Tom Digan & Greg Stewart - Building the World’s Best Fitness App - [Invest Like the Best, EP.454] — Summary & Takeaways · Colossus (Invest Like the Best / Business Breakdowns)

This Issue at a Glance

Tom Digan (Co-founder of Ladder, former hedge fund manager) and Greg Stewart (CEO, former investment banker) recount Ladder’s journey from near bankruptcy to becoming the top-grossing fitness app on the App Store (with annualized recurring revenue approaching $100 million and over 300,000 paying subscribers). Core thesis: Ladder’s success does not stem from the size of its content library, but from "making users stop thinking" — scaling the three pillars of personal coaching ("programming, guidance, and accountability") through software engineering, rather than relying on continuously producing more content like its competitors.

Theme 1: From Near Death to Rebirth — Lessons from Ladder 1.0 and the Birth of 2.0

Tom Digan believes that Ladder 1.0 (2017–2020) was a "coach marketplace platform that was operationally complex and difficult to scale," with its fundamental flaw being that "as it scaled, the business increasingly resembled a call center, eventually forcing you to automate the very human service you originally sold."

Historical Context: Ladder initially operated as a marketplace connecting independent coaches with consumers. Tom joined in 2017, on the condition that the company relocate from New York to Austin — "to cut off the safety net." By the end of 2019, the company was on the verge of bankruptcy, lacking product-market fit (PMF) and burdened with heavy debt.
Turning Point: After Christmas 2019, Tom proposed a leadership restructuring to the board, appointing Greg Stewart as CEO. Greg brought a core team — "a group of people who could build anything together, but were at a life stage where they couldn't start from scratch with zero salary."
Mechanism Breakdown: By analyzing the existing business, Greg uncovered two key insights:
The so-called "highly personalized" programming was actually "bucket personas" (e.g., "Sally Pilates"), not truly personalized
The most successful coach, Lauren, attracted clients through Instagram, but "human time is the ceiling" — once she filled all her available time, she could no longer grow
MVP Validation: In February 2020, they had Lauren create group training plans (non-personalized but targeted at specific groups) for her Instagram followers within the existing app. 100 people quickly signed up at $100 per month, with a renewal rate exceeding 90%. "The app looked like garbage, but the promise was delivered."

Greg Stewart added survival strategies from the critical turning point: "We owed hardcore creditors like American Express and learned to negotiate at 20 cents on the dollar."

Core skill: "Make them believe you might actually pay zero — and that it's real."
Daily rhythm: Handle debt negotiations in the morning, build the product in the afternoon, and celebrate small victories at night "like cutting garlic in prison in Goodfellas" — "Raising a $10,000 check had us ecstatic."

Theme 2: Empiricism in Product Building — "Don't Listen to Investors' Product Feedback"

Greg Stewart believes that Ladder's product development algorithm consists of only two rules: "ruthlessly prioritize" and "absorb every bit of information from members" — with the North Star metric being "improving training completion rates."

Mechanism breakdown: The team derives product direction through in-depth research. The launch of the Nutrition feature is a typical case:
One year ago, a 50-minute survey (230 questions) of 5,000 members revealed that one-third tracked macronutrients, of whom 90% used MyFitnessPal and "hated it."
Members' core demand: "I don't want to manage the same problem in two places — output is exercise, input is diet, and this should be a single whole."
The team chose not to charge: "First build trust, earn the right to track, and then data will unlock countless products."
Data chain: Within six weeks of launch, the Nutrition feature recorded nearly 4 million meal logs; the team tracked the metric "how likely are you to switch from your current app" via weekly surveys, which rose from 20% to 85% before deciding to release.
Falsification condition: "Don't listen to any single person's product feedback — everyone has their own use case. When investors say 'you should build this,' we test it, and users say 'no, I don't want that.'"

Tom Digan added discipline on team size: "We have only 30 people (excluding 20 full-time coaches), and AI allows us to avoid expanding the team just to solve problems."

Example: The customer support team consists of just one person (not even full-time), and they built an in-house AI tool, "Maeve AI," which handles 90% of the ticket flow.

Theme 3: Cracking TikTok — "From Zero to 250,000 Followers in 45 Days"

Greg Stewart argues that the core of TikTok's growth engine is not marketing tactics, but "deeply understanding the customer" — they directly translate the customer language deconstructed from App Store reviews into content strategy.

Historical Context: In early 2021, Ladder's ARR was approximately $3-5 million. The product was well-liked by users but lacked a growth engine. Greg chose TikTok as the breakthrough, because "all the eyeballs are there, but the brands haven't arrived yet."
Mechanism Breakdown:
Starting from scratch: Together with creative lead Edsel, they took iPhone video footage from a coach and created a new account under the coach's name.
Learning process: "TikTok is not a social platform; it's a media company. Content must let the algorithm know who to push it to, rather than being created for existing followers."
Key insight: The first viral video (1 million views) took "just two seconds to make." The team deconstructed every frame on a whiteboard — "What is she wearing? What is the first word? What is the background? What is the action?"
Organic growth: From zero to 250,000 followers in 45 days.
Paid Strategy: Greg taught himself to become a TikTok performance marketer, adjusting the budget 7-10 times a day — "People from Facebook told me, 'Don't touch it for two weeks; it's in a learning phase,' but that's Facebook's rule, not TikTok's."
A TikTok employee told him after a meeting: "The approach you are most confident in is exactly what we tell our clients not to do."
Organizational Innovation: In 2023, they hired a "full-time TikTok creator" — "People ask, 'What kind of job is that?' It's like asking what a 'social media manager' was 10 years ago."

