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. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [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 [00:15:11] - 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 [00:43:24] - 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 [00:53:40] - Outstanding and remaining barriers to inclusive and diverse teams [00:58:47] - The kindest thing anyone has ever done for her

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