All Star Investor Panel! Sophia Amoruso and Ryan Hoover | E2158

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

(10:03) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST

(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

(29:35) Public - Take your investing to the next level with Public. Build a multi-asset portfolio and earn 4.1% APY on your cash—with no fees or minimums. Start now at public.com/twist.

(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”

Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com

Check out the TWIST500: https://www.twist500.com

Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp

Follow Lon:

X: https://x.com/lons

Follow Alex:

X: https://x.com/alex

LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm

Follow Jason:

X: https://twitter.com/Jason

LinkedIn: https://www.linkedin.com/in/jasoncalacanis

Thank you to our partners:

(10:03) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST

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

(29:35) Public - Take your investing to the next level with Public. Build a multi-asset portfolio and earn 4.1% APY on your cash—with no fees or minimums. Start now at public.com/twist.

DISCLAIMER

*All investing involves the risk of loss, including loss of principal. Brokerage services for US-listed, registered securities, options and bonds in a self-directed account are offered by Public Investing, Inc., member FINRA & SIPC. Public Investing offers a High-Yield Cash Account where funds from this account are automatically deposited into partner banks where they earn interest and are eligible for FDIC insurance; Public Investing is not a bank. Cryptocurrency trading services are offered by Bakkt Crypto Solutions, LLC (NMLS ID 1890144), which is licensed to engage in virtual currency business activity by the NYSDFS. Cryptocurrency is highly speculative, involves a high degree of risk, and has the potential for loss of the entire amount of an investment. Cryptocurrency holdings are not protected by the FDIC or SIPC.Alpha is an experimental AI tool powered by GPT-4. Its output may be inaccurate and is not investment advice. Public makes no guarantees about its accuracy or reliability—verify independently before use.Rate as of 7/18/25. APY is variable and subject to change.

Check out Jason’s suite of newsletters: https://substack.com/@calacanis

Follow TWiST:

Twitter: https://twitter.com/TWiStartups

YouTube: https://www.youtube.com/thisweekin

Instagram: https://www.instagram.com/thisweekinstartups