I Found the Recordings. I'm Grading Myself.
Two podcasts, 2020 and 2022. Seven predictions, one GPA — and the F comes first.
On Wednesday I asked you to guess my GPA. The contract: my worst call on these tapes is now a $10 billion company with its logo on Ferrari’s pit wall. I found the audio of myself making it. Today I grade that call and every other one — no cherry-picking, timestamps attached, so you can check the tape yourself.
Here’s how we got here. Last Friday I wrote about Bessemer’s Anti-Portfolio and repeated the line I’ve taught at Cornell: fake humility is abstract, real humility is specific. That’s an easy thing to admire in someone else’s firm. So I pulled two tapes of my own: The Business Side of Fitness, Episode 15, August 10, 2020, and D&D Fitness Radio, Episode 123, February 13, 2022. Me, on the record, predicting the future of an industry I’d operated in, invested in, and sweated in.
The rules: every call gets the quote, the date, what actually happened, and a letter grade. The grades average into a GPA, like it’s freshman year and I can’t drop the class.
One objection to kill before we start. By February 2022, everybody was bearish on connected fitness — the stock charts had done the arguing, and bear takes were free. Fair. So judge the tape on what wasn’t consensus: calling against the Apple-acquisition rumor the same week it spiked Peloton’s stock 25%. A constructive call — that Strava’s community would turn out to be the whole business. And a Flywheel bet made with real money a year before the crash.
3.29 — That’s the unweighted GPA. Now the work — oldest tape first.
1. Flywheel: the 35 days
The Business Side of Fitness, Ep 15 · August 10, 2020 · 18:11 (min:sec): Flywheel is “tailing down” and “likely to go out of business.”
On September 14, 2020 — exactly 35 days later — Flywheel filed for Chapter 7. Not Chapter 11, where you reorganize and fight another day. Chapter 7. Liquidation. Five weeks from my mouth to the court docket.
And here’s the part that matters more than the sound bite: this wasn’t a hot take I tried on for a podcast. In September 2019 — a full year before that episode — the growth-equity fund I was running made a seven-figure investment premised on exactly the gap Flywheel’s collapse would leave behind. The tape wasn’t a prediction. It was a thesis I already had money behind, said out loud with a date on it.
Grade: A. Vague bearishness is free. “Likely to go out of business,” on the record, costs something.
2. Peloton: the gaps
D&D Fitness Radio, Ep 123 · February 13, 2022 · 32:37: sustaining a company is daily iteration and daily listening — “that’s where Peloton missed... it gave gaps for others to rise up and eat away at that huge lead.”
Housekeeping first, because this one gets misremembered: the host called Peloton a sinking ship that day. Not me. My version was narrower and, I’d argue, more useful — they stopped iterating, and the lead leaked out through the gaps.
When we taped, Foley had resigned five days earlier, with 2,800 layoffs announced in the same breath. That news wasn’t the call. The call was that the erosion wouldn’t stop. It didn’t: two more CEOs since, and a stock that sits around $6 — roughly 96% below its peak.
Honest caveat, because a grade without a caveat is marketing: Peloton posted its first GAAP profit this spring. It isn’t dying. It’s smaller, humbler, and possibly fine. But the call was never “Peloton dies.” The call was “the lead is gone, and it left through the gaps.” That held for four straight years.
Grade: A. Leads don’t get stolen. They leak.
3. Apple: the rumor week
D&D Fitness Radio, Ep 123 · 33:43: “Apple will not acquire them.”
Context is the grade here. The very week we taped, the Wall Street Journal and the Financial Times were reporting Amazon, Nike, and maybe Apple circling Peloton, and the stock spiked about 25% on the story. Saying “no deal” that week meant betting against the market’s mood at its hottest.
Nobody ever bought Peloton. Not Apple, not Amazon, not Nike — nobody, through three CEOs and the whole drawdown. And the kicker I couldn’t have scripted: Peloton’s current CEO, Peter Stern, came over from Apple Fitness+. Apple didn’t buy the company. Peloton bought the Apple guy.
Grade: A. Acquisition rumors are hope with a ticker attached. Ask who’s selling the story.
4. Mirror: the hedge
D&D Fitness Radio, Ep 123 · 35:28: Mirror won’t succeed — there’s no community behind it — and on Lululemon’s acquisition, it “has potential but we don’t know.”
Nineteen and a half months later — September 26, 2023 — Lululemon stopped selling Mirror and signed a deal to get its fitness content from, of all places, Peloton.
My instinct on Mirror was right, and I said it plainly. Then I got to Lululemon and reached for “has potential” instead of finishing the thought.
Grade: B+. A hedge is a prediction you didn’t have the stomach to finish.
5. The celebrity call: wrong name, right thesis
D&D Fitness Radio, Ep 123 · 36:44: celebrity equity can’t substitute for community — and the connected-strength machine LeBron backed wouldn’t matter.
