In 2023, I fulfilled a long-term dream of learning to fly, bought my own airplane, started a new company, bought another company, captained a 50 foot sailboat in the Caribbean, took a sabbatical, added more than $7.5 million in annual revenue to ConvertKit, and had a whole ton of fun.
Let’s dive in.
In January of this year, we celebrated ConvertKit’s 10th birthday on the beach in Mexico. Hilary flew down, the team made a wonderful video, and we had a big party. In the last decade, the company has grown from a way to fix what frustrated me with MailChimp to the platform powering the largest newsletters on the web. It’s absolutely wild!
10 years is a natural point to reflect and I did a lot of that as we approached the milestone. Our mission is to help creators earn a living. As I looked at what to focus on over the next 10 years, the primary goal is to get creators paid.
That meant reinventing our business model. We’ve always been good at helping creators make money. But what if we could directly pay them? That’s where our ConvertKit Sponsor Network was born. In 2023, we scaled the sponsor network significantly, launched programmatic advertising, and paid out millions to creators.
This year, we reinvented the company again by launching Creator Network Recommendations. Now ConvertKit is an inherently social product—helping you grow alongside your creator friends. Creator Network is now the single largest source of new subscribers for nearly every creator who is active in it.
Inside Creator Network you can now:
- Run custom welcome sequences just for your Creator Network subscribers
- Embed recommendations for other creators in your emails
- Browse the creator directory to find who to partner with (and get personalized recommendations)
Get started: see who we automatically suggest as a match for you in our matching tool.
SparkLoop & Paid Recommendations
In 2020 when I met Louis and Manuel from SparkLoop, I knew they’d do some epic things. As part of our partnership on their referral rewards program (which we built into ConvertKit Creator Pro), we made a substantial investment in SparkLoop. That turned out to be a brilliant move after they pioneered paid recommendations by launching the SparkLoop Partner Network.
Here, newsletters and brands can pay per engaged subscriber, and creators can earn at any size. My favorite part is that money is going to creators rather than to big tech.
The Partner Network took off like crazy thanks to their drive to grow it and the fact that they built integrations with 18 email service providers. That means the biggest newsletters on the web (Morning Brew, The Hustle, Sahil Bloom, etc) are all sponsoring, resulting in the best earnings as a creator. That creates a virtuous cycle: newsletters that are good at monetizing can pay more for each subscriber, which attracts the top creators to earn on the network, which drives high quality leads, which encourages brands to pay more.
This has been so successful that in 2023, the Partner Network represented over 90% of the entire newsletter paid subscriber market. Newsletters are growing fast and those creators are earning substantial amounts of money to promote them.
In Spring 2023, we closed a deal to acquire SparkLoop and run it as an independent subsidiary of ConvertKit. We’re committed to the open ecosystem SparkLoop pioneered, and we’re excited to keep scaling the payouts to creators.
Louis and Manuel are two of the best operators I’ve ever worked with and I’m so excited to see how they scale earnings for creators in 2024.
This year we also:
- Launched an entirely new email editor that allows you to design beautiful email templates. It’s now the most powerful email designer in the industry.
- Launched a marketplace where designers can build, share, and sell those templates.
- Built and launched a deep integration with Mighty Networks so you can get all your members, content, events, and more from Mighty natively inside the ConvertKit writing experience.
- Made a ton of improvements to our WordPress plugin, including the ability to publish a broadcast to your site, run a custom member-only content area powered by ConvertKit Commerce, embed a newsletter feed, and more.
- All new content snippets so you can share content across your emails much more easily.
- A ton of automation improvements, including the ability to segment subscribers based on how many emails they’ve opened recently.
- Saving your brand colors so they can easily be accessed whenever you’re creating content in ConvertKit.
…and so much more. The team really hit their stride and I’m excited to ramp it up even further in 2024.
In Q4, I realized that we didn’t have the right leadership in place for this next phase of growth in the company. That meant that I parted ways with our VP of Product and several directors and managers. While that was painful, it opened up the opportunity for us to hire incredible people who are the right fit for this next phase.
It’s easy to focus on the highlights, but it’s important to share that leading a company at this scale has a lot of challenges to navigate as well.
