20VC: Whoop Founder, Will Ahmed on How CEOs Can Perform at their Highest Level, Why There is Value in Struggle Early On, Why Realism is Overrated in Startups and How To Create a Culture of Delegated Decision-Making

Will Ahmed is the Founder and CEO @ Whoop, the company on a mission to unlock human performance with their wearable device that is your digital fitness and health coach. To date, Will has raised over $400M for the company with the last round valuing Whoop at $3.6BN and with a cap table including the likes of Softbank, Accomplice, Founder Collective, Foundry Group, IVP and more. In Today’s Episode with Will Ahmed You Will Learn: 1.) How Will went from being a professional athlete and college student to founding one of the hottest startups in fitness and healthcare? What are the similarities and differences of being an athlete and being a CEO? 2.) What does Will mean when he says, "there is value in the struggle early on"? How does Will advise founders on when to give up vs when to stay the course? If Will had not struggled with funding in the early days, would the Whoop journey be different? How does Will advise founders when it comes to taking funding when it is on the table? What are the nuances to this? 3.) In what way does Will believe "realism is overrated"? When does Will believe it is good to be realistic? In what ways can it be good to be idealistic? How did Will get some of the largest sports stars on the planet to use Whoop in the early days? Why did Will always refuse to pay sports stars to use Whoop? What were the benefits of doing this? 4.) How does Will define high performance? Why does Will believe it is crucial for leaders to disassociate their own personal feelings from the progress of their company? What advice does Will give to leaders in an attempt to do this? What has Will done to be a better CEO in the last year? What does Will believe are his biggest weaknesses as a CEO? Item’s Mentioned In Today’s Episode with Will Ahmed Will’s Favourite Book: Shoe Dog: A Memoir by the Creator of NIKE

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

• 0:00Harry Stebbings?

  Welcome back. This is the first 20 VC of 2022 and what a year of episodes, guests and new podcasts launching we have ahead of us. However, with it being the new year and the start of January with many looking to change behaviours, adopt healthier behaviours and routines, I thought it'd be a really timely episode today as we welcome an individual reshaping the world of health and fitness. Will Ahmed, co-founder and CEO at Whoop, the company on a mission to unlock human performance with their wearable device that is your digital fitness and health coach. To date, Will has raised over $400 million for Whoop, with the last round valuing Whoop at $3.6 billion and with a cap table including the likes of SoftBank, Accomplice, Founder Collective, Foundry Group, IVP and more incredible names.

• 0:41Harry Stebbings?

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• 1:23Harry Stebbings?

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• 2:08Harry Stebbings?

  And finally, Sprig, formerly known Is the in-context user research platform that is fast and reliable, providing targeted micro-surveys, video questions and more, making it possible to obtain qualitative insights at the speed and scale of analytics. Sprig even allows you to target your actual users during key moments, throughout their product journey, helping you to ensure every product decision is customer-informed. But do not take my word for it. Sprig is trusted by the world's most innovative companies, including the likes of Square, Dropbox and Loom, to name a few. Head over to sprig.com today to find out more. But that is enough from me, so now I'm so excited to hand over to Will Ahmed, co-founder and CEO at Whoop.

• 2:54Speaker 01

  You have now arrived at your destination.

• 2:57Harry Stebbings?

  Well, this is such a joy to do. I've heard so many great things from Jeff Fagin and Eric Paley, so thank you so much for joining me today.

• 3:03Speaker 02

  Thanks for having me, Harry.

• 3:04Harry Stebbings?

  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.

• 3:18Speaker 02

  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 over-train. I think other athletes will go through periods of under-training 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.

• 4:03Speaker 02

  I was someone who was 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 human body and that ultimately became the business plan for whoop. I think I became an entrepreneur before I even knew what an entrepreneur was.

• 4:28Harry Stebbings?

  Can I ask, when we think about the mindsets, you spoke about kind of that very driven mindset that you had as an athlete. When you think about the mindsets of athletes and entrepreneurs, how did being an athlete impact or pay you for the life that you have now as an entrepreneur?

• 4:41Speaker 02

  Well, I certainly think that there's a component of being an individual contributor and you want to be as prepared as possible as an individual. I think there's a point of view on being a part of a team and certainly what role do you function in a team. Certainly having been on teams my whole life, I think helped me prepare for being a CEO. I mean, being captain of a sports team of 15 people is in a way similar to starting a small group of people on a problem. So, you know, I think there's a lot of overlap. I think generally speaking, playing sports and being an athlete prepares you for a lot of good things in life.

• 5:12Harry Stebbings?

