The Exchanges

Q Not at all, but I want to start with a little bit on you. It's rare that I have an athlete turned entrepreneur, but I want to start with your context. So how did you make the way from athlete to tech CEO and entrepreneur? How did you come up with the idea? Talk to me about that.

A Well, I think a lot of my background being an athlete and growing up loving sports and exercise led me to founding Whoop, which is the company that I've been building for the last 10 years. I was always into sports and exercise. I was playing squash while I was at Harvard, and I just generally felt like I didn't know what I was doing to my body. I was someone who used to overtrain. I think other athletes will go through periods of undertraining or misinterpreting fitness peaks or getting injured, and this would have been around 2010, which I think from a cultural standpoint was the peak of more is more. You know, can you work out twice a day? Can you work out three times a day? How can you put on more muscle? How can you run faster? And so I felt ultimately like There might be a hole in the market around understanding recovery, and at least from my personal experience, that was, I think, what was holding me back as an athlete. I was someone who's very hard driving, and go, go, go, and, you know, sleep didn't even really occur to me as an important thing for being a good athlete or being a good student, and so I got very interested in physiology, Harry. I read something like 500 medical papers while I was in school. I wrote a physiology paper around how to continuously measure the And that ultimately became the business plan for Whoop. I think I became an entrepreneur before I e…

AI assessment note: “wrote a physiology paper around how to continuously measure the And that ultimately became the business plan”

Q It totally is. Final one. I tweeted this the other day, but it seems like something's just changed in the perception of Whoop, the velocity of adoption of Whoop. I'm sure you've seen it in your numbers, but I just see Whoop everywhere. Like, what was that inflection point over the last seemingly year, or maybe nine months even, but something's changed. What do you think it was?

A Whoop is a good example of it takes, like, a really long time to be successful in what feels like overnight. You know, we just talked about challenges raising companies. Capital. We talked about being seven years into the business and it almost failing, and then, you know, three years later, you're this massive success. I think it was getting both the technology and the business model to a place of it being really scalable. The technology in, let's call it, 2017, we were selling Whoop as one-time hardware, so it was 500 dollars, which was, you know, pretty expensive. It would have priced Whoop as, like, a high-end Garmin watch or something in that district, and what we saw over the course of 12 months is that Consumers were continuing to wear it. So we didn't have the same drop-off rates that had plagued, say, Fitbit or Jawbone or some of these other earlier step counters. The problem was that we actually didn't have many people buying them. So, you know, we were asking ourselves, well, is there a better business model here? If people are really going to wear Whoop forever, could there be some kind of a subscription where it makes it, you know, much cheaper up front for someone to try Whoop? And then if they fall in love with the product, it could be better for both parties. This is also around the same time that Fitbit as a publicly traded company was trading at about one time…

AI assessment note: “I think it was getting both the technology and the business model to a place”

Q Not at all, but I want to start with a little bit on you. It's rare that I have an athlete turned entrepreneur, but I want to start with your context. So how did you make the way from athlete to tech CEO and entrepreneur? How did you come up with the idea? Talk to me about that.

A Well, I think a lot of my background being an athlete and growing up loving sports and exercise led me to founding Whoop, which is the company that I've been building for the last 10 years. I was always into sports and exercise. I was playing squash while I was at Harvard, and I just generally felt like I didn't know what I was doing to my body. I was someone who used to overtrain. I think other athletes will go through periods of undertraining or misinterpreting fitness peaks or getting injured, and this would have been around 2010, which I think from a cultural standpoint was the peak of more is more. You know, can you work out twice a day? Can you work out three times a day? How can you put on more muscle? How can you run faster? And so I felt ultimately like There might be a hole in the market around understanding recovery, and at least from my personal experience, that was, I think, what was holding me back as an athlete. I was someone who's very hard driving, and go, go, go, and, you know, sleep didn't even really occur to me as an important thing for being a good athlete or being a good student, and so I got very interested in physiology, Harry. I read something like 500 medical papers while I was in school. I wrote a physiology paper around how to continuously measure the And that ultimately became the business plan for Whoop. I think I became an entrepreneur before I e…

AI assessment note: “that ultimately became the business plan for Whoop.”

