Invest Like The Best
Episode 245 The Go-to-Market Motion
Invest Like The Best

Episode 245: The Go-to-Market Motion

Invest Like The Best

Episode 245

The Go-to-Market Motion

Jenny Lefcourt is an equal General Partner at seed-stage venture firm, Freestyle Capital. 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.

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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

[00:53:40] - Outstanding and remaining barriers to inclusive and diverse teams

[00:58:47] - The kindest thing anyone has ever done for her

The Go-to-Market Motion

Introduction

Patrick
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 covered Jenny's investment frameworks, why she believes that deep understanding of the customer is key for founder success, and what makes great go-to-market strategies. We also touched 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.

Formative Experiences

Patrick
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 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 of formative experiences that you feel really shaped your worldview and why you enjoy doing what you do so much.

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