By Aaron Marks, Founding Partner & Chief Strategy Officer
When “Up and to the Right” Creates a New Problem
If you’re an employee or former employee holding SpaceX shares, you may be thinking: Why sell? It’s been the right decision so far. And you might be right.
But here’s the planning reality: when a single investment grows large enough, it can quietly become your largest financial risk—even if you still believe in the company.
At Amplius, we’re big believers in a balanced approach—not because it’s exciting, but because it’s what tends to work over time.
Step 1: Find a Sounding Board (Not an Echo Chamber)
When a stock is climbing, everyone has an opinion. The difference is whether you’re hearing:
- An echo chamber: the same “never sell” message bouncing back from every angle
- A sounding board: someone who can pressure-test your thinking, bring different perspectives, and help you make a decision you can live with
This isn’t about pessimism. It’s about clarity.
Step 2: Identify Your “Unfunded Liabilities”
Most investors think about returns. Financial planning forces a different (better) question:
What future goals do you need to fund?
Examples:
- Retirement timeline and lifestyle
- College funding
- A home purchase or renovation
- Supporting family, parents, or charitable goals
Those are real liabilities—future checks you’ll need to write. One way to reduce stress is to use part of a great outcome (a rapidly appreciating stock) to fund real-life goals.
Step 3: Remember: Selling Isn’t All-or-Nothing
A common mental trap is: Either I sell everything or I sell nothing.
In reality, many smart strategies look like:
- selling a small percentage to fund goals
- setting a measured plan (e.g., staged sales over time)
- reducing concentration risk while still keeping meaningful upside exposure
Yes, if the stock keeps soaring, you may “miss” some upside on what you sold. But you also gain something most investors undervalue: security and flexibility.
Step 4: Plan the “Before” (Tax Moves That Make the Sale Better)
This is where the planning gets real—because it’s not just “should I sell?”
It’s:
- How much is right?
- What’s the tax impact?
- Can we reduce taxes with timing, gifting, charitable strategies, or coordinating with your CPA?
- Are there opportunities to align sales with years when income is lower?
Amplius’ philosophy is to focus on what you can control—including tax efficiency—because what matters isn’t only what you earn, it’s what you keep.
Step 5: Plan the “After” (Reinvesting + Tax-Loss Strategy)
After a sale, the next questions matter just as much:
- Where should the proceeds go?
- How do we rebuild your portfolio so it reflects your goals—not just your employer’s stock chart?
- Can we generate tax losses elsewhere to help offset gains?
This is where a “balanced, boring approach” can be a superpower: disciplined investing, aligned to your plan, with tax-aware implementation.
Bottom Line
If you’re eligible for a buyback—or eventually an IPO—don’t treat it like a one-time event. Treat it like a financial planning decision with steps before and after.
If you want a sounding board, we’d be happy to help.
FAQs: SpaceX, Buybacks, and “When Should I Sell?”
Q: Should I sell my shares before an IPO?
A: It depends less on guessing the IPO date and more on your plan. At Amplius Wealth Advisors, we help you look at your goals and your overall risk—then decide if selling a small portion now (or in a buyback window) helps you lock in progress without giving up the whole upside.
Q: How much of a concentrated position should I sell?
A: Most people don’t need an all-or-nothing decision. At Amplius, we help you pick a “right-sized” amount by tying it back to real goals (retirement, college, a home) and how much risk you’re comfortable having in one stock—often using a phased approach.
Q: How can I reduce taxes when I sell?
A: Taxes are often the difference between a good sale and a great one. At Amplius, we help you think through the moves before you sell (timing, coordination with your CPA) and the plan after you sell (reinvesting tax-smart and looking for ways to offset gains).