  I do want to ask you, you said the early work that you did there at Harvard led to the kind of the first business plan for whoop. When we look today at whoop and the $4 billion 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?

• 5:34Speaker 02

  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 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 businesses going up so fast. And then all of a sudden, something happens and it's kind of a very dark spell 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

• 6:19Speaker 02

  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 appreciative, frankly, of when things start going well. When you have a lot of near-death experiences early on, it also helps you put into context what is a real challenge, like what is existential versus what is just the daily, you know, rhyme and reason of building a technology business. And so that perspective can be quite valuable, too.

• 6:59Harry Stebbings?

  Well, can I ask, I tweeted this morning about VCs today foie gras in startups, which is essentially we shove so much cash down your throat so early on that you kind of implode. If we took Whoop in 2010 to Whoop in 2021, you would have so much cash stuffed down your throat because you are an eloquent, smart Harvard grad with a massive consumer brand idea, you would have a lot of money very fast. Would you have done things differently? And do you think it would have actually been detrimental? Because I think it's actually very detrimental to have too much money too soon, like everyone has today.

• 7:29Speaker 02

  Well, I think it depends on the type of business that you're building. You know, Whoop was a business that was really designed with a lot of the ambition upfront. You know, I wrote this paper in 2011 as a student called "The Feedback Tool: Measuring Intensity Recovery in Sleep." Our three main metrics 10 years later are strain recovery and sleep. Now, it took us years and years to actually build the technology to deliver that value to our consumers in a simple way, in a convenient way, to get the technology to be small enough, to get the technology to be accurate enough, to get to feel good 24/7 to wear. And I bring those things up, Harry, because, you know, it was an expensive problem that we were tackling, and it took a really long time. And it wasn't one of those businesses where we were kind of anxious to be, you know,

• 8:13Speaker 02

  tweaking and tweaking and pivoting and pivoting what the actual product was. Like, building this technology and this product was something of a straight line. There was all kinds of other pivots related to business models and go-to-market strategies. But the actual technology itself was a straight line. And so I think for businesses that have that ambition, where they're trying to build something that's never existed before, and frankly, it has a lot of existential technology risk, which our business certainly did early on, I do think raising a lot of capital can be helpful. And so from that pers- I probably would have raised this as much capital as I could have.

• 8:43Harry Stebbings?

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

• 8:51Speaker 02

  Well, realistically, ninety percent of startups fail. So the ten percent 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, 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 person 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.

• 9:37Speaker 02

  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 without us paying them. You know, I said, we're not going to sponsor professional athletes. They're going to either use this technology because it gives them enormous value, or they're not going to wear it. But guess what? If it delivers the value, I think they'd want to pay for it. And if it doesn't deliver the value, I don't think there's any amount of money we could pay them to get them to wear it. And people said, well, that's unrealistic. You should really be giving these guys equity and give them equity. And then, you know, they'll endorse the product because they're owners. And I said, you got the wrong point of view on that.

• 10:22Speaker 02

  So that was one example of how being unrealistic, I think, served us well.

• 10:26Harry Stebbings?

  Can I ask, was there ever a time where being unrealistic actually got you in trouble? It either went wrong, you were too unrealistic, you pushed the boundaries too far on your own imagination, Will?

• 10:35Speaker 02

  Well, I think good examples of being unrealistic often relate to engineering timelines and technological ambition. And sometimes it's hard to know where that line is. So you say, well, you want the V one to have, you know, a five day battery life, and maybe that helps drive to a Two day battery life when otherwise you would have gotten a one day battery life. There's a little bit of that sort of tension and you sort of work through those things. I think mostly this idea of realistic versus unrealistic is just something for founders to be asking themselves. What are certain areas of development where we have to do things that no one else has done? So in the case of Whoop, that was having the right influential people falling in love with the product. That was building technology that'd never been built before. You know, I had fairly realistic expectations about what our business model could be.

• 11:18Speaker 02

  But then actually we learned that that also needed to be something that was unusual. So there are these different categories you have to ask yourself, I think, along the way of building a business. Like, how disruptive does it actually need to be? What things do you really need to disrupt? And what are other areas where you should just borrow from successful founders or successful companies?

• 11:35Harry Stebbings?

  The one thing I often think with founders is 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?

• 11:56Speaker 02

  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 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 24/7 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.

• 12:41Harry Stebbings?

  I mean, speaking of why startups fail, you said to me before that most startups die of unforced errors. What do you think are the most unforced errors that are common to startups failing that founders fall victim to?