Craft + Commerce
For five years we hosted Craft + Commerce at JUMP—a weird, but excellent space in Boise—but this year they decided to focus on non-profit events and didn’t allow us to book again. So we switched to Treefort Music Hall—a brand new concert venue in Downtown Boise.
JUMP had a lot of natural light and allowed all of our workshops to be in the same building (though we were very limited on space). While we missed the natural light, Treefort Music Hall allowed us to make a more immersive experience. We also had to use the hotel across the street for our breakout sessions.
Despite some hiccups from being a brand new venue (like the air conditioning being arctic cold despite many requests for them to increase the temperature), Treefort Music Hall worked out great and we’re excited to be back in 2024. One of the convenient things is the Warehouse Food Hall next door that allows attendees to grab food from a variety of great local places without needing to make reservations or worry about group size.
Craft + Commerce 2024 is shaping up to be our best yet. If you haven’t already, grab your ticket here.
I’ve been fascinated by flywheels for years, but frustrated by the lack of good training about them. Jim Collins covers them at a high level in his book Turning the Flywheel, but there isn’t substantial information on how to put them into practice.
So in 2023, I put a stake in the ground and pioneered the most robust resources and training on flywheels. It started with a flagship essay that I published in the summer, followed by my keynote at Craft + Commerce. I defined the three laws of how flywheels work, taught two live course cohorts on the subject, and taught four in-person masterminds.
Flywheels are absolutely vital to running a successful creator business and in 2024, I’m going to be sharing so much more research, tips, and training on the topic.
Our short-term rental portfolio generated roughly $550,000 in revenue, down from $640,000 last year. That was from a combination of a few properties performing worse, taking our guest cottage off Airbnb (we decided the income wasn’t worth the intrusion on our farm, plus we like the flexibility for family staying with us), and the overall market being slower.
We still paid down a lot of mortgages and made good use of our properties. I was able to channel most of our share of that income (we own 40% of the portfolio and have two other partners) to really improve our farm property.
Marissa, my business partner and editor in chief of From Boise, crushed it this year. Rather than focusing on scaling subscriber growth (we ended the year at 21,800 subscribers), she focused on revenue. That meant growing the business to $89,000 in revenue and $42,000 in net income. I’m pretty hands off and she runs it all. I just enjoy reading the newsletters each week and hearing from readers how much they love it.
How many people can say they own 10% of a ghost town? It’s pretty awesome to be a part of the magic that Brent is creating at Cerro Gordo.
I brought Oliver and August down with me for the investors meeting over the 4th of July weekend. It was great to meet everyone and talk through our dreams for the town.
We got to tour the framed hotel. It’s amazing to see it come to life.
When I first met Sahil Bloom, I knew we were going to be good friends. What I didn’t expect is that we’d start a company together. Oh, and it’s already on pace to earn over $700,000 per year.
At ConvertKit, we sell software and provide a lot of training and support for you to implement the best practices, but we don’t do it for you. That has allowed us to scale to over 50,000 customers, but there are some customers that want it all done for them. While we have some agencies to refer out to, no one who has the playbook absolutely dialed in.
Sahil and I have worked closely together to dial in some fantastic newsletter growth playbooks (he’s now at over 600,000 subscribers) and so we decided to create a productized service where we bring that strategy to other people. At first we were looking to hire an operator to run the business while we supplied strategy and deal flow, but after looking for a couple months we decided we needed a 3rd partner who brought all of his own expertise. Enter Shane Martin.
Shane has scaled multiple agencies to over $1 million in revenue and has the playbooks dialed in. With his operating expertise combined with our playbooks, we’ve been able to deliver fantastic results for our clients.
I still spend 95% of my time focused on ConvertKit and really only spent 3-4 hours a month on Paperboy. Shane is amazing at what he does and we couldn’t have asked for a better partner.
If you’re interested in hiring the best team in the world on newsletter growth, we’re taking on a few new clients in Q1. Apply here.
Becoming a pilot
My biggest goal this year was to get my pilot license. I started flying in February, passed my written test in August, bought a plane in September, and finished out the year by hitting 100% of my requirements for my private pilot license.
These last few weeks as I’ve been flying solo cross country trips and going in and out of busy airspace talking to air traffic controllers, I feel like a real pilot. Because check rides are so backed up, it will probably be March before I actually have my license.
