20VC: Checkout.com Founder Guillaume Pousaz on The Transition From Bootstrapped Founder to Raising $830M and a $15Bn Valuation, What It Means To Have "3 Roadmaps For Life" & How Becoming a Parent Changes the Type of Leader You Are

Guillaume Pousaz is the Founder and CEO of Checkout.com, one of the world's leading global payments solutions providers and one of Europe's most valuable private companies. Guillaume founded Checkout.com in 2012 and bootstrapped the business until its record-breaking $230M Series A led by Insight and DST in 2019. Since, Guillaume has raised a further $600M for Checkout from the likes of Coatue, Tiger, Blossom, GIC and Greenoaks. As part of this process, Guillaume has scaled the team to over 900 people around the world and Checkout as one of the category leaders in payments with a reported $15Bn valuation. In Today’s Episode with Guillaume Pousaz You Will Learn: 1.) How Guillaume made his way into the world of payments following a travelling experience? How that experience led to his founding the now $12Bn, Checkout.com? 2.) Why did Guillaume wait 7 years into the running of the business before raising a massive $230M Series A? Why was then the right time? Was it a difficult mental transition to move from lean, capital efficiency to raising $230M? Why have Checkout never spent a single dollar on marketing? Is it true, Checkout has never spent a single dollar you have raised? 3.) What does Guillaume mean when he says he "has 3 roadmaps for life"? How does he structure his planning for the next 2,5 and 10 years? How does Guillaume think on his own identity and how it is tied to Checkout, the company? How does Guillaume advise founders in terms of tying their identity to their company? 4.) Why does Guillaume believe that becoming a father made him a better CEO? How did it impact his operating style? How does Guillaume analogise the role of the CEO to the profession of being a sailor? How does Guillaume think through his relationship to money today? How has it changed over time? How does he think about ensuring it does not impact his children? 5.) In what way does Guillaume structure his decision-making process today? What does Guillaume believe it is about the velocity of decisions that determine the quality of the leader? What topics does Guillaume struggle to make fast decisions on? What advice does Guillaume give to founders in situations when you just do not know what to do? Item’s Mentioned In Today’s Episode with Guillaume Pousaz Guillaume’s Favourite Book: Dune by Frank Herbert As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

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

• 0:00Harry Stebbings?

  This is 20 VC with me, Harry Stebbings, and if you'd like to see the transcripts for 20 VC episodes, you can now go to 20vc.com and sign up for the newsletter. But to our show's day, and what I love so much about this guest is for seven years, he built this incredible business out of the spotlight, without Twitter profiles, out of tech crunch, and turned it into one of the defining businesses of the last decade. And so I'm thrilled to welcome Guillaume Pousaz, founder and CEO at Checkout.com, one of the world's leading global payment solutions providers and one of Europe's most valuable private companies. Guillaume founded Checkout.com in 2012 and bootstrapped the business until its record-breaking $230 million Series A, led by Insight and DST in 2019. Since then, Guillaume has raised a further

• 0:41Harry Stebbings?

  $600 million for Checkout from the likes of Co2, Tiger, Blossom, GIC, and Green Oaks, to name a few. As part of this process, Guillaume has scaled the team to over 900 people around the world and Checkout as one of the category leaders in payments with a reported $15 billion valuation on their last round. I'd also have to say a huge thank you to Carmen Alfonso Rico for the fantastic introduction today, and then also to Stephen at Insight for some brilliant question suggestions. I really do so appreciate that. But before we dive into the show's day, did you know that more than 80% of US public stock is owned by just 10% of Americans? This divide is even greater in the private markets. Carter makes it as easy to issue equity to your employees as it is to issue payroll, and for employees, as easy to accept it too. More than 16,000 companies issue

• 1:25Harry Stebbings?

  equity to their employees through Carter, whether you're just getting started or getting ready to go public, the team at Carter can help. Check them out at Carter.com. And finally, I've always been a big history fan, and so I want to talk about Cooley, the global law firm built around startups and venture capital. Since forming the very first venture fund in Silicon Valley, Cooley's formed more venture capital funds than any other law firm in the world. With 50-plus years working with VCs, they help VCs form and manage funds, make investments, and handle the myriad of issues that arise throughout a fund's lifetime. So to learn more about the number one most active law firm representing VC-backed companies going public, head over to Cooley.com and also check out Cooleygo.com. But that's enough from me. So now I'm very, very excited to hand over to Guillaume Pousaz, founder and CEO at Checkout.com.

• 2:16Speaker 01

  You have now arrived at your destination.

• 2:19Harry Stebbings?