• 12:51Speaker 02

  Well, the one you see a lot is founder conflict. I think it's something like 65% of startups fail because the co-founders get in some massive disagreement or can't work. Together anymore. In my case, John Capulupo, who's our Chief Technology Officer, who I met when he was 19, he dropped out of Harvard to build this business with me. And Aureliani Nicolai, who graduated the same year as me at Harvard, who's our Lead Mechanical Engineer, you know, the three of us are still going nine years later. And that's probably one of the things I'm most proud of about building Woo, because for a company that had to overcome a lot of challenges, especially engineering challenges, you know, the fact that the three of us are still marching, I think was a sign that despite disagreements along the way and differences of perspective, like, we were able to really hug it out still. And I think many founders have to focus on that.

• 13:35Speaker 02

  They have to really not let them be the reason that they can't execute on that vision.

• 13:39Harry Stebbings?

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

• 13:43Speaker 02

  The first thing is I found partners that are incredibly complementary, that much overlap in the things that that we're good at. I mean, John Capulupo 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 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 complementary skills,

• 14:26Speaker 02

  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 it 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.

• 14:44Harry Stebbings?

  When you have very different skills, I think one thing that can be a challenge is kind of prioritization and the understandings around why you prioritize, what you prioritize, and when you prioritize it. I think a 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?

• 15:10Speaker 02

  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 disruptive 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

• 15:55Speaker 02

  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.

• 16:15Harry Stebbings?

  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 that 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?

• 16:33Speaker 02

  Well, this is a little bit of 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,

• 17:17Speaker 02

  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.

• 17:45Harry Stebbings?

  What've been your biggest lessons in terms of how to prevent drama?

• 17:48Speaker 02

  Oh, I think the first is just squash it as fast as possible. You know, if someone comes in your office and they're like, hey, so and so, I don't know if they're executing well on this. I'm nervous about that. I'm like, all right, let's go get so and so. Let's talk about it. You know, it's just like boom, you know, try to squash it as fast as possible. Sometimes there's more complicated issues than that and you have to work through it. I think drama in a startup is horrible. You really want everyone to feel like they're pulling in the same direction and you should try to squash drama as much as possible. I think chaos is actually just sort of a normal and healthy feeling for a startup to be in. And I think the faster you're growing and even the more successful you are, the more chaotic it can feel. So I've kind of grown to embrace that feeling of chaos and, you know, be able to smile and appreciate it. But I do have a real allergy towards drama.

• 18:33Harry Stebbings?

  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?

• 18:46Speaker 02

  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. Cause 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.

• 19:20Harry Stebbings?

  My other question to you is like, on the chaos side, I get you in terms of embracing chaos, but you're at a stage now, you're worth, you know, whatever, $4.2 billion.

• 19:30Harry Stebbings?

  Amazing number, but it's like you're going to 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?

• 19:47Speaker 02

  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 join.

• 20:28Speaker 02

  And it helps 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 culture of control, especially top-down control, where I want to know every decision that's being made today. That's going to require a ton of meetings. It's going to require a ton of committees and it's going to slow things way down.

• 21:13Speaker 02

  And so I got comfortable over time with just continuing to empower and empower and empower and push more and more decisions down such that we can move at a really fast pace. Because the more people who feel empowered to make decisions every day, the faster things are going. And for Whoop, we've really pushed towards pace over control.

• 21:31Harry Stebbings?

  Can I ask, when 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 hiring. 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?

• 21:48Speaker 02

  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 gonna 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

• 22:33Speaker 02

  to 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 gonna be making decisions. You do not need everyone's buy and you gotta move fast. And when you say that, it just changes people's attitude in such a positive way. It's amazing.

• 22:50Harry Stebbings?

  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?

• 23:01Speaker 02

  I tend to lean in on trust, you know? I like to hire people and believe that they're gonna 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 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 wanna 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.

• 23:43Harry Stebbings?

  Can I ask you a blunt question then? How do you think about retaining that at scale? You know, I'm not sure, how many employees do you have?

• 23:50Speaker 02

  About, I think, six hundred and fifty.

• 23:51Harry Stebbings?

  Six hundred and fifty. That's a rock star software engineer, rock star. Will, you're a busy, busy guy, the CEO of a four point two billion dollar company. When they were fifty, 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 whoever, a 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?

• 24:19Speaker 02

  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, six hundred people. You know, for example, I do a call with everyone 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 Whoop 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.

• 25:02Speaker 02

  Like, what's the experience that you have in the first two weeks or the first thirty 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. It's like onboarding. How quickly can you get someone bought into the org and moving fast?

• 25:18Harry Stebbings?

  How many direct reports do you have, Will?

• 25:20Speaker 02

  I've got eight reports.

