We manage concentrated positions.
A concentrated stock position — often created by years of employer equity continuing to vest — ties too much of your net worth to one company. We help you reduce that exposure on a tax-aware schedule, not in one painful sale.
// THE PROBLEM
The danger isn’t the company. It’s the concentration.
Concentration risk is the exposure that comes from holding a large share of your wealth in one stock — here, usually the employer whose RSUs or options built the position. For many tech employees, the same company signs the paycheck and dominates the portfolio. A rough year for the share price and a rough year for the business tend to arrive together — exactly when you can least afford it.
// THE GOAL
Trade a single decision for a managed process.
Concentrated position management reduces single-company risk gradually while controlling the tax cost — not by liquidating everything at once.
// STEP 1
Reduce the downside
Cap near-term risk while you plan — a hedge, or trimming the easy lots.
// STEP 2
Diversify on a schedule
Move out of the position over several years, sized to your goals and basis.
// STEP 3
Consider the taxes
Time sales, harvest losses, and use deferral tools so the bill is managed, not stumbled into.
// THE TOOLKIT
The strategies we actually deploy — not a menu of theory.
Which tools fit depends on your cost basis, your timeline, and what you want the money to do. Each has its own page with the mechanics and trade-offs.
HEDGING
Collars, covered calls, and protective puts cap the downside while you plan the exit.
DIRECT INDEXING
A loss-harvesting “bank” — harvest losses to offset the gains from trimming.
LONG/SHORT
Harvest losses on both sides: a long/short portfolio holds long and short positions to realize more offsetting losses than a long-only approach.
EXCHANGE FUNDS
Pool into a diversified fund and diversify in-kind after a holding period.
351 CONVERSION
Diversify without the lockup by contributing appreciated stock into a tax-deferred ETF.
CHARITABLE GIVING
Give the lowest-basis shares — often the most tax-efficient path for low-basis lots.
// THE FRAMEWORK
Not every share should be treated the same.
A tranche approach sorts the position by cost basis and gain size, then matches each group to the strategy that fits it — rather than applying one decision to the whole holding.
MINIMAL GAINS
MODEST GAINS
BIGGEST GAINS
Sell first — Recently vested / higher-basis lots are the cleanest to diversify early.
Hedge or harvest — Collars or direct-indexing losses manage the middle over time.
Defer, gift, or hold — Charitable giving, deferral tools, or the estate step-up.
// LIQUIDITY
Reach the cash without triggering the gain.
Borrowing against the position can fund a purchase or a tax bill without selling shares — though each method carries its own risks, and is financing, not diversification.
Variable prepaid forward — Cash today against shares delivered later, within a floor and cap on price.
// BOX SPREAD
Synthetic financing — Borrow through SPX options at near-risk-free rates, §1256 60/40 treatment — a fixed-term, portfolio-margin obligation, and a clear “not DIY” tool.
// SBLOC
Pledged asset line — A line of credit secured by the portfolio. Simpler and more common — but a falling share price can trigger a margin call.
// INSIDERS & AFFILIATES
If you’re an insider, the rules write part of the plan.
Company insiders and affiliates face trading restrictions that shape when and how a concentrated position can be reduced.
10b5-1 plans — A written plan adopted while you’re not aware of material nonpublic information can help create a compliant selling schedule.
Rule 144 — Affiliates’ sales of company stock may be capped by volume and reporting rules over a rolling period.
// WHY NOT TO DIY
Where smart people get this wrong on their own.
Most mistakes aren’t about picking the wrong strategy — they’re about sequencing, tax interactions, and deadlines that are easy to miss.
// TAX LOSS
Harvesting that backfires
Direct indexing losses can be disallowed if the wash-sale window or replacement trades aren’t monitored.
// TIMING
Bunching gains into one year
Selling without a multi-year plan can push the same gain into a higher bracket than necessary.
// ACCESS
Missing trading windows
Insiders may only trade during open windows — and the calendar has to match the tax plan.
// COORDINATION
Treating each tool alone
Hedging, harvesting, and deferral interact; running one tool in isolation can create conflicts.
// FIRST PRINCIPLES
— Harry Markowitz, Nobel laureate
// THE TOOLBOX
Some of the tools at our disposal
A quick comparison of the main strategies — what each does, who it fits, and how involved it is.
Options collar
Caps downside risk
Direct indexing
Harvests offsetting losses
Long/short
Harvests losses (long & short)
Exchange fund
Pools into diversified fund
§351 conversion
Tax-deferred move to an ETF
Charitable Giving (DAF/CRT)
Gives appreciated shares
Variable prepaid forward
Cash now, shares later
SBLOC
Borrows against the portfolio
Box spread
Synthetic low-rate borrowing
// NEXT STEP
An initial conversation takes 15 minutes, that's it.
