Search for a command to run...

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, Jason Calacanis and Alex Wilhelm explore the rapidly evolving tech landscape, from AI browser wars to executive training insights. (01:09) Jason kicks off by discussing his new executive training program, which has dramatically improved team productivity by 20% through structured approaches like calendar blocking and disciplined communication. The hosts dive deep into the Perplexity Comet browser launch, analyzing the competitive dynamics as every major AI company races to develop their own browsing solutions. (36:02) They examine OpenAI's record-breaking $500 billion tender offer and discuss the implications of irrational exuberance in private markets. The conversation spans from innovative AI video creation with Sora to government regulation issues around the Ice Block app controversy.
Jason Calacanis is a prominent venture capitalist and angel investor who runs Launch, a venture capital firm. He's an early investor in companies like Uber and Robinhood, and hosts the popular "This Week in Startups" podcast and co-hosts the "All-In" podcast. Known for his direct communication style and insights into startup culture, Jason has been a key figure in Silicon Valley for over two decades.
Alex Wilhelm is a seasoned technology journalist and startup analyst who serves as co-host of This Week in Startups. He previously worked at Crunchbase on their executive team and has extensive experience at The Next Web (TNW), where he cut his teeth in technology journalism. Wilhelm brings deep expertise in startup analysis and venture capital trends to the show.
Jason discovered that most young professionals entering the workforce lack basic executive skills - only about one in five possess genuine self-direction capabilities. (01:09) His executive training program, focusing on calendar blocking, start/end-of-day routines, follow-up communication, and structured work habits, improved team effectiveness from 5/10 to 7/10 in just one week. This represents a 20% productivity increase equivalent to getting four free employees across a 21-person team. The takeaway emphasizes that in today's competitive landscape, basic executive discipline has become a rare and valuable skill that can dramatically differentiate both individuals and organizations.
The launch of Perplexity's Comet browser and the predicted 74% chance of OpenAI releasing a browser by year-end reveals a critical business model challenge. (05:41) These AI-powered browsers significantly increase compute costs per user while potentially serving as backdoors for training data collection. When users' browsers access restricted content like LinkedIn or Instagram through legitimate user accounts, AI companies can effectively bypass traditional scraping restrictions. This creates both an opportunity for data collection and a massive cost challenge that will define 2025's return on invested capital conversations in the AI sector.
Companies like Midjourney achieving $12 million in revenue per employee while others struggle with $125k per employee highlights the importance of understanding context behind efficiency metrics. (26:05) Jason warns that extreme profitability might indicate insufficient ambition - Midjourney could potentially expand into video (like Sora) or social features rather than maintaining such high margins. For startups, the key is balancing efficiency with growth investment, recognizing that different business models (marketplaces vs. software) require different workforce strategies and that sustainable scaling often requires strategic reinvestment of profits.
Modern founders can potentially own 20-40% of their companies at scale, compared to the traditional 10-20%, by being more strategic about fundraising. (31:43) Jason illustrates this with an example: instead of raising $3M at $10M (30% dilution), raising $1M at $10M (10% dilution), hitting milestones, then raising $2M at $20M (another 10% dilution) results in 20% total dilution versus 30%. This approach requires smaller teams, longer runway management, and hitting clear milestones between rounds. The strategy works best when founders can demonstrate consistent progress with minimal capital, particularly in today's AI-enhanced productivity environment.
The Blue Bottle coffee shop networking hack - sitting with a "coffee on me for valuable feedback" sign - demonstrates that physical presence and vulnerability create more meaningful connections than lengthy emails. (23:03) This founder connected with 121 people including three VCs in five hours. Jason emphasizes that effective investor outreach requires short, crisp emails showing genuine interest in the recipient, leading with your strongest metric (growth chart), and asking specific questions. The key principle is that people respond to those who show fearlessness and genuine human connection over generic mass outreach efforts.