MachinePix Weekly #51: Will Ahmed, founder & CEO, WHOOP

Will talks about standing out from a crowd of competitors, and building a culture of constant improvement. This week's most popular post was a century-old tool that still feels sci-fi ⚙️

This week I sat down with Will Ahmed, the founder and CEO of WHOOP. WHOOP is a fitness band targeted towards performance athletes that has not only survived but thrived against products from Nike, Apple, and Fitbit.

What I thought would be just a conversation about product design turned into a long discussion of perfecting self and company. I won’t spoil the specifics, but Will is a very intense and thoughtful leader.

The most popular post this week was a fractal vise. I’ve never seen anything like this before, and I thought it was modern design—but it turns out it’s almost a century old. Does anyone know why these designs fell out of favor? There’s a full restoration video by the excellent channel Hand Tool Rescue.

I’m always looking for interesting people to interview, have anyone in mind?


Interview with Will Ahmed

This interview is actually part of a fun triptych, because I previously spoke to Chrissy about building the Apple Watch and Eric about building the Pebble.

What was the most interesting thing you learned from the Apple Watch conversation?

I'm put on the spot now. Apple has a reputation for amazing industrial design, very product driven teams—which is true—but the untold story is the armies of people whose jobs are just the details of operations and manufacturing. Which segues into my first question: when you launched WHOOP, Fitbit and Jawbone were in market; what was the driving differentiator for WHOOP that compelled you to start against these odds?

I was always interested in sports and exercise and measuring the human body. I was a college athlete who would overtrain, so I just got interested in this space through my own personal experience: I really wanted to measure and understand my own body as a college athlete. There wasn't anything on the market that made me feel like I could do that. Now, admittedly I started doing research in 2010 or so, so this was a little bit before the Nike FuelBand. The Fitbit would have been an early stage startup.

I actually met James Park, the CEO of Fitbit, at a recruiting fair my senior year of college. It was a big auditorium and he was doing the pitch for why we should join Fitbit. I didn't want to join Fitbit, but I was really interested in the company. It was me, and only three other people showed up. And so three people wanted a job and I wanted to start a company. I got to ask James a bunch of interesting questions, and I knew Fitbit was going to go on from there to be a big business, but it was a very different type of company than the one I was interested in starting. 

But back to your question: The key for WHOOP, early on—and it's probably still the key for WHOOP today—is that we wanted to be able to accurately measure the human body in the sense of deep physiological information. And we wanted to be able to tell you what to do with that information and give you prescriptive coaching. So that was really the framework for WHOOP, and I think it represents a lot of our differentiation today.

While other fitness bands have waned, WHOOP has managed to thrive—how do you stay ahead of the pack?

Well, we have stayed very focused. initially the technology was intended for the best athletes in the world, and then it was for serious fitness enthusiasts and then for recreational enthusiasts. And now it's starting to feel like it's for everyone. And because we were very focused, we made very specific decisions about the hardware, what it should do, and what it shouldn't do.WHOOP is amazing for all the things that it does as well as for all the things that it doesn't do. We don't have a screen, we don't have a microphone, we don’t have speakers. You can't call an Uber with your WHOOP strap.

But in terms of health monitoring, I think we’re really the best game in town. And we’re very focused on continuous health monitoring. So that gives us an advantage again, because we were so focused on what this thing needed to do. It became less important to have all these me-too features. I felt like so many wearables: Jawbone, Fitbit, Fuel Band, and in some ways, even the Apple Watch, were kind of building on each other and taking a lot of what the prior had done and continuing to do it. For WHOOP, we built our own path.

So it sounds like the WHOOP philosophy has stayed pretty consistent. Were there any times where it felt existentially challenging to stay dedicated to the philosophy?

Certainly in the years of 2012 to 2016, I think there were a lot of dissenting points of view with our vision. A lot of people were encouraging us to add step counting, to add a screen, to go into the mass market quickly, to pay athletes to wear our product. We were very stubborn about a lot of things and we kept coming back to our true purpose, which was “what do we need to measure? How do we make it really accurate? How do we tell you what to do?” That was our focus. And it was a really narrow but important guiding lens. I also believed that we needed to build the best product in the market.

