Roelof Botha used to write 109 on the corner of his notepad every week when he started at Sequoia 19 years ago. It was a shorthand to keep himself focused on picking exceptional startups to deliver his private goal of $1 billion in total gains.

The rise of players like Tiger Global in the industry has shown there’s an appetite from founders who are looking for hands-off investors. Less coach, more cash.

“He is incredibly competitive and loves to win, so it's not like there's not a full-on carnivore in there,” said Eventbrite CEO Julia Hartz. “It’s just on top of that, he has the ability to channel his energy and not let his ego become something that distracts him, or more frankly, gets into that destructive zone.”

His big break came with YouTube, one of the first deals he led. He met the founders through his PayPal connections when it was just a team of three people. It was one of the first unicorns, before anyone even used that term, said Gideon Yu, its former CFO.

Botha wasn’t interested in selling YouTube quickly with a high price to get a win on the board, Yu recalled. Instead, he insisted on a deal that would set up the company for long-term success.

“With some folks, emotions and bright, shiny objects will tend to distract you in situations like this. With Roelof, there’s always a very strong foundation and a very true north,” Yu said. After working with other investors, Yu came to realize that Botha’s approach put him in the “top echelon” of VCs.

Sequoia founder Don Valentine had warned Botha in the interview process that he hadn’t failed enough in his career. Successful people join venture capital, only to have to face the fact that good investing means taking risks in startups that are more likely than not to fail.

In 2009, Botha discovered Unity and Eventbrite. The next year, he invested in MongoDB and then finally got a chance to invest in Square in 2011. They would all become publicly traded companies, part of his nine career IPOs.

“That's part of the beauty of this business. Even though you could make big mistakes, there's another at bat tomorrow, because people are starting interesting new companies,” Botha said. “So if you're willing to swallow your disappointment, buckle up, get back on the bicycle, get back on the horse, get back on your skis — whichever thing it is that you can identify with – you just try again.”

Unlike a lot of VCs who will end up specializing in a subsector, Botha is a true polymath who invests across consumer, enterprise and health care, said Sequoia’s Lee.

“He always did what was right for the company. He was acting in good faith, and he went above and beyond to make sure that I was treated fairly and with respect through it,” Libin said.

While plenty of VCs would find a way to humblebrag about the role they had in helping a company in its earliest days, Botha’s style has always been understated. 23andMe’s Wojcicki considers him “Obama-like” for his intellect and integrity.

it disappointed him that the fund had to distribute shares so early to LPs when, if they’d had a chance to hold on, they could’ve seen even higher returns.

“What a lot of people underestimate is how much company-building still happens at every stage,” he said. “Even when a company's public and you think it's mature, there's so much more innovation that can happen.”

along the way, he learned a crucial lesson: Cash can dry up, but counsel is evergreen.