Charlie Ansanelli is co-founder of two of the Bay Area’s most successful monthly events: the Treasure Island Flea and Jack of All Trades markets. These events regularly attract weekend crowds of more than 10,000, plus hundreds of local curated vendors and dozens of the best food trucks.

(Photo Courtesy of Charlie Ansanelli)

(Photo Courtesy of Charlie Ansanelli)

A serial entrepreneur, Charlie launched, a peer-to-peer parking marketplace for neighbors to rent idle parking spots to commuters in need, which was acquired by SpotHero in 2015. Most recently, Charlie has built and launched, a service aimed at making it easier to compare and book limo services online. Charlie studied business entrepreneurship with a minor in electronic commerce at San Francisco State University.

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What is Ansanelli Productions, and how did you dream it up?

Ansanelli Productions is an event company with a mission to provide affordable platforms for local entrepreneurs to meet and sell directly to their local audience. I saw a lot of great talent being displayed in online marketplaces and thought it would be great to bring that to a local, tangible, real life experience.”

You’ve had several startups. Do you think ideation can be taught?

“It’s hard for me to say, since ideas were never the problem for me. I probably have three new business ideas in play every day. The world is full of problems and better mousetraps for solutions. Execution, patience, focus and persistence are the real nuts to crack.”

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What’s your favorite role among the many involved in being a “Jack of All Trades”?

“Being a ‘Jack of All Trades’ has its advantages and disadvantages. I’m possibly unemployable because my skill sets are not focused in one arena. I know a fair amount about everything, but not everything about one thing. But for me, that’s the only way I want to live, as I have a passion for every spoke of the business wheel. I’m equal parts product, marketing, sales, finance and operations. I hire people who specialize in each needed skill set and manage the direction of their efforts toward the company’s goals. It works!”

What tech skills would you most recommend to someone looking to pursue entrepreneurship and startups as a career?

“Great question. As an entrepreneur, I think you have to be well-rounded. Sure, you can hire for your weaknesses, but if you don’t at least have some level of knowledge in each aspect of your business, then how do you know what you are hiring for and how can you manage that job role? For me, sales and marketing came easy, but product and data-driven marketing was an unknown. So, I spent lots of hours learning what I didn’t know, and it’s gotten me to where I am today. Of course, I’m still learning every day.

For aspiring entrepreneurs, I always suggest to join a startup. Do whatever it takes to be a part of a small and growing team, even if it means working for free. You’ll learn a ton about executing ideas, and execution is the only thing that matters. Ideas on their own are worthless.”

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Laurie Jo Miller Farr loves walkable cities. A tourism industry professional and transplanted New Yorker by way of half-a-lifetime in London, she’s writing about the best of the bay and beyond for Bay City Guide, AXS, Examiner and more.