4.4 • 1.3K Ratings
🗓️ 8 August 2025
⏱️ 79 minutes
🧾️ Download transcript
Today’s show:
Jason and Lon recorded a Thursday night special edition, so no Alex this time, but still lots to talk about.
First up, Jason thinks it’s time for Tim Apple to exit the stage in lieu of a product obsessive innovator. Speaking of new products, GPT-5 is here and the hosts are… not exactly blown away. Are we in the midst of the AI trough of despair?
PLUS we’re talking Ripple’s acquisition of Rail, Donald Trump’s new AI chatbot, Bumble’s new direction, Airbnb’s potential paths forward and MUCH MUCH MORE.
Timestamps:
(0:00) Why Jason thinks Apple lacks innovation (plus a look back at his 2019 thoughts)
(08:54) Sentry - New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWIST
(09:54) Show continues…
(20:10) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!
(21:18) Is GPT-5 coming for Lovable and Bolt?
(29:42) Alphasense - Get deeper insights into your business with the power of AI search and market intelligence. Start with a free trial at AlphaSense.com/Twist.
(30:55) Show continues…
(35:05) Ripple buying Rail, and why sometimes regulations are GOOD for companies
(43:28) Is Ripple about to become the MicroStrategy of XRP?
(47:48) Truth Social AI is perplexing, powered by Perplexity
(53:27) Should people be using ChatGPT for therapy? What do you think? How does that make you feel?
(01:04:42) Anthropic’s Dario Amodei recalls his greatest haters
(01:11:04) Bumble but… for friendship?
(01:12:20) DoorDash’s crazy growth, and the guys discuss who should buy Airbnb
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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:
(08:54) Sentry - New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWIST
(20:10) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!
(29:42) Alphasense - Get deeper insights into your business with the power of AI search and market intelligence. Start with a free trial at AlphaSense.com/Twist.
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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Substack: https://twistartups.substack.com
Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916
Click on a timestamp to play from that location
| 0:00.0 | That's what Steve Jobs actually wanted to do. |
| 0:02.0 | He wanted to make these products here. |
| 0:04.6 | And you and I were having a private discussion about just how disgracziad this company is. |
| 0:10.7 | It's disappointing. |
| 0:12.1 | That's how I feel. |
| 0:13.0 | I feel disappointed. |
| 0:14.0 | When we got the iPad, when we got the iPhone, you were looking forward to a lifetime of exciting Apple products. You were going to, |
| 0:22.1 | every five years, there was going to be some new, amazing innovation. And it has not been realized |
| 0:27.8 | that vision. Once we got through the pipeline of whatever Steve Jobs had thought of, there was |
| 0:36.4 | nothing bold left. And I said on, uh, CNBC, |
| 0:42.0 | I think there's a case for, for, uh, Tim Cook, you know, leaving. |
| 0:49.5 | This week in startups is brought to you by Century. Your team should be focused on shipping |
| 0:55.2 | features, not chasing down bugs. New users get three months free of the business plan, |
| 1:00.4 | which covers 150,000 errors. Go to century.io slash twist and use the code, twist. |
| 1:08.4 | Northwest Registered Agent. Starting your business should be simple. With Northwest |
| 1:13.4 | Registered Agent, you can form your entire business identity in just 10 clicks and 10 minutes. From |
| 1:19.6 | LLCs to trademarks, domains to custom websites, they've got you covered. Get more privacy, |
| 1:25.5 | more options, and more done. Visit northwest registered agent.com |
| 1:29.9 | slash twist today. And AlphaSense. Get deeper insights into your business with the power of |
| 1:37.2 | AI search and market intelligence. Start with a free trial at AlphaSense.com slash twist. |
| 1:43.6 | Hey everybody. Welcome back to this week in startups. Alex is taking a little break, and we're doing our show with my guy, Lon Harris, the original, one of the original co-hosts of this week in startups 14 years ago. The original. Episode one. You read the original. Yeah. Well, Tyler was sort of behind the scenes producing Tyler Crowley, our old friend. And then, but I was the news reader like right off the bat. Yeah. And he's still on the lamb? See, he's somewhere in Thailand, I believe, somewhere on a beach in Thailand. Oh, my God. I just, but when I said, people ask like, hey, whatever happened to Tyler from this week at stars, why isn't he around? And I was like, he's on a beach in Thailand. They're like, no, really. Not only. He's on a beach in Tyler. Shout out to Tyler. Come on the show anytime. He took the model of, like, doing events and stuff like that. then learned working with me, which I gave my blessing on him, took it to Stockholm, Sweden, |
| 2:18.4 | made like, and stuff like that. Then he learned working with me, which I gave my blessing on him, took it to Stockholm, Sweden. Right. Made like a million dollars a year for five years, bought a beach resort, and then hung it up. Right. He's retired. Every time I see a post from him, he's on a hammock. Yeah, I'm an idiot. I'm still here 10 here 10 years later yeah he taught him everything you know |
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