This Week in Startups – Episode 2210

Archer Buys an Airport, Ramp’s Huge Raise, RIP KitKat, Bezos Returns to the C-Suite, and More
Host: Jason Calacanis
Date: November 18, 2025

Episode Overview

In this lively episode, Jason Calacanis and co-host Alex take listeners through a whirlwind of the week’s hottest stories in startups and tech, ranging from global founder environments and explosive AI startup growth, through Ramp’s eye-popping raise, the cultural fallout of a Waymo accident in San Francisco, to the blockbuster news of Jeff Bezos returning to the CEO seat—just not at Amazon. Through hands-on anecdotes, inside observations, and real talk about markets and macrotrends, Jason and Alex deliver candid insights for founders, investors, and tech-watchers.

Key Discussion Points and Insights

1. Jason’s Global Founder University Tour: Middle East & Japan

(02:14–15:59)

• Founder University in Riyadh:

  • Jason describes bringing his Founder University program to Riyadh at the invitation of Senabul, the venture arm of Saudi Arabia’s PIF.
  • Interest and participation far exceeded expectations: “We were going to have 25 companies. We had 60.” (05:34)
  • The Middle East is in “decade zero” of building tech companies and is flush with capital and ambition.
  • Unique needs in the region require adapting the American curriculum, particularly around design and development talent.

• Differences in Startup Focus:

  • Middle East: Huge construction/infrastructure projects, lagging fintech, and a boom in marketplaces.
  • Japan: Mature UX and design culture, strong domestic market, but challenges with building globally-facing companies.
  • Jason shares a tangible example from a Japanese stand-up sushi bar to illustrate product-market fit and design obsession.

Jason (on the Middle East):
“They’re in decade zero of building technology companies there… I was really impressed. These are great entrepreneurs with great ideas. The companies are different, the needs are different.” (05:40)

2. Ramp’s Massive Raise, SaaS Growth, and the New AI Wave

(15:59–25:24)

• Ramp’s $300 Million Raise at $32B Valuation:

  • Revenue doubled to $1B past year—about 10x faster than typical public SaaS.
  • Ramp touts “intelligent money" via AI agents for procurement, treasury, compliance.
  • Alex: “While this is clearly a marketing ploy to call money now intelligent, I think it actually has some merit…” (17:12)
  • Jason traces the automation journey: from American workers, to offshoring, to now AI doing routine finance work.

• Changing Growth Landscape:

  • Private AI companies' growth is dwarfing even the fastest SaaS public companies.
  • Public market lessons: “Your growth rate matters… whether you’re a 2 year old startup or a 20 year old company, an established one.” (24:25)

• Human Implications:

  • Office space vs. data center buildout—“We’re making office space for robots at a faster growth rate than we’re making office space for humans.” (18:15)
  • Remote work is becoming a luxury, as roles that can go remote can be automated or moved offshore.

Jason:
“If it can be done work-from-home, it can be done by somebody in a low cost market… and then the next stop is AI.” (21:01)

3. SaaS, Commoditization, and Dropbox’s Growing Pains

(25:24–32:41)

• Dropbox’s struggle: shrinking revenue and paying user numbers—“It’s a tough place to be.” (26:14)
• The danger of feature commoditization in big tech suites—e.g., Google adding calendar features years after startups innovated.
• Insight for founders: There’s “a five to ten year window” before “Google comes after you.” (31:31)

4. RIP KitKat: Waymo, Self-Driving Cars & Public Reaction

(33:18–39:52)

• KitKat the Bodega Cat:
  • A Waymo car in San Francisco’s Mission district hit and killed a beloved bodega cat, KitKat.
  • Surprisingly muted public response—Jason and Alex see this as a positive sign for self-driving tech adoption.
• Media framing and legal caution about accidents involving autonomous vehicles.

