Day: November 23, 2025

• Tom Russo says resilience is vital, debt is dangerous, and investing is both a young and old person’s game.
• The veteran fund manager warned against excessive gambling and ruled out retiring anytime soon.
• Young investors might have more energy, but older ones can be more patient and disciplined, Russo said.

Veteran investor Tom Russo says children need to build resilience, debt can be devastating, and older people have some advantages when it comes to beating the market.

Russo is the managing member of Gardner Russo & Quinn, an investment firm with a $9.3 billion US stock portfolio as of September 30, per its latest 13F filing.

The father of two told Business Insider that teaching resilience to kids starts with letting them fall on the playground, so they can learn to get back up and keep going.

They have to experience pain and discomfort as “those moments happen all the time in life,” he said. “The greatest lessons are learned when trying to work yourself out of something that doesn’t go well. And the worst thing to do is to avoid those from happening when they naturally would.”

Asked how young people can get ahead at a time when AI threatens to take jobs and many feel priced out of the lives they want, Russo cited Warren Buffett’s warnings about credit-card debt as a “chain across your back” that gets tighter and tighter until it chokes you. Russo added that “buy now, pay later” options pose a fresh threat, as they tempt people into spending money they don’t have.

Russo also cautioned against gambling too much, saying it’s a “loser’s game to begin with” and “probably isn’t going to develop your thinking and wisdom and reason.”

The market veteran, who turned 70 this year, ruled out retiring anytime soon. While young investors might have more time and energy to travel and dig deeper into prospective investments, older ones “develop judgment, and you’re a little less impetuous, and a little more patient, and probably a little bit more asleep,” he quipped.

Russo is far from the first investor to continue working past retirement age. Buffett, 95, will step down as Berkshire Hathaway’s CEO before the new year, but intends to continue writing Thanksgiving letters to his shareholders and remain involved in the company as its chairman.

• Slack cofounder Stewart Butterfield said that employees should have a “perpetual desire to improve.”
• He shared a story from 2014 on “Lenny’s Podcast,” where he called an early version of Slack “terrible” in an interview.
• Employees printed out the interview quote and pasted it on the office walls the next day — but Butterfield stands by it.

For Slack cofounder Stewart Butterfield, embarrassment can be a useful and motivating tool.

Butterfield led Slack, which is now owned by Salesforce, from 2009 to 2023 as CEO. In 2014, he gave an interview where he called the early product “terrible.” Employees responded by putting posters up around the office, he said on “Lenny’s Podcast” — but he stands by it.

“I try to instill this into the rest of the team, but certainly I feel that what we have right now is just a giant piece of shit,” he told the MIT Technology Review in 2014. “Like, it’s just terrible, and we should be humiliated that we offer this to the public. Not everyone finds that motivational, though.”

On the podcast, Butterfield described the aftermath.

“I came into the office the next day and people had printed out on 40 pieces of 8.5-by-11 paper that quote and pasted it up on the wall,” he said.

Butterfield defended what he had said in the 2014 interview: “To me, that was like: you should be embarrassed by it. It should be a perpetual desire to improve. You should never be like, ‘Oh, this is great.'”

He could be proud of “individual pieces,” Butterfield said, but in the aggregate, leaders should only see the “almost limitless opportunities to improve.”

Butterfield gave two examples of the endless search for improvements.

First, he pointed to Toyota’s principle of “kaizen,” or continuous improvement. The philosophy ensures “maximum quality, the elimination of waste, and improvements in efficiency,” per Toyota’s UK magazine.

Second, he pointed to Bridgewater founder and billionaire investor Ray Dalio. Michael Jordan’s ski instructor once told Dalio that he “reveled in his mistakes” and saw them as “little puzzles that, when you solve them, give you a gem.”

How to be critical — and when — is an art that all leaders approach differently. Netflix’s CTO said that the company uses “continuous, timely, candid feedback.”

Meta CFO Susan Li said that Mark Zuckerberg has refined his ability to give feedback over the years. Now, he’s “world-class,” Li said.

On the podcast, Butterfield said that “trying to be critical” and “trying to find improvements” can be helpful tools.

“Not always, not with every person,” he said. “But most of the time, with most people, you can get them to the point where that really direct criticism is actually motivational.”

Butterfield would go on to lead Slack to become one of the most popular workplace messaging platforms in the world, eventually selling it to Salesforce for $27.7 billion.