Podcast Summary: "Is $MSTR over? Jason takes his victory lap." | This Week in Startups E2216 (Dec 2, 2025)

Episode Overview

In this episode, host Jason Calacanis is joined by journalist Alex Wilhelm to dissect the ongoing situations around MicroStrategy’s Bitcoin strategy collapse, Tether’s stability rating downgrade, stablecoin regulation, media coverage of David Sacks’ government service, and the role of underappreciated “glue employees” in tech startups. The episode features pointed analysis, memorable banter, and candid industry predictions, all in the duo’s characteristically incisive and irreverent style.

Key Discussion Points & Insights

1. MicroStrategy’s Bitcoin Strategy Collapse

• Background: MicroStrategy ($MSTR) had long traded at a premium over the value of its Bitcoin holdings due to aggressive leveraging and a continuous bullish stance by CEO Michael Saylor.
• Recent Change: The stock has now fallen to a net asset value (NAV) discount. The company's market cap is now less than the value of its bitcoin holdings, signaling a stark reversal (06:46).
  • Jason’s Analysis: Previously, investors paid a multiple of the company’s bitcoin assets (as much as 3x). Now, this discount reflects not only lost confidence but the risk from debt/funding mechanisms layered atop (05:44–07:17).
• Red Flags Identified by Jason:
  1. Complexity: Too convoluted for average investors.
  2. Too Good To Be True: Unsustainable returns and promises.
  3. Lack of Auditing: Poor transparency around financials (07:15).
  • Quote: "Whenever a company can't explain its business model to a 12 year old, it's a massive red flag. MSTR is so convoluted...that's ng. That's short for 'not good.'" — Jason (08:13)
• Financial Engineering at MicroStrategy: Discussion of how the company raised capital through complex euro-denominated perpetual preferred stock with high coupon rates (09:03).
  • Alex: "It's excessively clever, if you will." (09:49)
• Michael Saylor’s Evangelism: Saylor’s advice to “sell your home and buy bitcoin” viewed with deep skepticism.
  • Jason: "Would I say 'sell my house and buy more shares [of Robinhood or Uber]'? No, I actually wouldn’t say that." (11:36)
  • Alex: "Suggested true believers sell a kidney before offloading his favorite crypto...you gotta say, he’s a very consistent guy, Jason." (12:29)
• Social Media Backlash: Jason highlights being attacked by anonymous “MicroStrategy Army” accounts, many of which appear to operate from overseas “for engagement farming” (13:12).
• Loans and Leverage Risks: Explains how loan holders are ahead of equity holders if the company falters, comparing it to his own experience with venture debt (14:40–16:05).

Jason’s “Victory Lap”

• Jason predicted MicroStrategy’s downfall in 2025, which played out as he described — the stock lost two-thirds of its value (18:44–19:09).
  • Alex: "[Jason] predicts that MicroStrategy’s Bitcoin strategy will fail in 2025 … months later, they’ve lost two-thirds of their value. 10 points." (18:47)
• Market Speculation: Polymarket odds reflect public sentiment about a forced Bitcoin sale by MicroStrategy in 2026 (19:25).

2. Tether, Stablecoins, and Regulatory Pressure

• S&P Downgrade: S&P Global downgraded Tether (USDT) from 4 ("constrained") to 5 ("weak") concerning its peg stability due to increasing exposure to risk assets (22:52).
  • Risks: 5.6% of USDT backed by bitcoin, other high-risk holdings like corporate bonds, precious metals, and bitcoin-secured loans have ballooned to 24% of assets (23:50, 27:21).
  • Alex: "Every attestation that’s not an audit makes me worry more, not less." (32:02)
• Jason’s Critique:
  • Reiterates that the company lacks a proper audit, is overly complex, attacks critics, and presents returns too good to be true (30:56–32:16).
  • Quote: “Occam’s razor would state...the most logical reason [Tether] won’t do an audit is they wouldn’t pass it.” (33:15)
• Audit vs. Attestation:
  • Jason: Explains attestations are point-in-time and easily gamed; audits can be limited in scope if arranged that way (33:30–33:52).
• Tether’s Response to Downgrade: Tether exec Paolo claims S&P didn’t account for “retained earnings,” but Alex dismisses this as a distinct issue from collateralization (35:09–35:52).
• Regulatory Landscape:
  • Discusses the push for US-based stablecoins (Backed by Circle/USDC), new regulations (e.g., the "Genius Act"), and upcoming competition from major fintech and banks (36:51).
  • Jason: “There’ll be 10 other stablecoins in the US at this time next year from major entities...all of the incredible gains…at Tether...are going to be competed away." (37:14–37:52)

3. Media Scrutiny: David Sacks, AI, and Tech in Government

• NYT Article on David Sacks: Coverage of David Sacks’ government role, alleging that he’s steering regulation in ways that “benefit himself and his friends” (38:38).
  • Jason: Decries the headline as defamatory, emphasizes Sacks’ transparency and personal sacrifices (39:51).
  • Alex: Points out there isn’t a real issue if those benefiting are aligned with America’s AI and tech interests. (40:13)
  • Jason: “If America wins the AI race, every American wins.” (41:01)
  • On “agenda”: Jason embraces that policy direction is deliberate — pro-AI, pro-crypto, pro-American companies (42:50).
• GOP Divides: Discusses the internal debate in the Republican Party on tech and AI policy, e.g., differences between Trump allies, Bannon, and Hawley (43:21).

