This really smart business owner hit the limit of DIY planning/investing

• Cash balance plan used to defer millions in taxes… but the TPA somehow has it overfunded by $600k

• Concentrated, tech‑heavy brokerage account that is mostly embedded gains • Significant taxable passive income from partnership interests

• Still paying very large income taxes even after business expenses and the cash balance plan

This is where “I’ll do it myself” stops working.

Here’s what we talked about:

 

• Cash balance plan → Roth IRA (not just “kick the can”) 

The plan is great for deferral, but we need a strategy for eventually moving dollars from IRA → Roth IRA in a controlled way, not just creating a future RMD problem.

 

• Tax‑aware hedge funds for diversification and income tax relief 

These can enhance portfolio risk/return, reduce income taxes while working, and then shield Roth conversions in retirement.

 

• Tax‑aware long/short to fix concentration, tax‑neutrally 

We can diversify the concentrated stock portfolio without a giant one‑year tax hit, and realize ongoing capital losses after the fact. 

 

• Tax‑aware real estate for income and passive loss 

Create a tax‑free income stream for retirement and use excess depreciation to offset passive income from partnership interests.

 

• Box spread loans for cheaper, smarter borrowing 

Borrow at sub‑4% against the portfolio instead of taking the 9% loan his custodian quoted him.

 

• High‑octane private equity inside Roth 

Put the highest‑upside, longest‑horizon opportunities inside the Roth IRA to maximize potential legacy.

 

Individually, all of these ideas are “out there” on the internet.

The value is in:

 

• Knowing which ones fit your actual fact pattern

• Sequencing them correctly over years

• And making sure they all talk to each other instead of living in silos