  Guy, this is such a joy to do. I've heard so many great things from Carmen, from Ophelia, from Tom Stafford. So thank you so much for joining me today.

• 2:26Speaker 02

  Thank you. Thank you for having me.

• 2:27Harry Stebbings?

  Not at all. I've been looking forward to this one, but we see Checkout today and it's this incredible scale up company, one of the fastest in Europe. But I want to go back a little bit to the beginning. So tell me, what was that aha founding moment for you with Checkout?

• 2:39Speaker 02

  I think there's been a few themes that got me there. So I think there's not a single moment. One of the things I will say is that I started with computers at a very, very young age, probably 10 years before you were born. I still remember my Amiga 500. And then I remember basically just the computing power going and getting better. I mean, Windows 3.1, Windows 95, my first Pentium computer was like changing my life, pretty much. This is something that was always like an ingrained technology. It's going into one direction only, which is it's getting better and cheaper. If I fast forward now to 2005, when I kind of dropped out of college, I ended up in California and took a job in a payments company. And that payments company were basically helping US merchants sign internationally. And I think if you really have to nail down an aha moment, that's pretty much the aha

• 3:21Speaker 02

  moment is that it didn't take two and two for me to understand that commerce on the internet was going to be a big thing. This is 2006. So this is like pre iPhone, pre Facebook. But you know, faster internet, but cheaper bandwidth, you know, year on year, cheaper computing power, put this together, younger people like us, like me at the time, they said that commerce on the internet would actually only exponentially grow. And this is something we believe like, you know, 14 years ago now, and I still believe today, I still believe that we're at chapter zero and this is the beginning of the journey in the digital world. And I think there's a lot of numbers that back this. So I think that would be the right answer.

• 3:55Harry Stebbings?

  So I totally agree with you in terms of being at chapter zero. And I think what's really striking when you hear that is like, you know, actually Checkout being the 11 year journey that it is today. And so I guess my question to you is essentially, in a world where fundraising is so front and center for everyone starting, you didn't raise your Series A until 2019, and the company was, you know, so far further along than a Series A in terms of labeling. Why did you not do the traditional today and raise money earlier?

• 4:22Speaker 02

  So first of all, B2B payment processing, which is What we do focusing on enterprise is pretty capital efficient. I think also that, you know, five good engineers are better than a hundred average ones. And there's two different ways to kind of build a company. Either you try to hire a lot of people because you want to grow super quickly. For me, it was really like a life journey. I knew I would be doing this for a very long time. I knew that the time was infinite and I was just like super committed to do the things right. And really build the infrastructures before we try to scale. I think like this is something that was like, you know, ingrained in my mind. And if I look in the European market right now, you've got a company like Moni. Same thing, he built a business without taking capital for quite some time and just build it step by step. The other thing also is that the capital came in after we won what was still probably our biggest contract.

• 5:06Speaker 02

  Which is, you know, the largest video streaming company in the world, one that everyone is actually using. So I think that when we actually won this, we then realized that we were like changing gears. And this is the moment where at that point in time, I have two hundred seventy five employees, two hundred eighty. And I was never the CEO of such a big company. You know, we're going to go global, there's real potential there. And this is where I was like, I think it's the time to take the external capital, just taking a step back. We built a payment gateway first, then we built an acquiring bank, then we built a payment processor. That was the first six years of the journey. Then we started selling, then we won that big company. And I was like, we've done so much on our own. Now it's time to really thinking of like, how can we do more? And when I went on the fundraising for the series A on the back of like winning that deal.

• 5:51Speaker 02

  I was like, hey, what is my equation of value? It actually, it's a fun fact. We had never spent a single dollar in marketing before the series A, just like none. It was pure word of mouth, product led company. There's like four salespeople, there was no commercial organization. This is actually, when you think about it, pretty funny. But the equation of value for us in terms of fundraising is that we wanted somebody who had built sales teams, who had built marketing teams, who had scaled businesses. And that was like Insight. You know, when we met Insight, we're like, these guys, I think they have sixty five IPOs. All they do is scaling B two B SaaS softwares. They do that pretty well. I met Devon, I was like, okay, deal, I want to work with this guy. That was a given. And then in the round came DST. And DST was basically, you know, like Tom is a super thoughtful guy. He gave us like, I think.

