My 2024 In Review

I’m writing this as I sit on the couch next to a sleeping two-week-old. I don’t have much time before my two-year-old and four-year-old emerge from their room (again), so let’s talk about this year!

tl;dr — I quit my job, built a business, started my job again, sold the business, and had a baby.

The start

As you might have read, I quit my job at Shopify at the beginning of the year.

I was a little burnt out but also eager to try something new.

That “something new” ended up being “something existing, just full-focus:” Barkpass.

January - March: Barkpass

With no day-to-day employment, I turned my focus to building our existing side project, Barkpass.

I did sales, research, lots of product work, and planning. And Bri and I went to our first (and only) trade show!

This was a really fun but challenging part of the year. I learned a ton about going solo and building something with complete focus:

1. It’s quite lonely.
2. It’s harder than I thought.
3. I didn’t get as much done as I thought I would.

There’s also the creeping pressure of finances. It’s weird—you gotta pay bills! This is a monkey on your back day in and day out.

I also learned a lot about product-market fit and addressable markets. Barkpass is in a very interesting position here, and I’m not very well-suited at my capacity to push the business forward as it’s positioned today.

However, there were really bright spots during this time:

1. I focused much more on my health: drank less, ate better, did a lot of gratitude meditations.
2. I loved working out during the middle of the day.
3. It was so fun having a clean slate at the beginning of my day with the absolute freedom to work on whatever I wanted to.

Other stuff happened during this time. My uncle in Seattle passed away, so I took my oldest son Barrett (4yo) and my dad (68yo) on an airplane ride to visit my cousins up there and attend the funeral. It was a fun trip, because Barrett got to meet his Seattle cousins for the first time and hang. We keep in touch with them over video chats now and then.

I’m bummed, though, that our flight out to Seattle lined up exactly with the Super Bowl, because Iowa State alum Brock Purdy was playing in it. The 49ers didn’t win! Oh well.

Then came March 31st, Easter Sunday, when we found out we were going to have a third kid!

April: What am I going to do?

This set into motion a series of thoughts: I either need to swing for the fences now with the goal of making more income by the time the baby arrives, or find full-time employment again.

And this is assuming my wife’s pregnancy goes perfectly well. If there are any complications that leave her out of work or with major hospital bills, having no current income would not be ideal.

So I set out to find a job again. I spoke to a couple different places and had some lovely conversations, but I ultimately came back to Shopify. I’m really glad I left on good terms and preserved good relationships with people there.

May: Back to work

I started back at Shopify in May, and it was great. I saw all my old pals and got a fresh start on a new team. And the “financial” monkey was off my back once again.

I didn’t want the feature work I’d started on Barkpass to go unfinished, so I decided on this new weekday routine:

• 4am: Wake up, drink coffee and work on Barkpass
• 5am: Gym
• 6am: Maybe work on Barkpass, but likely tend to my children who have awaken
• 7am: Make breakfast for the family
• 8am: Take my children to school; start work
• 12pm: Lunch and walk dogs with wife
• 4:45pm: Pick up children
• 5pm: Make dinner for family while kids hangrily scream at us and demand eighty different things
• 5:30pm-7pm: Clean up dinner while also somehow entertaining children
• 7:30pm: Bath time (children)
• 8pm: Bedtime (children)
• 8:30pm: If I have any shred of energy left, work again. But more than likely, watch a show with my wife and go to bed.

The linchpin of this schedule is, unfortunately, the 4am wakeup. This undisturbed hour of focus in the morning is my hour. It feels incredible when the rest of the day is decidedly not mine.

I feel accomplished and satisfied when I’m able to do something at 4am; I’m at peace the rest of the day surrendering to the needs of others. This is nice, but it’s tiring.

June: Travel

We took the boys to Naples, FL in June!

We didn’t plan to go to Florida. In fact, our original plan was Colorado Springs, CO. But I talked my wife out of it: the almanac showed that the weather wasn’t likely going to be warm enough to do outdoor pool, and that was the only amenity of the trip that our 4yo was going to really enjoy. And most of the other activities in town were hiking-related. We’re not much for hiking anyway, especially with a 2yo.

So I thought, “Where can we go that’s a non-stop flight from Des Moines, IA that’s also warm enough to swim?” Houston, TX randomly popped into my head—I’d been to Dallas and Austin before, and both of those places were nice. Houston’s gotta be nice too, yeah?

Well, almost every one of my friends I told about this decision tried to talk me out of it. Apparently Houston is just incredibly hot, perceptible to hurricanes and storms, massive and sprawling, and not a tourist destination.

So, we chickened out again. We booked the Florida trip (which was also hot) but it was much more predictable. We got some pool time and some beach time, and the boys had fun.

I also went to Toronto, CA for work. Shopify held a full company all-hands: we’re talking like 8,000 people in one room.

