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

Overview

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

Invest Like the Best with Patrick O'Shaughnessy

1 DAYS AGO
Invest Like the Best with Patrick O'Shaughnessy

Invest Like the Best with Patrick O'Shaughnessy

1 DAYS AGO
OverviewShownoteHighlightsTranscriptChaptersPins

Shownote

My guests today are Tom Digan and Greg Stewart. Tom is the co-founder of Ladder, and Greg is its CEO. Ladder was my first angel investment. What followed over the next seven years is one of the most unlikely and dramatic business stories I’ve been a part ...

Highlights

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.
04:28
Ladder became the top strength-training app with nearly $100M ARR and 300,000+ paying members.
08:32
Ladder’s success comes from software-first design and listening to members, not copying competitors.
12:12
Startups are much harder than expected, especially with no money or customers.
16:20
My wife gave me an ultimatum that became my biggest motivation to succeed.
21:59
They negotiated debts at 20 cents on the dollar by convincing creditors they might get nothing.
25:23
Bill invested in the round solely because of the founder's involvement, showing how personal commitment attracts backing.
30:43
Users bonded over shared frustration with workout planning and cost
31:34
Do not listen to investors on product feedback; rely on members instead.
37:29
Nearly 4 million meals were logged in the sixth week after launch.
39:31
Investor suggestions shouldn't drive product features; user testing should.
42:31
Greg created a 100-page slide deck after reading 'Crossing the Chasm' during the Texas freeze.
43:57
Grew TikTok account to 250,000 followers in 45 days without paid promotion
51:15
Ladder will use celebrity partnerships and TV campaigns to grow beyond short-form video.
56:41
Customers literally guide the company, as shown by 5,000 responses to the annual survey.
1:00:02
Maeve AI manages 90% of customer support flow
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
YouTube is seen as the biggest competitor in fitness content.
1:09:45
Ladder controls the fundraising timeline and can be selective about investors
1:12:35
Be likable, trustworthy, and relentlessly persistent in sales

Chapters

Welcome to Invest Like The Best
00:00
Episode Intro
04:26
Ladder: The #1 Fitness App
05:45
The Messy, Early Years
09:28
Sponsors
14:47
The Darkest Point
16:20
Why Greg Joined Ladder
18:17
The Turning Point: Ladder 2.0
19:45
The Key to Negotiating with Creditors
21:57
Fundraising Challenges and Strategies
23:16
Developing Ladder Teams
25:50
Listen to Your Customers
31:31
Launching Nutrition
32:57
Sponsors
38:53
Don’t Listen to Investors on Product Feedback
39:31
The Cave Process
40:18
Crossing the Chasm
43:13
How to Crack TikTok
43:53
The Content Frontier
51:10
Controlled Bets at Scale
52:07
Why you should Build a B2C Company
54:19
The Impact of AI and GLP-1s
57:37
Sponsors
1:02:32
Staying Focused on the Core Product
1:02:53
Building the System of Record for Health and Fitness
1:05:00
What It’s Like Talking to Investors Now
1:09:45
The Kindest Thing
1:12:32

Transcript

Patrick O'Shaughnessy: Here's an interesting question to think about. If your finance team suddenly had an extra week every month, what would you have them work on? Most CFOs don't know because their finance teams are grinding it out on lost expense report...