It is my son’s first birthday today — and I wanted to reflect on what year of parenthood and what I have learned as it pertains to my career.
Happy birthday Cain!
Dear Cain,
Today is your first birthday — which means it also concludes my first year as a parent. The year seems to have passed at the speed of light, just like your early arrival. You arrived quickly and you had to learn quickly too as the NICU is no celebratory place. I vividly remember the day before you came:
I had an introductory sales discovery call with the chief of staff of a 4,000-person mortgage originator.
I also had lunch at Gotts with a group of founders who were researching my market for startups (they recently announced the release and that they are in YC’s W2023 batch)
I conducted an interview with a candidate.
It was a normal day. I thought you were five weeks away, and I believed I had time. I had even planned a last-minute trip down to LA for the weekend ahead. Around midnight that night, your mom complained of pain, which prevented her from sleeping. As a result, I also could not sleep. Finally, at 6:00 that morning, we decided to call her OBGYN (delivery doctor) and inform her about what was happening. She told us to go to the hospital. I had not packed my bags yet, but I had a feeling this thing was happening.
When I reflect on how fast things can change it’s not unlike running a startup. Things are unpredictable and they can change overnight. Last year I read a book that I’ll give you a day called Four Thousand Weeks. Four thousand weeks is the average amount of time we have on earth. I want to unpack a bit about what I have learned in the past year being your dad as we celebrate today at the Zoo and later tonight at Che Fico.
Most of the cliché stories you will hear about how hard parenthood is are true.
Parenting is exactly as difficult as anyone who is a parent tells you. The difficulty might even be understated a bit. No one is giving out annual awards to great parents, and I know it may sound like I am complaining but the early days of being your dad were grueling. We spent hours at the hospital for the first few weeks and while we learned the basics from great NICU nurses. After we brought you home, we quickly fell into the treacherous sleep cycle you caused because, well, you are a baby and you could care less about sleep cycles. In our case, this lasted for nine months and you still wake up from time to time as you go through teething and sleep regressions. In addition to sleep issues that began when we brought you home, there are other factors to consider, including the tension it causes with me and your mom. It is never easy to wake up at 2 AM, feed you and nurse you back to sleep after you’ve been crying for an hour. This, while difficult, is the tip of the iceberg. When I became your dad, my biggest asset – time – was essentially cut in half.
Let’s unpack the three important lessons I learned in my first year being your dad as it relates to my career (my founder journey), you, and your mom. I will conclude with my framework on managing all three and the most important task of all — taking care of myself.
My career does not elicit sympathy from the world simply because I am your dad.
I should have been more urgent with business matters leading up to your arrival. As I mentioned earlier, I was in the process of closing some major deals, in the startup world every deal is major, when you unexpectedly arrived five weeks early. In March 2022, the fundraising market was still mildly hot, and I could have closed a round had I been more diligent. I mistimed the market, and by the time I returned from a brief paternity leave, the market was struggling. Fundraising became close to impossible without exceptional metrics. This causes stress and is why time management is so critical.
Don't expect leniency from the outside world when it comes to new responsibilities. I remember sending out an investor update after you were born — I think two investors actually sent me a direct response congratulating me on becoming a father (I even included a picture of us in the update). It is not their fault, the year you were born was one of the worst years ever for venture investing. As you grow up, remember that results are key and markets, just like life, can change drastically. I will always love you, but the world, markets, and people will only love you as long as you are performing. To avoid disappointment, or worse, feeling like a victim of your circumstances, it is important to understand this. I have learned to approach my career with a different mindset now that I am your dad. The results of my work are not just for the shareholders, but also for both of us. If I succeed, you will benefit, but if I am not successful, you will also be negatively affected. However, my chosen career path does not define my worth. True love is unconditional, whether I succeed or fail. I am still your dad, and that is my most important job now.
