FEATURED STORY
WHOOP vs. Google's Sports Wearables War
WHOOP vs. Google Fitbit Air: who wins?
For those who opted to take a social media cleanse this past week, here’s the recap.
Google unveiled its new Fitbit Air, a screenless wearable that tracks essential health data 24/7 (e.g., heart rate, blood oxygen), monitors sleep and exercise, and connects to Google Health Coach – a Gemini AI-powered all-in-one fitness trainer.
Oh, and it seamlessly fits on your wrist.
Basically another WHOOP.
The immediate reaction from the public was that WHOOP, a now $10B company after its $575M Series G, was in serious trouble. Why? The Fitbit Air is a $100 one-time purchase + $10/month opt-in for Google Health AI coach versus WHOOP’s $200-300/year subscription.
Two examples of cases made against WHOOP came from Rjey – a popular tech reviewer on YouTube – and Nicole DeTommaso, a VC investor at Harlem Capital:
To summarize, they believe WHOOP will lose because Google's Fitbit Air is way cheaper and its Gemini-integration will provide a far superior health-tracking tool than WHOOP’s.
A bit reductionist.
While the overall sentiment felt “doom-ish” for the 14-year old smartband, there were a few of us who believe that beating WHOOP will be way more difficult than you’d think – even for a juggernaut like Google.
Even if Google Fitbit Air is a better product.
WHOOP has ingrained itself in the sports ecosystem through strategic partnerships with teams, leagues, and athletes. This is a MOAT that Google can’t replicate overnight.
In this newsletter, we’ll break down how WHOOP leverages athletes and professional sports partnerships as a powerful moat against competitors, how the battle between WHOOP and Google will be fought in sports, and what’s to come next.
How WHOOP Built Allegiance with Superstar Athletes
Before releasing its product to the general public in 2016, WHOOP’s team spent a year rigorously testing its smartband with elite athletes through their personal trainers.
They battle-tested and iterated the product by embedding WHOOP in training, finding a significant boost in overall performance from the band’s insights.
From their 2016 announcement, they shared that they worked with:
Olympians Ryan Lochte, Adeline Gray, Case Patterson, Jake Gibb, and many more
Cleveland Cavs Assistant Trainer Mike Mancias, who was helping train LeBron James at the time, and USA Swimming National Team Athletic Trainer Keenan Robinson
Military and collegiate athletes
“Well, this is the key to getting to a world class athlete back then was going to their personal trainer, that's still a pretty good person to go to today… And those personal trainers spent more time with these athletes than, you know, almost anyone else.” – WHOOP CEO Will Ahmed
After its release, WHOOP built a cult following from the global professional athlete community, who turned out to be some of the brand’s most powerful ambassadors: Lebron James, Cristiano Ronaldo, Michael Phelps, Rory McIlroy.
They inadvertently became the brand’s strongest marketers by wearing WHOOP in public despite not having official sponsorships.
For example, in this year’s Australian Open, both Carlos Alcaraz and Jannik Sinner pushed back against the Open when they were asked to remove their WHOOPs during tournament play, citing personal reasons.
That’s the best advertisement a smart wearable can get.
And now, some of the greatest athletes in the world are investors in the company:
Sources: WHOOP press releases and investor disclosures, Series E (Oct 2020) and Series G (Mar 2026). Major athletes also took part in WHOOP’s Series F in 2021.
Athletes 🤝 WHOOP. WHOOP 🤝 Athletes.
As WHOOP rapidly scales to the every-day customer, they are leaning more into sports as a core differentiator.
Just this week, WHOOP announced it will be the Official Health and Fitness Wearable for the Boston Red Sox from 2026-2028.
That’s one of many partnerships it has made with professional teams and leagues in just the last few months:
Sources: WHOOP press releases and partnership disclosures, 2017-2026
Elite Sports 🤝 WHOOP. WHOOP 🤝 Elite Sports.
WHOOP establishing itself as the athlete-first health tracker ultimately became its distinguishing quality in the market as a premium product.
“If the best of the best use it, so should I.”
Status from proximity to elite performance.
It lapsed the Nike Fuel Band, which predated WHOOP by 4 years.
It then beat out the Halo, Amazon’s competing screenless wearable, which sold at a much cheaper price point ($65-99 one-time purchase + $4/month subscription). Halo shut down less than 3 years after launch, despite only having a very marginal difference in utility.
In the battle of wearables, brand status is essential.
Where Google Fitbit Air Might Push Into Sports
To reinforce this point, a core component to Google Fitbit Air’s May 26th release is announcing Steph Curry, the greatest shooter of all time, as the product’s primary ambassador.
Not only was he deeply involved in the development of Google Health Coach, but Google is also launching a special edition Fitbit Air designed by him.
Steph Curry was a perfect but obvious choice.
Google has been the NBA’s official search and fan insights partners, while Pixel is the official fan phone. Google is also a Founding Partner of Chase Center, and Google Cloud is the official public cloud provider of the Warriors.
Given their deep connection with the NBA, it makes sense that Google would take from WHOOP’s playbook and push to become the official and/or exclusive wearables partner of the league. However, the NBA CBA explicitly prohibits devices from being used in games under Article XXII Section 13 – and any exceptions would be governed by a six-person Wearables Committee – three players and three representatives from the NBA league office.