• 6:34Speaker 02

  The international breadth, understanding how the Silicon Valley works. Then you have access to Yuri. Yuri is like one of the best investors in the world and one of the most well-connected guys. So that kind of opened the doors in the Silicon Valley. Then there was like Ribbit Capital, that was like just the knowledge of fintech. Make you like he gets it better than anyone else. And then there was G I C and G I C was really the access to Asia. Putting these four things together, we had an equation that kind of made sense for us. We had built a lot of the business, but we knew that the time was infinite. So we were like, hey, time to make a deal. And that deal came together and I think it completely transformed the company because it gave us new perspective that I didn't have as a CEO on my own.

• 7:13Harry Stebbings?

  Can I ask, was it a difficult mindset transition to make going from very capital efficient scaling, which you did for many years? It would have been nine years at that point to suddenly getting two hundred and fifty million dollars. And you have to switch your mindset from very lean but capital efficient growth to, hey, let's really pour fuel on the fire and spend.

• 7:33Speaker 02

  I mean, we have lightened the fires because the company is growing at a hundred percent, but we have never spent a single dollar of the money that we have raised. So I mean, all the money is sitting on the balance sheet. We kept the same discipline and I remember speaking to the vision fund and there was like, how are you going to spend all our money? We're like, we're not going to spend it. We've built a business with discipline for like nine years. And I think like that's who we are. And I mean, if you're, you should invest in who we are in our vision. It was like, we invest for people to deploy capital. And I was like, at that point in time, it was like, what I need from my investor is obviously balance sheet stability. Because for one big Silicon Valley company taking in that on their financial partner, there's nine others that tell you like, hey, they're not big enough for us, come back later. And the second thing is we were looking for mentoring.

• 8:11Speaker 02

  And I think like the fuel on fire for us as a B two B company where we were at the time, it wasn't necessary. We didn't raise for that. We really raised for like the accountability of having people on the cap table that push you to be the best version of yourself. And the other thing is like, we're not a B two C company. I mean, it's very different in spirit. And for me as a CEO, everything is a long-term decision. I basically had like three roadmaps, a two-year roadmap, a five-year roadmap and a 10-year roadmap. The two-year roadmap is more or less decided already now. So it's basically a zigzagging against this. I'm not involved and I made my decision on the five year roadmap and that most of these decisions are like strategic decisions. And sometimes they require capital, but again, we've built a business with like a capital efficient view.

• 8:55Speaker 02

  So like the all the the money we've raised in series B and series C, same logic. We took Tiger, you know, for like helping us grow as a company in terms of like the ability to understand public markets. Like really a private to public investor. We took a go to and we're discussing this because Chris is an extraordinary investor. So I think it's always this logic of like, you want to build a team, you want to extend your bench, but you don't do it purely for like, let's put the money to use. For us, I mean, we process like now a few billion every week. We get to the point where like our balance sheet is very important and that's why we raise money.

• 9:28Harry Stebbings?

  I love that in terms of never having spent a dollar that you've raised and it's always the best thing for an investor to hear. I do want to ask you, because you mentioned some of our mutual friends there, Chris especially. And I was speaking to a lot of our friends before and I said, there's some real questions that I really want to dive in with Guy. But I'm not sure if they're too personal. They said, no, fuck it. You can ask them. You should ask them. And so I wanted to ask you, you know, 11 years journey now building Checkout. And the thing I always struggle with is like, I am my company. And so when my company or I am removed, I feel this like void or loss. Do you know what I mean? So it's like going on holiday is horrible for me because you're not with your company and so it's very awkward. How do you think about tying your identity to Checkout and to your company?

• 10:05Speaker 02

  I think it's a complicated question. Obviously Checkout is a huge part of my identity and I think it will always be. But at the same time, you know, now Checkout is basically building its own identity. I mean, there is a management team, it's being shaped by the leaders we have on the C level, the 1200 actually employees we have in the company. The other 500 we're going to hire this year. And I think identity is something that is organic. So there's the CEO founder identity, there's the company identity. These two in the very beginning are very kind of the same thing. And then they start kind of building their own path. And what's important is that these two paths kind of complement each other, that there is a bit of a coherence between the two. And I think like, you know, they can completely complement each other. You don't need to try to like, how do I escape this? I think for me it's more a question like you need to be happy with what you build.

• 10:49Speaker 02

  You need to be proud of what you build as a founder, but also as the people that work there in your company, they need to be proud of the company. What company do you work for?

• 10:55Harry Stebbings?

  There was another element that you said earlier. You didn't know that you could do that sort of leadership in terms of kind of scaling with the company. And I want to ask, in terms of like self doubt, I was speaking to a unicorn founder last night. And he was saying they're at about a billion and they're obviously kind of moving towards fifteen to twenty over time. And he was like, I don't know if I can run a fifteen to twenty billion dollar company. I'm just scared shitless. When you think about self doubt in scaling your leadership, how do you deal with that self doubt? Given the speed, as he said, of checkout a hundred percent year on year.

