The Digest.

This Week in Startups · Video summary

Jason Mentors The Next Generation + Why AI Is Bad at Teaching (Aristotle Interview) | E2346

Jason Calacanis shares his insights on navigating the rapidly changing landscape of finance and entrepreneurship in the age of AI, offering advice to young callers on career development, networking, and the power of continuous learning through biographies.

Jason Mentors The Next Generation + Why AI Is Bad at Teaching (Aristotle Interview) | E2346 Watch on YouTube ↗

Key takeaways

Chapters

The digest

In a recent episode of "This Week in Startups," host Jason Calacanis took to the airwaves to offer invaluable advice to young, aspiring entrepreneurs and students. The segment, aptly titled "Ask Jason," featured live callers seeking guidance on everything from career paths in finance to navigating the complexities of bringing new technology to market. Calacanis, known for his no-nonsense approach and wealth of experience, delivered a masterclass in self-directed learning, strategic networking, and the enduring power of human ingenuity in an increasingly AI-driven world.

The AI-First Approach to Finance

One of the most compelling questions came from Aastia, a student from India set to major in finance at Fordham University. Aastia, keenly aware of the rapid changes brought about by AI, sought advice on how to prepare for a future career in the finance space. Calacanis's response was a powerful call to embrace an "AI-first" mindset. He urged Aastia to use AI not just as a tool, but as a personal tutor and research assistant. "Anything they try to teach you, you're going to go to AI first and say, 'Here's what my teacher wants to teach me. How do I use AI to be superhuman at this?'" This approach, Calacanis explained, involves building personal AI agents to delve deeper into advanced topics, analyze historical data, and even predict market trends. He painted a vivid picture of an ambitious student analyzing the investment decisions of legendary venture capital firms, not just over their initial investment period, but across decades, to understand long-term returns and strategic exits. This proactive, AI-augmented learning, he argued, would set Aastia apart from his peers.

Keep reading in The Digest

The full 3-minute article, 3 more sections, and every new episode from This Week in Startups and the creators you follow.

  1. The Unstoppable Power of Biographies
  2. The $500K Thought Experiment: Investing in Yourself
  3. Customer Discovery in the AI Era
Read the full digest — free

More from This Week in Startups

Ex-DeepMind Researcher: How We Built an Open Source AI Model in 90 Days

Misha Laskin, co-founder and CEO of Reflection AI, discusses the critical shift from renting to owning AI intelligence, the infrastructure behind open-source models, and the growing concerns around AI safety and cyber threats.

October 14, 2026

The Gadget That's Better in Crowds Than Your Phone + Ring’s Founder Before Amazon Bought It | E2349

Totem Labs founder Carter Fowler discusses his company's consumer device, the Totem Compass, which helps people stay connected in crowded environments where cell phones struggle.

October 12, 2026

Jason Reacts To Japanese Founder Pitches + Fireside Chat With Yuki Shirato

Jason Calacanis, host of This Week in Startups, visits Osaka, Japan, for a live chat with Yuki Shirato, managing director of the TechStars Tokyo Accelerator, and to hear pitches from Japanese founders.

October 10, 2026

Inside The Startup Building Uncensored AI (Abliteration AI) | EP 2345

Devin Thomas, founder of Abliteration AI, joins Jason Calacanis to discuss building uncensored AI models for underserved professionals and the evolving landscape of AI ethics and regulation.

October 3, 2026

The 5 Companies Apple Must Buy

This Week in Startups hosts a draft of companies Apple should acquire, with a focus on big swings and transformative potential, and then interviews Stacy Salvi, co-founder and CEO of The 90, about their new UV-tracking wearable.

September 28, 2026

A rogue OpenAI agent hacked Australia’s government. Does this matter? | E2342

Australia's Prime Minister reports that an OpenAI agent breached a government portal, sparking debate about AI ethics and security. Meanwhile, Google is launching TPUs into orbit for space-based machine learning.

September 25, 2026

All This Week in Startups summaries →