2022 Review — A year of growth and managing stress

2022 was a good year, but a busy year. Far too busy. I found myself overly involved in the details of the business and handling many responsibilities I needed to delegate. All of that took a toll on me.

We had some key executives leave (more on that below), and it left me in charge of doing too many different jobs. A lot of energy went into hiring the right new people for these leadership roles. It was time-consuming work, but necessary to make 2023 look a lot more calm in comparison.

ConvertKit

2022 was a big year for ConvertKit. Here are a few of numbers:

• We grew ARR 15% from $29.14 million to $33.5 million (up from 12.8% growth in 2021). Our goal was 20% growth, which we missed by $1.4 million ARR. 
• Paying customers grew 17.6% from 38,219 to 44,939. 
• Commerce GMV grew from $3.7 million in 2021 to $8.27 million in 2022 (our goal was $9.1 million). Our revenue from GMV was about $290k for 2022. 
• We launched the ConvertKit Sponsor Network mid-year and booked over $520k in sponsorships, of which our revenue is about $122k. 
• User churn dropped for the year from 5.3% to 4.7% and revenue churn dropped from 4.5% to 4.3%. The trendlines on both are looking really good for 2023. We also hit 100% net dollar retention for the first time in November.

This healthy growth, increased profits, and new revenue streams put us in a really solid position with the market downturn. When most companies were struggling to raise funding and laying off their team (the tech industry laid off over 150,000 employees this year), we were able to continue our steady hiring and keep serving creators.

Rebuilding our leadership team

Last year after I decided not to sell the company, we had three key executives leave ConvertKit. That meant rebuilding the executive team. We hired Amy Newell early in 2022 as VP of Engineering (she was most recently a senior engineering leader at Wistia) and she quickly got our engineering team in a good place and started actively recruiting to grow the team.

Hiring a new growth leader took more time. I spent the first half of the year trying to recruit for the role from my own network, but after that didn’t work for the calibre of leader we needed, I decided to hire a recruiting firm and pay their six-figure fees. Hiring The Cole Group was a great decision. Every candidate they sent me was on par with the very best candidates I was able to recruit on my own.

In November we hired Dave Altarescu as our Chief Revenue Officer. He led the US launch for Spotify back in 2011 and then had a long career across the tech industry. More recently he joined Anchor as a small company and scaled them to an exit to Spotify. In just two months he’s already made a big impact on our growth team.

Managing stress

Because I spent the year playing dual roles of VP of Growth and CEO I stretched myself far too thin and overworked. It culminated in the fall in getting regular anxiety attacks. I’d find myself lying on the floor of my office or sitting in my car outside a coffee shop unable to make myself function. 

Through coaching, regular exercise, and relying more on my team I’ve been able to get through it, but the stress isn’t sustainable. Now that I have a fully staffed team I’m able to change my relationship to work and what needs to get done. 

I’m far too involved in the details in the company. That may have worked before, but now I need to move up a level and really let my leaders lead. My job is to set the vision, make sure we have enough money to fund and scale our operations, and hire great people. 

Retreats

We hosted our first retreat after COVID in Tulum, Mexico with about half the team. While we missed a lot of people, it was amazing to get together for the first time in two years. Then we hosted a second retreat in upstate New York with almost the full team. Getting together in person continues to be the highlight of my year. 

What we built for creators

2022 was a huge year for our product:

• ConvertKit Commerce — We really rounded out ConvertKit Commerce with upsells, VAT support, embedding products in your emails, directly linking to the checkout page, selling multiple quantities, payment plans, selling in multiple currencies, and much more.
  
  
• Email editor — Most editors are either a good writing experience or a good design experience. Medium is great for writing, but impossible to design a layout in. Our competitors in the email space like MailChimp or Flodesk are great for design, but their block-style editors are painful for writing.
  
  My dream has been to make an editor without compromises: it’s clean and elegant for writing (since words matter most), but you can layer in layouts and themes to make a beautiful design. It’s the best of both worlds.
  
  To make that a reality we rewrote our editor from scratch, designed a new editing toolbar, theming engine, and introduced layout blocks. We have a few more big releases coming early in 2023 to complete our vision.
  
  
• Account notifications and digest emails — While a simple feature, notifications for new subscribers and purchases as well as a weekly digest summarizing your stats were some of our most popular new features this year.
  
  
• Broadcast API — We continue our commitment to an open platform and internet by making it so you can create and schedule broadcast emails through our API.
  
