THE 2025 TWISTY AWARDS! Biggest Trends, Best Guests, Top Name Drops, and more | E2229
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
This episode of "This Week in Startups" presents the annual TWISTY Awards, recognizing the best moments, guests, and trends from 2025. Host Jason Calacanis, along with co-hosts Alex Wilhelm and editorial director Lon Harris, review the year's highlights through curated clips and commentary. (01:40) The awards ceremony format covers categories from best name-drops and controversial moments to top guests and biggest trends that shaped the startup ecosystem in 2025.
- Main themes include: M&A market revival, AI job displacement concerns, humanoid robotics emergence, memorable guest interviews, and Jason's most passionate rants about industry developments.
Speakers
Jason Calacanis
Jason Calacanis is the host of "This Week in Startups" and a prominent angel investor and entrepreneur. He's known for his frank commentary on the tech industry and has been involved in notable investments and ventures throughout Silicon Valley. Jason also co-hosts the popular "All In" podcast and is recognized for his outspoken views on tech policy and startup culture.
Alex Wilhelm
Alex Wilhelm serves as co-host of "This Week in Startups" and brings extensive experience in tech journalism and startup coverage. He's known for his analytical approach to market trends and his occasional dad jokes that have become a running theme on the show. Alex provides balanced commentary on funding rounds, IPOs, and startup developments.
Lon Harris
Lon Harris is the editorial director for "This Week in Startups" and plays a key role in curating and organizing the show's content. He brings editorial expertise and helps structure the show's coverage of startup trends and industry developments. Lon contributes to the show's analytical depth and content strategy.
Key Takeaways
M&A Market Revival Signals Major Opportunity
The end of Lena Khan's regulatory approach and the incoming Trump administration has created a renewed environment for mergers and acquisitions. (07:07) Jason highlighted how one of their portfolio companies was getting acquired, representing the broader trend of increased M&A activity. This shift represents a fundamental change from the restrictive regulatory environment that previously constrained deal-making. The practical implication is that companies can now more realistically plan exit strategies through acquisition, and larger companies can pursue growth through strategic purchases without facing the same regulatory headwinds.
AI Will Accelerate Job Displacement for Young Workers
The discussion revealed a concerning trend where AI automation is specifically targeting entry-level positions in knowledge work, while traditional gig economy jobs are also being automated. (08:22) Jason predicted this would create a youth unemployment crisis, noting that companies are choosing automation over training young workers because the time investment no longer makes economic sense. This creates a double burden where both white-collar entry positions and service jobs are disappearing simultaneously, leaving fewer pathways for young people entering the workforce.
Humanoid Robots Represent the Next Major Product Category
Jason made a bold prediction that humanoid robots, particularly Tesla's Optimus, will become "the greatest product ever created by humanity, including the wheel." (11:24) The convergence of multiple robotics companies reaching critical mass in 2025, from Sunday Robotics to Figure's impressive package-sorting demonstrations, suggests this technology is moving from experimental to practical. This trend indicates that robotics will transform from industrial applications to consumer products that could fundamentally change how we work and live.
Platform Risk Requires Strategic Caution with AI APIs
Jason issued a stark warning against building businesses dependent on OpenAI's API, comparing Sam Altman's strategy to Mark Zuckerberg's historical approach of studying platform users before competing with them. (43:55) The concern is that companies using commercial AI APIs are essentially providing training data and business intelligence to potential competitors who control the underlying technology. This creates significant platform risk where AI companies can study usage patterns and then build competing products directly.
Remote Work Harms Professional Development for Young Workers
The discussion around the anti-work subreddit revealed Jason's perspective that remote work particularly disadvantages young professionals who need mentorship and professional development. (29:30) He argued that being physically present near "the locus of power" and receiving direct feedback from experienced colleagues is crucial for career development. This suggests that while remote work may offer lifestyle benefits, it may create long-term career disadvantages for those early in their professional journey.
Statistics & Facts
- All In podcast generates "much, much, much, much, much more money than Pivot does" and ranks higher despite being only four years old compared to Pivot's longer history. (40:11)
- Vail Resorts (ticker: MTN) stock lost half its value from 2021 to 2025, dropping from $272 to approximately $136, indicating poor management performance. (45:50)
- Family movie theater costs have reached approximately $50 per person ($250 for family of five) when including IMAX pricing and food service at luxury theaters. (31:58)
