The Greatness Machine 359 | Ryan Begelman (Part 2) | What It Really Takes to Step Away from Your Company Without Regret
What if selling your company didn’t mean letting go—but leveling up, on your terms?
In this episode of The Greatness Machine, Ryan Begelman returns for part two to share the behind-the-scenes story of how he scaled, sold, and systematized a company—without losing his sense of joy.
From building a business with friends to generating millions in additional value by taking the exit process into his own hands, Ryan unpacks how thoughtful planning, operational excellence, and self-education made all the difference. He shares why most founders leave money on the table during a sale, how he trained his COO to take over, and the surprising reason he almost didn’t want to sell.
In this episode, Darius and Ryan will discuss:
(00:00) Introduction and Recap of Previous Episode
(03:00) The Journey of Bisnow Media
(06:09) Acquisition Entrepreneurship and Bootstrapping
(09:00) The Role of AI in Business
(12:12) Navigating Multiple Ventures
(15:09) The Summit and Powder Mountain Experience
(18:07) Challenges of Managing Multiple Businesses
(21:10) The Future of Powder Mountain and Lessons Learned
(31:20) The Journey of Acquiring Powder Mountain
(32:38) Lessons Learned from Past Experiences
(35:46) Building Bisnow: Growth and Strategy
(39:13) The Exit Strategy: Selling Bisnow
(48:10) The Joy of Entrepreneurship and Life Design
Ryan Begelman is an executive coach, entrepreneur, and investor. As CEO of Bisnow Media, he grew the company from $1 million to $20 million in revenue before its sale in 2016. He co-founded Summit, described by Forbes as “The Davos of Generation Y,” and has invested in startups like Uber, Warby Parker, and Coinbase. A mindfulness practitioner based in NYC, Ryan is passionate about cycling, cooking, and lifelong learning.
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Connect with Ryan:
Website: https://www.ryanbegelman.com/
LinkedIn: https://www.linkedin.com/in/ryanbegelman
Instagram: https://www.instagram.com/ryanbegelman/
Email: ryan.begelman@gmail.com
Connect with Darius:
Website: https://therealdarius.com/
Linkedin: https://www.linkedin.com/in/dariusmirshahzadeh/
Instagram: https://www.instagram.com/imthedarius/
YouTube: https://therealdarius.com/youtube
Book: The Core Value Equation https://www.amazon.com/Core-Value-Equation-Framework-Limitless/dp/1544506708
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