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The 8-Figure Trigger


About this episode


Lee Gregory built Sir Lines-A-Lot, a company that paints lines on highways, to 40 employees. It was blue-collar work, so when Gregory learned his company could be worth north of eight figures, he decided it was time to sell. During this interview, Gregory drops dozens of knowledge bombs for aspiring value builders including:

Hang On To Your Equity: painting highway lines requires trucks that can cost upwards of $700,000. Instead of borrowing money to buy a new one or soliciting outside investment to fund his equipment needs, Gregory bought used trucks for as little as $60,000. Bootstrapping allowed Gregory to hang on to 100% of his business and avoid significant debt.

Do Your Pre-diligence: pre-diligence is answering the questions you’re likely to get during diligence before you go to the market. If Gregory had one thing he would have done differently, it would have been getting all of his books in order before soliciting bids.

You-proof your company: once Gregory decided to prepare his business to sell, he brought in a general manager to oversee the business’s day-to-day operations. This hire ensured his business wasn’t dependent on him.

You’ll get lots of other nuggets in this interview including:

  • how to calculate “add-backs” (they could add serious money to your take from a sale)
  • why writing a list of opportunities you haven’t pursued could be as valuable as the ones you have
  • how to get hundreds of private equity buyers interested in your business
  • how job costing can come back to bite you
  • the value of the strategic walk away (and how to muster the courage to employ this negotiating tactic)

Gregory credits his advisor for first turning him on to the value he had created and then for shepherding the sale process through to dozens of offers, including an eight-figure winner. If you’re looking for an advisor to help you maximize your business value, consider talking with a Certified Value Builder™ .

Check out our article on The Acquisition Entrepreneur.

Check out our full M&A Glossary

About Our Guest

Lee Gregory grew up in an Entrepreneurial family and loves all things business. It was this passion for entrepreneurship that prompted Lee to leave the corporate world and start his own company in 2005. Lee founded Sir Lines-A-Lot (, a parking lot and highway paint striping business. What started out as a part-time operation with a used paint machine and an old pickup truck, turned into a multi-million dollar, statewide company with a great reputation, and an EBIDTA profile that many PE firms look for.

As Gregory’s schedule and work demands increased he decided it was the right time to step away from his role and sell while the PE market was strong. He did so and then took the next 6 months off to travel the world with his wife and 3 children. After the much-needed break Lee re-entered the industry and became an Operating Partner for the PE firm that acquired Sir Lines-A-Lot. For the past two years, Gregory has been on the other side of the M+A table and has helped evaluate and acquire other companies in the industry.

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