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A reset in 2020

HEY! I'm finally doing this thing I vaguely promised to do on my way out of Atlassian's door.

I wanted to give an update on my 2019 and let you know what I'll be up to in the future.


First month of retirement and man was it busy. With Miles due in mid-April we were scrambling (read: calling our builder and yelling at him daily) to get the house ready for move in ASAP. Had a weekend babymoon at the Belmond Charleston - highly recommend as it was beautiful and right across the street from the city market. Eat at SNOB and start off with a few Barn Raisers. Thank me later.

Oh we closed on house on the last day of March 🙌🙌🙌

You'll have to follow Caroline to see this but here is a story collection of the process from start to finish. Some other links in here are to Caroline's private Instas so just go follow her.


It was full on move in mode. We had just a few weeks to get ready for Miles to come. Honestly, we moved in a little early because we wanted to be in by the time he came, so some things were still slightly under construction. Yes it was very annoying.

Our little man was born on April 16th. Ask me about Parker's birth story next time I see you if you don't know it - but my God was Miles easy compared to Parker. We were able to get a little more sleep in the first few weeks with the help of a night doula which I highly recommend to any expecting parents.


We settle into life with two kids pretty horribly if I'm being honest. In the beginning Miles was exceptionally difficult and didn't like me at all. Things between Caroline and I were particularly hard as I was really struggling to bond with Miles and Caroline was still recovering. We made it through and are stronger for it but man it was tough.

We did a few days at our favorite place in the world (Topsail Island) and went hard at a Hootie and the Blowfish concert.


Not sure if it was June or a bit later but things drastically turn better with Miles. He quickly became (and remains to this day) the chillest baby ever. He's perfect and easy and adorable and our family is everything I could have ever asked for.

Before Miles came we were fairly certain we were going to have three kids but we pretty quickly realized that we're good with two 🤗

We have a "Sip and See" for Miles which essentially acts as our first official welcome home / house warming party.

July - November

Just living life now. Parker turns two. We go to the pool a lot. Have my first weekend alone with the kids when Caroline goes on a bachelorette trip. Get kicked out of the WVU vs NC State game. Do a weekend golf trip in Myrtle Beach. Go to Asheville for the weekend. Host our first Thanksgiving.


I was mildly depressed for a few years from around the time YC ended to about halfway through our stint in Denver (about 2.5 years). I felt inklings of this again in November and it really started getting ahold of me in early December. Angry a lot. Restless just waiting for something to happen but not knowing what that is. Feeling pretty nihilistic about everything. Feeling pretty aimless.

I did a few therapy sessions (with John Clarke - highly recommend) and wrote a letter to myself as an exercise to help find my path forward.


I'm 30 now. It's a new decade. Everything is lined up to start the next chapter off right.

I'm doing an experiment this year and created a Personal Board of Directors. I'm tired of not following through on the changes I want to make and I think having a group of people to hold me accountable might just be enough to make the difference.

I used the VTFM model from Atlassian and I'm tracking the Focus and Measures (which are really just OKRs) in this doc. Feel free to join in on good natured prodding me to get my ass in gear.

In the last several months of 2019, all of these people were telling me that I'm so fortunate to be able to choose what I want to do next. My gut reaction was always "Fuck you I have analysis paralysis and I'm miserable" (though I responded more politely). But it's finally sank in that I am incredibly lucky to have this opportunity.

So I'm taking this opportunity to aim extremely high in 2020. I don't know exactly what it will be yet but I'm going to throw myself into finding out how I can make a huge impact on the startup scene here.

Hope your 2020 is off to a great start! I'd love to catch up with all 10 of you that are subscribed to this right now so grab some time w/ me to chat soon!

Once per quarter I send out a newsletter that has some person updates and a round-up of any posts from the past three months.