Q I want to mention something that you said before, which is like, realism is overrated. I love this. And so why do you think being realistic is overrated, Will?

A Well, realistically, 90% of startups fail. So the 10% that are successful just In their own right, you know, have achieved something that's unrealistic. And I think too often feedback loops that are given to founders are to be realistic as sort of a criticism of something ambitious that they want to do. There's certain things you have to be very realistic about, like your burn rate relative to the expectations that you've set for your existing investors would be a good example of something to be realistic about. But let's take, for example, how you want to launch your product. Let's say there's someone out there who you think is the perfect Who needs to be using your product for you to launch it successfully? If you go say, I want fill in the blank famous person, and someone says, well, be realistic. I don't know if they're going to want to use your, you know, small little company's thing. I don't know if that's necessarily a good feedback loop. You know, I think you do want to have that sort of ambition or enthusiasm that what you're building is special and that, you know, the world is your oyster. There were a number of times where I think if we look back on it, what we did was wildly unrealistic, but it ended up being key to our success. One perfect example of that, which we just talked about, is having these high-profile athletes wearing our product twenty-four-seven withou…

AI assessment note: “realistically, 90% of startups fail. So the 10% that are successful... have achieved something that's unrealistic.”

Q you prioritize and when you prioritize it. I think your question for me is that when you think about kind of disruptive powers, how do you think about just how many things you want to disrupt and reinvent the wheel on versus actually how much you can take off the shelf and borrow and learn from others? How did you think about that blend of completely reinvent versus bluntly borrow?

A It's a great question. We knew that we wanted to be disruptive from the standpoint of health monitoring. So other tools that could do health monitoring in 2010 or 2012 or 2015, we generally wanted to disrupt all of them. There was this other question, though, of how disrupted we wanted to be to the market. People often ask me, well, how'd you get to LeBron James? How'd you get to, you know, Michael Phelps? How'd you get to these sort of high profile people? And the key to getting these high profile people is often finding someone in their life who's more influential to them than other people realize, and for the most part is somewhat unknown. And in the case of Professional athletes that often turns out to be their personal trainer. Now, personal trainer was also someone that we actually wanted to empower. We didn't want to disrupt, right? So we could have built technology that said, this is going to replace your trainer and this is going to replace your coach. But we were pretty mindful of the fact that if we did that, it would make it very hard to get the technology into the market and to get the technology adopted because we actually needed coaches and trainers to want to use it and to view it as a tool, a complimentary tool rather than a threat. So that would be an example of something where you're intentionally not being disruptive.

AI assessment note: “So that would be an example of something where you're intentionally not being disruptive.”

Q What are the little things that you do to maximize that?

A Well, I try not to eat within three hours of bedtime. That can disrupt your quality of sleep. Generally, alcohol is bad, so if You can limit alcohol. That'll improve your quality of sleep. I wear blue light blocking glasses about an hour before bed because I'm someone who actually is kind of constantly on their phone and looking at a screen. That's a good get out of jail free card if you're like me because, you know, cell phones and the light are producing light that tells your brain to stay awake. Blue light blocking glasses block that. You know, I like to be in a bedroom that's really cold, really dark, high air quality. I try to be somewhat mindful right before Before, right before the act of falling asleep, because, you know, things you think about or conversations you have with your partner can really just be disruptive, yeah.

AI assessment note: “I try not to eat within three hours of bedtime.”

Q I want to mention something that you said before, which is like, realism is overrated. I love this. And so why do you think being realistic is overrated, Will?

A Well, realistically, 90% of startups fail. So the 10% that are successful just In their own right, you know, have achieved something that's unrealistic. And I think too often feedback loops that are given to founders are to be realistic as sort of a criticism of something ambitious that they want to do. There's certain things you have to be very realistic about, like your burn rate relative to the expectations that you've set for your existing investors would be a good example of something to be realistic about. But let's take, for example, how you want to launch your product. Let's say there's someone out there who you think is the perfect Who needs to be using your product for you to launch it successfully? If you go say, I want fill in the blank famous person, and someone says, well, be realistic. I don't know if they're going to want to use your, you know, small little company's thing. I don't know if that's necessarily a good feedback loop. You know, I think you do want to have that sort of ambition or enthusiasm that what you're building is special and that, you know, the world is your oyster. There were a number of times where I think if we look back on it, what we did was wildly unrealistic, but it ended up being key to our success. One perfect example of that, which we just talked about, is having these high-profile athletes wearing our product twenty-four-seven withou…

AI assessment note: “too often feedback loops that are given to founders are to be realistic”

Q we looked today at Whoop and the Four billion dollar valuation, and you know, all the success and joy that you've had, looks all up and to the right, but there's always a different story behind the scenes, and you said to me before, there's value in the struggle early on. What did you mean by this value in the struggle early on, and why do you believe this, Will?

