![Tom Digan & Greg Stewart - Building the World’s Best Fitness App - [Invest Like the Best, EP.454]](https://image.scripod.com/https://megaphone.imgix.net/podcasts/8459013c-f00c-11f0-ac98-fbad2fe189ee/image/d99352e9439af266dbb87c1efac1299f.jpg?ixlib=rails-4.3.1&max-w=3000&max-h=3000&fit=crop&auto=format,compress)
Tom Digan & Greg Stewart - Building the World’s Best Fitness App - [Invest Like the Best, EP.454]
Tom Digan & Greg Stewart - Building the World’s Best Fitness App - [Invest Like the Best, EP.454]
Tom Digan & Greg Stewart - Building the World’s Best Fitness App - [Invest Like the Best, EP.454]
Building a successful startup is rarely a linear journey, and Ladder's rise from the brink of failure to becoming the top-grossing fitness app reveals the grit, adaptability, and customer obsession required to survive and scale. Co-founder Tom Digan and CEO Greg Stewart share the unfiltered story of how they navigated near-collapse, leadership transitions, and product reinvention to build a company with nearly $100 million in annual recurring revenue.
Ladder’s success was forged through crisis management, starting with a pivotal reset in 2020 when the team negotiated debts, restructured leadership, and launched Ladder 2.0. Early survival hinged on convincing creditors to settle for cents on the dollar and securing small personal investments to demonstrate commitment. The breakthrough came from obsessively listening to customers—analyzing thousands of app reviews and surveying users—which revealed demand for structured, community-based fitness over personalized training. This insight led to rapid product iteration and a viral TikTok growth strategy built on organic content tailored to niche audiences like CrossFit enthusiasts. By hiring full-time creators and institutionalizing creative learning, Ladder scaled its reach without traditional marketing. Today, it’s expanding into nutrition and AI-powered tools like Maeve AI, which handles 90% of customer support, while staying focused on its mission to become the system of record for health and fitness—all driven by real user feedback, not investor whims.
04:28
04:28
Ladder became the top strength-training app with nearly $100M ARR and 300,000+ paying members.
08:32
08:32
Ladder’s success comes from software-first design and listening to members, not copying competitors.
12:12
12:12
Startups are much harder than expected, especially with no money or customers.
16:20
16:20
My wife gave me an ultimatum that became my biggest motivation to succeed.
21:59
21:59
They negotiated debts at 20 cents on the dollar by convincing creditors they might get nothing.
25:23
25:23
Bill invested in the round solely because of the founder's involvement, showing how personal commitment attracts backing.
30:43
30:43
Users bonded over shared frustration with workout planning and cost
31:34
31:34
Do not listen to investors on product feedback; rely on members instead.
37:29
37:29
Nearly 4 million meals were logged in the sixth week after launch.
39:31
39:31
Investor suggestions shouldn't drive product features; user testing should.
42:31
42:31
Greg created a 100-page slide deck after reading 'Crossing the Chasm' during the Texas freeze.
43:57
43:57
Grew TikTok account to 250,000 followers in 45 days without paid promotion
51:15
51:15
Ladder will use celebrity partnerships and TV campaigns to grow beyond short-form video.
56:41
56:41
Customers literally guide the company, as shown by 5,000 responses to the annual survey.
1:00:02
1:00:02
Maeve AI manages 90% of customer support flow
1:02:32
1:02:32
Ridgeline redefines asset management technology, helping firms scale, and the speaker asks about saying no to non-core revenue opportunities.
1:07:23
1:07:23
YouTube is seen as the biggest competitor in fitness content.
1:09:45
1:09:45
Ladder controls the fundraising timeline and can be selective about investors
1:12:35
1:12:35
Be likable, trustworthy, and relentlessly persistent in sales
