Evolving Ventures: Reflections from the Capital Frontier

Today’s show:

It’s another All Star Investor Panel! Jason and Alex welcome TrustFund VC founder Sophia Amoruso AND WeekendFund investor/Product Hunt founder Ryan Hoover.Together they’re going DEEP on the current environment for startups, founders, and investors. How do tell durable from brittle revenue… Everyone’s different approaches to follow-on investments and recycling… Strategies on when to trim a position… The benefits of hosting co-working events and jam sessions… And LOTS LOTS more!

It’s an essential watch for anyone building or investing in companies in 2025!

Timestamps:

(0:00) Introducing our amazing investor panel!

(03:15) The panel shares their First Fund experiences

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(11:27) Show cont…

(12:46) Where we’re at on the investor Greed-Fear Index

(13:54) The delicate art of investor discipline

(20:47) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

(21:59) Sophia’s criteria for a follow-on investment

(24:17) Founders are going direct on social media

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(30:49) Show cont…

(32:33) Why we’re seeing so many more Series Bs

(33:30) So when do you trim a position?

(39:35) There are SO MANY COMPANIES! Why surface area matters.

(43:25) Durable vs. brittle revenue and how to tell them apart

(46:15) When it’s time to angel invest outside your fund

(49:04) The panel’s approaches to capital recycling

(57:15) The benefits of co-working “jam sessions”

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