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Tom Digan & Greg Stewart - Building the World's Best Fitness App - [Invest Like the Best, EP.454]

2026-01-13 - 77 min - source - Read full transcript

Patrick O'Shaughnessy (host)Tom DiganGreg Stewart

Key insights

Ladder's product design is a direct translation of personal training's three components into software.

Digan and Stewart break personal training into programming (what to do), coaching (expert guidance), and accountability (not wanting to disappoint a coach who's watching), and built the app to approximate all three without requiring a human trainer for every member, since one-on-one coaching doesn't scale economically.

empirical-product-building

The original 'personalized' coaching marketplace was secretly generic, and that discovery reshaped the whole product.

Studying Ladder 1.0's top-earning coach, they found she was actually running a handful of persona-based programs (not truly individualized plans) and was capped by her own available hours; this, combined with a group pilot that hit 90%+ renewal, convinced them the real unlock was good persona-relevant programming plus social accountability, not one-to-one personalization.

empirical-product-building

Product decisions are gated on a single thesis tied to one north-star metric.

Every feature has to make a credible case that it increases workout completions - the company's stated north star, since Ladder is optimizing for members finishing workouts and staying subscribed, not just paying once. This ruthless filter is why the team avoids building 'ten other things just because it's interesting.'

empirical-product-building

No single person, including investors, is treated as the source of truth on product.

Stewart says the team routinely rejects prescriptive investor product advice and instead tests it with members; the nutrition feature came from a 50-minute survey of 5,000 members with a couple hundred questions, all read manually (in the earliest days literally copy-pasted App Store reviews into a Word doc and hand-color-coded by theme) before AI tools existed to synthesize it.

empirical-product-building

Ladder built a TikTok growth engine by owning creative production in-house and ignoring imported Facebook-era rules.

Rather than hiring an agency, Ladder trained its own coaches as creators, iterated on hooks and content format daily, and found that ex-Facebook performance marketers' heuristics (don't touch budgets for two weeks, respect a fixed 'learning phase') actively worked against them on TikTok; Digan changed ad budgets 7-10 times a day against that advice and it worked.

tiktok-organic-growth

Reading Crossing the Chasm during a power outage reframed the whole growth strategy around one beachhead persona.

During the February 2021 Texas grid failure, Stewart read the book and produced a 100-page deck concluding Ladder was trying to be 'all things to all people' during the pandemic's chaotic home-fitness boom; narrowing to a specific customer segment made the subsequent TikTok content and ad strategy dramatically more effective.

tiktok-organic-growth

The first TikTok account went from zero to 250,000 followers in 45 days purely organically, before any paid spend.

Digan and creative lead Edsel started an account from scratch under a coach's name with no existing audience, learned what content worked through rapid trial and error (dissecting wording, setting, hooks), and only began spending on ads three months later once organic traction proved the content model worked.

tiktok-organic-growth

Near-collapse in 2019-2020 was survived through direct creditor negotiation and personal capital, not conventional financing.

Digan negotiated debts (including with American Express) down to roughly 20 cents on the dollar by demonstrating the real alternative was zero recovery, and separately kept the company alive by writing checks from his own 401k and pricing an inside round that friends and family (including a virtual stranger, 'Bill,' who invested sight-unseen out of trust in Digan) filled when no institutional investor would lead.

founder-survival-and-grit

Selling conviction mattered more than selling a finished product during the survival years.

In the depths of the 2019-2020 restructuring, Digan and Stewart were fundraising for a product that didn't yet have visuals or a name; the fundraising skill that worked was demonstrating personal skin in the game (their own money in first) and unwavering conviction that the business would work, not a polished pitch deck.

founder-survival-and-grit

General Catalyst's Customer Value Fund solved the structural problem that consumer companies can't get capital markets to fund customer acquisition.

Digan says no matter how strong Ladder's product metrics were, traditional investors wouldn't fund TikTok ad spend directly; General Catalyst's fund finances that CAC as a repayable facility rather than dilutive equity, which both reduced the cash-flow hit of growth spend and gave Ladder leverage to be selective about which investors join future rounds.

founder-survival-and-grit

AI let Ladder deliver features that would have required years of headcount growth, without expanding the team proportionally.

