Kenny Rogers, in his song The Gambler, shares advice that works at the poker table and in business: “You’ve got to know when to hold ’em, know when to fold ’em, Know when to walk away, and know when to run.”
I heard it on the radio recently and it brought back a few business scenarios I’ve lived through—around a catering deal, selling our business, and our early days looking to buy or start a small business.
This column is more personal than usual. It’s about experiences that shaped how I evaluate deals—when to pursue them and when to walk away. It’s always hard to second-guess decisions. Even when the outcome wasn’t “great,” it may have been the best of several difficult options. My hope is that these stories help you look at your own business ventures and avoid getting overly excited about a deal when the warning signs are right in front of you.
You might even want to listen to The Gambler before reading on, just to get in the right frame of mind:
1) Know when you walk away – When we first started looking at small business ownership, it felt like we looked forever—and walked away from a lot of opportunities. Sometimes it was simple fear of committing without enough information. Other times, the red flags were obvious.
One that stands out was a small fast-food style establishment. The owner wanted to stay involved after the sale. When we visited, instead of cleaning the kitchen floor, they had laid cardboard over it. That was a deal breaker.
For me, the first conversation would have had to be about cleanliness. If someone believes they’re running a “successful” business and that’s their standard, how do you even begin to address that? It felt like they wanted a committed worker, not a true owner or partner.
Another example was a local coffee shop. Great product, great atmosphere. The problem? The books showed it was losing money. The broker tried to convince us it was actually profitable because the owner was buying groceries and other personal items through the business. Maybe it was a cash cow—but when the foundation isn’t trustworthy, how can you trust anything else?
Sometimes “walk away” is the smartest move you can make.
2) Know when to run – We once had a large catering “opportunity” for a publicly traded corporation. As we talked through the number of people we’d be feeding, the dollar signs started dancing in my head. Then they dropped the bombshell: Feed everyone lunch—including beverages and desserts and stay on site to serve —for about $3 per person. They suggested we treat it as “marketing costs.” I’ve been to many corporate catered events. No matter how good the food was, unless the location was extremely convenient, I rarely went to that restaurant afterward. So calling it “marketing” didn’t make sense.
They had other caterers lined up and ready to pounce. We chose to run away. Unfortunately, one of our competitors jumped at the opportunity and soon after closed. I don’t know if that deal alone caused it, but it was clearly a poor business decision. If you can’t even cover your expenses, it’s not a great deal—no matter how big the client’s name is. That’s why looking closely at every situation is critical.
3) Never count your money when sitting at the table – When we sold our restaurants, they were profitable. We never imagined that what we’d built over 10 years would disappear in 10 months. As part of the sale, we provided owner financing and factored those payments into our monthly cash flow. When those payments unexpectedly stopped and the new owner had health issues and went bankrupt, that scenario wasn’t in our “what could go wrong” list.
We had essentially counted the money while we were still sitting at the table. I learned more than I ever wanted to about repossessing assets and working with landlords. It was a painful reminder that a deal isn’t done until it’s truly done—and that risk doesn’t end at the closing table.
Think through
If you can bucket your “no” decisions into these three categories—walk away, run, and don’t count your money too early—it makes the “yes” decisions much easier. Don’t fall into the trap of saying “no” to everything until you have perfect information. Ask yourself:
Do I have more than 51% of the data I need to say this seems reasonable? Are the fundamentals sound—profitability, integrity, and alignment with my values?The examples above are meant to spur your thinking and maybe prompt you to revisit decisions you’ve made. How did they turn out? What would you do differently next time? Do you know when to walk away, and when to run?
Gregory Woloszczuk is an entrepreneur and experienced tech executive that helps small business owners grow their top and bottom line. Gregory believes in straight talk and helping others see things they need to see but may not want to with a focus on taking responsibly for one’s own business. He and his wife, Maureen, started GMW Carolina in 2006.
Chapelboro.com does not charge subscription fees, and you can directly support our efforts in local journalism here. Want more of what you see on Chapelboro? Let us bring free local news and community information to you by signing up for our newsletter.
Small Business, Big Lessons® — Know When to Walk Away, Know When to Run Chapelboro.com.
Hence then, the article about small business big lessons know when to walk away know when to run was published today ( ) and is available on chapelboro ( Middle East ) The editorial team at PressBee has edited and verified it, and it may have been modified, fully republished, or quoted. You can read and follow the updates of this news or article from its original source.
Read More Details
Finally We wish PressBee provided you with enough information of ( Small Business, Big Lessons® — Know When to Walk Away, Know When to Run )
Also on site :
- In 1974, three artists buried 10 Cadillacs nose-first in an Amarillo, Texas wheat field; the row was moved 2 miles west in 1997 as the city grew
- In 1987, Jim Reinders built a 96-foot circle of 39 cars in a Nebraska field as a memorial to his father; an estimated 4,000 people later watched an eclipse from it
- Ryde Group Ltd. Sued for Securities Law Violations - Contact the DJS Law Group to Discuss Your Rights - RYDE