How Much Company Stock Should You Sell After the IPO? The Post-IPO Divestment Playbook

“I’ll Sell Some at X” Is Not a Plan

After hundreds of meetings with shareholders holding concentrated positions, one question comes up more than any other.

How much do I sell, and how much do I keep?

And one answer comes up more than any other: “I’ll sell some when it hits X.”

It sounds disciplined. Then the stock gets to X. There’s a new headline. A new valuation. A new conversation. And suddenly X becomes X plus 20%.

Most sell strategies come in one of two shapes: a schedule that ignores the stock, or a price target that ignores your life. The Post-IPO Divestment Playbook replaces both with rules that are written before the first share unlocks, so the decision is made before the headline, before the trading window, and before the stock price starts negotiating with you.

What the Post-IPO Divestment Playbook Is

The Post-IPO Divestment Playbook is a rules-based framework for divesting out of concentration without giving up the ride.

If you hold significant equity in SpaceX, Anduril, Anthropic, Databricks, or another high-growth technology, AI, space, or biotech company, the name changes. The problem does not.

Three principles run the whole thing:

• Rules, not emotions.
• Triggers, not targets.
• Secure the base, let the rest ride.

Four steps make the move: define your Secure Number, set your Ride Band, write the rules, then automate and review. It all lands on one signed page.

The Playbook, the worksheets, and the Playzone stress test are free. No account to open. You do not need to become a client. Download the Divestment Playbook here.

Step 1: Define Your Secure Number

How many dollars, outside the stock and after tax, would make you feel secure?

That is your Secure Number. Not a price. Not a valuation. Not a percentage of your position. A fact about your life, and the one number in the plan the market cannot move.

It is built from three buckets:

Obligations. The April tax bill, anything with a due date, and 12 to 24 months of cash reserves. Non-negotiable, funded first, always liquid. If you hold SpaceX RSUs, the SpaceX RSU Tax & Withholding Gap Calculator shows how large the tax piece can get.

Life goals. The down payment. Debt paid down or off. The purchases and plans you have been deferring.

Comfort capital. The cushion that lets you watch the stock fall 50% without touching the plan.

Add them up, after tax. Rough numbers are fine to start.

Every Share Has One of Two Jobs

Once you know your number, every share in your position has a destination.

The Secured Asset Base. Dollars out, diversified, after tax. Enough to fund your goals and cover every due date. The investor’s balance sheet, built one sale at a time.

Ride Capital. What stays in, deliberately sized so it still matters if the company keeps climbing. The worker’s conviction, kept on purpose.

The plan is complete when the asset base is full. Not when the stock hits a price.

Step 2: Set Your Ride Band

Your Ride Band is the share of your portfolio you choose to keep in the company once the base is secured. A range, picked deliberately, in writing, before the first share is sold.

Set it too low and you spend the next decade doing the math on the run you missed. Set it too high and you are still betting your family’s security on a single name. The band exists to keep both regrets small.

The shares inside it are not leftover concentration you failed to sell. They are ride capital: conviction converted into a deliberate position.

Use this gut check: at the top of your band, if the stock fell by half, would anything your family needs be touched? If yes, the band is too high.

When the band feels wrong, in a run or a drawdown, it is doing its job. A number written calmly outranks one that occurs to you during a headline.

To see how concentrated you are today, run your numbers through the SpaceX Concentration Risk Analyzer or the Anthropic Concentration Risk Analyzer.

Step 3: Write the Rules

The Playbook uses two engines to sell down to your Secure Number, both tied to valuation.

Engine 1: The monthly trim (runs on the calendar). A small, fixed percentage of shares sells every month. The rate is set by valuation: faster as the stock climbs, slower as it cools, and a full stop below your floor. The floor is a valuation you set in advance. Below it, the trim holds. No exceptions.

Engine 2: The milestone ladder (runs on strength). Each time valuation clears a pre-set rung, a fixed-dollar tranche sells. Each rung is a valuation you would genuinely celebrate. Because tranches are sized in dollars, not shares, every rung cleared means a known amount lands in your base. The decision was made when the ladder was written, not in the moment.

Both engines sell into strength and pause in weakness, automatically. That is the working definition of investor behavior: action by rule, not by mood.

Two Clocks: Price and Calendar

Not every sale should wait on the stock.

The price clock. Comfort capital and upside trimming answer to valuation rungs. If the market stalls, these sales wait, for as long as it takes. Delay is a feature, not a failure.

