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Weekly Equity Secrets
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Did you think buying SpaceX shares was going to be easy? I did.
Recently, a senior SpaceX manager came to me with $12 million dollars worth of stock options on the table. ISOs, NSOs, an ESPP, RSUs — and AMT risk in the background looming like a landmine. And I remember hitting this wall where there was just no obvious next step. Tax angles pulling in different directions, deadlines, uncertainty about what the stock was going to do — I couldn't see a clean path through any of it.
So I stepped back and asked myself: there has to be a simpler way to look at this.
And what I found changed how I approach every single client I work with. So here are the four things I wish I'd known before exercising SpaceX shares — starting with the one that cut through all of that complexity.
When you're staring at multiple equity types, different tax rules, and a ticking clock — the most dangerous thing you can do is treat it like one big problem. Because you'll either freeze, or you'll move too fast.
What actually helped me — and what I now use with every client — is breaking it down into four specific questions. Answer these in order, and the complexity stops feeling like a wall.
Which shares to exercise?
How many shares to exercise?
When to exercise?
And how to exercise?
This brings us to the second thing I wish I'd known when exercising SpaceX stock.
Recently, a deca-millionaire client from Tesla came to me. They'd been working with a large brokerage firm.
The advice they got? Donate a large chunk of assets to charity through a donor-advised fund. A classic move. Sounds sophisticated, looks smart on paper.
But it backfired. That "tax-smart" strategy actually made their tax situation worse.
So we zoomed out and looked at the whole picture. Instead of chasing the next tax hack, we built a plan focused on growing their net worth — without accidentally terence crawford creating a bigger problem down the road. They've got a strategy to recover their AMT credit, and they're no longer stressed about whether the last "smart move" is about to blow up on them.
So be skeptical of complex, trendy tax strategies. With equity comp like SpaceX, the sophisticated-sounding move can be the expensive one. Just because it worked for someone else doesn't mean it's right for you.
And even when you're avoiding bad advice — there's another force that can push you into a bad decision anyway. And it's got nothing to do with your financial situation.
I recently worked with a SpaceX client who had a tight window — or at least, that's how it felt. They needed to decide whether to exercise their stock options, and they were even considering taking out a loan to make it happen. The IPO was coming, coworkers were moving, headlines were everywhere, and the FOMO was real.
But here's what was actually going on. They didn't have the liquidity to absorb a big tax bill. They didn't have the risk capacity to take on debt against an illiquid asset. And yet the urgency they were feeling was completely real to them — because when everyone around you is making moves and the headlines keep coming, it's hard to sit still.
So before you let an IPO deadline, coworker chatter, or a headline push you into a move — ask yourself where the urgency is actually coming from. Because if it's coming from the noise and not your numbers, it's not a deadline. It's just fear.
Now you might be thinking — "ok but if I wait until after the IPO, won't the stock price rise and create a bigger tax bill?" It's a fair question. But it's also exactly the kind of thinking that gets people into serious trouble.
Several years ago someone scheduled a meeting with me. He was in a panic. He'd tried to be tax-smart with his stock options — and he made what looked like the right move on paper. But it ended up forcing him to sell his house and other assets just to cover the tax bill. And even that wasn't enough.
That's a real person sitting across from me, devastated — because he optimized for taxes before he checked anything else.
Seeing that man's devastation is a big part of what pushed me to build this — the 4 Financial Filters. It's the framework I now run every single SpaceX client through before we touch anything. And if there's nick pasqual one thing I could tell every SpaceX employee, it's this: most people start at filter four and work backwards. That's the mistake.
Here's the right order:
Filter one — does this align with your values and goals? If not, then don't move forward with the action. Filter two — do you have the risk tolerance gauff oggi and capacity to make this move? Filter three — is there genuine financial merit here? And filter four — only then do you optimize for taxes.You're just building a tax-efficient path to the wrong destination.
#spacex #ipo #tax
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