I Left My C-Level Job at 38 to Build the Advisory Firm I Couldn’t Find

When I left my C-level job in 2024, I didn’t have a business plan. I had a conviction.

I was 38. Income from my investment portfolio had already replaced my salary. I’d spent years building something most financial advisors told me wasn’t realistic. A life funded by cashflows from investments, not a passive index fund I’d spend down at 65.

All along the way I had been looking for an advisor who understood what I was building. Someone who could help me go further. Private markets, real estate, infrastructure. The way large endowments invest to fund their mission in perpetuity, but for individual investors.

I couldn’t find one.

Every advisor was oriented around a 60/40 portfolio and a retirement at 65.

So I decided to build what I had been looking for. Something for people like me.

I now work with people who want to replace a paycheck with income from their portfolio. Not someday, on an arbitrary retirement timeline, but intentionally and as soon as their portfolio makes it possible.

What I love about what I’m doing now: I sit down with people and show them how to cut years off the timeline they had in their head through the same style of investing and financial planning that made it a reality for me.

If you’ve had similar experiences with financial advisors trying to stick you into cookie-cutter formulas, I’d genuinely like to hear about it.

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Twice-monthly letters on the financial and emotional tradeoffs that come with mid-career success. No paywalls.

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Twice-monthly letters on the financial and emotional tradeoffs that come with mid-career success. No paywalls.

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