A Well, I think there's a lot of different ways to answer that question. One, I think it's valuable for you, the individual, or you, the entrepreneur, to have to wrestle with your idea, and wrestle with various The challenges associated with how much capital you've raised, and what your burn rate is, and how many people you want to hire, and how fast you want to take over the world, and when your idea kind of runs into the resistance of actually those challenges, it can hit you pretty hard, and I think I've seen stories, and you probably have too, of founders where it almost feels like the first year or two is so easy and effortless, and they're raising these huge rounds, and the valuation of business is going up so fast, and then all of a sudden something happens, and to kind of a very dark situation, And it almost can be a fatal moment. Whereas these companies, I think, that go through a period of struggle, and Whoop certainly was that, where we struggled to build the product, we struggled to build the technology, we struggled to scale it into a business, we struggled to, you know, have it be a business model that could ultimately be a well-valued technology business. Those challenges, I think, helped us build a resilience as an organization. It helped the leaders of the company, especially the founding team, understand what it takes to be successful and be a Appreciative, fran…

AI assessment note: “Those challenges, I think, helped us build a resilience as an organization.”

Q You mentioned, and we mentioned kind of prioritization amongst the partnership and amongst the team. You said something that I loved in terms of a statement. You said choose chaos over drama, choose speed over control. I feel like there could be a good book in this statement, Will. But what did you mean by chaos over drama first? What's the difference between chaos and drama?

A Well, this is a little bit of a, a way to just think about things happening in your organization on sort of a sliding scale. Often there are moments in time within your company or within a startup in general where it just feels like there's a lot going on, and some of that could be challenging, very challenging. You've got different people running into your office asking what's going on in other departments, and why is this late, and how are we going to get this done, and I hear this isn't working well, or that customer relationship's not great, and I like to think about in any given moment is the sort of degree to which challenges are arising, is that, can that be best framed as Chaos, just sort of the general chaos of, hey, we're trying to move fast, we're trying to build disruptive technology, different departments are moving at different paces, and everything needs to come together at once, that form of chaos? Or is it drama in the sense that, you know, this leader is complaining about that department, and that department is upset that this other technology hasn't sped up and isn't done yet? And so, to think about it as interpersonal relationships being drama, and chaos to be Sort of thinking about it as the general delivery cadence and general chaos associated with an organization that's operating at a fast pace.

AI assessment note: “interpersonal relationships being drama, and chaos to be... general delivery cadence”

Q Can I ask, what do you think you've done to keep such a tight relationship with both of them?

A The first thing is, I found partners that are incredibly complimentary. That much overlap in the things that, that we're good at. I mean, John Capilupo is a brilliant computer scientist, and Mathematician. I think I had a reasonably good vision for the product and for the market and how we could get the right people to use it. Often, we had to be deferential to each other on the things that the other was oriented towards. I do think that helps so that you're not saying ever in the back of your head, well, I, I could have done that differently, or I could have done that better. You want to try to really avoid that kind of attitude as you're working through challenges, and I think it also, in turn, makes you more empathetic To the business that you're building. Now, of course, when you have very complimentary skills, it also makes it easier to say, well, shouldn't we just be building that faster? Or, you know, vice versa, shouldn't we be selling more of them? That's where the hugging and out part really comes in, Harry, and you have to find ways to constantly remind yourselves why you're on this journey together, and have, I think, you know, a lot of gratitude for the smart people that you work with every day.

AI assessment note: “I found partners that are incredibly complimentary.”

Q Can I ask, we spoke about kind of scaling the, the organ yourself. When you think about the work that you've done personally to become a better CEO, what have you done personally to be the best CEO that you can be? And I guess what's worked and what hasn't worked.

