Jenny Lefcourt - The Go-to-Market Motion

**Patrick O'Shaughnessy** (0:00)
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Hello and welcome everyone. I'm Patrick O'Shaughnessy and this is Invest Like the Best. This show is an open-ended exploration of markets, ideas, stories and strategies that will help you better invest both your time and your money. Invest Like the Best is part of the Colossus family of podcasts and you can access all our podcasts including edited transcripts, show notes and other resources to keep learning at joincolossus.com.

**SPEAKER_2** (2:20)
Patrick O'Shaughnessy is the CEO of O'Shaughnessy Asset Management. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of O'Shaughnessy Asset Management. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.
Clients of O'Shaughnessy Asset Management may maintain positions in the securities discussed in this podcast.

**Patrick O'Shaughnessy** (2:45)
My guest today is Jenny Lefcourt, general partner at seed stage venture firm Freestyle Capital. Jenny has been ingrained in the tech world since the early days of the internet. She dropped out of her Stanford MBA program to co-found online wedding registry startup weddingchannel.com. And she has stayed on the entrepreneurship path ever since.
During our conversation, we cover Jenny's investment frameworks, why she believes a deep understanding of the customer is key for founder success and what makes great go-to-market strategies. We also touch on some of Jenny's favorite market themes around technology, the aging population, the future of work, and the growing low-code, no-code movement. Please enjoy my conversation with Jenny Lefcourt.
So Jenny, I think to set the stage for at least three, probably more, really interesting topics that we're going to explore together today, it would be helpful to understand sort of the soil from which your investing career emerged. So maybe you can begin with just a thumbnail sketch of your background up until what you're doing now and maybe touch on a couple formative experiences that you feel really shaped your worldview and why you enjoy doing what you do so much.

**Jenny Lefcourt** (3:47)
Okay, well, I'm not young. I'm 52 years old. So going all the way back may be too long for your podcast. But I'll just say that I am a retired CPA. I thought I didn't like business at all and was like, I'm over it. And I came out to the Valley, came out to Palo Alto back in 1994 to discover a new kind of business, the Valley Way. And at the time, I know there's a lot to be said on this, but it was a real meritocracy. You had people wearing shorts and T-shirts with the palm trees around just trying to figure out the future. And anyone who was smart and was willing to jump in and do good things got moved up in the organization. So I had that amazing experience at a pre-IPO software company back in the sort of mid-90s.