This Week in Startups
This Week in Startups

How to Raise a Seed Round in 2026: Ask Jason | E2294

May 29, 2026

AI Summary

5 min read

🎙️ The Speakers & Context

  • The Format: Host discussion with audience Q&A.
  • The Key Players:
    • Jason Calacanis: Host of This Week in Startups, angel investor, and founder of the Launch Accelerator. He provides the primary strategic and investment insights.
    • Lon Harris: Co-host, who vets and presents questions from the audience, acting as a foil for Jason's opinions.
  • The Vibe: Reflective, pragmatic, and occasionally combative. Jason blends hard-won operational advice with candid, personal takes on industry figures.

🎣 The Executive Hook

  • The "One Big Idea": The cost and time to reach product-market fit have collapsed from years and millions of dollars to weeks and a few thousand dollars. This seismic shift means the primary moat for startups is no longer capital or technology, but the ability to build community, workflow, and high-touch services around a commoditized AI core.
  • Why It Matters: This democratization of creation is a direct consequence of the AI and cloud revolution. It forces a strategic pivot: founders must stop fearing being "wrapped" by frontier labs and instead focus on the "multiplayer mode" and "human-in-the-loop" experiences that large language models (LLMs) will never natively provide.

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What you'll learn

  • 1 (00:00) **🎙️ Introduction: Jason Calacanis & Lon Harris**
  • 2 (03:06) **Advice for an "Too Early" Startup with Investor Interest**
  • 3 (08:05) **The Idea of a "Founder Community College"**
  • 4 (18:10) **How Startup Evaluation Has Changed in 10 Years**
  • 5 (23:22) **Differentiating Your Startup from Frontier AI Labs**
  • 6 (29:25) **Finding the Right Investor: Beyond Stage & Sector**
  • 7 (37:14) **Path for a Bootstrap Hardware Founder**

+ Full timestamped outline available in the app

Show Notes

This Week In Startups is made possible by:


partner 1 - link

partner 2 - link

partner 3 - link


Today’s show:

Jason breaks down the real math behind raising a seed round. Here’s the funnel: contact 150 firms, get 50 first meetings, convert 2o into second meetings, and close 2 term sheets.

PLUS Jason responds to viewer questions about why hardware is no longer a dirty word for investors, how to differentiate your startup from frontier-model companies like OpenAI, even when they’re in your niche. Plus a pitch for “Founder Community College,” and anecdotes from Lon’s European odyssey.


Thanks for the Questions:


Richard Corral: CEO of Quanto: https://quanto.co/

ØnProtons on X: https://x.com/0nProtons

SergeDawg on X: https://x.com/sergedawg

Mahika Golani

Peridot: https://www.tryperidot.com/

Shawn Sully on X: https://x.com/aroogle

Programs and Accelerators Mentioned:

Y Combinator: https://www.ycombinator.com/

Techstars: https://www.techstars.com/

Antler: https://www.antler.co/

PearX: https://pear.vc/pearx/

Sequoia ARC: https://www.sequoiacap.com/arc/

Kauffman Fellows: https://www.kauffmanfellows.org/

Companies and Startups Referenced:

Whoop: https://www.whoop.com/

Knightscope: https://knightscope.com/

Eight Sleep: https://www.eightsleep.com/

Cafe X: https://www.cafexapp.com/


Media Referenced:


New Yorker Sam Altman profile:

This Week in Startups