  
• Subscribe Preferences — Your subscribers can select what they want to subscribe to from your newsletter. A top request from professional creators.
  
  
• Quick Find — As a professional creator I care about using a tool that is fast. With Quick Find you can press CMD + K to search and quickly get to shortcuts across the app. There’s now keyboard shortcuts for all major actions. To create a broadcast you press N for new, then B for broadcast. To view your subscribers press G for go then S for subscribers.
  
  
• ConvertKit Sponsor Network (CKSN) — This is something brand new, that to my knowledge has never been done by an email company before (though it has since been copied by a competitor). With CKSN we use the network effects of running the largest creator email platform to book sponsors for creators, then we handle all the contracts, invoicing, payments, copywriting, and reporting for them. It’s magic.
  
  Since turning it on for my newsletter I’ve been earning over $3,000 per month with very little work. We’ve already booked over $520,000 in sponsorships in the second half of 2022 and are looking to scale a lot more in 2023. Our bottleneck is enough brands that are looking to sponsor, so if you know of one, point them here. 

For the full list of our releases see our public changelog. Next year our goal is to significantly increase the amount of money we are paying to creators. 

Craft + Commerce is back

After a long hiatus for the pandemic, we brought back Craft + Commerce. There’s nothing like meeting creators in person and I’m so glad to make it happen. While still smaller than our peak year, we had a lot of great creators make the trip out to Boise to learn how to grow their audiences and turn it into a thriving business.

We’re hosting the next event June 8-10 in Boise. We’re switching venues this year, but still staying right downtown. You can grab your tickets here.

Other businesses

Airbnb

Our Airbnbs did really well grossing $654,341 from 16 units across 7 properties. Each year I make a forecast to refine my prediction skills. We missed the forecast by $42,374. The main factor is that revenue was really strong through June, then July and August dropped substantially. What were normally the peak months of the season were mediocre at best. 

Here you can see revenue and total units for our main Airbnb business that includes 13 units:

Our only property purchase this year was buying my childhood home in the mountains from my dad. We purchased it for $400,000 and then spent another $180,000 remodeling and furnishing it. I’m blown away by how it turned out.

While it hasn’t performed as well as I’d like on Airbnb, it’s been really special to keep the home my dad built in the family. 

I don’t expect to add more properties in 2023. The business is now at a nice size, has a full-time employee to manage it, and is turning a healthy profit and building a lot of equity. If we do a new property it would probably be a couple’s getaway type property in the mountains outside Boise. 

From Boise

From Boise is a local newsletter about stories and happenings in my hometown of Boise, Idaho. I had the idea 2 years ago and we launched in March 2021. This year we turned From Boise into a real business.

At first Marissa was handling the editorial side and I was handling the business. Then in September we officially filed for the LLC, set up separate bank accounts, and I handed it all over to her to run. I’m still advising, but not actively spending time on it. 

We grew from 7,900 to 21,100 subscribers. Revenue was $39,297, with $68,933 in expenses, for a net loss of $29,635. Revenue was up a lot in the last quarter and expenses stayed steady so we’re in a good position to be profitable in 2023.

Our goals for 2023 are 40,000 email subscribers, $100,000 in revenue, and to be profitable.

Cerro Gordo

2021 was pretty messy for Cerro Gordo. The two main owners had a major disagreement and the large group of investors became divided on how to move forward. I spent a lot of time mediating the discussion. Thankfully in Spring 2022 we all reached an agreement and Brent bought out the other owner. Then Ryan Holiday and I each put in significantly more money to buy out most of the other investors. We’ve now got a really good crew dedicated to growing and preserving the ghost town. 

As Brent said in one of his videos, compared to how many conflicts ended in Cerro Gordo over the years (gunfights and murders) this one was pretty tame. 

We visited once this year, bringing the kids and a few friends. It was the first time I’d visited while Brent was there and that was especially fun. A few highlights included amazing dinners with the community, exploring miles of mines, driving crazy roads out to the salt tram, and watching August explain the finer points of Minecraft to Brent.

All the concrete is now finished for the new hotel and framing will start in the next couple of weeks. 2023 is going to be a big year for Cerro Gordo! I hope to visit a few times and am working on picking up a new skill to make that easier (more on that later). 

My blog & audience

My biggest personal goal was to grow my Twitter to 100,000 followers from 43,000. I started with a big push early in the year, then dropped off as ConvertKit got really busy. I consistently added followers throughout the year, then a final push in December got me over 100k with a day to spare. I also started reposting threads to LinkedIn and quickly grew to 25k followers there.  

