Jenny Lefcourt

After graduating from Wharton undergrad and working for a big company in NYC, I became disillusioned with corporate life. So, I quit my job, backpacked around the world for a year and finally landed back in Palo Alto. I worked at a consumer software company where I launched its Internet division (yes, it was 1996!) and lived through its IPO. This experience got me hooked on the Valley waycombining big ideas, smart people, hard work and a little bit of luck and great things will ensue. I found my way to Stanford business school but dropped out after my first year to co-found my first company, (bought: XOXO) where we aggregated the gift registries of all the major retailers, and after that, Bella Pictures (bought: CPI). I later invested in, consulted for and/or advised great entrepreneurs and companies such as Discord, Minted, MainStreetHub, and others before joining Freestyle. I love what I do at Freestyle which is meeting with incredible entrepreneurs on a daily basis and hustling alongside my portfolio companies. I also get tremendous joy from being a founding and active member of All Raise, a non-profit dedicated to increasing diversity in tech.  

During my time offline, I love to spend time with my husband, three kids, and our puppy.  I also hike, travel, scuba dive, read loads of non-fiction and spend time with people who broaden my view of the world and make me laugh (preferably, a lot!)

Learn from Jenny raises $4.6M

New capital for, a startup that provides an API that lets users and customers quickly integrate video chat into their product or website.

Hello, Bravado!

Today Bravado has come out of stealth mode and announced their Series A, led by Redpoint.

Founders for Change – a Movement on a Mission

Founders for Change started as a rallying cry among a generation of founders who believe deeply in the power of diversity — not only for their companies but also on their boards and in their cap tables. Since launching in March, the community has grown to 900+ founders representing over $100 billion in capital raised, with more joining every week.

Forbes: The Road Forward

How 36 women are secretly rewiring Silicon Valley - and what the means for the rest of American business.

Beware of the Beautiful Resume

As a founder, I fell prey to the beautiful resume more than once. I believed that my startups had gotten far enough along and were now worthy of the people who had worked in top positions at the very best companies...I was disappointed many times.

Startup Capital is Ammunition, Not Oxygen

We often hear stories about startups that spent too much, too fast and many times, spent foolishly on things like parties and Herman Miller chairs for all. What we don’t hear enough about are the startups that were too frugal and rather than investing in key initiatives, they held onto cash for dear life.

Framework of Trust Between Founder & VC

As a VC, I work hard to earn the trust of my entrepreneurs. The moment I wire the money, in my mind, our interests are aligned — we both want them and their company to be wildly successful.

12 Traits VCs Look for in an Entrepreneur

Everyone talks about how important the founding team is when VCs are looking at investing in start-ups but rarely do we VCs tell you founders exactly what we are looking for. This is because it is hard to say exactly — ‘I know it when I see it’ often gets thrown around. But the truth is that many of us VCs do have a list of traits that we are looking for in our founders.

Founders, Your Goal Of VC Meeting №1? Meeting №2

Founders, your sole goal of meeting no. 1 is to get the VC to want meeting no. 2. Meeting number one is not the time to share every last detail about the business and market just to prove that you know your stuff.