How AI Is Changing Running Brands and Why Small Teams Are Winning

Описание: 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.