Do You Have What it Takes to Finish?

by Joe Wilding, 8/30/23

An old phrase in the startup world says “You have to be dumb enough to start, and smart enough to finish.” I don’t know the origins of this quote, but there is some truth in it. Startups are hard. They require more time and energy than you can even imagine at the outset. If you could foresee the future and assess it in a rational way, you’d walk away before you ever start.

But, thankfully, startup founders often approach a new endeavor with a bit of naïveté. And once started, most founders are committed. Navigating the tricky transition from the fragile start to glorious finish is a slow but necessary process.

I have developed a variation of this idea based on my experiences in the startup world. My version focuses more on the personal side of being a founder: You have to be arrogant enough to start, and self-aware enough to finish.

It takes a unique personality and attitude to be a startup founder, particularly the founder who becomes the CEO. Perhaps the word “arrogant”, with its negative connotations, is too strong. The dictionary defines arrogance as “having or revealing an exaggerated sense of one's own importance or abilities.” I actually think this is relevant. Startup founders have a new idea and a strong conviction to introduce it to the world. Their passion for the concept drives them to do whatever it takes to secure the funding, build the team, overcome the obstacles, and sell it to the world. And the obstacles are often quite large.

Howard Aiken, an early computer pioneer, once said "Don't worry about people stealing your ideas. If your ideas are any good, you'll have to ram them down people's throats." This quote perfectly summarizes the struggle and arrogance it takes to develop a new product in a startup.

While this arrogance is precisely what a startup needs to launch, this same attitude and behavior often becomes its own obstacle in the later stages. Let’s explore an example of how this can play out in a developing company.

In an early-stage startup the team is usually small, often just a few people. By necessity, each person has to wear many hats to accomplish all of the work in the company. A bit of arrogance and flexibility is needed to pull this off. Over time, the team grows and this allows more specialization. This is the time for delegation. Some founders are naturally great at this. Others struggle with it. The “I can do anything” attitude in the beginning is critical for success. But a leader who holds onto that for too long not only is going to suffer from burnout, but is also going to frustrate the team. A wise leader starts to evolve their thinking from “I can figure out the best way to do this” to “this person I hired can do this way better than me, and I’m excited to see the results.”

There are other examples of this as well. Prematurely shipping a product that doesn’t really have market fit is a sign of arrogant thinking. Ignoring regulatory hurdles by wishfully thinking they don’t apply to you can be equally problematic. All of these examples are nuanced. There have been startups that have used each of these ideas to successfully revolutionize an industry. But many others have failed in the judgment of what is possible or lacked the skill needed to overcome the resistance. Self-awareness can help you understand whether you should fight harder for a disruptive idea or if you're being delusional.

The conflicting personality traits of arrogance and self-awareness is one of the biggest contradictions in the startup environment. A startup without some level of arrogance never gets started in the first place. However, too much arrogance in the middle and later stages leads to bad decisions, team dysfunction, and ultimate failure.

So what is the solution to this dilemma? I believe a successful startup founder needs to balance their efforts between company development and their own personal development. Just as companies go through growth cycles and change, a successful founder needs to do the same. Being curious and open-minded becomes a new superpower. What are your strengths and weaknesses? Where are your blind spots and biases? What kind of people and situations trigger you in a negative way? Where are you causing friction or drama in your organization? Reflecting on these questions with honesty can shed light on the successful developmental path.

There are many resources available to help a founder through this growth. A personal coach, mentor, or therapist can have an incredible impact if the founder commits and is engaged in the effort. A peer group of other founders can be helpful if the members meet regularly with honest presence. Some founders can get through this process on their own with the help of books, podcasts, or other reference material. A close friend or partner can also be a great resource when there is a foundation of communication and trust. I know a few successful founders who have embraced several of these resources simultaneously.

Whatever the resource, the common thread is being open-minded in the process, accepting your limitations, and then working hard to level up. Our greatest strengths can turn into our greatest weaknesses. WIth a little effort, you can turn this around. If you are struggling in the middle stages of a startup, you might just lean on the arrogance that got you here to get to the finish line. A good mantra might be ”I am too smart to let my own shortcomings tank this company.” Figure out what it takes to develop the product of “you” and lead the company into the stunning success that you know is possible.