AI Rebuilt Every YC W26 Startup. Should Founders Be Scared? | E2271
This Week in Startups
Why OpenAI bought a tech podcast
Jason Calacanis and Lon Harris argue TBPN gives OpenAI a vibes-driven media channel and discuss podcast valuations in an AI bubble.
This Week In Startups is made possible by:
Deel - deel.com/twist
Grasshopper Bank - grasshopper.bank/twist
Render - render.com/twist
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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