In case you are curious, I’ll document my journey here. If you don’t care about aviation, just skip to the next section.
- Winter/Spring — I started training in a Cessna 152 with Preston, a local corporate jet pilot who instructs for fun, at Nampa, a local non towered airport. I finished ground school through Sporty’s (which I really enjoyed). I didn’t quite make it to solo before Preston took a job on the other side of the country and I was looking for a new instructor.
- Spring/Summer — I switched to Glass Cockpit Aviation at the Boise airport and between a new instructor, flying a new plane (a 172), and a towered airport, I had a lot to learn. Juggling a busy travel schedule, airplane rentals, instructor schedules, and weather meant I didn’t fly that consistently.
- Fall — Just before traveling for a few weeks, I did a pre-solo check ride at the flight school and didn’t pass. Then after a few weeks of travel in September I took delivery of my plane, a 2022 SR22T, nearly new with just 75 flight hours on it. Rather than finish my license in the 172 and deal with scheduling issues, I decided to transition to the high performance Cirrus. I’m glad I did! It took a while to get comfortable (it needs so much right rudder on takeoff to counteract the power), but it’s an absolute dream to fly.
- Winter — Closing out 2023, I got really comfortable in the Cirrus. I’ve finished my PPL requirements and am now just waiting (and training) for the check ride. The winter highlights have been quick flights up to the mountain towns of Cascade (where my mom lives) and McCall for lunches with friends and family.
In 2024, I plan to take some epic trips as I build up experience and work on getting my instrument rating. But for now, the plane just went in for its annual service, so I’m without it for two weeks.
ForeFlight, the app most pilots use to track and plan their flights, does a nice recap at the end of the year (Spotify wrapped for pilots). Here’s mine:
Chronic back pain
This summer, I took the kids backpacking on an easy two-mile trail. The first morning I woke up pretty stiff from sleeping on the ground. The second morning, I could barely move without my back freezing up. I’ve had back pain on and off over the years, but it was mostly manageable.
This was so bad that despite trips to the chiropractor and physical therapist, I struggled to function for 6 weeks. After x-rays, I learned that I have scoliosis and one of my legs is 2 cm shorter than the other. I could barely get out of bed. Things were fine if I was standing and walking for a while, but if I sat for any amount of time, I couldn’t move. Sitting in a plane for a 2 hour flying lesson was brutal.
At the end of the summer, I finally put a 1cm lift in all of my left shoes and it took care of the issue. I still had a lot of hip and leg pain as my muscles and ligaments adjusted, but it felt so good to have a solution. Now, I stretch regularly and have a personal trainer who makes sure my form stays perfect.
They say “a sick man only wants one thing”, and I definitely experienced that this summer. I’m so grateful to be back to lifting weights, playing volleyball, and being active.
For the first time in my life, I took a sabbatical! I spent the month of July camping, backpacking, visiting family in Wisconsin, taking flying lessons, and just living life on the farm. The back pain started in the second week, so I had a much more challenging time and cut out a lot of things I had planned, but it was still really good.
Though four weeks goes by really quickly! At the end, I felt well rested and eager to get back to work. I don’t plan to take a sabbatical in 2024, but I think I will again in 2025.
Other than the back pain, I’ve had a really good year for fitness. I’ve worked out twice a week for the last few years, but starting in March, I hired a personal trainer. I should have done it much earlier. With the same amount of time spent I’m getting significantly better results.
I stepped on the scale the other day and I weighed 200 lbs. The first time in my life seeing a 2 as the leading digit there… After comparing to some measurements I have from 4 years ago, I’ve definitely put on a lot of muscle as well as fat. Now, I want to slim down a bit to 185 lbs.
We also joined the local indoor climbing gym and have been going once or twice a week. It’s fun to see a lot of progress and the kids are really enjoying it.
Our farm continued to be a big source of joy. Here’s a short version of what we did:
- Planted a big garden and had the usual animals (goats, chickens, and pigs). Though the pigs were a pain and did everything they could to escape their pens this year.
- Built a playground for the kids (I was going to design and build something custom, but I’m glad I just pulled the trigger on a kit—that was enough work).
- Built out a woodworking shop in the 3rd bay of the garage. Now it’s fully separate from the rest of our garage and has a finished dust collection system.
