Founder Motivations: The Light and the Shadow

Founder Motivations: The Light and the Shadow

Founders start companies for many reasons. It’s usually a mix of motivations, some motivations are in their awareness, others are not. Some come from a place of possibility, of expansion, even from love. I call them motivations in the light. But founders also have motivations that come from deep needs for security, control and approval, these motivations stem from fear and I call them shadow motivations. Every founder I’ve worked with has some of both, and each of them has an impact on the business they build.

The Soul of Startups — Founder Motivations for Starting Companies


Passion Projects. The first reason I see founders wanting to form a company is passion, legacy or impact. In its healthiest forms, these are founders who are introspective enough to know they have limited amount of time on the earth and they want to create something that impacts the world for good with their talents. Taken too far, it can seep into narcissism and unhealthy ego-driven behaviors, but founders who can keep the dark side in check have the drive to leave a mark on the world in positive ways.

An example: I’ll never forget meeting the founders of what would become Wunder Capital. The way they talked about starting their business left my chin on the floor, and I’ve never seen something started so much deliberate impact since. They came up with the idea to create funds to provide capital to commercial solar projects, a desperately needed solution to help more commercial solar power projects get funded. They said, “We were only interested in working on ideas that would leave a dent in the world, and for us, that was one of three things- education, health, or energy. We kept developing ideas in those three areas and dismissing ones that we didn’t think would work until we found this one.” I was struck by the intentionally of the process of settling on the idea they would eventually turn into a company.

It’s not always like that. It’s more typical that the “dent in the world” that a founder or founders wants to leave comes from a problem they have lived. That problem got under their skin, irritated them over months or years until they said, “I have to go solve this problem, I know there is a better way.” These founders are great at understanding the problem and empathizing with their customers because they’ve lived the problem, but they can also be really attached to HOW the problem is solved. They know what would have worked for them when they had the problem, and they assume, sometimes rightly and sometimes wrongly, that the same solution will work for others facing the same challenge. If they are open-minded, I love working with them. If they are stuck on their solution as THE solution without a willingness to talk to a lot of customers, then they can be the most stubborn and frustrating founders to work with. When it comes to having an impact, doing what’s right can easily slip into feeling righteous, and righteousness isn’t very adaptable or flexible, which is key to learning in the early days of a startup.

Particular People. The second reason I see founders coming together is because they want to create a company with THESE specific people. It’s usually some version of friends from childhood or roommates from college, skydiving buddies (true story), colleagues that worked closely together for years, or even siblings or cousins that are close. Whatever the scenario is, it’s based on a deep trusting relationship. Cofounders want to take an adventure together, almost like a road trip mentality, they know there will be ups and downs, but these chosen cofounders are the ones they want to journey with. They may have talked about starting a business together many times before they actually pull the trigger and start something, or maybe they’ve done some side projects together in the past, but this is the “real” one.

There are so many examples in my head it’s difficult to choose. The story of Everlater comes to mind. The founders are childhood friends who were on a globe-trotting trip as young people often do when they started talking seriously about starting a business together. They considered buying a hostel in Panama but settled on a software tool to help travelers blog and share memories from their trips. They had little money set aside to start something and neither of them knew how to write software. When they returned home, moved back in with their parents, learned to code, and incubated the idea including getting accepted at Techstars. There were rough days before an eventual exit, but the idea of leaving the other would have been difficult. They were committed to each other for the good times and the bad times. They continued working together for a number of years at the acquiring company and are still close friends. I wouldn’t be surprised to see them start another business together in the future.

For the Challenge. The third reason I see founders start companies is because they like the challenge of it. Some people just like to climb big hills, it makes them feel alive. To do work that is easy is unthinkable, they need to feel stretched to feel alive. These founders have a deep sense of accomplishment and achievement. They are often successful athletes or top performers on a team, a club or a sport. They could be the state champion speech and debaters, the scholarship winners or the decorated athlete. In whatever they did, they achieved a truly impressive level doing it. That pattern of meeting challenges with hard work, persistence and eventual success led them to look for bigger challenges, and they found the idea of starting a company, the proverbial blank page challenge, one they wanted to overcome.

I learned this lesson when I met Devon Tivona who went on to cofound Pana. I watched a fresh college grad, all of 21, deliver a lights out pitch in a crowd of 300+ people, and in spite of the fact that I hated the business, I couldn’t help but be a fan of the performer. While he was a part of Techstars, I watched as he and his cofounder built and tested products faster, pitched better and rallied people around them more than older entrepreneurs with far more experience. He was the first of many entrepreneurs I’ve worked with that were hard to keep down, no matter what happened, they seemed to find a way through it, stronger than before. They have grit that comes from thousands of disciplined hours spent getting better at something. They know what it takes to delay gratification for a bigger payout down the road. These founders can have a shadow side, a need to be seen and recognized externally that can drive them to unhealthy places to get that attention, but at their best, they rise to the occasion and inspire the people around them with their work ethic, focus, and results. At their best, they are magnanimous leaders capable of building great things.