• 11:25Speaker 02

  The main reason we took the investors was for like mentorship. And we've always taken a super humbling approach to how we run the business. I was never the CEO of a hundred people company, three hundred or one thousand. So first of all, don't be an entrepreneur if you don't want to deal with hardship. Because I think like that's part of the job and you're gonna have to live with it. But fundamentally, I have a good group of mentors that really like look after me. That are people that don't have any vested equity or equity in the company. And then have the investors. And I think also I have, I mean, I have to give it to her. I have my wife who's always there, you know, kind of help me. She's almost like the co-founder, the spiritual co-founder. We've been together since we're like fifteen, more or less. So I mean, we've shared more of a life together than not together. She gave me three beautiful kids. And I like this analogy is that a CEO is a bit like a sailor.

• 12:09Speaker 02

  You know, you leave the harbor, you do things during the whole day and then you come back home at night and you go to the harbor. If your harbor is safe, you got a lot of peace and it's resourcing. And I think like this is something that has always worked quite well for me. So I think like if you combine these things, you know, like the right mentors, the right investors, the right family setup or the right set of friends if you're not married. I think that helps a lot in kind of, you know, dealing with the hardship that you have as an entrepreneur. The other thing eventually that I would say, you need to be ready to keep learning all the time. It's like I read thirty to forty books a year. I travel, I meet people, I have access to incredible like, you know, entrepreneurs and tech leaders that actually process on checkout. We like to solve these problems and the brain is a bit like a muscle, you know, you need to keep training it. And the reality is that that's what allows you to sail through all the life of an entrepreneur.

• 12:53Harry Stebbings?

  Can I ask, you mentioned that your wife and your family, kids obviously changes so much of one's life. How did having kids change how you think about operating?

• 13:01Speaker 02

  So I had my daughter when I was twenty six and that happened at one in my life where, you know, like she really came as a rebirth for us. Because we had lost her dad and it was something that was kind of really important. She brought me a lot of stability, she brought me a lot of, you know, personal discipline, because now you're responsible for another human being. At checkout, I'm basically responsible for twelve hundred people. And the reality is that you learn from one another. I always said, like, you know, being a good dad also makes you being a good CEO. You can be super thorough and you can be super nice. And the reality is that the kids, they bring me that stability that allows me to go and deal with what I'm dealing with every day. And I learn from one another. And, you know, fun fact is, you always, I have so many friends now who are kind of my age. And they're still debating what is the right time to have kids. And I always joke with them, I say, there's no right time to have kids.

• 13:46Speaker 02

  You can look at that decision under any angle that you want. You can always find a counter argument to not have kids, like not the right time next year or whatever. I think like the answer to this is just have kids now and deal with it. It's the best experience of life.

• 13:58Harry Stebbings?

  I always have in my head, like, you know what, I really need to focus on work. I need to get the funds up and running. I need it to be a five X, a ten X, or whatever we go for. And I'll have kids when I'm thirty three, ten years out. Let's do that. That's a good plan. How do you advise me? My therapist tells me it's a completely shit plan.

• 14:15Speaker 02

  First of all, to have kids, you need to find a good wife. I think like that's the first one, you know, I would put out there. But if you have the good wife, I would say like this is not something you engineer. When you feel it inside of you, this is a gut feel decision. When is the right time is the right time. And if you try to think about it, I'm not saying you're in the wrong, we're all different. But I wanted to have kids when I'm thirty two, I ended up being a father when I was twenty six. So I think, you know, some of our thinking was similar when we were trying to plan. And being a father at twenty six made me a better human being and probably immensely contributed to who I am today and where checkout is today. So I'd say have the kids straight away.

• 14:46Harry Stebbings?

  I do want to also, you know, in terms of like that in itself, I often think about bluntly relationships to money, especially also kind of with incoming children, even if they're a decade out. But I think my big question is like, when we think about that, how do you think about your relationship to money and how do you evaluate that?

• 15:03Speaker 02

  I think that ultimately relationship to money will change over time with everyone. One thing I'll say is that checkout.com was never started to make money. As a matter of fact, I think it's fair to say that we never thought it would be as big as it is today. And now we still believe that we're at chapter zero because we really believe we're scratching the surface of what's possible. As an individual, you change your relationship to money for sure over the years, especially if you have access to it in a certain way. But now we go back to the kids. I have three kids and for me, it's a lot more important that my kids know me for being a good human being than for being a capitalistic hero. So I think like, you know, the kids force you and discipline as well. You want your kids to work, you want your people to have side jobs and everything. We fly an economy with the whole family. It's always like, it's really important. That's the way it should happen.

