For example, he’s been deeper in the ocean than any other person. In addition to that point in Challenger Deep in the Mariana Trench at 35,853 feet below the surface, he has also been to the highest point on Earth: the summit of Mount Everest at 29,029 feet. He’s completed the Explorers Grand Slam of climbing the highest peaks on all continents and skied the last degree of latitude at both the North and South poles. And besides the Pacific’s Challenger Deep, he’s also been to the deepest point in all the other oceans.
Even Vescovo’s more mundane stuff is not all that mundane: The 55-year-old spent 20 years in the U.S. Navy Reserve as an intelligence officer, has a bachelor’s degree from Stanford and master’s degrees from MIT and Harvard, and speaks six languages. He co-founded the private equity company Insight Equity Holdings and did well enough that he can spend quite a bit of his time preparing for and executing his adventures around the globe.
And what a better way to get around to those spots than in your own Embraer Phenom 100, which he is certificated to fly single-pilot, although he usually flies with another pilot. He is also rated to fly helicopters and owned a turbine helicopter for several years. But despite his wealth and expertise, he still enjoys poking about in small airplanes. When I spoke to him in December 2020, he was flying a rental Cessna 172 from his home in Dallas to visit a business colleague in Birmingham, Alabama, the next day. “I want to build time for my ATP,” he said. He also flies a Cirrus on business trips and for Pilots N Paws missions to build time.
In 2020, he earned his commercial multiengine rating in a Diamond DA42, and he expects to complete his commercial single-engine rating this year.
He began flight training at age 19 while a student at Stanford, earning his private pilot certificate at Palo Alto, California, in a flying club Cessna 150. “In my early 20s, I was going towards my instrument rating and it was more expensive than I thought, and I ran out of money. So, I lapsed for about 10 years until I started making a bit more. I really missed flying. And then I got my instrument rating and then I was interested in helicopters.”
But learning to fly was just the start of Vescovo’s adventures. He’s always had a passion for exploring and after the mountain expeditions, he decided his next journeys should be downward. Working with an engineering firm, he designed a submersible capable of going deeper than any other ever built. At a reported cost of $30 million, it can carry two people and will withstand some 8 tons of pressure per square inch, described as the equivalent of 292 fully fueled Boeing 747s stacked on top of it. To support such missions, he bought a $20 million ship, which carries the submersible to its dive locations.
“I view my training as a pilot as absolutely essential to being able to achieve the things that I did.” —Victor VescovoThe risks of such expeditions are enormous, but Vescovo says he relies on skills learned as an aviator to help manage the risk.
“The discipline that one learns in becoming a pilot and the procedure-driven nature that you have to have to be a good pilot was absolutely essential in helping me succeed, not just in flying, but in submarines, but also in mountain climbing expeditions or polar expeditions.
“All these things are very different, but they sure as heck rhyme a lot. And by that, I mean the same process of doing your diligence about preparing yourself, looking at the weather, looking at the equipment that you’ll have, being careful, being deliberate, making decisions with incomplete information under high stress. Those are all very common things. And I think it allowed me to be successful. I view my training as a pilot as absolutely essential to being able to achieve the things that I did.”
While his experiences sound adventurous, his goal is to make them boring, which, again, he relates to how he prepares for flights. “I think we all strive to have that perfect flight where everything goes perfectly and we never miss a single thing, which, from an outsider would look like a boring flight, but I think that’s what we all strive to be….We should always strive—as I do on all my expeditions, whether it’s climbing a mountain or diving in the deep ocean—I try and take care of all the details so it is indeed a by-the-numbers, boring expedition. I don’t strive to be an involuntary test pilot.”
Vescovo says maintaining that laser focus on the details requires dispensing with two things: complacency and ego. “Those are the two biggest threats to our safety and those who fly with us. When one gets complacent, one misses the details and it’s the details that can kill you—the so-called Swiss cheese model of safety. It’s a very real thing. And the second is our own egos. For example, I climbed Mount Everest, but I didn’t do it on the first try. I trained for a year. I spent an enormous amount of resources to get there, but halfway up, I got frostbite on my hands. And even though I had the ability to push through and maybe do it, I might have lost some of my digits or I might have endangered some of my climbing companions.
“There’s nothing worth damaging yourself or damaging other people or heaven forbid, losing your life on some of these missions. There will always be another time and people have to [stop] thinking, ‘I’ll be a failure if I don’t.’ You can’t have that mentality and make it to a ripe old age doing the kind of things that I’ve been doing.”
Vescovo is adamant, though, that risk is not a reason not to do things. “It basically comes down to you. Do the things that you prioritize in your life. That’s really at least how I’ve lived. And if you really want to fly, if you really want to get that rating, like these other things I’ve done, climbing a mountain or anything else, you just have to make the mental commitment and then to follow it through, getting past the obstacles that inevitably come into our paths when life in general takes hold, whether it’s business or personal or anything else.”
He offers similar advice to youth considering flight training. “I think for young people, anyone who has even the smallest inclination that they think they might want to be a pilot, I can’t strongly enough emphasize that maybe you should do that. Do a discovery flight, take a couple of lessons because the lessons that you learn by the act of becoming a pilot will serve you so well in any discipline. It requires you to be organized, to be thorough, to check details, to make good decisions with imperfect information. These are all skills that are essential for being a good manager and a good leader.”
An enthusiastic aviator, Vescovo flies whenever he can. “My girlfriend actually mentioned to me, she said, ‘I really like it the days you go flying because when you come back, you’re happy the rest of the day.’”
So where does someone who has been to both the bottom and top of the planet go next? Space, of course.
“I am very interested in going into space. I would love to do that. That’s the one thing I haven’t done. I’d love to see the Earth from afar.”
But he’s still not done here on planet Earth. “I still continue to own and operate my submersible. And we’re still planning trips all around the world to dive to new places that have never had a man visit.”