This Week in Startups
This Week in Startups
Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world’s greatest founders, operators, investors, and innovators.
Jason Calacanis
PodcastAI
PodcastAI

Inside Substack’s $100M Push to Fend Off Beehiiv | E2153

Jul 18, 2025 • 73 mins

WHY DOES @SUBSTACKINC NEED $100M IN NEW FUNDING? HOW DO THEY PLAN TO STAY AHEAD OF @BEEHIIV? Jason and Alex are debating the future of indie publishing on an all-new TWiST, considering the future of these rival platforms, plus Patreon and more. PLUS they’re digging into Lovable’s latest raise and what it says about the current economics of vibecoding, surveying the automated driving landscape in light of Uber’s new agreement Lucid and Euro, explaining Jason’s “meme processing” theory of internet humor, AND looking ahead to Christopher Nolan’s IMAX epic “The Odyssey.” Join us for the longest-running and most in-depth podcast on Earth for startup founders.

Key Points

  • The "graduation problem" refers to businesses like EHarmony that lose customers when they successfully solve their core problem, such as finding a life partner.
  • Substack's recent $100 million funding round at a $1.1 billion valuation highlights its growth strategy, including expanding into advertising to complement its subscription revenue.
  • The rise of AI and coding assistants like Lovable, backed by significant funding, underscores the massive potential market for AI-driven tools, despite the competitive landscape with foundational model companies.
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Speakers

Jason Calacanis

Host • 76%

Alex Wilhelm

Host • 19%

Lon Harris

Guest • 5%

Partners

Lemon.io

Transcript

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