• 15:45Speaker 02

  So for now, I'm trying and I think funnily enough, my investors quite often tell me that, hey, you should leverage a little bit more what you have. But I tend to be pretty defensive and very swift on this is that this is something I say to my friends and actually even to the colleagues here at checkout. There's two types of hungry people in the world. There's the people that eat too much and the people that don't have anything in their stomach. We prefer belonging to the people that have nothing into their stomach because it lets you accomplish a lot more. And I think like the hunger is one thing that you need as an entrepreneur. And if you spoil yourself too much, you'll not be hungry anymore. So I think it's you need to find the right balance, but this is something that has worked well for us to date. I'm thirty nine, I'm able to go surfing when I want to go surfing, I'm able to go skiing when I'm going skiing, I have a roof for my kids, I don't need a lot more to be happy.

• 16:29Harry Stebbings?

  I totally get you. Can I ask, sorry, this is turning into like an open therapy session for me, but you should just bill me and then we can do like an invoice session. I was in this therapy session yesterday and they were like, you've got to bank self-esteem. And what they meant by that is like, when you have great moments, signing great contracts, hiring great people, bank it and remember it. Because in the hard times, you need to use that kind of wealth of good times to fight it. Do you stop and appreciate the good wins that you have rather than just always going for more and more and how do you? Do you think about that, like appreciation in the moment?

• 16:59Speaker 02

  So first of all, we are super grateful for what we have. And that's something, you know, like every day I look at the company, I look at my kids, I look at my wife. We're a happy family and achieved a lot with work. And certainly you have to contemplate what you have and be grateful for that. So that's a given. But then, at the same time, I think all best entrepreneurs and, you know, all people who've built category-defining company have that hunger inside of them where you just wanna do more, you wanna build more. At checkout, we wanna add more geographies, we wanna add more products, we wanna win more merchants. It's this whole thing of like, do I stop and pause and look at what we have achieved? And yes, absolutely, I do that. Is that enough for me? No, not at all, because I wanna build really a company that is long-lasting, that transcends generations.

• 17:43Speaker 02

  And we have a TAM, a total addressable market that is huge. Where if you take the three leaders today, which are adding Stripe and Checkout, we're literally scratching the surface of what's possible. This is mathematical. All the revenue is still sitting in the incumbents, so why would we rest now? Now that we have amazing products and amazing customers that are really happy with us and I have amazing investors that are helping us go after the opportunity. So that hunger and that willingness and resilience are key things. And I don't know what your shrink told you, but I would say, no, contemplate stuff, but don't stop there.

• 18:14Harry Stebbings?

  I do wanna ask, you know, when you think about going after the TAM, competing in the market that you're in, I always think like, essentially the core feature of great leadership is efficient decision-making. How do you think about your own decision-making today? Do you have frameworks? How has that kind of decision-making process changed for you?

• 18:28Speaker 02

  I don't have a framework. I make a lot of gut feel decisions and instinctive decisions. And by that, what I mean is that, of course, as a CEO now, I mean, I have a CEO office, I have a great leadership team and I do have access to data, but I don't think that data is the answer to everything. The life of a CEO is a bit like a probability tree. You arrive at a fork, you have to choose between A, B, C and D, and you have to make a decision. If you make a lot of good decisions, you move on the tree. If you make a bad decision, it sets you back. I think what matters is the amount of good decisions that you're making on that tree and how quickly you do them. So I see a lot of people quite often, you know, try to overthink a decision. Hey, I have sixty percent. Of the data that allows me to make a perfect decision, I'm gonna go and try to grab another twenty percent.

• 19:10Speaker 02

  I'm not like that. I'd rather do a lot of quick decisions. I get, you know, obviously data being pushed to me and I consume that data. But then I'd rather make the decisions quickly, move. I have no issue making mistakes. I've apologized to my entire company for making a mistake sometime. And the reality, mistakes are a good thing. They're just an additional piece of information that helps you be a better CEO. And fundamentally, what matters when you make a mistake is to learn from it and that's it. But it's the ratio of good decision and the average weighted time that you take them that is actually the key.

• 19:40Harry Stebbings?

  When you look back at the decisions that you make and have made, are there a consistent theme of segmented types which take longer for you? I agree with you in terms of speed of decision, but like for me in particular, when it comes to hiring, I'm great at fast decision making elsewhere. But there I'm like, shit, I really struggle to come to fast decisions. Are there areas where it takes you longer?

