite ones is how do you get up on the balcony and observe the problem and then get on the dance floor and interact with it. But being able to do both of those things at different times really helps you as a leader to adapt because you are going to have to keep iterating. Right. To to work this problem forever. Uh, it's like infinite systems essentially. Right. So, uh, leadership is disappointing people at a rate they can absorb. Is one of their quotes, and I didn't have it in the original book. And then someone who used to work with me at Google was an early reader and he and I were, he was giving me my feedback, which was great. And he said, you know, it's funny.

• 1:25:18Speaker 01

  I remember we were in this meeting where you shared that quote because you've been, I'd been reading, I'd been a learner about adaptive leadership. And he said, and it's like, it stunned me. And I thought about it the rest of my life since then. And it's interesting because in the book, a lot of people have picked up on this and they're like, I really want to talk about that. And I think it's because we think of leaders as superheroes. Right. We think of them as these people who don't disappoint us. They inspire us, don't they? And actually, uh, leadership is is often disappointing people. You do become a little bit mythic, especially the founders, right? You become bigger than who you are as a human. And you aren't perfect. And if you start thinking you are, you're going to have the other problems.

• 1:26:02Speaker 01

  And I think one of the biggest ways leaders aren't perfect is we talked about this. You set a vision. You don't even know how you're going to get there. You're like, we're gonna. Completely pivot our company to this brand new product line and launch it in the next six months. Right. You're setting this vision. You don't have all the details. You're expecting your team to one, follow you, which you better have some skills to get that to happen. And two, to color in the lines to get that whole pivot to that new product line done in the next six months. And you've told a customer, by the way, leaders often do that. They, they announce things. It's like burning the boats. And, and you're Alexander Gray, just burn the frigging boats. So you can't go back. Right. So, so that is leadership and leadership is uncomfortable and it makes people uncomfortable. And by the way, it's not perfect. Guess what?

• 1:26:45Speaker 01

  I bet that pivot to that new product line took 12 months or 18, right? And people are sitting there thinking, hey, we didn't get it done. But actually, as a leader, you're like, oh my God, but we are doing it.

• 1:26:56Logan Bartlett?

  Totally.

• 1:26:57Speaker 01

  But you are a little disappointed. Or in other ways, you disappoint people is you get them really excited about following you and spending time with you. And then guess what? You can't spend time with everyone. You're going to disappoint them with your time because you cannot give it to everybody. You are still a human being. And I think that's what I mean about living with that discomfort is a lot about learning to be a better leader. Some of it is setting the bar and the inspiration and some of that is not showing up perfectly. And giving yourself permission to realize that's okay. It's going to happen. I mean, one, one woman who I'd mentored at Stripe and who went on to a pretty senior role in a very successful sort of younger company that's in a growth stage called me

• 1:27:42Speaker 01

  not that long after she took her role and she was, she was like, oh my God, how did you live with the fact that everything is broken all the time, every day? Cause she elevated to a point where she saw what the equivalent of me saw in early Stripe. And I was like, oh yeah, welcome to the tarot dome. Everything is broken. Nothing is perfect. And if you are motivated as a leader by fixing everything quickly and it being perfect, you will. Die like this is not, this is not the next three years of your life. The next three years are, are, are living with a lot of discomfort and imperfection.

• 1:28:16Logan Bartlett?

  What is?

• 1:28:17Speaker 01

  But never, never releasing the bar, right?

• 1:28:19Logan Bartlett?

  Yes.

• 1:28:19Speaker 01

  Keep holding the bar.

• 1:28:21Logan Bartlett?

  What does don't leave ice cream on the counter for too long mean?

• 1:28:24Speaker 01

  Oh, I think this is such a great analogy. Uh, and this is from a business school professor of mine who sadly died last year at a pretty young age. Her name was Sagal Barced and she was trying to teach like change management is a hard, hard thing to teach. It's actually a thing you need to spend energy on and think about and, and plan and build processes. Like I can't just pivot to the new product line. You can't just reorg the whole company. You have to think about the change management, not just to propose the change, but who to tell and then how to cement the change. Right? And so her analogy was this, the minute you start the change and that start could be just telling a few people about it. It's like, you know, at your house, when you take the ice cream out and you put it on the counter because you're going to scoop some ice cream. Then you get distracted and you're like finding out which flavor people want and you leave it and it gets like a little melty.

