Rebel Founders: Undermining Your Own Success

There is a certain rebellious streak involved with becoming a founder. You go your own way. Lots of founders start their own companies because they don’t fit well working for someone else or because the person they were working for doesn’t like the idea did they believe in. Author Gretchen Rubin uses a Four Tendencies framework to describe rebels: they don’t particularly like upholding the expectations of others or of themselves. Rubin points to appealing to a founder’s sense of identity when compelling the rebel to do something that is in his or her own best interest. I see this with the rebel founders I work with.

Image by Andrew Martin

In the beginning, when the company is small, founders can be rebellious about everything. They choose Macs over PCs. They refuse to capture receipts. They create logos with ostentatious colors. They create innovative clauses in there term sheets. All of these are real examples from companies they didn’t want to do things the way they were done at the places they’d worked. I get it. I even applaud it. The problem comes when it gets in the way of creating the minimum viable structure needed for a company not to be in chaos. It isn’t very long into a company’s life before it requires some discipline. Author Jim Collins uses phrases like disciplined thought and disciplined action in the context of disciplined culture to describe how the best companies proceed with doing their work:

“Disciplined people who engage in disciplined thought and disciplined action, operating with freedom within a framework of responsibilities, this is the cornerstone of a culture that creates greatness. In a culture of discipline, people do not have jobs; they have responsibilities.”

That word disciplined is not accidental, not a throw away. A company without minimum viable process quickly lapses in the chaos and spends its energy and resources unwisely. Companies in this place find it hard to answer questions like,

  • “How do you know what everyone is working on?”

Answers to those questions require coordination, planning and communication. They are best answered on a regular cadence, regardless of the size of the team, and if your team is remote, answers are better when they are fully documented. Even in-person, a modicum of structure and predictability leads to better outcomes.

The CEO I last talked to about this issue was struggling with a discipline capturing all the things they were working on in a workboard like Trello or Asana. It felt laborious or tedious to do the work of documenting everything that needs to get done, the excuse was it’s time spent away from actually doing the work. Many founders reject disciplined process up front in favor of spending time doing more of the work, more time executing. What they don’t see is the value of spending the time up front to plan. It reduces waste, which comes in many forms. Waste can be doing work over again, called rework. Waste can be two people doing the same task. Waste can be two people working on the same thing but not in a way that’s coordinated. Waste leads to misunderstandings, finger-pointing, frustration, and hurt feelings. Spending the time upfront to avoid that is worthwhile if it’s in proportion to the amount of time to work will take. I share with founders a rule of thumb: 90% of their time should be spent doing the work, the other 10% of the time is spent improving how you do your work. That could be planning, learning, coordinating, integrating or anything else that makes the totality of the rest of the work better. It’s similar to another rule of thumb for engineering teams- for every nine engineers you hire, hire a tenth to make the other nine better.

Image by Melk Hagelslag

Think about the whole company this way. What would happen if for every nine salespeople hired, a tenth sales person is onboarded to make everyone else better? Have you worked in a company that hired that way? But logically, if 10% of the team’s energy is focused on making the other 90% better, those improvements in productivity compound over time and create an incredible multiplying effect on the output of the team in total. That is why discipline is so important. It’s not just about focus, which is important for startups, it’s also powered by the impact of many small improvements over time. They add up. It avoids waste at a time in a company’s life when I startup cannot afford waste.

If you are a leader and agree with the idea of discipline and its importance, yet you’re still struggling with the practice of actually doing it, I offer some reflections and questions to ponder:

  • Do you want to be the kind of leader that enables others?

These are questions that go to the identity of who you are as a leader, and if Rubin is right, it’s the best way to motivate that rebellious founder part of you to have just enough discipline.

Explorer of the Soul of Startups and lean vulnerability, outdoorswoman, dog mom, coach, facilitator, operator, truth-teller, sometimes investor.

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