Except: replaying the tape, I caught myself saying “Tempo.” The company LeBron actually backed, in October 2021, was Tonal - which is what I meant. Wrong name, on the record. In a series called Receipts, I eat that one in print.
So grade the thesis against the company he actually backed. Tonal cut 35% of its staff in July 2022. In April 2023 its valuation was cut by roughly two-thirds, and Forbes ran the story under a headline saying athlete investors couldn’t save it. (Footnote: Tempo, the company I actually named, fared no better — no funding round since 2021, gutted by layoffs, still alive but badly diminished. The thesis didn’t care which name I botched.)
Grade: A−. Right thesis, docked a notch for the name — precision is the whole point of a series called ‘Receipts’. Celebrity is reach. Community is retention. They are not the same product.
6. Strava: the marker
D&D Fitness Radio, Ep 123 · 50:44: Apple Watch with Strava showing up on the wrist — the community around it is the marker.
Three months later, Strava announced 100 million athletes. Today it’s past 180 million, was valued at $2.2 billion in May 2025, and this January it filed for an IPO. Filed — not public; I only get credit for what’s actually happened. And one detail I enjoy more than I should: Peloton’s ex-CEO now sits on Strava’s board.
Grade: A. Community wasn’t a feature. It was the business.
7. WHOOP: the F
D&D Fitness Radio, Ep 123 · 45:28: WHOOP is a consumer device, not a high-performance one. And I said it like a ceiling.
My receipts here are personal. In WHOOP’s early days, I had the opportunity to be on a call with the CEO/Founder (Will Ahmed), and he sent me a band, and I wore it for two weeks on my right wrist with an Apple Watch on my left. One boxing class: 1,500-plus calories on the WHOOP, about 700 on the Watch. There is no way I burned 1,500. I wish. And I’m a lifelong swimmer — the strap wouldn’t stay put through an easy swim workout. Case closed, I figured. This is a new Nike Fuel band.
Four years later, here’s the honest read on my own anecdote. No wrist wearable is validated on calorie burn — published error rates run from about 15% to north of 90%, and WHOOP’s own science blog hedges on it. Both devices on my wrist that day were guessing. Optical sensors underwater are a physics problem, not a WHOOP defect. And the thing WHOOP actually stakes its name on — heart rate and HRV during sleep — is validated at about 99%. The device was fine. My frame was wrong on the future.
The business read was worse. I heard “consumer-grade” and treated it as a ceiling. Consumer was the prize: a $10.1 billion Series G this March, around 2.5 million members, a billion-plus in bookings, cash-flow positive. And since January, the logo rides on Ferrari’s Formula 1 cars while the whole team wears the band.
The part I should have seen most, given call #5 above: many of WHOOP’s most visible athletes — Ronaldo, Mahomes, McIlroy, LeBron among them — are compensated partners, ambassadors, or investors, on top of league deals that put a strap on every NFL player. Equity as consumer marketing. The same celebrity playbook that couldn’t save Tonal — run on top of a product people actually keep using. Celebrity can’t replace community. Turns out it can advertise one.
Split verdict, single grade. Right about the device — it is a consumer product, and that’s still true. Wrong about the business, which is the call I actually made.
Grade: F. I graded a company by my own wrist instead of by its market.
Add it up: four A’s, an A−, a B+, and an F. That’s 23 grade points across seven calls — a 3.29. Respectable. Also permanently disfigured by the F, which is about the right amount of humility for anyone in the prediction business.
Because the calls that hit all rhyme. Peloton’s lead leaked into other people’s communities. Mirror had none. Tonal rented celebrity instead of building one. Strava was community, and community turned out to be the entire business. The miss is the same lesson inverted: I judged WHOOP through a community of one — me, my wrist, one boxing class, one swim. Meanwhile the backdrop settled the argument for everybody: a record 81 million Americans belonged to a gym in 2025, while Peloton holds 2.66 million subscribers. People wanted rooms with other people in them. That was the thesis under every call on these tapes, and it was the point all along.
So here’s what happens next. Receipts is now a recurring section of Open Tabs. Every quarter I’ll mark the board to market and re-grade as the facts move — Peloton’s profit already has my pencil hovering over that A. Grades that change aren’t a bug. They’re the entire point of grading in the public eye.
And it’s your turn. Send me the take you’d least like read back to you — reply to this email or drop it in the comments. I’ll grade a batch in a future post, and founding members get theirs graded live in the quarterly AMA.
One more date, since dates are the whole genre: the Charter Window — the first 100 founding seats — closes in seven days, on Friday, July 31. If you’re deciding whether the paid tier is worth it, this essay is the product: judgment, on the record, graded in public, F included.
Open Tab → I dove deeper: both full episodes are embedded above, timestamps and all. Check my math. Then send me yours.
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