When to Move On and What You Leave Behind ~ Ryan Holmes in the WSJ

Image by Shankar s.
Image by Shankar S.

This post originally appeared in the Wall Street Journal. View the original here.

It’s not like I was looking for a change. I had started Invoke – a little company that built web pages and Internet apps – in my apartment when I was 26. As the months turned into years, I hired one employee, then another and another and finally brought on partners. We struggled (a lot) but stuck with it. By the time our eighth Christmas party rolled around, there were 21 of us, and we needed a new office.

Then, during a rainy stretch of days in late 2008, one of our teams hacked together a nifty little tool for managing multiple social media accounts. Instead of signing into Facebook and Twitter and LinkedIn separately, you could do it all from one dashboard. It was rudimentary, but – before long – the app had hundreds of thousands of users. And, suddenly, I had a decision to make.

At the time, Facebook was adding tens of millions of users a year. Something called Twitter was just taking off. Social media was still looked at as a dorm-room toy back then, and nobody knew how to monetize it, but some kind of cultural sea change was definitely happening.

So, I jumped in and left  my existing role at Invoke. I spun off our social media tool into a brand new company called HootSuite. I handed over the reins at Invoke to my partners, and I took the helm of an untested, unprofitable business with no paying customers and no investors.

It was among the best decisions I ever made.

Should I stay or should I go?

The decision to leave a company you founded  and move on to a new project is never an easy one. You leave behind years of work and often a stable, promising business for a world of unknowns. For me, opportunity knocked. Given the choice between plugging away at a sure thing and hitching a ride on a rocket ship, I climbed aboard.

Passion, of course, also comes into play. This is a cliche in many ways, but if going to the office every day no longer excites you, then there’s a problem. Entrepreneurs, by disposition, are built to think big. When a role no longer affords those opportunities, it might be best to leave it in capable hands and move on. The longer you’re stuck in a position that doesn’t truly challenge you, the less likely you’ll be able to leave it. Inertia, in fact, is one of my worst fears.

Changing the guard or changing everything?

Of course, a changing of the guard at an established company always brings turmoil – sometimes for better and sometimes for worse.

A critical question to ask when bringing in a new CEO to take the reins of a company you started is: Do you want someone who will maintain company culture or reinvent it? Take Marissa Mayer, who joined Yahoo! as CEO in 2012. At the time, Yahoo! was slipping into irrelevance and in need of a shake-up. In the intervening year, Mayer has managed to radically overhaul the company’s culture and image. Yahoo! is – if not quite cool again – then at least getting there. More importantly, the company appears to be righting its financial ship.

For thriving companies, however, preserving corporate culture during a regime change can be just as important. Town halls and question-and-answer sessions can be great ways for a new chief to gauge sentiment and share expectations. Meanwhile, internal social media tools can help break down hierarchies and give employees a direct channel to engage with a new boss. At HootSuite, we also hold regular Ask Me Anything sessions (modeled after Reddit’s online AMAs), where I field anonymous questions from employees about, literally, anything. It sounds gimmicky, but the discussions can be deeply revealing.

Success and the serial entrepreneur

Tech is increasingly a field dominated by serial entrepreneurs. The Bill Gates and Mark Zuckerbergs of the world – founders who dedicate their life to one venture – are giving way to a new generation that leapfrogs from one passion to the next. Given the pace of technological change, this probably shouldn’t be surprising. But the real challenge, and the heart of serial entrepreneurship, lies in pursuing new passions while also leaving a team in place to keep growing and innovating once you’re gone – something often easier said than done.