Learning to Hustle

It ain't where I been, but where I'm 'bout to go

In February of 2023, I shut down the startup I had poured my soul into. More than building a company, I had set out on a personal mission, one that meant the world to my family and me, with all the zeal of a missionary. When I made the decision to walk away, a friend recommended that I “spend six months playing Playstation and eating ice cream on the couch in your underwear.” 

Before I realized it, those six months had turned into seven. Seven months of playing video games, eating junk food, reading books, cooking, and cleaning. Everything except going outside and being in the world. I was like a zombie, only instead of craving brains I craved the numbing of online shopping and easy entertainment. New Amazon packages arrived daily, with everything from a new iPhone wallet to healing crystals said to promote enthusiasm and creativity, all purchased with a single click and delivered to my front porch. I read my entire anti-library of books, and when I was done I journaled on pages which got dark really quickly. I binged an entire season of Narcos and threw my shoes at the wall in disgust when there were no more seasons to watch. 

I was stuck, but I had numbed myself too much to care. 

It was in that context that I discovered Hustle, Adam Sandler’s 2022 ode to basketball. It’s not the kind of movie I would normally watch; I’m not a sports fan and barely a movie guy. But in my months of self-pity I had played every iPad game I could stand and I needed something better to distract me from the voices which kept telling me I was a failure, I should have tried harder, I should have hustled more. So when Netflix recommended Hustle, I served myself two scoops of mint chocolate chip and sat down to zone out. 

In the movie, Stanley Sugarman (played by Sandler) has been dreaming of becoming a coach ever since he joined the 76ers as a scout 30 years ago. After his chance is ripped out of his hands by the death of Sixers owner Rex Merrick, he flies around the world looking for a fresh talent to get back in the new owner’s graces. When he finds that superstar in Bo Cruz, the Sixers pass without even giving him a chance. Stanley refuses to quit, and leaves the Sixers to prepare Bo for the NBA. He calls on everything in his experience: a phone list of every great basketball player in the NBA, a relentless pursuit of perfection, and the wisdom earned from spending so many years around great players. He struggles with his own insecurity just as Bo struggles with his mental toughness. 

As I said, I’m not a sports fan. You won’t find me swinging a Terrible Towel on Sundays or wearing a Dodgers cap around town, and the personal dramas are uninteresting at best, and petty at worst. What little awe for the games I had growing up was ruined by the multiple steroids scandals and holdouts. 

But damn if I don’t love watching Bo Cruz (the Spanish diamond in the rough played by real life NBA star Juancho Hernangómez) dunk. Watching superstars like Dr. J and Allen Iverson, it felt like I was fourteen again watching Michael Jordan win his sixth ring. And when the too-smug-for-his-own-good rookie Kermit Wilts starts talking smack about Bo’s daughter just to get him off his game I could have punched him myself. 

While the basketball in Hustle is beautiful, the movie is about much more than sports. Yes it’s an ode to basketball, the real sport as opposed to the highlights you see on Sports Center. Sandler’s love for the scouts, trainers, coaches, and business people shines through as he plays a scout for the 76ers. But it’s also a story about fighting for your dreams, overcoming your past, and putting in the reps to become a true professional. And that’s where the movie really shines.

When the movie ended, my bowl was full of mint chocolate chip soup, the voices in my head finally gave me a reprieve, and I had a fire in my belly that I thought had been extinguished.

Just try watching Stanley’s motivational speech and not feeling something. I know I cant.

As opposed to the flashy Hollywood movies as of late, Hustle is understated. It was filmed on the streets of Philly, with incredible moves and even bigger stars, but there are no special effects or giant sets to distract from the story. The lessons in Hustle, like when Stanley tells Bo that obsession beats talent every time or when the pair are doing hill sprints at four am every morning in scenes reminiscent of Rocky, are the same lessons my grandfather and my drill sergeant taught me. And the off the court lessons shine just as brightly, as Stanley admits that he ruined his life in a drunk driving accident back in college. He’s been stuck since that accident, but in Bo we see Stanley’s project to fully redeem himself.

More than just the action or the lessons, Hustle is a reminder that the path to self-actualization is a series of bets we take on ourselves. 

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In startup culture, we love to talk about failure. We say catch phrases like failure is the only way to grow. I’ve known Venture Capitalists who won’t invest in a founder unless they’ve failed before. They believe it proves them scrappier, smarter, more likely to succeed. I’d said much of that myself, with meaningless phrases like failing forward. But I wasn’t prepared for the human side of failure. I wasn’t prepared for the shame I felt when others would ask how things were going and I had to tell them things weren’t. I didn’t appreciate the isolation I’d feel when my friends were working hard and I couldn’t get myself out of bed in the mornings. 

And the grief. The grief was the hardest, manifesting itself as rage towards the investors who didn’t invest and the prospects who didn’t buy. 

In all that, I couldn’t get excited about anything. It was easier to protect myself by staying home than risking another hurt by meeting new people.

But healing isn’t just acknowledging the pain; healing also requires us to move through those emotions and into new possibilities. When Stanley said, “Guys in their 50's don't have dreams, they have nightmares... and eczema” I saw the next ten years of my life. There I sat, less hair and a softer belly, still nursing the same hurts and the same double scoop mint chocolate chip ice cream. I didn’t want that future. But change wouldn’t just happen to me, I needed to devote myself to it. 

So when Stanley decided to take a bet on Bo Cruz, I started to feel what was missing from my daily routine of coffee, ice cream, and video games. It wasn’t a fairy tale moment for either of us. When he starts waking Bo for four am hill runs around Philly, I felt the urge to set my alarm clock again. The montage of Bo’s training, doing awareness drills and dribbling two balls at once, reminded me of what it takes to get to be a professional. I remembered that self-actualization takes hard work and dedication. I had learned that lesson years ago, when I was a kid training to fly Navy jets. But I still need the occasional refresher.

In all great stories we see a version of ourselves. Watching Hustle, I remembered the version of myself I wanted to be. It’s not that I want to be Bo or Stanley, but I want to remember that fire in my belly that tells me I’m alive. And the only way I’m wired to do that is to set a goal and devote myself to it. Whatever the outcome, I need to know I did everything possible to reach it, and in the process discovered what my true limits were. To discover who I really am. The joy of Hustle isn’t that it taught me those lessons, but that it reminded me that I still had the fire to learn them again.

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An update and a meditation

• I’ve recently started an elimination diet with my doctor to try and figure out why I’ve been getting sick so often. I am not eating many of the things I love, including bread, coffee, and tea. The irony isn’t lost on me after sharing Should I Eat This.

• I’ve been setting an intention to balance the invisible labor at home with a relentless dedication to larger projects. How do we honor our commitments to our families while pursuing our own self-actualizations?

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What are you working on that’s got that fire in your belly lit again? I’d love it if you share in the comments. We can all cheer each other on and, who knows, maybe even find some co-conspirators.