The Secret to a Multi-Billion Dollar Exit (And Why You’re Doing It Wrong) with Mike Bennett

Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business, and you’ll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: https://flippa.com/exit -- Are you running your business to scale, or are you running it to sell? According to Michael Bennett, managing partner and founder of Crew Capital, you should always be doing both. In this tactical episode of The Exit, Michael sits down with Steve McGarry to break down the exact playbook for preparing your business for a massive payday long before you ever want to hand over the keys. From tracking the 10 to 20 industry KPIs that actually matter to navigating the complex world of QSBS tax benefits and succession planning, Michael shares the hard-earned wisdom he used to help guide one client from a $50M enterprise value all the way to a public, multi-billion-dollar powerhouse. Drawing from years of investment banking and advising founder-led companies, Michael shares why the best time to prepare for an exit is before you need capital and how running your company as if it is always “sale ready” can dramatically increase enterprise value. Michael also breaks down the biggest mistakes founders make when preparing for a sale, why timing matters more than most entrepreneurs realize, and how market conditions can impact valuation multiples. Steve and Michael dive into minority deals, partial exits, rollover equity, and the difference between maximizing value versus defining personal success. Whether you are years away from selling or actively considering an exit, this conversation offers tactical advice to help you prepare smarter and avoid painful surprises. -- Michael Bennett is the Managing Partner of Crewe Capital and Co Founding Partner of Crewe Advisors, where he helps founder led and closely held businesses navigate mergers and acquisitions, capital raises, and long term financial strategy. Over the past 20 years, Michael has advised on more than 100 investment banking transactions while helping grow Crewe into a multi faceted financial platform overseeing more than $3 billion in assets. After overcoming an unstable childhood and putting himself through school, Michael built the firm from the ground up, starting with no clients and a single $20,000 retainer, eventually expanding into wealth management, alternative investments, philanthropy, and community initiatives. Website - https://crewecup.com/ LinkedIn - https://www.linkedin.com/in/crewecapital/ KEY TIMESTAMPS: [00:01] Introduction to Michael Bennett and His Journey [05:49] Preparing for an Exit: Timing and Strategy [08:58] Common Mistakes in Exit Preparation [11:48] Understanding Valuations and Market Trends [14:50] Defining the Right Time to Exit [17:46] Exploring Partial Exits and Deal Structures [20:46] Favorite Deals and Lessons Learned [23:41] Advice for Future Entrepreneurs [26:56] Conclusion and Overview of Crewe Capital -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/