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Season 3 - Episode 9

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.

Bob Fox on Henry Harrison Podcast

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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

Disclaimer: 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 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 I went into finance. I took a class, loved it, and that was it. Henry Harrison: Did you have an idea of what you’d 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 the only reason I got the job. Henry Harrison: You’ve been in finance in one way or another your whole 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. When I called and said, “This is Bob Fox,” people thought I was saying “Bud Fox” and they’d hang up. People complained that someone from our firm was calling pretending to be Bud Fox from the movie. Henry Harrison: Those were the days of cold calling. Bob Fox: Exactly. Paine Webber was cold calling—low pay, long hours. I worked weekends selling TVs at a place called Tops Appliances, and I made more money on weekends than I did cold calling 40–50 hours a week. Henry Harrison: What made you leave and shift away? Bob Fox: I got tired of it and had the urge to have 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. Henry, it was the hardest thing I’ve ever done. Two years of looking at nonsense—people lying about numbers, businesses that didn’t make sense. It’s not easy to find a good business. Another piece of advice: don’t rush. Take your time. And make sure you’re passionate about the industry. Too many people call and say, “I want a business, but I don’t know what industry.” They buy something, then five months later they want to resell it because they hate it. If you quit your job, buy a business, then decide you don’t like it, you’re stuck. Henry Harrison: That had to be stressful at home. Bob Fox: We couldn’t find anything to buy. That’s when I decided I’m going to be a business broker and help people buy and sell businesses—and weed through the nonsense. I’d see listings where a business supposedly made more profit than revenue. That’s hard to do, but that’s what some people put on paper. Henry Harrison: How do you find buyers, and how do you find businesses? Bob Fox: The easy part is finding buyers. They’re everywhere—tens of thousands in every state. The hard part is finding a business worth buying. The best sellers are often mom-and-pop owners retiring after 40 or 50 years. You keep looking and something shows up. Henry Harrison: What kinds of businesses do you typically see? Bob Fox: Gas stations, convenience stores, restaurants, liquor stores, laundromats—small businesses. Usually $250,000 to $2 million deals. Larger deals are more complex and most people can’t buy them. COVID was a disaster for small business. Big business did great, but small business was hit hard. Restaurants have really come back strong since then. Henry Harrison: How does your brokerage process work? Bob Fox: You sign the seller—the person selling the business. You want an exclusive listing so you’re the only broker handling it. A big part is discretion. You don’t want employees to know it’s for sale. That can create panic and turnover. You show off-hours, do it quietly, and make sure buyers don’t start poking around. Henry Harrison: Deal terms can get complicated. Bob Fox: A lot of deals fall apart at the last minute because someone changes terms. Ideally, sellers want an all-cash buyer. They don’t want payments over time—what if the buyer walks away, runs the business down, or you’re already moved to Florida? Cash makes it cleaner. Henry Harrison: You trained yourself to analyze businesses through that two-year search. Bob Fox: Yes. It’s not as hard as people think. There are general formulas. People always think their business is worth more than it is, but the market decides. You need realistic numbers. Don’t leave out expenses like employees. And don’t assume someone else will run it for you. Sometimes you should spend time watching the business—see if the story matches the reality. Henry Harrison: And you also have to be honest on valuations when you take listings. Bob Fox: Right. Some brokers promise the moon just to get the listing. But word gets around. You’re not going to sell it at that price. A common baseline is about two times net profit plus assets, though it varies by business. That’s a reasonable starting point. Henry Harrison: You also got into oil and gas deals. How did that happen? Bob Fox: A friend told me about it when oil was around $40. He explained how smaller oil projects are often funded—banks don’t always lend, so investors buy a percentage interest. You share the risk and reward. It’s an accessible way for people to speculate without needing huge capital. There are tax advantages too—those incentives exist to encourage energy development. Henry Harrison: But it’s not simple. Bob Fox: Not at all. I met a wealthy investor who’d been in oil and gas over 40 years. He taught me everything—how people hide money, what to look for, which operators are legitimate. If it wasn’t for him, I probably wouldn’t have done it. In oil and gas, it’s about who you’re dealing with as much as anything else. Henry Harrison: Mentorship and listening come up a lot in your story. Bob Fox: Too many people don’t recognize who they should listen to. If someone has been doing it for 40 years and knows the business inside and out, you should listen. At least hear them out. Henry Harrison: You’re also a sports fan. Bob Fox: Big time. Football, baseball, hockey, UFC. My family has had New York Giants season tickets since 1959. It started because the 1958 championship game was blacked out in New York, so they had to drive to Connecticut to watch it. After that, they bought season tickets and they’ve stayed in the family ever since. Henry Harrison: Any final advice for entrepreneurs? Bob Fox: You can’t work nine to five as an entrepreneur. You have to be available. I’ve seen people in sales refuse a call at 5:05 because they’re “done at five.” That’s crazy. My first business sale ever happened because I answered the phone on a freezing Sunday night. Someone wanted to see a laundromat at 6:30 PM. I showed it, and he bought it. Then he went on to buy four more. Most calls won’t close like that—but you never know which call matters. Henry Harrison: That’s a great note to end on. Bob, thanks for coming on the show. Bob Fox: Have a great day.

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