Executive Profile: Cal Simmons

Cal Simmons: Chapter chairman, D.C. TIGER 21

Date: Friday, November 4, 2011

The Basics

Background: His first week of journalism school, Simmons broke the news to his adviser: He wanted to be a master communicator and entrepreneur, not a journalist. Starting in his sophomore year, he’s created about a dozen companies, including three catering to travel, and invested in about 50. That resume earned Simmons, 60, his latest job: head of the first D.C. chapter of TIGER 21, an exclusive “club” for area angel investors.

Education: Bachelor’s in journalism, Kansas University

First job: Delivering The Evening Star.

Family: Wife Sally and children Charlotte, 20, Jeremy, 17, and Amanda, 13; lives in Old Town Alexandria

Business strategy

Biggest startup mistake: Everybody thinks they need to raise $1 million to get started. I’m of that old school that thinks people can get by on less money. Too much can really hurt a company. They rent too much office space and hire too many people and buy fancy desks. If you’ve got the money in the bank, you spend it. I would rather find an entrepreneur who has some of his own money at risk.

Next big goal: TIGER 21 started in New York, and they have seven active chapters. So I’d like to create at least two or three in D.C.

On TIGER 21: People fortunate enough to develop investable assets, they’re sometimes embarrassed to talk about that. It’s not the kind of thing you go with golfing buddies and say, “Gee, should I buy this new company?” They may not be in the same economic position in life. But in TIGER, everybody has the ability, so there’s no hesitancy to say, “Should I buy this company?” or “Should I buy a second home in Florida?” or “Should I get a bigger boat?” Most members have worked very hard to get where they are and still welcome advice from people who have been there.

Best lesson from your mentor: When I opened my first travel agency, I probably would have been content to have one location. But a mentor, nine months later, said “Why not open a second one in Georgetown?” It honestly hadn’t occurred to me. Five or six years later, I had 10 branches.

Judgment calls

Biggest missed opportunity: I was on the board of a company that convinced the original founder of Five Guys to franchise, and I could have bought any franchise in the country. I didn’t think it would work, didn’t see how it could compete outside of Washington. So I passed on that. It makes me very humble.

Craziest career decision: Starting my first business out of college. I literally had no money. My dad was a career civil servant here and thought I was absolutely crazy. To pay the rent while I was getting that business started, I got a paper route delivering The Washington Post in apartment buildings where I lived. And my dad, people would ask him, “Cal’s out of college, what’s he doing?” He would say, “He’s working for The Washington Post.”

How do you recover from failure? Just because you failed once doesn’t mean you’re going to fail again. Sports have really helped me. You can use any analogy you want – just because you struck out once doesn’t mean you’re going to strike out the next time up. If you play sports, that’s just intuitive. So I’ve never thought that failure was a final thing.

True Confessions

Guilty pleasure: Five Guys hamburgers.

Favorite travel spot: Grand Canyon, it’s the most magnificent place there is.

Where do you have yet to travel? The Galapagos. Being in the travel business, I made lists years ago of places I want to see. Of the places I wrote down, that’s the only place left.

Your go-to karaoke song: Don’t do karaoke, can’t even sing “Happy Birthday.” My singing would clear a room

.Favorite hobby: Playing tennis.

Favorite movie: That’s really tough, I could name 50 favorite movies in every category. “Cesar & Rosalie,” a French film. I’ve probably seen it more than any other movie.