• 1:29:10Speaker 01

  And kinda looks a little gross. And then you put it back in the freezer and it's never quite the same because it got weirdly like the consist. I mean, there's, I'm sure some food chemist is listening to this, like there's a reason for that.

• 1:29:21Logan Bartlett?

  Yes, yes.

• 1:29:22Speaker 01

  Anyway, um, she's like, if you start the change and you leave that out hanging in the wind without all the decisions or the communications or the, you haven't started to cement it, you will, you could irreparably affect some things culturally uh, or in your team's stability. And, and so I, I actually introduced that analogy to the Stripe, uh, leadership team early on in my tenure. I don't know, it always stuck with me and a few people still to this day will be like, oh my gosh, ice cream's on the counter. Ice cream's on the counter. We gotta finish, like we gotta see this change through. Uh, and I think it's just, it's a good watch out.

• 1:30:00Logan Bartlett?

  So you wrote this book, it was published in April?

• 1:30:04Speaker 01

  March of, yeah, 2023. Yep.

• 1:30:07Logan Bartlett?

  And, uh, I heard you say, one of the things that you've only gained conviction in since doing it was, uh, to manage people out of seats earlier. Once, once you sort of have that conviction and I think it ties to this ice cream.

• 1:30:23Speaker 01

  Yeah, it does. It's a different version of that.

• 1:30:25Logan Bartlett?

  A different version of it. Can you, can you expound on that, that concept and thought?

• 1:30:31Speaker 01

  Uh, yes. So it's a great, it's a great connection you're making. You know, I think what I've gained more conviction, I mean, in I knew Patrick and John read the book the earlier, the earliest manuscript version I had they could read. And I mean, phew, Patrick's like, yes, this is what I was picturing because he really wanted me to write the book. And I was like, I don't even know if we're talking about the same.

• 1:30:53Logan Bartlett?

  Well, so maybe, maybe use this as an interlude of, so, so you wrote a section of a book for, for Eli Gill, who's been on the podcast before, High Growth Handbook, you wrote a second chapter in that, and it was well received.

• 1:31:03Speaker 01

  Yes. So, yeah, so I did this chapter in Eli Gill's book, High Growth Handbook, which was our bestselling Stripe Press book, because I think it's a great book, by the way, and highly recommend it. And my chapter, even though I was definitely one of the lesser known contributors to that book, in terms of tech luminary types, got a lot of traction because I think it was very tactical and concrete in a way that's maybe, you know, it's hard. Management leadership advice is often abstract. You're like, how do I actually do the thing? And so I did some of that discussion in Eli's chapter. It got some traction. I also, there's like a YouTube video of me how to run an effective meeting that's got some many millions of views, which I find scary and fascinating.

• 1:31:43Logan Bartlett?

  Kozlo's conference.

• 1:31:44Speaker 01

  Yes, I did it at a Kozlo conference. Yes. And that got a lot of traction. I mean, I went once to a wedding and, and I got introduced to this guy who's a prominent academic and he was like, oh, I know you from your meetings video. I was like, weird. Okay. Nice to meet you. But point is Patrick observed those things. But also John and Patrick observed that a lot of Stripe, a lot of Stripe customers are really interesting companies that are growing quickly around the world, wanted to spend time with me on their scaling stuff, and less on payments and Stripe's products, which would drive us a little crazy. But I was like, hey, I'm happy to have dinner with them. I'm happy to talk about it. And Patrick's like, you just have to write the stuff down. And I said, I don't know that I'm the right person to write this book. But yes, wrote it. And it came out in March.

• 1:32:29Speaker 01

  I knew that he was cringing. There's a section on managing people out and firing people. And I talk about how long it can take. And I say, look, it's not going to be one conversation. And the more senior the person is, by the way, the longer it can take. And I think that makes sense to everyone. It's like they've got a whole team. They've got an org. You spend all this time hiring them. They've had a successful career. Can they course correct? There's costs. There's a high cost. And so I talk about, you know, 30 days, 60 days. And Patrick and I joked, because I said, I got in front of it. I said, I know you're cringing at the section on how long it can take to get someone out. And he's like, yeah, you know, I am because he he's of the mind like the faster, the better. And I think now that he's managed more senior people for longer, he realizes this is not always the fastest path.

