Regrets

A story about Reid Hoffman, regrets, and perspective. Also, 7 other things worth your time.

I wrote most of this yesterday. Then I woke up early this morning, and I found myself thinking about #2 from the “7 other things,” that you’ll find at the bottom of this newsletter. I just thought I’d flag that; maybe others will find it poignant too.


Almost 17 years ago, a 20-year-old college student who had been working on a new startup for a few months got a meeting with Reid Hoffman, who had co-founded PayPal and was a year or two into his latest venture, LinkedIn.

Hoffman was also an active angel investor, and he found the young man’s idea interesting. But, his pitch was unfocused:

“I’m not sure I’m going to keep doing this. After the summer, I may go back to school. … If you don’t like this idea, I have another idea …”

Hoffman took pride in what he later described as his ability to find “good ideas in bad pitches,” and so he put up $37,500 for the young man’s idea — pocket change, given his takeaway from PayPal — as part of the first round of financing.

That 20-year-old college student … was me.

No, I’m kidding. It was Mark Zuckerberg, and the company was Facebook, and Hoffman’s initial investment ultimately became worth something like $500 million.

Hoffman has told this story a few times, but I found it in a 2018 article in The Wall Street Journal, in which he shared perspectives on his lucky breaks and his missed bets.

His best career move?

Saying yes when Peter Thiel invited him to join the board of the company that ultimately launched PayPal. He said he hesitated because he thought the original idea was “terrible,” but joined because he thought Thiel and his team were brilliant.

“The entire trajectory of my life, and my impact in the world and my impact in the Valley would be different without having made that bet," Hoffman said.

His biggest professional regret?

Actually, this is why I’m writing. Hoffman said it was that he passed on the digital payments company Stripe, founded by Patrick and John Collison:

Mr. Hoffman met the brothers, liked them, and acknowledged that they had a "really good" idea. But he passed, because he thought they were valuing Stripe too high, and because he knew just how hard it is to make a go of it as a payments company.

Last month, Stripe closed its most recent round of financing: $600 million at a valuation of $95 billion.

It’s missed opportunities, not losses, that Mr. Hoffman regrets. Not investing in a company that goes into orbit costs him a lot more than an investment going to zero, he says.

“Losing those is the thing that is the disaster,” he says. “It’s the, ‘Oh, my God! This thing is going to the moon and I’m not in it!’ ”

I don’t want to put too much emphasis on this, since the reporter asked Hoffman for his biggest hits and misses, and he answered the questions. I don’t think he’s walking around in a funk, years later, kicking himself each morning for not investing.

But, it stuck with me for a while after reading it, I suppose for the following reasons:

  1. First, because it reinforced for about the 1,000th time that quote about how people usually regret the things they don’t do, more than the things they do. (I mean, with obvious exceptions; our prisons are probably full of them).

  2. Second, because I found it interesting, and maybe even reassuring, that a guy who has made billions investing in early-stage startups was able, quickly, to answer a question about regret, and “the one that got away.”

  3. Finally, because it occurred to to me that if you shave off a few zeroes (OK, more than a few), other people who overheard me articulate something I regret might have a similar reaction to how I reacted to Hoffman.

Now, I’ve been trying to think of a “big regret” to illustrate this. I suppose one might be that around five years before Facebook, I spent a ton of time working with a classmate and business partner—someone who reads this newsletter, actually—on an idea to launch a social network for college students.

Nah, I thought, there’s probably more future in sticking it out as a tax lawyer for another year or two, and then packing all my stuff in a used Kia Sportage to drive to Hollywood and try my hand at screenwriting.

Or maybe I’d point to some other career false starts or missteps—the fact that I can’t quickly come up with a truly pithy one might say something. But anyway, let’s plug it in:

Really? You’re saying you regret not making some career move that might have made you a bit wealthier … and you’re doing this while working on another opportunity that you’re dedicated to and passionate about, from the comfort of the home you happily share with your wife and daughter?

I guess the moral of the story is that it’s OK to use regrets if they motivate you to take action and make better choices in the future. But at the same time, take comfort in them. The things you regret might provide evidence that you’re actually doing pretty darn well.

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I have learned in the last 24 hours, thanks to many people who emailed and commented, that “bubbler” is used as a term for “water fountain” in parts of New England besides my native Rhode Island, as well as Wisconsin. Thanks!


7 other things worth your time

  • President Biden called for all American troops to be home from Afghanistan by September 11. "We delivered justice to Bin Laden a decade ago, and we've stayed in Afghanistan a decade since then," Biden said. “Since then, our reasons for remaining in Afghanistan are becoming increasingly unclear." (USA Today)

  • It’s one thing to say we’ve been in Afghanistan a long time. But I feel like it’s another to say that Thomas Gibbons-Neff, the current Kabul correspondent for the New York Times was 13 on 9/11, and has had time since then to grow up, graduate from high school, enlist in the Marines for four years, serve two tours as an infantryman, come back home, go to college, graduate, start a career at The Washington Post, get recruited by the Times, and spend a few years on another beat before getting the Afghanistan assignment. His latest: Afghans Wonder ‘What About Us?’ as U.S. Troops Prepare to Withdraw. (NYTCO, NYT)

  • Coinbase, the big U.S. crypto platform that lets you buy and sell cryptocurrencies like bitcoin, ethereum, went public Wednesday in a direct listing, soaring and then falling back to earth, but still ending the day with a value of roughly $85 billion, bigger than either NASDAQ or the company that owns the New York Stock Exchange. Perhaps even more interesting is how individual cryptocurriences jumped. Even Dogecoin, created as a joke eight years ago and not even available on Coinbase, rose. (WSJ, $)

  • Kim Potter, the former police officer in Minnesota who fatally shot Daunte Wright was arrested Wednesday and charged with second-degree manslaughter. She’s out on $100,000 bond. Separately, 1,000 miles or so to the east, ex-Buffalo police officer Cariol Horne, who tried to stop her partner from choking a suspect in 2006, and was fired just short of retirement as a result, will receive her pension, retroactively, after winning a lawsuit against the city. (CNBC, WIVB)

  • Authorities in California are crediting a true-crime podcast for helping them solve the 1996 disappearance of a college student named Kristin Smart. Paul Flores, Smart’s former classmate, was charged with murder; his father, Ruben is facing a charge of being an accessory. (People)

  • The head of the division of Disney in charge of amusement parks says it’s changing its strict dress code and other rules to reflect a new focus on inclusion. Specific changes include: “greater flexibility with respect to forms of personal expression surrounding gender-inclusive hairstyles, jewelry, nail styles, and costume choices; and allowing appropriate visible tattoos.” Consider that up to 2012, beards were banned for park employees. (Deadline)

  • Bernie Madoff died in prison, at age 82. (CNBC)


Thanks for reading. Photo credit: a YouTube still from the movie We’re the Millers. I’ve written about the regrets thing in a different context at Inc.com. If you’re not a subscriber to Understandably, please sign up for the daily email newsletter—with thousands and thousands of 5-star ratings from happy readers. (Want to see all my mistakes? Click here.)

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