After transitioning ownership, Tampa land dealer rolls on…The Dirt Dogs Featured In the Business Observer

Bill Eshenbaugh and Ryan Sampson work as team running Eshenbaugh Land Co., the firm Eshenbaugh founded and built and Sampson now owns.

By Louis Llovio | 5:00 a.m. May 26, 2023

Bottom Line

Key takeaway: Years of working together, and a mutual admiration and respect, have helped Bill Eshenbaugh and Ryan Sampson, make the transition from one generation to the next go so smoothly that most outsiders don’t even notice the ownership changed. 

Core challenge: Despite the growth of the firm, macro-economic challenges have made it tough for the brokers who are having to work harder to get deals closed and to land listings. But, they say, that’s just part of the game and you learn early to save when times are good for when times are tough.

What’s next: Bill Eshenbaugh will be 81 soon, but in a 90-minute interview used the term “slowing down” only once. As for Ryan Sampson, he’s working on growing the firm.

Sitting in the conference room of their office on South Willow Street in Tampa, Bill Eshenbaugh and Ryan Sampson couldn’t be any more different.

Eshenbaugh, known far and wide in the commercial real estate industry as the Dirt Dog, is 80. A cowboy type in boots, jeans and a thick mustache, he’s straight out of central casting or a Larry McMurtry novel. Sampson, too, is straight out of central casting if the part calls for an standard white male in his 40s working in commercial real estate. He’s in khakis and a polo shirt.

One is analytical, the other is a storyteller. One likes to dig into data, the other rides his horse while tapping out messages on his iPhone.

One is the teacher. The other the student.

But as different as the two men may appear, they have formed a partnership and relationship that has positioned the firm Eshenbaugh started more than 30 years ago to live on for a long time.

The future of the business is so solid that in 2015 Sampson, then in mid-30s, bought the company from his mentor. (He won’t disclose what he paid.)

“We sat down and structured a transaction when it was time for him to be a principal. So, he’s now principal here,” says Eshenbaugh, who today is the firm’s president.

“I’m 80 — I’ll be 81 soon I guess — and we’re trying to transition a little bit away from being too Dirt Dog centric and being more of team. Team Dirt Dog, and that kind of thing. We’re working in that direction to build it.”

School of life

That the person Eshenbaugh chose to succeed him was someone he taught, isn’t really a surprise.

Growing up on a family farm in Pennsylvania, he’d wanted to become a history teacher growing up. That began to change one day when he was about 17 and took drive with a with an older cousin named Dale “Wally” Waldenmyer.

Waldenmyer was in the real estate business and asked his young cousin if he knew what teachers working in the local school district were earning.

Eshenbaugh had no idea, but he knew they drove cars that were only a few years old, wore suits to work and owned homes.

The answer, Waldenmyer said, was $3,600 a year. That wasn’t too bad. The girl he was going with at the time was going to be a nurse, so they’d have two incomes when they married. He could live with that. Everything would be fine, and it would be a good life Eshenbaugh thought.

But then his cousin asked the follow up question that would change everything. “You know what I made last year in the real estate business?” he said, “I made over $100,000. You don’t tell your dad and mother, that not their business. I made over $100,000 that’s almost 25 years of teaching.”

Eshenbaugh would go on to graduate for Penn State University. He went on to run a trucking company owned by his former wife’s father for 15 years before the company closed. The family made its way to Florida and in 1983 he got the homebuilding business for a bit. After a divorce that he says was “not a good career move for your employment or your net worth because I worked for the family company.”

He worked for a couple of years in the late 1980s for the Resolution Trust Corporation helping it value properties during the Savings & Loans crash. (He did similar work after the 2008 housing crash.)

In 1992, he started Eshenbaugh Land Co.

But as much as he did in business, teaching was never far away. He still loves teaching — and history — and has continued training and mentoring others including through the Realtor’s Land Institute.

“Bill is just one of those larger than life figures that’s been out there,” says Dean Saunders, founder, managing director and senior advisor at SVN Saunders Ralston Dantzler in Lakeland “He’s selfishly given of his time and talent to help and mentor younger brokers. He’s always quick to give counsel and advice and to help people.

The two men have been friends since they were forced to drive together from Atlanta after a hurricane warning forced flights to get cancelled at a conference they attended 25 years ago.

He trusts Eshenbaugh so much that when his own son was getting into the business about 12 years ago, Saunders asked if he could advise the young man. “He could say things that I would also say, but it would be heard differently,” says Saunders.

“He picked that mantle up for me with my own son and helped kind of coach him a little bit, which is great.” 

Ryan Sampson, the principal at Eshenbaugh Land Co., joined the firm two weeks after graduating college.

Long day

Sampson was a student at Florida State University when he first met Eshenbaugh.

Sampson’s father, a commercial real estate broker and industry leader in Tampa, Russ Sampson, called Eshenbaugh in March 2005 to ask a favor. This was “my heyday,” Eshenbaugh says.

Sampson’s son was coming into town and was interested in the land brokerage business. Would Eshenbaugh take some time to talk to the young man?

“I put him on my calendar for an hour, and I’m wondering if I can make this a half hour because, you know, I’m busy as hell,” Eshenbaugh says. But it only took 10 minutes to realize he better conduct a real interview or risk him walking out and taking a job elsewhere.

When the hour was up, Sampson thanked Eshenbaugh and said he had to go. He had another interview. “I said, ‘Oh, how about skipping classes on Monday at Florida State? You ever do that?’”

