How to Kick Major Hiney as an “Older” Entrepreneur

james henry_fixed
NBC Connecticut

Recently, Bloomberg Businessweek ran a piece with the incisive headline "Older Entrepreneurs Start Companies Too." It's well written and makes a great point.

So often, I think, many of us imagine entrepreneurs being young punks starting companies in their garages on shoestring budgets, like Steve Jobs. But obviously, that isn't always the case. And it didn't take a Businessweek article for anyone to realize it, necessarily.

But this piece got me curious about the "older" startup scene in Chicago, and what tips it has for people on the fence at their jobs worrying they might have waited too long to make the plunge. Truth is, they haven't. In fact, they're in good company.

"In the last six months, many older workers have given up looking for a job and have turned to becoming entrepreneurs -- at least until the job market improves," said Art Koff, who "retired," as he put it, after more than 40 years in advertising to found the Loop-based recruiting service Retired Brains in 2003. "Many others realize they must now continue to earn some moneys during their retirement years if they are to live anywhere near the lifestyle they anticipated."

Patrick Spain, 60, of both First Stop Health and Newser has two major pieces of advice:

1. The essence of entrepreneurship is managing the constant tension between steadfastness to mission and flexibility of tactics used to achieve that mission. Nothing works exactly like you think it will and if you don't iterate and change your methods, you die. Yet if you fail to remain true to your mission, you confuse your customers, your employees and, ultimately, yourself. And you also die. The trick is not to die.

 2. Chicago is experiencing a Cambrian Explosion of entrepreneurship. The last two years have seen the blossoming of an abundance and diversity of entrepreneurial infrastructure that, while it may seem sudden, has been in the works for many years. Innovation and wealth derived from that earlier innovation begets more innovation. The last major evolutionary barrier Chicago needs to overcome is the attachment
of stigma to failure.

Jeff Hoffman of the Cary, IL- and Rockport, TX-based Applied Computer Technology added that you shouldn't be afraid to use your age to your advantage. "Make yourself the visible head of the business to your customers because your 'experience' can have a calming effect on new clients who are a little gun shy of new businesses," said Hoffman. But that calming effect won't hold true of banks, who will be "reluctant to lend money to career-changers late in life." In other words, your startup money will have to come from other sources and resources.

And when you think you have enough, according to Carolyn Starks, a laid off reporter from the Chicago Tribune, you should double it. Starks, 50, who started Storybuilders, the Crystal Lake-based publisher of childrens books, also warns you shouldn't "waste money on marketing advice from online business coaches."

For more on that, see a recent piece I did on why you should be wary of (some) advisors.

Obviously, you could write a whole textbook on this subject, but this is a good couple of points in the right direction.

David Wolinsky is a freelance writer and a lifelong Chicagoan. In addition to currently serving as an interviewer-writer for Adult Swim, he's also a columnist for EGM. He was the Chicago city editor for The Onion A.V. Club where he provided in-depth daily coverage of this city's bustling arts/entertainment scene for half a decade. When not playing video games for work he's thinking of dashing out to Chicago Diner, Pizano's, or Yummy Yummy. His first career aspirations were to be a game-show host.

Contact Us