• 1:33:15Speaker 01

  But I sit on a lot of boards now. I mean, you probably sit on a lot of boards. But when you get 30,000, 10, I mean, 10 to 25,000 feet away from a company and you're talking to the CEO, the founder, you're sitting with the executive team. And there's clearly a leadership issue in one department. And you it's like so, it feels like someone is painting neon paint on this person for me now. I'm like, oh, my gosh, this is holding the whole company back. Holy crap, we have got to move. You know, it's really interesting. You get much more clarity on how critical it is to address when you've got some separation from it. So that's why I really have more conviction.

• 1:33:59Speaker 01

  It's because since writing the book and since I changed my role at Stripe, I've gotten involved with a lot more organizations, not just companies, you know, nonprofits, schools, you name it. And I'm like, having an issue in, and I don't care if it's your team of individual contributors or it is your executive team, but I'm talking about in the executive level, having a performance issue is a killer.

• 1:34:20Logan Bartlett?

  I've never seen it come back around. I'm sure it has.

• 1:34:22Speaker 01

  No one ever says, I wish I'd moved more slowly.

• 1:34:25Logan Bartlett?

  It's never happened, which means, which means our bias, we need to overcome our bias to keep someone around and give them a chance.

• 1:34:33Speaker 01

  And by the way, the key is, I still think, and I talk in the book, you can do this with empathy. You can do this with good, honest, direct, open conversations in most circumstances. Some of these go sideways and it will cost you money usually. But I, I just think if you're not talking directly to the person about we have a, there's a, I'm worried. We have a problem. You are doing them a disservice and as I see now, you are killing yourself on your, your strategy.

• 1:34:59Logan Bartlett?

  Well, and, and.

• 1:35:00Speaker 01

  And probably the team people under them.

• 1:35:01Logan Bartlett?

  Well, I was just about to say, great people hate mediocrity.

• 1:35:04Speaker 01

  Yes.

• 1:35:04Logan Bartlett?

  And if they're seeing, saying, hey, this is acceptable.

• 1:35:06Speaker 01

  It's a killer.

• 1:35:07Logan Bartlett?

  Here, it kills their perspective on it. And, and the people, thing people will delude themselves into thinking is that you're being fair to the person that you've made the decision on. I'll give them more time so that they can get settled. And that's actually.

• 1:35:21Speaker 01

  Or that you're keeping things stable for their team.

• 1:35:24Logan Bartlett?

  It's supremely unfair, right? It's actually, that person should be given an opportunity to go to a business that doesn't

• 1:35:30Speaker 01

  Yes.

• 1:35:30Logan Bartlett?

  have the, all the questions.

• 1:35:31Speaker 01

  Doesn't believe it.

• 1:35:32Logan Bartlett?

  Inevitably ready to get rid of them.

• 1:35:33Speaker 01

  And their team will be happier with a leader who's got, by the way, the confidence of the CEO. Like that is a real problem. If you're on a team where you're like, person managing you isn't trusted. You've, you may not know it, but you feel it unconsciously. I will say, we're talking about, I mean, I don't know, maybe. Obviously if you've a hundred percent know someone needs to leave, then you're moving them out. But we're talking to the.

• 1:35:56Logan Bartlett?

  It's always a gradient.

• 1:35:57Speaker 01

  Where, yeah, we're talking about a gradient here. I do think it's hard when there's someone who's clearly not the best. And those are the ones that actually drag out more. And maybe my conviction is more. You know, in your heart of hearts, if it's going to work or not.

• 1:36:12Logan Bartlett?

  Yeah.

• 1:36:13Speaker 01

  And you've got to start trusting your gut and moving.

• 1:36:15Logan Bartlett?

  And the hardest part about that is if they were the right person for six months ago in the company, but the company's growth has outpaced where they are. That's when it's particularly.

• 1:36:24Speaker 01

  And you've started to have that. A lot of this is stuff, I mean, I'm sounding like a weird Californian and I'm now back on the East Coast. So I want to say I'm not a weird Californian, but you know, in your body. Like it's a weird thing. Like you'll be like six months ago.

• 1:36:38Logan Bartlett?

