VC Roundtable: Recruiting Secrets, Second-Time Founders & Product-Market Fit Myths | E2143
This Week in Startups
Jason Calacanis
4.4 • 1.3K Ratings
🗓️ 26 June 2025
⏱️ 69 minutes
🧾️ Download transcript
Summary
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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Transcript
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| 0:00.0 | Tell me a little bit about secrets to recruiting you've learned the hard way. |
| 0:04.9 | You know, people who look great on paper or, hey, they were at, you know, whatever company, Microsoft, |
| 0:10.2 | Salesforce, whatever, they were selling all the stuff. |
| 0:12.3 | But it had more to do with that company and their product market fit than maybe the grid, right, |
| 0:17.2 | of that individual salesperson. |
| 0:19.5 | And then also, I think, is a really interesting topic of integrating |
| 0:22.1 | people into the team and making them feel that they're part of the team, even though they came |
| 0:27.6 | from the outside. Maybe they weren't part of the formation of the company, but you've got to make |
| 0:31.6 | them feel that they're really part of something. It reminds me of Kevin Durant coming to the |
| 0:36.3 | Warriors, who never quite felt like he was part of the core, right? |
| 0:39.9 | So I had given away my secrets |
| 0:41.7 | on these podcasts. |
| 0:43.4 | I've known you for a long time, Jason. |
| 0:45.9 | For example, when I'm recruiting |
| 0:47.4 | against Google, I say to the candidate |
| 0:51.0 | This weekend |
| 0:53.3 | startups is brought to you by LinkedIn Ads. |
| 0:56.6 | For deem a $100 LinkedIn ad credit and launch your first campaign, go to LinkedIn.com |
| 1:00.8 | slash this weekend startups. |
| 1:03.1 | Notion. |
| 1:04.1 | Notion combines your notes, docs, and projects into one beautifully designed space with AI |
| 1:08.1 | built right in. |
... |
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