• 20:00Speaker 02

  I think like so on the hiring front, we just hired Oy from Toyota. He was best man, entrepreneur in residence. But we did a lot of like interviews, then I met Oy and I knew he was the guy. And you know, that was a nine months process. We met all these amazing CTOs from all around the world. And then I'm having a coffee with Oy in San Francisco, not for the CTO role, just to meet the guy. And I was like, this guy has our DNA. He loves to solve complex problems. I want to work with him. And I was like, not nearly an instant decision. Of course, he's gonna go through an interview process and everything, but I knew that he was the guy. It's just like, it's the light bulb moment. And I think like, talent is really, of course you want people who have experience and everything, but talent is not the only thing. The cultural fit, believing the same things than this person and just having that right match is actually what makes you win in the end.

• 20:44Speaker 02

  And I think like, you know, building a team is obviously super critical to any entrepreneur. And for me, I would go back to what I told you before is that I would not over engineer it. You meet a lot of people because that's the rule of big numbers. Of course, you try to qualify them, but when you have really a good fit with somebody, then you go all in.

• 20:59Harry Stebbings?

  So I totally with you in terms of the importance of that cultural fit. The trouble is honestly, in labour markets today, which are fast and so fluid, how do you think about stress testing that cultural fit in an interview process and more compressed timeframes?

• 21:12Speaker 02

  This is why you have a series of interviews that follow your first meeting is that we are a value driven company. So you have certain companies are mission driven. That's not us. We're a value driven company. We believe in our values. We believe in our operating principles. We have certain things that really drive our decision making. It's like really important to us. And what we do is that if we have kind of the match with somebody, then we send him through a process which is pretty data driven, with scorecards and everything, and then fundamentally there, if pretty much everyone agrees that he's one of us, then it's like we go with the heart. Like we're all in. We want that person to join and we figure out a way to make it happen. But the reality is that I'm not the sole decision maker ever, especially for like, you know, a role like the CTO where, I mean, two thirds of the company is product and engineering today. So I think it's, you know, there's a lot, I mean, I contribute with a lot of people, but

• 21:57Speaker 02

  the reality is that I ignite the fire if you want to, and then there's a lot of people are going to make sure that this is the right person. And if it is, then we go for it. But I think like a united management team is probably what's most important because everything starts from the top and then it's being pushed down. So if your management team is strong and has the same vision and share the same vision, and goes to the N minus ones and it aligns everyone and then the N minus ones goes to the N minus two and like fundamentally the bigger the company is and the more important this is.

• 22:23Harry Stebbings?

  Can I ask, how do you think about creating dissent in the management team? And what I mean by that is like creating debate. You don't want everyone to just say, yes, we agree with you or more, yes, we agree. How do you think about creating debate and discussion amongst the management team to really drive effectiveness?

• 22:40Speaker 02

  It's not one of our operating principles, but it's something that everyone knows at checkout is the obligation to dissent. Is that if you don't agree with something, you should raise your hand and say it straight away. We love debates. We have our whiteboarding rooms, which are like three sixty, like whiteboards where you can really like spend a lot of time whiteboarding and like debating on topics if you want to. But the reality is that it's ingrained in our culture that anyone can raise his hand and say something. As a CEO, I spend a lot of time on a one to one to just collect feedback. We have direct feedback. We have the feedback that comes through Picon that is completely anonymous. It's something that is really important to us because a culture is something that is also very organic. And you want people to believe that they can contribute to it. They should contribute to it. It's actually really important.

• 23:20Speaker 02

  You know, it's a sum of the parts. And I think like if you really have a kind of transparent structure and you actually action the feedback of people, then it kind of works. It shapes itself for something that is good.

• 23:29Harry Stebbings?

  Can I ask, you know, when you look at the company scaling, it scaled so fast with such increase in headcounts. What have been the most challenging elements in the company scaling for you as the leader? And I guess at what points did signs start to break?

• 23:41Speaker 02

  So I mean, we're in a very strange time. I mean, when COVID hit, there was five hundred fifty of us and now there's nearly twelve hundred. So we onboarded six hundred fifty people completely remotely on Zoom. Fundamentally, you know, I'm kind of like, I'm a student of the situation there and I'm learning along the way. One thing we did do is that we've opened all these channels of communication. And at all our all hands meetings, we have a list of things that people tell us they want to change or they want to see change. And fundamentally, we knock them one after the other, just like, hey, we want a better scheme to buy chairs and like laptops at home. Okay, we're going to build something like this. We want to look after mental wellness or after well being and like. I think like, as a CEO, my job is to obviously drive the business forward. But the people of the company are the catalyst of that company. And I think like, one thing is the company is only as good as the people.

