Good morning, friends!

In December 2013, Foursquare founder and CEO Dennis Crowley was absorbed in reading Nick Bilton's new book Hatching Twitter. Over the weekend, he had just gotten to the section when the board decides to suddenly replace Ev Williams as the CEO of Twitter.

And then Crowley saw a meeting pop up on his calendar: "Meeting with Foursquare board members Ben Horowitz and Albert Wenger on Friday, Dec. 13."

Crowley immediately emailed his assistant to ask what the meeting was about, but she didn’t know. That’s when the panic set in. He was almost certain he was getting fired.

When Crowley entered the boardroom, Horowitz and Wenger started making small talk and asking him about his holiday plans.

“Gentlemen, if you have something to say to me, just say it. Just break the news,” Crowley told them. They looked confused and asked what “news” he was talking about. “You guys aren’t here to fire me right now?” he said. To which they responded, “What’s wrong with you? We just wanted to check in before the holidays.”

It led to a serious conversation about Crowley's self-doubts, the challenges of his role, and the difficulties of transitioning from a consumer-focused company. And finally, he said what had been on his mind for a long time: He wasn't sure if he was the right person to lead Foursquare.

"Sometimes, it's hard to have those hard conversations," Crowley says. "So you need a moment like this one that forces the hard conversation to happen.”

That moment of anxiety changed the entire course of Foursquare's trajectory and Crowley's career. Over the next two years, he would find his own successor, step down as CEO, and move to an executive chairman role.

In this conversation, Crowley gives an honest account of what happened when he realized that he was no longer the right person to lead the company he founded.

Below is an excerpt of the interview, but I encourage you to watch the full interview here:

(Photo Credit: Sebastian Alvarado / Coffee & Football)

In the time between the meeting and when you stepped down as CEO, you never once changed your mind and said, “No, no just kidding, I can be the operator after all"?

CROWLEY: I didn't have the "just kidding" moment, but I did have a lot of sleepless nights where I thought, ‘Am I doing the right thing? Is this the right thing for the company? Is it the right thing for me?’ It was a really stressful time in my life.

My brother worked at Foursquare at the time, and he was one of the first people I told. He was angry at me because he didn't think it was the right move while I was like, "I think it is." That was a hard conversation to have with him because this was someone who knew me better than anyone else. It was a really stressful time in my life.

Looking back, I don't have regrets. It enabled the company to do things it wouldn't have been able to do otherwise, and it enabled me to do things I wouldn't have otherwise done.

How do you know if something is just a temporary moment of doubt or if it's truly an existential unhappiness?

It's the amount of time you spend noodling on the same problem without being able to come up with a solution.

Saying I was losing sleep over this means I was literally not being able to sleep and waking up in the middle of the night super stressed over it: "Is this the right decision or not?" One of the harder things I had to do in my career at Foursquare is let go of the role.

In hindsight, I can say it was the right decision, but I can tell you I was feeling physically sick in the conference room rehearsing my notes. Twenty minutes before I had to get on stage and communicate it to the staff, I had doubts.

But it was the day after when I walked to work, not as CEO but as executive chairman, that I had this moment of levity and release where I was like, "I did it. I don't carry this weight on my shoulders." I remember exactly where I was — I was on the corner of Bleecker Street and Bowery — where I had the emotional release of laughing and tearing up at the same time.

It was 24 hours after I communicated it to the company that I realized it was the right thing to do. Sometimes you don't know the next day, and sometimes you don't know until 4 years later. It's hard. There are no easy answers.

Read on the Website Here

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PROFILES.

— The teenage day-trader who lit the markets on fire [**HIGHLY RECOMMEND**]
— The investor who drove the GameStop Reddit mania
— The founder of WallStreetBets
— The Goldman Sachs dealmaker
— The video game superstar
— The star who transforms adversity into power
— America's beloved comedian

PEOPLE TO KNOW.

The teenage day-trader who lit the markets on fire: Today's highly-recommended profile is by Michael Lewis from 2001, and it's a great reminder that history repeats itself. Long before WallStreetBets existed, there was teenage day-trader Jonathan Lebed. In 2000, he was prosecuted by the SEC for stock manipulation. He was making $800,000 trading on stocks he promoted on Yahoo Finance forums before school. If there's one thing you read today, let it be this. (The New York Times)

"If it wasn't for everybody manipulating the market, there wouldn't be a stock market at all."

The investor who drove the GameStop Reddit mania: The investor who helped direct the world’s attention to GameStop, leading a horde of online followers in a bizarre market rally that made and lost fortunes from one day to the next, says he’s just a normal guy. “I didn’t expect this,” said Keith Gill, 34, known as “DeepF—ingValue” by fans on Reddit’s WallStreetBets forum and “Roaring Kitty" on YouTube. He said he didn’t set out to draw the attention of Congress, the Federal Reserve, hedge funds, the media, trading platforms and hundreds of thousands of investors. Wild story. (WSJ; reply to this email if you can't access the article.)