A The first thing that you have to figure out, and this was a real challenge for me, is that your individual performance and the company's performance are two separate things. And it could be that I was a very young person when I started Whoop, you know, 21, 22 years old. Whoop wasn't just the first company I, you know, I started. It was my first job. So I had a lot tied up in how the company was performing, and that's a pretty unhealthy mindset. You want to be able to disassociate your own individual performance and that of the company's performance. It used to be that if Whoop had a bad day, I thought I had a bad day, and if Whoop had a good day, I had a good day, and if Whoop was failing, I was failing. Right. In reality, you can be getting a little bit better every single day, independent from the company's performance. And you and I have both seen this, where you have companies that are doing enormously well, and you've got founders that are completely strung out, burned out, depressed. You can see it on the other side, where you've got companies that are totally struggling, and yet the founders remain upbeat, and they remain resilient, and they remain resourceful. And so there is this important thing to understand that those are sort of disassociated. Once you can create that disassociation in your mind, I think it helps you go on that Journey of how you can become a better…

AI assessment note: “I got into meditation. It was deeply helpful for me in building the company.”

Q we looked today at Whoop and the Four billion dollar valuation, and you know, all the success and joy that you've had, looks all up and to the right, but there's always a different story behind the scenes, and you said to me before, there's value in the struggle early on. What did you mean by this value in the struggle early on, and why do you believe this, Will?

A Well, I think there's a lot of different ways to answer that question. One, I think it's valuable for you, the individual, or you, the entrepreneur, to have to wrestle with your idea, and wrestle with various The challenges associated with how much capital you've raised, and what your burn rate is, and how many people you want to hire, and how fast you want to take over the world, and when your idea kind of runs into the resistance of actually those challenges, it can hit you pretty hard, and I think I've seen stories, and you probably have too, of founders where it almost feels like the first year or two is so easy and effortless, and they're raising these huge rounds, and the valuation of business is going up so fast, and then all of a sudden something happens, and to kind of a very dark situation, And it almost can be a fatal moment. Whereas these companies, I think, that go through a period of struggle, and Whoop certainly was that, where we struggled to build the product, we struggled to build the technology, we struggled to scale it into a business, we struggled to, you know, have it be a business model that could ultimately be a well-valued technology business. Those challenges, I think, helped us build a resilience as an organization. It helped the leaders of the company, especially the founding team, understand what it takes to be successful and be a Appreciative, fran…

AI assessment note: “Those challenges, I think, helped us build a resilience as an organization.”

Q when things are not going well, they often say like, should I give up? And I'm constantly stuck in this kind of quandary of, like, you know, should you be realistic when you don't have product market fit, or should you subscribe to the Silicon Valley idealism and say, no, a founder's vision is unwavering and you never give up? How do you balance between realism and then unwavering vision?

A I think a good question to ask yourself is the original vision that we set out on wrong, and the thing that I kept coming back to through all the challenges of building Whoop was that I believe the original vision was still right. There were challenges for For how we were going to be able to build the technology against it, there was going to be challenges for how we were going to sell against it, but that original vision that we could build technology to be worn 24 seven that would help first the best athletes in the world improve their performance, and then over time consumers improve their health, that to me seemed very true and very relevant. Through all the sort of painful stages of building the company, that's what I kept coming back to, and so that I think at least helped me personally Never quit. And I do think that maybe many startups fail because the founders quit too early or because they get in, you know, disagreements.

AI assessment note: “I think a good question to ask yourself is the original vision that we set out on wrong”

Q Can I ask, what do you think you've done to keep such a tight relationship with both of them?

A The first thing is, I found partners that are incredibly complimentary. That much overlap in the things that, that we're good at. I mean, John Capilupo is a brilliant computer scientist, and Mathematician. I think I had a reasonably good vision for the product and for the market and how we could get the right people to use it. Often, we had to be deferential to each other on the things that the other was oriented towards. I do think that helps so that you're not saying ever in the back of your head, well, I, I could have done that differently, or I could have done that better. You want to try to really avoid that kind of attitude as you're working through challenges, and I think it also, in turn, makes you more empathetic To the business that you're building. Now, of course, when you have very complimentary skills, it also makes it easier to say, well, shouldn't we just be building that faster? Or, you know, vice versa, shouldn't we be selling more of them? That's where the hugging and out part really comes in, Harry, and you have to find ways to constantly remind yourselves why you're on this journey together, and have, I think, you know, a lot of gratitude for the smart people that you work with every day.