• 25:21Harry Stebbings?

  Gosh, is that manageable?

• 25:22Speaker 02

  It is because they're all very, you know, they're very capable. A lot of my job is listening to them, frankly, and letting them tell me what we should be doing.

• 25:29Harry Stebbings?

  Can I ask, we spoke about kind of scaling the org and 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?

• 25:42Speaker 02

  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, twenty one, twenty two years old. Whoop wasn't just the first company I, you know, I started, it was my first job. Job. So I had a lot tied up in how the company was performing. And it'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,

• 26:27Speaker 02

  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 individual. Because then you're not living on the yo-yo that is your company's performance. You're really focused on how am I the individual, the CEO, the founder, the entrepreneur, whatever, growing? And so that was something that was very important for me to do. I got into meditation. It was deeply helpful for me in building the company. I've been doing transcendental meditation for about seven years now, every day.

• 27:07Harry Stebbings?

  Can I ask, well, my, so tiny VC was my first company, job, everything in between. And 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?

• 27:31Speaker 02

  Well, identity and performance, I think are slightly different thing. You know, it's okay, I think, if your identity is, you know, closely related 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 companies. 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. Point, it's probably close to fifty people, but definitely between fifty and a hundred people.

• 28:14Speaker 02

  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 could 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 focusing on that sort of manager role. So those are things that I've tried to think about as the company's grown and as I've grown is like, what degree to which am I operating like a manager and what degree am I trying to dive in on things and operate like an individual?

• 28:54Harry Stebbings?

  Can I ask a final one? And it's bluntly, and this was from Fagin. But when we look at like funding journeys, one of the biggest 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 fundraise story first? And then second, how did you get Middle East money when you just had weeks of runway left?

• 29:13Speaker 02

  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.

• 29:55Speaker 02

  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.

• 30:03Harry Stebbings?

  No, it totally is. A 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 see Whoop everywhere. Like, what was that inflection point over the last seemingly year or maybe nine months even? But something Has changed. What do you think it was?

• 30:21Speaker 02

  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 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, 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.

• 31:06Speaker 02

  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 upfront 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 times revenue, which isn't great. And Peloton, as a private company, was trading at about 20 times revenue. And so I was asking myself, well, do we want to grow up to look like Peloton or Fitbit? And so that sort of combination of things made Whoop transition to being a subscription business. And in May of 2018, we made that transition. And then the technology was also at a place where it was pretty rock solid and pretty special. And so here we are.

• 31:51Harry Stebbings?

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

• 32:05Speaker 02

  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.

• 32:46Speaker 02

  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 today for thirty 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.

• 33:02Harry Stebbings?

  Well, I want to move into my favorite, which is a quick fire. So I say a short statement, you give me your immediate thoughts. Are you ready to dive in?

• 33:08Speaker 02

  Let's do it.

• 33:09Harry Stebbings?

  Because what's the favorite book and why, Will?

• 33:10Speaker 02

  Well, one from a whoop standpoint was I really enjoyed the book Shoe Dog by Phil Knight, which of course is about building Nike. And the reason I found it refreshing was, you know, they spent years and years as blue ribbon sports, you know, trying to figure out how they could build the very best shoe. And in reading that story, it at least continued to inspire me in building whoop because we spent so many years building that technology to be what we thought was great technology for the market.

• 33:34Harry Stebbings?

  Fagman told me you have the highest level of fortitude and resilience of any founder he's ever worked with. What fundamentally drives you so much, Will?

• 33:43Speaker 02

  Well, that's high praise coming from Jeff Fagman. You know, I do think that I have a, an ability to compartmentalize challenges and to be able to continue focusing on that end state and really visualizing that end state, whatever it may be. In the case of, you know, building a business, free revenue that's got a huge technology cost. It's really picturing that, hey, one day, millions of people are going to be wearing this and it's going to be improving their health. And if you can really visualize that, it helps you, I think, overcome enormous challenges along the way and it keeps pushing you.

• 34:12Harry Stebbings?

  Will, tell me, this one's personally just interesting. What's your workout routine?

• 34:16Speaker 02

  You know, I work out with a trainer a few days a week. I still play squash once or twice a week. I actually play in a soccer league, which is enormously fun and a little bit dangerous. I'll occasionally do like a yoga class or, you know, some kind of a spin class. You know, I like to mix it up and then I also play golf from time to time.

• 34:33Harry Stebbings?

  How many hours sleep a night do you have, Will?

