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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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Most people don’t grow up learning how to manage money—let alone build multi-generational wealth. In this episode of Millions Were Made, Jessica sits down with wealth management expert Hilary Hendershott to explore what truly sets high-net-worth individuals apart when it comes to money mindset, investment strategy, and legacy planning.
Hilary shares her personal journey from financial struggle to founding a boutique firm managing over a quarter billion in assets—exclusively for women. They talk candidly about why women often hesitate to claim wealth, how to shift generational money patterns, and what it really takes to live off your investments. Whether you’re making your first sevenfigures or planning your exit, this episode will give you tangible tools and mindset shifts to create long-term wealth on your terms.
If you're a founder ready to protect what you’ve built and start thinking like a true investor, this is your next move.
Highlights:
(01:00) Hilary’s rock-bottom money moment—and what changed everything
(03:34) Why women must lead their own financial futures
(04:07) The differences in how men and women approach money
(06:45) Breaking the taboo: how mindset impacts your ability to grow wealth
(09:52) Why your network shapes your net worth
(11:09) One key investment strategy wealthy people use (but rarely talk about)
(13:57) Living off your investments: how distributions really work
(17:51) When to hire a wealth manager (and what to look for)
(21:38) How high-net-worth clients actually think about risk
(24:36) The boring but essential habits of wealthy people
(26:37) First-generation wealth: how to build a legacy that lasts
(31:18) A tax-efficient strategy most people don’t know exists
(33:33) Hilary’s favourite books and personal investment wins
(34:27) “Millions were made when I nominated myself…”
Connect with Jessica:
Instagram: @millionsweremade | @thejessicamarx
Work with Jessica: Tailored Premier
Website: Millions Were Made
Connect with Hilary Hendershott:
Website: https://www.hendershottwealth.com
Podcast: Love Your Money
LinkedIn: Hilary Hendershott
51 episodes
