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Home > This Week in Startups > VC Roundtable: Recruiting Secrets, Second-Time Founders & Product-Market Fit Myths | E2143
Podcast: This Week in Startups
Episode:

VC Roundtable: Recruiting Secrets, Second-Time Founders & Product-Market Fit Myths | E2143
Category: Technology
Duration: 01:08:51
Publish Date: 2025-06-26 00:05:40
Description:

Today’s show:

In this powerhouse VC roundtable, @Jason sits down with Sequoia’s Doug Leone and Cyberstarts’ Gili Raanan to share brutally honest insights on startup recruiting, evaluating second-time founders, and how to truly find product-market fit. They break down why big-tech résumés can be misleading, how to structure early teams, and what separates “missionary” talent from mercenaries. Plus, the myth of early ARR, the art of founder-board trust, and how AI is (and isn’t) reshaping startup velocity. Must-watch for founders, VCs, and anyone building from 0 to 1.


Timestamps:

(03:25) The origins of Wiz and how VCs know when to invest

(05:17) What qualities are investors looking for in founders and entrepreneurs?

(09:53) LinkedIn Ads - Get a $100 LinkedIn ad credit at http://www.linkedin.com/thisweekinstartups

(18:40) How to know when you’ve reached true Product Market Fit: the experts sound off

(19:20) Notion - Try it for free today at https://notion.com/twist

(25:39) The secrets of recruiting top talent

(29:54) CLA - Get started with CLA's CPAs, consultants, and wealth advisors now at https://claconnect.com/tech

(39:38) Judging a startup’s revenue quality and “founder vs. salesman” deals

(53:38) Is venture capital kind of a SCAM?

(55:00) Seed Investing: “Pick them right and early”


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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:

(09:53) LinkedIn Ads - Get a $100 LinkedIn ad credit at http://www.linkedin.com/thisweekinstartups

(19:20) Notion - Try it for free today at https://notion.com/twist(29:54) CLA - Get started with CLA's CPAs, consultants, and wealth advisors now at https://claconnect.com/tech


Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland


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


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Twitter: https://twitter.com/TWiStartups

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

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

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Substack: https://twistartups.substack.com


Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916
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