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Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
In this episode of This Week in Startups, host Jason Calacanis and Alex Wilhelm dive into the evolving landscape of executive function, AI browsers, and startup fundraising dynamics. The conversation kicks off with Jason sharing his innovative executive training program within his venture firm, addressing the widespread lack of executive skills among young professionals entering the workforce. (01:29) The discussion then shifts to the browser wars renaissance, focusing on Perplexity's Comet browser going from exclusive to free access and the strategic implications for AI companies competing with tech giants. (05:41)
Key topics include OpenAI's record-breaking $150 billion tender offer that establishes it as the world's most valuable private company, the meteoric rise of Sora's social video app to #1 on iOS, and innovative startup approaches like the Anti Fraud Company's private sector "DOGE" model. The episode also explores controversial territory with Apple's removal of the IceBlock app that tracked ICE agents, sparking debate about free speech versus public safety concerns.
Jason Calacanis is a veteran angel investor, entrepreneur, and host of This Week in Startups and the All-In Podcast. He's an early investor in companies like Uber and Robinhood, and currently runs Launch, a venture capital firm and accelerator. Calacanis is known for his direct approach to entrepreneurship and has been instrumental in mentoring hundreds of startups through his programs and investments.
Alex Wilhelm is the co-host of This Week in Startups and a seasoned technology journalist. He previously worked at Crunchbase and TechCrunch, where he covered startup funding, technology trends, and market analysis. Wilhelm brings deep experience in startup ecosystems and financial markets, having served on executive teams and covered the venture capital industry extensively.
Jason revealed that most young professionals entering the workforce lack basic executive skills, with only one in five possessing genuine self-direction abilities. (01:17) He implemented a comprehensive training program covering calendar blocking, start/end-of-day protocols, to-do list management, and crisp communication. Within just one week, participants improved from a 5/10 effectiveness rating to 6.5-7.5/10, with some going from working 35-40 hours per week to 50-60 hours. This 20% productivity increase across 21 employees equated to gaining four free additional team members. The key insight is that in today's distraction-heavy work environment, structured executive training can dramatically improve team performance and should be a priority for any growing organization.
Perplexity's decision to make their Comet browser free and remove the waitlist represents a strategic shift in how AI companies approach user acquisition. (05:41) Jason demonstrated how these browsers enable unprecedented automation, showing a shortcut that simultaneously scrapes multiple websites to create comprehensive tech news summaries. This functionality essentially turns every user into a potential data collection point for training AI models, creating what Jason calls a "backdoor copyright solution" where companies can access normally protected content through user browsing. With Polymarket showing a 74% chance of OpenAI launching their own browser by year-end, this signals that browser control will become essential for AI companies to maintain competitive advantage and access to training data.
The Lean AI Native Companies Leaderboard reveals companies achieving over $1 million in revenue per employee, fundamentally changing expectations for startup efficiency. (26:00) Companies like Midjourney with $12 million per employee and Telegram's extreme efficiency demonstrate what's possible with AI-first approaches. However, Jason warns this can indicate both over-profitability (not reinvesting in growth) and under-investment in scale. The key insight is that founders should target optimal revenue per employee ratios for their specific business models rather than chasing these extreme numbers. This efficiency focus could enable founders to maintain 20-40% ownership at exit instead of the traditional 10-20%, fundamentally changing wealth creation dynamics for entrepreneurs.
The Blue Bottle coffee shop networking story demonstrates how showing vulnerability and offering value can create meaningful connections more effectively than traditional networking. (18:23) By simply putting up a "coffee on me for valuable feedback" sign, one founder spoke with 121 people including three VCs in five hours. This approach works because it shows fearlessness, genuine interest in feedback, and the ability to engage with real humans - qualities that make entrepreneurs unique. Jason emphasizes that shorter, more personal outreach (showing interest in the recipient, leading with strong metrics, asking specific questions) dramatically outperforms lengthy biographical emails. The principle extends to social media engagement where being a valuable "reply guy" can build meaningful professional relationships.
OpenAI's $150 billion valuation in their tender offer establishes them as the world's most valuable private company, but Jason warns this represents "irrational exuberance." (38:10) The limited supply of shares in the tender (only $6.6B traded of $10.3B authorized) suggests employee confidence, but Jason recommends employees sell everything due to extreme risk concentration. Comparing to Microsoft and Google's $2-3 trillion valuations, he questions whether OpenAI can sustain this valuation when going public. The broader implication is that the massive capex investments in data centers and compute infrastructure will face scrutiny regarding return on invested capital, making 2025 a critical year for proving AI monetization at scale.