• 34:35Speaker 02

  Well, the secret to sleep is the amount of time you spend in bed, being quality sleep. And so I would say at this stage in my life, I'm still mostly optimizing as an entrepreneur. And because of that, my mindset is how much time can I spend in bed that actually delivers REM and slow wave sleep? If you spend seven hours in bed, Harry, as you probably know, you could end up with thirty minutes of REM and slow wave sleep, or you could end up with, you know, five and a half hours of REM and slow wave sleep. And figuring out all the little things you can tweak about your lifestyle or your routine to be higher on that spectrum, that can actually change your life. So I like to think I've figured a lot of those things out for myself. So, you know, I'm able to get, say, four to five hours of REM and slow wave sleep a night. And, you know, some nights I'm doing that with only six or seven hours in bed. Certainly, I like to get eight hours in bed, but yeah.

• 35:20Harry Stebbings?

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

• 35:23Speaker 02

  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, 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.

• 36:03Harry Stebbings?

  Can you help me out here? When I don't drink, my REM and my deep sleep are shit. When I do drink a lot, I sleep perfectly well. I wake up feeling great, don't get hangovers, I feel refreshed. What is wrong with me?

• 36:16Speaker 02

  Well, I might be questioning the quality of how you're measuring that data.

• 36:19Harry Stebbings?

  So as much time REM, so you got like two hours twenty deep and an hour thirty REM, compared to like last night, didn't drink at all, and I have like thirty minutes on both.

• 36:28Speaker 02

  You know, there are certain individuals who, we've seen one glass of alcohol can actually make them sleep better. It tends to get slippery from there, so two to three, three to four, then all of a sudden, your sleep really should be disrupted. It's possible too that the nights that you choose to drink are nights, there's other circumstances. So maybe you're with family, or you're with friends, or perhaps you're A lighter mood, which then helps contribute to positive sleep. So there could be some lurking variables here, but we'd have to spend a little bit more time on that.

• 36:57Harry Stebbings?

  What does your morning routine look like, Will?

• 36:59Speaker 02

  I wake up, I get out of bed, I take a freezing cold shower, I put on my clothes, I meditate for twenty two minutes. I give my wife a few kisses if she's still in bed and boom, I'm out the door grabbing coffee and a breakfast sandwich. And at my desk within an hour of being awake.

• 37:16Harry Stebbings?

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

• 37:19Speaker 02

  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.

• 37:54Harry Stebbings?

  Will, you can have a billboard anywhere with anything on it. What do you have on it? And what does it say on the billboard?

• 37:59Speaker 02

  I think keep going.

• 38:00Harry Stebbings?

  Hashtag marriage.

• 38:02Speaker 02

  Yeah, well, that's been a bit of a talk track in the back of my mind for so many years in building this company. And I think it's good advice often, whether you're experiencing great times or low times, just continue on.

• 38:13Harry Stebbings?

  Yeah, no, listen, I totally agree. It was my father who said, the biggest problem with marriage, Harry, is that people conflate happiness with endurance. Happiness is not a part of marriage. It's just simply a game of can you endure?

• 38:24Speaker 02

  Well, there you go.

• 38:25Harry Stebbings?

  I do want to finish on the probably the best question of all, though, you know, when we look ahead, what does Whoop look like in five years? How big can this be, Will?

• 38:32Speaker 02

  I think the mission of improving health is very relevant, especially as the world endures a global pandemic related to health. I think that Whoop as a technology can continue to innovate and continue to make it easier and easier for people to understand their bodies and improve their health. I think that over time you'll see us moving much more directly into the core healthcare world and interacting with doctors and medical professionals. And I'm really excited about it. It's an amazing, exhilarating mission to be a part of, and I'm grateful for all the people I get to work with every day.

• 39:03Harry Stebbings?

  Well, this has been so much fun to do. I'm sorry for the completely wayward questions and the asking of advice. You should invoice me for the consultation, but seriously, this has been so much fun to do. So thank you so much for joining me.

• 39:13Speaker 02

  You've been great. Thank you, Harry.

• 39:17Harry Stebbings?

  That really was so much fun to do there with Will and I absolutely love that definition of high performance. Such an exciting time ahead for Whoop. And if you'd like to see more from us behind the scenes, of course you can, on the 20minutevc.com. We always love to see you there. But before we leave you today. A Harvard management company is constantly seeking out the next generation of great investors and entrepreneurs. HMC has managed Harvard University's endowment for nearly 50 years and was one of the first institutional investors in venture capital. Their experience and long-term investment horizon makes them ideal partners to get world-changing ideas on a path to viability and success. They work as a true partner, providing insightful perspectives to help managers succeed. I personally have had the pleasure of working with the HMC team and can say that they're

• 40:00Harry Stebbings?

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