• 24:26Speaker 02

  So you need to really make sure that as many people as possible are happy. I think this equation is very simple and the more happy people you have and the more good outcomes you get. And I think, you know, quite often, if you try to run a company with business plans and financial models and everything, you kind of deviate from that. That's why we are a value driven company, a mission driven company. And and I'm not, you know, like here, like writing cliches, but it's like, it's all after the mission. We need to deliver the mission. A value driven company is about the people and we believe in our values and we believe in people like, you know, like. We want people to believe in those values because they are what made us who we are today. And it's all about the people, hundred percent.

• 25:01Harry Stebbings?

  I'm totally with you in terms of being all about the people. I you mentioned there about kind of having the list and going down it one by one. And it kind of takes me back to something that both Chris and Carmen actually said beforehand, which is just how efficient you are with your use of time. You mentioned also kind of surfing earlier. How do you run your time and drive effectiveness with the time that you have? Given that you do so much and as your investors said, you're so productive with your time.

• 25:24Speaker 02

  So first of all, I have an amazing team. Let's put it this way. The second thing is I have zero issue delegating. So for me, it's like the less decisions I see, the better. I'm very much more like empower people to make decisions and you come to me if you really, really, really need me. The truth is, the bigger the company. The more geographies, there's an exponential amount of decisions. So you ultimately, you're gonna still see a lot of decisions. But in spirit, it's all about pushing the decisions down to other people. I would combine that with the fact that I love my job and I really do work a lot. So I certainly do more than eight hours a day. And now, yes, I mean with Jess, with my chief of staff, we started really like implementing certain processes. So if you want like, you know, factual tips, I have three types of meeting. I have the fifteen minute meeting, the thirty minutes meeting and the forty five minutes meeting.

• 26:06Speaker 02

  You have to choose between these three and I always keep fifteen minutes and each hour to do emails and WhatsApp. I'm a very big WhatsApp guy and WhatsApp is always on fire. What I do at the end of the week, every single week with the team that actually helps me manage my time is that we raise the meetings. Was that a good meeting? Yes or no? Was that a meeting where I needed to be there? If I didn't need to be there, then we kill the meeting, push the decision down, somebody else could do it. And I think like this is, then we iterate and progress this like constantly to just to try to make the best use of the time. I wish I could follow the inbox zero, but it's absolutely impossible when you get six hundred emails a day. So that's like an urban legend for me, or actually it's a dream that I'll probably never achieve. But I have three labels only in Gmail. I have urgent, end of the day, end of the week.

• 26:50Speaker 02

  Just these three labels and the assistants, they file the emails. And urgent is what I do every single fifteen minutes and every hour. End of the day is what I do when I finish my meetings and end of the week is what I do on the weekends. And this little formula has worked quite well for me and it allows me to be quite smart with my time.

• 27:06Harry Stebbings?

  Can I ask, how the hell do you manage WhatsApp? Because WhatsApp's become my new email and I actually just can't get my hands around it. Like you said, with six hundred emails, similar for me. But WhatsApp is the same and people write ten messages instead of one. And I'm just so behind on WhatsApp. How do you manage it?

• 27:21Speaker 02

  I am behind on WhatsApp as well. I was giving you my tips for like Gmail. I don't have the tips for WhatsApp yet and especially that this is personal. So you're not gonna give it for somebody else to manage. So the reality is that, and this by the way is very important, I write all my emails. But I have somebody who like and labels them for me and sorts them for me. WhatsApp is personal. I have my wife sending me pictures of my kids and things like this. So that's not something that, you know, I'm gonna give to an assistant. But WhatsApp right now is mostly on fire all the time. By the time you and I are finished speaking, there's probably like a hundred messages. Yes, this is still a struggle.

• 27:50Harry Stebbings?

  There's no, I totally agree. And also, I always think the person who creates like C C assistant in WhatsApp will be my hero. If you could bring in an assistant to a thread, amazing. But yeah, I'm gonna have to dive into a quick fire there with you now, G. So I say a short statement and then you give me your immediate thoughts. Does that sound okay?

• 28:06Speaker 02

  No problem, let's go.

• 28:07Harry Stebbings?

  Okay, so you said about kind of reading thirty to forty books a year. What's the favourite book and why?

