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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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In this episode, Jordan Ross unpacks how he scaled his holding company to $13 million in annual revenue — and why he intentionally scaled it back to $5 million to regain clarity, control, and profitability.
He breaks down the biggest lessons learned in hiring, equity structuring, and partnership dynamics that every agency owner should understand. Whether you’re building a single business or managing multiple ventures, these insights will help you avoid common pitfalls and scale with precision.
⏱️ Chapters
00:00 – Building a $13M Holding Company
02:03 – Why A+ Talent Changes Everything
03:28 – Hiring and Scaling With Intention
04:38 – Date Before Marriage: Partnership Timing
06:30 – The True Value of Equity
09:49 – Vesting Schedules That Prevent Regret
11:20 – Defining Ownership in Complex Structures
12:40 – Why You Should Pay As You Go
14:23 – Revenue Share Benchmarks That Work
To learn more go to 8figureagency.co
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