“I’m not out for anybody. Roaring Kitty was an educational channel where I was showcasing my investment philosophy.”

The founder of WallStreetBets: The man who created Reddit’s WallStreetBets isn’t who you think he is. He is 39 years old. He lives in Mexico City with his wife and spends his weeks chasing after their 3-year-old twins and tending to his day job as a consultant—hardly the sort of character one might associate with the roiling investing forum. Although he hasn't moderated the community since April, it has been impossible for him to escape his legacy. (WSJ; reply to this email if you can't access the article.)

“A massive group of people have organized where they collectively have a seat at the poker table, which was previously invite-only. You can’t ignore them anymore.”

The Goldman Sachs dealmaker: When Stephanie Cohen began overseeing Goldman Sachs's consumer and wealth-management division, she and her team began to read Ben Thompson's website, Stratechery. She wanted to better understand the strategies the big tech firms like Amazon, Google, and Facebook were using to control the internet. Here's how she's planning to employ technology to supercharge Goldman's future. (BI; reply to this email if you can't access this article)

"She deeply understands that tech is going to be a key driver of competitive advantage for Goldman in the future."

The video game superstar: Tyler Blevins, better known as Ninja in the gaming world, is the closest thing gaming has to a crossover mainstream star. Blevins, 29, has amassed 16.5 million followers on Twitch, 14.4 million on Instagram, 6.5 million on Twitter, and 24 million subscribers on YouTube. Oh, and he makes $500,000 a month streaming. In this longform interview, he offers a tip for parents: "You want to know who your kid is? Listen to him when he’s playing video games when he thinks you’re not." (New York Times Magazine)

"Streaming makes you super self-conscious. You have to be the most sure person on the planet if you’re going to get into this and not be completely torn apart."

The star who transforms adversity into power: When she was in high school in the United States, Priyanka Chopra Jonas was incessantly bullied. Though she can rationalize it now, she admits that in high school, “it affected me adversely. It affected my confidence; it affected who I wanted to be. I felt exposed, when your skin is raw.” Here's how she turned racism and bullying into a raging fire that fuels her today. (Marie Claire)

“For that girl who was so scared, I’m proud of the person that I evolved into. I dealt with a lot, and I came out thriving."

America's beloved comedian: Two weeks before comedian John Mulaney checked into rehab for 60 days for an alcohol and cocaine addiction, he did this interview with GQ. In it, he discusses how 2020 affected his creative process, why isolation hasn't been good for him, and why he’s never felt more himself than when he’s voicing an animated pig. It's all over the place, but it's interesting. (GQ)

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AUDIO TO HEAR.

J.J. Watt's mentality of grit: Houston Texans defensive end J.J. Watt understands something that's played a crucial role in his life: You develop resilience by falling down and getting back up time and time again. One of the hardest moments in his career was when he went through two season-ending injuries. "I did not know how to deal with it," he says. "I did not handle it well." Here's how Watt learned to develop unshakeable mental fortitude. (Link available to premium members.)

Priyanka Chopra Jonas on how boredom sparked creativity: During quarantine, Priyanka Chopra Jonas struck a TV deal with Amazon, she shot and released two movies, and wrote a memoir all in 2020. "In this new world, I decided to find a sense of purpose," she says. "I really spun my creative mind." Here's how Chopra Jonas turned 2020 into one of the most productive years of her life. (Link available to premium members.)

VIDEOS TO SEE.

Mr. Beast on cracking the YouTube algorithm: Jimmy Donaldson, also known as Mr. Beast, is one of the best visual storytellers on the Internet. This video breaks down Donaldson's tactics and techniques and helps explain how he consistently rakes in billions of views on his videos. (Link available to premium members.)

Taylor Swift on the most creative period of her life: In this rare longform interview, Taylor Swift explains how her songwriting process has evolved in the last few years. During the pandemic, she released two surprise albums. "It was a breakthrough moment of excitement and happiness," she says. "I have referred to writing these songs as a kind of floatation device because obviously, [2020] has been hell on earth for everyone." (Link available to premium members.)

Stephen Hawking on his 'Theory of Everything:' This fascinating documentary gives us a glimpse of Stephen Hawking's quest for a "Theory of Everything.' This "holy grail" hypothesis could explain everything — from supernovae to black holes. Here's how Hawking unlocked the mysteries that ultimately dubbed him "master of the universe." (Link available to premium members.)

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