AI assessment note: “we had to be deferential to each other on the things that the other was oriented towards.”

Q You mentioned, and we mentioned kind of prioritization amongst the partnership and amongst the team. You said something that I loved in terms of a statement. You said choose chaos over drama, choose speed over control. I feel like there could be a good book in this statement, Will. But what did you mean by chaos over drama first? What's the difference between chaos and drama?

A Well, this is a little bit of a, a way to just think about things happening in your organization on sort of a sliding scale. Often there are moments in time within your company or within a startup in general where it just feels like there's a lot going on, and some of that could be challenging, very challenging. You've got different people running into your office asking what's going on in other departments, and why is this late, and how are we going to get this done, and I hear this isn't working well, or that customer relationship's not great, and I like to think about in any given moment is the sort of degree to which challenges are arising, is that, can that be best framed as Chaos, just sort of the general chaos of, hey, we're trying to move fast, we're trying to build disruptive technology, different departments are moving at different paces, and everything needs to come together at once, that form of chaos? Or is it drama in the sense that, you know, this leader is complaining about that department, and that department is upset that this other technology hasn't sped up and isn't done yet? And so, to think about it as interpersonal relationships being drama, and chaos to be Sort of thinking about it as the general delivery cadence and general chaos associated with an organization that's operating at a fast pace.

AI assessment note: “interpersonal relationships being drama, and chaos to be Sort of thinking about it as the general delivery cadence”

Q Okay, so I've got a couple of questions to offshoot this. Say the drama goes into overdrive, and we've got to let someone go, well, I suck at firing people. I hate it. I'm too nice. I'm British. We just cannot do this. How do you fire people the right way?

A Well, I think the moment you lose trust in someone you're working directly with, it's important to have a conversation about why you've lost trust in them, and can they earn it back? I think generally speaking, if you've lost trust in someone who reports directly to you, or runs a, you know, Core facet of your organization. You're not doing them any favors by still having them in the organization either, because that's not going to be a great way for them to grow their careers either. So that's how I frame is, hey, we want to be creating the best environment for the company. We want to be creating the best environment for you to grow in your career. And the moment that trust is broken, that situation no longer exists. So it's a natural continuation.

AI assessment note: “So that's how I frame is, hey, we want to be creating the best environment”

Q when things are not going well, they often say like, should I give up? And I'm constantly stuck in this kind of quandary of, like, you know, should you be realistic when you don't have product market fit, or should you subscribe to the Silicon Valley idealism and say, no, a founder's vision is unwavering and you never give up? How do you balance between realism and then unwavering vision?

A I think a good question to ask yourself is the original vision that we set out on wrong, and the thing that I kept coming back to through all the challenges of building Whoop was that I believe the original vision was still right. There were challenges for For how we were going to be able to build the technology against it, there was going to be challenges for how we were going to sell against it, but that original vision that we could build technology to be worn 24 seven that would help first the best athletes in the world improve their performance, and then over time consumers improve their health, that to me seemed very true and very relevant. Through all the sort of painful stages of building the company, that's what I kept coming back to, and so that I think at least helped me personally Never quit. And I do think that maybe many startups fail because the founders quit too early or because they get in, you know, disagreements.

AI assessment note: “a good question to ask yourself is the original vision that we set out on wrong”

Q What's the biggest mistake people make when it comes to health and fitness?

A I think consistency. The more time I've spent around high performance people, let alone just general trends for health and fitness, the more I've come to really appreciate consistency. You know, high performance is exceptional output delivered consistently over time, and I think many folks who are, you know, sort of early to their journey of caring about health and fitness struggle with consistency. It's very hard to get fit in a week. In fact, it's impossible, but it's not that hard to do it in three months. You just have to be consistent. Right, and I think the same can be said of weight loss. I think the same can be said of sleep improvement. It's all about consistency.

AI assessment note: “struggle with consistency. It's very hard to get fit in a week.”