  You feel it in your.

• 1:36:38Speaker 01

  Yeah, you're feeling, no, but you're like in the room and you're a little uncomfortable.

• 1:36:41Logan Bartlett?

  Yeah.

• 1:36:41Speaker 01

  And like six months ago, I was fine. Like our executive team meeting was fine. And that's probably true, by the way. And then all of a sudden you're not. Feeling it.

• 1:36:49Logan Bartlett?

  Yeah.

• 1:36:50Speaker 01

  And you gotta like, listen to the feelings.

• 1:36:52Logan Bartlett?

  Now, you referenced me on a bunch of boards. You're on Hallmark's board.

• 1:36:55Speaker 01

  I was on Hallmark's board. I was.

• 1:36:57Logan Bartlett?

  But that was a purposeful decision. It's an unusual.

• 1:37:01Speaker 01

  It was a personal development decision.

• 1:37:04Logan Bartlett?

  And can you talk a little bit about like, being on a board of a company that has been built to last?

• 1:37:10Speaker 01

  Over a hundred year old company.

• 1:37:11Logan Bartlett?

  So what did you learn from being on something that has been that endurable?

• 1:37:17Speaker 01

  Yeah, I mean, Hallmark was interesting to me because, well, one, if you're at Google as an executive, Google is supportive of you joining boards. Not every big company is actually, which I appreciate. However, you can't join a board that is a competitor, competitive in any way to any of Google products, which eliminates a lot of companies.

• 1:37:35Logan Bartlett?

  A high percentage of the world.

• 1:37:36Speaker 01

  So I want to own that, first of all. But Hallmark was interesting because I don't think there's enough respect paid, especially in Silicon Valley, but in tech generally.

• 1:37:46Speaker 01

  Some, some people are the exception to this, but to look at companies that have existed for eighty, a hundred, a hundred and twenty years, there actually aren't that many in the world. There's like a soy sauce company, there's Caswell and Massey, it's like a soap company. Like, we should study them because that is a sustainable, not just business, like you built a business that has sustained and had revenue and had growth for a hundred years, but often also the culture through multiple generations of leaders and well past founders, by the way, that's, that's astonishing. Like, how do we harness what's happening in those companies? So Hallmark became really interesting to me. It was also is interesting because it runs like a public company, but it was private, which meant less time commitment, but actually has a meaningful amount of revenue,

• 1:38:31Speaker 01

  which is private, but in the billions of dollars of revenue, owned a media company, Crown Media, that I think we all love our Hallmark movies and the Hallmark Channel, owned Crayola, which is actually a very interesting company they bought in the 1980s. And then obviously the core Hallmark cards business, which you would say, oh, well, isn't that a dying thing? Right? That's an interesting thing to think about. It's like a very, there's only a few players. It's kind of an oligopoly. So it's actually competitively really interesting, creating cards, weirdly, I learned. But, but I, I was most interested in how had they structured succession planning, multi-generational strategy planning, actually sitting in the moment where technology was disrupting elements of their business.

• 1:39:16Speaker 01

  What were they going to do with that? And one of the big things we did is that Crown Media, the media properties, which is the content, and I think you know well, but content is very at a pre- is fragmented, but it's at a premium, good content. Crown Media was public, and so we took it private. So we didn't own, we owned like 96% of it. But that was one of the biggest decisions as a board was like, we have to own our own destiny and our content is going to matter to us more than, whereas the greeting card business sort of mattered more, right? Like it was like the media business actually matters quite a lot, but only if you can control it. So, so it was just, it was really good to take me out of Silicon Valley, put me in a situation, by the way, also, oh my gosh, the legacy systems have a stranglehold on these companies

• 1:40:00Speaker 01

  that have been around a long time. And you realize like how, these are smart, that's another thing. Silicon Valley is like, well, these, what's wrong with these leaders, these executives of these companies? Why don't they get themselves like, just rip up your stack, put in, you know, like move it to the cloud, you idiots, right? Like, we all think that. We're like, what's wrong with them? They must not be smart. Guess what? Really smart, really competent people, a bunch of amazing leaders I would work with at Hallmark. And I was like, geez, I was really judgmental. I was not being open minded. And they are like fighting a war with like two hands and one leg tied behind their back. Because ripping out those systems is so disruptive and like, it's just like really existential threat

• 1:40:44Speaker 01

  to the business, especially if you've got physical goods. Like, oh, how, I mean, it's a total Jenga game that is way more complicated than you realize. And it was really like hurts your head when you think about it, but very instructive when you're trying to sell B2B and sell SaaS. And you're like, oh, I see.

