THE FATHER BLOG

First of all, I would NEVER suggest only buying one stock. I only ask this question because I was curious with all the information and AI analysis available to us, which would be the pick. I was wrong on the answer it spit out. So while you would likely never due this, the principles behind the answer still make sense. Give a look:

If forced to pick just one equity to buy and hold forever, the single best choice is not an individual company, but a broad-market index fund like the Vanguard S&P 500 ETF (VOO).

Buying a single individual company introduces severe concentration risk. Even dominant giants can face business shifts, management changes, or structural decline over a long time horizon. However, if rules strictly require a single individual ticker rather than a diversified exchange-traded fund (ETF), my primary recommendation is Berkshire Hathaway (NYSE: BRK.B).

The Core Strategy: Why Berkshire Hathaway Fits Best

Berkshire Hathaway operates less like a standard corporate stock and more like a self-contained, professionally managed investment fund. It inherently resolves the danger of single-stock ownership by providing built-in diversification across multiple sectors of the economy.

• Diversified Wholly-Owned Subsidiaries: Berkshire completely owns over 60 operating businesses. This includes indispensable, cash-generating infrastructure like BNSF Railway, Berkshire Hathaway Energy, Geico insurance, and massive manufacturing and retail operations.
• A Fortified Public Equity Portfolio: Beyond its private holdings, a single share of Berkshire gives you fractional ownership in dozens of major blue-chip public companies, heavily anchored by massive, high-quality, cash-flow-positive businesses like Apple (AAPL) and American Express (AXP).
• Unrivaled Cash Fortification: Berkshire famously maintains a fortress-like balance sheet with hundreds of billions of dollars in cash and short-term U.S. Treasuries. This massive liquidity serves as a safety net during market downturns and allows management to aggressively buy up distressed assets at a discount when the broader market panics.

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Alternative Single-Stock Approaches

Depending on your ultimate financial goals and risk tolerance, a different single-stock framework might better fit your thesis.

Ticker / Category	Investment Style	Core Justification	Trigger to Choose This Instead
Schwab U.S. Dividend Equity ETF (SCHD)	Income & Quality Growth	Tracks 100 high-quality, cash-generative U.S. companies with consecutive dividend growth histories, balancing dynamic yield with defensive stability.	Choose this if your goal is building a reliable, compoundable passive income stream to live off of later.
Microsoft (MSFT)	Mega-Cap Technology	Combines an incredibly durable enterprise software monopoly with massive cloud infrastructure growth and deeply entrenched AI monetization.	Choose this if you have a long runway and want exposure to structural technology tailwinds via a highly profitable business.
Vanguard Total Stock Market ETF (VTI)	Pure Market Neutrality	Completely removes individual company risk by owning more than 3,500 U.S. stocks across large, mid, and small caps.	Choose this if you want zero exposure to single-management mistakes and want a set-and-forget foundational asset.

My apologies to anyone who lives in Cleveland. Not for the nickname or the reputation that comes with Cleveland….but actually sorry that you live there!

I have to return to Cleveland yet again for a work trip. I’ve never seen a more secluded city in my life with maybe the exception of downtown Buffalo in the dead of winter. Don’t get me wrong, they have some decent restaurants downtown and the Rock and Roll Hall of Fame. Beyond that? The Browns? At least the Guardians are in the MLB playoffs.

I understand based on proximity and that less people having to fly is the reason for this destination. But for the cost of my round-trip ticket (almost $1000), I’m guessing we could have picked Chicago which has more direct flights and saved everyone some money and been in a great city.

Bottom line is this for companies: if you are going to have live meetings and force people away from their families, please hold the meeting is a somewhat enjoyable (and preferably warm) location. This would not qualify Cleveland as a location. But apparently, as they say in Cleveland: “At least we’re not Detroit!”

As we are about to enter the 4th quarter of the year, it’s time to really start focusing on what your taxable income is going to look like for 2026. It’s also very important to find ways to minimize your taxable income. One way is to hire an accountant who apparently is either incompetent or tries illegal ways to save you money (I’m half joking because the guy I used for years almost went to prison and years later I’m still receiving audited tax returns from the IRS owing money….so be careful!)

