My guest today is Jenny Lefcourt, an equal General Partner at seed-stage venture firm Freestyle Capital, where she manages $450 million in seed investments. Jenny has been engrained 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 with classmate, Jessica Herrin, which was subsequently acquired by The Knot. 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 for the aging population, the future of work, and the growing low-code/no-code market. Please enjoy my conversation with Jenny Lefcourt.
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[00:03:24] - [First question] - Her background and some formative experiences that lead her to where she is today
[00:08:38] - Common patterns of desirable founders when it comes to customer focus
[00:09:50] - Her investing framework for evaluating and deciding which companies to invest in
[00:12:32] - Innovation and adoption in the technology sector for the older generation
[00:15:11] - The biggest jobs to be done in this space currently today
[00:17:33] - Cultural differences in how the West views and treats their elderly
[00:21:02] - Business model options for turn-key apartments offered by UpsideHoM
[00:22:48] - Other categories and potential opportunities in tech geared towards the elderly
[00:24:59] - What you need to do differently when building products for the elderly
[00:27:32] - How she learns about a new prospect’s go-to-market approach and reverse engineering an action plan to execute it
[00:32:03] - Founders, You Want to Sell Viagra
[00:33:33] - Selling transformation and an overview of this idea with BetterUp
[00:36:30] - Her thoughts on how the world and the future of work might change
[00:41:14] - Interesting approaches to improving the onboarding and recruiting process
[00:43:24] - The emerging movement of low code/no code tools
[00:46:58] - How she as an investor adjusts as the world becomes more digitally connected
[00:49:02] - Ways her life has most dramatically changed over the past few years
[00:51:33] - Lessons learned from her time at All Raise