• 1:41:01Logan Bartlett?

  You just explained why IBM's still in business.

• 1:41:03Speaker 01

  Why they don't get that. Yeah, it's exactly, they get that they need a different solution. It's how they get to there that is brutal. So that was really, really helpful. But yeah, I sit on a bunch of boards of actually different stage companies and some not companies. I'm actually spending time on, I'm on the board of the Atlantic. Uh, which is used to be the Atlantic Monthly. It's publication. It's won the National Magazine Award the last two years. I had nothing to do with that. Uh, I'm on more the business side of things, but I'm going to visit with them tomorrow. Uh, but yeah, I, I, I think it's really, I mean, I will say as a development thing, Patrick and I talk about this, like it's really good to try to be on, I mean, it's hard because it's time consuming. It's a commitment, but to see for me,

• 1:41:45Speaker 01

  be on the Hallmark board, I mean, in the other side of the table from the executive, from the operators, I immediately was like, oh my gosh, when I'm presenting to the board, I'm going into way too much detail. I was like, I am not, Brian Halligan, we were talking about Brian at the beginning of this, who's the founder and the chair of, of the HubSpot board, previously CEO. We have a new board member who's like, you really shouldn't be talking about so much how in your meeting, right? You should talk about the, the why and maybe the what to a point. But like, if you're talking about a lot of tactics, a lot of operational detail, something's wrong.

• 1:42:23Logan Bartlett?

  There's better places to get feedback.

• 1:42:24Speaker 01

  There's better places, yeah, for the board. Like you're also inviting, by the way, you don't want to invite me, an operator into the how details because I'll be like, oh, what about this? Have you tried that? And then you're not talking about the stuff that moves the needle for the business, right?

• 1:42:38Logan Bartlett?

  Now, we, uh, I think we both have places to be at some point here in the next couple hours. So I, I, as succinctly as you can, what makes the Collisons so special?

• 1:42:49Speaker 01

  Um, Patrick and John Collison are really multi-dimensional humans. Uh, and they're very different from each other, I think, but have, they're sort of like a Venn diagram where they're very complimentary in certain ways. And I think obviously have some shared values, which is a good foundation to have. But, um, high IQ, high EQ, a different kinds of EQ, but really curious learners, very ambitious, but humble.

• 1:43:19Speaker 01

  Uh, comfortable that they don't know everything and, and really oh excited about others teaching them and giving them feedback. Um, and a lot of vision, like I, I think the amount of energy they both bring, but in different ways to they discover a problems, you know, you discover a problem space and I'll say this as, as someone who's like had a few years under my belt. I'm like, oh my gosh, I'm exhausted. Like, am I really going to go fix that? I just, I, I think the energy level for tackling really horrifically heinous problem spaces is, is amazing to see and sustained. They both sustain it, the level

• 1:43:59Speaker 01

  of commitment to that. Um, and, and I don't know, I think there's an element of, you know, solving problems they themselves faced as engineers and doing that at a scale. I, I, I think they have not gotten cynical about that, that that feels like an important responsibility that they have. And I really appreciate that too. Uh, and just, just flat out super intelligent people.

• 1:44:23Logan Bartlett?

  Yes.

• 1:44:24Speaker 01

  I mean, let's not kid ourselves.

• 1:44:25Logan Bartlett?

  Yes, yes. They're in a rare.

• 1:44:27Speaker 01

  But you can be really intelligent and not respect others and others contributions at intelligence and they're the opposite.

• 1:44:33Logan Bartlett?

  There's, there's a lot of different types of intelligence,

• 1:44:35Speaker 01

  Yes.

• 1:44:35Logan Bartlett?

  which is something I've found more and more.

• 1:44:37Speaker 01

  There, absolutely.

• 1:44:40Logan Bartlett?

