Ryan Holmes is sitting on a park bench in New York City talking about starting a mafia. The founder and CEO of the social media company HootSuite is Canadian and handsome. That is to say, he wears a beard upon his face, his hair is somehow both slicked back and messy, sunglasses dark and chunky. But even through the shades, you can see a twinkle in his eye when he talks about the future of HootSuite, now five years old.
"Ultimately, I'd love to see a legacy company that has alumni that come out of it and go on to create other big things," the 38-year-old entrepreneur says. "A maple-syrup mafia, a HootSuite mafia."
The language seems most appropriate: maple syrup, after all, is very Canadian and also very handsome. And "mafia" is startup-speak for a group of awesome employees that go out into the world to do awesome things. (The PayPal mafia, as you may know, is a force in Silicon Valley.) Now at over 350 employees, more than 7 million users, and 300% revenue growth in the second quarter, HootSuite itself is becoming quite the large family. But for Holmes, the mafioso mentality is an outgrowth of making the startup a long-term thing.
About five years ago, Holmes got jolted into thinking about his own longevity.
He made the unwelcome discovery of herniated discs in his back, the product of years spent snowboading, playing football, doing judo, and the long sedentary hours spent running businesses. That injury led him to yoga—the days when he doesn't practice, something's just a bit off—which would help him sustain himself over the long term. It's an orientation that carries over to the company culture.
"For everybody in their busy lives, you need to invest in sharpening your tools and you need to invest in longevity," he says. For a while, you might feel like you can get away with not doing so—when you're 20, when you're 30—but eventually it hits the fan.
"You're effectively creating downstream debt," he says. "You get sick, you get injured, or whatever it is."
"You can run a sprint or your can run a marathon," Holmes says, "but you can't sprint a marathon."
As you may imagine, HootSuite, at launch, was in sprint mode; now they're more about endurance. And from Holmes' captaining, focusing on endurance lends a holistic quality to the hustle.
"If I'm building a legacy company here, I need to help people be healthy throughout their lives." he says. "I think about this back injury that I had. Probably a lot of it was from being a stationary worker, sitting down on my ass all the time."
So HootSuiters cover their ass in a different way: for one, there's been a movement of working at standing desks. Second, cold-pressed juices are arriving on daily. Three, there's a well-attended yoga studio in the office. And four, there's a nap room, because, grabbing a cup of coffee, splashing water on your face, and then drooling in front of your computer isn't exactly crushing it.
A man deeply involved in the growth of social media is clearly acquainted with the phenomenon of the long-hour humble brag: "When you puff your chest up and say 'I work 21 hours in a day,' " he says, "there's a 'little bit of machismo' to it." Rather machismo, it's knowing how to do your best work that could land you in the Maple-Syrup Mafia.
"It's a little bit draconian that managers are thinking that they're getting more out of people if their employees are chained to their desk," Holmes says. "I'd rather find people that can work smarter."