In this episode of the Mind Your Farm Business podcast, host Shaun Haney sits down with Ted Oakley, managing partner of Oxbow Advisors and author of Second Generation Wealth, to discuss the critical topic of passing down wealth and responsibility in farm families. Ted draws from decades of experience helping families manage major liquidity events and navigate the delicate balance of wealth and succession.
Oakley says that the biggest threat to long-term family wealth isn’t taxes or markets, but rather human behaviour itself. He argues that children must learn the value of money by working for it and facing obstacles on their own, even suggesting that farm kids work off-farm for several years before returning to the family operation. Building character and experiencing scarcity, he says, are essential to appreciating wealth and ensuring it’s protected for future generations.
Open and honest communication is crucial, but Oakley cautions that these conversations about family finances should be gradual and tailored to each child’s maturity. Parents must also be wary of creating trust-fund dependents; if the next generation doesn’t learn to stand on its own two feet, the entire family legacy could be at risk.
Oakley shares practical tips, including limiting financial support to no more than 10 to 15 per cent of monthly expenses to promote independence. While some may balk at the idea, he also sees prenuptial agreements as a vital tool to preserve multi-generational assets, framing them as a way to protect the family’s future rather than a sign of mistrust.
The episode closes with a sobering reminder: if parents find themselves covering most of their adult children’s living costs, it’s time to reassess and reframe the family’s approach to money and responsibility. Oakley's message is clear: succession isn’t just about handing down land or assets, it’s about preparing the next generation to steward that wealth with resilience, discipline, and a sense of purpose.
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