What’s this all about?

First of all, I know that most people won’t care one bit about what I’m working on, so if you’re here reading this, thank you 🎉!

When I was 10 years old (waaaaay back in the late 80s), my Dad and a friend from work quit their jobs and started a company. He was the tech guy, and his partner was a Sales guru. As a kid, most of the details were lost on me (I’m sure it was way more stressful for him than I remember), but I distinctly remember walking out early in the morning to find him asleep on the couch, with his phone on the floor. He had spent all night (again) providing after-hours support for the hotel reservation system his previous employer had built. In other words, he had started by creating a consulting company that answered the phone 24/7 when users of the software he used to work on couldn’t figure something out.

He did this for years, answering support calls at all hours of the night (and charging them for each instance), while he worked on building a new software-based hotel reservation system during the day. I never went hungry or without something I really needed, but I’m pretty sure he and my mom were barely scraping by. I remember the first time I got a pair of actual Nike shoes (because we couldn’t really afford them)… I laid on my bed and stared at them on the floor for an hour before falling asleep.

Even as a kid, I immediately respected the hustle and hard work he put into that company. As it grew more successful and he moved into an office, and then merged with another company, and eventually sold, I would go to the office with him, proud to be the “boss’s son”.

Because of all this, the startup bug really bit me around the age of 12, after seeing my dad’s hard work start to pay off (as I remember it, at least). I remember going to the office with him, and day-dreaming of one day doing the same thing. I remember taking a newspaper into the office bathroom and looking through it, trying to find something I could do, even at age 12.

Some people dream of startups because they want to build an empire or change the world. For me, it was always about being independent.

I’m now in my early 40’s with five kids that depend on me. I’ve tried to make something work since I was 12, and when I look back, it’s no surprise I’ve failed time and time again. The biggest problem has always been execution (meaning, getting people to use and pay for what I’ve built because it’s worth it to them). With each failure, I’ve learned something new. Sometimes, I just never got to the point of launching, because working on a side project during nights and weekends when you’ve got a family can be nearly impossible.

This time, I think it will be different. Why?

  1. I’m taking a different approach to deciding what to build. Instead of trying to hit a home run and build something revolutionary, I’m going to build something in an established market, with existing competitors (more on this in a future blog post, but see this article for context if you’re curious).
  2. I am able to work on this full time, for a year. For the past four years, I’ve been a Software Development Manager at Amazon. I joined when the stock was around $800, so I was very lucky to have been able to ride that stock wave and save up enough to live off of while I pursue this dream. It is insane how much more productive you can be when you are able to dedicate 100% of your time to your project. I would even say it’s 4x as productive as “nights and weekends” because you can work in long, uninterrupted blocks of time.
  3. I have less Product-Market-Fit risk because of the product/category I’m building in. Related to #1, because I’m not trying to hit a home run or invent something totally new, I can stand on the shoulders of the giants that came before me, when it comes to product-market fit and what a minimal-viable product is (minimal-loveable is the bar I’m actually shooting for). I’m not trying to become a billionaire — I just want to live comfortably, support my family, and have the independence I’ve always craved.
  4. I have the experience of dozens of failures. With each failure, I’ve learned what won’t work, which is super valuable. I’ll write more about those learnings as I go.
  5. I have incredibly valuable experience of having worked at the “world’s most customer-centric company” (Amazon), in addition to so many other great companies in my past. This has taught me the empathy, ideal user experience, product/roadmap prioritization understanding, and ability to handle the tech at any scale.
  6. I have a limited runway (one year, or until the money I have set aside from this runs out), and I am determined not to return to “normal office life”, if at all possible. There’s nothing inherently bad about working for someone else or sticking with a normal job, but I’ve craved this since I was so young, and this feels like a once-in-a-lifetime chance.

I wake up every morning feeling so lucky to have this opportunity, and want to share my learnings with whoever might be interested.

Please let me know if you find this interesting in any way — your feedback is like fuel on this fire of mine 🔥

Oh hi there 👋 It’s nice to meet you.

Sign up to receive periodic updates about things I learn that may help you too!

Spam sucks. I promise not to abuse your trust.

If you found this article interesting, please share the love!