Stewart says nutrition (Ladder's biggest launch since the original product) shipped in about six months with a 30-person non-coaching team, something impossible two years earlier; internally built tools like Ladder Pulse (which triages coach-chat volume and surfaces unanswered members) and Mave (an AI support tool handling ~90% of ticket volume) let a single support hire and a lean coaching team serve 300,000+ paying members.

ai-as-leverage

Ladder's long-term ambition is to become the 'system of record for health and fitness,' with nutrition as the unlock.

Stewart argues no company has claimed the category-defining position that Uber holds in transportation or Airbnb in short-term housing; nutrition gives Ladder both sides of the calories in/out equation for the first time, which they see as the foundation for future product and user expansion (e.g. supplements, biomarker tracking) once member demand makes each opportunity obvious.

system-of-record-vision

Books referenced

Crossing the Chasm - Geoffrey Moore - Stewart read it during a 2021 Texas winter grid failure and produced a 100-page deck on who Ladder's customer actually was; it reframed their marketing from trying to serve everyone to targeting one specific beachhead persona, which set up the TikTok growth push.

Media referenced

Goodfellas - movie - Digan compares the team's late-night pandemic-era ritual (grilling steaks, smoking cigars, celebrating small wins in an empty office) to the prison scene where mobsters cook elaborate meals behind bars.

Companies

Ladder - Digan and Stewart's strength-training app, the subject of the episode; approaching $100 million ARR with 300,000+ paying members, up from 9,000 paying members at the start of 2023.
Peloton - Cited repeatedly by early investors as an unbeatable incumbent ('how could you possibly compete with a $50 billion company'), then later as a cautionary tale ('Peloton didn't make it') - both used against Ladder's fundraising at different points.
American Express - One of the 'hardcore' creditors Ladder had to negotiate down to roughly 20 cents on the dollar during its near-death restructuring in 2019-2020.
MyFitnessPal - The incumbent macro-tracking app Ladder's members were already using and disliked; Ladder built free tracking specifically to win that trust before layering paid nutrition guidance on top.
TikTok - The platform Ladder used to build an organic-to-paid growth engine from scratch, growing one coach account to 250,000 followers in 45 days without any performance-marketing background.
Meta - Referenced as the incumbent short-form video benchmark (Instagram Reels) that had not yet copied TikTok's format when Ladder started its organic push, and as the source of 'Facebook rules' that Ladder found didn't transfer to TikTok's algorithm.
General Catalyst - Its Customer Value Fund now finances Ladder's TikTok customer-acquisition spend on a repayment-over-time basis, solving what Digan calls capital markets' unwillingness to fund CAC in consumer companies directly.
YouTube - Named as Ladder's real biggest competitor (not Peloton), since free, high-quality fitness content already lives there; Ladder's long-term plan is a free content on-ramp that mirrors YouTube's consumption pattern.
Uber - Used as the category-winner analogy (transportation) for the 'system of record' position Ladder wants to hold in health and fitness.
Airbnb - Used alongside Uber and Spotify as an example of an undisputed category winner, contrasted with health and fitness having no equivalent yet.
Positive Sum - Patrick O'Shaughnessy's investment firm, disclosed at the top of the episode; Ladder was his first-ever angel investment.
Colossus - Patrick O'Shaughnessy's quarterly publication and podcast network, referenced in the episode's outro.

Techniques and frameworks

Programming, coaching, accountability framework - Ladder's founding product thesis: personal training works because it delivers programming (what to do), coaching (expert guidance), and accountability (a coach you don't want to disappoint); the app was designed to approximate all three in software.
Ruthless, north-star-gated prioritization - Every feature has to pass a single test - does it plausibly increase workout completions, the company's north-star metric - rather than being built because it's interesting or easy; this is credited as one of only two things (alongside growth) that made the business durable.
Push vs. pull for new product bets - Stewart and Digan only greenlight major new product lines (e.g. nutrition) when members are visibly 'pulling' them into it through survey and support signals, rather than the founders pushing a hunch; nutrition sat on the roadmap for five years before member demand made it obvious.
Cave process - Stewart's pattern of disappearing into deep, self-directed research when a new bottleneck appears (cracking the TikTok algorithm, reading Crossing the Chasm during a power outage) and returning with a concrete operating plan, rather than delegating the problem or hiring it out immediately.
Customer Value Fund financing - General Catalyst's structure for financing Ladder's paid customer acquisition as a repayable-over-time facility rather than dilutive equity, addressing the pattern where 'capital markets aren't funding CAC in consumer companies' no matter how strong the product is.

