YC Valuations, VC Slowdown, and Office Hours with CustomerIQ | E2136
This Week in Startups
Jason Calacanis
4.4 • 1.3K Ratings
🗓️ 10 June 2025
⏱️ 64 minutes
🧾️ Download transcript
Summary
Today’s show: Jason and Alex dive into why Y Combinator startups are raising at sky-high valuations with relatively low ARR—what does that mean for investors and founders? VC funds are slowing down and returning to pre-ZIRP pacing, signaling a reset in the market. Plus, in this week’s Office Hours, Sean Steigerwald, founder of CustomerIQ, demos his AI sales agent that lives in your inbox, drafting follow-ups using CRM context. It’s a deep look at early-stage investing, startup efficiency, and where AI is headed in enterprise.
Timestamps:
(0:00) Episode Teaser(2:09) Jason's Singapore trip recap and SoCal update(9:51) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(11:40) New rumblings from Mistral; is the French AI startup catching a tail wind?(19:40) Fidelity Private Shares℠ - Visit https://fidelityprivateshares.com! Mention our podcast and receive 20% off your first-year paid subscription.(26:23) VC investing pace is slowing... what does this mean for founders(29:42) INBOUND - Use code TWIST10 for 10% o your General Admission ticket at https://www.inbound.com/register (Valid thru 7/31)(33:33) Founders' guide to raising capital(36:31) Gen AI companies are growing FAST but are there concerns about churn?(42:46) Is YC still worth it? Debating paper gains vs. DPI as metrics.(52:18) Office Hours with Sean Steigerald from Customer IQ: managing active users and more.
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Links from episode:
Customer IQ: https://www.getcustomeriq.com/
Follow Alex:
LinkedIn: https://www.linkedin.com/in/alexwilhelm
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LinkedIn: https://www.linkedin.com/in/jasoncalacanis
Thank you to our partners:
(9:51) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST
(19:40) Fidelity Private Shares℠ - Visit https://fidelityprivateshares.com! Mention our podcast and receive 20% off your first-year paid subscription.
(29:42) INBOUND - Use code TWIST10 for 10% o your General Admission ticket at https://www.inbound.com/register (Valid thru 7/31)
Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
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Transcript
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| 0:00.0 | So important data here for entrepreneurs to consider the most important things here are that if you get product market fit early, you're going to be in great shape. |
| 0:11.5 | Because if you get product market fit early, then you need to raise less capital and you own more of the cap table and you spend less time fundraising. |
| 0:19.7 | People who don't have product market fit have to convince people create arguments as |
| 0:25.1 | opposed to just showing their data and saying, talk to my top three customers. |
| 0:28.7 | If your top three customers are over the moon, it's all going to work out. |
| 0:33.8 | This weekend startups is brought to you by Squarespace. |
| 0:37.1 | Turn your idea into a new website. Go to Squarespace. Turn your idea into a new website. |
| 0:39.1 | Go to Squarespace.com slash Twist for a free trial. |
| 0:42.2 | When you're ready to launch, use offer code Twist to save 10% off your first purchase of a website or domain. |
| 0:47.8 | Fidelity Private Shares. |
| 0:49.3 | If you want the all-in-one equity management platform, Fidelity Private Shares has you covered. |
| 0:53.6 | Visit FidelityPrivate shares.com. |
| 0:55.5 | Mention this podcast for 20% off your first year subscription. And Inbound. Connect with visionary |
| 1:02.0 | leaders like Dario Amode and Amy Poehler at Inbound 2025, September 3rd through 5th in San Francisco, |
| 1:08.5 | the epicenter of tech innovation, and transform your business |
| 1:11.1 | strategy for the AI era. Use code Twist 10 for 10% off your general admission ticket at inbound.com |
| 1:16.5 | slash register. Valid through July 31st. All right, everybody, welcome back to this week in startups. |
| 1:21.6 | I'm your host, Jason Kelloggannis with me, my co-host Alex, how are you, Alex? Happy Monday. I'm tremendous. I can't tell you how glad I am to be back at work. |
| 1:29.0 | This was a busy weekend and nothing feels better than focus and time. Oh, very nice, very nice. |
| 1:33.9 | I guess it's been a slow news week, so we'll see if we have anything on the docket that we can get to. |
| 1:38.9 | I'm sure people have a lot of questions for me. Yeah, but first though, Jason, you're in L.A. And so we're coming here an hour later, but you wanted to talk a little bit about |
| 1:46.4 | what you've been up to you with the family, he said. |
... |
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