Phillypreneurs

For most professional athletes, playing in the pros is not only the pinnacle of their careers, it’s the pinnacle of their earning potential. The typical pro-athlete financial storyline goes something like this: Work really hard and overcome impossible odds to make it to the pros, sign a big contract, spend a lot of money, spend more money, retire, realize you’re spending is out pacing your income, star in regional cable commercials or land a gig as a local sports anchor, pray to God you have something left for the kids. Again, that’s most professional athletes. Lenny ‘Nails’ Dykstra is not most athletes.

For the Philly fans who lived through the glory days of the early 90’s (and the tragedy of 93), we’ll always remember Lenny Dykstra as the chaw chewing no-rules center fielder who lived the rock n’ roll life. He was put on probation by Major League Baseball for gambling. He crashed his sports car into trees and was charged with drunken driving. More recently, with the publishing of the Mitchel Report, he has been one of the bigger names associated with steroid abuse. After he retired at the ripe old age of 33 in 1996, it seemed to the ill informed masses that a professional career had run its course and a minor league sports anchor career was about to begin. Did we mention his nickname was ‘Nails’, as in the indestructible pieces of shrapnel that always seem to hang around no matter how many times you sweep the garage floor?

While the fans and the rest of the world were focused on the field and the possibility of a Phillies World Series, Dykstra was starting another career as an entrepreneur:

Dykstra’s original business venture, creating an enormously successful chain of car-wash and quick-lube establishments in Southern California. Dykstra chose car washes, he says, because of the automobile-centric culture in California, and because “it was a business that couldn’t be replaced by a computer chip.” He brought his own frustrated consumer experiences to bear in creating the business model, and eliminated many of the usual array of motor-oil choices—startup, high-mileage, various blends—from his inventory. “You get the shit out of the ground,” he said, referring to standard Castrol GTX, “or the shit made in the laboratory that’s the perfect lubricant” (Syntec). “Meaning, it’s either A or B. It’s not about the oil. It’s about the people. They got confused.” He stocked the places with baseball memorabilia and flat-screen TVs, and served free coffee (“the good kind”), so that customers would associate the experience with luxury rather than with cumbersome chores.

Finding business a natural fit, Nails expanded his repertoire and started playing the market. With his statistical mind sharpened from years of baseball stats, he became a natural day trader and quickly found himself in the rare and enviable position of making more money after his pro career then during it. Dykstra’s reputation and talent for investing eventually landed him a prestigious spot as a columnist on Jim Cramer’s popular investment website TheStreet.com. The entrepreneur in Nails hasn’t slowed down either. As of 2008 he’s stepped back from other commitments to focus on his next big venture, The Players Club:

Dykstra is launching a magazine, intended specifically for pro athletes, called The Players Club . . . The Players Club will be published monthly, and will be sent, free, to active professionals in each of ten sports, along with their agents, and club and league officials, for a total circulation of twenty thousand. It will be “photographically lush,” according to its editor, Randall Lane, and, to the extent possible, “peer to peer”—written by athletes. (The Utah Jazz forward Kyle Korver on video games, for instance, and the old Mets captain Keith Hernandez as food critic.) “It’s not just about the bling and the toys, though there’s some of that,” Lane told me. “There are all these hard-luck stories. We’re going to educate these guys to take advantage of this windfall. ‘Keep Living the Dream,’ that’s our working slogan.” Lane, who was once responsible for assembling Forbes’s annual list of top-earning athletes, is now the president of Doubledown Media, which publishes niche magazines for the extremely wealthy: Trader Monthly, Dealmaker, Corporate Leader, Private Air, and the Cigar Report.” - The New Yorker

As a Phillies legend (and Mitchel Report star) Dykstra has shown that a professional athletic career can be just the first step in a life long career as an entrepreneur.

Read more about Lenny and his latest entrepreneurial aspirations on The New Yorker website.

Dave Speers is an online marketing consultant and start-up junky that has worked with a wide variety of Philadelphia businesses. Dave spends most his time annoying really smart people at Indy Hall co-working collaborative.