You look at other companies that have come and unfortunately gone in the space, all of them at one point or another won distribution. Fitbit is one of the best distribution stories of the last 20 years. I mean, every year they were five-x-ing their unit volumes. That's very hard to do. Jawbone sold millions of units. The FuelBand sold millions of units. So at one point these were commercial successes from a distribution standpoint and even a sales standpoint, but they were product failures.

For the most part, a high percentage of people would wear the products and take them off. And a lot of our lens for building WHOOP was how to create technology that someone never took off for the rest of their life. And it was more important to us to get a smaller number of people to do that than it was to get a lot of people to buy our product. Again, being really focused on that helped us get to at least the stage where we're at today.

What’s your craziest experience from building WHOOP?

WHOOP as a business went through very hard times. It took us a long time to build the technology to be accurate. It took us a long time to get to market and really build a business model at various points. There were challenges raising capital because hardware is hard and there were a lot of wearables in the market at various points in time.

I mean the company probably had ten near-death experiences. There were a lot of times when the company persevered, because we had to or we would die. And I think that the great thing about having been through that and coming out the other side is it puts in perspective for you the spectrum of problems that you can have.

I think one key to managing a business or leading a company is to have a fairly steady hand. And if you've been through a lot of challenging stuff and come out the other side, it in turn helps you become a leader.

It’s exceptional to see the founder of a company right out of college as the CEO a decade later. What were some of the toughest unforced errors that you made building WHOOP you would warn your past self about? What advice do you have for new entrepreneurs?

Such a great question. I think the first thing for any entrepreneur, especially a young, first-time founder is to separate the performance of the business from your own performance. Those are two independent things. The nature of building a company from scratch or doing things never done before is that there are going to be real issues and challenges that come up. You don't want to feel like if the business has a bad day, you're failing, and if the business had a good day, you're winning—otherwise you're living on a roller coaster. That's totally unproductive. Plus you don't want your self-identity to be completely tied to this business because that's not particularly helpful either.

So one major step for me was learning to separate those two things and realizing that WHOOP could have a good day or a bad day independent of my own performance. In fact, I could just focus on getting a little bit better every single day as a leader or a manager or an entrepreneur. That in turn was gonna help me grow into being the CEO of what is now a 500-person organization.I would say that's one very big thing. 

Another key theme is learning at various stages of a company’s development the degree to which you're an individual contributor versus a manager. Somewhere around 25 to 50 people as an organization, it really starts to tilt towards being more of a manager. When you're in the earliest stages, you can stay up all night coding. You can fly around the world, meeting with people and raising capital or recruiting people or whatever. You can live a somewhat crazier lifestyle of being an entrepreneur. And you can also think about the business’ output being somewhat similar to your individual output.

But when you then start employing a large number of people on the team, like 25 to 50, the CEO job starts tilting towards being a manager. One hundred and up, to me, it's where most of your outputs should be as a manager. Most of the company's output is going to come from the entire team and you need to recognize the role that you're playing as a manager. And you need to make sure you’re thinking about your role appropriately on that continuum of individual contributor versus manager.

Another interesting thing that I think happens for founders is they have to decide what kind of culture they're trying to create. Do you want to be a company that moves really fast even if it means the company is at risk of creating bugs and mistakes? Do you want to be a company that has an extremely high level of control in which case you've got a slower decision making process, but you're able to make a lot of those decisions? How many checks and balances do you need in your business? What types of people are you looking to recruit? Are they more creative or are they more technical? All the above?

You have to start actually thinking very intentionally about these things because the culture is how people make decisions when you're not around. Culture is what scales, and you really don't scale as an individual. So the culture you create defines your organization. And it's why you see a lot of companies at some point have these cracks related to culture. Less so their business model or their brand, but really just the core culture of the organization. So that's just another area that as a founder, you have to pay a lot of attention to. 

Speaking of culture, you’ve clearly thought a lot about the impression you make as a CEO. What are some of the key pieces on the wall behind you?