Tom Digan added to Greg's "cave process": During the 2021 Texas ice storm, Greg read Crossing the Chasm and produced a 100-slide deck that clarified "who our customer is" — this laid the foundation for the subsequent TikTok strategy.

Theme 4: Long-Term Vision — "The System of Record for Health & Fitness"

Tom Digan believes that no clear category winner has yet emerged in health and fitness, and Ladder aims to become the "system of record" in this space — much like Uber for transportation, Airbnb for short-term rentals, and Spotify for music.

Current positioning: Ladder is the "top app for strength training," but Greg notes that "most people still don't know who Ladder is" — despite being the top-grossing fitness app on the App Store and ranking among the top 100 apps in the U.S.
Product expansion path:
Nutrition features are already live, covering both the "input (diet)" and "output (exercise)" sides
Next steps: supplements, a nutrition marketplace, and biomarker tracking (DEXA scan data)
Long term: expanding from the "paid members who don't want to think" model to a broader fitness audience — "Our competitor isn't Peloton; it's YouTube. People go to YouTube and search for '45-minute upper body dumbbell workout.'"
User expansion: Plans to launch a free tier (content library) to bring earlier-stage fitness users into the Ladder ecosystem, then convert them through the "program" concept — "It's like a puzzle: we give them the picture on the box (the user's vision), then hand them each piece in order. Other products just throw a bunch of random pieces."
GLP-1 impact: Tom sees this as a macro tailwind — "Science supports that you need a strength training program alongside GLP-1, otherwise there's a significant risk of muscle loss." The team has already included questions in its annual survey asking members whether they are using GLP-1.

Greg Stewart emphasizes discipline: "We don't build an Android app because that would require pausing iOS development for a year. We'll do it after we 'win the next level.'"

Funding strategy: Partnering with General Catalyst's customer value fund, which provides monthly financing for growth investments — "The capital markets don't fund CAC (customer acquisition costs) for consumer companies; GC solves that problem."

Mentioned Positions

Position	Analyst Stance	Key Data
Ladder (itself)	Bullish (core discussion target)	ARR approaching $100 million; over 300,000 paying users; only 9,000 paying users in early 2023; top-ranked fitness app by App Store revenue
MyFitnessPal	Risk warning (target being replaced)	90% of Ladder members tracking macronutrients use it but "hate it"
Peloton	Neutral (used as a negative reference)	Once considered an invincible competitor, later faced post-pandemic struggles
YouTube	Risk warning (primary competitor)	"Our biggest competitor is YouTube, not Peloton"
Duolingo	Neutral (used as a positive reference)	Ladder draws on its approach of "using a powerful motivational mechanism to drive a single action"
General Catalyst	Bullish (partner)	Provides financing for Ladder's growth investments through its customer value fund

Judgments Worth Remembering

1. "Don't listen to investors' product feedback" (Greg Stewart) — "Everyone has their own use case. Investors say 'you should build this,' so we test it, and users say 'no, I don't want it.'" Support: Ladder's product roadmap is entirely driven by member surveys and App Store reviews, not investor suggestions.

2. "Our competitor is not Peloton, it's YouTube" (Greg Stewart) — "People go to YouTube to search for '45-minute upper body dumbbell workout.' YouTube wasn't built for fitness, but the content is there." Support: Ladder's paid members "pay to avoid thinking," while the free content library is worth "only $1" to them.

3. "TikTok is not a social platform, it's a media company" (Greg Stewart) — "You have to create content that lets the algorithm know who to push it to, not create for existing followers." Support: Gained 250,000 followers from scratch in 45 days; adjusted ad budgets 7-10 times daily, ignoring Facebook's "two-week learning period" rule.

4. "We owe American Express money, negotiated at 20 cents on the dollar" (Greg Stewart) — "The key is to make them truly believe you might pay zero — and that's real." Support: Early survival strategies included negotiating creditors one by one, Tom tapping into his 401k and personal funds, and convincing friends to buy shares at a 50% discount.

5. "We won't charge for nutrition features — build trust first, earn the right to track" (Greg Stewart) — "Then the data unlocks countless products." Support: 4 million meal records in 6 weeks; only launched after members' willingness to switch from MyFitnessPal rose from 20% to 85%.

6. "We only have 30 people (excluding coaches), AI lets us avoid scaling up" (Tom Digan) — "Customer support is just one person (not even full-time), and we built Maeve AI in-house to handle 90% of the ticket flow." Support: The team includes one full-time AI engineer; nutrition features would have taken 5 years to build without AI.

7. "GLP-1 is a macro tailwind, not a risk" (Tom Digan) — "Science supports that you need a strength training program alongside GLP-1, otherwise there's a significant risk of muscle loss." Support: The team already asks members in annual surveys whether they are using GLP-1 and is considering partnerships with GLP-1 providers.

8. "We won't build an Android app because that would require pausing iOS development for a year" (Greg Stewart) — "We'll do it after 'winning the next level.'" Support: Ladder's prioritization algorithm is "Are members dragging us in this direction? Does it clearly improve workout completion rates?" — otherwise, don't do it.

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

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