People vs Algorithms

The Substack Conundrum

48 snips
Jun 27, 2025
Dive into the complexities of building brands on platforms like Substack, as the hosts dissect its business model and user engagement challenges. The conversation highlights the disconnection of AI in the media landscape and regulations surrounding it. They also explore evolving sports media economics, including private equity's role and rising interest in women's sports. With engaging anecdotes from travels in Europe, listeners get a taste of cultural contrasts and culinary delights!
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INSIGHT

Substack's Brand-Value Paradox

  • The better a Substack writer is as a personal brand, the harder it is to sell the business detached from themselves.
  • Real enterprise value requires building a brand distinct from the individual and additional products like advertising.
ADVICE

Building Lasting Media Brands

  • Build a subscription base to create a resilient media business with enterprise value.
  • Develop a brand alongside the individual to mitigate key-person risk and allow scaling.
INSIGHT

Subscription Revenue Isn't Enough

  • Many successful Substackers generate $1-4 million/year, but that is not yet a 'real business'.
  • Sustainable business growth requires expanding beyond niche revenue into varied products and services.
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