The Diary of a CEOWhoop Founder: How I Built A $3.6 BILLION Company & BEAT Apple! Will Ahmed | E189
CHAPTERS
- 7:00 – 14:00
Origin Story: From Harvard Athlete to Health-Tech Founder
Ahmed outlines his upbringing, early fascination with sports and technology, and how overtraining as a Harvard squash player led him into deep physiology research and ultimately to the idea of continuously measuring the human body. He frames Whoop as the inevitable outcome of his obsession rather than a purely market-driven business brainstorm.
- •Grew up on Long Island with a tech-curious streak (iPod, PalmPilot, early voice-recognition tools).
- •Parents’ contrasting strengths—street-smart Egyptian immigrant father in finance, highly analytical mother—influenced his problem-solving approach.
- •At Harvard, he became obsessed with understanding training, overtraining, and the 'other 20 hours' outside workouts.
- •Read hundreds of medical papers, wrote a thesis on continuous human monitoring and metrics like intensity, recovery, and sleep.
- •Spent internships in hedge funds, investment banking, and private equity, seriously considering finance before founding Whoop at 22.
- 14:00 – 27:00
Obsession, Overtraining, and the First Steps into Entrepreneurship
Ahmed and Bartlett explore what makes someone pursue a topic to the point of obsession, using overtraining as an example and discussing how curiosity, not a polished business plan, pulled him into entrepreneurship. Ahmed describes building confidence via research, classes, and mentor feedback before finally committing to start a company.
- •Defines overtraining as prolonged overreaching leading to a depressed physiological and psychological state.
- •Overtraining felt like 'the ultimate betrayal'—working harder made him worse, not better.
- •Identifies himself as someone who goes deep down rabbit holes once interested in a topic.
- •Mentor at MIT challenges him: ‘Is this a paper or are you starting a company?’ catalyzing commitment.
- •Warns against perfectionism masquerading as preparation; you only learn many things after you take the leap.
- 27:00 – 37:00
Identity, Fear of Failure, and Founder Psychology
They dissect how founders often fuse their identity with their startup’s fortunes and how dangerous that can be emotionally and operationally. Ahmed shares how he gradually separated his personal worth from daily company performance and how obsession with the problem can pull you through low points—if managed correctly.
- •Ahmed felt he had 'become an entrepreneur before knowing what an entrepreneur was' because his idea consumed his thoughts.
- •Explains the unhealthy pattern: if Whoop had a good day, he felt great; if it struggled, he felt like a failure.
- •Argues that you can be improving as a leader even when the business is temporarily going sideways.
- •Separation of self and company identity was key to making hard decisions and leading with a steady hand.
- •Notes the additional pressure when your net worth is tied to the company—common among first-time founders.
- 37:00 – 54:00
Panic Attack, Meditation, and Building Emotional Resilience
Ahmed recounts a severe panic attack in 2014 that sent him to the hospital and became a turning point in how he built both his company and his life. He details his transcendental meditation practice and how years of consistent practice gave him a ‘third-person’ perspective on his thoughts and reactions.
- •Around age 24, with 30–40 employees and ~$20M raised, Ahmed was drinking too much and highly stressed.
- •Describes panic attack symptoms while driving: narrowing vision, numb fingers, strange taste—he thought it was food poisoning.
- •Hospital workup revealed it was a panic attack, prompting him to fundamentally rethink how he managed stress.
- •Adopted transcendental meditation (22 minutes every morning with a mantra) and has practiced daily for ~8+ years.
- •Outlines stages of benefit: initial ability to filter thoughts in-session, evolving into a 'third-person observer' that lets him anticipate and modulate emotional responses in real time.
- •Frames meditation and breath control as a 'superpower' for conscious decision-making under stress.
- 54:00 – 1:07:00
Living with Constant Runway Pressure and Learning to Cope
Ahmed describes an 18-month stretch where Whoop never had more than three months of cash and was once 48 hours from bankruptcy. He explains the weight of responsibility for a 50–70-person team and how surviving that existential threat permanently changed his sense of what counts as a crisis.
