Robert B. “Bobby” Haas, chairman of the strategic advisory committee at New MainStream Capital in Dallas, is passionate about his Harley-Davidson Softail Fat Boy Lo. It’s a motorcycle with a 1690 cc engine with dual “over-under” exhaust—sometimes referred to, Haas points out, as a “bad boy” look.  Then again, it’s also outfitted with a custom sidecar, which Haas says he uses to tote his “duffel bags, his dogs, and his daring relatives.” The Softail Fat Boy is just one of four motorcycles Haas owns, and they’ve all got sidecars. Three of the bikes are Harleys, while the fourth is a Russian-made Ural Retro.

Haas bought his first motorcycle in 2011, at the age of 64. What’s the attraction for the investor/photographer? “Cycling resembles aerial photography in that speed, cruising in the open air, and a pinch of danger spice up the brew,” he says. “It’s [also] a solo activity, so I don’t depend on anyone else to explore my passion.

“There’s an entire culture to the biker world that is radically different from my other worlds,” he goes on. “Motorcyles offer a high-octane dose of freedom: you’re unconnected from communication; none of the other bikers care who you are or what you do; you can go wherever you want to go; and you only need to pause once in a while.”

So far the businessman has logged more than 28,000 miles on his bikes, including three trips of roughly 2,000 miles each along the old Route 66 from Oklahoma to California, along the Natchez Trace, and along the Rocky Mountain Continental Divide.

Harleys hold one more attraction for Haas as well. “A biker today does exactly what a biker 50, 60, 70 years ago did,” he says. “How often can you say that?”