Podcast Summary

Invest Like the Best with Patrick O'Shaughnessy

Guest: Tom Digan & Greg Stewart – Building the World’s Best Fitness App (Ladder)

Episode 454 | January 13, 2026

Main Theme

This episode explores the dramatic rise of Ladder, now the top strength training app with nearly $100 million ARR, and over 300,000 paying members. Host Patrick O’Shaughnessy welcomes co-founders Tom Digan and Greg Stewart to dissect the raw, messy, and deeply empirical journey from near failure—complete with debt collectors and pandemic pivots—to category leadership. They discuss customer-obsessed product design, radical transparency, creative approaches to growth (notably via TikTok), the leveraging of AI, scaling pain, and their ambitious vision to become the system of record for health and fitness.

Key Discussion Points & Insights

1. What is Ladder? (06:43)

• Greg Stewart: Ladder is the #1 app for strength training, aiming to emulate the personal trainer experience (programming, coaching, accountability) as accessibly and effectively as possible. Their approach is rooted in engineering, not content-creation.
  • "We just don't look at fitness almost ever. It's not looking at other companies for inspiration." (08:09)

2. Early Struggles & Near-Death (09:40–18:20)

• Tom Digan left a lucrative hedge fund job for what began as a high-conviction side hustle, only to hit wall after wall: operational complexity, lack of product-market fit, near bankruptcy.
  • The first iteration—essentially a managed marketplace—proved operationally unsustainable.
  • Greg Stewart was recruited for his startup acumen: "Greg seemed like the type of guy you wanted to be in a foxhole with." (13:34)
• Funded by friends and family, which intensified personal pressure: "Not sure I'd recommend other people take that path." (17:04)

3. Reset: How Ladder Found Product-Market Fit (18:33–31:34)

• 2020 Pivot: Realized the opportunity was serving fitness enthusiasts (specifically, those struggling with strength training and routine planning), not casual users.
  • Key product insights came from watching user behavior and recognizing the myth of hyper-personalization.
  • Breakthrough MVP: Turned a 1-1 personal training pilot into a group model led by trainers who brought in their own audiences. Instant virality and community among niche groups.
  • "That was magic... there’s community elements and social and they’re happy. And we’d never seen anything like that in the original version of the product.” (29:45)
  • Ruthless focus: "Do the one thing and do it really well, and then do it again." (32:16)

4. Customer-Driven, Empirical Product Development (31:34–38:52)

• Ladder’s “algorithm”: Ruthless prioritization. Only invest in product features that their user data (thousands of App Store reviews, in-depth surveys) proves will increase workout completions—their true North Star.
  • Launched an integrated nutrition tracker only when data showed massive user demand—and deliberately made it free to build trust and data moats.
  • Example: “What we learned was we have a third of our members tracking macros… most are using MyFitnessPal and they hate it.” (33:14)
• Beta testing flows: Only released publicly when >85% were ready to switch.

5. Survival, Fundraising & Salesmanship (21:11–25:53)

• Survival required learning to negotiate creditors (“begging” and “tell them you have no money”—22:02), micro fundraising victories, and selling conviction first.
  • Example fundraising story: “Bill didn’t need to see a deck… He knew you were involved and he was just like, if you’re willing to do this, I need to be involved too.” (25:33)

6. Cracking Growth: The TikTok Cave Process (40:42–51:06)

• Growth bottleneck: Product was working, but growth stalled. TikTok was identified as the unexploited channel.
  • Greg’s “Cave Process”: Self-taught TikTok performance marketing obsessively, learning by direct experimentation—contradicting "industry wisdom" carried over from Facebook/Instagram.
  • "It became a video game… how do we beat the video game today?" (47:41)
  • Key learning: “Own the creative.” In-house creators iterate and learn faster than agencies; job postings for "full-time TikTok creator" were pioneering in 2023.
• The compounding effect: “We took that account from 0 to 250,000 people in 45 days.” (44:56)

7. Marketing Evolution & Empirical Branding (51:09–54:10)

• Expanding from narrow, persona-targeted short-form video to broader brand-building via celebrity, TV, out-of-home. All new tests are kept as tightly measured as possible.
• General Catalyst funding model allows comfortable exploration of less immediately measurable “squishy” brand bets.

8. Why (and How) Consumer Tech is Both Rewarding and Brutal (54:10–57:29)

• Real impact stories are viscerally motivating: “We're changing lives... the feedback loop is fast. But people don't realize in consumer is how freaking hard it is… There are no growth hacks.” (54:40)
• Both product and growth require “black belt” teams. Consumer product success is a long, merciless slog.

