Entrepreneur turns global travel into family adventure

Executive: Brent Alexander, CEO and founder of the Media Monkey, a used textbook company in Venice. Founder of Sarasota-based Escape Countdown, an escape room business. A former U.S. Army officer and a cadet at the U.S. Military Academy, Alexander’s previous positions include senior marketing roles with Churchill Downs/Kentucky Derby and the NFL’s Chicago Bears and Tennessee Titans.

Diversion: Global travel with his wife, Renee Ryckman, and their children, Dylan, 14, and Logan, 12. Alexander has been to some 70 countries, while the couple’s sons have been on at least 15 trips totaling 38 countries. Alexander says he loves “the excitement and the unpredictable part” of everything you get to see when going aboard.

Worldwide: Alexander grew up mostly in Michigan, and travel wasn’t a big family  thing. “We would go to Ohio and go to an amusement park, that was our summer vacation,” he says. But when Alexander was a cadet at West Point, he quickly picked up the travel bug. First on a trip to Germany, then later, he says, “we went to Lebanon, Syria, Jordan and Egypt, where we had some really great experiences.”

‘I like the challenge of trying to find a place that people don’t always go to. Some people go boating, some people go camping. We just go somewhere.’ Brent Alexander 

Culture club: Alexander, 47, says he and Ryckman, 52, started their textbook company partially to have a recurring-revenue business “we could put on autopilot and travel for a few months of the year.” Their first trip outside the U.S. as a family was to South America, when the boys were 3 and 5 years old. That included a cruise around the coast of Chile. A highlight: when Alexander saw his sons play with other young kids, despite the language barrier. “The ability to show our kids,” says Alexander, “that no matter where you go, people are people, was huge.”

Just go: The family passport book includes stamps, so far, to Qatar, South Africa, Russia and Greece (one trip, spring break, 2018) in addition to Thailand and Turkey and ... Australia, Japan, Spain, Andorra, Peru, Ecuador and the Falkland Islands, to name a few more. For each journey, Alexander, sort of the family trip planner and cruise director, goes out of his way to find the out of the way. “I like the challenge of trying to find a place that people don’t always go to,” he says. “Some people go boating, some people go camping. We just go somewhere.”

The system: Alexander, in pre-trip mode, has turned deal finding from a hobby to a passion. He leverages the companies the couple runs by charging large expenses onto credit cards with strong travel rewards programs. He has at least 10 credit cards geared for that purpose. Says Alexander: “I’ve learned a lot of tricks of the trade over the years.”

Time travel: One of the key lessons Alexander has learned in his travels is Thanksgiving is a great getaway time because overseas it isn’t a holiday. Christmas and summers are tougher to plan and find international deals. 

Think fast: Another key is the ability to move with a sense of urgency on deals that popup. Like a few weeks prior to Thanksgiving when Alexander, at home on the computer, called to his wife in the next room, “you want to go to the Galapagos Islands for Thanksgiving?” He found round-trip tickets for $500, which can normally be at least $1,2000. Ryckman said yes and off they went. “Not many people,” Alexander says, “can be able to make a decision like that that quickly.”

Stay calm: Even with all the world chaos out there, Alexander says for the most part the family has felt safe. There was a dicey cab ride in a remote Moroccan village. And parts of Thailand were under martial law when they were there, just like there were riots in Turkey. On the latter, Alexander says the riots “only started after 5 p.m., when people got off work,” so the family was spared daytime chaos. On any trip, Alexander says the family tries to immerse themselves in the culture. “We try to fit in as seamlessly as we can to the community,” he says.

Good powder: Fitting his desire for more and better experiences, Alexander’s bucket list country is a tough get: Iran, where he wants to go skiing. Defying media stereotypes, Alexander says Iranians “are friendly, warm and welcoming.” He hopes geopolitics settle down soon, making an Iran trip plausible.