Optimize your schedule as if you had 2-3 fewer "work" hours per day. Time management is maybe the most important thing I have learned being your dad. Days mostly feel like a race against time. As I write this, I am lucky that you are taking a longer nap than usual. While it is beautiful, I know that when you wake up, you will have needs, so I have to be efficient. The next time around I will be more ruthless with my time and sometimes that means having hard conversations with my colleagues, your mom, and our family — it just has to be that way if expect to get anything done and be able to spend valuable time with you. This is what I want to instill in you over the years.
You do not care about my career right now and that is ok.
I have accepted that there is no way to fully prepare to be your dad. I have written about this previously but there is no amount of books, advice, or money that can fully prepare me. That does not mean I should not read books, talk to people, and build deep relationships with other fathers but much like my career, it has been a lonely journey in this first year. I've had to get used to learning about new things almost every week, and learning on the job is essential. Before you were born, I had never changed a diaper, held a baby for more than five minutes, or watched a kid. I had no experience with infants or any deeply intimate interactions with them. While I am no expert, you are still alive and well.
Try to create a buffer that allows you to take at least two months of paternity leave. We are fortunate that your mom works for a mature, publicly-traded company that offers generous family leave. Despite the drastic changes that big tech is currently undergoing, the benefits overall are great. My job has benefits as well, but since my company is small, there is too much work to do to take a significant amount of time off in your first year. Dad is in the trenches. However, as the CEO, it is my responsibility to set the standard, plan for it, and take time away from work in the first few months — I learned that the hard way.
Sleep training early and consistently can help establish good sleep habits for your baby. If possible, consider hiring a night nurse to assist with the process. The biggest flex for me and your mom would have been having a night nurse for those first few weeks when you came home — I had heard stories of billionaires spending as much as $10,000 a week for a night nurse — and I see the value even at that price. For mommy and daddy, this is an unreasonable expectation. However, during the first few months, there were times when I would have paid anything to be able to get just five hours of sleep — you have no concept of time at your age and you needed to be fed every three hours around the clock. One of the most challenging things we had to do in this first year was sleep-train you — we had to let you cry for 30 minutes straight at times. Although it was difficult and may seem ruthless, it was a necessary step.
Your mom needed me to be present to support her during pregnancy and after childbirth.
Being a career-oriented adult can conflict with marriage. Besides me and your mom welcoming you into the world, we are not even two years into marriage. One of the more challenging aspects of being a new parent is managing the highs and lows of pregnancy and postpartum. To quote Jeff Bezos, “I wanted a woman who could get me out of a Third World prison. Life's too short to hang out with people who aren't resourceful.” That is your mom. The last year has been quite a strain on us financially because your dad did not prepare, and having high career aspirations often comes with certain risks that are essential to have a mom like yours who understands and who has a reliable income herself — we are blessed with both, but that does not mean there are no conflicts where communication and transparency are essential.
It's never a bad idea to over-communicate your plans and ambitions. Communication is crucial in any relationship, particularly when you became our pride and joy. We now use shared family calendars to track work commitments, leisure activities, and other events like doctor appointments. Managing finances has become even more critical — your nanny accounts for a high percentage of our monthly expenses now, and we have to organize a time to spend together with just mommy and me. As you grow up and turn into a man one day you will recognize that women often face additional challenges with parenting and to adapt accordingly.
The journey of becoming your dad and your mom’s husband in roughly a year was a lot. Adding two major responsibilities to running a high growth startup can be overwhelming. Your dad has a job that can be difficult like any one’s career, depending on the boom-bust cycle of technology startups. To succeed, you must mature quickly, manage your time ruthlessly, and understand that performance is essential in all aspects of life.
The three things I have confirmed in the last year of being your dad:
The career path you choose may not elicit sympathy when life happens — stay the course and know that.
You do not care about your dad’s startup journey or sleep for that matter at least for the first year
Your mom requires my presence to support her through pregnancy and postpartum.
My takeaways are:
The holy trinity of extreme career ambitions, being your dad, and being present, loving, and caring for your significant other to your mom is a lifelong journey.
The most important task is to take care of myself so that I can take care of you.
Happy 1st birthday
Love,
Dadda