Why Most of My SpaceX Clients Didn't Sell The Max They Could on Lockup Release Day.

The day the lockup opened

On August 6, the first 20% of SpaceX's locked-up shares became sellable. The stock had been cut roughly in half from its first-week high, hitting a low of around $105.

That's $135 IPO price. $225 peak. And now at lockup release morning ~$110.

The headlines were rough. Investment Banks published notes stating plenty of investors expected the stock to slide to $100 as the lockups rolled off; and online people were calling for $50.

For most of my clients: selling did occur on lockup release day at ~$110. But only for a portion of their 20% of released shares, as lockup release day was one of many on a schedule (most typically weekly selling over 6 months). Not one big click on the worst-looking day of the year.

This article is about why I built plans for clients that way. And it's also about when we don't — because a selling schedule is a tool — and like everything in personal finance, it's personal and unique to the individual.

A selling schedule across three buckets

Every selling plan I build answers three questions. Not one. Three.

1. Sell Now— How much do we get off the table pretty quickly? This is the money tied to real life needs and goals: taxes owed, a house, debt, the emergency fund, the stuff that can't ride on one stock. And also a lot more if clients don't feel good about the company's business prospects.

2. Sell Over Time— How much do we sell on a schedule over the next few years? This is the bulk of the diversification work.

3. Keep Long-Term— How much do you hold because you genuinely want to? This one gets a written thesis. If you can't write down why you own it, it isn't a long-term holding. It's inertia....

The unique part here is that the schedule isn't just bucket two. Even the "sell now" bucket gets a schedule. Even the shares a 10-out-of-10 believer trims get a schedule.

How the schedule actually works

Most of the time, the schedule is dead simple: a fixed number of shares, sold on a fixed calendar. Same count, same cadence, regardless of what the stock did yesterday.

What changes is the speed.

• Sell Now: Weekly Candence typically over 2-6 months

• Sell Over Time: Monthly Candence typically over 2-4 years

• Keep Long Term: The shares we do opt to sell are still scheduled, typically monthly, and the plan is revisited frequently

So for a lot of my SpaceX clients, the plan looked like this: work through the Sell Now amount week by week over about six months after the August release (and the smaller tranches that followed it). Once that's done, downshift to monthly sales that run for a few years. Same concept. Different gear.

Why shares most times vs dollars? This one's a little nerdy, but it matters. If you sell a fixed dollar amount each time, you're forced to dump more shares when the price is low and fewer when it's high. That's OK and I do that at times with clients (it's a "tool in the tool-belt"). But for most people the same amount of shares every week makes the most sense.

There are other ways to build bucket two (e.g. dollar targets). I covered those in the 3-bucket selling plan material. But for most people, the simpler, boring version wins. Boring is easy to stick with.

A reminder that personal finance is weird sometimes

Before we dive deeper, it's helpful to remind that personal finance is a unique thing. It blends together finances, circumstances, personal goals and psychology. And because of that it results in choosing the NON-optimal path at times.

For example, I have a favorite analog I like to use with clients called "the world's dumbest casino". At the world's dumbest casino, they only have one game (a dice game) and the rules are simple:

• You roll a normal 6-sided dice. If it's a 1-5, you double your money. If it's a 6 you lose it all (as noted, "dumbest casino")

• But there is one unique catch to: You can only play the game one time, and you need to bet your entire net worth

Mathematically, you absolutely want to play the game; 83% odds you double your money vs. 17% odds you lose it.

But no matter whether your net worth is $100,000 or $100,000,000, losing every penny would hurt SO much more than doubling it would improve things. And when I chat with clients about the casino, around 80% tend to agree (saying they would not roll the dice if given the chance).

Here is why we opt for a schedule vs all at once

Finance PhD research makes it abundantly clear that when you have a concentrated holding you're better off selling immediately and diversifying vs pacing sales out.

So why do I fly in the face of that and use selling schedules with almost every client with a concentrated holding? Because you get ONE CHANCE at this

For most of my clients in this position, the concentrated position comprises the majority of their net worth. And they will only ever have this happen once in their lifetime.

They don't want to "screw it up", and most vacillate between "fear of not selling and it going down", but also "fear or selling and it going up." I was lucky enough to be in their shoes (I experienced 2 IPOs when I worked in tech); I absolutely get the gut wrenching that goes on

When you have a selling schedule, a good way to think about it is "you'll get roughly the average stock price over X weeks/months vs. whatever the price is the day you sell." When you navigate this once in your life, you don't want to have regrets about how you did it. And knowing that the stock price could do anything (be up a lot, down a lot, or stay flat-ish), committing to a selling schedule, and thus an average price over the time period...psychologically that wins for the vast majority of people.

