Is $MSTR over? Jason takes his victory lap. | E2216
This Week in Startups
Jason Calacanis
4.4 • 1.3K Ratings
🗓️ 2 December 2025
⏱️ 58 minutes
🔗️ Recording | iTunes | RSS
🧾️ Download transcript
Summary
This Week In Startups is made possible by:
Quo - http://quo.com/TWiST
Squarespace - https://www.Squarespace.com/TWIST
Miro - http://miro.com/
Today’s show:Â
Michael Saylor’s Strategy play is struggling with the price of Bitcoin on a steep decline… Is his new “dollar reserve” the answer?
On TWiST, we’re looking into the state of $MSTR and why Jason remains SO skeptical about this increasingly convoluted financial scheme.
Is CNBC giving Michael Saylor a pass? Is that why he won’t go on “All-In”? And do investors realize that loans go BEFORE equity? We’re asking the TOUGH questions…
PLUS Jason’s Four Red Flags for companies with convoluted tactics… Why S&P Global downgraded Tether, and why Jason thinks the US government waited TOO LONG to pass stablecoin regulations… Jason reacts to the NYT “hit piece” on Bestie David Sacks… we’re checking out the new Matic robot vacuum and Sunday Robotics’ Memo bot… PLUS much more of the day’s biggest tech news and stories.
Timestamps:
(03:04) Why Jason broke his “No Demo Day” rule for the LAUNCH 35 Accelerator
(07:08) What we can learn from BitcoinTreasuries.net about the marketplace
(07:42) Why Jason remains SO skeptical on $MSTR… and any sufficiently convoluted financial scheme…
(7:56) Jason’s Four Red Flags for rogue companies and financial schemes
(9:49) Quo (formerly OpenPhone) gives you a clean, modern way to handle every customer call, text, and thread all in one place. Try it free at http://quo.com/TWiST
(14:31) When loans go before equity, and how this can dilute your investment!
(18:05) Is CNBC giving Michael Saylor a pass? Why Jason thinks he won’t go on “All-In.”
(19:30) Checking in with Polymarket’s thoughts on potential MicroStrategy Bitcoin sales
(20:21) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://squarespace.com/twist
(22:58) Speaking of complex schemes… why S&P Global downgraded Tether
(29:26) Is Tether too good to be true, as an investment?
(25:17) Why Jason thinks the US waited too long to pass stablecoin regulations.
(30:24) Miro - Help your teams get great done with Miro. Check out http://miro.com to find out how!
(36:15) Jason’s reaction to the NYT piece about Bestie David Sacks
(43:14) Is there a growing divide within the GOP about how to engage with tech companies?
(44:04) What are “Glue Employees” and why are they important?
(45:03) How to tell your “Glue Employees” apart from the “union reps” and other rabble rousers…
(51:50) Sunday Robotics: another human-ish robot but with WHEELS (and a baseball cap)
(56:05) We’re checking out the Matic robot vacuum as well… Should these products be combined?
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Follow Lon:
X: https://x.com/lons
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Follow Alex:
X: https://x.com/alex
LinkedIn: https://www.linkedin.com/in/alexwilhelm/
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Follow Jason:
X: https://twitter.com/Jason
LinkedIn: https://www.linkedin.com/in/jasoncalacanis/
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Thank you to our partners:
(9:49) Quo (formerly OpenPhone) gives you a clean, modern way to handle every customer call, text, and thread all in one place. Try it free at http://quo.com/TWiST
(20:21) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://squarespace.com/twist
(30:24) Miro - Help your teams get great done with Miro. Check out http://miro.com to find out how!
Great TWIST interviews:Â
Will Guidara
https://youtu.be/pvJa2pzuXWQ
Eoghan McCabe
https://youtu.be/9dHN4YFkgv4
Steve Huffman
https://podcasts.apple.com/us/podcast/reddit-ceo-steve-huffman-on-mod-revolt-building-a/id315114957?i=1000617333424
Brian Chesky
https://podcasts.apple.com/ca/podcast/airbnb-ceo-brian-chesky-on-early-rejection-customer/id315114957?i=1000611761112
Transcript
Click on a timestamp to play from that location
| 0:00.0 | This whole staple coin thing is like, hey, if tether's going to be buying treasuries of the United States |
| 0:05.0 | or Circle is doing that, we need to have this be regulated because these things are getting big. |
| 0:11.5 | People like digital money. People like being able to trade money quickly. Now, they'll, in their defense, |
| 0:17.0 | say, well, we can track everything. Therefore, that's better than, you know, bricks of |
| 0:21.9 | $100 bills. Perhaps maybe, sure, you can have that argument. The fact is, they don't pass |
| 0:28.5 | the U.S. very granular requirements to be currently traded in the United States legally and to be |
| 0:37.3 | like part of what USDC is doing. |
| 0:40.5 | Why would Paulo even bother owning Bitcoin? |
| 0:42.6 | Just if you want to make love to America, you want to be really sweet. |
| 0:46.7 | If you want to experience affection and joy in America in that market, it's very simple, buy our treasuries, we'll love you, buy our debt. |
| 0:58.3 | Yes, we'll be friends. |
| 0:59.5 | Now you're only going to make four or five percent on it as opposed to 15 percent, but then you'll be able to work here. |
| 1:05.9 | This weekend startups is brought to you by Miro. |
| 1:09.2 | Help your teams get great done with Miro. |
| 1:11.7 | Check out to Mero.com to find out how. |
| 1:14.2 | Squarespace. |
| 1:15.3 | Turn your idea into a beautiful website. |
| 1:17.7 | Go to Squarespace.com slash twist for a free trial. |
| 1:21.2 | When you're ready to launch, use offer code twist to save 10% off your first purchase of a website or domain. |
| 1:27.5 | And, Quo, founders move fast. |
| 1:30.8 | Their phone systems should too. |
| 1:32.8 | Quo, formerly open phone, gives you a clean, modern way to handle every customer call, |
... |
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