WHOOP Founder Will Ahmed on the Pivot That Turned a Struggling Startup Into a $10.1 Billion Company

Most startup stories become deceptively simple in hindsight.

A founder sees an opportunity. Builds a product. Raises capital. Finds customers. Scales.

Will Ahmed’s story with WHOOP is a useful reminder that the reality is usually much messier.

Ahmed started WHOOP as a young Harvard athlete trying to solve a problem he had experienced personally: he was training hard, but he didn’t really understand what was happening inside his body during the other 20-plus hours of the day.

That curiosity eventually became WHOOP, the wearable health technology company that Ahmed says is designed to continuously measure sleep, recovery, exercise, and overall health.

Today, the company has reached a reported valuation of $10.1 billion. But in a conversation on Inside Blackstone, Ahmed spent surprisingly little time talking about the valuation itself.

Instead, he talked about rejection, near-failure, business model reinvention, customer behavior, sleep, data, and the mindset required to keep building when the obvious path stops working.

For entrepreneurs still somewhere in those messy middle chapters, those lessons may be much more valuable than the headline number.

The Opportunity Was Hidden Outside the Workout

Ahmed’s original insight came from his own experience as a college athlete.

Wearable technology was still relatively primitive, and much of the market focused on what happened while someone was exercising.

Ahmed saw the opportunity differently.

The workout itself might take two hours. A game might last several hours. But what about everything happening to the body during the rest of the day?

That became the deeper problem WHOOP wanted to solve: understanding the body continuously rather than only during moments of activity.

Ahmed described a distinction that every founder should pay attention to:

“Customers tend to be better at explaining problems than explaining solutions.”

That idea has enormous implications for product development.

Customers can usually tell you where something hurts. They can describe a frustration, bottleneck, fear, or unmet need.

But asking customers to design the answer can trap a founder inside what already exists.

Ahmed believed athletes needed a clearer picture of their bodies across the entire day—even if the market wasn’t explicitly asking for that product yet.

For wantrepreneurs, this is a useful place to start: listen carefully to the problem, but don't assume the customer has already imagined the best solution.

Fall in Love With the Problem, Not the Outcome

Ahmed’s entrepreneurial philosophy can be distilled into another simple idea:

Obsess over the problem.

He cautioned against beginning the entrepreneurial journey primarily with the goal of making money.

In WHOOP’s early days, he said, the future financial outcome barely entered his thinking. The question was whether the company could solve an important problem—and how meaningful the impact could become if it did.

That orientation matters because startups rarely follow the original plan.

If you become emotionally attached to one particular product, pricing model, distribution strategy, or feature set, changing direction can feel like admitting failure.

If you are attached to the problem instead, changing the solution becomes much easier.

WHOOP would eventually need exactly that mindset.

The Business Was Working—and Still Failing

One of the most instructive moments in WHOOP’s story came around 2018.

The company had already existed for roughly six years. Consumers were buying the product, and the people using it demonstrated strong engagement.

That sounds encouraging.

There was just one major problem.

Not enough people were buying it.

Ahmed recalled the company facing questions about whether WHOOP had reached a dead end. Was it simply a product with a small group of passionate users but no scalable market?

For many founders, that is one of the hardest situations to diagnose.

The customers you have love what you built.

Retention looks promising.

The technology works.

And the business still isn't working.

Ahmed said something revealing about moments like this:

When something becomes sufficiently broken, it gives you permission to reinvent it.

WHOOP did.

The Pivot That Changed WHOOP

The company moved toward a membership model.

That decision changed more than WHOOP’s pricing.

It changed what the organization optimized for.

Instead of primarily thinking about selling a device, Ahmed said WHOOP became intensely focused on retention, engagement, and serving the member.

Recurring revenue also made the business more attractive to investors.

The lesson is bigger than subscriptions.

A business model determines what behavior your company is rewarded for.

A transaction-based model may push an organization toward acquisition and unit sales.

A recurring model forces a different question:

Are we providing enough value that someone wants to stay?

For early-stage entrepreneurs, that question can expose weaknesses long before revenue numbers do.

Fundraising Is a Skill—and Rejection Is Part of the Training

Ahmed’s path to financing wasn't smooth either.

The interview references an extraordinary stretch of roughly 143 fundraising meetings without getting the desired yes.

Ahmed’s interpretation of that period is useful because he doesn't romanticize the rejection.

Some investors may have doubted the market.

Some may have worried about enormous competitors such as Apple, Nike, and Google.

Some may simply have looked at a young founder and concluded that the risk was too high.

And Ahmed also acknowledges something founders don't always want to admit:

He probably wasn't very good at fundraising yet.

Fundraising, he argues, is a skill.

You improve by doing it.

And ultimately, the exercise becomes less about persuading everybody and more about finding the people who believe.

His broader advice to founders is even simpler:

“Keep going.”

Not through blind persistence. Not by repeating the same mistake forever.

By continuing to make good decisions.

One decision, then another.

Ahmed describes it as stacking good decisions.

That may be one of the most practical definitions of entrepreneurial resilience.

You don't need to solve the next five years today.

You need to make the next intelligent move.

Be Most Careful When Things Are Going Well

Interestingly, Ahmed says WHOOP's most dangerous moments haven't necessarily come when the business was struggling.

Difficulty creates focus.

When survival is obviously at stake, teams become intensely concentrated on solving the problem in front of them.

Success creates a different risk.

Optimism expands.

Confidence grows.

Warning signs become easier to ignore.

Ahmed’s advice is to become more paranoid when things are going well.

That doesn't mean operating from fear.

It means recognizing that momentum can hide mistakes just as easily as adversity can reveal them.

High Intensity. High Humility.

WHOOP eventually developed a cultural framework for the kind of people who thrived inside the company: high intensity, high humility.

High intensity means having the internal drive to push, improve, and accomplish difficult things.

High humility means recognizing that you don't have every answer and that meaningful work requires collaboration.

Either characteristic alone can create problems.

Intensity without humility can become arrogance.

Humility without intensity can become passivity.

The combination creates something more useful: ambitious people willing to challenge themselves without assuming they are always right.

For founders building their first teams, that is a valuable hiring lens.

Don't only ask whether someone is talented.

Ask how they pursue excellence—and how they behave when someone else has the better answer.

The Bigger Lesson Behind WHOOP

WHOOP may increasingly operate at the intersection of wearables, health data, AI, and healthcare.

Ahmed believes continuous health monitoring could eventually help people understand not merely what happened to their bodies, but what might happen next.

Yet the entrepreneurial lesson behind that vision is surprisingly timeless.

WHOOP didn't reach its current position because Ahmed perfectly predicted every step of the company’s journey.

The company survived because the team stayed attached to the problem while remaining willing to reinvent the solution.

They changed the business model.

They endured investor rejection.

They learned from customers without simply asking customers to design the future.

And they continued making decisions when the outcome was uncertain.

That may be the most useful takeaway for anyone waiting for the perfect business idea or wondering whether their current obstacle means they should quit.

You don't need certainty.

You need a problem worth obsessing over—and the willingness to keep making the next good decision.