- •For about 18 months, Whoop’s runway never exceeded three months; at one point, bankruptcy was two days away without a signed term sheet.
- •He drafted farewell emails to investors, emotionally experiencing failure before the rescue deal closed.
- •The episode reframed future challenges (lower sales, poached talent, new competitors) as comparatively minor.
- •Emphasizes the importance of coping with stress rather than just avoiding it; stress indicates that something matters.
- •Admits to compartmentalizing burdens as CEO, sometimes shielding the team from full reality.
- •Recommends focusing on controllables—listing what you can impact and acting decisively—as a calming, clarifying exercise.
- 1:07:00 – 1:22:00
Daily Routine: Training, Hot-Cold, Sleep Hygiene, and Breathwork
Ahmed walks through his typical day and the health habits that underpin his performance as a CEO, from morning workouts and steam-room-to-cold-shower transitions to meticulous sleep setup and blue light management. He and Bartlett compare notes on breathwork and cold exposure, tying these practices back to physiology.
- •Night-before prep: lays out workout gear, work clothes, and writes 2–3 top priorities for the next day.
- •Sleep: cold, dark room; relatively consistent sleep window (11:30–12:00 to ~6:30); navigates differing sleep tendencies with his wife.
- •Morning: early workout with trainer, followed by a steam room and then an as-cold-as-possible shower.
- •Diet: protein-heavy breakfast (egg whites, avocado, bacon) after training.
- •Justifies morning workouts as controlling the controllable—ensures exercise happens before work emergencies arise.
- •Loves cold exposure for adrenaline hit, enforced proper breathing, and post-cold mood boost; notes sauna/steam’s potential longevity benefits.
- •Sees breathwork’s rise (e.g., Wim Hof) as a logical wave because breathing is a fully controllable lever.
- 1:22:00 – 1:36:00
HRV, Respiratory Rate, and the Physiology Behind Whoop
The conversation dives into the technical core of Whoop: heart rate variability, respiratory rate, and their roles in recovery, illness detection, and performance. Ahmed traces HRV’s history in elite sport and medicine, explains its relation to the autonomic nervous system, and illustrates how Whoop detected COVID via respiratory changes.
- •Defines HRV as variability between successive heartbeats (not a steady 1 second per beat even at 60 bpm).
- •Explains sympathetic vs. parasympathetic nervous system; inhalation skews sympathetic, exhalation parasympathetic.
- •HRV historically used by Olympic powerlifters (load planning), cyclists, CIA (lie detection), and cardiologists (heart attack risk).
- •Key HRV depressors: dehydration, alcohol, poor sleep, heavy training, psychological stress, conflict before bed.
- •Whoop uses HRV to quantify recovery and guide strain recommendations.
- •During COVID, elevated respiratory rate on Whoop often appeared 2–3 days before positive tests, reinforcing 'feelings are overrated' in early illness detection.
- •Story of a friend using Whoop data (plummeting HRV from stress and sleep deprivation) to change his schedule and meeting times.
- 1:36:00 – 1:49:00
Sleep Architecture, Blue Light, and Optimizing REM & Deep Sleep
Ahmed explains why REM and slow wave sleep are the 'magic' stages for brain and body, how blue light disrupts them, and what practical steps boosted his own sleep performance. Bartlett shares how seeing different REM/deep patterns on identical 8-hour nights fundamentally changed how he thought about rest.
- •Breaks sleep into awake, light, REM, and slow wave/deep; only REM and deep are strongly restorative.
- •REM sleep: cognitive repair, emotional processing, vivid dreams; lack of dream recall often signals insufficient REM.
- •Slow wave/deep sleep: physical repair; ~95% of human growth hormone released during this phase.
- •Same time-in-bed can yield wildly different restorative totals (30 minutes vs. 5+ hours of REM+deep).
