E15: Google Alum Spencer Cassidy (YC W19) on Founding LifeLegacy, an Estate Planning Startup

Superconnector with Matt Joseph

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E15: Google Alum Spencer Cassidy (YC W19) on Founding LifeLegacy, an Estate Planning Startup

An in-depth interview with Google Alum Spencer Cassidy (YC W19), the Cofounder and CEO of LifeLegacy, an online estate-planning startup.

Superconnector

and

Matt Joseph

May 23, 2024

Transcript

Show Notes

In episode 15 of the Superconnector podcast, Matt Joseph interviews Spencer Cassidy, the Cofounder and CEO of LifeLegacy. Cassidy is a Google alum who sold his first startup Balto (YC W19) to a publicly traded company.

We cover his journey from working at Google for 5 years, to the successful acquisition of his previous startup Balto, to founding LifeLegacy, an estate planning platform inspired by personal tragedy and the COVID-19 pandemic.

Chapters

00:00 Welcome

00:38 The Genesis of LifeLegacy

04:11 How LifeLegacy gets customers

05:58 Developing strategic partnerships

08:10 Why bootsrapping made sense

11:07 Bootstrapping vs Venture Capital

14:48 The personal tragedy behind LifeLegacy

18:20 Raising a family as a founder

20:13 Advice for aspiring founders

22:32 Working at Google vs being a founder

23:20 Lessons from angel investing

27:51 Most rewarding part of being a founder

32:07 Sports, Startups, and the Skills That Translate

Discussion about this podcast

Superconnector with Matt Joseph

Matt Joseph explores the world of startups and venture capital by interviewing founders, reviewing startup pitches, and analyzing venture capital deals.

Matt holds a JD/MBA from UCLA and an AB from Princeton. Visit superconnector.com for more information and to join our mailing list.

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