Keeping Land in Your Family for 250 Years | Jake Oliver
About this episode
Jake Oliver discusses the challenges and strategies of keeping family land for over 250 years.
Bonus lessons + a library of insights for legacy minded families: https://dynastus.com/ytletters Jake Oliver's family has held the same land in Maine since 1782. Seven generations, through a war wound, a house fire, and a housing boom that nearly swallowed the land next door. In this episode, we talk about what it actually takes to keep land in a family for that long: the trust structure Jake built for his own daughters, why his father spent decades quietly buying back parcels that had been sold off, and why Jake believes legacy is "more caught than taught." Find Jake here: - Website: https://www.jakeoliverinvestments.com/ - X: https://x.com/Jake___Oliver Check out these episodes next: The Secret Behind Generational Homes (Conor Lynch) The Flaws in Every Estate Plan (Steve Gibbs) TIMESTAMPS: 0:00 Intro 1:15 Jake Oliver's Land 5:41 Generations on the Same Land 11:08 Ancestral Land Acquisition 14:21 Land is Raw, Living is rough 19:19 Developed over time 24:06 A sense of Stewardship 26:11 Heirs to the Land 27:16 Threats 30:59 Fiscal Benefits 35:40 Investing Your Time 40:12 Nobody will care like you do 45:25 Instruments to Protect Land 51:13 Head of the Family 59:29…
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