Q it's, you know, bluntly, and this was from Fagnum, but when we look at, like, funding journeys, one of the biggest, you know, roles of a manager slash CEO is actually funding the company and ensuring that you have runway. I want to hear, what was your most memorable fundraising Story first. And then second, how did you get Middle East money when you just had weeks of runway left?

A Well, look, you know, when you're building a capital intensive business like Whoop, there can be moments that are challenging to raise capital. I think that was definitely the story for us at various points in the company's evolution. We had this hairy moment where we were transitioning from being a hardware business to being a subscription. That ended up being the right decision for the business, but it also demonstrated that we were Seven years in and hadn't quite found our business model. So, you know, gone through tens of millions of venture dollars, and we were still trying to find the perfect business model. We'd found it, but now we needed to get more capital to be able to accelerate it, and there was one round of financing, certainly, where we ultimately had to raise capital from, at the time, what was one of our largest customers, and they were based in Dubai, and so there were these crazy trips to back and forth to Dubai to come in on the round and Fortunately, everyone's investment in Whoop is doing really well.

AI assessment note: “one of our largest customers, and they were based in Dubai”

Q I mean this respectfully. And we may have to take this one out, but I'm just too intrigued. Why do you think you're able to charge the subscription that you charge, which also, funny, is not cheap either, when alternative competitors, many others, do not? What do you think the difference is?

A Well, I think it's in the category of creating something new versus replacing something existing. So from a pricing and value standpoint, it tends to be a little bit more of a confusing story out of the gates, and I think in a few years it'll seem obvious why, but today, to your question, it's Probably something that people are wondering, you know, what is the daily value of a life coach, or the monthly value of a life coach, or the monthly value of having an alerting system to tell you to see a doctor? It's not like that doesn't really exist. Sure, there's been other products in the space, but have they actually delivered on that value proposition? What is the value of being able to change someone's behavior and improve their health? So that's how we think about it, and ultimately, we're on that journey with the member, with the customer. We feel it's our responsibility to be delivering value every day, every week, every month, every year. And if we don't, you can cancel. And by the way, you can sign up for Whoop today for 30 dollars, and we send you the hardware in the mail for free. So we're betting on our experience to prove to you that we're going to deliver that value.

AI assessment note: “creating something new versus replacing something existing”

Q you think about kind of the importance of pace, what are the things you have to go slow on to go fast? Like one that comes to mind for me would be hirings. Don't rush a hiring process. It's an irreversible decision, but fuck me if you get it wrong. It ain't friendly. How do you think about the things that you have to go slow on to go fast?

A Well, it's an interesting example you gave. You know, I think a lot of what makes hiring processes slow is you have these sort of periods of figuring out, well, what is it you're actually trying to hire? Who are all the stakeholders who need to be bought into that? What's the person's function going to be? Then you actually have the phase of going out and trying to find that person and hiring them. I think in the sort of upfront stage, you can be fairly deliberate, and maybe to your question, this would be the slow part of it, right, where you're ultimately, you know, focused on having everyone have alignment, but then you're in the mode of, okay, we know what we're looking for, let's go, and then you're moving as fast as you possibly can to find the right person. In general, I try to cut as much slack out of processes as possible. I think that as you grow and as you have more people in an organization, there's sort of this urge to focus Form more committees and form more meetings. And I think the more you can just cut away at that and get people comfortable with the fact that, hey, you're going to be making decisions. You do not need everyone's bind. You got to move fast. And when you say that, it just changes people's attitude in such a positive way. It's amazing.

AI assessment note: “in the sort of upfront stage, you can be fairly deliberate... this would be the slow part”

Q you prioritize and when you prioritize it. I think your question for me is that when you think about kind of disruptive powers, how do you think about just how many things you want to disrupt and reinvent the wheel on versus actually how much you can take off the shelf and borrow and learn from others? How did you think about that blend of completely reinvent versus bluntly borrow?