There's a sketch of one of the first WHOOP straps ever, which was a bit of a leap for us because we thought the industrial design of the hardware was going to be pretty critical. And still today it has a very unique industrial design. It's mostly material. It doesn't have a watch base or a screen. It also has a modular charger, so you can charge WHOOP without ever taking it off your body. All of those things we designed in 2013 or 2014. And they were really first of their kind in the wearable space. And the fact that today, seven or eight years later, we have a very similar design—albeit smaller and more effective—speaks to the genius of that original design.

Another thing I've got behind me is a paddle that was gifted to me by the Navy SEALs. We do a lot of work with the SEALs—we’ve partnered with the SEAL Future Foundation. They were gracious and sent me the paddle that you get when you become a Navy SEAL. The paddle is an inexpensive object that I think speaks to the resourcefulness and grittiness that goes along with that culture.

What’s another product you really admire, or can’t live without? Other than work-related things.

Well absent this call, I was going to say AirPods because it was a very unique take on the headphone market. And I think it's one of the best products Apple's developed in the last 10 years. So I'll compliment the AirPods for half a second.

I’ve been thinking a lot more about brands and gravitating to brands. You know, I think good products are already pretty romanticized in the tech world. I think good branding isn't. It used to be sort of an afterthought in the venture capital world and in the technology world. And there's some reason for that—building a brand is more expensive and it takes time.

And pretty much everything in technology, especially in venture capital is about doing things fast and as efficiently as possible. So in many ways, brand building is sort of the antithesis of going fast and and being efficient.

To clarify, by “brand” you mean the culture right? Not just a design language or brand identity?

All of it. What does it mean when you see a Nike swoosh or Supreme backpack? You take a t-shirt and you put Supreme on it—and all of a sudden the t-shirt is worth $150. That's a pretty fascinating phenomenon. So branding to me is one of the most underrated things in technology. I think a lot of technology businesses have identities but don't necessarily have brands. Or their brands you could argue are a weak spot for them as an organization. You know, imagine Facebook came out with a refrigerator—what would you expect that refrigerator could do just based on the brand that you associate with Facebook? You'd kind of think it's tracking everything about what you eat and selling your information. hat's a fairly negative connotation that you would have with a big technology company coming into a new market.

It's just an interesting consideration in many ways. At WHOOP, we've thought about this since the early days of the company and we've tried to grow WHOOP to be a brand and to make health monitoring aspirational. If you wear something on your body 24/7, I think that says a lot about who you are and your identity. We want that to come across as being a very positive connotation. So for us working in high performance sports, working with elite athletes, working with researchers and doctors and Fortune 500 CEOs, they’re all contributing to making WHOOP a brand that is tied to performance.

So what are the brands you really admire?

There are brands that I feel do a really good job of being a brand. Nike is one of the best examples where all they have to do is put a swoosh on something and all of a sudden it has an identity and that's pretty amazing. Or look at a company like Red Bull and what they've been able to do. Outside of being an energy drink, they're pushing the envelope with action sports and performance and research.

I look at what fashion brands like the LVMHs of the world have done, and it's really hard. It's really impressive that they can create this whole identity with what they produce. I find it all fascinating and I think it's probably not that well understood in technology.

Have you heard of B Magazine?

No, what is that?

I’ll send it to to you—every issue they deep dive into a brand’s history and design and culture.

That's very cool. The last thing I'll add is that it's very popular in technology to talk about moats and defensibility, and that's important. Why I think it's silly that brand is so ignored is because brand is a clear, clear moat. If you can actually develop a brand around a specific market, it becomes a huge part of defensibility.

In some of your other interviews, you talk about reading 500 medical papers in college to understand how to be a better athlete—what opportunities are you excited about for personal health, given how technology has progressed?

Well, the potential of health monitoring is to dramatically increase human life span and meaningfully reduce healthcare costs. I’ll speak for WHOOP: WHOOP is able to tell you the 2, 3, 4 things that you need to change about your lifestyle or your behavior to be healthier and to improve. And so if you can have people making these meaningful lifestyle shifts and doing that at the age of 30 or 40 or 50, It can actually help them live years longer.