The following Monday, they had meetings starting at 7 a.m. and planned to work until as late as 11 p.m. Sampson wasn’t driving back to Tallahassee that night. The day started with a “hard-headed meeting” and then proceeded from there, ending late that night after dinner with a few developers.

It was a long, hard day but Sampson learned more in those hours than a semester in college.

Sampson graduated from Florida State in the spring of 2005. Two weeks later, he went to work for Eshenbaugh.

“It’s a great business and I’m very fortunate. He’s the best mentor you could ever ask for,” Sampson says. “I mean, we’ve grown. When I started, it was just Bill. And now, we’re up to eight agents and I would say every one of them here looks to him as a mentor. He’s done a fabulous job. Even some of our competitors look him as a mentor.”

Modern history

Today’s Eshenbaugh Land Co. is far different from the one the company’s eponymous founder opened July 1, 1992 and ran as a one-man operation for many years. The focus remains land sales, a specialized piece of the commercial real estate market. The firm today runs out of a converted house on Willow Street bought and renovated in 2016, and operates with eight agents, double the number from seven years ago. Sampson, 40, has focused on putting processes in place and improving the firm’s technology.

Sampson and Eshenbaugh say what they are building is a generationally successful firm that, to be blunt, doesn’t die when the principal dies. Along with the additional agents, the firm has taken on deals in a bigger chunk of the state, as far south as Cape Coral and north to Ocala. Before, the focus was on Tampa and Hillsborough, Pasco and Polk counties.

What hasn’t changed is the ultimate goal: representing landowners and getting them the highest prices for their properties. 

And they are very good at that.

Sampson was recently named Broker of the Year by the Realtors Land Institute, an affiliate of the National Association of Realtors. And Eshenbaugh won the award for Top National Producer and Broker of the Year-Residential Land Sales.

By his own count, Eshenbaugh has completed as many as 5,000 deals since starting the firm. The list includes a $36 million sale of 496 acres in Pasco County, in the Central Pasco Employment Village along State Road 52 in July, followed by the sale of 750 acres for 2,600 or more homesites on a ranch in Osceola County for $32 million.

The Pasco deal is notable because just seven months earlier Sampson had closed a $52 million sale for an 875-acre parcel in the same development. And in September, he sold nearly eight acres on Tampa’s waterfront for $9.85 million that will be home to a mixed-use apartment development.

Business has slowed down a bit in recent months as the economy has slowed, but they are closing sales and constantly working on deals. Whatever slow down the firm is facing is cyclical, the executives say.

As well as they work together and as focused as they are on the future, there are still squabbles. 

One is over the quarterly market report. Eshenbaugh still insists, though he’s begun to loosen up a bit, that it be ready and delivered by the 15th of the month it is to be released. Sampson says the deadline is artificial, that he rather move a little slower and triple check the details. Plus, he says, those who get it are largely receiving it digitally so they don’t even think about the date.

It’s not a big disagreement, and by no means is it detrimental to the firm or the long partnership. But it serves as an example of the delicate balance that happens when the generation which has built something from the ground up hands the keys to the castle over to someone who cares every bit as much but has different ideas.

“It’s been a great transition. I still say he’s my boss,” Sampson says. “He may get mad at me at for some things that I do, but, at the end of the day, I obviously have a lot of respect for Bill and what he started so I’m trying to keep it going. My goal is trying to just grow it.”

Dirt Dog? Where did that come from?

Bill Eshenbaugh got the name Dirt Dog over beers.

The story, as he tells it, starts with a large corporate commercial real estate firm in Tampa wanting to start a land department. The firm wanted to hire him to run it, but he didn’t like the idea going downtown every day, wearing a white shirt and sitting in a cubicle. Instead, the two sides formed a joint partnership.

The firm had a young man on staff named Don it was trying to train to become its “land guy.” Eshenbaugh would work with him.

One day, the pair went to pitch for a listing for a $5 million multifamily property on Livingston Avenue.

At the end of the proposal, the property owner turns to Eshenbaugh and says, “I’ve talked to my partner and we all know you.”

That should have been a good sign. But it wasn’t.

He was known, the owner said, for doing work for the Resolution Trust Corporation and later with the Federal Deposit Insurance Corporation to get rid of distressed properties. He remembers the owner saying, “that if your sign goes up on our property it’s going to stigmatize it. It’s going to taint it. We’ve decided not to list with you.”

After the disastrous meeting, he and Don headed to the bar at the Hyatt in the downtown building Don worked at to commiserate over a couple of beers.

Eshenbaugh was moaning and groaning about what had just happened. “Come on,” Don says trying to cheer him up, “an old dirt dog like you can just shake it off. We’ll go get the next one.”

It so happened that at this time Eshenbaugh was trying transitioning from an old CompuServe account that required numbers for an email address to one where you used a name. “I said, ‘Yeah, how about that? Dirt dog. I don’t like the old part but maybe I’ll just try it.”

He first tried to see if it was available as a website address. It wasn’t. A motorcycle club in New York had already taken it. So, he added the word The and it worked.

A signature name was created and it’s stuck.

Eshenbaugh says that a marketing professional he’s known for years recently told him that “if you’d paid 100 grand you would not have got as big of a bang as you’re getting for a  free name made up over a beer.”

One more wrinkle to the story. Over the years people have tried to call Ryan Sampson, first Eshenbaugh’s protégé and now his boss, the Dirty Puppy. Thankfully, they both say, it didn’t stick.

“We’ve tried to avoid that,” Eshenbaugh says. “That doesn’t sound like the name for a guy who’s now 40, right?”

Thank you to Louis Llovio for the great article and feature as well as Mark Wemple for the amazing photos.