I don’t know about you, but I thought I understood how many people 8,000 people was, at least digitally. But it wasn’t until I was bumping shoulders with a sea of anonymous coworkers that I realized how small I was in the grand scheme of things. Quite humbling.

However, Toronto was super fun. I caught up with many of my old coworkers for the first time since leaving the company, hacked on some cool things, and got to see Weezer and The Roots perform. Very cool.

Also: we bought a John Deere riding lawn mower with a snowblower attachment. Big upgrade from the push mower!

July - August: Body Tutoring

I’ve been working on my fitness for some time now. CrossFit for eight years. Dieting on-and-off. While I’ve seen some success, I’ve also grown tired of being the only person to hold myself accountable.

People on the internet (Adam, Joel) have written about their positive experiences with MyBodyTutor, which is a service that hooks you up with a nutritional coach. It’s costly, but I decided to give it a shot.

So far, it’s ben great! My coach Chris does an excellent job holding me accountable and teaching me new things about nutrition. I’m still using it today and am inching super closer to one of my big goals: weighing less than 200lb for the first time in my adult life.

In August, we went to the Iowa State Fair. We were also potty training the 2yo that week, so it was a bold move, but a success.

I also bought a new car! A Jeep Wrangler. I was going to buy a Tesla, but Iowa makes it very difficult to do that. So I found a used hybrid instead which gets me electric driving the two-ish miles I need to drive in town every day. I love it.

I went to a couple Iowa State football games this summer.

First was Iowa State @ Iowa with my father-in-law:

And then I brought Barrett to a home game in Ames:

I also started a podcast with my friend Austin Crim called “Josh and Austin Figure It Out.” It’s been fun getting back on the podcast horse after my wife and I spun down our fun little marketing podcast years ago. We’ve got some momentum going, and I look forward to recording more in the new year and hopefully having some guests on!

September: Selling Barkpass

Out of the blue, we got a LinkedIn message from a guy who was planning to launch his own pet licensing software business, and he wanted to chat with us first because Barkpass was one of the only players in this space already. We entertained the idea of talking to him without any real expectations.

However, we really enjoyed our conversation, and it was clear he was very interested in either partnering with us to build Barkpass or purchase our business altogether.

From an exit standpoint, Barkpass was in an interesting position:

• Too big to sell to an indiehacker: Real customers and governments depend upon it, and the scope of the software is non-trivial.
• Too small to sell to private equity or bigger pet software company: They’re typically looking to acquire customers and revenue in the millions $$, not a product specifically.

The buyer, Steve Zeidman, ended up wanting our product as a launching pad for his new pet licensing business, and this opportunity was unlikely to come around again.

Bri and I agreed that selling the business was in our best interests at this time, especially given our third kid arriving soon, so this set the sale of Barkpass into motion.

October - December: Goodbye “baby,” hello baby

After months of technical due diligence, financial due diligence, legal review and negotiation, we arrived at a selling price and were ready to close on the sale of Barkpass.

November and December were a whirlwind for us: we weren’t sure when the baby would come, so we didn’t travel for Thanksgiving. We were busy putting the finishing touches on the sale of the business while wrapping up our respective day jobs before going on parental leave. And then Christmas shopping and preparing for the holidays while also preparing for the baby’s arrival.

Bri gave birth to our son Levi on December 6th, and we closed on the sale on December 12th. I would not recommend having a baby and selling a business in the same week 😅.

It still feels like we’re in the thick of it: sleeping in two-hour stints, getting used to caring for two other children while keeping a third kid alive. This month has very much been the end of one chapter and the beginning of another.

Bonus: This year in music

In no particular order, here are some musical things I’ve enjoyed this year:

• We revived our Rhinestone Theater tradition in June at our new house and not in our creepy basement. Also: with LOTS of children who didn’t exist the last time we held a Rhinestone Theater in 2019. I gotta say, it was still a lot of fun, but kids really bring another dimension to it. I think we’ll try to do it again, maybe as a “Rhinestone After Dark” adults-only event.
• I played sax in a quintet with my friends from college—we call ourselves The Greensleeves because we’ve traditionally played Christmas tunes as Salvation Army bell ringers—but this was our first “secular” concert and it was lovely.
• I bought a flugelhorn and intend to teach myself how to play Chuck Mangione’s “Feels So Good” on it.
• I listened to a lot of Chappell Roan and have enjoyed seeing the her meteoric rise. Here’s my take on “Good Luck, Babe!”
• When I’m making breakfast with the boys, I’ve started playing “It’s a Great Day to be Alive” by Travis Tritt. There’s also a Ben Rector cover that I love.

The End

While I’m looking forward to Christmas this week with family, another part of me is looking forward to one year from now when most of this craziness will be in the rearview mirror, and we can really slow down and enjoy the season from start to finish.

But you know what they say: don’t take life for granted. Live it now.

2024, you’ve been a year. See you in 2025!