How Being A Solo Entrepreneur Helps Me Run A 1000-Person Company

The great thing about the CEO title is that you can give it to yourself. At least, that’s what I did. Back in 2000, the tech bubble had just burst, and I was out of a job. So I founded my own web agency of one — called Invoke — out of my apartment, and appointed myself CEO. I had already started a paintball field in high school and a pizza joint after college. So, entrepreneurship felt like the right fit, from day one.

To be honest, I don’t remember my first day at Invoke very well. I probably rolled out of bed, turned on my computer and started building web tools. I had a background in web design and development and, despite the temporary economic downtown, those services were in demand. After a few months, there was enough work to hire my first employee. Then came a few more. And a few more. After several years, Invoke had 20-plus team members and we were doing everything from building tools to handle video campaigns to managing social media on clients’ behalf.

And that’s where the idea for Hootsuite entered the picture. It was a headache to constantly log in and out of different clients’ social networks, so my team hacked together a tool to monitor multiple accounts, all from one dashboard. We quickly realized that lots of other businesses needed a tool like this, too. In 2009, I made the decision to spin out Hootsuite as a separate company.

This time around, my first day as CEO was a bit more nerve wracking. On the outside, not a lot had changed. I was actually in the same office — we just tore down a wall to make some more room. And I’d taken seven employees with me from the original company — so there weren’t any unfamiliar faces. But in another respect, I’d left all I’d built at Invoke behind, under the management of my partners. In addition, for the first time, I’d decided not to bootstrap and instead secured financing. So I had investors and employees to think about, despite having no revenue coming in. The project had considerably higher upside — and considerably higher risk — than anything I’d attempted before.

The experience of starting over again was overwhelming, but also exciting — I think as an entrepreneur there’s nothing more exhilarating than being in the early stages of getting a really promising idea off the ground.

The employees around me were, luckily, all self-starters. With only seven team members, there really wasn’t any hierarchy or organization. Everyone appreciated the huge (and daunting) opportunity in front of us and really threw themselves into finding a way forward — even when that meant going beyond their usual job description. I think it’s critical to the success of any startup to have these kind of folks early on — adaptable, egoless, and with no pretension or attitude.

Looking back, right from that first week, I think we managed to get a few things right that really helped in the long run as Hootsuite grew to dozens, then hundreds of employees. Most importantly, we prioritized culture. We may have been small, but we took the time to go for a bike ride at lunch or share a barbecue on our rooftop after work. In hindsight, that stuff isn’t fluff — it’s what makes a job something that people can believe in and get behind.

On the personal side, the first week was a whirlwind for me, with lots of late nights and endless fires to put out. This was compounded by a back injury at the time which left me walking with a cane for a year. I had cobbled together a DIY stand-up desk from cardboard boxes and managed to soldier through with a lot anti-inflammatories.

Though I was super busy, I also found time for yoga classes. Not only was this helpful for my back, it also afforded a space to reflect and reset, which can be so critical when faced with stress and monster to-do lists. I’m so thankful that I carved out a little time for that.

CEO lessons that keep on giving

Fast forward to today, and I’m now the CEO of a company of around 1,000 people. In some respects, everything has changed from the days of running a business out of my apartment. We now have more than a dozen offices around the world. We work with 800 of the Fortune 1,000 companies. I have a whole team of brilliant senior executives to advise me. But, for other leaders out there, I think it’s important to emphasize that not everything has changed. In fact, many of the skills I learned as the CEO of a company of one still serve me as CEO of a global company with more than 16 million users.

The most critical lesson that I carry with me is the importance of being a jack of all trades and master of some. As the CEO of a tiny company, this is a matter of necessity. To get off the ground, I had to learn — largely on the fly — about nearly every facet of running a business: product and engineering, sales and marketing, accounting and finance, customer service and client relations, human resources and more. The process of building a business, from the ground up, truly represented a mini MBA for me. In hindsight, this was actually a luxury that a lot of my peers — who dove right into leading fast-growth, venture-backed companies — never had.

I’m not saying I was an expert coder or sales guru. But I learned enough to be dangerous. I understood enough product development to vet the developers I was hiring. I had learned enough about sales to hop on calls with key customers and drive a deal home. I learned how to make a compelling pitch to investors. Really, I had no choice. Either I gained a basic competency in these areas or the company died on the vine.

Eventually, though, I also learned an equally important lesson. As you move beyond the early startup stages, the quickest (really, the only) way to accelerate growth is to aggressively delegate and not try to do everything yourself. As soon as you’re able, in other words, hire people who can do specific jobs better than you can. Hootsuite had just a fledgling sales team, for instance, when I brought our first chief revenue officer into the picture. With plenty of past experience scaling global teams at major companies, he quickly grew our sales org and set us on course to target huge businesses.

These oppositional skills — knowing enough to be dangerous but knowing when to delegate — continue to serve me as a leader today. The blend of general competence and humility isn’t always easy to get right. But, looking back, being CEO of a one-person company can be great training — whatever size company awaits you down the road.

A version of this piece originally appeared in Business Insider.

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