- •Blue light from screens tells the brain to stay awake; Ahmed uses red-tinted blue-blocking glasses at night as a 'get-out-of-jail-free card' for evening device use.
- •He reports blue-blocking glasses as the single biggest boost to his own REM and deep sleep metrics on Whoop.
- •Links high REM with a softer amygdala response—better emotional regulation and lower fight-or-flight reactivity under stress.
- 1:49:00 – 2:01:00
Strain, Recovery, and Smarter Training Decisions
The pair unpack Whoop’s strain metric and how most recreational athletes mismanage intensity by doing similar-effort workouts too often. Ahmed explains how to pair strain with recovery scores to avoid overtraining and how other lifestyle factors like routine, diet, and mindfulness influence recovery speed.
- •Strain is a 0–21 score reflecting cardiovascular load based on time spent in elevated heart-rate zones.
- •Most amateurs cluster around the same strain (e.g., 12–13) every workout, ignoring their body’s recovery state.
- •Guideline: low recovery days may warrant very low strain (walk/rest); high recovery days justify much higher strain (16–18).
- •Product philosophy: not just telling you what happened (steps, heart rate) but what to do next (how hard to train today).
- •Recovery improvements come from sleep quantity/quality, hydration, nutrition, carefully chosen supplements, meditation/breathwork, and especially consistency (sleep and even workout timing).
- •Ahmed avoids naming HRV as the single 'favorite' metric, stressing the power of integrating multiple signals into actionable guidance.
- 2:01:00 – 2:06:00
Internal Culture: Paying for Sleep and Red-Recovery Policies
Ahmed describes how Whoop’s own workforce uses the product and how the company financially incentivizes good sleep and uses recovery scores for safety during COVID. These examples show a tight alignment between product, culture, and operations.
- •All employees are on a shared Whoop team; they can opt into a 'sleep bonus' scheme.
- •Hitting 85% average sleep performance over a month yields a $100 cash bonus on their paycheck.
- •During COVID, a 'red recovery policy' required employees with red recoveries to stay home, recognizing increased illness risk or existing sickness.
- •These programs reinforce the mission—using data to drive behavior change—and normalize talking about recovery, readiness, and health at work.
- 2:06:00 – 2:19:00
Product Focus, Counterintuitive Decisions, and Beating Smartwatches
Ahmed explains the counterintuitive product choices that define Whoop—no screen, no watch face, a modular charger, and ignoring steps—and how a narrow focus on health monitoring allowed them to avoid feature bloat. He contrasts this with how success and big budgets often tempt companies into unfocused expansion.
- •Whoop intentionally is not a watch: no time display, no apps, no calls, no Uber on your wrist.
- •Adding a screen invites scope creep (notifications, UI variations, voice, etc.) and distracts from health monitoring.
- •Investment in a modular on-wrist charger was expensive and slow but critical to genuine 24/7 data capture.
- •They deprioritized popular but low-physiology-value metrics like step counts.
- •Ahmed notes that large, successful companies often lose focus when more capital enables them to chase many ideas simultaneously.
- •He emphasizes that real innovation requires 'painful' levels of discipline, saying he still thinks about making Whoop a watch almost daily but resists.
- 2:19:00 – 2:28:00
Invisible Wearables and the Temptation to Do Too Much
Pushing focus further, Ahmed describes Whoop’s move toward 'invisible' wearables embedded in clothing, while Bartlett shares a candid story about canceling an exciting new venture to protect focus. Together they highlight how costly distraction can be and how leaders must actively police their own ambition.
- •Whoop 4.0 sensor can be detached from the wrist strap and embedded in specialized garments (bras, boxers, shirts, sleeves).
- •This 'invisible' approach advances the original first-principles goal: genuine 24/7 wearability.
- •Ahmed jokes about starting as a wearable company and ending up designing underwear—but sees it as a logical extension of the mission.
- •Bartlett recounts stopping a nine-month internal project, including a CEO hire, after realizing it would dilute focus; his team felt relief despite prior excitement.