Freedom To. Some founders had ideas that are big and bold and don’t fit well in the institutions from which the idea was born. These founders get frustrated by limits placed on their capacity and the potential of the idea. They need to start their own company to fully express either themselves or the solution or both. They have a profound belief in their ability to create something in the world that not many if anyone else can see or believe can exist.

My favorite story comes from Vanessa Clark at what is now Atomos Space. She was working with a European space agency charged with a research project on how to move satellites more efficiently. When her research led to a proposal to build a nuclear powered satellite tugboat in space, the organization she worked for didn’t move the project forward. She felt it was such a good and worthy idea that she left the agency and started her own company to make the solution to reality.

Shadow Motivations:

Building your own company is so hard that I find it hard to believe that anyone without some shadow would choose to leave working for someone else. Holistically, it’s far easier to be an employee than an entrepreneur. As someone said recently, entrepreneurs are the kind of people that would rather work 80 hours for themselves than 40 hours for someone else. Ever wonder where a founder’s drive comes from? Maybe they are “just built that way”, but more likely, there are motivations lurking in the shadows.

The Fight for Approval or Worthiness. It’s the most common shadow I see in founders, and it is very often not in their awareness. This founder is motivated by their need to win approval, and the approval they are most often seeking, whether they know it or not, is often a parent. They will work themselves to the bone in the hopes that the success they obtain will finally get them the “I’m proud of you” they are craving. While some parents expressed outright disappointment in their children, I think it’s more common that parents are proud of their children but stumble when it actually comes to expressing it to them. Those children, if they grow up to be founders, can be motivated to build the mountain of evidence of their success higher and higher believing that one day, it will amount to enough to win their parent’s love and approval. Those thoughts are hungry ghosts, never satisfied.

Spite. Some founders are motivated by a deep desire to prove someone else wrong. Someone told them they would never amount to anything or that they’d never succeed at X or that they were a failure or that the idea would never work. Those founders turn that desire to prove someone wrong into seemingly boundless energy. It’s motivation full of spite and resentment, and while I’ve seen it fill the energy well of founders, but it eats at the soul if founders don’t pay attention to check it. Unchecked, founders want to win at all costs because winning is a part of the identity they need to project in order to feel ok about themselves. To fail in the business means the story that they are a failure must be true, and the shame loaded into that potential reality will keep them going long past when it makes sense to quit and it will justify the most heartless decisions or a sacrifice of other deeply held values.

Never Again. These are invariably founders that grew up with an unstable supply of resources like money, housing, food or other basic necessities. They learned how to make money at a young age, and they often made money to support themselves and/or their families. Not having much money left deep impressions on these entrepreneurs, and once they learned how to make money for themselves, they never looked back. These are the underdogs, we love (at least in this country) rooting for them and championing their stories, though unless we get into depth on someone’s founder story, we may never know what humble beginnings really spawned the drive that created that startup success. This shadow also deserves careful monitoring as it can inhibit taking worthwhile risks or it can drive an unhealthy sense of never having enough long past having made enough money to have of everything for their entire lives.

Freedom from: These are the founders who don’t like being told what to do. Sometimes they say things like I don’t work well in groups. Almost all founders I’ve met have some version of not liking the rules or having a disinterest in process, and while that’s one version of the shadow, some founder is genuinely can’t collaborate or take the input of the group. Either they need to be their authority on everything (so they can keep control), or they just don’t think the rules apply to them. Sometimes it shows up as, “do as I say not as I do” or “because it’s my company” is the rationale for a decision. Talented people tend to leave leaders who behave this way because they can’t have the impact that they want with their skills when they can’t influence the decisions being made. Every founder has things they care deeply about that they’re not flexible about, and those are helpful for defining culture, but the shadow shows up for founders who have an inability to let go and delegate or they create dysfunction by refusing to model the behavior the company needs from everyone to be successful.

Another way to think about these shadowy motivations is that they are at the heart of three of our most basic needs, in fact any need can be broken into these three: The Need for Security, The Need for Control, and the Need for Approval. These needs are possible to source FROM WITHIN rather than from external sources, but that’s WORK. A lot of challenging, vulnerable, inner work.

If you are a founder, does one of these shadows resonate with you? What does it look and feel like when you are leading from a place that isn’t motivated by those stories? What does it look and feel like for you to lead from a place of love, creativity and possibility rather than a place of fear, anger or sadness?

Startups are either a powerful platform for personal growth or an incredible playground for dysfunction. If you are a founder who wants to build a business with a great culture, it traces back to the soul of the founder. You are called on to do the work of knowing the deepest and potentially darkest reasons you are on this journey or risk building a shadowy temple to a wound you haven’t healed.

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