AI Rebuilt Every YC W26 Startup. Should Founders Be Scared? | E2271

AI Rebuilt Every YC W26 Startup. Should Founders Be Scared? | E2271

Author: Jason Calacanis April 4, 2026 Duration: 1:20:52

This Week In Startups is made possible by:


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Plaud - Plaud.ai/twist


An AI “holding company” rebuilt dozens of YC Winter ‘26 startups in one weekend. Now we’re bringing the founder responsible into Jason’s Courtroom to defend himself.

PLUS a live demo of Boardy, the AI that acts like a virtual board member and makes crucial introductions. Find out why he gets to have so much agency, how creator Andrew D’Souza used him to raise his own $17 million round, and how this company ever plans to actually make money.

Plus Jason celebrates Apple’s 50th anniversary with a fiery rant about milking the ghost of Steve Jobs… Why OpenAI is acquiring a tech podcast… Jason’s favorite weighted vest for rucking… AND Lon’s Off Duty weekend streaming picks.

Guests

Marik Hazan:https://x.com/MarikHazan

Feltsense:https://feltsense.com/

Andrew D’Souza:https://x.com/andrewdsouza

Boardy:https://www.boardy.ai/


Timestamps:


0:00 Jason's direction for TWiST and thoughts on legacy media

5:14 Marik of Feltsense joins the show

6:10 Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin. You can check it out at https://Plaud.ai/twist and use code TWIST for 10% off!

7:10 Marik's viral YC replicator stunt

9:45 Deel - Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, get visas handled fast, and get back to building. Visit https://deel.com/twist to learn more.

20:39 Grasshopper bank - Time is money. Don't waste either. Go to https://grasshopper.bank/twist and get an exclusive $500 cash bonus just for opening an account.

21:33 Feltsense founder goes on trial!

25:26 Jason dunks on Bank of America's app

27:59 TBPN acquired by OpenAI

29:28 The All In Podcast is worth $1B!

30:13 Render - Find out why 5 million developers are already using the all-in-one cloud platform, Render. Go to https://render.com/twist and apply for the Render Startup Program to get $500-$100,000 in free credits, depending on your stage and backers.

33:02 Andrew D'Souza joins the show along with his agent, Boardy!

43:17 So how does Boardy make money?

48:32 Lon is becoming more and more "AI-pilled."

50:41 Tactical/ practical: "If we have data, let's look at data. If all we have are opinions, let's go with mine." -Jim Barskdale, former CEO of Netscape

1:01:00 Tactical/ practical: hire a PR firm to report on your competitors' wrongdoings.

1:02:58 Jason calls out Apple for being DISGRAZIAD!

1:15:09 Lon's TV pick of the week: "Something Very Bad is Going to Happen https://www.youtube.com/watch?v=vMc_pWm7G7o

1:19:52 Become an Angel Investor at https://thesyndicate.com/


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Every week, Jason Calacanis dives headfirst into the swirling vortex of Silicon Valley and global tech with This Week in Startups. It’s a direct line to the conversations shaping our digital future, moving far beyond surface-level news. You’ll hear Jason’s unfiltered analysis on everything from market shifts and media trends to the underlying mechanics of building a business, all delivered with a blend of enthusiasm and seasoned skepticism. The core of this podcast, however, lies in the guests. Jason sits down with the very people driving change-founders who have scaled impossible heights, operators managing daily chaos, and investors who spot trends before they become obvious. These conversations are less like formal interviews and more like insider debriefs, pulling back the curtain on real strategies, painful failures, and unexpected successes. For anyone curious about how technology is built, funded, and ultimately changes the world, this series offers a front-row seat. It’s the context behind the headlines, providing a deeper understanding of the forces at play in startups and technology. Tune in for a consistently engaging and insightful look at the ecosystem, straight from someone who lives and breathes it.
Author: Language: en-us Episodes: 100

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