2018 in review — A year of big risks

2018 was simultaneously one of the most challenging and rewarding years of my life. While many things didn’t go the way I would have hoped they would, I’m proud of the risks we took and how hard we pushed to build the team, company, and world that we want to exist.

I’ve also never been so grateful for recurring revenue as I was this year!

Some of the most painful things are still too fresh for me to want to write about, but I expect I will once more time passes. For more context on my life and how things have changed overall, you can read the posts from the last 7 years (201720162015201420132012, and 2011).


Oliver and August are now 7 and 4 years old. It’s so much fun watching them grow up. They are both playing soccer each week and really enjoying it. Life on the farm has been great for the boys. I love what they’ve been exposed to when animals, construction, work, and just room to roam.

Recently they’ve started to learn more games and be quite competitive at card games like Bang!

Parenting continues to be one of the most rewarding things I’ve ever done. Though it’s definitely challenging. In fact, as I write this the boys are yelling at each other about who knows what…

This isn’t just a floor puzzle of the United States (as you’d think), but it’s also August in perfect camouflage. 

The farm

Last year we moved to a small farm in Boise. This year we were really able to settle in and start all of our projects. The biggest of which were building a walking path around the entire property and installing sprinklers through the entire back field. The sprinklers took months longer than expected because our contractor was so busy.

But ultimately it was worth it. We now have a commercial-grade pop-up sprinkler system, sourced from free irrigation water, covering three acres.

I also spent quite a bit of time in my shop on woodworking projects. I’m looking forward to even more of that next year!

Hilary and her brother Philip getting ready to harvest honey from our beehives.

Marilyn (one of our six goats)

We rented a skid steer for a week to build a walking path around our property.

Oliver and one of the baby goats born in the spring of this year.


I continued to play a lot of soccer and loved every minute of it! At the peak I was on four teams playing 3-6 games a week! It’s been fun to see improvement since I’ve only been playing for a few years. Though so much soccer meant I didn’t go to the gym. That needs to change!


  1. Los Angeles for sales meetings
  2. Oceanside for our team retreat
  3. McCall for weekend vacation
  4. San Diego for Traffic and Conversion
  5. Boulder for the Reboot CEO Bootcamp
  6. Austin for the Dynamite Circle conference
  7. Las Vegas for Microconf
  8. Phoenix for a Taylor Swift concert
  9. Washington State for a mastermind retreat
  10. Toronto to eat chocolate chip cookies (seriously)
  11. Philadelphia for Podcast Movement
  12. Santa Cruz for a wedding
  13. McCall for our summer team retreat
  14. Austin for TravelCon
  15. Park City for Mastermind Talks
  16. Cerro Gordo to visit our ghost town
  17. San Antonio for the Inc 5000 conference

One of my personal highlights was going flying with my friend Chris in the Vans RV-7 he built.

At 17 trips I’m down two from the last couple years. There also wasn’t a big vacation like Hawaii or Barcelona like in previous years. I’m making up for that by heading to Hawaii in a couple weeks.

In my recap from last year I said I wanted to travel more with the kids. That just didn’t happen. Life on the farm kept us busy and we didn’t do very much family travel.

Right now I don’t have much travel planned for this next year. I’d like to be more spontaneous with some more trips (we have an insane number of airline miles to use!), so maybe we’ll just pick a destination and go.

Family photo on a trip to California this summer.

Personal projects


I didn’t really do anything with my video this year. But I did release a single video at the end of the year, which was really fun and had a great response. I’ve already got plans to double down next year.

Oliver and August building a sand castle with Levi Allen (a great friend and incredible filmmaker).

Book and course revenue

This is probably the last year I’ll report on book and course revenue since it has tapered off to just $9,092 this year. Down from $15,685 last year. It’s interesting to see these sales still come in, but it’s just not a focus compared to ConvertKit. 

