How This Entrepreneur Turned Her Ignorance Into A Huge Success

How This Entrepreneur Turned Her Ignorance Into A Huge Success

By Denise Restauri / Forbes.

This is Mentoring Moment #15 — a series of ”you need to know” stories (each told in under two minutes) from successful women of multiple generations.

“She was never bored because she was never boring” is a quote that describes Jenny Lefcourt. Jenny graduated from Wharton undergrad, worked for a big NYC company for a few years and realized corporate life wasn’t for her. So she quit her job and spent the next few years backpacking around the world. She landed in Palo Alto and got hooked on the Valley way — combine big ideas, smart people, hard work and a little bit of luck and great things will happen. She found her way to Stanford business school, but dropped out after her first year. And that’s when she cofounded her first company,, where they aggregated the gift registries of all the major retailers. Sold that company and launched Bella Pictures. Sold that company and went on to invest in and advise entrepreneurs and companies like Minted, StyleSeat,, MainStreetHub, WeddingtonWay. Today, Jenny is a partner at Freestyle Capital which invests in early stage startups. This is Jenny’s Mentoring Moment, in her words:


Jenny Lefcourt. Photo credit Chris Michaels

It’s 1998 and I am 27 years old. My business partner and I are about to pitch Kleiner Perkins the next morning on investing in our startup. We know Kleiner is considered the best venture capital firm in the Valley, and while we have our presentation down cold, we need to be ready to answer any question that may come our way. We thought we had time on our side. But the meeting got moved up a week and we are now down to one last evening of prep.

I call Jim, an old boss and mentor of mine, who was a successful serial entrepreneur and a former VC. I tell him the situation and he immediately says, “Where are you?” When I tell him we are at Stanford and will be there all night, he tells me to hold tight, he will drive down from San Francisco right away to help us get ready.

Jim arrives and instantly begins grilling us: How will we get the retailers to sign on? What percent of each transaction will we get? When will we be profitable?… The list goes on. After a couple hours of this exercise, we have answered every last question of his and are feeling strong. Jim nods approvingly. He then leans back, lets out a hearty sigh and shakes his head and says, “My God, do I envy your ignorance.” We look at him quizzically. “You think all you need to do is knock down this one barrier and you are home free, but all I can see are the twenty barriers behind the first barrier, and just thinking about them all makes me tired,” he told us.

It was then and there that I learned to embrace the power of naiveté. Not knowing how hard something will be can be the secret weapon you need to pursue what others perceive as impossible. Many of us women dwell on our lack of knowledge or experience and convince ourselves that we are not ready for a promotion or that there is someone more qualified for a particular job. I’ve realized that the most qualified people are the ones who have the vision, passion and energy to pursue that vision. In my experience, missionaries outperform resumes and should not be underestimated.

And so that’s what we did when we pitched to a roomful of potential investors the next day. We zeroed in on what we wanted to build and addressed the challenges. Our pitch was about possibility and we delivered.

Watch on Forbes:

Denise Restauri is the author of Their Roaring Thirties: Brutally Honest Career Talk From Women Who Beat The Youth Trap now available for iBooks, Amazon, and Vook.



February 17, 2016 / by / in , , , , , , ,

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