Early Struggles and Leaving Finance

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 of.

Today, Ladder is the number one grossing fitness app in the App Store, approaching $100M in ARR with more than 300,000 paying members. But the path from near death to dominance involved debt collectors, leadership changes, and a full reset during the pandemic.

Tom and Greg built Ladder by being relentlessly empirical about their customers, ruthless about prioritization, raising money wherever they could, and doing whatever it took when most founders would have quit.

We cover the messy early years when survival meant negotiating creditors, how they found PMF by reading thousands of app store reviews, and how they built a TikTok growth engine with no performance marketing experience.

They share their long-term vision for becoming the category winner for health and fitness and the impact of AI and GLP-1s on their business.

This is a conversation about how hard it really is to build something valuable, told by two people who lived through all of it.

For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠

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This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Vanta. Trusted by thousands of businesses, Vanta continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit vanta.com/invest. 

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This episode is brought to you by Rogo. Rogo is an AI-powered platform that automates accounts payable workflows, enabling finance teams to process invoices faster and with greater accuracy. Learn more at Rogo.ai/invest.

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This episode is brought to you by ⁠WorkOS⁠. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. Visit ⁠WorkOS.com⁠ to transform your application into an enterprise-ready solution in minutes, not months.

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This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgelineapps.com.

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Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠).

Timestamps

(00:00:00) Welcome to Invest Like The Best 

(00:04:26) Episode Intro

(00:05:45) Ladder: The #1 Fitness App

(00:09:28) The Messy, Early Years

(00:14:47) Sponsors

(00:16:20) The Darkest Point

(00:18:17) Why Greg Joined Ladder

(00:19:45) The Turning Point: Ladder 2.0

(00:21:57) The Key to Negotiating with Creditors

(00:23:16) Fundraising Challenges and Strategies

(00:25:50) Developing Ladder Teams

(00:31:31) Listen to Your Customers

(00:32:57) Launching Nutrition

(00:38:53) Sponsors

(00:39:31) Don’t Listen to Investors on Product Feedback

(00:40:18) The Cave Process

(00:43:13) Crossing the Chasm

(00:43:53) How to Crack TikTok

(00:51:10) The Content Frontier

(00:52:07) Controlled Bets at Scale

(00:54:19) Why you should Build a B2C Company

(00:57:37) The Impact of AI and GLP-1s

(01:02:32) Sponsors

(01:02:53) Staying Focused on the Core Product

(01:05:00) Building the System of Record for Health and Fitness

(01:09:45) What It’s Like Talking to Investors Now

(01:12:32) The Kindest Thing