- •Both agree that success amplifies the temptation to chase adjacent ideas; effective leaders must measure not just upside but the mental and organizational cost of defocus.
- 2:28:00 – 2:37:00
Mission, Subscription Model, and Designing for Retention
Ahmed discusses Whoop’s mission of unlocking human performance and the strategic importance of a subscription model. Instead of optimizing for one-off hardware sales, Whoop has to earn users’ loyalty daily, which shapes product roadmaps and prioritization of features that drive genuine behavior change.
- •Core mission: unlock human performance and improve health through continuous monitoring and insight.
- •Transitioned from one-time hardware sale to subscription; this shifted company DNA toward recurring value delivery.
- •Subscription model forces daily focus on retention, not annual upgrade cycles; every day, users could cancel.
- •Internal product debates now occur 'two or three levels down' within the constraints of mission and subscriber value.
- •Success is defined as behavior change and health improvement, not just devices shipped.
- 2:37:00 – 2:49:00
Competitive Landscape: Nike, Apple, Amazon and the Athlete Strategy
Ahmed recounts launching Whoop into a market crowded with Nike, Adidas, Under Armour, Fitbit, Jawbone, and looming entries from Apple and Microsoft. He explains why he feared Nike most, why he thought their FuelBand strategy was flawed, and how Whoop’s focus on genuine value for elite athletes created an aspirational brand from the top down.
- •Early competitors: Nike FuelBand, Adidas MiCoach, Under Armour’s acquired platforms, Fitbit (IPO), Jawbone (>$1B raised), and rumors of Apple/Microsoft.
- •Ahmed viewed Nike as the biggest threat due to its brand and athlete roster.
- •Critiques Nike’s shortcut: building a mass-market tracker that their own top athletes didn’t wear, breaking their authenticity model.
- •Whoop’s bet: build tech so useful that the world’s best athletes will pay to wear it 24/7; no endorsement needed.
- •Identity strategy: If LeBron, Phelps, and others wear it authentically, health monitoring becomes aspirational, not clinical.
- •Notes that building something worn 24/7 demands genuine value; you can’t pay someone enough to wear an uncomfortable or useless device constantly.
- 2:49:00 – 3:01:00
LeBron, Phelps, Word-of-Mouth, and Product-Led Growth
Ahmed shares the surreal early moment when LeBron James and Michael Phelps became Whoop users, including spotting Whoop on LeBron in a car commercial. Bartlett connects this to broader shifts away from ad-driven sales toward product quality and peer recommendations as the main growth engines.
- •Two of Whoop’s first 100 users were LeBron James and Michael Phelps—a huge validation of product quality.
- •Ahmed recalls seeing LeBron wearing Whoop in a Kia commercial, a moment that impressed even his skeptical parents.
- •For a time, elite athlete adoption helped 'buy time' with investors while business fundamentals caught up.
- •Bartlett notes modern consumer behavior favors genuine endorsements and social proof over traditional ad spend.
- •He describes hearing about Whoop from a friend who praised it so intensely it sounded like a paid ad—illustrating organic evangelism.
- •Ahmed underscores authenticity as core: product must meaningfully improve users’ lives, especially those at the top of their game.
- 3:01:00 – 3:12:00
Choosing Investors, Hating Networking, and Hearing vs. Listening
The discussion turns to investors, boards, and what matters beyond capital, as well as Ahmed’s skepticism about generic 'networking.' He also shares a crucial mindset shift: learning to hear negative feedback without automatically accepting it, transforming disagreement into a tool for sharpening conviction.
- •Investor alignment on mission and use of capital is critical; Ahmed turned down money that came with incompatible strategic expectations.
- •You truly learn who your investors and board are when things go badly, not when times are good.
- •He advocates thorough reference checks and ongoing management of investor relationships during hard periods.
- •Both he and Bartlett dislike unfocused 'networking'; Ahmed prefers relationships formed through shared problems or industries.
