Podcast Summary: "THE 2025 TWISTY AWARDS! Biggest Trends, Best Guests, Top Name Drops, and More"

Podcast: This Week in Startups
Host: Jason Calacanis
Episode: E2229
Date: December 30, 2025

Overview

In this special year-end episode, Jason Calacanis and co-hosts Lon Harris and Alex Wilhelm present the "Twisty Awards" — a playful, rapid-fire review of the biggest trends, best guests, top moments, and the most memorable episodes from "This Week in Startups" in 2025. The team debates, reminisces, and often jokes about the standout moments, providing both nostalgia and critical insight into the past year's tech and startup landscape.

Key Discussion Points & Insights

1. Best Name Drop of 2025

• Nominees stroll down celebrity lane: Jason recounts run-ins and hangouts with figures like Elon Musk, Ben Stiller, Timothy Chalamet, Sergey Brin, and Tony Robbins.
• Highlight: The F1 race poker table with "basically the greatest table ever seen," featuring Timothy Chalamet, Travis (Uber), Chamath, David Friedberg, Shane from Polymarket, and more.
  • Quote (Jason, 05:02):
    “We had a nice poker game with Timothy Chalamet.”
• Court-side Knicks seats story also wins praise for both the names dropped and a dig at Detroit ticket prices.
• Winner: The F1 event edges out as the "deluxe name drop" for the sheer density and caliber of luminaries.

2. Biggest Trends of 2025

• Major themes debated:
  • The return of M&A (mergers and acquisitions) post-Lina Khan era.
  • AI-driven job displacement and looming youth unemployment crisis.
  • The arrival/rise of humanoid robots (Tesla's Optimus, etc.)
• Debate between hosts: Each panelist votes for a different trend, tying up the results.
  • Jason’s tie-breaker: M&A resurgence is crowned the most acutely “2025 trend.”
  • Quote (Jason, 07:29):
    “The wrath of Lina Khan ending and the Trump M and A bonanza begins...We need to let M and A rip or else we will not have risk capital at work. Let it rip.”
• Second place: Both AI job displacement and humanoid robots recognized as massive, soon-to-land phenomena.

3. Best Jason Anecdote

• Nominees:
  1. Jason confronts a LinkedIn doxxer — "Hey, dum dum, talk to your wife." (15:05–16:53)
  2. Jason’s guidance counselor origin story — being told he’d never get into college, and how that drove him.
  3. Private jet etiquette lessons — the four unspoken rules of flying with VIPs.
• Winner: The doxing saga, chosen for both its drama and Jason’s unorthodox but diplomatic resolution.
  • Quote (Jason, 16:36):
    “I said, so you’re married. I said, I tell you what, go talk to your wife, tell her what you did and ask her what she thinks is the best thing for you to do. I get an apology letter from him with his wife CC.”

4. Best Guest of 2025

• Nominees:
  • Doug Leone (Sequoia Capital): Venture capital's “sham/scam” and honest industry critique.
  • Coffeezilla: Dissecting meme coin scams, fraud, and crypto regulation.
  • Anton Osika (Lovable): The future of software, single-founder SaaS, and AI’s place in product development.
  • Rahul Vohra (Superhuman/Grammarly) & Vlad Tenev (Robinhood): Scaling, design culture, and leadership.
• Winner: Doug Leone for his candid, "hand grenades behind him" style honesty about VC incentives and greed.
  • Quote (Doug Leone via Jason, 22:57):
    “First of all, the sham of the scam that is called venture capital…We get paid…If we lose the money, so what? If we make money, we get the key...You wonder why the balance between greed and fear always lean towards greed.”

5. Best Jason Rant

• Rants in contention:
  1. Anti-remote work and pro-office socialization for young professionals.
  2. Movie theaters pricing and experience (AMCs, 3D, food costs).
  3. The security and privacy debacle with the “T app.”
  4. Mark Zuckerberg's decision-making — "You can’t trust Zuck."
• Winner: The enduring Zuck/META rant, praised for both passion and historical continuity ("since the beginning, you can't trust Zuckerberg.").
  • Quote (Jason, 35:01):
    “He needs an ombudsman...Zuckerberg does not have anybody around him telling him when they're doing stupid. This is a dangerous place for somebody with that much power to have.”