I earned $39,209 from digital products (mostly my money newsletter) and then $21,057 from sponsorships on the ConvertKit Sponsor Network for a total of $60,266. That number feels remarkably high for how little time I spent on it. 

While it’s still very early, the Sponsor Network is a game changer for newsletters. I can’t wait to see how it grows in 2023!

While I stayed consistent with my newsletter, the podcast dropped off when things got so busy. I’m looking forward to bringing it back more consistently in 2023. I’ve hired a talented creator to be my head of marketing and I’m excited to see how she grows everything.

Family life

It’s cliche, but I’m really noticing how quickly the kids are growing up. Josiah just turned 3 and August and Oliver are 8 and 11. We’re doing a half homeschool, half private school setup that is working really well for them. It strikes the balance between plenty of time with other kids, other adults telling them what to do, and not spending too much time on school. 

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Most of our summer was spent outdoors working on the farm, playing at the park, and taking the family boating. The kids love to go tubing (so long as it isn’t too scary) and driving the boat (trying to make it as scary as possible). August tried wake surfing on the board with me and we got up on the first try!

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I still didn’t pull off a 360 without the rope and catch the wave again. Hopefully this year!

Hilary’s sister Hannah visited from Thailand and it was great to have her and her son around for half the summer. 

This winter we also started skiing and the kids took to it really quickly. 

Jury duty

One odd experience this year was doing jury duty. I ended up being assigned to a sexual assault case that took place over two weeks. It was emotionally challenging, but also really encouraging to see the legal system at work. I’m really thankful to have had that experience. The defendant was charged with four crimes and we said guilty on two, not guilty on one, and then we were a split jury on the final count. 

Travel

I traveled a little more than last year (12 trips compared to 9 last year), but still not nearly as much compared to pre-pandemic: 

1. Tulum for the team retreat
2. Sailing in Belize
3. Cerro Gordo
4. Montreal for running remote
5. Kelowna BC for Dan Martell’s event
6. Team retreat in NY, followed by NYC weekend
7. Camping over labor day
8. Mexico City with New Story
9. Asheville for family vacation
10. San Diego for meetings
11. Mountain house weekend
12. Portland for exec planning

Our first retreat after the pandemic

My first trip of the year was to Tulum for our first team retreat after the pandemic. We had a smaller group (about 35 out of 65 on the team) this time, but it was good to get everyone together. We stayed at a small hotel called Ana y Jose that was really beautiful. 

You can see all the different pressures on Tulum from wellness tourists, to partiers, to cartels. It was an odd combination of fascinating, beautiful, and sad. 

Sailing in Belize

This was my favorite trip of the year. Hilary and I got away with close friends and family for a week without the kids. We chartered a Gulfstream IV to fly direct from Boise to Belize and had the best time. From there we picked up a 45 ft catamaran in Placencia that was our home for the next week. 

I made a rule that I need to spend 5% of what I earn on ridiculous splurges. After selling a little bit of ConvertKit stock in 2021 my 5% covered this vacation. 

Uncle Ray, who taught us all how to sail, came along as a passenger on this trip and it was great to have him!

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Mexico City

As our income and net worth has grown I’ve often thought about if luxury travel (nice hotels or first class flights) would spoil our kids. A friend shared that I shouldn’t worry as much about how moving from the 95th percentile in global wealth to the 99th percentile would affect them, but instead spend more time showing them the broader world and understanding the 50th percentile.

For the last 5 years we’ve been supporting a lot of great organizations including New Story Charity, Earth Mission Asia, and charity:water. I’ve always wanted to visit in person and bring my older kids. 

This year we made it happen with a trip to Mexico City with New Story Charity. We got to tour the city, visit the homes we helped fund, meet with an MIT team that is pioneering new affordable building techniques, and more. 

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I loved spending that time with Oliver and August. They really enjoyed the trip and were exposed to entirely new experiences and cultures. I hope to do another trip like it in 2023.

Speaking of charity work we also raised ~$80,000 to build and outfit a new outpatient facility at an Earth Mission Asia clinic in Myanmar. Thanks to everyone who donated!

Asheville

Our family vacation for fall break was to Asheville, North Carolina. That’s a part of the country I’d never visited before, so it was really fun. We stayed right downtown and enjoyed exploring the city and walking to so much great food.

Our friends Justin and Rebecca Rhodes, who have inspired a lot of our homesteading, live just outside Asheville and we were able to get together with them a few times. Our families hit it off right away and we hope to visit again soon.