4. Startups, Team Culture, and “Glue Employees”

• Glue Employees:
  • Inspired by behavioral scientist John Levy’s new book, Alex and Jason identify the core role of "glue" employees — those with high EQ who help teams operate more smoothly (44:36–49:05).
  • Examples: Sheryl Sandberg, internal system managers — often not stars but integral to company success.
  • Management Advice: Regularly rotate team members and back up institutional knowledge to prevent single points of failure (49:30–51:39).
  • Quote: "When she [Crunchbase glue employee] went on vacation, the company struggled, and when she came back, everyone would just go – her desk was like a line…" — Alex (48:49)
  • Organizational Anti-fragility: Jason advocates cross-training and documented processes for startup resiliency (50:59).
  • Jason: “The foundational employees create stability. So as a founder, you need to understand if this person… is really creating a strong foundation for the company.” (47:08)

5. Robotics & Startup Innovation

• Sunday Robotics: Discussion of their wheeled, Roomba-like humanoid robot (Memo) for home tasks, which differs from bipedal robots in practicality and cost (54:47).
  • Jason: Praises the design and suggests hybridizing with robot vacuum companies, driving the price lower for broader adoption.
  • Training Data: Memo’s hand learned fine control from distributed “memory gloves,” innovatively crowdsourcing manipulation skills (55:41).
  • Product Fit: Both note size and cost will limit this tech to new, open-plan homes initially (54:47–56:56).
  • Jason: “Put the Matic at the bottom of a Sunday and then it’s cleaning the floors while it’s picking up the dishes.” (57:17)

Notable Quotes & Memorable Moments (with Timestamps)

• On $MSTR's Collapse:

  • “I did say don’t buy this and I did give financial advice and I said buy your bitcoin directly… What can we learn from this? Well, when things seem too good to be true and things seem financially complicated, those are two of the biggest red flags." — Jason (07:15)
  • "Suggested true believers sell a kidney before offloading his favorite crypto…" — Alex, on Saylor (12:29)
  • “MicroStrategy fans who attack me can make me a f***ing ham sandwich. You lost two thirds of your money and I told you you would.” — Jason (21:37)

• On Tether and Stablecoins:

  • “Every attestation that’s not an audit makes me worry more, not less.” — Alex (32:02)
  • "Occam’s razor would state...the most logical reason is they wouldn’t pass it. If you’d pass it, you do it.” — Jason (33:15)
  • “Why would Tether’s Paolo… even bother owning bitcoin? Just if you want to make love to America… Buy our treasuries, we'll love you. Buy our debt, yes, we'll be friends.” — Jason (25:16; 26:49)

• On Media & Policy:

  • “If America wins the AI race, every American wins.” — Jason (41:01)
  • “They bundled that…circle, Stripe, USDC… would have become the dominant players in stablecoins, not an offshore company…” — Jason on regulatory failures (36:51)

• On Organizational Health:

  • “The foundational employees create stability. So…are they really creating a strong foundation for the company…you need some of those.” — Jason (47:08)
  • “When she went on vacation, the company struggled… she was also super kind, super patient and helped everybody get so much done. She was the glue of the company.” — Alex (48:49)

Important Segment Timestamps

• MicroStrategy Discussion & Breakdown: 05:11–19:25
• Tether/S&P Downgrade & Stablecoins: 22:38–37:52
• David Sacks/Media Coverage/American Tech Policy: 38:38–43:21
• Glue Employees & Company Culture: 44:02–51:39
• Sunday Robotics & Robotics Market: 51:39–57:17

Tone and Style

The episode is energetic, sharp, and peppered with dry humor, analogies, and pop culture references (e.g., “get your shine box,” Goodfellas; "make me a ham sandwich!" – Jason’s Brooklyn-style taunt at online detractors). Both hosts are candid, skeptical of hype, and passionate about transparency and sound business practices.

Summary Takeaways

• Don’t fall for convoluted business models or charismatic evangelists without understanding first-principles math, especially in the crypto/fintech space.
• Demand transparency (audits vs. attestations) for stablecoins and similar financial instruments.
• Policy shifts (AI, crypto) are being guided by people with direct industry stakes, but national benefit can align with sectoral benefit.
• Organizational stability relies on not only star performers but foundational “glue” employees—find and retain them.
• Startup robotics and other new tech are on the cusp of household viability but currently appeal most to early adopters and new builds.

For those who missed the episode, this summary offers a complete view of the essential discussions, memorable moments, and actionable insights, all in the hosts’ original direct, skeptical, and humorous voice.