Matthew Duff Learning, writing, and building in the open

January 30 2022 Weekly Reflection - Exploring my curiosity, incorporated business, and an almost usable SwiftUI app

Entrepreneurial pursuits early in my career

My first job was at MX after graduating from a coding bootcamp. I was there from 2012-2015. I started a small website for a paying customer while I was there. It was very fun. I was a horrible programmer and I got to code on this side project with two friends/coworkers. We added a lot of value to our customer and I learned a lot while doing it. We were incredibly entrepreneurial and after moving on from the previously mentioned website we had shiny object syndrome and kept doing false starts on a lot of businesses.

Ten years later we all work at different places, but we all still meet at 7am on Sunday morning to discuss our entrepreneurial pursuits (and life). We have all had incredible growth in our full-time employment and career growing. But we have not moved the needle, at all, on entrepreneurial pursuits. This was becoming a large source of shame in my life. It caused me significant stress to want to be entrepreneurial but to continually fail at getting started. My full-time employment takes most of my mental reserves and when I finished a day of work I had little motivation to go start a business. The financial lure of starting a business had faded as well. With GitHub’s acquisition in 2018 I have largely checked off the financial checkbox. I have enough of a nest egg now that I don’t need to actively save for retirement (but I still do!). My current comfortable financial life, and the lack of mental reserves after a day’s work in my full-time employment, left me feeling like I couldn’t make progress.

Between leaving GitHub at the end of December and joining LaunchDarkly a few weeks later (highly recommend taking a few weeks off between if you can!) I thought a lot about what I wanted to do. I realized that I spent hours per day scrolling on my phone. The marginal utility I get from the first half hour of checking social media messages and seeing what is happening with friends and family is decent. But the third hour of doing that has almost negative marginal utility. I tried to capture the different between creating something and the tiny dopamine hits of scrolling here

Scrolling vs creating

Exploring my curiosity: No more pressure to start a business

I decided I would stop scrolling, and stop trying to make a business, and just pursue my curiosity. I enjoy building things. I like figuring out interfaces and gaining a new skill. I had a ton of ideas that I wanted to explore out of curiosity without the need for them to become a full-fledged business. I decided I would build an app, learn SwiftUI and Swift better, and explore my curiosity around challenging myself to be more deliberate with my time and attention. I have been building for about a month and it’s been going well. I’ve made progress. I have been programming for about an hour per day starting at about 6:30am. Just in that small amount of time I have made decent progress. Working in the morning helps because I haven’t used up my mental reserves for focus at that point. I am enjoying learning and building. It has made building fun again, instead of so much pressure to start a side hustle.

If you are struggling in a similar way to how I’ve been struggling with the pressure to start a side hustle, I recommend making the focus on exploring your curiosity and not creating a side hustle. The change in just the mental model of how I am thinking of it was really helpful for me. It freed me to do something for fun instead of having to second guess myself on if this idea was the most lucrative or most likely to succeed. I am doing now for the enjoyment of building. Maybe something comes out of it?

Progress I made this week:

  • PeakStreak: No longer doing I wanted to explore challenging myself to live more deliberately. This is the app I’ve been exploring my curiosity with. Progress I’ve made this past week:
    • Incorporated a company 😬: I am getting close to sharing my app with friends and family. I wanted to upload it to the App Store and decided to incorporate the business. I did this through Stripe Atlas and it was a pleasant experience. Now that I have a Tax ID number I will set up my developer account to distribute it. I know this is different than my “don’t put pressure on yourself to start a business” statement from before. But this feels organic and not forced. I am doing this to keep things clean with the Apple App Store as well.
    • List challenges: I made the page to list all challenges. The design is meh, but the functionality works.
    • Create activities against challenges: I am almost done this. Just need to associate the activity with the challenge which should just be a few lines of code and then I’ll be able to use this to track my activity against the challenges I’ve set for myself.
  • Airbnb initiative:
    • Finding land: Kylee (my wife) is looking for properties for us to buy in the mountains of Colorado. We are going to build some yurts and have camping spots on the lot. I have set aside about $100,000 for the purchase of the land and about $75,000 for the building of some camp sites and a yurt or two. We are excited about this. She is going to be point person on this project. She does not work outside of our home (we have four kids!) and she has some capacity to move this forward. Hopefully buying land in the next month or two. If I make enough money from this to pay for my mortgage I’ll consider that a huge win. We considered paying off our house, but figured if we could just spend $175,000 of that money and make enough to cover the mortgage with Airbnbs, why wouldn’t we do that instead? Our home was appraised at $980,000 and we owe about $540,000 with a ~$2,700/month mortgage. We should be able to cover the $2,700/month with these Airbnbs, especially if we have no debt with them. I’ll update you all and let you know how it’s going as we make progress.
  • Fitness:
    • The app that I am making is an attempt to help me with this. It will incentivize me to complete the challenges I’ve created for myself.
    • Other than that, I’ve lifted weights about two times per week for the past couple of weeks. I want lifting to be four times a week (strength really increases quality of life and longevity). I’ve been going on walks with the dogs and such.

