My dad lost his very best friend in the world at the young age of 45. He lived on the next 42 years without him.

Maybe he was thinking of Dave when he grew wistful at one of our monthly lunches some time ago. He said, “A man can have hundreds of acquaintances, but it’s the lucky man who has one … maybe two … really genuine, good, and close friends.” The ones you would trust with your life.

I’ve found his words to be true and his math to be accurate …

Acquaintances will come to your funeral if convenient; a friend would be with you when you’re on your deathbed.

Less morbidly put: Brian Chesky, co-founder and CEO of Airbnb, told Victoria Salva for her article in Inc., “If you have someone in your life where if you were to call them or text them, you have to get them up to speed, then you’re not connected.”

Right. Probably a better way to illustrate the difference between a friend and an acquaintance.

Chesky was reflecting on his climb to the top.

“No one told me when I started this journey—how lonely it would be,” he said. “It doesn’t have to be, but it’s almost like by default.”

Default? Maybe. And by that he means maybe it couldn’t be helped. But if we prioritize our mental and emotional well-being, and what makes us the best leaders possible, then friendships have to be included in the equation.

Loneliness certainly doesn’t have to be. This, Chesky learned from an interesting source.

He told Salva that in mid-2021, months after Airbnb’s initial public offering (IPO), he told former President Barack Obama about his feelings of loneliness.

“I remember telling him,” Chesky said, ‘I think I need to be in another relationship.’” Obama’s reply surprised him.

“I don’t think you need to be in a relationship. I think what you need are friends,” Obama told him.

Chesky’s mind exploded.

According to Salva’s article, Obama told Chesky he had 15 people he stayed “connected to” since before his time in the Oval Office.

Although it’s impossible to know how many of those 15 people were Obama’s real friends, as I’m defining it here—the point is made. (If all of them were true friends, then good for him.)

But the fact remains that the once-leader of the free world has friendships he has valued and nurtured over the years, no matter how busy and insane life got. People he absolutely trusts. People who he can be real with and laugh with. People who share his pain. People with mutual memories and that he can talk to about life. People who would drop everything.

Obama’s story proves that, indeed, loneliness doesn’t happen by default nor is it inevitable. Friendship simply takes prioritization.

And the good it does is miraculous.

Salva points out that while Chesky said he is a “huge proponent in pouring your life into something,” such as a company, his story reminds leaders to reconsider spending countless hours being productive at the expense of nurturing healthy relationships.

Ultimately, Chesky said, doing so makes for better leaders.

“Lonely leaders are probably not the best leaders. When you’re lonely, you’re probably less empathetic, your sense of vigilance is up, you don’t necessarily see problems really clearly,” he said.

True dat.