- •Mentor’s advice: 'You don’t have to listen to what people say, but you should just hear it.'
- •Earlier in his career, he blocked out negativity entirely as a coping mechanism, which limited learning.
- •Now he treats disagreement as an opportunity to ask, 'How do I know what I know?' and to strengthen or revise his views.
- 3:12:00 – 3:23:00
Customer Insight, Problem vs. Solution, and Being Counterintuitive
Ahmed explains how separating the problems customers describe from the solutions they propose allowed him to conceive Whoop’s focus on recovery and the 'other 20 hours.' He and Bartlett link this to being contrarian, first-principles thinking, and embracing counterintuitive strategies in product and company building.
- •Coaches and athletes asked for more performance tools (GPS, video, stress trackers) but their real issues were injury and availability.
- •Ahmed saw a mismatch between requested features and described pain points; he decided to measure life outside training sessions.
- •Frames this as designing from the problem upward instead of accepting customer-proposed solutions at face value.
- •Notes that 'counterintuitive' decisions—like focusing on sleep and recovery 10 years before it was mainstream—are a recurring theme in Whoop’s story.
- •Stresses the importance of building a process for conviction, pressure-testing it, and then holding firm when it matters.
- •Clarifies he has doubts about many things; conviction is reserved for a small set of deeply reasoned beliefs.
- 3:23:00 – 3:28:00
Personalization, Product Evolution, and Considering Where You Might Be Wrong
Prompted to name something he might be wrong about, Ahmed points to the challenge of serving increasingly diverse user goals with one platform. He suggests that deeper personalization—potentially including which metrics are emphasized—will define the next evolution of Whoop.
- •As Whoop’s user base expanded from elite athletes to enthusiasts to general population, needs diversified.
- •He flags a 'natural tension' between designing for everyone and deeply serving specific goals (weight loss, marathon training, elite sport, better sleep).
- •Believes the product should become more adaptive: goals, content, and even visible metrics may change by user objective.
- •Hints that this is an active area of development rather than a settled answer, illustrating ongoing self-critique.
- 3:28:00 – 3:35:00
Amazon Copycats, David vs. Goliath, and Quiet Confidence
Ahmed tells the story of Amazon exploring an investment and acquisition, learning about Whoop, and later releasing a close copy. Rather than panic, the Whoop team saw it as validation and motivation, expressing their defiance on the internal circuitry of Whoop 4.0.
- •Around 2017–2018, Amazon explored investing in and possibly acquiring Whoop; significant company information was shared.
- •Two years later, Amazon launched a wearable that closely resembled Whoop’s approach.
- •Internally, Whoop treated it as a galvanizing 'David vs. Goliath' moment rather than an existential threat.
- •On Whoop 4.0 circuit boards, they printed: 'Don’t bother copying us. We will win,' plus initials of every engineer involved.
- •Ahmed’s rationale: competitors can only copy what already exists; they can’t see the next wave of innovation rooted in Whoop’s culture and process.
- 3:35:00
Long-Term Vision, Gratitude vs. Drive, and Sprinting the Marathon
Closing the conversation, Ahmed reflects on why he’s more energized now than ever, his long-term vision for health monitoring, and the need to balance gratitude with ambition. He frames success as predicting important health events before you feel them and underscores that appreciating progress does not diminish drive.
- •Unlike some founders who feel they’ve reached the top of their mountain, Ahmed finds the business increasingly exciting as it scales.
- •He frequently sees Whoop devices 'in the wild,' a tangible reminder of impact compared to its origin as an idea on paper.
- •Vision: health monitoring that can accurately predict conditions you can’t feel yet—improving or saving lives.
- •Advice to his younger self: 'Keep going; it will work out,' and learn to balance gratitude with relentless drive.
- •Warns against living solely on a 'dopamine engine' of chasing milestones; it leads to letdowns at each finish line.
- •Insists you can be deeply appreciative of the current moment and still fully committed to the next goal—key to making the journey sustainable over decades.
