Why it took 8 years for me to become CEO of my own company

I’m a first time entrepreneur, having cofounded a niche publishing company. For more than eight years, I have been among those most responsible for the organization’s longterm strategy. For most of those years, I played the role of public face, among the first to serve very nearly all the roles we now have. We have a team of more than 20 and invoiced for nearly $1.7 million in 2016, all of which I feel responsible for supporting and growing.

But only today did I take on the title of CEO.

No one had ever held the title at our organization before. In an era championing entrepreneurship and fetishizing the young and the innovative, we are quick to anoint untested first time founders as chief executives. How many one person or four person companies do you know with a first-time CEO? It’s meant to offer clarity and it’s a great resume line. I am going to tell you why I think that’s a mistake. It’s also why it took me eight years to feel comfortable calling myself an organization’s CEO.

Like most young companies, in our earliest days, we were a team that made decisions on consensus and flowed and shared between roles. First among cofounders and even then among our first teammates, we divided up core responsibilities. Some that I more naturally gravitated to fit a CEO paradigm — making early culture decisions, serving as initial spokesman, holding us to mission and strategy.

Every few months for the first year or two and then almost as often for years after, my cofounder Brian and I would talk about our own roles and responsibilities. (As I take on CEO, Brian is becoming Chief Business Development Officer). We split the critical business, marketing and operational efforts, and so we used the “cofounder” title flexibly. We supplemented when it helped the work get done. For me “cofounder” hid dozens of roles in sales and finance and HR, and my secondary titles reflected my leading our journalism.

1. For the first three years (2009 to 2012), I was Cofounder and Reporter.
2. Then when we hired our first reporter, and I was Cofounder and Editor (2012 to 2014).
3. Then we hired our first editor, and I was Cofounder and Editorial Director (2014 until yesterday), the first title in a truer organizational hierarchy.

At each of those transition moments and surely times before, Brian and I talked about whether we should take on titles that made clear we were the primary leaders of the organization. A handful of times I was asked in earnestness if a teammate of mine was my boss, and when I think about that now, I recognize that as a kind of victory. For the communities we served, in an external way, we were growing our team in large ways by consensus, and we were encouraging new members of our team to take stages and independence.

The title of CEO specifically or any C-level generally means something to me. I’ve always felt titles (like all words, in my field) can mean a great deal if you give them substance. For me a CEO is someone who is ultimately responsible for maintaining and growing an environment that suits the kind of people an organization needs to thrive. It’s someone who is ultimately culpable for all an organization’s failures and whose only credit for an organization’s successes comes for bringing that team together. If it’s a crummy place to work, that’s the CEO’s fault. If it’s a great place to work, the CEO only deserves the credit for getting the right people in that organization to make it so.

Congrats. You've really built an amazing company!!

— Josh Kopelman (@joshk) July 1, 2017

Looking back, I’m very proud of how often Brian and I resisted slapping on C-level titles. We simply never forced it, and good thing because we weren’t ready for that kind of responsibility.

For the last three years the “cofounder” portion of my title has continued to cover an array of responsibilities, but we’ve whittled them down as we’ve gone from a team of five to 10 to 15 to 20 and beyond. I still oversee our newsroom, programming, messaging and community connectivity. For all those years, When I was getting business done or needed to shape shift into other roles for meetings or ideas, my cofounder distinction is what allowed me to do that.

The critical point here is that as first time founders, Brian and I have been growing as young leaders too. I fully understand that someone who feels comfortable in the role should assume that title for clarity and other logistical reasons. If I were to start another company, I might start with that title — though perhaps I wouldn’t. But I do know now I feel the title means something to me. (*Also my friend Jess Gartner notes that some investors like to see a CEO listed as primary fiduciary contact, and that again is a specific reason why you’d have that title early. My point here is it should be for a reason. She has one. I didn’t until now. Thanks Jess! )

I’m 31 now. I started this company when I was freshly 23. I struggled without a teammate to mentor me, to tell me no, to help shape me — it’s one of the warnings I give to young founders: there very much is value in being seasoned by those more experienced. But of course growing a company in your 20s is also one of the best times to do it for the first time, to learn and experiment. Brian and I needed some way to challenge ourselves to grow. One way we found that was with reality based titles. We’d do c-level work because it had to get done, but we weren’t doing it at the level we wanted to be, as the kind of competitive professionals we are.

I wasn’t a CEO when I was 23. I feel like I’ve been interviewing with my coworkers ever since. I’ve made mistakes, lots of them. I recognize that I still have a considerable amount more to learn to get to where I want to be, the kind of leader I want to be. But I’ll tell you this: I feel ready now. I am a CEO at 31. That means a great deal to me. I also know at 31, I’m the worst CEO I’ll ever be. I’m going to get better at that every single day I’m privileged enough to have the role.

Looking back, rather than take on a leadership title I hadn’t truly earned yet, we grew our company organizational chart organically, as we saw various teammates grow. In the quiet moments from afar, who stepped in to want to solve the biggest problem? Who was the best teammate to the most people? Who wanted what when?As that coalesced, it became clearer the structure that would allow us to move collectively and as individual units. That’s how our leadership structure had grown, by the people who have been inside our organization, not because I wanted people to report to me.

This year, what changed was that increasingly what we most needed was distance between me, a cofounder, and an increasingly able and independent team. I needed to let daily goals fly with new leaders, and I now need to devote more time to new ground. What I needed was an org reset and a title that could represent a change for both our team and external partners.

Finally it was a specific reason for why a change was necessary, not an arbitrary one. Look, I like this change, it’s fun. It’s a pretty title. But I can look anyone in the eye and say that we made this decision not because I think it’s neat but because it is the best thing for the organization I help lead and for the couple dozen people it employs.

Helpfully I’ve used this transition also to mean something — from cofounder to CEO (startup to small business) and even from Editorial Director to CEO, a big promotion that carries with it considerable responsibility. (You can bet I loved editing a piece on how to transition gracefully from founder to CEO, and am always reminded that not all founder should become CEOs. This is a different role with different responsibilities)

I think a lot about the advice I’ve given and expect of my team. I followed the same pathways for my own promotion: I did what the team needed and I served the role for long (in truth maybe too long) before I got the title for it.

I’ve had a few conversations in the past few months — ones with clients and staff and partners. I still am challenged but I’ve found myself so much more in control. This did not come quickly. I feel like I have earned it. I feel like I have learned more here than in anything else I’ve ever done. For those reasons, this means more to me than it ever could at any other time.