Personal Finance

30 Years Ago I Bought Apple Stock And Now It's Worth $2.5 Million. Is That Enough To Launch My Retirement?

David Beren

Published: March 15, 2025 12:04 pm

As with many individuals trying to live in the FIRE (financial independence, retire early) world, there is always a question about the best path forward. The hope is that by working hard early on in life, there will be an opportunity to retire comfortably without worrying about a 9-5 for the rest of their life. 

This is the exact case with one Redditor posting in r/ChubbyFIRE, who is, at 55, hoping to retire in 5 years according to a post in r/ChubbyFIRE. The biggest challenge for this individual is that they are sitting on $2.5 million in Apple stock, purchased 30 years ago. 

According to this Redditor, the big concern here is capital gains, and while they would like to fund their retirement with this stock, they are looking for the best ways to limit their losses. 

The Scenario 

According to the Redditor, we know that they are 55 years of age to retire when they turn 60. As it stands today, they have $600,000 spread between a 401(k) and IRA and two rental properties worth a combined $700,000 that will be paid off in the next five years. 

In addition, they currently live in a $800,000 home with an outstanding $200,000 mortgage. However, the real crux of this matter is that they have approximately $2.5 million in Apple stock purchased 30 years ago, so it’s just waiting for capital gains. 

The big concern is if they want to use this Apple money to live on during the first five years of retirement, what are the best ways to limit their modified adjusted gross income (MAGI). 

Unsurprisingly, the Reddit commenters come out in force with various opinions and scenarios that would help this Redditor achieve his goal of limiting the tax losses. Of course, what we learn in the comments is that the Redditor is worried about qualifying for ACA subsidies because their MAGI will be too high. 

Ultimately, this seems a little counterintuitive for someone with this net worth as they are worried about subsidized government healthcare. In other words, they hope to find a way to save $20,000 annually on ACA premiums. Their concern is that if they sell all at once, they will lose around $500,000 in taxes. 

The Next Steps

Look, I’ll be honest here and say that this Redditor needs to live in reality and stop focusing on ways that allow them to save on ACA subsidies, which seems complicated. Instead, the focus needs to be on minimizing the tax implications with Apple and if the ACA subsidies are possible, that would be just the cherry on top. 

Sell Shares Gradually

Selling the entire $2.5 million in a single year would push this Redditor into the highest tax brackets, so that idea is immediately out. However, spreading the sale out over 10 years ($250,000 per year), would allow this Redditor to remain in a lower tax bracket. 

There would also be a bonus that this would avoid triggering the Net Investment Income Tax, a 3.8% surtax that would apply to this Redditor if his MAGI is over $200,000 as a single filer or $250,000 for someone married, filing jointly. 

One Redditor tried to figure out the cost basis here, but if the original poster does that on their own, they only need to sell enough each year to stay below any key income thresholds. 

Leverage a Charitable Remainder Trust

Another potential option for the Redditor to help reduce tax concerns is to leverage a Charitable Remainder Trust. This comes up a few times in the Reddit comment section, and it’s likely a strong option to consider. 

Using this method would allow the Redditor to transfer Reddit stock into a CRT that would let him sell it tax-free, and then spread the gains over time. For example, if he were to contribute $1 million into a CRT, the trust would then sell it and he would receive an annual payout for life, or a set term, which could directly allow him to stay under a certain income level, even one that still allows for ACA subsidies. 

Tax-Loss Harvesting

This approach isn’t mentioned in the Reddit thread, but it’s another option for the original poster to consider. The Redditor doesn’t mention any other holdings, but if he does have them, he could sell those to offset the gains from any sale of Apple stock. 

For example, if he had a $50,000 loss on another stock and sold $100,000 of Apple stock, the MAGI would be lowered to just $50,000, which means staying in a lower tax bracket. This strategy is best for anyone with a more extensive portfolio, so it might not be completely applicable here, unless there are more holdings the Redditor doesn’t directly mention.  

The Best Approach

It takes only a few seconds of looking at the comments here to realize that the Redditor’s hope of saving any money with ACA is a foolish opportunity. Anyone with this level of a net worth shouldn’t be trying to bend the system to save on subsidies. 

However, to each their own. One Redditor puts it perfectly when they say rolling over to an IRA equals more taxes plus high risk. Selling the stock also comes with significant tax burdens, and even getting a loan on the assets, so it’s not income, also comes with high risk and interest. 

One Redditor puts it best when they say that the “ACA is penny-wise, pound-foolish” with the numbers the Redditor presented. Unfortunately, there doesn’t seem to be an avenue that gets this Redditor to the exact spot he wants. 

Of course, we still haven’t factored in the RMD needs that will occur with some of the other accounts this Redditor mentioned when he hits retirement age. Needless to say, the best course of action is arguably to sell the shares gradually, spread the tax hit out over several years, and stay in a lower tax bracket.