This Week in Startups
This Week in Startups

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

This Week In Startups is made possible by: LinkedIn Ads - http://linkedin.com/thisweekinstartups Squarespace -https://squarespace.com/twist Hubspot - http://clickhubspot.com/twist1 Today’s show: We’re saying goodbye to 2025 with our annual TWISTY Awards, looking back on our favorite pod moments from

Featured Speakers

Jason Calacanis Host

Topics Discussed

Episode Summary

Executive Summary: This year-end Twisties episode is a playful awards recap of the podcast’s 2025 highlights, centering on recurring themes like M&A revival, AI-driven job displacement, humanoid robots, memorable guest appearances, and Jason Calacanis’s many rants, anecdotes, and name-drops. The hosts debate winners across categories while using clips to illustrate the year’s most notable moments and evolving tech-industry narratives.

Main Topics: Year-end awards format and retrospective (Priority: 5/5): The episode is structured as the annual 'Twisties' best-of awards, with Jason, Lon, and Alex revisiting major moments from 2025 and selecting winners across categories. Major 2025 trends: M&A, AI displacement, humanoid robots (Priority: 5/5): The hosts identify the return of M&A after regulatory pressure, growing concern about AI eliminating jobs, and the rapid rise of humanoid robots as the defining macro themes of the year. Best Jason anecdotes and personal stories (Priority: 4/5): Jason’s stories about doxxing, private jet etiquette, and his origin story provide the episode’s most personal and humorous segments while reinforcing his 'inside baseball' perspective. Top guest appearances (Priority: 4/5): The show highlights standout interviews with Doug Leone, Coffeezilla, Anton Osika, Rahul Vora, and Vlad Tenev, emphasizing candidness, product thinking, and strong design or crypto commentary. Most controversial moments (Priority: 4/5): The hosts revisit spicy takes on experimental pilots, Katy Perry’s Blue Origin flight, Kara Swisher, and OpenAI/Sam Altman, underscoring Twist’s willingness to provoke. 'Descraziad' and criticism of companies (Priority: 4/5): A recurring comedic category targets companies and leaders Jason sees as underperforming, especially Apple, Vail Resorts, Karen Bass, and Bank of America’s mobile app. Recurring humor and running bits (Priority: 3/5): The episode leans on recurring jokes, name-drops, Trump impressions, and Alex’s dad jokes, showing the chemistry and informal tone that define the show.

Key Arguments: M&A returned in 2025 as regulatory pressure eased, and Jason sees this as one of the year’s most important shifts. AI will destroy or reshape many jobs, especially early-career white-collar roles, and the timeline is the main uncertainty rather than the outcome. Humanoid robots, especially Tesla Optimus, could become the most important consumer product category ever, even eclipsing Tesla cars. Young people should seek office-based work and mentorship because remote work and AI automation reduce professional development opportunities. Some companies and industries are failing to meet user expectations; Apple, Vail, and Bank of America were criticized as poorly managed or creatively stagnant. Guests and founders offered unusually candid, high-signal commentary when they were willing to criticize their own industries or admit uncomfortable truths. Jason believes platform companies like Meta and OpenAI should not be blindly trusted because they learn from users and may appropriate ecosystem value. The show’s strength comes from mixing serious analysis with comedic personal stories and improvised banter. Experimental or high-risk hobbies for wealthy people were mocked as unnecessary and preventable risks. The hosts frame the episode as a definitive review of what mattered most across a year of podcasting and tech discourse.

Data Points: Number of name-drop nominees: 3 - Best Jason name-drop category narrowed to three clips. F1 guest lineup size: 10+ notable guests - Jason described an F1 event featuring Sergey Brin, Tony Robbins, Antonio Varas, Mayor Francis Suarez, and others. Private jet rules: 4 - Jason listed four rules for flying private: don’t be late, take pictures, let the principal choose the seat, and read the room. Vail stock loss over five years: about 50% - Jason cited Vail Resorts’ stock price as evidence of poor management. Bank of America app comparison: unquantified but described as inferior to Venmo and Robinhood - Used as an example of a 'disgraceful' user experience. Doug Leone compensation structure criticism: 20% to 30% carry - Leone criticized venture capital incentives and fees. Apple innovation cycle: every 5 years, expected new product category - Jason lamented that this Steve Jobs-era pattern did not continue under Tim Cook. Episode count discussed: 150+ episodes - The hosts said the show covered roughly 150+ episodes during the year.

Pivotal Quotes: "I believe Optimus is going to be the greatest product ever created by humanity, including the wheel in this, obviously." — Jason Calacanis: Used in the 'biggest trend of 2025' discussion about humanoid robots. "We're going to have job destruction. Everybody agrees on that. The only thing people don't agree on is the timeline." — Jason Calacanis: Referenced during the AI job-displacement trend segment. "If you are a young person... you should be demanding that. You're getting ripped off." — Jason Calacanis: From the rant arguing that young workers should prefer office environments for mentorship and growth.

Implications: The episode suggests 2025’s tech story is shifting toward consolidation, automation, and embodied AI, while also rewarding candid critique and personality-driven media. Listeners should expect more labor disruption, more M&A, and growing scrutiny of platform power.

🔓 Sign Up for Unlimited Episode Search

About This Week in Startups

Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world’s greatest founders, operators, investors, and innovators.

View all episodes from This Week in Startups