“We are not interested in having any stake in this company. We just want exclusive rights to what we have built.”

– Cofounder Frank at our final partners meeting

 

A weakness of mine is believing in the good of person who chooses not to believe in it themself. My first venture has ended because of that reckless tendency.

I shared everything with the company. Nothing was hidden, neither my motives nor my knowledge were kept from the company. But somehow Frank was able to justify withholding information and maintaining ulterior motives for the company as an insurance policy on his equity stake in the company. He wanted leverage against outsiders for when the company started growing up.

Frank scrutinized my every move and measured the minimum amount of commitment that he needed to prove to secure his personal stake in our future. It was easy, I gave out trust like it was an estate sale of girl scout cookies. “Trustworthy until proven otherwise” was one of my principles, and it was only a matter of time before a snake would bite me. My then limited awareness of technology made it a breeze for him to hide under the veil of “complicated details”.

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Collecting my thoughts on what has happened, I want to distill my experiences into a concrete learning opportunity. Walking through the past year should help show the irreparable state that my team was in and shed light on why I persevered for so long past the red flags.

Things started to go bad from the beginning. On signing day, cofounder Larry approached me privately out of guilt with regards to a complicated history with Frank that was unbeknownst to me. My thoughts were “as long as it doesn’t interfere with the operation of the company, I do not see any reason for that to be a problem.” That was Mistake #1 because business was going to challenge every insecure wrinkle buried in our psyches, and if we couldn’t get over our baggage and grow, neither would our company. In retrospect, there is new light shed on the eagerness of Frank to bring on Larry as a cofounder. Business at this stage was extremely personal. I needed a team and I was determined to put one together despite unstable foundations.

The fourth cofounder, Saul, was an emotional train wreck but his skills set was exactly what the company was looking for. Mistake #2 was going to extraordinarily unreasonable lengths to involve Saul in our venture. His personal life at the time was unstable (as it has been for us all at some time), but I overlooked that in order to get our Steve Wozniak.

The stress and anxiety that persisted from working with that team was astronomical. Sure, we had enough qualifications from members on our team to impress any tech investor who happened to read our bios in our pitch deck. But the day Saul called to pull out from the team should have been a wake-up call. But I had a few more mistakes to make before I was ready to wake up myself.

I used the energy of uncertainty at that time to fuel the development of our app by able and willing interns attending our university. That fall semester was thrilling. Our productivity was beyond expectations and it felt as if we had reached transcendence in our work. Despite the red flags of a bad team, I made sure it would not get in the way of building the company’s future. Mistake #3 was to believe that I was going to make it happen even with a founding team that was sandbagging from the get-go. Despite this, I inspired enough of the team to burn fuel until spring with a successful app submission on the iOS Apple store. With no money, very little time outside of being a full-time senior engineering student (not in any computer-related discipline), and a shaky team on which I imposed pizza-bonding dinners on weekends with, I was able to lead an inexperienced and failing team to completion of an extraordinarily complex project. I could have made mistake #4 here, but mistake #3 had drained me down to humility by the end of fall.

I could have walked away in spring when I received an aggressive email from Frank detailing my inadequacies as a CEO. I defended his perspective on the grounds that his anxiety from dealing with a contractor on his own had just temporarily pushed him over the edge. But, again, Mistake #1 was rearing its ugly head again and I was blind to it. That was Mistake #4.

I began to focus on completing my degree and lost faith in my ability to lead these guys. Right before my cofounders took off for San Francisco and Orlando for summer jobs, I was handed a heavy burn of reproach by the both of them. Their bitter aggression made it clear that it was over. But guess what? I was determined to make a broken thing work so I called a partners meeting to discuss how I would single-handedly make up for the stagnant spring on condition that we let go of the past and move forward fresh. Mistake #5 right there.

Funny thing, mistake #5 was necessarily the stupidest but best one to make. The fact that I had no doubt in my mind that I alone could rescue our company on my own, and the fact that my cofounders came to that conclusion as well, meant that I was essential to the company and that they were not. Unfortunately, it took me a long summer to finally learn from mistake #5. After struggling the entire summer in trying to communicate to Frank and Larry on the immense progress that my wife and I were making on a near-daily basis, I was interrupted by a disturbingly aggressive message from Frank. It was an opportunity for me to learn from Mistake #4 . To say that Frank was displeased about me learning from Mistake #4 would be a heinous understatement.

It took me a year to gather the courage to see things for how they actually were and identify exactly where Frank’s interests laid. Our last partners meeting was sour with grudge-oozing resentment and name-calling. By not learning and healing from the mistakes sooner, the wounds festered and rotted the relationships we had until nothing salvageable remained.