9. AI & GLP-1s: Opportunity and Differentiation (57:29–62:24)

• GLP-1 (weight loss drugs) are a macro tailwind: science supports that users must combine with strength training.
• AI applications are everywhere:
  • Used for synthesizing thousands of user feedback entries, writing TikTok hooks, supporting coaches (via the Ladder Pulse tool), and customer support (via proprietary AI ‘Maeve’).
  • “With what’s available to us in AI, we’re able to deliver that personalization as well, which four years ago we couldn’t have.” (58:19)
  • “We've built a customer support tool from scratch… now 90% of the flow… as good or better, and it's faster.” (61:18)

10. Vision, Focus, and the System of Record Ambition (63:02–66:34)

• Fiercely focused product expansion: Only pursue new revenue streams when user demand becomes overwhelming (e.g. waited years to add nutrition, still defer Android).
  • "Are we being dragged into this area by our members? Is it so, so freaking clear…" (63:24)
• Long-term goal: Be the "system of record" for health, fitness, and nutrition—akin to Uber for transport or Spotify for music.
  • Embedded potential: Commerce (supplements, apparel), biomarker tracking, broader user onramps (freemium content).
  • "Our members want us to tell them, 'what supplement do I need?' Those will become businesses for Ladder when there's critical mass." (66:34)
• YouTube, not Peloton, is the real competitor for content: plan to onramp wider audiences starting with free content with motivational mechanics.

11. Capital and the Maturing Investor Journey (69:35–72:22)

• The “siren song” of revenue expansion is resisted unless it’s clearly user-pulled.
• Investor conversations have shifted from desperate cash-raising to highly selective relationship-building, thanks to sound unit economics and the Customer Value Fund financing from General Catalyst.
  • "Now we have some cushion to go be smart. That was not possible [before]." (71:42)

Notable Quotes & Memorable Moments

• On Survival:
  • “Turns out it’s pretty fucking hard.” – Tom Digan (17:14)
• On Customer Obsession:
  • “Our customers... literally tell us what to do.” – Greg Stewart (56:30)
  • “Do the one thing and do it really well, and then do it again.” – Greg Stewart (32:16)
• On TikTok Learning:
  • “All the rules they were telling me were Facebook rules... I realized pretty quickly that everybody is taking this mental model over here and applying it and not trying to figure it out from scratch.” – Greg Stewart (46:18)
• On the Long Game:
  • “This is not go sell the business. This is go build the generational business in consumer…” – Greg Stewart (64:28)
• On Product Focus:
  • “We have no Android app. People think that’s insane… but building an Android app requires pausing development on iOS... for a user that has much lower revenue potential and could absolutely take the business sideways for a year.” – Greg Stewart (63:52)
• On Relentlessness:
  • "You have to just know deep down that you'd be willing to do whatever it takes, including some very difficult conversations with your wife." – Tom Digan (17:05)

Important Timestamps

• 06:43 – What Ladder is, and their unique product philosophy
• 09:40–18:20 – Early company struggles, personal stakes, Tom’s leap
• 18:33–31:34 – Product reset, finding true customer needs, breakthrough MVP
• 31:34–38:52 – Data-driven iteration, nutrition expansion case study
• 21:11–25:53 – Fundraising under duress, conviction-based selling, “Bill” story
• 40:42–51:06 – Cracking TikTok, Greg’s cave process, compounding organic and paid growth
• 51:09–54:10 – Current and next growth frontiers, measuring new media
• 54:10–57:29 – Consumer vs B2B tech, realism about the grind
• 57:29–62:24 – AI’s impact (user feedback, support, coaching), initial thoughts on GLP-1s
• 63:02–66:34 – System of record vision, commerce, and how focus trumps ARPU
• 69:35–72:22 – Evolution of investor relationships and sophistication

Episode Close: Reflections & Gratitude

Kindest thing anyone’s ever done?

• Greg: “It has to be my wife… She’s given me the room to make this possible. If that dynamic wasn’t true, there’s just no way that I could do this.” (72:35)
• Tom: “I’d thank my dad… The three things he taught me about sales: People need to like you, trust you, and you need to be relentless.” (73:08)

Tone & Language

• Direct, candid, and often gritty—emphasizing the “real, dirty” side of entrepreneurship
• Laced with self-deprecation, humor, and honesty about hardship
• Deeply empirical and user-obsessed, both in product development and marketing
• Relentless optimism paired with hard-won wisdom: building consumer products is both “fucking hard” and astoundingly rewarding

For New Listeners

This episode is a masterclass in gritty startup resilience, empirical product design, and consumer business growth. Whether you're an operator, investor, or simply interested in what it really takes to build a breakthrough consumer startup, Digan and Stewart's candor and insight provide a blueprint full of actionable lessons, compelling stories, and raw inspiration.