In the span of about a year, hedge-fund manager Ted Weschler twice dined with Warren Buffett at Piccolo’s, one of the billionaire investor’s favorite Omaha, Neb., haunts.

Along the way, Mr. Weschler would step out of a crowd of Buffett disciples to become one of a few candidates to replace the Oracle of Omaha as chief investment officer at Berkshire Hathaway Inc. By the end of his second meal at Piccolo’s, Mr. Weschler would have a job offer in hand.

This post is based on interviews with people familiar with Mr. Weschler, Mr. Buffett, and Berkshire. Weschler will start work at Berkshire Hathaway this month, and the challenges of the job were detailed in a Wall Street Journal story today.

Even though Mr. Weschler considered Mr. Buffett a hero, he wasn’t about to trade in his below-the-radar life in Charlottesville, Va., for the challenge of trying to succeed Mr. Buffett. Over the past decade, his fund, Peninsula Capital, had turned in a strong double-digit-percentage annualized return, while the broad Standard & Poor’s 500-stock index was basically flat.

Considering how much money he had made for himself and investors — people familiar with Peninsula estimate that about 40% of its $2 billion in assets is Mr. Weschler’s money — he had enjoyed a fairly anonymous life.

That would begin to change in June 2010, when Mr. Weschler paid a visit to Glide, a homeless charity in San Francisco that Mr. Buffett supports. That very week, Glide was holding its annual fundraiser: an auction, with the top bidder winning a lunch date with Mr. Buffett.

Intrigued by the chance to meet his hero and impressed by Glide, Mr. Weschler put in a bid of $2.6 million. He won the auction, but wishing to remain out of the spotlight, he asked that his identity not be disclosed publicly.

A couple days later, Mr. Buffett called Mr. Weschler himself to set up the meal, offering to come to Charlottesville for lunch or dinner. Mr. Buffett said he was free for the next few nights. Instead, Mr. Weschler said he would come out to Omaha and they could dine at Piccolo’s, a known Buffett favorite.

The two met at Mr. Buffett’s office, but ended up spending more than an hour talking at Berkshire before heading out. They clicked immediately.

During dinner, Mr. Weschler noted their 30-year age difference and age, and asked Mr. Buffett for advice for his next three decades. Mr. Buffett responded with a variety of insights. Among them, he told Mr. Weschler that friends would be critically important to him.

The two, in a way, became friends.

After the meeting, Mr. Weschler kept in touch, sending his idol his end-of-the-year investor letter. Mr. Buffett sent him a note back, “nice job.”

In May 2011, at the behest of one of his friends, Mr. Weschler once again attended Berkshire’s annual shareholder meeting in Omaha. About a month later, Mr. Weschler donated another $2.6 million, winning a second Glide auction and a follow-up date with Mr. Buffett. This time, he came to dinner at Piccolo’s armed with a yellow ledger pad and a number of questions. He took notes on Mr. Buffett’s answers.

At one point during the dinner, Mr. Weschler paused and suggested that Mr. Buffett too, could ask some questions. “I’m an open book,” he said.

Mr. Buffett took the opportunity to make his simple pitch. He asked Mr. Weschler if he would be interested in coming to work for Berkshire.

The question caught Mr. Weschler off guard. Not wanting to be dismissive of his hero, he said he would give it some thought. When Mr. Buffett drove Mr. Weschler to his hotel room that night, the Berkshire chairman ended the evening by saying that Mr. Weschler could think about the decision for a year or two, if he needed the time.a