How Following His Heart Led This Entrepreneur to Start a Multi-Billion Dollar Company
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Editor’s Note: Entrepreneur’s “20 Questions” series features both established and up-and-coming entrepreneurs and asks them a number of questions about what makes them tick, their everyday success strategies and advice for aspiring founders.
Ryan Holmes initially ignored his high school guidance counselor’s advice: follow your heart. But when he finally realized the value of the advice in 2008, Holmes was able to turn his passion for social media into a platform that operates in more than 175 countries.
It wasn’t easy to get there though, Holmes was told by an angel investor that his idea to harness social media was never going to work. “He told me the idea of a platform for managing all this had little potential, and I should probably rethink my proposal,” the CEO recalls.
He didn’t take no for an answer though. We caught up with Holmes and asked him 20 questions to figure out how he founded and continues to run Hootsuite, along with what makes him tick.
1. How do you start your day?
The first thing I do in the morning is check my social-media feeds. I have a stream set up to monitor any references to Hootsuite, and this is kind of a sanity check to make sure nothing blew up overnight. With that out of the way, I try to set my mind to think about the big to-dos of the day.
2. How do you end your day?
I end my day the same way. Before going to sleep, I’ll give my social feeds one last skim. It’s a way to get a quick pulse check on the company and see what users are talking about, what issues we may need to address and what features are working well.
3. What’s a book that changed your mind?
The Long Walk: The True Story Of A Trek To Freedom is one of the most amazing, heroic stories of this or any other time. It tells the story of author Slavomir Rawicz, a Polish soldier who is imprisoned by the Soviets after World War II. To gain his freedom, Rawicz goes on a remarkable journey through the frozen Siberian tundra, the Gobi desert, the Himalayan Mountains and to India. The Long Walk is about everyday human struggle, overcoming obstacles and achieving the impossible. That’s why I keep 10 copies on my desk to give away at any moment.
4. What’s a book you always recommend?
An Astronaut’s Guide to Life on Earth by Canadian astronaut and International Space Station commander Chris Hadfield. He’s a friend and one of the most courageous and inspirational people I know. In the book, he shares some incredible stories from his life as an astronaut but also shows us how to make the impossible a reality whatever pursuit we’re in. I recommend this to anyone who dreams big and who strives to stay true to themselves.
5. What’s a strategy to keep focused?
Like lots of entrepreneurs, my attention is always pulled in a dozen directions at once. The one thing that really helps me stay focused is exercise. After I jog, do yoga or get out and do some backcountry skiing, I always come back with more clarity and focus.
6. When you were a kid what did you want to be when you grew up?
I wanted to be a video game developer. But after high school, I decided to do the practical thing and study business in university. That turned out to be a mistake. I dropped out and opened a series of businesses, including a pizza joint, before finally getting back to what I originally loved, in a way, with Hootsuite.
7. What did you learn from the worst boss you ever had?
This individual was a bad boss but definitely not a bad person. I was working at a small dot-com, and he just didn’t know enough about software development to be effective. He’d give unrealistic timelines to build impossible products, like “I need you to build Yahoo by tomorrow.” All the developers would just nod and agree but of course, the projects were never completed.
8. Who has influenced you most when it comes to how you approach your work?
My parents. My mom was originally an art teacher, so she was really in tune with design, aesthetics and creativity -- all things that have been so important with Hootsuite. My dad was a math teacher with a much more analytical way of thinking, which rubbed off on me, too. I think this left-brain-right-brain dynamic has guided a lot of what I do.
9. What’s a trip that changed you?
Shortly after Hootsuite launched in 2009, I took a trip to Japan to meet up with some of the users of our product. We were popular in Japan from the start, with little marketing in the region, and I wanted to understand why. It was amazing to see that Hootsuite was having an impact on people’s lives halfway around the globe.
10. What inspires you?
Building products that solve the pains of real people is one of the most exciting things you can do. Recently, I also worked on a side project called Oristand: a $25 standing desk made of cardboard. We were flooded with grateful comments on social media from people who had desperately wanted a standing desk but weren’t able to pay hundreds of dollars for one. That was really satisfying.
11. What was your first business idea and what did you do with it?
I was a huge paintball fan as a kid, but it’s an expensive hobby. In high school, my brother and I had the idea of starting our own paintball field near our home in British Columbia. It was a crash course in business -- everything from marketing to pricing and filing your taxes.
12. What was an early job that taught you something important or useful?
When I was 12, I washed the windows of my mom’s clothing store for $5, and soon I was approaching other local businesses to wash their windows. There really wasn’t anyone offering that service in town, so it was an early entrepreneurial lesson: Find a void and fill it.
13. What’s the best advice you ever took?
Follow your heart. A guidance counsellor actually gave me this advice in high school, but I ignored it. I loved computers and video games at the time, but I just didn’t think there was a career in it. So I went on to study business in university. It took me about a decade to realize the error of my ways and get back to my true passion.
14. What's the worst piece of advice you ever got?
Early on, I was pitching Hootsuite to a local angel investor. He just couldn’t wrap his head around this new thing called social media. He told me the idea of a platform for managing all this had little potential, and I should probably rethink my proposal. I still see the original investor who passed on us all the time and he never fails to express his regret.
15. What’s a productivity tip you swear by?
When answering emails, I tend to use the three-sentences philosophy. This approach, effectively treating all of my emails like short SMS text messages, has worked extremely well for me. I’ve trained myself to leave out the fluff and keep only the most essential points in an email. If I absolutely have to say more, I just pick up a phone or talk in person.
16. Is there an app or tool you use in a surprising way to get things done or stay on track?
I tend to use my email inbox as a catch-all for everything. But it’s a hassle to have to fire up my Gmail and compose a message just to remind myself to bring home milk. That’s why I really like Squarespace Note. It’s an iPhone app that you can use to jot down notes whenever, and it will automatically send them to your email inbox. Not super high-tech but very handy.
17. What does work-life balance mean to you?
It’s a moving target. It’s not like if I work 40 hours this week I’ve achieved balance or if I work 80 hours next week then everything is imbalanced. I try to ride the line between not being challenged enough and being over-challenged.
18. How do you prevent burnout?
Exercise has always been my outlet. Growing up in rural British Columbia, I developed a love of the outdoors and my passions generally reflect that. Snowboarding, cycling and cross-country skiing are some of my favorite pastimes, as well as surfing and scuba diving. I also enjoy yoga. I found yoga a great way to clear my mind and come back better equipped to handle the fire hose of demands.
19. When you’re faced with a creativity block, what’s your strategy to get innovating?
I find that lots of problems work themselves out if you just give them time. I try not to rush to decisions or judgement if I don’t have to. Neurologists have said that we essentially have two decision-making systems: a quick brain and a slow brain. The quick brain is good for keeping us alive out in the physical world. But we often neglect to stop and allow our slow brain time to do some of the processing. I get some of my best and most original ideas after a good night’s sleep or in the shower.
20. What are you learning now?
At this point, what I’m learning is how to continue scaling while also managing a more mature company. The demands now revolve around streamlining processes and improving efficiency, while also ensuring that we continue to innovate -- which is critical in a fast-moving space like social media.
This interview was edited for brevity and clarity.