Tait Duryea and Ryan Gibson sit down with Jenny Spradling, co-founder of FreeWill, to explore how estate planning can be simpler, faster, and even free. Jenny explains why millions of Americans still lack basic estate documents and how that creates major complications for families. The conversation breaks down probate, wills vs. trusts, and why both are often needed. They also uncover powerful strategies around charitable giving, including how donating appreciated assets like stock or crypto can dramatically increase tax efficiency while maximizing impact. This episode offers practical insights for pilots and high-income professionals thinking about legacy, taxes, and protecting their wealth.
Jenny Spradling is the co-founder and co-CEO of FreeWill, a platform that provides free estate planning tools to individuals across all 50 U.S. states. A serial entrepreneur focused on financial access, Jenny previously founded Paribus, a consumer fintech startup. Through FreeWill, she has helped over 1.4 million people create estate plans and facilitated nearly $14 billion in charitable bequests. Her work focuses on making estate planning simple, accessible, and integrated with modern giving strategies.
Show notes:
(0:00) Intro
(3:22) Jenny Spradling’s entrepreneurial background
(6:56) Why people include charity in estate plans
(11:34) Understanding probate and why it matters
(13:30) State differences in estate planning laws
(16:44) What happens when you die intestate
(20:22) Why trusts still need a will
(24:24) When to use online estate planning vs attorneys
(31:10) How to start thinking about charitable giving
(44:15) Major tax advantages of donating stock
(47:55) Outro
Connect with Jenny:
- Website: https://www.freewill.com/
- Email: Jenny@freewill.com
- LinkedIn: https://www.linkedin.com/in/jenxia/
Related Episodes:
- #114 - Trusts, Taxes & Transfers: What Every Investor Should Know with Amanda Wynalda
- #127 - LLCs, Trusts, and K-1s: Smarter Asset Protection with Adam Kintigh
- #137 - Revocable Vs. Irrevocable Trusts: What Pilots Must Know with Adam Kintigh
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*Legal Disclaimer*
The content of this podcast is provided solely for educational and informational purposes. The views and opinions expressed are those of the hosts, Tait Duryea and Ryan Gibson, and do not reflect those of any organization they are associated with, including Turbine Capital or Spartan Investment Group. The opinions of our guests are their own and should not be construed as financial advice. This podcast does not offer tax, legal, or investment advice. Listeners are advised to consult with their own legal or financial counsel and to conduct their own due diligence before making any financial decisions.