You can't fail as a dad

What happens when a founder pivots his core motivations for building

“Bad companies are destroyed by crises. Good companies survive them. Great companies are improved by them.” - Andy Grove

My wife shared this quote with me last week. But this post is not a sob story about how our company was badly run and destroyed by the crises we experienced, nor is it a veiled brag about building a business that overcame hardship.

This post is not even, honestly, about our company.

It’s about my journey as a founder. About how an acute crisis shaped who I am, how I think about life, and the fuel that drives me.

What does a founder do when a crisis forces us to pivot our core motivations?

A founder in crisis

In my last post, I wrote about our GA launch in late 2022. We started monetizing in Q4 and reached $101K in about four months. But by the end of 2023, sales were stagnant; it was clear we had a "nice-to-have" product and were forced into one final pivot.

It was challenging, but it was made even harder by an acute crisis I was experiencing at home.

Just as we began our push to monetize, my daughter Isabella was born seven weeks early. Today, she’s a precocious preschooler, but she spent the first weeks of her life in the NICU. Any parent who’s experienced the NICU knows how hard that place is.

When we brought her home, Izzy weighed less than four pounds, and I could hold her in my forearm. The journey to six and twelve months was long, with many scary moments.

The night before Izzy was discharged, I got a call from my divorced parents. As soon as my father patched in my mom, I knew why they were calling.

“Nick – Zander died.” I fell to the floor in disbelief, crying in pain and regret, grasping my wife’s legs for comfort. My older brother had taken his own life.

Zan was a founder himself, and was both an enigmatic and deeply troubled person. He had struggled with addiction and mental health issues for years.

The coming days, weeks, and months were, to understate it, difficult. Quite frankly, I don’t remember much of Isabella’s first three months of life. But what I do know, and do remember, is that it was the first period where I felt completely and utterly overwhelmed. I suddenly felt incapable of handling everything on my plate and living up to all my commitments — commitments to my family, my team, my customers, and myself.

I felt like I couldn’t do anything well, that I was failing at everything in my life. Failing as a founder and CEO, and failing as a dad.

Getting my mojo back

I’ve always been a high performer, capable of taking on a lot. And, thankfully, I had never experienced mental health challenges despite a long family history of them.

But in the aftermath of my daughter’s birth and my brother’s death, I found myself somewhere new. As a founder, you always feel that the weight of the company (and your world) relies on you, and suddenly, I felt incapable of bearing it.

Thankfully, many people were there to help. My wife somehow managed to care for a premature newborn, her two other children, and a husband who was not wholly present. My best friend John refused to take "no" for an answer and took a bus to New York the day Izzy came home. We had built an amazing team that stepped into the void to push us forward as we successfully monetized; my co-founder Chris was crucial in shouldering much of the company burden that fall. I thankfully already had a therapist. These people and their care mattered immensely.

As I made my way back, I recognized a few important things:

First, I was being really hard on myself. This had always been a helpful trait, giving me fuel, but now it was unhelpful. It was okay to acknowledge my feelings of inadequacy, but I was also being hyperbolic.

Second, I needed to start actively participating in my life and business again. It was necessary to take some time to mourn and for "parental leave," and that was okay. But when I felt ready I just needed to start working again in all areas of my life.

Third, and most importantly, what I now felt mattered, and motivated me had changed. In the wake of my daughter’s trying birth and my brother’s passing, what had always driven my career now felt hollow. Success still deeply mattered to me, but how I defined it and why I cared about it was different.

Pivoting to a new “why” behind it all

I have a specific memory from childhood, of watching Pretty Woman, starring Julia Roberts. To 12-year-old Nick, the movie was memorable not because of its message about two people saving each other, but because I thought the Edward Lewis character, played by Richard Gere, was so freaking cool.

He was a rich buyout executive who rented a luxury hotel penthouse, had a whole staff that worked for him, could buy expensive clothes, splurge on diamond rentals, fly on private jets, and had the power to acquire and dismantle companies.

If I’m being honest, much of what has driven my career has been a desire to be like Edward. I wanted to be a self-made, wealthy entrepreneur who could do those things. I wanted to build a company, have power, succeed, and make money to fulfill the needs of my ego — to prove to myself and others that I was uniquely capable.

But as I found my mojo again, it felt different. One day, while catching up with my friend Brandon, who was incredibly close to both me and my brother, he commented that it seemed I had a joy for life again and asked how I did it. I told him:

After Zan died, I felt like I was failing everyone. I realized that I could survive many types of failure, including the failure of my company. If my company fails, it will be awful and it will hurt — but it’s ultimately just time and money.

But what I cannot survive is failing as a dad.

In the aftermath of the most acute crisis of my life, my "why" pivoted.

My motivator went from fulfilling my ego to taking care of my family. What I did, and who I was as a founder, mattered less as a reflection of me; it became important as a means to care for and be an example to those closest to me.

Was I a better founder?

Through this journey, I felt like I found the best version of myself. It started with my motivation but also influenced new commitments I made to myself, in the form of mantras (in bold below).

I found it easier to balance the stresses of being a founder with the never-ending show that is parenthood. I found myself able to be more present and focused during time with my team and business, and my time elsewhere. I became far more intentional about the sacrifices I made to fit it all in.

I could be this version of myself because I knew that, in the end, I could survive the failure of my company, but not failure as a dad.

But did this better version of myself translate into a better founder?

If we’re being brutally honest, I believe the industry answer would probably be no. A founder-father who always puts his family first, no matter what, doesn’t fit the archetype of the successful CEO.

That archetype tells us to subvert everything to our business. If family relationships suffer, then that’s simply part of the game. What does it matter if Jeff Bezos got divorced? He’s one of the richest and most successful people on the planet — this is just how "badass" founders do it!

All founders will be forced to choose

Why should you care about my journey, my decisions, and whether I became better?

Because as a founder, your motivations matter immensely. They drive what you build, how you behave, and how you navigate the many trade-offs you’ll inevitably face.

While much of who we are is already formed, the experiences of life will continue to shape you and mold your motivations. Crisis experiences, in particular, will play an outsized role, and as a founder, you live in a world defined by crisis.

So be honest with yourself about your motivations and what makes you tick. Be forthright with yourself about what you can allow to fail, and what you cannot.

And be sure that you can live with whatever choice you make; because once your path is trod, it cannot be untrod.