THE 2025 TWISTY AWARDS! Biggest Trends, Best Guests, Top Name Drops, and more | E2229

Key Concepts

• Major Trends in 2025: Return of M&A activity, AI-driven job displacement (especially entry-level), and the rise of humanoid robots.
• Controversial Moments of 2023: Graphic commentary on rocket design, disputes with Caris Swisser regarding podcast revenue and influence, and warnings about OpenAI’s data practices.
• Criticism of Big Tech: Skepticism towards companies like Apple and OpenAI, focusing on innovation stagnation and data exploitation.
• Jason Calacanis’ Perspectives: Strong opinions on wealth, business ethics, private jet etiquette, and the potential of humanoid robotics.
• Year-End Review: A retrospective look at memorable events, anecdotes, and trends discussed on This Week in Startups and the “Twist” podcast.

Part 1: The Twisties 2025 - A Year in Review

This segment of This Week in Startups presents “The Twisties 2025,” a year-end review of the most notable moments, trends, and stories from the past year’s episodes. Hosted by Jason Calacanis, Alex Wilm, and Lon Harris, the discussion is interspersed with advertisements for HubSpot, Squarespace, and LinkedIn Ads.

Memorable Name Drops

The segment began with a lighthearted look at Jason Calacanis’ frequent name-dropping, highlighting three instances: time spent at X AI offices with Elon Musk and a member of the XAI team named Roman; attending a Knicks game with Ben Stiller, Timothy Chalamet, and his brother Josh; and attending the All In F1 spectacular in Miami alongside Nico Rosberg (F1 champion), Sergey Brin (Google co-founder), Tony Robbins, Antonio Baras (Doge developer), and Mayor Francis Suarez.

Key Trends of 2025

Three major trends were identified as defining the year: the return of Mergers and Acquisitions (M&A), driven by a potential shift in the regulatory environment – specifically referencing a “Trump M&A Bonanza” and the end of “the wrath of Lena Khan”; growing concern over AI job displacement, particularly impacting entry-level positions in law and programming, and potentially eroding the gig economy; and the arrival of advanced humanoid robots like Optimus (Tesla), Figure, 1X, and Neo, which Jason predicts could become the most successful products in history, even surpassing the automobile. Jason stated, “I believe Optimus is going to be the greatest product ever created by humanity, including the wheel in this.”

Notable Anecdotes

Jason shared three personal anecdotes: a story about identifying and confronting someone who doxed him online, ultimately receiving an apology letter co-signed by the perpetrator’s wife; a recollection of a high school guidance counselor dismissing his academic potential, which fueled his ambition; and a detailed explanation of the unwritten rules of private jet etiquette, emphasizing punctuality, discretion, and respecting the principal’s seating preference. He also touched on Katy Perry’s Blue Origin flight as an example of attention-seeking behavior.

Part 2: Most Controversial Moments of 2023

This segment focused on the most controversial and memorable moments from the “Twist” podcast throughout 2023, categorized into “Most Controversial Moments,” “Disgraciad of the Year,” and “Best Alex Dad Jokes.”

Most Controversial Moments

The most contentious discussions included a graphic comment regarding the phallic design of a rocket, with Jason stating it was “designed to evoke a certain…phallic image” and resembling a “circumcised penis”; a public dispute with former podcast host Caris Swisser, where Jason asserted that “All-In” generates significantly more revenue and has higher rankings than “Pivot,” dismissing concerns about money after reaching $10 million; and a strong warning against developers using OpenAI’s API, claiming Sam Altman (OpenAI CEO) operates like Mark Zuckerberg, studying users and exploiting their innovations, referencing Microsoft’s historical pattern of adopting competitor products. Jason warned, “Sam Altman comes from the Zuckerberg School of Business…steal every innovation they have,” and cautioned against OpenAI potentially “backdoor[ing] your data into their models.” This segment was identified as the most controversial by the team.

Disgraciad of the Year (Jason’s Awards)

Jason awarded his “Disgraciad of the Year” to Apple under Tim Cook’s leadership, criticizing the lack of groundbreaking innovation since Steve Jobs’s tenure; Vail Resorts (MTN), citing a 50% stock price decline and “utter incompetence”; LA Mayor Karen Bass, for perceived inaction during a city emergency while traveling in Ghana; and Bank of America, for its outdated and inferior mobile app interface.

Lighthearted Moments: Alex’s Dad Jokes

The segment concluded with a lighthearted recap of Alex’s best dad jokes of the year, including puns involving “capacious,” “runchy stoner comedy,” a shoutout to Lightseed Ventures, and an enthusiastic “Yes sir” response to news about Figma’s IPO.

Conclusion

These segments provide a comprehensive year-end review, highlighting key trends in technology and venture capital, Jason Calacanis’ strong opinions on various topics, and the most controversial moments discussed on This Week in Startups and the “Twist” podcast. The overarching takeaways emphasize the potential for significant disruption from AI and robotics, a cautious outlook towards large tech companies, and the cyclical nature of market trends like M&A activity. Jason’s perspective, often blunt and provocative, consistently challenges conventional wisdom and offers a unique lens through which to view the evolving tech landscape.