Y Combinator, Open Source, and Lifting Founders Up with Jason Freedman

Jason Freedman is a serial founder and General Partner at Orange Collective. Orange Collective is a Y Combinator-focused venture fund that aims to invest in the most promising YC companies before Demo Day. We talked about YC, exits, AI, open source, raising founders up, and why ownership percentages are overrated.

The episode is now available on Apple Podcasts, Spotify, Amazon, and YouTube Music.

Y Combinator, Open Source, and Lifting Founders Up with Jason Freedman

00:00 The Journey of a Founder

05:56 The Importance of Honest Feedback

09:08 Understanding Founder-Investor Dynamics

13:36 Navigating the M&A Landscape

24:48 The Focus on AI Investing

33:22 The Role of Open Source in Business Models

38:57 Challenging Ownership Percentage Norms

Insights from Y Combinator, Open Source, and Lifting Founders Up with Jason Freedman

• PG’s 90-second rescue — At his lowest point, a phone call from Paul Graham (“What’s something that annoys you about the world?”) pivoted Freedman toward office-search startup 42Floors; the entire pep-talk took 90 seconds and dictated the next decade of his life

• Advice inflation — Founders routinely over-index the wisdom of investors simply because those investors wrote a check, letting capital trump customer insight and living to regret it

• Era-bound pattern matching — Investors’ playbooks mirror the market vintage that made them rich (SEO age, blitz-scaling era, profits-only, etc.), so “proven” advice can misfire in a new paradigm

• AI-stack focus as deal magnet — Branding Orange Collective as an AI-infrastructure fund pulls in frontier builders (even OpenAI engineers) and enables portfolio companies to trade deep technical know-how across the stack

• Open-source hedge against platform risk — Backing open-source alternatives lets startups survive if closed-source giants absorb their feature set; history shows the long arc of “closed beats open early, open wins big later”

• Constraints sharpen judgment — A narrow mandate (YC + AI) helps the team dodge distraction and gives LPs clean exposure, proving that “constraints make us better”

• Ownership-minimum dogma kills returns — Rigid “we need 8-25 %” rules have cost legendary seed investors billions, while broad, small-cheque indexing (SV Angel, Liquid, etc.) has outperformed on TVPI/DPI

• Brutal honesty, zero teardown — YC’s core ethic is “be candid and build people up”; Freedman credits PG’s unsentimental yet uplifting feedback style and tries to replicate it in his own mentoring

The content here is for informational purposes only and should not be construed as investment, legal or tax advice. The opinions expressed by guests are their own and do not reflect the views of Seaplane Ventures. Our host, guests and clients may hold investments discussed in this podcast. Please invest responsibly.