After I sold WebMerge and phased myself out of the day-to-day, I told myself I was going to take a long break from “work” and related activities. For the first few months, that plan was fantastic. I got back into all my favorite hobbies and sports like surfing almost daily, playing golf, driving race cars, learning a new language (Italian!) and more.

However, I’ve found that there isn’t a way to turn off an entrepreneurial mind. I’m always seeing problems and wondering how I can fix them. From there, it’s only a matter of time before a good idea crosses my mind that I want to see if it has legs. That idea came to me recently when talking with my wife about life/death planning - specifically thinking about our parents.

I’ve never been a big user of social media. I was always too busy working on my business and didn’t see value in constantly scrolling through feeds on my phone. However, now that I don’t have day-to-day business interactions and I’ve put on my investor hat, I’ve found myself using social media more often.

Primarily, I’m using LinkedIn to look for opportunities and keep up with old colleagues. However, I’ve had LinkedIn for 10+ years so I have a large number of connections and my feed is very noisy. Many of those connections are people I barely know or have never met. When people are just getting started in business, they want as many connections as possible to make themselves look better in the eyes of other people. I get it—I was the exact same and that’s why I have so many (useless) connections. Would it be better for me to have fewer connections?

Since I was young, I’ve always had an appreciation for cars. I wouldn’t go as far as to call myself a gearhead but I really enjoy driving cars, admiring the sound they make, and dreaming about how cool they look. Growing up, I didn’t really follow racing too closely, but I would watch the big races like the Indy 500.

Fast-forward to 2020 and I had the opportunity of participating in a Ferrari driving school that took place on a real race track. We learned how to (safely) push street cars on the track to see what they were really capable of. You’d never be able to drive them like that on the street. I knew I was going to enjoy the classes, but I was hooked.

I use “retirement” in quotes because the thought of being retired makes me feel too old and I’m not entirely sure how long this will last. In 2020, I phased myself out of WebMerge, a business I founded and sold to Formstack, and now I don’t have a job and don’t currently have plans to find one.

Leaving a job where I was always on call for almost 10 years, is a really weird feeling. That first day after I removed my work email and slack from my devices, I had a really weird feeling. I woke up with 0 emails and 0 slack messages. Literally nothing required my attention - that’s a first.

Routines are everything. Without a routine, I’m not sure how I would function each day :) Routines cut down on the decisions that need to be made and makes me more productive.

Routines give me clarity and normalcy throughout the day and ensure that I don’t miss anything I have to do.

Every day, I wake up and make breakfast - a protein shake with blueberries, spinach, oatmeal, cinnamon, peanut butter, and almond milk. I hangout with my daughter during breakfast and try to make her laugh.