Episode 247

The Exit That Never Happened: Turning a Family Failure Into a Mission to Help Founders Exit Right with Ben Brickweg

What happens when an eight-figure exit falls apart?

For Ben Brickweg, it sparked a decades-long mission to ensure no other founder has to experience the same heartbreak his family did.

In the latest episode of The Exit, Ben — founder of Exitworthy, attorney, and seasoned M&A advisor — pulls back the curtain on what really goes wrong in business exits… and how to fix it.

What You’ll Learn:

  • The family deal that blew up and why it changed Ben’s life forever
  • How Ben accidentally fell into M&A and worked on 200+ deals his first year
  • Why most founders are unprepared to exit — and how to change that
  • The three-part “Value Mountain” framework: Valuation, Sellability, and Transferability
  • The biggest legal mistakes business owners make when selling
  • Why private equity offers often shift post-LOI — and what to do about it
  • How lifestyle inflation and poor financial planning derail more exits than you’d think
  • What it really means to build an “exit-worthy” business

Ben doesn’t just talk theory. He’s been on every side of the table — founder, lawyer, broker, buyer — and he’s seen deals thrive, collapse, and quietly destroy the dreams of unprepared sellers.

His advice?

Don’t wait until you’re ready to sell. Build your business like you’re going to exit — from day one.

This is a no-BS, deeply practical episode for anyone who owns a business and wants optionality — whether that means exiting now, or 10 years from now.

Personal &/or Company Bio:

Ben Brickweg has worked with over 2,000 business owners, helping them grow, protect, and sell their companies the right way. He runs two companies, Sagewood Business Advisors and Lodgepole Law, both built to help business owners navigate complex deals and legal challenges. Sagewood Business Advisors is a boutique M&A firm that helps owners understand their value, structure strong deals, and exit on their terms. Lodgepole Law is a provider of fractional general counsel services for acquisition entrepreneurs who need a proactive legal strategy, not last-minute chaos and hourly meters. He is also the creator of Exit Worthy, a platform that includes the podcast, training materials, and resources to help business owners get serious about preparing for a real exit; and Business Legal Fortress, bridging the gap between legal template stores and full-service firms, giving business owners affordable, effective legal protection without the unpredictability of hourly fees.


Ben on LinkedIn: https://www.linkedin.com/in/benbrickweg/

Website:

https://gosagewood.com/

https://exitworthy.com/

https://lodgepolelaw.com/ 

YOUR HOST

Steve McGarry

An entrepreneur, content creator, and investor based in sunny Tampa, Florida. In 2015, while living in San Francisco, Steve sold his first fintech startup LendLayer to Max Levchin’s (founder of PayPal) consumer finance company Affirm.

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