Alex:
"What matters here, we've reached a moment when something alive that was beloved was killed by a self driving car in a town full of crunchies. And...the reaction is kind of like, well, that's not going to change much. So I think this is actually very positive for the progress of self driving cars..." (34:23)

5. AI, Labor, Job Displacement & Quiet Hiring Freezes

(43:41–50:48)

• Mainstream unease about AI-driven job loss is growing—among both political parties and at the corporate level.
• Jason dissects Amazon, Uber, and DoorDash’s quiet moves to limit hiring as automation takes hold.
• “You watch what companies do with their dollars...what you get now is not quiet quitting, but quiet hiring.” (47:09)

6. Crypto Sentiment, Market Corrections & Political Tides

(52:03–57:36)

• Bitcoin’s price surged to all-time highs after Trump signaled support for crypto; since then, a sharp correction.
• Jason attributes crypto’s performance to a blend of sentiment, regulatory signals, and macro.
  • “The time to go all in was when [Trump] gave the keynote at a bitcoin conference.” (55:39)

7. Strategy for Founders: Raising in Hot Markets

(57:36–62:27)

• Founders with high growth shouldn’t hesitate to raise multiple rounds into momentum. If you’re not high growth, lower the raise, prove out traction, and build methodically.
• “If you’re growing and you have a war chest...raise into that growth even if you don’t need it.” (59:21)

8. BREAKING: Jeff Bezos Returns as CEO (Project Prometheus)

(00:00–00:18 & 62:27–70:48)

• Bezos announced as co-CEO (alongside Vic Bajaj) of stealth AI/lab company, Project Prometheus—$6.2B raised.
  • Goal: Bridge AI/LLMs and real world experimentation, possibly via AI-driven labs, not humanoid robots.
  • Notable comps: Periodic Labs, Emerald Cloud Lab, Radical AI.
  • “Does that mean humanoid robotics? Does that mean robots? Bezos is now back in the CEO seat. This is extraordinary news.” (00:18)
  • Jason theorizes on the motivation: maybe post-yacht-life, maybe presidential ambitions in the distant future.

Jason:
“The fact that he’s taking the CEO title is intentional… He’s going to be in the office, he’s going to get off the yacht, going to be at less fashion shows. I think what this says to me is Lauren Sanchez was like, you need to get a job.” (69:32)

9. Policy, Regulation & Techlash (Unions, Democracy, Local vs. Federal)

(39:06–41:52, 41:52–43:41)

• Incidents like the KitKat accident are rapidly becoming symbolic flashpoints, often morphed by political agendas.
• Tension between local, state, and federal regulation on emerging tech—states testing their own approaches (AI, data center siting, etc).
• “This is where like the press needs to just keep doing a little bit better.” (36:39)

10. Closing Thoughts

Jason teases a This Week in AI spin-off, encourages superhuman productivity via AI tools, and closes with practical founder fundraising advice and some political speculation.

Notable Quotes & Timestamp Highlights

• On Global Talent Gaps:
  “Finding and recruiting developers is something in Saudi, in Abu Dhabi, Dubai, Doha, you know, in different places where we needed to build a module for that.” (09:41)
• On Office Work & Automation:
  "If it can be done work from home, it can be done by somebody in a low cost market... So it would make sense that the next stop is AI." (21:01)
• On Valuation Multiples:
  “Your growth rate matters… and your profitability matters... the marketplace is screaming, put money into the momentum stocks.” (24:25; 62:27)
• On Dropbox's Fate:
  “Sometimes you can get public, and then, and then struggle.” (32:41)
• On Policy & Democracy:
  “There's an interesting question of who gets to decide what happens on their roads..." (39:53)
• On Founding Bets:
  "If you’re growing and you have a war chest...raise into that growth even if you don’t need it." (59:21)
• On Bezos’s Motivation:
  "I think what this says to me is Lauren Sanchez was like, you need to get a job." (69:32)

Important Segments (Timestamps)

• Jason’s Middle East & Japan founder lessons: (02:14–15:59)
• Ramp’s raise & the AI startup advantage: (15:59–25:24)
• Dropbox & startup commoditization: (25:24–32:41)
• KitKat and AV culture war: (33:18–39:52)
• Labor, AI & the ‘quiet hiring freeze’: (43:41–50:48)
• Crypto sentiment shift: (52:03–57:36)
• Startup fundraising tactics now: (57:36–62:27)
• Bezos back as CEO (Project Prometheus): (62:27–70:48)

Tone and Style

Jason and Alex’s conversational, direct, and occasionally irreverent style makes for an energetic and information-rich discussion. Jason is especially candid with founder advice and insider critiques, while Alex brings timely news and sharp skepticism.

For more:

• ThisWeekinStartups.com/youtube
• Jason’s newsletter: calacanis.substack.com
• Alex’s daily recap: CautiousOptimism News Tharamahundi

Summary prepared for listeners who want a deep, actionable digest of the episode—minus the ads, filler, and banter.