• 28:12Speaker 02

  That's a tough question because ultimately you read so many of them. And actually, I listen to a lot of books as well. Audible is actually, uh, is hugely important to me. If you ask me favourite book, I'd go back to the childhood and I'd say Dune from Frank Herbert, because ultimately it's an amazing book. It's one of the best sci fi books ever. And if anything, I'm forcing my daughter to read it right now if she wants to see the movie. So I think like this one is probably top of mind for me.

• 28:32Harry Stebbings?

  What's the hardest element of your role with checkout today?

• 28:35Speaker 02

  Balance everything. You have constant people coming to you for questions and things and like being able to say no. And just finding the right balance is definitely the hardest thing right now.

• 28:45Harry Stebbings?

  What's the right way to view competition?

• 28:47Speaker 02

  I think competition is very good. Keeps you on the tip of your toes. And MySpace particularly, we have a very big tab. And it's exciting to see other people doing a good job because it's gonna force us to be the better version of ourselves.

• 28:58Harry Stebbings?

  What three traits would you most want your children to adopt?

• 29:01Speaker 02

  Humility, for sure, because I think like this is in our DNA at checkout and for me as a human being. Passion, because I want my kids to have the same passion that I have. And I think like if you don't have passion in life, life is probably a bit less exciting. And then I think kindness, because it's about helping others. And irrespective of where you are in life, you should always think about the others.

• 29:20Harry Stebbings?

  What leader do you most look up to and respect and why do you think that is?

• 29:23Speaker 02

  Probably tisha answer, but I would say Bill Gates. And the reason I'd say Bill Gates is, you know, he built one company only. And it pretty much of a meteoric rise. And I was mentioning, you know, how Pentium changed my life when I was fourteen years old. I'm always amazed with him. And by the way, other amazing book, Hard Drive, about his life, great book. I'm amazed how at fifty-three, when he's on top of the world with Microsoft, he says, hey, I'm gonna quit and I'm gonna work in my foundation. The Bill and Melinda Gates Foundation. And he takes all the learnings that he had from business and tries to make the world a better place. Really like take problems, solve problems and move from a completely capitalistic view to like a good impact. So I think like for that, you would be up there.

• 30:02Harry Stebbings?

  What's the biggest lesson in terms of what it takes to acquire the best talent?

• 30:06Speaker 02

  Just be genuine. If you're not genuine and authentic, people see through you. They always do. And if they don't, it will fail later.

• 30:12Harry Stebbings?

  Final one, what's the next five years for you and for Checkout? Just how big could this be in the next five years?

• 30:18Speaker 02

  I think nothing compounds like payments, so it's kind of hard to say. But I think it's going to be more growth, more people, more merchants, more products, more geographies. One thing I will say is that payment companies, or at least a company like Checkout, is reinventing how businesses, especially digitally native businesses, are interacting with financial services. So I always say to my team, we're still at chapter zero, and I really believe that. I believe that we can sell a lot more products to merchants, and I believe that we can actually really create value in how, you know, the economy, you know, economic recovery, these type of things. It's very topical right now, but the wrong can leave a review here in the UK. We have a role to play in the future, and we're very excited about that.

• 30:56Harry Stebbings?

  Listen, this has been so much fun, Stukey. As I said, I heard so many great things from Devon, Chris, Colin, so thank you so much, and I really appreciate it.

• 31:03Speaker 02

  Thank you very much, Harry.

• 31:06Harry Stebbings?

  Again, I want to say huge thank you to Keel. You heard the immense stresses on his time there, but what an incredible journey with Checkout, and what an exciting time ahead. If you'd like to see more from us behind the scenes, you can, of course, on twenty B C dot com. I always love to see you there. But before we leave you today, did you know that more than eighty percent of US public stock is owned by just ten percent of Americans? This divide is even greater in the private markets. Carter makes it as easy to issue equity to your employees as it is to issue payroll, and for employees, as easy to accept it too. More than sixteen thousand companies issue equity to their employees through Carter. Whether you're just getting started or getting ready to go public, the team at Carter can help. Check them out at Carter dot com. And finally, I've always been a big history fan, and so I want to talk about Cooley, the global law firm built around startups and venture capital.

• 31:52Harry Stebbings?

  Since forming the very first venture fund in Silicon Valley, Cooley's formed more venture capital funds than any other law firm in the world, with fifty-plus years working with VCs. They help VCs form and manage funds, make investments, and handle the myriad of issues that arise throughout a fund's lifetime. So to learn more about the number one most active law firm representing VC-backed companies going public, head over to Cooley dot com, and also check out Cooleygo dot com. As always, I so appreciate all your support, and I can't wait to bring you two phenomenal episodes next week.