Forty Over 40

Forty Women to Watch Over 40

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Forty Over 40 Asks: 9Qs for Jenny Lefcourt, Venture Capitalist at Freestyle

aWelcome to the Forty Over 40 blog. We frequently spotlight one of our honorees and their thoughts on reinvention, mentorship and momentum…plus a peek into what makes them tick.

This Q & A is with Jenny Lefcourt, Venture Capitalist at Freestyle.  Jenny is innovating her field of work by investing in technology companies at the seed stage and works closely with her entrepreneurs to help them build their business, build their teams, and have the next round of financing done by top-tier VCs.

1) What was a pivotal moment of reinvention for you?

When fundraising for a start-up in the fall of 2013, I met with lots of VCs and almost all were men.  The CEO and I said to each other ‘where the hell are all the women VCs?!’  I soon learned that only 4-5% of VC checks are written by women.  A pivotal moment for me was recognizing that by becoming a VC, I can change the ratio, which can have a positive impact on the entire ecosystem.

2) Who has been a valuable mentor or sponsor?

The most valuable mentors to me in this reinvention have been my business partners at Freestyle, Josh Felser and Dave Samuel.  Josh and Dave recognized that they wanted another voice at the table and they wanted that voice to not be “another white dude.”  They respect the different lens that I bring to the partnership, and trust and support me.  They also have made the journey very fun!

3) What is your biggest goal right now?

My biggest work goal right now is to be a very successful VC.  I plan to continue to back amazing entrepreneurs and help them build big, valuable companies.  As I do this, I role model what is possible for other women and I make a dent in the gender bias that exists today.  The more of us there are, the more successful we will all be.

4) What challenge / achievement are you most proud of?

I graduated from Wharton undergrad and immediately went to work in New York City as an accountant.  I chose that path because it was easy and safe–I knew that I was not passionate about that job, nor I would I ever be.  After working two years to earn my CPA (yes, I am goal-oriented), I quit and took a year off to backpack around the world, not knowing what I would do when I returned.  I am proud of that decision because it was the beginning of me taking risks and having faith in myself.  By closing the door on what wasn’t making me happy to later find work that I was very passionate about, I learned that the greatest risk is not what I am leaving but rather, not pursuing that which I desire.  

5) What is your “keep me going” quote?

My children are watching.  Knowing that I am role modeling behavior for my children, I am acutely aware of how I attack life and share the journey with them.  I used to talk to my kids about Carol Dweck’s ‘growth mindset” and now I live it and discuss it actively with them.  Giving up doesn’t feel like an option as now the stakes are higher!   

6) What was the last business book you read?

Positive Intelligence by Shirzad Chamine.  At the chance of sounding cheesy, it has changed my life and I have my dear friend and old business partner, Jessica Herrin, to thank for introducing it to me via her amazing book, Find Your Extraordinary (the book I read before Positive Intelligence).  Positive Intelligence is about mastering your mind to make you more productive and a lot happier along the way.

7) How did you feel on your 30th birthday? What were you doing at that time?

I felt great when I turned 30!  I was working around the clock at my first start-up when I turned 30 but luckily the team was made up of some of the smartest and funniest people I know.  Kit Codik was on my team and was disturbed that I was not throwing myself a party so he decided to plan one for me.  So, we celebrated at a fun bar in the Mission in San Francisco with everyone from the company and many of my friends.  

8) What time do you typically wake up? What do you do every morning?

I typically wake up at 5:30 and drink coffee and do emails for about an hour.  I then exercise for 45 minutes.  After I return at 7:15, I spend the morning with my kids– hanging out, having breakfast and getting them to school.  Then I shower and take off for work.

9) What song can’t you get out of your head?

The entire Hamilton soundtrack!  Non-stop.

Check out Jenny Lefcourt’s full 40 Over 40 profile here!

Whitney Johnson

Whitney Johnson

Whitney is the author of the acclaimed Dare, Dream, Do: Remarkable Things Happen When You Dare to Dream. She has been named on numerous Smart Thinkers and People to Follow lists by major media such as Inc. Magazine, Business Insider and Huffington Post and is quoted in Wall Street Journal, CNN, Fast Company, Forbes and more.
Whitney Johnson