Highland Park sits inside Dallas like a city within a city, its streets lined with homes that routinely top $10 million, its zip code home to more than 30 billionaires in a single tight-knit community. That concentration of generational and self-made wealth makes it the seventh richest city in the United States, and it is the kind of place where a man casually mentions, mid-conversation at an SMU tailgate, that he is days away from closing a $2.5 billion deal. What drives people who built that kind of fortune from nothing? The School of Hard Knocks set out to find them and ask exactly that.
The first stop was Highland Park Village, one of the country’s most renowned luxury shopping centers, where cold approaches to residents produced mostly polite refusals and, eventually, a security officer with a firm warning about criminal trespass. One conversation did land before the location had to change: a commercial real estate investor who started with mobile home parks, scaled to roughly 30 apartment complexes and a thousand units at his peak, and estimated his best single year at around $100 million. His core advice was blunt: protect your credit at all costs, embrace debt as a tool when you start with nothing, and use 1031 exchanges to defer taxes by rolling profits from one deal straight into the next. On where to buy: ‘Anywhere in Texas,’ he said, pointing to population growth and a business environment he called simply great.
The Army Ranger who built 35 software companies
Outside the Hotel Crescent, a chance encounter produced the sharpest conversation of the day. Wade Myers, 67, grew up at the end of a dirt road on a farm with no electricity, no indoor plumbing, and no telephone. He went on to serve as an Army Ranger in the Gulf War, earned an MBA from Harvard, worked at the Boston Consulting Group, and went on to build 35 software companies. His biggest single exit came in at $670 million, and his greatest recorded return on one investment was 68 times the original sum. When asked what matters most now, Myers did not mention any of that. He described a mission to combat human trafficking through a venture fund that backs technology companies identifying perpetrators, liberating victims, and rehabilitating survivors. Tim Tebow is among his partners in that fund. His hiring philosophy, refined across decades: ‘Hire slow, fire fast.’ He described how any new person added to a leadership team sends the entire group back through the forming and storming stages, making a wrong hire one of the costliest mistakes a founder can make.
Fiber optics, data centers, and a $2.5 billion exit in progress
The most striking encounter happened at the SMU tailgate. A 52-year-old entrepreneur who started as a front-line technician straight out of high school, and who once picked up pop cans on the side of the road to afford lunch, was days away from closing the sale of his fiber optics company for $2.5 billion. His company built national fiber infrastructure serving major data centers and communications operators, running cable from the Atlantic to the Pacific. The advice he returned to most: ‘Create an environment where you are not needed.’ Delegate relentlessly. Surround yourself with people who are smarter than you and empower them fully. His grandfather, a lineman who became a minister, remained his most important mentor.
Louis Fy, a labor force management entrepreneur generating $375 million in annual revenue and growing at nearly 25 percent year over year, added a layer that tied the day together. He recommended working inside a large industry before launching a competing company, letting an employer fund the education that eventually makes the employee dangerous. ‘Go into a business, go work for someone else in a large industry, and see what they are missing out on,’ he said. ‘Let them pay you while you get educated.’
A financial professional who made his first million at 24 selling equities during the late-1990s bull market, and who watched much of it disappear in the dot-com collapse, offered the day’s most distilled observation: the people who actually build fortunes are not focused on the money. They are focused on being the best at what they do. The money, he said, follows.
The pop can that started one billion-dollar story
The fiber optics entrepreneur did not dramatize the memory. He just placed it matter-of-factly inside the conversation: pop cans collected from the roadside, enough change scraped together to cover lunch. It sat alongside the $2.5 billion figure without fanfare.
By the time the tailgate crowd thinned and the stadium filled, the pattern across every conversation in Highland Park that day was the same: no inherited money, no single stroke of luck, and no shortcut that held up under questioning. What held up was the dirt road, the roadside can, the discount brokerage account, the mobile home park, the technician’s tool belt, and the willingness to ask someone wealthier how they did it, which, as the fiber optics billionaire pointed out, is exactly what had been happening all afternoon.
