Building Billions with Brandon Dawson

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S2 EP 28 The Brutal Truth About Why 97% of Business Owners Never Reach $100 Million

June 29, 2026

Everybody says they want to build a $100 million business, but very few are willing to become the leader it actually requires. In this episode of Building Billions, I break down the mindset shifts that separate founders who stay stuck from those who build real enterprise value. I share why most businesses stall at $3 million, how your personal leadership determines your company's ceiling, and why the habits that got you here won't get you where you want to go. I also dive into the hard realit...

S2 EP 27 Building Billions with JD Ross: Inside the Playbook Behind Multi-Billion Dollar Companies

June 23, 2026

In this episode of Building Billions, I sit down with JD Ross, founder of Opendoor, partner at Atomic Ventures, and founder of WithCoverage, to break down how he’s taken companies from idea to billions in enterprise value, including scaling Opendoor from first revenue to an $8B public company in under six years. We get into what actually drives growth at scale, how to understand your business equation, why companies break as they expand, and what it really takes to build and lead teams ...

S2 EP 26 The $5 Trillion Opportunity Hiding in “Boring” Businesses

May 28, 2026

In this episode of Building Billions, I break down why the biggest wealth creation opportunity right now isn’t in flashy tech or the next viral app, it’s in boring, traditional small businesses. From HVAC and garage doors to storage units and car washes, I explain how consistent cash flow, operational improvement, and smarter systems can turn overlooked businesses into high-value enterprises. We also dive into the “silver tsunami” of aging business owners, where trilli...