The calendar clock. Anything with a due date, like April’s tax bill or tuition, is funded by the deadline at whatever the price happens to be. These sales never wait on a rung.

Never leave a dated bill hostage to a price target. Deadlines outrank rungs. It is the one override the plan allows, and it runs in one direction only: toward security.

Step 4: Automate and Review

Rules only work if they survive contact with a scary week. The Playbook builds in five guardrails:

• A fill anywhere inside the band counts. Every trigger executes inside a range, not at a single price. Chasing an exact print is how tranches get missed by pennies.
• Written and signed. Numbers, rungs, rates, and dates go on paper before liquidity arrives. Ambiguity is where discipline leaks.
• Automated. Standing orders execute the tranches, not willpower.
• No headline overrides. News is never a trigger. If it is not a rung or a due date, it does not sell a share, up or down.
• Scheduled reviews only. Rules change at set review dates, after a 30-day cooling-off period. A new child should get in. A scary Tuesday should bounce off.

All of this operates inside the real constraints every post-IPO shareholder faces: lockups, trading windows, blackout periods, and your company’s insider trading policy. In most cases, the rules should be coordinated with those policies and with your tax professional.

Unlock Day: The First Decisions Are the Biggest

Not every lockup waits for day 180. Some companies, SpaceX included, release shares in stages before the lockup fully ends, at set dates with set percentages. The staging changes the calendar, not the rules. Whatever unlocks, the plan decides what sells.

Before unlock: arrange access before you need it. A line of credit against the shares can go live the moment they land in the account. It typically costs nothing until drawn, and it means a closed trading window never forces a bad sale. Borrowing against a concentrated position carries its own risks, including collateral calls if the stock falls, so it should be sized conservatively.

At unlock: the opening tranche, with a line in the sand. Sell a lump sum at anything above a floor you set in advance, sized to the tax bill, reserves, and near-term goals. A floor says “never below,” not “wait for more.”

From then on: the engines take over. Monthly trims and milestone rungs run everything. No further day-one decisions exist, because none were left to make.

The first April after your sales begin is the largest dated obligation most shareholders face. The opening tranche funds it early, and the cash sits in Treasuries until it is due. Whatever else the stock does in year one, that bill is boring.

For SpaceX-specific timeline context, see SpaceX Is Now $105 a Share. The IPO Just Got Real.

A Worked Example: One Plan, Start to Finish

Here is how the Playbook looks filled in for one hypothetical SpaceX shareholder. Every figure is illustrative, and none of it is a recommendation.

• Position: 76,790 shares, worth approximately $11.5 million at a $2.0 trillion valuation
• Secure Number: $4 million to $5 million, after tax, outside the stock
• Ride Band at plan completion: 30% to 60% of the portfolio, roughly 40,000 shares

If not a single share sells, that stake is worth approximately $8.9 million at a $1.5 trillion valuation and $17.4 million at $3.0 trillion. The upside is real in every direction. So is the exposure.

The monthly trim, filled in

Valuation	Monthly Rate	Approx. Monthly Sale
Below $500B	HOLD	None
$500B to $1.0T	0.25% of shares	$28,796
$1.0T to $1.5T	0.50% of shares	$57,593
$1.5T to $3.0T	1.00% of shares	$115,185

At a $2.0 trillion valuation, the trim runs at 1.00%: roughly $115,000 a month of automatic diversification. Nobody picks a day. Nobody reads a headline first.

The milestone ladder, filled in

Trigger	Execution Band	Tranche	Secured After Tax (Cumulative)*
First unlock	None	$850,000	$654,500
~$1.50T	$1.45T to $1.55T	$850,000	$1,309,000
~$1.75T	$1.70T to $1.80T	$850,000	$1,963,500
~$2.00T	$1.95T to $2.05T	$600,000	$2,425,500
~$2.25T	$2.20T to $2.30T	$600,000	$2,887,500
~$2.50T	$2.45T to $2.55T	$600,000	$3,349,500
~$2.75T	$2.70T to $2.80T	$700,000	$3,888,500
~$3.00T	$2.95T to $3.05T	$700,000	$4,427,500
~$3.25T	$3.20T to $3.30T	$700,000	$4,966,500

Cumulative, after federal long-term capital gains tax only. State income tax, including California’s, would reduce these figures further, and results depend on holding periods, basis, and your specific circumstances.