Summary

Tom Digan and Greg Stewart, co-founder and CEO of the strength-training app Ladder, walk Patrick O'Shaughnessy (Ladder's first-ever angel investor) through the company's full arc: from a near-collapse in 2019-2020, through a pandemic-era product reset, to a TikTok-driven growth engine that took the business from roughly 9,000 paying members at the start of 2023 to over 300,000 members and nearly $100 million in ARR today. The conversation is unusually candid about the mechanics of survival - negotiating creditors like American Express down to 20 cents on the dollar, funding payroll from Digan's own 401k, and closing a bridge round with a friend-of-a-friend who invested "sight unseen" out of trust rather than diligence.

The middle of the episode is a case study in empirical, member-driven product building. Studying Ladder 1.0's marketplace of independent coaches, the founders discovered the "personalization" customers were paying for was actually generic persona-based programming, and that a group pilot with a top coach - built by "jimmy-rigging" the existing app to let multiple members share one coach and a chat thread - produced 90%+ renewal and unexpected in-person community formation. That became the seed of Ladder 2.0: relentless, non-personalized but persona-relevant programming, paired with social accountability, gated at every step by whether a feature plausibly increases workout completions, the company's stated north star. The same discipline shows up in how they built nutrition, Ladder's biggest launch since the original product: a 5,000-response member survey, hundreds of questions read line by line, and a conscious decision to give basic macro tracking away for free to win trust away from MyFitnessPal before charging for prescriptive guidance.

Stewart describes a recurring "cave process" where he disappears into deep, self-directed research when a bottleneck appears - most notably reading Crossing the Chasm during a February 2021 Texas grid failure, which reframed a scattershot "we're weights, we're bodyweight, we're gym, we're home" pitch into a focus on one specific beachhead customer. That focus underpinned Ladder's TikTok growth engine, which the team built from zero with no performance-marketing background: taking a single coach's account from zero to 250,000 followers in 45 days organically, then learning that imported Facebook-era ad heuristics (fixed learning phases, hands-off budgets) actively worked against them on TikTok's different algorithm. They insisted on owning creative production in-house rather than outsourcing to an agency, since the iteration cycle needed to be fast enough to compound learnings daily.

On financing, Digan traces a shift from desperate, no-selectivity fundraising in the early years (when Peloton's scale was used against Ladder as evidence it couldn't compete, and later Peloton's decline was used as evidence consumer fitness apps don't work) to a General Catalyst Customer Value Fund deal that finances TikTok customer acquisition on a repayable basis rather than dilutive equity - a structural fix, Digan argues, for capital markets' broader unwillingness to fund CAC in consumer companies directly. That leverage now lets Ladder build investor relationships outside the pressure of an active raise.

On AI, both founders describe two distinct chapters: first as a synthesis tool for processing thousands of survey responses and app store reviews (work that used to be done by hand, literally color-coding Word documents), and now as embedded product infrastructure - Ladder Pulse triages incoming coach-chat volume and surfaces unanswered members, while an internally built support tool called Mave handles roughly 90% of ticket volume with a single support hire. Stewart is explicit that the goal is augmenting the coach relationship, not replacing it, since human accountability remains central to the product. The episode closes on Ladder's long-term ambition to become the "system of record for health and fitness," positioned as the category's missing Uber-or-Airbnb-style winner, with nutrition unlocking both sides of the calories in/out equation and YouTube, not Peloton, identified as the real long-term competitor for consumer attention.

Notable Quotes

"Turns out it's pretty fucking hard. I think that dynamic is why Ladder's here." - Tom Digan

"There's no quick fixes. Growth hacks are not a real thing. You have to be black belt at building products for the consumer and growth." - Greg Stewart

"I would challenge someone to try to build the experience that we've built using AI... we're going to continue to lean into things AI can't touch, which is we've built a compelling brand." - Tom Digan

"Great product, no growth, doesn't work, doesn't get funded. Great growth engine, no product, leaky bucket, doesn't become a big company. Both those things have to be true to be able to build a company that's durable and last." - Greg Stewart

"Investors come in and say, who's your biggest competitor? Is it Peloton? It's like, no, it's YouTube. By far. It's not even close." - Greg Stewart