Andy Chen is the co-founder of Outcast Ventures, an early-stage fund focused on rethinking how founding teams come together. Prior to Outcast, he worked across recruiting and venture capital, including roles at Riviera Partners, Kleiner Perkins, and Coatue, where he was a General Partner. At Outcast, he’s building a talent-first approach to company creation, including a co-founder matching program designed to help founders form stronger teams from the start.

What you'll learn:

1. Why choosing a co-founder from your existing network can lead to weaker outcomes
2. The data behind why strangers can make better co-founders
3. What actually makes a billion-dollar founding team
4. Why Andy evaluates the team before the idea when investing
5. The key ingredients: skill, interest, and timing alignment
6. Why solo founders rarely build generational companies
7. How AI is enabling a new wave of high-revenue, small-team businesses
8. The evolution of venture capital — and what might come next
9. Andy’s unconventional path into venture, including time in government (as shared in the episode)

In this episode, we cover:

(00:00) Why successful founders struggle to find co-founders

(00:28) Introduction to Andy Chen and Outcast Ventures

(01:17) Andy’s path into Silicon Valley

(03:23) Building Outcast and rethinking founder formation

(04:19) Research on co-founder success (and what most people get wrong)

(06:25) Why working with your co-founder before can hurt outcomes

(07:47) Skill, interest, and timing alignment in founding teams

(08:22) Inside Outcast’s co-founder matching model

(10:24) Why existing co-founder platforms often fall short

(11:23) Talent vs. finance backgrounds in venture capital

(13:37) Why the team matters more than the idea

(14:47) How venture capital has evolved over time

(17:48) Rethinking the “atomic unit” of startups

(19:20) AI, enterprise vs. consumer, and new opportunities

(24:49) The rise (and limits) of solo founders

(27:48) The future of venture in the AI era

(30:33) Rapid fire: trends, feedback, and lessons

(34:20) Andy’s experience working in government

(37:45) Why everyone should try building something