The Secure Number clears between the $3.00T and $3.25T rungs on the ladder alone. In practice, the monthly trim runs alongside the ladder and typically gets there a rung or two sooner.

What actually sells at unlock

In this example, roughly $2.3 million of stock becomes sellable at the first unlock. The plan sells about $970,000: the opening tranche, sized to the tax bill, reserves, and near-term goals, executed above a floor set in advance. By the time the lockup calendar fully opens, planned sales total about $1.4 million, roughly 12% of what is available.

The calendar opens faster than the plan sells. Availability is never the trigger. The rules are.

How Long Does the Plan Take?

The honest question about any selling plan: what if the stock goes nowhere?

Before signing, you run your position through the Playzone: the bull case, the stall, and the drawdown. You are looking for one thing. Does the plan still work? In the Playbook’s framework, there are three paths to one destination. Only the timeline changes.

• Bull run. Rungs clear early and the ladder does the heavy lifting. Roughly 2 to 3 years.
• Base case. Steady trims plus the occasional rung fill the base. Roughly 3 to 4 years.
• Stall. No rungs clear, but the trim keeps filling, and anything with a due date funds on the calendar regardless. 5 or more years, never derailed.

And in a drawdown below your floor, the trim stops, the rungs wait, and only dated obligations sell. That is the point of funding the first April early.

SpaceX shareholders can also model diversification paths in the SpaceX IPO Diversification Simulator.

Know What “Done” Looks Like

Most selling strategies never define completion. This plan ends when three things are true:

• The Secured Asset Base is fully funded, after tax.
• The position sits inside your Ride Band, the exposure you chose in writing.
• Every dated obligation is covered through next April.

From that day forward, you are no longer unwinding a concentration. You are managing an allocation.

You can let it ride, because nothing you need is riding on it.

The Part Nobody Can Engineer Away

At some point, you are going to sell shares and watch the stock keep climbing. Or you will hold shares and watch them fall.

There is no framework that makes you right every time. So the Playbook was not built for perfect. It was built for participation. Every sale is partial. Your Ride Band keeps you participating in the upside. Your Secure Number keeps what you actually need from depending on that upside.

The goal is not to eliminate regret. The goal is to make sure regret cannot derail the plan.

Why This Is Really a Worker to Investor Decision

You spent years earning equity in one company. The worker earned the shares. The investor decides what they are for.

Work → Equity → Wealth

At some point, part of that wealth needs to become independent of both. An asset base outside your company: capital that can compound, fund your life, and create options, and that keeps working regardless of what happens to one stock.

That is the move from Worker to Investor. The Worker to Investor framework lays out all three levels. Once your asset base reaches critical mass, it can sustain your lifestyle without additional stock appreciation or employment income. Find that number with the Critical Mass Simulator.

And here is the irony. The more you secure outside the stock, the easier it becomes to let the rest ride.

Build Yours

Your version of the plan on a page is four worksheets away: your Secure Number, your Ride Band, your trim tiers and floor, and your milestone ladder.

• Download the Divestment Playbook and worksheets
• Watch the full video walkthrough
• Explore all free equity calculators (no login required)

If you hold SpaceX equity, the SpaceX IPO Planning Guide and the SpaceX Worker to Investor page cover the rest of the picture. For the full framework across every company we serve, start at the Worker to Investor hub.

Your Equity Built This Far. Strategy Protects What Comes Next.

You already earned the position. The hard part is done. What happens next depends on the rules you write before the market asks you to decide.

Fill in the worksheets, rough numbers welcome, and bring them to a conversation. Thirty minutes will show you where you stand in the context of your complete financial situation.

Talk to Derek →

Augustus Wealth, LLC is a registered investment adviser. Advisory services are only offered to clients or prospective clients where Augustus Wealth, LLC and its representatives are properly licensed or exempt from licensure. This content is for informational and educational purposes only and does not constitute personalized financial, tax, or investment advice. All examples are hypothetical and all figures are illustrative. Equity compensation strategies involve risks and should be evaluated in the context of your complete financial situation. Borrowing against securities involves risk, including the possibility of collateral calls. Tax laws change frequently. Consult your tax professional for advice specific to your situation. SpaceX, Anthropic, Anduril, and Databricks are referenced for educational purposes only. Augustus Wealth has no affiliation with SpaceX, Anthropic, Anduril, or Databricks. Calculator outputs are estimates and should not be relied upon as tax or financial advice. Past performance is not indicative of future results.