As the content gets older and further out of date I’ll need to decide sometime soon what to do with each book. Authority and Designing Web Applications are more evergreen, but I think I’ll take The App Design Handbook down and archive the site. There are also a lot of old articles and PDFs that I’ll clean up and redirect.


The farm came with a small guest house that we remodeled and rent out on Airbnb. It made $10,459 in 2018, despite being unavailable for three months, including August, which would have been the peak revenue month.

It’s really fun to have a place for friends and family to stay and still have it bring in so much revenue.

After the initial remodel (which I wrote about above) we’ve slowly improved it one project at a time. In August I blocked off the calendar and fully remodeled the bathroom. I still have a few ideas of small things to improve, but now it’s finally to the level of polish and comfort that I want it.

Bought a Tesla

Like nearly everyone who loves technology, I’ve wanted to buy a Tesla for years. I tend to be pretty conservative with finances, so I set a personal net worth goal (outside the company valuation) and once I hit that I splurged with the purchase. Yes, I could have purchased it much earlier, but even though ConvertKit is successful I want to avoid too much lifestyle creep (or at least slow it down).

After careful research I bought a 2016 Model S P90D. In pure black, of course.

Buying used (with 18,000 miles) meant saving about $50,000 off the price—though some of that would have been saved with a tax credit. The car retails for $143,000 and I paid $93,000. Then I spent another $1,400 to have it shipped out from Florida to Boise.

It’s been an absolute dream to own! On the roadtrip down to Cerro Gordo I had no problem driving the entire time. I wrote a post about a few things I really love about it.

Bought a ghost town

There’s a heading I never expected to type in an annual report!

This was a fun, random turn of events this summer, but I got the opportunity to be a small part of buying Cerro Gordo, an old mining town in the California mountains. You can read the full story here:

We bought a ghost town.

Thanks to Brent, Jon, Ryan, and the rest of the crew for including me in this!

The road trip to Cerro Gordo in the Tesla was another highlight!

Exploring Cerro Gordo.

“I never lose. I either win or I learn.”

— Nelson Mandela

In 2018 at ConvertKit we did a lot of learning. While we had a solid year by many business metrics, it didn’t feel like we spent a lot of time winning. Revenue grew from $910,455 to $1,171,395 per month. We hit $13.6 million in net revenue.

Here’s a short list of a few things that happened this year:

  • Rebranded the company (twice). We started and ended the year as ConvertKit, but in July I announced my long-time goal of rebranding ConvertKit to Seva. Ultimately we learned that the rebrand would be hurtful to people we care about and rolled it back.

    At some point I’ll publish the full story.

    On one hand I feel a deep sense of loss knowing that I failed to successfully execute on one of my long-term goals, but on the other I’m proud of making decisions that matched our core values even when they were hard.

  • Formed a board of advisors. In an effort to become better leaders we formed a board of advisors. The first two board meetings were quite successful, giving me clear direction on several important decisions.
  • Named the fastest growing company in Idaho. Thanks to Inc magazine for naming us the fastest growing company in Idaho. In addition to #1 in Idaho we hit #72 nationwide. That included a trip to the Inc 5000 conference and annual gala, which was a great way to celebrate.

  • Hired some incredible people. We grew the team to 37 people in 2018. It’s probably more impressive that our core team stayed this small. We’re continuing to push towards our goal of $100M in revenue with just 50 people on the team.
  • Made tough decisions to let people go. The hardest thing is to let someone go who has made a huge contribution to the company, but is no longer a good fit. That’s one aspect of business that never gets easier.
  • Launched some incredible new features. We completely rebuilt our form and landing page editor, rebuilt every commerce integration to track purchase data, and built a new reporting engine on Elastic Search.