So even if a selling plan is financially sub-optimal, it's an AMAZING way of managing potential regret, and regret is a different animal than risk.

Because when you choose to sell it all (or a very large chunk) on one-day...you have to be right about that day.

In the case of SpaceX: Sell everything at $110, watch it run to $150 within a few weeks, and that decision and button click will live rent free in your head for years.

But with a selling schedule:

• If the stock goes up, you're still holding unsold shares that participate. You feel good.

• If the stock goes down, you already got some off at higher prices, and you're still selling. You feel okay.

• If it chops sideways, you get roughly the average. Nobody loses sleep over the average.

None of those outcomes are perfect....but very importantly, none of them are the outcome you can't live with.

That's the whole game. Not maximizing. Minimizing regret — knowing we're never going to get it perfect.

And this applies even on short timelines too. Selling the Sell Now bucket over a few months instead of one afternoon is a seemingly small change on paper. But psychologically it's a completely different experience.

The 0–10 question I work through with every client

Before we pick a pace, I ask every client one question: on a scale of 0 to 10, how do you feel about this company as an investment, and why? Ten is "I'd bet my career on it." Zero is "get me out."

Their answer changes the plan more than almost anything else.

Conviction 0-5:

• The Plan: Exit quickly and redeploy into other things

• Schedule: We may not use one, or if we do it's a very rapid one (sell the same amount every day over 2 weeks)

Conviction 6-8:

• The Plan: Meaningful Sell Now, multi-year Sell Over Time, modest Keep

• Schedule: Yes — this is the sweet spot

Conviction 9-10:

• The Plan: Smaller sales, much bigger Keep bucket with a written thesis

• Schedule: Yes, for whatever gets sold

If you're a 5 or below, we sell very quickly, though potentially still with a schedule (albeit a super quick daily one over 1-2 weeks). If you're bearish on the company, it's a recipe for slow-motion regret. The schedule's main psychological benefit only works if you're comfortable owning the unsold shares in the meantime. If you're not, we sell much faster and put the cash to work elsewhere.

If you're a 6, 7, or 8, you're where most of my clients land. You understand price risk is real. You understand the plan can take you in any direction. But you're not trying to run for the exit, and you're not losing sleep over the shares still waiting their turn. This is where a schedule earns its keep for both the "Sell Now" (over 2-6 months) and the "Sell Over Time" (typically 1-4 years).

If you're a 9 or 10, the conversation is mostly about the Keep bucket — how big it is, and why. We still sell something, often a smaller amount, to start building the discipline of taking capital off the table. And yes, those sales go on a schedule too.

One thing I watch for: conviction scores tend to drift with the stock price. A 9 at $225 can become a 6 at $110. That's exactly why we write the score — and the thesis — down before the volatility hits. I was an equity analyst who wrote the Buy/Sell/Hold reports on companies for the better part of a decade, so I have the experience to bring to the table here. The final decision is of course 100% yours. But if you have a weak thesis we really probe on that because I've seen that turn ugly for a lot of folks.

How it played out for SpaceX folks (answer = they're happy)

If you measure this by average financial price achieved, those opting for a selling schedule did well. The lockup day turned out to be close to the low, not the start of a slide. SpaceX rose ~33% in August and added ~4% more in September, closing September around $150. Higher selling prices = higher average selling prices.

But honestly, that's not the part clients bring up. What they bring up is how it feels. And they feel really good with the plan they have in place, and we're on track to diversify the right amount and set them up very strongly for their financial future!

The obvious question you'd ask: Are you full of shit and clients only feel that way because it's up? What about if it fell to $75?

Honest answer = I can't say for sure because that didnt happen. But what I can say is we DID model that scenario. And discuss it. And everyone knew it was a very plausible risk and still felt much better with the weekly selling plan.

That's the difference between the outcome and a "verdict" on the plan. The stock bouncing doesn't make the plan smart. The plan was smart because the client could live with every version of what happened next.

And to be clear -- this was NOT the easy route. Weekly trades, some sending company back office issues regarding shares/cost basis details that paused some clients selling, frequent tax-lot adjustments each week — it's a lot MORE work for my clients and for me than one big sell order. But the feedback from clients is pretty universal in that it was worth it. And that's why we did it (and will do it again for other clients with future appreciated positions; Anthropic, OpenAI, Databricks, Stripe, etc.)