I started jotting down everything I’ve done for clients this year. The list got long enough that I figured I should share it:

Tax‑aware portfolio construction

• Tax‑loss harvesting (capital) – systematically harvesting losses with a long/short SMA to reduce capital gains tax.

• Tax‑loss harvesting (ordinary) – using tax‑aware hedge funds that realize ordinary deductions that offset W‑2 / K‑1 income and Roth conversions.

• Real estate depreciation – using depreciation to shelter passive income and stack passive losses.

• Asset location – putting private equity, credit, and higher‑growth / higher‑tax assets in IRAs and Roths.

• Diversifying concentrated stocks – using long/short SMAs and other tools to reduce single‑stock risk as tax‑efficiently as possible.

• Avoiding capital gains on liquidity events – planning before you sell a business or stock, not after.

• Box spread financing – borrowing against your portfolio at attractive rates instead of selling appreciated assets.

• REPS assistance - help with logbook for tracking hours + coordinating into overall investment/tax plan

Retirement & Roth strategy

• Roth vs traditional – deciding where each new dollar should go based on your current and future brackets.

• Roth conversion timing – using low‑income years and ordinary deductions to convert IRAs, avoid ugly RMDs, and set up tax‑free money for heirs.

Equity comp & business owners

• Exercising ISOs/NSOs – planning timing, AMT, and sale strategy so a windfall doesn’t turn into a tax nightmare.

• Business deductions – making sure entity structure and deductions actually match how you live and work.

• Retirement plan set up - create and manage company 401k plan with profit sharing and cash balance plan.

Giving & legacy

• Donor‑advised fund setup – front‑loading giving to maximize deductions in high‑income years.

• Security selection for donations – giving the right lots, not just “whatever is in the account.”

• Estate tax planning – coordinating entities, trusts, and investments to reduce estate tax and protect your family.

Execution & peace of mind

• Coordinating with your CPA + estate attorney so everyone is rowing in the same direction.

• Time savings + continuity – making sure your spouse and kids have one person and one plan if something happens to you.

If your current setup isn’t doing most of this, you don’t have a tax‑aware wealth plan. You have an investment account with a helper.