A It's a great question. We knew that we wanted to be disruptive from the standpoint of health monitoring. So other tools that could do health monitoring in 2010 or 2012 or 2015, we generally wanted to disrupt all of them. There was this other question, though, of how disrupted we wanted to be to the market. People often ask me, well, how'd you get to LeBron James? How'd you get to, you know, Michael Phelps? How'd you get to these sort of high profile people? And the key to getting these high profile people is often finding someone in their life who's more influential to them than other people realize, and for the most part is somewhat unknown. And in the case of Professional athletes that often turns out to be their personal trainer. Now, personal trainer was also someone that we actually wanted to empower. We didn't want to disrupt, right? So we could have built technology that said, this is going to replace your trainer and this is going to replace your coach. But we were pretty mindful of the fact that if we did that, it would make it very hard to get the technology into the market and to get the technology adopted because we actually needed coaches and trainers to want to use it and to view it as a tool, a complimentary tool rather than a threat. So that would be an example of something where you're intentionally not being disruptive.

AI assessment note: “that would be an example of something where you're intentionally not being disruptive.”

Q billion dollar company. When they were 50, you got in front of him. You sold the mission. You looked him in the eye. You made him join Whoop over Facebook or Google Health. Now, you're sitting in CNBC. You're sitting with, you know, whoever, big name investor. You're not sitting in that room hiring him. How do you retain that talent acquisition machine when you're no longer front and center?

A Well, I do think that's a goal that you should have for yourself as a founder as soon as possible. How quickly can I build a team to hire great people without me? How can I scale the mission or vision pitch as much as possible? I think there's things you can think about as a CEO or a founder about how you can scale yourself as a company goes from a hundred people to say, 600 people. You know, for example, I do a, a call with everyone on in their first week where it's, you know, a group of people and I do a Q and a, and I talk about the history of loop or answer whatever questions people might have about the company. I spent a lot of time writing our onboarding book. And spending a lot of time with our talent team about, okay, fill in the blank, you're a marketing exec, you just joined Whoop, or you're a software engineer, or you're a hardware engineer, like, what's the experience that you have in the first two weeks, or the first 30 days, for how you get to know this company, and you kind of figure out where you want to land. Again, if you're a company that wants to move fast, that's the kind of stuff you want to have really buttoned up, is like, onboarding. How quickly can you get someone bought into the org and moving fast?

AI assessment note: “How can I scale the mission or vision pitch as much as possible?”

Q I mean, even today, I don't like going on holiday because, like, it's such a part of me and who I am that when I leave it, I feel completely bereft and lost, actually, as a person. How do you untie your identity away from the company that mine's seven years, yours is 10 or 11? How do you do that when it is so ingrained in both of us?

A Well, identity and performance, I think, are a slightly different thing. You know, it's okay, I think, if your identity is, you know, closely related to To what you're building and your career and what you're passionate about. But I think it's important for you to recognize that your performance is not just that of the company's. That's what I was really speaking to. You know, another thing that can help, and this is more of a scale question, is just the degree to which you think of yourself as an individual contributor versus a manager. And if you're running a 10 person company, a lot of the company's output can actually be your individual contribution. So we've seen that when you're a smaller company, your individual contributions Are really important. At some point, it's probably close to 50 people, but definitely between 50 and a hundred people, the output of the organization becomes much more about the overall team than any singular, you know, effort you're making, or any singular contribution you're making, and I think that can be a painful transition for a founder if they're not kind of recognizing that it's happening, because often they'll find themselves trying to go deep on something or be the individual on something, when really they need to pull back and be delegating and be managing and Trying to help, you know, finesse the overall organization, and again, be focus…

AI assessment note: “Well, identity and performance, I think, are a slightly different thing.”

Q you think about kind of the importance of pace, what are the things you have to go slow on to go fast? Like one that comes to mind for me would be hirings. Don't rush a hiring process. It's an irreversible decision, but fuck me if you get it wrong. It ain't friendly. How do you think about the things that you have to go slow on to go fast?

A Well, it's an interesting example you gave. You know, I think a lot of what makes hiring processes slow is you have these sort of periods of figuring out, well, what is it you're actually trying to hire? Who are all the stakeholders who need to be bought into that? What's the person's function going to be? Then you actually have the phase of going out and trying to find that person and hiring them. I think in the sort of upfront stage, you can be fairly deliberate, and maybe to your question, this would be the slow part of it, right, where you're ultimately, you know, focused on having everyone have alignment, but then you're in the mode of, okay, we know what we're looking for, let's go, and then you're moving as fast as you possibly can to find the right person. In general, I try to cut as much slack out of processes as possible. I think that as you grow and as you have more people in an organization, there's sort of this urge to focus Form more committees and form more meetings. And I think the more you can just cut away at that and get people comfortable with the fact that, hey, you're going to be making decisions. You do not need everyone's bind. You got to move fast. And when you say that, it just changes people's attitude in such a positive way. It's amazing.

