04
Equity collar
Cap downside (and upside) on a stock by using options. Allows you to protect your stock from downside risk while gradually diversifying over time.
Downside floor while plan runs
Is your future resting on one or two stocks?
Diversify without overpaying in taxes. Five questions. Two minutes.
FiduciaryRegistered Investment Advisor
Inverse AI
2 min · No accountInformational purposes only. Not investment, tax, or legal advice. All investing involves risk, including loss of principal. Responses are generated by an AI model and reflect simplified inputs; your actual situation depends on factors not captured here.
Managing wealth for leaders at
CoinbaseMetaAT&TUniphoreTerret.AINew RelicCiscoBlock
The cost of holding
Selling is expensive. So is doing nothing.
Most investors default to "wait and avoid the tax." History suggests that's its own kind of expensive.
64%
In one stock
Does your portfolio look like this? Most people in this situation sit between 50% and 75% in a single name — usually their employer's stock.
One stock 64%401(k) 12%Real estate 10%Savings 8%Investments 6%
-70%
The potential downside
Roughly two-thirds of tech companies have had a permanent 70%+ drop from their peak.
They never recovered.
Source: JPMorgan Asset Management, "The Agony & The Ecstasy: The Risks & Rewards of a Concentrated Stock Position," 2024 edition.
Illustrative scenario
Sell it the old way.
Or save hundreds of thousands.
Work with experts who do this every day.
Composite illustration
$1.4M in stock. $1.2M in gains. What's the smartest way out?
Meta Staff Engineer · California · top federal bracket
Option 1Sell it allTax paid$474,880
Option 2Use an expert strategyTax paid$179,880
The difference
Roughly half the tax.
~$295K
illustrative savings
What an expert strategy looks like
~40%
Into an exchange fund. Pulls a meaningful slice of the position into a diversified pool without selling it. No tax event today; full diversification on that slice for 7+ years.
~30%
Into a long/short direct indexing SMA. Builds a diversified portfolio in parallel that systematically books tax losses on individual stocks. Over 5–7 years, those losses can wash significant gains on a tax-neutral basis as the rest of the position is sold down.
~20%
Contributed to a donor-advised fund. Eliminates the tax on that slice entirely. Provides a current-year deduction at fair market value, with grants directed to charities on the holder's own schedule.
~10%
Retained with a protective collar. Caps the downside on what's kept while the rest of the plan runs. Position stays intact; tax bill stays at zero on this slice.
Illustrative scenario built from current tax assumptions and representative strategy mechanics. Not a representation of past performance, not a guarantee of outcomes. Actual plan and results depend on inputs not captured here. Talk to an advisor to build your plan.
The toolkit
Five strategies. Most situations call for combining several.
The right answer depends on your stock position, timeline, and goals. There is no one-size-fits-all.
01
Exchange funds
Contribute your stock into a pooled private fund alongside other investors. You receive a diversified basket of stocks back after 7 years. No sale, no tax event today.
Tax deferred for 7+ years
02
Long/short direct indexing SMA
A strategy designed to generate tax losses while getting returns similar to an index such as the S&P 500. Over 5–7 years, those losses can wash away gains from selling down your stock position.
Significant gains washed tax-neutral
03
Tax-loss harvesting via direct indexing
Mirrors an index like the S&P 500 while booking tax losses on the individual stocks inside it. Simpler than the long/short version, with smaller harvesting yield.
Foundational layer
05
Charitable strategies
Donating appreciated stocks to charity via a Donor-Advised Fund (DAF) or Charitable Remainder Trust (CRT) eliminates the tax entirely, while giving you an income tax deduction (and additional benefits).
Tax on contributed slice: zero
Sumeet Ganju
Founder · InverseWealth
Fee-onlyFiduciaryCA-Registered RIA
Who you're actually talking to
The diagnostic is by AI. The plan is human.
Sumeet founded InverseWealth in 2024 after a decade as a tech CPO and VP. The firm helps tech professionals, business owners, and high earners build long-term wealth — specializing in tax mitigation, risk management, and powerful investing strategies.
Inverse AI runs your numbers in seconds because that's what software is good at. An actual plan, however, requires much more. Your stocks don't sit in isolation. Your goals, other investment assets, and life situation all affect the strategy.
Talk to Sumeet to figure out the best strategy for you — your wealth is too important to be left to chance.
Talk to SumeetThirty minutes. Fiduciary. He'll tell you if you don't need him.
Questions that come up
A few things people ask.
Is this advice?
No. The diagnostic produces educational illustrations based on simplified inputs. It's not personalized investment, tax, or legal advice. The actual planning happens inside a fiduciary engagement with Sumeet — that's where your specific situation gets analyzed against your full financial picture.
Do I have to give my email or pay anything to use the calculator?
No to both. The calculator runs the numbers without an account. Email is only requested later, in exchange for a written summary of your scenario you can keep. Nothing is paid; nothing is sold to data brokers; nothing is shared with partners.
How is this different from Wealthfront or Betterment?
Wealthfront and Betterment are excellent for managing a diversified portfolio you already have. They aren't built for the specific problem of unwinding a single concentrated position with significant embedded gains. The work most concentrated holders actually need is combining several mechanisms in the right order, for the right slices of the position. That's what InverseWealth specializes in.
Two paths
Run the numbers before you make the move.
You've read this far. Probably worth two minutes to see what selling actually costs you — and what you don't have to pay.