Goals for next week:

  • PeakStreak:
    • Finish activity tracking
    • Fix unresponsive touch when dismissing a DetailView in SwiftUI. I think I know how to do it, but need to try a couple approaches
    • Enable image uploads in activity tracking
    • Issue stock in C-Corp (part of incorporation)
  • Airbnb initiative:
    • Get together a list of properties to purchase
  • Fitness:
    • Lift weights four times this week

Thanks for joining. I am trying to just write and not worry much about editing and such. I often don’t write anything because I am afraid of writing something bad. I need to just get it out and worry less. If you’d like to see any specific improvements, don’t hesitate to reach out.

Starting weekly reflection posts about entrepreneurial journey

Early career and struggling to find time

Ten years ago I attended a coding bootcamp. I was part of the first cohort of the first ever coding bootcamp. I joined this coding bootcamp to build an entrepreneurial idea I had been working on with a friend. After attending the bootcamp I wasn’t skilled enough to build the business I was intending to work on. I joined MX to improve my skills. I was a terrible engineer when I joined. I didn’t know enough to thrive in the role I found myself in. To overcome this skill gap me and another coworker at MX started building a side hustle site where I could practice my skills and provide value to someone else. This was fun, rewarding, and I learned a ton.

Three years after joining MX I ended up moving to GitHub to help build out their Professional Services organization. It was the opportunity of a lifetime for me. I loved the people, the company, and the role. However, it was a very demanding role and my entrepreneurial efforts were put on hold. At GitHub I was making enough money where it made sense to give it all of my professional focus, leaving little time for any work on the side. This was the dyanmic for about five years at GitHub, but the entrepreneurial ideas were always coming up.

Now is a great time to build

Things have changed. I led GitHub’s Professional Services Delivery organization for a few years, building it to around 50 team members and many different teams. I loved this work, but it was taking a toll on me. Each year the team about doubled, and with it new stresses and weight gain! I realized I needed to make some changes. The financial box had largely been checked off for my family as a result of GitHub’s acquisition by Microsoft. My oldest child is in high school now and I realized that while trying to accomplish things in my career I was going to miss some of our best years together if I didn’t stop and take stock on my goals in life. I want to be a more present father who isn’t stressed as often.

About 1.5 years ago I asked to be moved to a new role at GitHub that is more sustainable in terms of demands. After a bit more stress being responsible for two teams I have landed up in a healthy place. I feel less stress in my current role and believe I can provide great value to the company during normal working hours. I’ve been inspired to dust off my entrepreneurial efforts now and focus on two things primarily:

  1. Building a small scale software company slowly through dedicated effort over years
  2. Building a few Airbnbs for vacation rentals to provide for most of my money needs and create experiences for others

I will be updating this blog each week, taking stock of my goals and of my physical fitness. These three things, overall, should increase my quality of life, scratch my itch for self-improvement, and help me accomplish some of my remaining financial goals.

A few things to note:

  • I am terrible at shipping when I don’t feel the product is perfect. This has been a large hurdle in me moving forward any goal. These blog posts are a way for me to overcome this fear, including the writing of this post itself!
  • I want to enable others to follow along. I have a group of friends that meet up weekly on Sunday mornings to discuss life and encourage each other. I want this blog to create community in a similar way. I have loved reading the updates from Michael Lynch and Jen from Lunch Money over the years. I find the “slowly build a company over time by making improvements for users each week” to be such a romantic idea. And I love the idea of small scale business who scratch a simple itch for their customers and get a bit of money in return.

My planned structure:

### Progress I made this week: 

- ****:
- **Airbnb initiative**:
- **Fitness**: 

### Goals for next week: 

- ****:
- **Airbnb initiative**:
- **Fitness**:

So, in that 👆 spirit, here are my goals for this upcoming week:

Goals for next week:

    • Do mock up of very minimally viable first iteration of the app
  • Airbnb initiative:
    • Determine where I want to buy (Maine or Colorado)
  • Fitness:

Talk to you all next week!