AI assessment note: “in the sort of upfront stage, you can be fairly deliberate, and maybe to your question”

Q know, whatever, 4.2 billion dollars. I don't know. Amazing number. But it's like, you're gonna get execs in from very seasoned, storied companies who have the incredible resume. They're not so used to the chaos. How do you think about when the right time is to bring in storied execs with that hailed resume who aren't used to the chaos and are used to a bit more of the stability?

A Well, this goes back to the other question you had, which is this sort of relationship between speed and control. And I think this varies a lot by company. For Whoop, we decided early on that moving quickly in the space was going to be a differentiator for us. One, we felt like technology businesses in the health space in general moved really slowly. And two, we felt the whole world of research and healthcare operated at a completely glacial pace. So we took it on ourselves to say, okay, when we build technology, and when we do research, we want to do it really fast. We want to be moving at an uncomfortable pace. It's one of our cultural values to actually move at an uncomfortable pace. We tell people that in the interview process, and we tell them that when they joined, and it helped self-select who's right for our organization and who's not, and I think being able to embrace this idea of moving at an uncomfortable pace is a little bit independent from how much experience you have in your career or where you're coming from. There's certainly seasoned executives who love it. There's certainly people straight out of college who love it, but it is sort of True to the whoop culture. Now, how does that also relate to control? You realize that the way to go fastest is to empower more and more people in your organization to be making decisions every day. So if you have a company cult…

AI assessment note: “this goes back to the other question you had, which is this sort of relationship”

Q know, whatever, 4.2 billion dollars. I don't know. Amazing number. But it's like, you're gonna get execs in from very seasoned, storied companies who have the incredible resume. They're not so used to the chaos. How do you think about when the right time is to bring in storied execs with that hailed resume who aren't used to the chaos and are used to a bit more of the stability?

A Well, this goes back to the other question you had, which is this sort of relationship between speed and control. And I think this varies a lot by company. For Whoop, we decided early on that moving quickly in the space was going to be a differentiator for us. One, we felt like technology businesses in the health space in general moved really slowly. And two, we felt the whole world of research and healthcare operated at a completely glacial pace. So we took it on ourselves to say, okay, when we build technology, and when we do research, we want to do it really fast. We want to be moving at an uncomfortable pace. It's one of our cultural values to actually move at an uncomfortable pace. We tell people that in the interview process, and we tell them that when they joined, and it helped self-select who's right for our organization and who's not, and I think being able to embrace this idea of moving at an uncomfortable pace is a little bit independent from how much experience you have in your career or where you're coming from. There's certainly seasoned executives who love it. There's certainly people straight out of college who love it, but it is sort of True to the whoop culture. Now, how does that also relate to control? You realize that the way to go fastest is to empower more and more people in your organization to be making decisions every day. So if you have a company cult…

AI assessment note: “moving at an uncomfortable pace is a little bit independent from how much experience you have”

Q When you have someone join the team, do you start from a position of total trust and it's yours to be lost? Or do you start from very little trust and it's yours to be earned in increments? How do you think about that starting position on trust?

A I tend to lean in on trust. You know, I like to hire people and believe that they're going to be successful. I think a slightly related question is how much responsibility do you give people right when they start? I think it's helpful to have people get some wins under their belt, and then be giving them more and more responsibility. I also think an advantage that, that startups have over big companies, we don't have to put you in a box. Like, I've always been better, I think, at hiring people than writing job descriptions. And so, you know, you really want to Find great people, and I think empower them to grow and grow and grow, and that could be in sort of unexpected ways, but it's an advantage that a startup leader has over, say, a big company is that they can embrace that, and it's part of the reason that I think startups can hire great talent.

AI assessment note: “I think a slightly related question is how much responsibility do you give people”