After 25 years and six CEO positions, Brendan Keegan had earned the right to disappear. As co-owner and CEO, he had grown the fleet management company Merchants Fleet from roughly $500 million to $2.7 billion in four and a half years. His youngest child was graduating from high school. The timing was right.
“I wanted to graduate life,” Keegan says. “I wanted to be a free agent.” For some, that might mean golfing five days a week. For Keegan, it looks more like speaking, writing, mentoring, serving on boards, investing—and wholesaling Lamborghinis, Ferraris, McLarens and Porsches as part of his latest venture: supercar trading business bFEARLESS Exotics.
bFEARLESS Exotics is the result when Keegan’s version of retirement meets his old operating instincts. Pick the work you actually want to do, keep it simple, move fast and don’t let your enthusiasm override the numbers, even when the inventory happens to be a McLaren.
Plan The Second Act Before The First One Ends
Keegan calls his approach to retirement the “second-and-one” plan. On second-and-one, the offense can run nearly any play because getting one yard should be manageable. You have options. That’s what Keegan wanted from retirement: options.
He started thinking about it years before he sold Merchants Fleet. “I talked with a lot of people who retired ahead of me, and I was shocked at how little thought they seemed to put into what they wanted to do,” he says.
Executives spend months planning office moves, product launches or major client onboarding. Then retirement arrives, and the plan is to figure it out on the fly. Second-and-one gives you the freedom to choose your next play deliberately.
Build Around What You Actually Want
Keegan developed three criteria for post-exit investments:
• Is it something you’re passionate about?
• Can you use it or experience it?
• Can it generate a financial return?
That’s the formula behind Keegan’s second act: Passion first, experience second, economics third. Economics isn’t ignored; it’s just put in its proper place.
Keegan’s youthful dreams of Magnum P.I.’s red Ferrari led to a sizable sports-car collection. Years later, he began mentoring exotic-car dealership veteran Seth Blais, who wanted to build something of his own. The opportunity was a clear fit for Keegan’s criteria, so they launched bFEARLESS Exotics.
Ultimately, his investments include businesses that create experiences for his family and friends. A board meeting might happen around a race in the U.K.; a business trip might become a family trip. Work and life aren’t kept in hermetically sealed containers.
Own Without Becoming The Operator
Keegan knew he didn’t want another corner office, and he’s quick to clarify that he didn’t leave a CEO job to become CEO of a car company. He serves as chairman of bFEARLESS Exotics, with Blais as president and CEO. Keegan provides capital, advice and mentorship but deliberately stays out of daily operations.
“If you ask me what cars we have in inventory right now, I don’t know,” he says. For a man who spent decades knowing what was happening inside his companies, that’s meaningful: His job is to help a younger CEO make decisions without him.
“I say, ‘Hey, here are some metrics that I think we ought to track.’ But I don’t get involved in tracking,” he says. He believes it’s important not to get so caught up that you end up rebuilding the chapter you just left. Instead, provide pattern recognition and 25 years of scar tissue, then let the operator operate.
Keep The Discipline That Got You There
More freedom doesn’t mean less discipline, and many aspects of Keegan’s old CEO playbook are at work within bFEARLESS Exotics. For example, bFEARLESS buys exotic cars and sells them primarily to dealers or through auction rather than directly to the consumer. Why? Simplicity. Retail can generate bigger margins but brings more complexity. Wholesale keeps expenses low and inventory moving.
Speed is part of the pitch. Sellers can get a quote the same day and potentially have money wired within 24 hours. Keegan spent his career obsessed with making businesses easy to buy from.
At Merchants Fleet, he once looked at a 28-page lease and told the company’s general counsel to reduce it to three. At bFEARLESS Exotics, the instinct is the same. Fewer steps, fewer headaches, faster decisions. Same operating instinct; the product just has more horsepower.
Let Passion Choose The Game, Not The Decisions
That balance between passion and discipline becomes clearest when the cars themselves enter the equation. Keegan says a vehicle could be his dream car, but if the economics don’t hit the company’s target, they’re just not interested. In other words, passion determined the business he wanted to be in, but it doesn’t determine the decisions he makes inside it.
In the company’s fourth month, bFEARLESS Exotics sold a Lamborghini Revuelto for roughly $610,000, a sale Keegan says set a Manheim New England record for the most expensive vehicle sold at auction.
Not bad for retirement. But then, Keegan doesn’t particularly look retired.
People tell him he’s busier now than when he was working full time. The difference is control. That’s what Keegan spent years planning for: control over how he spends his time, who he works with and which opportunities he pursues. “I’m not working 10 hours a day,” he says. “I’m traveling way more and doing, quite frankly, tremendously fun things all the time.”
At 57, Keegan says, “I think I’m having as much fun as I had in my twenties.” That’s the part of the exit story that doesn’t fit neatly on a tombstone-sized LinkedIn announcement.
Selling Merchants Fleet wasn’t the finish line. It was second-and-one, giving Keegan room to choose the next play. bFEARLESS Exotics is one of those plays. The cars may be different. The discipline isn’t.