The Smartest People I Know #3: Meet Ryan Holmes

Welcome back to The Smartest People I Know: a monthly series where I share the wisdom of some of the incredible people I’ve met on my career journey.

Let me know what you think in the comments — looking forward to keeping the conversation going.

Meet Ryan Holmes, Cofounder and Chairman of Hootsuite

I first met Ryan Holmes when I joined his Vancouver-based startup back in 2011, working on a little social media management tool called Hootsuite. We’ve both gone our separate ways since then, but Ryan will always be an inspiring figure to me. After all, he grew a spark of an idea into a platform with more than 18 million users worldwide, and continues to be a thought leader in social media, with projects like his book, Saving Social: The Dysfunctional Past and Promising Future of Social Media. Recently, I was lucky enough to catch up with him about some of his biggest career takeaways.

The secret to fulfillment in work (and life) is … Be constantly learning; if you’re not learning and challenging yourself, you’ll end up getting bored.

The best career advice you’ve ever received? If you want to do something at scale that’s impactful, you need good people with you on the journey. It’s really all about the people.

The worst career advice you’ve ever received? This wasn’t advice as much as an attitude: that sleep isn’t important. I’ve seen so many people log 80-hour work weeks with pride. But it’s so counterproductive.

What’s the most under-rated skill for leaders? Communications. When you’re a small team, communication is easy. But as a company gets bigger, it becomes exponentially more challenging. Think about it: When you’re leading thousands or tens of thousands of employees, communications is your only tool to reach them.

How do you know when a business venture has legs? User adoption is an easy signal that a business has legs. On the other hand, you may be “ahead of the wave” — and have a great idea but the timing isn’t quite right. Then it’s up to you to decide if you ride it out or move on.

We’ve all experienced little moments that end up changing everything (a conversation, realization, accidental encounter). Could you share one of these moments, in the context of your career? One moment that gave my spine shivers happened when we were launching Hootsuite and had lots of users onboarding. One day, we noticed that the White House and Barack Obama were using us. At that time, we were less than 30 people and realized, wow, this is going to be something big.

“Use your beautiful life to build things.” — Ryan Holmes

What I’ve Been Reading (and Writing)

The Importance of Soft Skills: I found this Forbes story about the most important skills post-pandemic to be spot on.This strange period of time has tested all of us — but one silver lining is that it’s emphasized the importance of empathy, emotional intelligence and communication in the workplace.

100 Years of Robots: This interactive Wall Street Journal piece was a fun walk through the history of robots, starting with a 1921 Czech play that first introduced the word “robot” to the world. Our picking robots would fit quite nicely into this list …

How to Use Start-up Hacks On Your Own Career: Thrilled to have my story about using start-up principles to kickstart your own personal career featured in Entrepreneur this month. Over the years, I’ve seen first-hand how concepts like growth hacking, beta-testing and pivoting can help businesses — but I truly believe they can be used to supercharge one’s own professional path, too.

Reader Feedback

I recently asked my LinkedIn followers about what they look for when promoting someone, and, as usual, the responses were thought-provoking. This comment from Evan Santa, vice president of sales at Contractor Compliance, was such a powerful one — a reminder to not just look at someone’s achievements on paper, but to also trust our instincts.

I’ve always held the premise that if someone is promoted, peers around them should internally think “that makes a lot of sense.”

Thanks so much to Ryan Holmes for sharing his words of wisdom with me — and thanks to you for reading. If you found The Smartest People I Know interesting, feel free to follow me here or on LinkedIn … or, better yet, share this with the smartest person you know. More to come next month!

President and COO at @BerkshireGrey. Curious, family man, technology veteran, traveler. I help cutting-edge companies scale with purpose.

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