At some point, the question isn’t whether Google can keep going up.
It’s whether you still need this much of your financial future depending on it.
Imagine you’re still working at Google.
You’ve accumulated about $6 million outside your home. Roughly $2 million is Google stock.
You still have a mortgage. You have two kids. Retirement isn’t happening tomorrow, but you can see it from here. Maybe you’d like work to become optional sometime in the next ten years.
Google stock has been very good to you.
So what do you do with it?
We can talk about capital gains. Collars. Variable prepaid forwards. Charitable strategies. There are plenty of ways to manage a concentrated position, and some of them can be useful.
But I wouldn’t start there.
I’d start with a different question:
How much of this Google stock do you actually need to keep taking risk with?
Start with what you already have
In this example, Google represents about one-third of the family’s $6 million investment portfolio:
$2 million in Google stock
$4 million in everything else
About ten years before retirement
Thirty-three percent in one stock is meaningful.
But that doesn’t automatically mean, “Sell it all.”
This family has something valuable: time.
They’re still earning. They’re still saving. The mortgage should continue coming down. The other $4 million can continue compounding.
And if one spouse still works at Google, more Google stock may be coming.
That gives us choices.
Suppose our planning shows that this family needs approximately $5 million of diversified investments by retirement to support the life they want.
They don't have $5 million outside Google today.
They have $4 million.
But they also have another decade to invest, continued earnings and the ability to save.
It’s entirely possible that the diversified side of their balance sheet eventually provides most, perhaps all, of what they need.
If that's true, the question changes.
It’s no longer:
“Can we afford to sell Google?”
It becomes:
“If we’re already on our way toward enough, what are we asking the additional Google risk to accomplish?”
Your Google exposure may be bigger than $2 million
There’s another wrinkle if you still work there.
The Google stock in your brokerage account is only part of your connection to Google.
Your paycheck comes from Google.
Your Prosper rewards letter may include new RSU refreshers on top of shares already scheduled to vest over the next several years.
And $2 million of your existing wealth is already invested in Google.
So you can be doing something that seems contradictory:
Diversifying Google stock today while accumulating more Google stock tomorrow.
There’s nothing necessarily wrong with that.
But it means I wouldn’t look at concentration as simply “Google is 33% of the portfolio.”
I’d also want to know what’s coming.
How much Google stock do you own today?
How much is already scheduled to vest?
What might future refreshers add?
For someone approaching retirement, the answer may not be one giant sale. It may be building a process for what happens to Google stock, existing shares and new RSUs, over the next ten years.
You don't have to solve this on Tuesday afternoon
One of the false choices with concentrated stock is:
Keep it or sell it.
There’s a lot of room between those two answers.
Maybe 33% eventually becomes 25%.
Then 20%.
Maybe someday it’s 10% or 15%.
New RSUs could be sold as they vest while older, low-basis shares are handled more deliberately. Sales could be spread across tax years. Appreciated shares could potentially be used for charitable giving if giving was already part of the family's plan.
There are trade-offs to all of those decisions.
Selling creates taxes.
Keeping the stock preserves the possibility of additional upside.
And Google could absolutely continue outperforming.
That's why I don't think the goal should necessarily be to eliminate Google stock.
The more useful question is how much Google exposure still makes sense for this particular family.
The destination matters.
So does the path.
A family ten years from retirement may have the luxury of getting there gradually.
When does complexity actually help?
Sometimes a more sophisticated concentrated-stock strategy deserves consideration.
A variable prepaid forward, for example, may be structured to provide upfront liquidity and hedge some downside exposure while retaining some participation in future appreciation. Its tax treatment and economics can be complex and depend on the specific structure.
That's a lot of complexity.
So I think it should solve a problem worthy of it.
If someone tells me:
“I have $2 million of Google stock and I’m uncomfortable with the concentration.”
I’m not sure my first move is a sophisticated financial product.
We have time.
We have other assets.
We may have tax-planning opportunities.
And we may have years of additional Google RSUs still coming.
But change the facts:
“We need substantial liquidity. My Google cost basis is extremely low. I don't want to recognize the entire gain this year. And a major decline in Google could meaningfully change our retirement plan.”
Now the problem is different.
We're trying to solve for liquidity, taxes and concentration risk at the same time.
That's when complexity may earn its place.
At some point, the stock’s job changes
Earlier in your career, Google stock may primarily be a wealth-building asset.
You’re working.
You’re accumulating.
Retirement is far away.
Then life changes.
There’s a mortgage.
There are kids and college.
Maybe you'd like to work less.
Eventually, retirement stops being some distant abstraction.
The money has a job now.
Some of it may need to educate two kids.
Some may need to pay down a mortgage.
Some may eventually replace a paycheck.
And some may simply need to give you the ability to say:
“I don't have to work anymore unless I want to.”
That’s why I don’t think concentrated-stock planning ultimately starts with whether Google is a good company or where its stock goes next.
Google could continue doing extraordinarily well.
The question is more personal than that.
If the $4 million you already have outside Google is on its way toward becoming enough to fund the life you want, then before deciding what to do with the other $2 million, I’d want to understand:
What are you still taking that additional risk for?
This content is for educational and informational purposes only and should not be considered personalized investment, tax, or legal advice. Each situation is unique and should be evaluated individually.