This Week in Startups

Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world’s greatest founders, operators, investors, and innovators.

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

Jul 30, 2025 • 74 mins

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!

Key Points

Investors are increasingly considering company valuations and product velocity when deciding on follow-on investments, with a focus on durable revenue and notable lead investors joining the board.
Emerging managers and smaller venture capital funds are seeing a resurgence in LP interest, driven by optimism around AI and the potential for high returns from innovative startups.
The trend of self-directed healthcare and medical tourism is growing, with startups like Doctours facilitating access to affordable elective surgeries and treatments in international locations.

Speakers

Jason Calacanis

Host • 56%

Alex Wilhelm

Host • 7%

Ryan Hoover

Guest • 15%

Sofia Amoruso

Guest • 19%

Partners

Chapters

0:00	The art of disciplined investing and introduction of investor panel
1:11	Sponsor: Squarespace, Lemon.io, Public
3:15	Jason's new fund decision and Sofia's fundraising strategy
5:49	Raising money through poker games and press-VC animosity
8:31	AI's impact on the market, valuations, and trends
10:04	Sponsor: Squarespace
11:27	Market trends, micro funds, and greed cycle in investing
15:05	Valuations, investment strategies, and concentrated investments
20:48	Sponsor: Lemon.io
22:10	Revenue traction, speed of development, and Nectar Social's success
23:39	AI's impact on small teams and new Silicon Valley status symbols
25:01	Social media's role in startup success and challenges of content creation
27:29	Changing signaling and criteria for follow-on investments
29:43	Sponsor: Public.com
30:49	Co-leading investments, board seats, and Series B valuations
33:30	Investment decisions and advice on recycling investments
36:57	Public market strategies and increased startup efficiency
40:46	Rise of no-code/low-code tools and growth of Lovable and AI product sampling
49:05	Recycling fund returns and follow-on investments
53:20	AI startups in Europe vs. the US and founders residency in Majorca
59:54	Community building, support for portfolio companies, and lightning round of news
1:02:35	Sofia Amoruso plugs portfolio companies
1:04:42	Ryan Hoover discusses investment in Atlas
1:06:07	Jason introduces Launch Accelerator startups Autolane and Doctours
1:12:11	Social media handles and Founder University expansion
1:13:34	Episode wrap-up and sign-off

Transcript

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