By Semil Shah

A little more than two years ago, Jenny Lefcourt, who cofounded the wedding registry startup WeddingChannel.com and a short-lived e-commerce company called Marrkit, made the leap into venture capital.

Specifically, the Stanford MBA joined Freestyle Capital founders Josh Felser and Dave Samuel at their small but growing seed-stage fund, and she’s been helping build the firm’s brand and the rest of its business since.

We caught up with her recently to talk about her newest gig.

You’re the newest GP at Freestyle, a seed-stage fund. What’s been the most surprising part of the transition? 

I’m still an entrepreneur at heart and felt that being a seed-stage VC would enable me to add the most value to my portfolio companies while also being the most exciting and fulfilling for me as an investor. Compared to being an entrepreneur, I expected the highs to not be as high but the lows not as low, but I’ve been surprised by how high the highs are. [Watching] my entrepreneurs and their companies develop from tiny to thriving has been more of a thrill than I had imagined. I’ve also been surprised and delighted by the depth of relationships I’ve developed with my entrepreneurs. Being in the trenches with them creates quite a bond.

As some micro funds grow and add partners, what would be your advice as to how they integrate new faces?

My advice to a micro fund looking to add a partner would be to add someone who has a different lens on the world and that you trust and respect.  Groupthink can be deadly to a partnership, so you need to ensure that you not only have differing points of view but that you have a relationship between the partners that welcomes debate.  Josh, Dave and I have hearty debates, we each have unique skill sets that help Freestyle’s portfolio companies. Also, and important to me, we laugh a lot. Laughter is really underrated as the glue that holds people and teams together.

You have deep experience in retail, both as a founder and an investor. What are your views on how consumer retail transforms over the next decade? Is there any chance to find a category that Amazon won’t gobble up?

I believe there is going to be a big pendulum swing back to curation and service. The internet delivered access to so much inventory online, which was thrilling to online shoppers for a while.  Now, consumers find it hard to sift through the options and are ready for fewer, more personalized offerings.  This will require retailers to use the data they have on their consumers and provide more service to make a sale. Retailers will also need to truly become omnichannel —  the most overused and not-delivered-upon concept in retail — to provide the unique experiences that will keep them competitive in the Amazon-versus-everyone else world that we live in.

As Freestyle grows, how have you and partners evolved your thinking around follow-on funding for your seed companies?

We’ve reserved a greater percentage of our recent funds for follow-on financings than we used to. We’re usually participating in our pro-rata for Series A and sometimes Series B, and we’ll “back up the truck” for some of our best performing companies. Our usual initial check size is between $500,000 to $1 million, and our entrepreneurs are typically raising between $2 million to $3 million.  We lead rounds and write big checks for our fund size because our model is to work very hard and closely with the teams that we back.

In the context of early-stage investing, what’s something that you believe that isn’t necessarily a popularly held point of view?

I don’t seek out high-profile entrepreneurs who I know many VCs are attracted to. I find that high-profile entrepreneurs can be distracted by the many invites they get to networking events, speaking engagements, parties, advising, etc.  The entrepreneurs I have backed have all been heads-down and hard-working people who surgically apply networking. Between Josh, Dave and I — and others with whom we coinvest — we can get our teams in front of just about anyone they desire to meet.  So, while the entrepreneurs who attend events like Summit at Sea are smart, hard-working and fabulous, they’re not typically the entrepreneurs I choose to invest in.

Photo: Christopher Michel.