{"podcast":{"title":"Invest Like the Best with Patrick O'Shaughnessy","slug":"invest-like-the-best","podcast_index_feed_id":982387,"rss_url":"https://feeds.megaphone.fm/CLS2859450455","website_url":"https://colossus.com/","image_url":"https://megaphone.imgix.net/podcasts/ef669774-cccd-11ed-889b-c36caad6646f/image/158efdddfb983d2678b3530d484e8aa2.jpg?ixlib=rails-4.3.1&max-w=3000&max-h=3000&fit=crop&auto=format,compress","author":"Colossus","episode_count":577,"summary":"Conversations with the best investors and business leaders in the world. We explore their ideas, methods, and stories to help you better invest your time and money. Hear stock market and boardroom insights you can't find anywhere else. If you're a professional investor, CEO, entrepreneur, or business strategist, this is for you. Explore all our episodes and learn more at https://www.colossus.com","last_synced_at":null,"page_url":"https://stenobird.com/podcast/invest-like-the-best"},"episode":{"title":"Tom Digan & Greg Stewart - Building the World’s Best Fitness App - [Invest Like the Best, EP.454]","slug":"tom-digan-greg-stewart-building-the-world-s-best-fitness-app-invest-like-the-best-ep-454","published_at":"2026-01-13T09:00:00+00:00","page_url":"https://stenobird.com/podcast/invest-like-the-best/tom-digan-greg-stewart-building-the-world-s-best-fitness-app-invest-like-the-best-ep-454","show_page_url":"https://stenobird.com/podcast/invest-like-the-best","url":"https://colossus.com/episode/building-the-worlds-best-fitness-app","audio_url":"https://traffic.megaphone.fm/CLS1415175202.mp3?updated=1768269876","summary":"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.⁠⁠⁠⁠⁠⁠⁠⁠ ----- ⁠Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠ to sign up for free and get a $250 welcome bonus. ----- ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Vanta is trusted by thousands of businesses and continuously monitors your security posture and streamlines audits so you can win enterprise deals and build cus…","meta_description":"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…","key_points":[],"chapters":[],"topics":[],"duration_seconds":4448,"processing_state":"failed","actions":[{"name":"request_transcript","method":"POST","url":"https://stenobird.com/v1/public/podcasts/invest-like-the-best/episodes/tom-digan-greg-stewart-building-the-world-s-best-fitness-app-invest-like-the-best-ep-454/transcription-requests","description":"Idempotently request low-priority transcript generation for this episode."},{"name":"read_markdown","method":"GET","url":"https://stenobird.com/podcast/invest-like-the-best/tom-digan-greg-stewart-building-the-world-s-best-fitness-app-invest-like-the-best-ep-454.md","description":"Read the agent-friendly Markdown representation of this episode resource."}]}}