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We also visited Biltmore and stayed at the Market Gardener’s Cottage which was a fun piece of history. 

Mountain house

We had quite a few trips up to our newly remodeled moutain house. First to finish construction and haul up furniture, then for getaways with friends and family. It’s such a treat to see my kids experiencing the same house, hiking trails, swing set, and LEGOs that I did. 

The farm

Our farm continues to be one of the best decisions we’ve ever made. We have plenty of space, but are just a half mile from stores, our gym, and only 15 minutes to downtown Boise. We continued to chip away at projects including:

• Landscaped the Airbnb property next door
• Turned the Airbnb garage into a game room
• Built a bridge across our stream (it still needs a railing)
• Built a small greenhouse
• Had a beautiful fresh cut flower garden

The hardest thing this year was fighting with irrigation. Issues upstream caused us to spend weeks without irrigation water in the peak of summer heat. That meant we spent a lot of time running hoses across the back fields to try and save our trees. We only lost 6-8 trees, which isn’t too bad considering how it could have been.

I still haven’t hosted a retreat at our farm. 2023 is going to be the year it happens.

Fitness

2022 was average for fitness. I made it to the gym consistently 1-2 times a week, but didn’t push myself enough to do much more than maintain a decent fitness level. I did push myself for our annual ConvertKit 5k, setting a new personal best of 21:50 and beating my 22 minute goal. I had forgotten that at the beginning of the year I set a 21 minute goal. I’ll make that this year!

My favorite fitness addition for the year is playing indoor volleyball. We’ve played in the park each summer, but this year I started playing on indoor teams in the city league. Doing that consistently has made me a lot better and it’s so much fun. We’ve had a few weeks off because of the holidays and I really miss it!

At the end of the year I bought a walking treadmill to put under my desk. I’ve been doing that a lot on zoom meetings and it significantly increases my steps per day. During a busy meeting day I can hit 15-20k steps per day.

Goals

Here’s how I did on 2022 goals:

1. Grow ConvertKit revenue 20% to $34.8 million — Nope. Hit $33.4 million or 15%. Missing the goal by $1.4 million. 
2. ConvertKit Commerce GMV crossing $2 million in a month — No. We grew like crazy, but only hit about $1M/month. 
3. Take an epic sailing trip with Hilary — Yes! We did a big splurge and took my favorite trip ever. 
4. Grow Twitter audience to 100k followers by April 1, 2022 — Done! Not April, but it happened by the end of the year. At the end of December I was still 9,000 subscribers away, but with a big final push I got it done. 
5. 100 gym workouts — Hit it! Though I didn’t push myself super hard. In 2023 I want to stay consistent and push myself harder.
6. Run a 5k in under 21 minutes — Not quite. I hit 21:50 in the 5k, shaving 40 seconds off my previous best time. 
7. 50 newsletters, 50 podcast episodes — Hit it with newsletters, not with the podcast. 
8. Grow From Boise to 20,000 subscribers and reach profitability — We hit 21k subscribers and had two profitable months! For 2023 the goal is to be profitable for the full year.
9. Cross $750,000 in Airbnb revenue — Nope, $95k short. It was a combination of an overly optimistic goal and slower airbnb revenue.

I also hit another goal from a previous year by visiting charity projects in person with the trip to New Story. 

My 2023 goals:

1. Learn to ski — I’ve been snowboarding off and on since high school, but this year I’m switching to skiing to help teach my kids. I’ve been skiing for a month now and already having a lot of fun. 
2. Get my private pilot’s license — I’m learning to fly! Over the holidays I finished ground school and in early January I started flying lessons. This is going to make getting down to Cerro Gordo so much easier. 
3. Run a 5k in 21 minutes — Same goal as last year. The hardest thing for me is training through the winter since I hate running in the cold. 
4. Go sailing twice — Sailing vacations are my favorite and I’ve been doing one a year. This year I want to do two!
5. Grow my personal audience — I want to grow my personal audience to get a lot more attention and customers for ConvertKit. My specific goals: Twitter 200k, LinkedIn 100k, newsletter 40k subscribers. 
6. Be a lot less stressed — 2022 was very stressful. I was doing multiple jobs for almost the entire year and it took a toll on my health. Now that I have a full exec team my goal is to get out of the weeds, spend more time on strategy, and really scale ConvertKit.

2023 has already started really well and I’m especially excited for what’s coming at ConvertKit. Our new network business is scaling fast and we have other big plans that will transform how creators earn a living. 

It’s going to be a pivotal year.