  I, I thought it was all SATs and GPA once upon a time, and that is not just intelligence. Um, I, I want to back up, uh, and talk about, I guess your, your parents, but your dad in particular, instilling in a value of autonomy to you at a young age. So he had you shing, uh, shingle your roof, uh, taught you how to fix a car.

• 1:44:59Speaker 01

  Yeah. To a point, let's.

• 1:45:01Logan Bartlett?

  Never had you, yeah, maybe that build a car.

• 1:45:03Speaker 01

  Yes.

• 1:45:04Logan Bartlett?

  Never helped you with your luggage or suitcase.

• 1:45:07Speaker 01

  Yes, yes. There's a family rule. You pack it, you carry it.

• 1:45:10Logan Bartlett?

  Can you talk about like how those little things, uh, impacted who you are today?

• 1:45:16Speaker 01

  Yeah, I think, I mean, and my parents are both teachers. And I think another thing is, if you aren't contributing to the conversation, this goes to the sort of say the thing you think you cannot say, or are just confidence generally, you kind of can't leave the dinner table. Like, you better add some value. And that's

• 1:45:33Logan Bartlett?

  Especially if you went to business school and you were the black sheep in the family.

• 1:45:36Speaker 01

  I know, I know, it was very unpopular when I went to business school. It's not very intellectually deep of me. But at the dinner table conversation, I had to, I had to carry my weight. And I think that taught me from a young age to think about what I'm saying and have ideas and share them, which, you know, helps when your parents are teachers, because that's what they're doing, is bringing that out of young people, which is what you hope teachers are doing. But how do you, um, yeah, it's sort of a combination of confidence, interested in learning and sharing ideas, and being feeling comfortable being independent. I do think as a parent, I fail someone this, which is, your kids can do a lot for themselves.

• 1:46:19Speaker 01

  But a lot of parents don't ask them to, or don't expect them to. And I think my parents were busy with their lives and their careers. That's one of the benefits of having two working parents, I think. And I, I had to get figure my own stuff out. Like, I planned my whole, I'm laughing now, because I've just been working with my daughter on her college visits. And I planned my whole thing. I scheduled my visits. I scheduled, at the time, there were, used to be interviews for colleges. There's not as much anymore. And I'm looking at like, hmm, am I an enabler? I am. Oh, no, I'm not listening to my own advice. You and I were talking about, sometimes you give good advice and you don't always take it. But

• 1:46:57Logan Bartlett?

  That's being a VC.

• 1:46:58Speaker 01

  But that's being VC. That's your, your secret tagline. We give great advice, we just don't take our own advice, right? But I, I really value, you know, my father's not with us anymore, but he

• 1:47:14Speaker 01

  Talk about people who had no biases. Like, he believed that every human, you could do something interesting with your life. And he expected it of us. And I think that's one of the best things you can do for other people.

• 1:47:25Logan Bartlett?

  And to the point of, he also, back to the victim mindset, right? You've told the story of him being robbed at gunpoint in Paris, was it?

• 1:47:36Speaker 01

  I don't think it was a gun. I think he was just mugged, but like, meaning jostled in the metro. And yeah, totally like, in retrospect, I'm like, how horrible would that have been to lose like your wallet? Your ID, you're in a foreign country. And he was just like, yep, should have been smarter. He like totally took responsibility and just dealt with it. And somehow we got home. I guess I think he didn't lose his passport, but I was young. But I remember, like, if you think about how you react to something like that and watching your parent react to what is one might view as a failure, or at least something really bad happening, such resilience, like such, I'm gonna take responsibility. I'm gonna do what I can do, what I can control, control what I can control.

• 1:48:22Speaker 01

  Is, it's amazing, again, I think, leading, especially young companies, is a lot like parenting, which is it's not so much what you say, right? You say, you try to say the right things, of course. It's your behaviors, your actions, and even your emotional reactions when under stress. That is what people are really watching and they're taking their cues from. And I would say both my parents really had a lot of resilience and personal accountability and believed in sort of independence. And I watched that from a young age and I experienced it.

• 1:48:55Logan Bartlett?

  I, the, the, the story that you've shared, I think is an important one, if you're comfortable sharing it, of the Google layoffs and just balancing work. We spent a ton of time talking about operating practices and all this, but when you zoom out, what actually is important in life, if you're comfortable telling the story of the Google layoffs and your father's birthday party.

