Being the Other Founder

When Ted and I were starting GameChanger, we met with one of my mentors, Kevin. After talking through our plans for the business, he nodded toward me (the technical one), and said, “you need to quit your job immediately.” He then turned and looked Ted (the HBS grad and idea guy) in the eye and said, “you’re optional for at least 6 months.”

It’s glorious to be the technical founder, or even the “get things done” founder, early on. The CEO role at the beginning feels ornamental, while the more practical skills and scrappy execution that are often what the other founders and early employees bring feel critically important and unbelievably valuable — and they are!

Three years in, things were very different. The transition I had to make from “smart hacker generalist” to “other executive leading the company” was one of the two hardest things I’ve ever done in my life. I started to see other companies that were a little further along than GameChanger was, and in general, the CEO is always the CEO, and that role becomes more well-defined and more critical the larger the company gets. At 25+ people, the biggest existential crisis facing most organizations is whether they can hold their culture, focus, and purpose clear as the organization matures, and that’s one of the primary jobs of the CEO. The other founders… I started to realize that in many companies that had scaled up past 50 people, they were often gone, and when they weren’t, it was a common pattern to see them taking on functional roles within the organization as senior contributors, but not executives.

There isn’t anything wrong with taking on a role as a contributor as the company grows — for many founders, it’s a much less stressful and more natural thing to, say, want to stay deep in the technology. You started this company to build something, you probably left corporate life because you weren’t so interested in the ladder, and what it means to be an executive at a growing company is a lot more management and communication than “getting things done.” But it’s a hard transition.

At GameChanger, I made a different choice: as I saw the organization grow, I realized my addiction was to impact, and not to any specific act of creation (even though I love love love love building things). I looked around, and every year for the last 4 years I was there I changed my role to adapt to what the company needed. I asked myself what, with the credibility and clout I had from being a founder, I could do best to help the company succeed, and I took a deep breath each time and charged in.

I first handed off engineering to Phil Sarin, who was a more focused, thoughtful, and capable leader in the era of scaling and reliability than I was prepared to be. In hindsight, I should have made that shift earlier, but my ego was too tied up in the coding back then. I gradually handed off even the technical visionary parts of my job to him and his team, and looked around to see what else I could spend my time doing.

For the next year, I was Chief Product Officer and effectively the product manager for three teams at once. I took advantage of one of our VCs hosting Marty Cagan doing a seminar on product management to get some better fundamentals, reached out to every senior product person in my network for advice, and read half a dozen books on it. I tore into the problem and created a whole process and rigor around product that had been missing in the company. It was fantastic, and I was useful and impactful again.

About a year in, though, Phil and Brooke (my VP of Design) came to me and told me that I had become the bottleneck again: every day there was a line outside my door for decisions and input on design, technology, and product direction, and I still had other founder duties (board meetings, fundraising, recruiting, interviewing, reporting, etc.) that were cutting into it as well. I turned one of our engineers into an awesome and effective junior product manager to stop the bleeding, and then I went out and found Ron Feldman to take over product management and build a real organization around it.

A week after Ron started, I realized that I had succeeded again in finding someone more expert and dedicated than I was to lead product, and I needed to drop my CPO title to give him a clear mandate. Existential crisis time again!

But again, I found a gap: Ted is a terrific operational mind, but his role kept him busy with fundraising, investor relations, business development, and leading the company — so over the course of a few months, I worked with him to carve out a COO role, converted yet another engineer (this time into an Operations Analyst and general second-in-command), and gobbled up books on finance, accounting, goal setting, measurement, and strategy. I had a blast, built out more mature processes, implemented OKRs, hired expert contractors, and worked on our subscription pricing (thanks Stephen), financial model (thanks Rusty) and market research (thanks Sarah). Every new project was a learning experience, and mattered to the company.

I left GameChanger this past February, after more than 8 years, feeling like I had learned more and grown more than I could possibly have imagined. By that time, I’d handed off everything that used to be a specialty of mine to someone else who was more of an expert than I was — and while there was still fun work to be done coordinating it all, I felt like my job was done.

Being the “other founder” the way I did it is not for everyone, and it was brutally hard, both intellectually and psychologically, to go through it. I hope that more technical and operational founders (non-CEOs) are able to see this crisis coming, and be more prepared for it than I was. It’s painful to realize that you might be optional as your company grows, but it doesn’t mean you’re any less valuable a person. In the beginning, enjoy being critically valuable and having the chance to build something amazing. It’s a privilege to get to do that! As you grow, though, maybe keep the following directions in the back of your head:

  1. Be a functional executive: CTO/VPE, CFO/VPF, CMO/VPM, are critical roles as a company grows, and if you’ve got the expertise and management chops and interest, aim toward one of these roles. Be aware that with more growth, even that role will fragment into executive versus functional management over time, and you’ll have to look hard at the decision again then.
  2. Be a builder: many founders end up being happiest continuing to contribute in the way they did at the beginning, and letting management fall to professional managers: be a designer, an engineer, a salesperson, or whatever you do best that’s going to help the company grow. You are still a leader and a legend, you still get to have equity and influence, but if that’s the right work, put your ego aside and do it.
  3. Adapt: I think I was able to take the path I did because I’ve always been a generalist, and I have a hell of a motor and love to learn and adapt. The way that Ted and I talked about my role as COO was effectively that I could be the “other leader” in the company, and he and I could share the load in whatever way made sense. That’s a complicated thing to do, requires a deep mind-meld with your CEO partner and a lot of negotiation and willingness to survive the inevitable conflicts, but it can be really productive if you and your co-founder(s) work well together. You’ve got to be a solid manager and generalist thinker, be willing to let your ego go and work more behind the scenes, and roll up your sleeves and learn like hell to do it!
  4. Move on: scaling a company is a rare, amazing, educational experience like no other, and I recommend you stick with it and let yourself grow with the company. However, not everybody wants to, and you certainly don’t have to! If what you love, and are great at, is in fact building the early foundations of a product or company or business model, it’s OK to think about when the point is where you step aside and move on to the next one.

So, if you’re at the beginning — enjoy the heck out of it. It’s often a once-in-a-lifetime experience, and while it’s good to know what may come some day, it’s not worth letting that stress you out too much during the fun parts. If you’re watching the company grow and struggling to figure out where you fit, then this post is for you. I hope you figure it out, feel good, and enjoy it!