It could be a tall order to get the players association to allow only one device to be used, especially if that device is actively hurting the valuation of some players’ personal investments.
But Google currently has many player ambassadors that could be prime candidates to champion the FitBit air – superstars like Luka Doncic, Giannis Antetokounmpo, SGA, and more.
Outside of the NBA, they may look to activate wearables sponsorships from existing partnerships with sports properties… or the players on those teams:
Source: Google partnership disclosures and league press releases, 2026.
Even as Google Fitbit Air leverages premier athletes and potentially sports properties for brand building and distribution, WHOOP feels far ahead as an established “premium” due to how entrenched it already is within the industry.
But, instead of one replacing or beating the other – like everyone on X thinks will happen – we believe these two products will just inevitably coexist.
Like the Swiss vs. Japanese watches in the 70’s.
The Brand Age, But for Wearables
Y Combinator founder Paul Graham recently wrote a powerful article on why technology is entering the brand age – using luxury watches in the ’70s as the perfect case study.
Japanese watches put many Swiss watchmakers out of business because they were better timekeeping products. But as Graham wrote, “a handful survived as independent companies” by “transforming themselves from precision instrument makers into luxury brands.”
WHOOP is the Swiss watch.
It is asserting its status by aligning itself with the most premium sports properties and the greatest athletes in the world. And it has even leaned further into customization and accessories to embolden the display – just look at its cashmere bands, where the band itself, not the subscription, sells for $177 retail.
Google Fitbit Air is the new Japanese watch – potentially a better health tracker, one whose luxury status is still waiting to be proven.
So, to the sports partnerships divisions and athlete agents reading this:
Wait on standby.
WHOOP and Google will be calling.
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LEAGUES & TEAMS
Photo: Seattle Kraken’s owner Samantha Holloway is looking to place a bid for a Seattle NBA expansion bid.
Kraken’s Owner Samantha Holloway hires JPMorgan and Moelis to advise Seattle NBA expansion bid as league process advances (May 6th)
Holloway’s One Roof Sports and Entertainment group is currently the only publicly known ownership group pursuing an NBA expansion franchise in Seattle
NBA expansion fees are expected to exceed $8B total, with Seattle and Las Vegas viewed as the league’s leading candidates for new franchises beginning as early as the 2028-29 season [Seattle Times]
NBA plans to invest $3B into NBA Europe to support launch economics and franchise stability (May 7th)
NBA told prospective investors it will help absorb early operating losses, fund launch marketing, and provide participation payments to teams as the league ramps up toward a planned 2027 debut [SBJ]
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STARTUPS & VENTURE CAPITAL
Photo: Enhanced Games, a new PED-friendly league, to debut at Resorts World Las Vegas on May 24th.
Wisdom Ventures closes an oversubscribed $77.7M Fund II focused on AI-powered health, wellness & connection startups (May. 12th)
Includes $1M–$5M checks into ~40 startups across AI implementation in health, wellness, and connection
LPs include Reid Hoffman, Evan Sharp & Stewart Butterfield; Fund I backed OpenAI, Anthropic & Function Health [Athletech]
Outside Capital launches to invest in startups across sports, performance, and consumer wellness (May 12th)
Founded Tom Black and Parth Dalal (formerly at Imaginary Ventures), who plan to back early-stage brands operating across sports, human performance, and wellness [LinkedIn]
Enhanced Games expands beyond “Steroid Olympics” positioning into supplements, telehealth, and longevity business strategy ahead of debut event (May 11th)
Enhanced Games debuts May 24 in Las Vegas, allowing athletes to compete using certain FDA-approved performance-enhancing substances under medical supervision
Expanding into supplements, recovery products, and telehealth as it builds a broader human performance and longevity platform [FOS]
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M&A AND INVESTMENTS
Photo: Sports PE-fund Bruin Capital acquires Matchroom Boxing at a $1.35B valuation.
Bruin Capital buys stake in sports promoter Matchroom Boxing, valuation reaches $1.35B (May 11th)
Bought a 15% stake from the Hearn family at a valuation of $1.35B
Produces more than 600 events and 2,400 hours of programming annually including boxing events, darts competitions, and the World Snooker Tour [Sportico]
University of Michigan could see massive NIL implications from early OpenAI investment now reportedly valued near $2B (May 8th)
Michigan reportedly invested $20M into OpenAI through its endowment years ago, with recent court documents implying the stake could now be worth billions on paper
Reports suggest the windfall could eventually supercharge Michigan athletics and NIL spending [EssentiallySports]
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STRATEGIC VENTURES
Photo: Kalshi becomes the Official Prediction Market Partner of Madison Square Garden.
Kalshi signs multi-year partnership with Madison Square Garden, renaming MSG’s sixth-floor concourse the “Kalshi Concourse” (May 8th)
Deal makes Kalshi an Official Prediction Market Partner of Madison Square Garden and includes arena signage, fan activations, marquee placements, and integrations across MSG Networks [Kalshi]
FOX Sports and Cosm partner to bring 40 FIFA World Cup 2026 matches to immersive dome venues (May 8th)
Cosm will broadcast select World Cup matches across its Los Angeles, Dallas, and Atlanta venues using its 87-foot 12K LED dome technology to recreate stadium-like viewing experiences [FOX Sports]
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JOB BOARD
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Now - here are some cool roles we found and personally curated this week. Enjoy!