Bob Fox
How Bob Fox Helps Entrepreneurs Buy Smart, Avoid Bad Deals, and Build Real Ownership
Why disciplined due diligence beats “buy something fast” every time
Bob Fox planned to become a lawyer—until a finance class changed everything and launched him into a Wall Street career built on cold calling. After leaving Paine Webber without a clear plan, Bob spent two difficult years trying to buy a business, then turned that frustration into a career helping others buy and sell small businesses—and evaluate oil & gas opportunities with real-world due diligence.
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About This Episode
Bob Fox’s path into entrepreneurship didn’t start with a perfectly mapped strategy. He left a demanding finance role and assumed buying a business would be straightforward—until he ran into the reality: inconsistent numbers, misleading sellers, and deals that simply didn’t hold up under scrutiny.
Rather than rushing into the wrong acquisition, Bob pivoted. He became a business broker focused on helping buyers find businesses that are actually worth owning—typically in the $250K to $2M range. He breaks down what makes a small business viable, why cash buyers reduce deal risk, and how discretion matters when employees don’t know a sale is happening.
Bob also shares how he expanded into oil & gas deals—carefully—by learning from a veteran investor with decades of experience. The throughline is clear: mentorship and pattern recognition protect entrepreneurs from expensive mistakes.
For founders and buyers, this episode is a grounded look at entrepreneurship through ownership: how to evaluate opportunities, how to think about risk, and why the “right” business matters more than getting into a business quickly.
Key Insights
Don’t quit your job without a clear acquisition plan and realistic timeline.
Buying a business is often harder than starting one—misleading listings are common.
Don’t rush: the first “good-looking” deal is rarely the best deal.
Industry fit matters—buying a business you don’t like creates fast regret and forced resales.
Liquidity matters: buying with too little cash leaves no margin for operational surprises.
Discretion is operational strategy—staff panic can damage value before closing.
Prefer cleaner structures: cash offers reduce post-close risk, renegotiations, and fallout.
In oil & gas, the operator matters as much as the asset—learn to vet people, not just numbers.
Episode Transcript
This transcript has been lightly edited for clarity and readability. Filler words were removed, sentence structure improved, and formatting adjusted while preserving the original meaning and conversational tone.
Henry Harrison:
Welcome to Entrepreneurs, Business and Finance. Today we’re fortunate to have Mr. Bob Fox on the show.
Welcome, Bob. How are you?
Bob Fox:
Hi, Henry.
Henry Harrison:
Bob is out of New Jersey. He’s an entrepreneur, self-employed, and a family man.
Bob, how far do you live from where you grew up?
Bob Fox:
Probably about 50 miles south. We moved closer to the beach in New Jersey, and we love it.
Henry Harrison:
What’s not to love about the beach?
When you were a kid, did you think you’d be self-employed, or did you imagine working for a big company?
Bob Fox:
I always thought I’d be a lawyer—that was the plan until college.
At the last minute, I decided I didn’t want to be a lawyer and went into finance instead. I took a class, loved it, and that was it.
Henry Harrison:
Did you have an idea of what you wanted to do in finance?
Bob Fox:
No idea. I double-majored in finance and political science.
One day I saw an ad for a job at Paine Webber, went for an interview, and they liked my name. That’s probably the only reason I got the job.
Henry Harrison:
You’ve been in finance in one way or another your entire career.
Bob Fox:
That’s right.
And here’s something funny—when I started, the movie Wall Street had just come out. Charlie Sheen’s character was Bud Fox.
So when I’d call and say, “This is Bob Fox,” people thought I was saying “Bud Fox” and would hang up. Some even complained that someone from our firm was calling pretending to be the movie character.
Henry Harrison:
Those were the days of cold calling.
Bob Fox:
Exactly.
Low pay, long hours. I was cold calling 40–50 hours a week, and on weekends I worked at an appliance store selling TVs—and made more money there.
Henry Harrison:
What made you leave that path?
Bob Fox:
I got tired of it and wanted my own business.
Here’s advice: know what you’re going to do before you leave your job. I didn’t. I figured I’d just go buy a business.
It ended up being the hardest thing I’ve ever done—two years of looking at bad deals, people misrepresenting numbers, businesses that didn’t make sense.
Another key lesson: don’t rush. Take your time, and make sure you’re passionate about the industry.
Too many people buy something without knowing the business, then want out within months because they hate it.
Henry Harrison:
That had to be stressful.
Bob Fox:
It was.
Eventually, I decided to become a business broker—to help others buy and sell businesses and filter out the nonsense I had seen.
Some listings didn’t even make sense—showing profits higher than revenue.
Henry Harrison:
How do you find buyers and businesses?
Bob Fox:
Buyers are easy—they’re everywhere.
The hard part is finding a business worth buying.
The best opportunities are often mom-and-pop owners retiring after decades. You just have to keep looking until something real shows up.
Henry Harrison:
What types of businesses do you typically deal with?
Bob Fox:
Mostly small businesses:
Gas stations
Convenience stores
Restaurants
Liquor stores
Laundromats
Typically deals between $250,000 and $2 million. Larger deals get much more complex.
COVID hit small businesses hard, but restaurants have come back strong.
Henry Harrison:
How does your brokerage process work?
Bob Fox:
You sign the seller—preferably with an exclusive listing.
Discretion is critical. You don’t want employees finding out and leaving.
Showings are done off-hours, quietly, and carefully to avoid disruption.
Henry Harrison:
Deals can fall apart late in the process.
Bob Fox:
All the time.
Sellers want cash—it’s clean.
They don’t want to rely on payments over time because:
The buyer could walk away
The business could decline
They may already have relocated
Cash minimizes those risks.
Henry Harrison:
You’ve developed strong skills analyzing businesses.
Bob Fox:
Yes, and it’s not as complicated as people think.
There are basic formulas.
People tend to overvalue their businesses, but the market determines value.
A common baseline is about two times net profit plus assets—though it varies.
Henry Harrison:
You’ve also been involved in oil and gas investments.
Bob Fox:
Yes.
A friend introduced me when oil was around $40.
In smaller oil deals, investors buy percentage interests. You share risk and reward.
There are also tax advantages that encourage energy investment.
But it’s not simple—who you work with matters a lot.
Henry Harrison:
Mentorship seems to have played a big role for you.
Bob Fox:
Absolutely.
I learned from someone who had been in oil and gas for 40 years.
Too many people ignore experienced advice. If someone has that level of experience, you should listen.
Henry Harrison:
You’re also a big sports fan.
Bob Fox:
Huge fan—football, baseball, hockey, UFC.
My family has had New York Giants season tickets since 1959. It started because a championship game was blacked out locally, so they drove to Connecticut to watch it. After that, they bought season tickets—and we’ve had them ever since.
Henry Harrison:
Let’s wrap up with advice for entrepreneurs.
Bob Fox:
You can’t work 9-to-5 as an entrepreneur.
You have to be available.
I’ve seen people refuse calls at 5:05 because they’re “done for the day.” That’s a mistake.
My first business sale happened because I answered a call on a freezing Sunday night. Someone wanted to see a laundromat at 6:30 PM. I showed it—and he bought it.
Then he bought four more.
Most calls won’t turn into deals—but you never know which one will.
Henry Harrison:
That’s a great place to end.
Bob, thanks for coming on the show.
Bob Fox:
Have a great day.
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