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Are you trying to grow your business by 10% year over year? You might be leaving massive wealth on the table. In this episode, we sit down with Tom Shipley, a former Special Forces operator turned serial entrepreneur and aggressive investor. Tom challenges the traditional startup narrative with a shocking reality: Growing organically might increase your value by 50% over five years, but buying competitors can increase it by 1,200%. Tom shares his incredible journey from the dot-com bust, where he was days away from missing payroll, to buying a $15M division of Boise Cascade without using his own capital. We unpack the "Programmatic M&A" playbook, how to use acquisitions to solve operational weaknesses, and why the best path to a massive exit is often buying your way there.
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Tom Shipley is a serial entrepreneur and M&A strategist known for creating the “Add a Zero” growth philosophy, which helps founders rapidly scale their businesses through strategic acquisitions. From his early career as an IDF special forces operator to building and advising brands that have generated more than $2 billion in revenue, Tom brings a rare combination of disciplined execution and bold dealmaking. A pioneer of programmatic M&A for mid-market companies, he has raised over $100 million, led multiple acquisition platforms, and now teaches 7 to 9 figure founders how to accelerate growth, close capability gaps, and engineer premium exits through smart, repeatable deals.
Websites - https://www.tshipley.com/
- https://dealconlive.com/
LinkedIn - https://www.linkedin.com/in/t-shipley/
Time Stamps:
00:00 - Intro
02:47 - Buying a division of a Fortune 500 company without cash
05:05 - Scaling a beauty brand from $30k to $100M+ via acquisition
08:09 - How Mezzanine debt works (and why it’s better than pure equity)
12:51 - The Golden Stat: 50% vs. 1,200% Enterprise Value growth
17:58 - The thought exercise that will force you to raise your prices today
20:41 - The biggest mistakes entrepreneurs make when selling
24:14 - Why "Day One" after closing is the most dangerous time
27:31 - What is Programmatic M&A?
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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/
