Colin Darretta on the Value of Vices and Intelligent Hustle

“Everyone needs vices,” says Colin Darretta late one Friday afternoon. “Life would be awfully dull without them.”

The thirty-eight year old entrepreneur-slash-investor-slash-writer (it seems everyone is a multihyphenate these days) is reacting to being asked what he doesn’t like in the current entrepreneurial climate. He believes that a puritanical hustle culture has seeped into the popular literature, suggesting that anyone who takes some time for fun and isn’t working a hundred hours a week is just not doing it right.

Still, it’s an unusual perspective from someone like Darretta. He has built a career and reputation on being one of ‘those’ health guys. Everyone knows the type, they always seem to have a green juice in hand and give the side eye when a french fry enters their proximity. Of the five businesses he started his first, WellPath, was a supplement company, and two others, Finn, a dog wellness company, and Grummies, a nutritional gummy business, were both squarely within the nutrition and wellness world.

He and his companies have appeared on the pages of Well&Good, Men’s Health, Vogue and Details to name a few. So he’s not the type one expects to sing the praises of vices. Now, as the CEO of Innovation Department, a venture studio that splits its time between building and investing in early stage brands he exhorts the value of equilibrium.

“Everything in life is about balance – and indulging in some well chosen vices is not only human, it’s healthy,” he says. “That’s what is missing from the conversation today. Too many people waste their bad behavior on things they feel lukewarm about because they repress their vices and then just splurge on something that provides little satisfaction. If I am going to intentionally engage in some activity that is actively unhealthy, then I have to really feel it’s worth it. At the same time, I think people who don’t at least have a vice or two end up being uptight and unfun, two adjectives I hope aren’t used to describe me very often.”  

Entrepreneurs today, if not explicitly told, are made to feel that any time they are not spending building their business is time wasted. Having started his career in investment banking at Goldman Sachs, a profession and firm famous for its ludicrously long hours, he steadfastly believes that is not a model that any entrepreneur should seek to emulate.

“I did some of my worst work at Goldman,” he says. “I was running on three or four hours of sleep night after night and it felt like I was perpetually hungover. I would not want the person doing anything important for me to be in that state.”

A substantial body of research supports Darretta’s claim that sleep deprivation significantly compromises work quality. Lately, these perspectives have received broad acceptance in no small part thanks to Matthew Walker’s Why We Sleep. Goldman, to their credit, has made measures to improve the situation for its junior bankers though Darretta remains skeptical whether it will ever meaningfully shift. 

But what about the narrative that if an entrepreneur isn’t single minded in their ambition to build the next great business they will never climb the mountain? All it takes is a read through any of the seminal books on the great empire builders like Steve Jobs and Elon Musk and the apparent lesson would seem to be that there is a high correlation between single mindedness and success. As recently as 2018, long after he’d “made it”, Musk was still sleeping in the factory.

“I don’t think many people are wired like Elon,” says Darretta. “If you’re not superman then you probably shouldn’t be jumping off buildings hoping to fly. Which is to say, I think it’s a bad practice to try to extrapolate what might work for one incredibly unusual individual and integrate into the common wisdom.”

Instead, Darretta preaches something he calls ‘Intelligent Hustle.’ The crux of it is to work really hard in brief spurts when you’ve got peak focus and energy such that you can enter a flow state followed by similarly long periods refreshing yourself with other activities. The trick is finding a cadence that supports this over a long period.

This echoes the ‘work like a lion, not like a cow’ methodology that has been espoused by startup world cognoscenti like Naval Ravikant. In it they suggest any high performer, but especially those in creative fields like business building, work in sprints of a length where they can dedicate undivided attention to the task at hand. Then, after they finish the sprint, they can relax and assess their progress. This gives them both time to get energy for the next sprint and, crucially, let their prior actions and results inform their next effort. 

“People who say things like ‘if you’re not working on the weekends you’re not trying hard enough’ are misguided,” says Darretta. “Will the circumstances sometimes require someone to grind away on a weekend? Undoubtedly. But it shouldn’t be the expectation. If you don’t take time to recharge the battery and leave empty time for other activities alongside free thinking then you’re not going to be very good at your endeavors nor will you even endure the very long process of business building.”

Darretta’s experience – at this point he’s founded or co-founded businesses with combined valuations in the nine figures – has given him a certain degree of credibility within the startup community. And his views, though contrary to what is the common wisdom in hustle culture places like Twitter, are generally well received.

Perhaps that is precisely because his views are so clearly in conflict with the virtue signaling that many entrepreneurs engage in as they endeavor to at least manage the perception that they spend seven days a week in the office and never have a night out, let alone take a vacation. Some of it is presumably done that way because there is what Darretta calls “a temptation to show investors that you’re single minded in your pursuit of your entrepreneurial vision.” 

“Some of the investment community is to blame here, certainly,” says Darretta. “And that’s a hard thing for me to reconcile, because I’m guilty of it. As an investor, I get excited when an entrepreneur comes off as singularly focused on achieving their dream at the expense of everything else. When it feels like it’s the only thing in their lives you walk away saying ‘they’re just not going to let it fail and that’s who I want to bet on.’”

There is no pat answer then, he admits. While investors may get better at paying lip service to wanting entrepreneurs to live a balanced life it is hard for them to not at least subconsciously get excited by the ones who seem to have no life outside of building their business. Over time, Darretta suggests, there has to be a gradual shift on everyone’s part: entrepreneurs not to virtue signal and investors not to reward it. 

“Ultimately, most of the entrepreneurs I know who’ve built billion dollar businesses still found time to have a life outside of work,” says Darretta. “And not just once they’d made it but during the process. Most of them didn’t have a straight line to success and the only way they persevered long enough was working not just harder than most people but smarter. They were really good at finding a little time for vices and fun along the way to balance out the intense pressure they were under. That’s certainly one small part of what made them so special.”

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