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 way—combining 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, WeddingChannel.com (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

Jenny’s Companies

BetterUp

Working with Jenny and the Freestyle team has been one of the most rewarding parts of building BetterUp. They take the time to learn deeply about what makes your business special and where they can add value based on that understanding. The balance of being seasoned operators, experienced investors, and all-around amazing human beings, continues to provide me with a lifeline of everything from fundraising advice, to inspiration when things get tough, as they inevitably do when building a company. I can’t recommend Freestyle enough.”

—Alexi Robichaux, Founder, BetterUp

Narvar

Freestyle has been in the trenches with us every step of the way – they helped us create a formidable business and cultural foundation that is fueling our growth for years to come.””

—Amit Sharma, Founder, Narvar

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Jenny Lefcourt @jennylefcourt

At @freestylevc, we are all serial founders and have all experienced differing types of mental health issues in our careers. Today we announce our investment in our founders' mental health.

For the Love of Founders... https://t.co/GBRMxkJ5gt

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Jenny Lefcourt @jennylefcourt

I just danced my ass off and had a BLAST at a 9:30am class in soho and am immediately signing up for @steezystudio when I get back! @janamal, you with me?!!! I’ll procure the lights and disco ball. 10 min later and entry way is full of elated peeps practicing the choreography https://t.co/gspHBePEkS

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Jenny Lefcourt @jennylefcourt

Made a snarky Trump comment while checking in to my nyc hotel with the assumption that the guy next to me would laugh/agree but nope...“I know the man well and he is great” was the reply. https://t.co/dNoEPCZOo1

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Jenny Lefcourt @jennylefcourt

I am a sucker for a young entrepreneur... https://t.co/5pmvycCn5a

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Jenny Lefcourt @jennylefcourt

My teen was out on a date last night and when they asked for the bill, the waitress said that another patron had taken care of it. They didn’t know anyone in the restaurant. That is some next-level random act of kindness! I am totally going to do the move the next chance I get!

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Jenny Lefcourt @jennylefcourt

I have cheered for @AmyErrett and @madisonreedllb from afar until today. Currently getting my roots dyed and amazed by the genius...convenient location, no mirrors (thank you!!!), easy booking, fast & inexpensive. Very thoughtful customer experience being delivered! https://t.co/oMNYI1zDWo

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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.

A Startup, Embark, Wants to be a 23andMe for dogs

A dog lover who studied computer science and biology at Harvard, Ryan Boyko, 33, is the cofounder and CEO of Embark, a Boston-based company that tests dog DNA.

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.

Learn to Love Fundraising

Fund raising is not something most entrepreneurs look forward to doing and that may be the understatement of the year. Some fear the rejection, some are concerned about the time suck and the impact it will have on their business, and others are simply nervous because they have never done it before. Many women in particular have been scared away by reading one too many articles about how hard it is to raise VC money as a female. No matter your gender or your stage, if you need venture capital to build your build your business, you need to learn to embrace the fundraising process.