There is a lot of research showing that if you can keep your heart rate variability increasing or steady over time, you're going to increase your lifespan. One of the core things that we measure is heart rate variability. And one of the core things that we've been proving for people who've been on WHOOP for a year is heart rate variability. If you've been on WHOOP for twelve months, you have higher heart rate variability. You have a lower resting heart rate, you're getting more sleep and it's higher quality sleep. So these are the types of things that contribute to human lifespan.

We also want to dramatically change healthcare. The healthcare system is screwed up because it's very much centered on curative costs. Curative costs are expensive. Preventative costs are far less expensive. The promise of wearable technology is that it can tell you you're at risk for cardiovascular disease before you get cardiovascular disease. Or you're going to have a heart attack in a year, or you're about to have a heart attack, and you should go see a doctor. It can be a predictive tool. Most people are dramatically underestimating the potential of wearable technology and health monitors, because V1 of wearables was kind of underwhelming. And I don't think people realize how dramatically it's going to change the whole healthcare system. 

Any side projects you’re working on right now?

I definitely have some things I tinker with. I still play a number of sports. I've gotten into playing competitive speed chess online. In my free time I'll be playing three minute blitz chess, which is highly entertaining and pretty stimulating. I think it's probably my body craving the attention or decision-making rush if you will.

I am generally fascinated by design and of late architecture. I'm involved in a couple different design projects,  some related to WHOOP, some in my personal life.

Any favorite books or books you’re reading now?

A great book as it relates to business and building a business is Shoe Dog by Phil Knight, which is about creating Nike. What I liked so much about the book is he spends probably two-thirds of the book writing about the early stages of the company. Before it was even called Nike, it was called Blue Ribbon Sports and they were obsessed with trying to create a shoe that could help runners run faster. Their identity was in performance. And anyway, it reminded me of building WHOOP and our obsession early on with performance.

What’s your favorite simple (or not so simple) tool or hack that you think is under-appreciated?

I've got two: the first is learning how to meditate. I learned how to meditate about seven years ago. I do transcendental meditation, where you are effectively repeating a mantra for 20 minutes, 22 minutes to be exact. You can do it once or twice a day. That’s really changed my life and it made me a much better leader, husband, son, friend, et cetera. I think meditating gives you this third person perspective to look at yourself throughout the day, not just while you're meditating, but really throughout the day. It lets you contemplate how you're performing or what you're saying and to operate in a less reactive way. It helps prevent being the worst version of being an entrepreneur, where you're saying things you didn't mean to say and getting angry when you shouldn't have gotten angry. I think meditation is so powerful in helping me stay in control of myself.

The second one, which is a little more fun, is cold showers. I started taking cold showers maybe two years ago, and there is a bit of a tie here to meditation, but more related to breathing. The only way you can do cold showers and sort of deal with the cold effectively is by learning how to breathe properly. I kind of got to know the Wim Hof guys. I never got too deeply into the Wim Hof breathing, but their whole philosophy on cold really resonated for me. And so now 100% of my showers are cold. 

Better for the environment too.

Yeah. It changes your life a little bit too. I think you want to do things that naturally make you happy in life. Yeah. Cold is one of those for me.

The Week in Review

If you like technology rabbit holes (which I assume you do, if you’ve read this far), there’s a great piece on the aerodynamics and design constraints of shuttlecocks.

Willow Creative has published a lot of great build logs. Seeing this reminded me of Star Wars prop and costume maker Frank Ippolito’s interview in MachinePix Weekly #26, where he notes that the best costumes often come from diehard fans.

Wing-in-ground (or simply ground-effect) vehicles have made experimental appearances throughout history, but I was genuinely and pleasantly surprised to learn that AirFish has been manufacturing and flying them.


I’ve been impatiently waiting to try a new pasta shape called Cascatelli, but it’s been sold out everywhere. I’ve been told the texture is very similar to Taiwanese “Q”.

I am always looking to connect with interesting people and learn about interesting machines—reach out.