Business Lunch

The Bottlenecks Billionaire Playbook: How the World’s Richest Build, Scale, and Keep Their Fortunes

Oct 16, 2025
Discover the playbooks billionaires use to thrive! Explore how distribution, not just technology, drives real enterprise value in a world where AI makes innovation easy to copy. Learn about Qualified Small Business Stock exemptions that can save millions in capital gains taxes. Hear insights on the potential of 'boring' businesses like logistics and energy to create lasting wealth. Delve into capital cycling strategies employed by top investors and why scalable brands and community-driven marketplaces are today's gold mines.
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INSIGHT

Users, Not Code, Create Moats

  • Technology alone is no longer a durable moat because AI makes product features easy to copy.
  • Ownership of large user bases and distribution creates real enterprise value that acquirers pay for.
ADVICE

Use QSBS Before An Exit

  • Structure and hold eligible C-corp stock for five years to leverage QSBS and potentially exclude up to $10M gain per shareholder.
  • Combine QSBS with charitable moves like DAFs to legally minimize capital gains and retain more proceeds.
ADVICE

Don't Overcomplicate Taxes Too Early

  • Avoid overcomplicated tax schemes until you reach meaningful scale; aim for clarity and simplicity.
  • Consider serious restructuring only when net worth approaches roughly $10M to justify complexity and costs.
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