$65M serial entrepreneur with no real wealth strategy
He found my YouTube and realized he didn’t have a coordinated plan – just a collection of smart people working in silos.
He has:
- Two money managers who don’t talk to each other
- No coordination between his investment accounts and the family‑run operating business
- Sold a business unit this year with no tax planning and lost millions unnecessarily
- Dozens of real estate properties that have never been evaluated for cost segregation or cash‑out refinances
This is how most “family offices” actually start.
There’s an operating business that creates real wealth, and an investment arm gets bolted on after the fact – without anyone stepping back and quarterbacking the whole balance sheet.
There is zero chance an outside investment portfolio will ever compete with the returns a successful entrepreneur can generate in their own business.
But that’s not the job of the portfolio.
The job of the portfolio is diversification and optionality – because operating businesses carry concentrated risk, no matter how good you are.
What high‑net‑worth entrepreneurs actually need is someone to quarterback across everything:
- Investments
- Operating entities
- Taxes
- Real estate
- Estate structure
So nothing slips through the cracks.
In many cases, that means keeping the investment portfolio liquid so capital is available when business opportunities arise.
One way we do that is by using box spread loans against the portfolio – effectively playing your own bank. Instead of SBA loans at 8–11%, we’re borrowing at sub‑4% today.
At the same time, we systematically harvest millions of dollars of capital losses each year, which can be used to:
- Exit business interests
- Sell real estate
- Offset capital gains and depreciation recapture
And we carve out private equity exposure inside retirement accounts that won’t be touched for decades – where tax inefficiency doesn’t matter.
That’s the difference between having assets and having a strategy.