Ryan Holmes founded social media management start-up Hootsuite in 2008. A serial entrepreneur from his high school days, the Canadian is also a notable proponent of the B-corp sustainable business model.
How did your first elevator pitch go down?
I was pitching Hootsuite to a local angel investor here in Vancouver, but he just couldn’t wrap his head around this new trend called social media. Why would people share pictures and updates online, sometimes with complete strangers?
Luckily, he did refer me to a Seattle angel, and we were able to secure some funding. I still see the original investor who passed on us all the time and he never fails to express his regret.
What skill or quality have you had to work at the most in order to be successful as an entrepreneur?
I’ve had to work the hardest at focus. I think by nature entrepreneurs are easily distracted. You get very good at identifying opportunities, but the real challenge is in the follow through. When you’ve found something with potential, how do you stay the course rather than being distracted by the next shiny object?
What was your worst moment of doubt and how did you overcome it?
Back in 2008, I was running a small digital agency called Invoke. A few team members had hacked together a tool for managing multiple social networks at once. I thought it had huge potential, but it wasn’t bringing us in any revenue at the time.
Despite that, I made the decision to dedicate seven people from my 21-person team to this project. For a while, I was using my personal credit card to pay their salaries. It was scary, but I thought social media had so much potential.
How did you build Hootsuite's corporate culture?
I don’t think you wave a wand and create a corporate culture, and it’s not really something you can dictate from above. From the start, I hired people that I felt shared some of the same values as me: hustle, intellectual curiosity, a degree of humility. Overtime, those values started to take root and define our culture here at Hootsuite.
What do you look for more in new hires - qualifications or experience?
There is no right answer here. Personally, I dropped out of university to start one of my first businesses. And I felt I learned a lot more from that experience than I did in school. At Hootsuite, almost all of the positions we advertise for explicitly say ‘degree or equivalent experience’. There’s a lot of learning that happens outside the classroom, especially in a space as new as social media.
What keeps you up at night?
What keeps me up at night is thinking of ways to exponentially grow Hootsuite. I think we’ve only just begun to tap into the potential of social media. It’s a cultural shift that will change how people interact and do business for decades to come. I’m looking for ways we can boost our current business not just incrementally but ten-fold by better tapping into these changes.
When do you think is the right time for entrepreneurs to get outside funding?
Is your industry poised for growth? Is the competition threatening to outpace you? Do you need capital to grow and stay in the game? Then it’s time to look into financing options. This might seem obvious. But when you’re sweating it out in the trenches, trying to do the thousands of things needed to get a startup off the ground, it can be dangerously easy to overlook.
On the other hand, if you’re working in a less competitive space that’s moving more slowly, it can be advantageous to bootstrap and retain equity.
What do you wish you’d done differently?
I honestly wouldn’t change much. I’ve made lots of mistakes, but the lessons I was able to take away helped me down the road. For instance, I spent too long bootstrapping my company in the early days. It was almost a matter of pride to fund everything myself.
But once I was able to see the multiplier effect of outside investment, I didn’t look back. As a result, Hootsuite was able to grow faster than its competition and ultimately dominate the social media management market early on.