I got to spend time with Ben Chestnut, the CEO of MailChimp

  • Set a new record for our best single month of growth. In March we passed over $73,000 in a single month of net new MRR (expansion + new revenue + reactivation – churn – contraction). Our previous record was about $50,000, so that felt great!
  • Shrunk for two consecutive months over the summer. But we also shrunk for two months in the summer, which was also a first. Next year I want to see us get far more predictable with our revenue growth.
  • Published a book and documentary. I am a blogger launched this summer and it is simply beautiful. It was such a pleasure to work with Caleb Wojcik, Barrett Brooks, Charli Prangley, and others on this project. Check it out here.

Dave Stuart seeing himself featured in I am a blogger for the first time.

Overall I learned a ton, but a few big failures or difficult tasks make me feel pretty beat up by the end of the year. In 2019 we have a clear focus on improving our customer support, rounding out some kinks in the product, and working hard to increase our trial to paid conversion rate.

There’s also a new part of ConvertKit that I think will really change how creators use the product to grow their audiences.


Goals for 2018

In October, with just three months left, I revisited this list and realized how I wasn’t going to hit very many at all!

  • Host another amazing conference. Done! Casey Neistat and Pat Flynn both crushed their talks.
  • Build marketing funnels for this blog. I didn’t do this. I considered forcing it at the end of the year, but instead I just got my content creation off the ground and I’ll revisit email sequences and funnels next year. I still want to!
  • Release a documentary and coffee table book. Done! It’s absolutely stunning.
  • Cross $1.3m in Monthly Recurring Revenue. Nope. We hit $1.17m in MRR. Off by $130,000. We started out really strong, but couldn’t recover from a slow summer.
  • Weigh 175 lbs. This is one of the goals I started on late. In October I started taking it more seriously and have dropped down below 185. Continuing work here I should be able to get down to 175 in a few more months.
  • Relaunch Commit. This didn’t happen. Instead I started using an app called Streaks, which is a much more advanced version of Commit. It’s great! I’d still like to release Commit as a free app, but that is no longer a priority.
  • Publish 12 posts on this blog. Done! Again, I started late, but I’m already over 12 with a few weeks in the year. Getting the blogging habit going again feels really good.
  • Release 12 episodes on the vlog. I restarted the vlog! But so late in the year that I only finished one episode. But I get partial credit, right?
  • Become more effective with my time. Using a combination of Streaks and Forest I’ve become much better at creating consistently. It will take more practice to get to where I want to be, but overall I feel like I’ve hit this goal.

So I hit 4 of 9. That’s not great.

Hilary and I at her cousin’s wedding in Santa Cruz

2019 goals

Looking forward to 2019 I have a new set of goals. Most are centered around a few habits I’ve been working to establish around health, fitness, and creating consistently:

  • Complete at least 50 weight lifting sessions. I’m getting back into a consistent habit of lifting weights. This goal isn’t too aggressive, but even just an average of once a week would be a big improvement.
  • Publish 50 blog posts. Keep the weekly streak alive!
  • Grow ConvertKit to $1.6M MRR. That would be growing at an average of $35,000 per month.
  • Build a tiny house. I’ve wanted to build a tiny house for years and 2019 it’s finally going to happen! I’m going to keep it here on the farm to use as my office.
  • Publish 12 vlog episodes. Video is so much fun and I’m truly going to focus on it in 2019.
  • Learn to captain a sailboat. I signed up for a week long sailing class in June, 2019. I’m excited to learn a new skill!
  • Sign a book deal. I’m working on a new book that’s been on my mind for years. I’ll be working with a traditional publisher on this one.
  • Redesign this site. I’m going to launch a full redesign of this site to go with the new book and writing.

2018 was a lot of big risks and ambitious projects. I’m proud that we had the courage to make those happen, but 2019 will be a lot more about refining everything that is going well. On ConvertKit we’re going to continue to polish the app, round out existing features, and really work on perfecting the first impressions each customer has with the product.

On the personal side I am working to deliberately establish new habits around fitness and creating. I don’t have big goals besides consistent work. Which I think is perfect for where I’m at!

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