Founder and Father October 2021

Being a Dad and starting a company at the same time is hard. I wrote a version of this essay, and then deleted it, because it wasn’t honest. It was aspirational and measured. My experience as a founder and father have been neither. They have been brutally mundane, extremely uncomfortable, and often directly conflicting in their needs. This is my reflection.

I decided when I was in high school that in my adult life I had two missions in which I could not fail: be a founder, and be a father. It took me another decade to build the necessary relationships, experience and resources to start to do both. In the end, I started Convictional with Chris in the same month as Jess and I found out she was pregnant with Magnus. I am so glad that they are my partners in this process of becoming what I set out to become.

In the time since then, I have learned so many things about how right and wrong I was in my original, dual minded pursuit of meaning. I have brought happiness into my life, and a lot more unhappiness than I was expecting too. I don’t think I appreciated fully at the time how much richness comes from the pursuit of difficult things with people you care about. I don’t think I appreciated how difficult it can be to pursue those things either, by themselves or together.

I remember being so excited to close our first few customers at Convictional. Starting a B2B company, customers are oxygen, and it took six months. It was deeply gratifying having to send our first invoice and collect our first payment. I remember being crushed when one of those customers fired us because I was away from the support inbox to support Jess and our newborn son when both were in intensive care at the same time after our first arrived early. It was when I realized that I am one person, and two missions can be and often are compromising. I described it in therapy as being torn in half, and I still feel that way sometimes.

Each hour of my life I am choosing between the investments I can make in my family life and the ones I can make in my work life. In my soul I love work, but I would gladly perform the construction work I briefly did as a teenager for the rest of my life if it meant the health of my kids. It can be exhausting choosing between them at each moment. In many cases, the unhappiness exists in the present, while the happiness associated with the process is deferred to the future. I am optimistic about the gratifying feeling I will experience when it comes together, and further I feel a deep sense of meaning at all times now because of these obligations.

I remember moving to California for three months, with a six month old, to fundraise for the company. Opportunities were afforded that I would not have otherwise been able to have if not for the partnership of Chris in the company and the partnership of Jess in our marriage. I focused exclusively on doing things that would progress the business or sustain the family, in lieu of fun, feelings and friendships. The people around me would enjoy deepening their relationships. I would go home and hold my sick child upright in the bathroom at night while the shower ran to clear their snotty nose. I did this so that they could breathe well enough to sleep after catching exotic illnesses from being in a new place with new people so that I could be fundraising. I remember being intensely jealous, guilty and tired in those moments.

Taking on the role of company founder, you end up with a job that can often amount to ‘only the things the competent team around you cannot solve, or that are so poorly defined no one else can stomach’. As a parent, it is similar, only you do not get paid to do it. In that sense, parenting is harder, there is plenty of validation in all things starting a company at this point. Parenting seems both mundane and shocking in it’s hardship. No one writes about you for breastfeeding thirty times a day like Jess did for our first baby. So no matter how hard what I experienced in the business felt, it felt like I had an easier job in those periods relative to Jess. That can make it very hard to talk about what you’re experiencing, the person who has it worse that you compare yourself to also happens to be your chosen partner in that same work.

When I hear people complain about getting Slack messages at night or some other form of modern work grievance, I find myself comparing their experience to the experience I had when both mom and baby were in the ICU. It makes me feel like I’m immune to burnout from work. Nothing I experience can be as hard as that was, and I don’t think anything including the end of the company would be either. My metric for success was that ‘both of them end the day with heart beats’. My strategy was to do all the things in my (limited) power to make that happen.

Once you have had an experience where you have to think in those terms, no amount of email, difficult customers or material setbacks can daunt you. Speaking in a room full of investors just doesn’t even register on the stress scale. I am immune to the distractions of startup status seeking politics. I am comfortable letting my imperfections show. I am content to give the legos away to people better suited than I am to pick them up and make them into something great.

Being a parent is the hardest thing I have ever done. Being a founder has been an enjoyable occupation, on the scale of consistently the second most meaningful, second most important thing I have done with my life to date. I am motivated by the notion that my work now can make life better for other people’s children. And I’m motivated by the notion that the resources my work leads to can benefit my own kids, primarily through learning and personal development.

I want to give my kids the learning experiences that I had, to be able to become myself. But I recognize that I cannot protect them either from harm, to themselves or even worse to the families they may choose to go on to create. The pinnacle of skin in the game is to accept that the world has flaws, and to introduce life into it in spite of those flaws, and to believe (and work towards) making that world better for those people. It can heal as well as hurt, and it ultimately can be a uniting force to make it possible to see the common humanity in all people.

If you’re on the fence about becoming a parent, I would not recommend becoming a parent. If you’re on the fence about starting a company, I’d recommend joining Convictional, or Google, or anywhere you admire where you think you can learn things that are meaningful. If you feel like I did though, that it’s a cannot fail mission, then I would get started now. These are not things to undertake unless you are sure that the meaning is worth more to you than happiness is.

If that sounds dramatic, wait until you meet toddlers and customers.