6. Most Controversial Moments

• Show’s spiciest moments include:
  • Jason’s argument against rich people piloting experimental vehicles.
  • Katy Perry's infamous Blue Origin spaceflight performance ("What a Wonderful World" in zero-G).
  • Podcast rivalry with Kara Swisher—"after $10 million, money doesn't matter."
  • Jason’s public and viral warning: "Never work with Sam Altman and OpenAI."
• Winner: The Katy Perry-in-space segment, for sheer entertainment, irreverence, and graphic rocket humor.
  • Quote (Jason, 39:11): “Rockets inherently look like penises. And then this one is designed to just look like a circumcised penis. Oh, God.”

7. Desgraciad of the Year

• “Disgraziad” defined: Jason’s Brooklyn-derived insult for entities that have deeply disappointed.
• Nominees:
  • Apple/Tim Cook: “Where are the new ideas??”
  • Vail Ski Resorts: Management and stock losses.
  • LA Mayor Karen Bass: Crisis leadership.
  • Bank of America mobile app (and legacy banking UX).
• Winner: Apple, for the loss of magic post-Jobs and underwhelming innovation since the iPhone/iPad golden years.
  • Quote (Jason, 44:37): “It is disgraceful that they can't come up with something super compelling other than this, like, tiny, thin phone...the camera sucks so bad.”

8. Best Alex Dad Jokes

• Nominees: Alex’s penchant for bad jokes, wordplay, and comedic timing.
  1. “Capacious” as the “c-word” he's allowed to call Jason.
  2. Raunchy stoner comedies as “my personality after 8pm.”
  3. “Please take everyone out to lunch because you have enough cash for that?” (re: Lightspeed Ventures $9B fund)
  4. Honorable mention: The enthusiastic “Yes, sir!” for Figma’s public filing.
• Winner: The “Yes, sir!” Figma moment, unanimously beloved by the team for its wholesome delivery.
  • Quote (Alex, 53:57): “Yes, sir, it's Figma.”

9. Bonus: Trump Impressions

• Most memorable Jason Trump impression:
  • “It's just a word. Groceries.” (55:10)

Notable Quotes & Moments

• On AI and Job Market Anxiety:
  “We're going to have job destruction. Everybody agrees on that... if we can create new jobs in that time period.” — Jason (08:19)

• On the ‘T app’ privacy bomb:
  “They didn’t encrypt the driver’s licenses, pictures and reviews of former dates or boyfriends that women were leaving in this app. So this is incredibly damaging on, like, multiple vectors.” — Jason (33:12)

• On private jet etiquette:
  “You let the principal decide where they're going to sit first... you wait for the principal to pick their seat…” — Jason (18:38)

• On podcasting and old rivalries:
  “All In makes much, much, much more money than Pivot does ... I think a little of this might be reverse jealousy.” — Jason (40:10)

Timestamps for Key Segments

• Name Drops: 02:16–06:17
• Trends of the Year: 07:03–14:01
• Best Jason Anecdote: 14:29–16:53
• Best Guest: 22:57–29:00
• Best Rant: 29:30–36:12
• Most Controversial Moments: 36:20–43:57
• Disgraciad of the Year: 44:08–50:50
• Alex Dad Jokes: 51:21–54:17
• Memorable Moments/Outro: 54:39–55:44

Tone & Style

The episode is self-aware, irreverent, and energetic — blending sentimental reflection, inside jokes, candid industry critique, and generous doses of friendly ribbing. The hosts’ chemistry and history together is palpable, with Jason’s trademark bluntness and Alex and Lon’s pop culture-savvy commentary keeping things lively.

Summary Takeaway

The 2025 "Twisty Awards" encapsulated not only the hottest stories and trends in tech, startups, and AI, but also the camaraderie and sharp humor that define the show. Whether for the best celebrity run-in, the "disgraziad" of the year, the most viral rants, or the most groan-worthy dad joke, this episode doubled as a yearbook for devoted listeners and a lively tech industry snapshot for newcomers.