Here Are My 4 Most Profitable Investments Ever, and Which One I'd Buy More of Right Now

I'm a buy-and-hold investor, and the majority of the stocks I've owned for more than a couple of years are worth significantly more than I paid for them. However, there are some standouts that have been the biggest drivers of long-term returns in my portfolio.

With that in mind, here are the four most profitable investments I've ever made, ranked by dollar amount, not percentage gain. While I'm not planning to sell a single share of any of them, there's one in particular that I'm considering adding money to right now.

Where to invest $1,000 right now? Our analyst team just revealed what they believe are the 10 best stocks to buy right now. Learn More »

1. Berkshire Hathaway

Berkshire Hathaway (NYSE: BRK.A)(NYSE: BRK.B) was one of the first stocks I ever bought, and I've added to my position quite a bit over the years. And now, Berkshire is my most profitable investment. It hasn't been the best percentage gainer in my portfolio, but it has been one of my largest investments, so its steady and solid return has resulted in a strong return.

I've written before that if I could only own one stock, it would be Berkshire. With over 60 subsidiary businesses and a massive stock portfolio with more than 40 additional investments, it's like a diversified investment portfolio in one stock. Plus, with a staggering $325 billion in cash, it has incredible financial flexibility to pursue any opportunities that arise.

2. MercadoLibre

If you were to ask me to name my highest-conviction international stock, it would be Latin American financial technology company MercadoLibre (NASDAQ: MELI). While I was admittedly late to the party with MercadoLibre, I bought at good times -- first in the early stages of the COVID-19 pandemic and again in the 2022 bear market.

MercadoLibre isn't without risk. Some of its core markets, like Argentina, aren't exactly the most stable, and as its new but impressive credit business grows, that adds an element of loan loss risk. But with the number of items sold on its marketplace growing 28% year over year in the most recent quarter and payment volume on the Mercado Pago platform exceeding $200 billion annually, this is a commerce powerhouse that is doing a great job of executing on its vision.

3. Kinsale Capital Group

Kinsale Capital Group (NYSE: KNSL) is an impressive insurance business, specializing in notoriously difficult types of insurance and doing it more profitably than the competition. I bought Kinsale shares a few years ago, and through solid performance, it has been a big winner in my portfolio. Unlike the first two stocks on this list, I didn't buy Kinsale with the idea that it would become one of my largest investments. The company's stellar performance has made it happen.

Although Kinsale has grown impressively in its roughly 15-year history, it still only has about 1% share of the specialty insurance market. If it can keep its impressive momentum going, the future could be very bright.

4. Bank of America

I bought shares of Bank of America (NYSE: BAC) a few years after the financial crisis ended, and the bank's progress in the roughly 12 years since I've owned it has been remarkable. CEO Brian Moynihan and his team have dramatically improved asset quality and have turned the bank into a leader in the digital age.

Which is the best buy right now?

To be sure, I could make a solid case to buy any of these. I've never sold a single share of any of them and have no plans to do so. But with that in mind, the stock on this list I'm planning to add to in February is Bank of America.

Not only do I believe the general direction of interest rates will be lower for the next few years, but bank stocks, especially the large ones, could be big beneficiaries of the new administration's deregulation efforts and potential corporate tax cuts. I also expect a surge in merger-and-acquisition activity, as well as lots of interest rate volatility, which could help Bank of America's investment banking and trading revenue.

Bank of America currently trades just below its 52-week high, but it's there for a reason. It handily beat expectations for the latest quarter on both the top and bottom lines, and it could be a great environment for bank profits for at least the next several years.

Don’t miss this second chance at a potentially lucrative opportunity

Ever feel like you missed the boat in buying the most successful stocks? Then you’ll want to hear this.

On rare occasions, our expert team of analysts issues a “Double Down” stock recommendation for companies that they think are about to pop. If you’re worried you’ve already missed your chance to invest, now is the best time to buy before it’s too late. And the numbers speak for themselves:

• Nvidia: if you invested $1,000 when we doubled down in 2009, you’d have $336,677!*
• Apple: if you invested $1,000 when we doubled down in 2008, you’d have $43,109!*
• Netflix: if you invested $1,000 when we doubled down in 2004, you’d have $546,804!*

Right now, we’re issuing “Double Down” alerts for three incredible companies, and there may not be another chance like this anytime soon.

Learn more »

*Stock Advisor returns as of February 3, 2025

Bank of America is an advertising partner of Motley Fool Money. Matt Frankel has positions in Bank of America, Berkshire Hathaway, Kinsale Capital Group, and MercadoLibre. The Motley Fool has positions in and recommends Bank of America, Berkshire Hathaway, Kinsale Capital Group, and MercadoLibre. The Motley Fool has a disclosure policy.