• 1:49:22Speaker 01

  The thing to think about is And there's some, like, I think there, I was at a dinner on Sunday night with a bunch of educators who were talking about how they've had a set of employees that they've hired, who are sort of of the latest generation, every generation's criticizing the younger generation. Oh, totally. But they're like, they're really, like, super attuned to boundaries and balance, and like, more than we were. And I have to sit and examine that, because the story I'm about to tell is more in the vein of what I think, what I experienced with most of the successful people I know, which is, we've worked our asses off for a lot of our careers.

• 1:50:01Speaker 01

  And, uh, yeah, we've been successful, and some of that was luck. But someone told me, luck is when preparation meets opportunity. I really believe that. And I think, um, I was really driven. I was driven, even despite, you know, I had young kids. I was at a point in my Google career where I had an opportunity to be in a really, I was in the most senior role. Cheryl had left. I had taken part of her responsibilities. It ended up then being more after this period. I'd come back from maternity leave with my second child, and it was 2008, Lehman Brothers collapse is literally like the week I'm back from maternity leave. And I'd come back early because things were shaky. And in the end, that 08 sort

• 1:50:44Speaker 01

  of mini recession was not as impactful to tech. But at the time, it did not look like it was going to be an easy one. And in a very not well-known action, because I think the recent layoffs Google did, people, it's the first time Google's ever done layoffs. Actually, no, I laid people off in 2008, uh, in my division. And I came back from leave and made that call. And the day that I had to do, that the layoff announcements were happening, and I personally spoke to some of the infected employees, meaning, laid them off in a conference room with HR.

• 1:51:19Speaker 01

  I talked to my, my mom said, I really want you to come to New York. We're going to surprise your father for his birthday. And I was like, oh, I just don't think I like, I gotta do this. Like I'm under so much pressure as a leader. I've got to deliver this message. It's going to be brutal. And I talked to my manager who at the time, I mean, kudos to him. Could have said, yeah, no way you're going to New York. Like you gotta do this. And I sort of thought about, and I was like, you know what? I think if I did the Mountain View stuff for Google and took a red eye and went to, we had a team, I had a team in Boston, in Cambridge, actually. I could meet that team, which would actually be a good thing to do, do back to back geo visits. And then I could fly to New York and I could be there in time.

• 1:52:02Speaker 01

  And he said to me, he's like, if you think you can do that and the red eye isn't going to affect you enough. You know, I got to deliver messages in, in Cambridge. Then yeah, go for it. Like, so to his credit, and this is for all the managers out there. He was like, if you can make it work and align, because it's never, you can't always choose one or the other. You're balancing your professional obligations, your personal life. But yeah, I got there. I surprised my father. I, I saw him the next day too, which was really, ended up being really important. Because just a few weeks later, I got a call during the day in California from my mom. Uh, and my dad had died of a heart attack. On the way to the airport, I called my best friend. And I was like sobbing and I was like, what if I hadn't gone? What if I hadn't gone?

• 1:52:46Speaker 01

  And she was like, but you did, you did. But, but really it was me saying to myself, oh my God, I really high chance that I had not gone. Like, cause I was just in that mode professionally and my ambition and my sort of priorities, honestly.

• 1:53:03Speaker 01

  And I think that's the lesson that when I share that story, I think sticks with people. Because now for sure, you know, I'm a certain age, like I've had a certain amount of success. Of course I'm going to go to my parents' surprise birthday party. But then it was not so obvious. And so I guess I would just ask everybody, just, you can't be there for everything, but having an eye on what's really important. Earlier in your life than you're developmentally ready to end up being maybe the biggest lesson of all.

• 1:53:39Logan Bartlett?

  Yeah, well, I appreciate you sharing that. It's a it's a powerful story and I think it's a it's a good lesson. We spend a lot of time talking about operating tactics and philosophies around hiring and managing and all that stuff. But at the end of the day, we're all people with lives and family members and

• 1:53:57Speaker 01

  Turns out we're all humans.

• 1:53:59Logan Bartlett?

  There's important stuff outside of it. Well, Claire, thanks for doing this.

• 1:54:01Speaker 01

  Thank you. No, thanks, Logan. It was a great conversation.

• 1:54:04Logan Bartlett?

  Really appreciate it.