The Gambler Story: When on the Growth Scale Do You Sell?

“Kenny Rogers had it right. You gotta know when to hold ‘em, know when to fold ‘em, know when to walk away and know when to run. That’s great advice for gamblers, and for entrepreneurs. For me now, it’s time to fold ‘em and walk away.” Ross (not his real name) didn’t strike me as the type who would listen to country music. Born and raised in the Northeast, he came to Nashville when his wife took a corporate role Read More

The Earn Out: Painful Stretching to Make a Shaky Deal

“Will I have to take an earn out when I sell my business?” Drew (not his real name) was ready to sell his company but he was scared. “I hear horror stories about business owners selling on an earn out which ends up not being paid. I can’t afford to let that happen.” Not one to mince words, I decided to level with him. “Drew, a good business with a reasonable valuation represented by a capable intermediary will Read More

Plan B: When the Partnership Goes South

“What’s worse, a partnership that goes bad after a few years or after just a few months?” Landon (not his real name) was almost in tears. “Before the launch, it seemed we were on the same page, but it wasn’t a matter of weeks before I could sense we had a different vision. I feel like such a failure.” Sitting at Starbucks with a man who’s about to cry is a bit awkward. I felt terrible, too, not having pithy advice Read More

Entrepreneurial Hubris

Three days after I told him I might be interested in their offer to buy my company, I was sitting across a table from them. We were in a posh conference room at the Loews Vanderbilt Hotel in Nashville. It was one of me, and four of them. They had been calling for the past few months expressing interest in acquiring my business. The publicly-traded company was growing through acquisition, it was just a matter of Read More

An Affair is Always a Bad Idea

Randy (not his real name) was about to make a life-altering decision. He had a need, and he wanted to fulfill it. The long term consequences were of less concern than getting what he wanted, right now. He called me, I suppose, wanting me to tell him it was a good idea. But with years of experience advising men and women in this situation, all I could do was tell Randy the truth from my heart. “Bringing in a Read More

September 12, The Day After

Today is the day after September 11, another day that will live in infamy. Ironic that September 11 this year came on the day after Hurricane Irma created historic havoc in my adopted home state of Florida, and one week after unbelievable hurricane devastation in Houston. It seems appropriate today to stop and remember those incredible first responders who go into the face of danger during the hurricanes, be it Read More

Indifference as a Style of Negotiation

“They have called several times over the past 18 months. Their offer is getting closer to what I want for the company.” Tom (not his real name) called me on the recommendation of his sister who I knew from church. He owns a medical services company that he started in 2005. The company has been profitable from its second year of operation, but the past three years the company has been growing at double-digit Read More

Key Question When Raising Equity: “If This, Then What?”

“I need $1,500,000 to open a new distribution center in North Carolina. It's a home run idea, but how much equity will I have to give up to raise that much?” Johnny (not his real name) and I have been good friends for seven years. We see each other socially several times a year, and once every 5 or 6 months we sit down to a serious conversation about his growing and vibrant medical supply business. “If I ever sell Read More

Buying a Business, the Downside(s) of Low Interest Rates

“I’m looking to buy a business, but I'm having the devil of a time doing it. Can you help?” Frank (not his real name) sold his profitable medical supply company two years ago, and is eager to get back to creating value through business ownership. He doesn’t have to work, the money he put in the bank after the sale of his company provides more than enough to take care of his family. But just 42-years old, Frank said Read More

A Funeral, Fried Chicken and Valuable Lesson

Little did I know I'd learn something at a funeral to help me appreciate an important lesson regarding the successful sale of a professional services business. I had returned to Orlando, where I spent the first half of my business career, to attend the funeral of a dear family member. After the funeral, the church hosted a covered dish dinner for family and friends. While going through the food line, I bumped into Read More