This week, I chat with Jon Staenberg founding partner of Agate Hound Fund, to unpack the real mechanics behind venture capital and search funds. From his early days at Microsoft, to founding a search fund that delivers 35% net annual returns, Jon pulls no punches. He warns, “Don’t go into venture until you’ve actually got a skill,” and breaks down the challenges of buying a company. We explore how grit, curiosity, and critical thinking separate founders who retire early from those who build enduring empires, and why the “comprehensiveness of change today is astonishing.”
Whether you’re curious about launching a search fund, leveling up in VC, or simply hungry for insights, this episode will equip you with the tools and the mindset to raise your game.
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We explore:
0:00 – Intro & Meet Jon Staenberg of Agate Hound Fund
4:50 – “Microsoft was way beyond my expectations…”
10:30 – “Don’t go into venture until you’ve actually got a skill”
16:15 – Search Funds 101: “5% net annual return
22:00 – “Buying a company is hard… it’s messy”
28:05 – Why grit, curiosity & critical thinking win
33:40 – The “retire early” myth vs. 60‑hour workweeks
38:20 – AI & the comprehensiveness of change today
42:10 – How to connect with Jon
ABOUT JON STAENBERG
Jon Staenberg is the founding partner of Agate Hound Fund, a search‑fund vehicle focused on acquiring and scaling founder‑owned companies. Before launching Agate Hound, Jon spent over a decade at Microsoft, where he led product strategy and saw firsthand how engagement and inspiration fuel innovation. A veteran operator turned investor, he’s passionate about teaching entrepreneurs that “buying a company is hard,” but also demonstrating how a disciplined, skill‑based approach can generate 35% net annual returns. Jon holds an MBA from Stanford and advises several high‑growth startups on go‑to‑market and capital strategy.
Get in touch with Jon:
Website: https://www.agatehound.fund/
Email: jon@agatehound.fund
ABOUT JASON
Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.
You can reach out to Jason through:
Email: jason@thunder.vc
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