Multiple Million-Dollar Exits: Jeremy Schoemaker on Building, Scaling, and Knowing When to Sell

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What does it take to build and sell multiple successful businesses in less than a year? In this episode of The Exit, host Steve McGarry sits down with serial entrepreneur Jeremy Schoemaker, also known as ShoeMoney, to discuss his journey from selling appliances at Sears to building multimillion-dollar internet businesses and successfully navigating multiple exits.

Jeremy shares how a $130,000 Google AdSense check helped launch his entrepreneurial career, how his advertising platform Auction Ads attracted acquisition interest from eBay just months after launching, and how he scaled another business to nearly $1 million in monthly revenue before selling it. He and Steve explore the importance of preparing a business for acquisition, prioritizing user growth over immediate profitability, identifying the right time to sell, and understanding what makes a company attractive to buyers. Jeremy also reveals why he once sold a business for potentially one-tenth of what a buyer was willing to pay, the costly lessons he learned from passion projects, and how he's applying his entrepreneurial playbook to artificial intelligence today.

Jeremy’s LinkedIn - https://www.linkedin.com/in/shoemoney/

ShoeMoney Website - https://shoemoney.com/

Jeremy’s Instagram - https://www.instagram.com/shoemoney4real/

Steve’s LinkedIn - https://www.linkedin.com/in/thestevemcgarry/


Key Chapters:
00:00 Episode Introduction
04:04 Jeremy Schoemaker's Background and Early Days
06:08 Building a Business and First Exits
09:57 Preparing Your Business for Sale
12:53 Timing the Exit and Personal Insights
16:59 Valuation Drivers and Strategic Assets
20:07 The PAR Program and Business Growth
22:56 Maximizing Business Value for Sale
27:19 Lessons from Mistakes and Passion Projects
31:18 Advice to Jeremy 10 Years Ago
34:01 Current Projects and Future Plans


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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/