Thursday Feb 22, 2024

Life Begins At The End Of Your Comfort Zone With Jess Lynch

Jess Lynch is currently the Cofounder and Founding Partner at Raiz Capital, an early-stage venture capital firm using data and community to reimagine startup investing. She was previously the Cofounder and CEO of Wishroute, a scalable behavior change platform that was acquired in 2022.

Throughout her journey, Jess has demonstrated remarkable resilience and leadership. This includes overcoming challenges like running out of cash and weathering the pandemic's impact on Wishroute's initial customers. She successfully led her company through an M&A process despite a difficult experience with one large potential acquirer. Jess credits her success to intuition, problem-obsession, and genuinely caring for people.

The interview touches on many topics valuable to founders and business leaders. Jess emphasizes the importance of having a technical co-founder or trusted advisor early on. She shares recommendations for managing fear, getting comfortable with discomfort, and pushing past the limits of your comfort zone. Additional insights include lessons learned from fundraising, managing investor relationships, preparing for acquisition, and running an accelerator program.

A key theme is Jess' remarkable perseverance and her development of an innate sense for when to push forward versus when it's time to change course. Her story demonstrates that entrepreneurial success requires hard work and also an element of luck or good timing. Overall, Jess Lynch provides a wealth of practical knowledge and inspiration for anyone interested in startups, venture capital, or leadership. This is a must-listen episode packed with forward-thinking wisdom.

Episode Outline

(00:00:00) Introduction
(00:02:06) Early entrepreneurial interests and family backdrop
(00:05:31) Brother's juvenile diabetes diagnosis inspires family lifestyle changes
(00:07:16) Educational background at Babson College
(00:10:59) Early career in forensic accounting at PwC
(00:15:33) Leaving corporate career to pursue entrepreneurial path
(00:18:22) Working on BP oil spill litigation
(00:23:32) Finding the idea for Wishroute while at Babson MBA program
(00:25:37) Launching Wishroute and early traction
(00:27:34) Pandemic causes pivot from gyms to direct-to-consumer
(00:30:58) Fundraising challenges as a female founder without technical background
(00:32:04) Mental health during startup struggles and running out of cash
(00:36:41) Large potential acquirer ends up building internally instead
(00:42:26) Emotionally difficult decision to pursue acquisition of Wishroute
(00:43:04) Warning signs when deal-making with large companies
(00:44:51) Importance of letter of intent in M&A process
(00:47:19) Securing acquisition despite numerous setbacks
(00:49:20) Lifelong lessons in resilience from journey
(00:50:07) Reluctance to jump back into startup founder role after acquisition
(00:53:30) Currently supporting portfolio companies and investing in CT