Tough Conversations: Founder Relationships

Relationships between startup founders are among the most complex you will experience in life. For a startup to be successful, the foundation established by the early founder dynamic must be capable of withstanding immense pressure.

When I speak to entrepreneurs about their founder relationships and consider my own experience, I find that the subject matter of tough conversations is often similar, but the magnitude of difficulty is driven largely by when they happen. I recommend founders have tough conversations at the earliest stages of their startup. The process helps bond the founding team and ensures that when challenges do arise, ground work has already been laid for the business to make the best possible decisions. At the crux of most difficult founder conversations is the question of identity.

Founder Identity vs. Role Identity

When you work on a startup for many years, your status as a founder becomes core to your identity. The word founder evokes characteristics like leadership, ambition, independence, creativity, and success. Founder status is a major part of who we are and it will stick with us even after our startup finishes its independent journey, regardless of outcome. Even though I’m now a venture capitalist, I still think of myself as a founder and an entrepreneur — it is core to who I am.

A key challenge arises when we conflate Founder Identity with Role Identity (and title). A common scenario is when a startup outgrows a founder’s experience level in a particular role and seeks to hire above them. For the organization, that’s a great thing because it means that the business is growing. And even though the idea of doing whatever it takes to help your startup succeed is intuitive to a founder, this particular case can trigger feelings of betrayal, failure, inadequacy, and frustration. This happens when we’ve conflated our Founder Identity with Role Identity.

No matter how your title or the nature of your work changes over time, you will always be a founder.

At Looksharp, where I was both Founder and CEO, we decided to hire a head of marketing over my co-founder, Nathan Parcells, who wrote eloquently about the experience afterwards. Nathan had crushed marketing in the early years of the company under the CMO title by building organic channels (among other things) that acquired millions of users over time. The company was evolving, however, and I felt that we needed somebody with more years of experience to run marketing, in particular on the B2B side. We hadn’t had this particular conversation at the beginning and it ultimately cost us both a great deal of emotional pain and became a distraction to the organization. Honestly, I was terrified to even broach the subject because we had both fused our Founder Identity with our Role Identity over the course of several years building the company. The whole process became a huge source of anxiety for both of us.

Nathan and I have known each other since elementary school and I’m not sure our relationship would have survived this chapter if the foundation of friendship and mutual respect hadn’t been so strong. If we had simply talked about those potential eventualities when we first started Looksharp, we could have saved ourselves a lot of angst.

Founder Identity vs. CEO Identity

During a period of sustained difficulty at Looksharp I called a board member and asked him if we should consider hiring another CEO. He said no, but in broaching the subject I was acting as a founder whose obligation was to consider any possible way of helping the company, even if it meant removing myself from the top job. CEOs tend to scale more easily than founders in other roles because the job doesn’t require domain specialization in the same way. The CEO has the benefit of being able to surround themselves with more experienced executives. That strategy breaks down pretty quickly, however, if members of your executive team are equally inexperienced.

In either case, when an organization decides to recruit somebody with more experience to manage a founder’s domain, it’s actually a huge opportunity to help the company leap forward and accelerate your professional learning curve. You get to either level up your game by learning from the best or think about contributing to a totally different part of the organization that interests you. If you think about it, flexibility in your role aligns perfectly with the founder’s obligation to contribute in the greatest way possible to the overall success of the company.

If you haven’t had the tough conversation about this eventual likelihood during the earliest days, it will happen at an emotionally charged time when founders feel the most vulnerable and the risk of damage to both your startup and your founder relationship is significant. As with most tough conversations, the earlier you steer into the challenge, the better the outcome.