When Berkshire Hathaway (BRK.B) CEO Warren Buffett steps down at the end of 2025, it'll mark the conclusion of one of the most remarkable runs in investment history. The Oracle of Omaha has beaten the S&P 500 more times than most people can count, and his departure has the financial world wondering what comes next.

Jay Woods, Chief Market Strategist at Freedom Capital Markets, shared his perspective on Buffett's legacy and some personal encounters with the investing icon that offer a glimpse into why his approach became so legendary.

Quality Over Everything

When asked what stands out most about Buffett's career, Woods didn't hesitate.

"Buffett to me, the ultimate investor," Woods said.

The strategy sounds simple when you break it down: find quality companies, buy them cheap, and hold them for the long haul. Buffett famously steered clear of the technology sector for most of his career, with Apple Inc. (AAPL) being the notable exception. But here's the thing—"he didn't need to."

"Warren Buffett was someone who bought quality. He bought lots of it. He bought it on the cheap," Woods explained.

What really set Buffett apart, according to Woods, was his refusal to get tangled up in the "day-to-day operations" of his investments. Instead of micromanaging, he took a long-term view on companies he believed would perform well over time. That patience and discipline became his signature.

"His overall trading philosophy is the stuff of legends, and the people that have invested with him have been rewarded for it," Woods said.

With Buffett stepping away, Woods sees it as "the end of an era." And he's not optimistic about seeing another investor match that track record. "I don't think we'll ever see anything like that again."

A Front-Row Seat to History

Woods shared a story that few have heard before, dating back to his days working at Goldman Sachs (GS). It was 2008, right in the thick of the financial crisis when major banks were collapsing left and right.

"I had to go back to the office to get something and it's very rare I go back to the office. I go back to the office and I go into the lobby and who's in the lobby? A ton of security people. And in the center of that scrum is Lloyd Blankfein and Warren Buffett," Woods recalled.

At the time, Woods had no idea what he was witnessing. The next day, it became clear: Buffett was taking a stake in Goldman Sachs, throwing the firm a lifeline when it looked like it might go the way of Lehman Brothers.

"It was announced next day that Warren Buffett was taking a stake in Goldman Sachs and helping secure us when it looked like Goldman was on the ropes like so many other financial companies," Woods said.

Looking back, Woods realized the significance of that random encounter. "That was part of a historic meeting that I had no idea I was walking by."

He also caught a glimpse of Buffett from a distance on the floor of the New York Stock Exchange, another brief intersection with one of investing's biggest names.

What Happens After Buffett?

The big question now is what Berkshire looks like without Buffett at the helm. Woods admitted it'll feel strange not getting those famous annual letters or seeing Buffett as the face of the company.

"Berkshire continues to invest in great quality companies and I look forward to see what their philosophy is going forward. I suspect it won't change too drastically from what Warren Buffett has instilled in them," Woods said.

That said, there are signs that Berkshire might be shifting gears slightly. Recent moves suggest a more aggressive stance, including buying UnitedHealth Group (UNH) on a dip and making plays in technology names like Alphabet Inc. (GOOGL).

"I'm curious to see what kind of investing strategy the new team takes because we are seeing some more risk and more technology names," Woods noted.

Then there's Occidental Petroleum (OXY), which Berkshire has been accumulating despite the stock going nowhere fast. Woods wonders if the company remains bullish on energy or if the time horizon is changing.

"Are they still believers in the energy space? And what's their time horizon?" Woods asked.

The answers to those questions will define what Berkshire becomes in its post-Buffett era. Whether the company sticks to the value investing playbook or embraces a more dynamic approach, one thing is certain: the transition marks the end of an investing legend's active reign and the beginning of something new for one of the world's most watched investment firms.