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Startups For the Rest of Us

Episode 792 | Hot Take Tuesday: GPT-5 Struggles, the A.I. Bubble, and the Windsurf Debacle

Startups For the Rest of Us

Rob Walling

Entrepreneurship, Management, Business, Marketing

4.9819 Ratings

🗓️ 2 September 2025

⏱️ 46 minutes

🧾️ Download transcript

Summary

Is GPT-5 a real risk for SaaS founders, or just the beginning of a new chapter? In this Hot Take Tuesday, Rob Walling, Einar Vollset, and Tracy Osborn dig into GPT-5’s mixed reviews, signs of stress in the A.I. bubble, and how Windsurf’s $2.4B exit left early employees with nothing. They also unpack why returning a VC fund is such a rare (and big) deal. Episode Sponsor This episode is brought to you by Gearheart.io, which specializes in helping early-stage founders validate ideas, prototype SaaS products, and build AI-powered MVPs with real user testing, so your code won’t crumble when your first customers show up. Founded by entrepreneurs who’ve launched and exited their own startups, Gearheart has helped launch over 70 B2B SaaS products, including SmartSuite (which raised $38 million). They get where you’re at. Book your free strategy session at gearheart.io and mention Startups for the Rest of Us to get 20% off discovery, validation, or prototyping services. Topics we cover:  (3:12) – TinySeed returns Fund One (9:40) – GPT-5: Upgrade or letdown? (19:19) – Are we in an AI bubble? (24:09) – The Windsurf debacle: $2.4B exit, $0 for early employees (31:06) – The bigger problem: Are startups forgetting to share the upside? (40:05) – Lifestyle vs. Ambitious Bootstrapping Links from the Show:  TinySeed Fall 2025 Applications Live Q&A - Join us Wednesday September 3rd TinySeed SaaS Accelerator - Applications are Open! Invest in TinySeed MicroConf SaaS Institute Discretion Capital  Einar Vollset | LinkedIn Einar Vollset (@einarvollset) | X Tracy Osborn  Tracy Osborn | LinkedIn Tracy Osborn (@tracymakes) | X If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you! Subscribe & Review: iTunes | Spotify

Transcript

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0:00.0

You've stumbled upon another episode of Startups with the Rest of Us.

0:02.8

I'm Rob Walling, and in this hot take Tuesday, I welcome back Anar Volset and Tracy Osborne,

0:08.5

as we talk about Chat GPT5 and the struggles they've had with that release,

0:12.9

whether we're in an AI bubble, and a few other relevant news items.

0:16.8

One of them actually deeply relevant to SaaS sales.

0:19.6

Before we dive into the episode, I wanted to let you know that Tiny Seed applications are

0:23.3

open for the fall 2025 batch.

0:25.8

If you're a B2B SaaS founder with at least $1,000 in MRR and you're looking for

0:30.2

the right amount of funding, a community of ambitious, like-minded founders, and a network

0:34.4

of world-class mentors, you should apply.

0:36.9

If you have any questions about the

0:38.3

program or the application process, we're also doing a live Q&A with the Tiny Seed team this

0:43.0

Wednesday, September 3rd on YouTube. We'll link that up in the show notes. If you know your metrics,

0:48.1

the application only takes about 10 or 15 minutes to complete. Applications close on September 9th.

0:53.8

You can get all the details at

0:55.1

tiny seed.com slash apply. All right, let's get into it.

1:02.0

Welcome back to Hot Take Tuesday.

1:12.2

I have two guests, my recurring panel, and this is by popular demand.

1:17.3

And by that, I mean two people have mentioned it to me in the past six weeks saying,

1:21.1

why don't you do Hot Take Tuesday anymore?

1:23.4

And I was like, I don't know.

1:24.9

People have been traveling.

...

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