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What happens when you combine running culture, generative AI, and founder-market fit? In this episode of Long Run Labs, we sit down with Jason Kuperberg, co-founder of OtherSide AI and creator of Roast My Strava, to explore how AI can act as a creative partner rather than a replacement. Jason shares how he went from building early generative AI products before ChatGPT to creating playful, highly shareable experiences for the running community. We dig into how founders, marketers, and solo operators can actually use AI day to day, why experimentation matters more than perfect prompts, and how building products for yourself often leads to the strongest traction. We also talk angel investing, distribution, and why small teams can now build software that reaches thousands. This conversation is for anyone curious about AI in the outdoor industry, endurance sports, or creative work, without the hype. 🎧 Full audio episode: https://podlink.com/1820300459 🏃🏻♂️ Follow along with Jon: / jwlevitt Chapters: 00:00 – Why Every Brand Can Become a Software Company 02:30 – Meet Jason: Startups, Running, and Community 04:30 – How Running Became the Thread of His Life 06:30 – Running Culture in NYC Right Now 07:55 – Burnout, PRs, and Stepping Away From Strava 09:30 – Getting Into AI Before ChatGPT Existed 12:00 – Starting an AI Company Before the Hype 13:45 – When AI Became a Cultural Moment 14:55 – The Idea That Became Roast My Strava 15:35 – Building the First Version in the Back of a Car 16:30 – Why Roast My Strava Was Never About Performance 18:00 – AI as a Thought Partner, Not a Replacement 20:00 – A Simple Framework for Using AI at Work 22:00 – Turning Repetitive Tasks Into Leverage 24:40 – Why One AI “Chief of Staff” Works Better Than Many 28:00 – Writing Better by Talking Instead of Typing 33:00 – Asking AI the Questions You’re Afraid to Ask People 37:00 – Founder-Market Fit in the Outdoor Industry 40:30 – How Brands Should Actually Use AI 43:00 – AI-Powered Customer Support That Still Feels Human 45:45 – Building Websites and Products Without Coding Skills 49:30 – Why Small Teams Are Winning Right Now 1:01:00 – Angel Investing and the Power of Distribution 1:05:00 – Finding Deals and Building in Public 1:07:30 – The Future of AI, Creativity, and Community Long Run Labs is a weekly series exploring the intersection of endurance and entrepreneurship from the team that brings you For The Long Run Podcast. From brand builders to movement makers, we spotlight the runners driving change in the outdoor and endurance space. These are the untold stories behind the tools, companies, and communities that shape the industry, told with curiosity, honesty, and heart. Hosted by Jon Levitt. New episodes drop every Tuesday.