In episode 47 of The Right-Hand Roadmap, we sat down with Brenton Harrison, a Certified Financial Planner who specializes in helping first- and second-generation high-income earners. Brenton pulls back the curtain on the emotional baggage that often comes with financial success, and how easy it is to fall into the trap of compensation plans that sound good on paper but leave you over-leveraged, underpaid, or misinformed.
This episode is a must-listen if you’ve ever second-guessed your bonus structure, wondered whether equity is really worth it, or felt embarrassed not knowing what questions to ask about financial planning. Brenton’s insights will challenge how you think about money, and give you the tools to build a smarter, more sustainable financial future.
You'll hear all about:
- 00:41 – Meet Brenton Harrison: Financial planner for first- and second-generation high earners
- 02:25 – Why Brenton launched New Money, New Problems and the emotional baggage behind financial success
- 05:40 – The blind spots of compensation plans for seconds-in-command
- 07:55 – Why “you should be thankful” is a red flag in any compensation conversation
- 10:32 – When commissions and bonuses are more about control than reward
- 14:47 – How to recognize a toxic comp plan
- 17:10 – Planning for income that fluctuates (like commission-based roles)
- 21:18 – Should you accept equity? What questions to ask first
- 25:00 – The “six-figure lifestyle” trap
- 27:36 – How high earners can build a financial strategy that’s actually sustainable
- 30:41 – Why your net worth matters more than your income
- 32:19 – Tips for COOs navigating equity, risk, and career growth
- 36:03 – When to hire a financial planner—and what to look for
- 38:45 – Brenton’s advice for COOs in fast-growing companies
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