Command Palette

Search for a command to run...

PodMine
This Week in Startups
This Week in Startups•October 4, 2025

Sora app review, Perplexity’s Comet is FREE, and which AI tools reign supreme? | E2188

In this episode, Jason Calacanis and Lon Harris discuss the latest tech news, including Perplexity's free Comet browser, OpenAI's Sora app reaching the top of the iOS App Store, and potential disruptions in AI, browsers, and whistleblower technologies.
Creator Economy
AI & Machine Learning
Indie Hackers & SaaS Builders
Tech Policy & Ethics
Developer Culture
Sam Walton
Sam Altman
Jason Calacanis

Summary Sections

  • Podcast Summary
  • Speakers
  • Key Takeaways
  • Statistics & Facts
  • Compelling StoriesPremium
  • Thought-Provoking QuotesPremium
  • Strategies & FrameworksPremium
  • Similar StrategiesPlus
  • Additional ContextPremium
  • Key Takeaways TablePlus
  • Critical AnalysisPlus
  • Books & Articles MentionedPlus
  • Products, Tools & Software MentionedPlus
0:00/0:00

Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.

0:00/0:00

Podcast Summary

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.

  • Main themes include AI infrastructure monetization, executive skill development, startup efficiency metrics, and the intersection of technology with regulatory challenges

Speakers

Jason Calacanis

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

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.

Key Takeaways

Executive Function is the New Competitive Advantage

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.

AI Browser Wars Signal Infrastructure Monetization Challenges

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.

Revenue Per Employee Metrics Demand Strategic Nuance

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.

Founder Equity Preservation Through Disciplined Capital Raising

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.

Direct Networking Beats Digital Outreach

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.

Statistics & Facts

  1. Only 1 in 5 people entering the workforce have genuine executive function and self-direction capabilities, according to Jason's observations. (02:02) This statistic underscores a fundamental skills gap in the modern workforce.
  2. Polymarket shows a 74% chance that OpenAI will release a web browser by the end of 2025, indicating strong market confidence in the expansion of AI companies into browsing. (09:05)
  3. Reddit's stock dropped 13% over five trading days, from around $240 to $208 per share, potentially due to Google's SEO changes that limit bulk search result access. (15:56) This demonstrates the significant financial impact of search engine algorithm changes on content-dependent businesses.

Compelling Stories

Available with a Premium subscription

Thought-Provoking Quotes

Available with a Premium subscription

Strategies & Frameworks

Available with a Premium subscription

Similar Strategies

Available with a Plus subscription

Additional Context

Available with a Premium subscription

Key Takeaways Table

Available with a Plus subscription

Critical Analysis

Available with a Plus subscription

Books & Articles Mentioned

Available with a Plus subscription

Products, Tools & Software Mentioned

Available with a Plus subscription

More episodes like this

In Good Company with Nicolai Tangen
January 14, 2026

Figma CEO: From Idea to IPO, Design at Scale and AI’s Impact on Creativity

In Good Company with Nicolai Tangen
We Study Billionaires - The Investor’s Podcast Network
January 14, 2026

BTC257: Bitcoin Mastermind Q1 2026 w/ Jeff Ross, Joe Carlasare, and American HODL (Bitcoin Podcast)

We Study Billionaires - The Investor’s Podcast Network
Uncensored CMO
January 14, 2026

Rory Sutherland on why luck beats logic in marketing

Uncensored CMO
Moonshots with Peter Diamandis
January 13, 2026

Tony Robbins on Overcoming Job Loss, Purposelessness & The Coming AI Disruption | 222

Moonshots with Peter Diamandis
Swipe to navigate