However, I’m talking about ways you can actually help yourself with tax harvesting both losses and gains. Here is some good information that is worth a read:

When it comes to capital gains, the conventional approach is to delay realizing them for as long as possible so you don’t have to pay the associated taxes. However, waiting isn’t always the best strategy. Sometimes harvesting a gain today can set you up for lower taxes tomorrow. 

You can think of such tax-gain harvesting as the less-well-known sibling of tax-loss harvesting. (As a refresher, that’s when you sell a depressed asset and use the resulting loss to lower your taxes.) In fact, using them together can help you maximize the benefits of both, as we’ll see below. 

Finally, it’s worth noting that you can harvest gains at any point, but the final few months of the year are a particularly good time to do so as you should already have a sense of your total income and potential tax liability for the year, as well as a target list of tax-loss harvesting opportunities. 

Now let’s dig in. 

How does tax-gain harvesting work?

You can sell investments with a taxable gain for a variety of reasons—to raise cash, rebalance a portfolio, reduce a concentrated position, etc.—but with tax-gain harvesting, you’re doing so specifically for tax purposes. 

The concept is pretty straightforward: You just sell the investment when you think it’ll have the least impact on your taxes. If you’d like to keep the investment, you can even turn around and buy it again. Doing so effectively resets the cost basis on which your future tax liability will be calculated. This opportunity isn’t available when you’re harvesting losses, because of the wash-sale rule. (Just be sure every share you sell is for a gain. If any of them are losses, repurchasing the same asset could trigger a wash sale.)

Before getting into some examples, here are a few things to keep in mind:

• Tax-gain harvesting works only in a taxable account, like a brokerage account. You can’t do it in a tax-deferred IRA or 401(k), as you wouldn’t realize taxable gains in such accounts.
• If your taxable capital gains exceed your losses, you could impact tax calculations that look at your modified adjusted gross income (MAGI). This includes whether your Social Security benefits are taxed.

Now, here are three situations in which tax-gain harvesting could make the most sense:

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Ready to invest tax-efficiently?

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1. You expect to have a “lean” year

For 2025, individuals with taxable income below $48,350 ($96,700 for married couples) pay 0% tax for long-term capital gains (LTCG). 

In years when you’re under the threshold—say, if you’re in between jobs, or receive a smaller bonus—you could effectively lock in tax-free long-term gains. The idea would be to realize just enough LTCG to stay within the 0% tax bracket. 

For example, a single investor with taxable income of $44,250 for the 2025 tax year (after accounting for the $15,750 standard deduction) could realize up to $4,100 of LTCG without going over the $48,350 threshold for the 0% LTCG tax bracket. If they bought the investment back, they’d reset their cost basis and potentially lower their tax burden in the future. 

(Note that this applies only to long-term capital gains; short-term gains on assets held one year or less are taxed as ordinary income.)

2. You plan to also realize some losses

If you realize a loss on an investment, you can use it to offset your taxable capital gains and potentially lower your ordinary income by up to $3,000. 

So, if you plan to lock in some losses this year, you could also realize an equal amount of taxable gains. The losses effectively zero out the gains, likely eliminating the capital gains taxes that might otherwise be due.

Again, if you don’t need the proceeds from the sale, you could consider repurchasing the same stock to reset the investment’s cost basis. That way, you would pay no tax on the current gain—and any realized capital gain in the future would be based on the new, higher cost basis. 

3. You need to do some portfolio maintenance

Sometimes your winning positions can throw off your portfolio’s target asset allocation, as one set of stocks rises faster than the rest. For example, say your tech stocks are doing better than your energy stocks. That could leave you overexposed to volatility in the tech sector and potentially laden with more market risk than you’d intended. 

Selling some of your gainers—ideally along with some losers to help soften the tax hit or by targeting a specific tax bracket—can help bring your portfolio back to its target allocation, while potentially limiting the tax impact of the sale. Then you could use the proceeds to buy some of the laggards.

The bottom line

By strategically harvesting gains in certain tax years, you can potentially reduce your tax liability and keep your portfolio in balance. Be sure to consult your financial advisor and tax professional to implement a strategy that works for your situation.