- Landscaped the berm that separates our property from the main road.
- Built a new patio, pergola, and fire pit that our airbnb guests can use.
- Finished the paths on the far side of the creek and planted a dozen more trees.
This year, we didn’t have a manager for the farm and it was a lot of work to keep up on maintenance. We really need to hire a farm manager early in 2024.
August has talked for years about wanting to sell his woodworking and this year he made it happen! We spent a few weeks in the shop making Idaho plaques, cutting boards, and assorted other projects.
Then he set up a stand out on the road by our house. I think it looks pretty good!
If he is more interested in it this summer, we’ll find a craft event or farmers market he can sell his wares at. But that will require making a lot more inventory than he did this year.
All three boys are growing up really well. Oliver (12) loves sports and has been playing flag football, soccer, and volleyball. August (9) is more into projects and business ideas. He and I are always building something together. Josiah just turned four and is rambunctious, kind, stubborn, and curious all at the same time.
This next year, I plan to find a trip we can go on just the four of us to give Hilary more time at home to focus on the garden and the things she enjoys on the farm.
I traveled a lot more this year. I counted 22 trips (including a couple weekends in the mountains) up from 12 last year.
Here’s the quick breakdown.
- Mastermind Talks Conference in Costa Rica — This is one of my favorite events each year. I taught a workshop about ConvertKit’s compensation method which was really well received.
- Team retreat in Puerto Vallarta — This was a fantastic retreat with the team. Hilary came down for the 10 year anniversary celebration for ConvertKit and we stayed for a few days afterwards.
- Family sailing trip in British Virgin Islands — This was our big family vacation. We chartered a flight, went with friends, and had an amazing time. Definitely a life highlight! More below.
- Tastemakers in Chicago — This is an event focused on creators in the food industry. We have so many creators there as customers. It was fun to have breakfast with Rebekah who founded Flodesk. We’ve both bootstrapped our companies and even though we are competitors, it was fun to get to know each other and share notes on the journey.
- Phoenix for the Eras Tour — Back in 2019, Hilary and I did a trip to Phoenix for our 10th anniversary… and to see the first show of the Reputation tour. 4 years later we were back to kick off the Eras tour. Unfortunately Hilary got a migraine right as we were pulling up to the stadium and so I took her back to the hotel. After she went to sleep, I hurried back to the concert (I’m a much bigger Taylor fan than she is) and went with my friend Joshua Becker.
- Mastermind in Cabo — My new friend Matt Schnuck hosted a group of us at a mastermind at his place in Cabo in March and it was fantastic. I already knew a few attendees really well (Sahil and Nick) and was thrilled to get to know Matt, Romeen, Xavier, Sieva, and Kurtis better.
- Cleveland for The Creator Economy Expo — This was a great event for us as a sponsor because of how integrated we are in the community.
- Hiking at City of Rocks — We went with family to City of Rocks in Southeastern Idaho. It’s such an epic place for camping, hiking, and climbing. Though I’m scared of heights and the kids being near the cliffs (they are fearless) made me very uncomfortable.
- Cerro Gordo owners weekend — We got most of the owners of Cerro Gordo together for a weekend. It was fun to meet everyone I hadn’t met before and to walk through the framed hotel. It’s been a long journey, but I’m really proud to be a part of it!
- Family camping trip to McCall — Always a good time hiking, swimming, and riding bikes. It’s great having such an amazing resort town just a few hours away.
- Backpacking with the kids — We were supposed to do backpacking trips this summer, but after this one crippled my back, we didn’t do any more.
- Wisconsin for a family vacation — Hilary’s sister is going to school in Madison, so we took a trip out to see her. Madison is a great city! We especially loved going up to spend the weekend in Door County.
- Team retreat in Paris — For years, we’ve talked about doing a team retreat in Europe since we have 15 team members based there. This year, we finally made it happen with a beautiful chateau just outside Paris. It was incredible.
- Lake Tahoe for my brothers wedding — My oldest brother got married! We flew down to Lake Tahoe and drove to Downieville where he and his wife Autumn live. She’s amazing and we’re thrilled to have a new family member.
- NYC — First stop of the podcast tour. Lots of meetings with creators and we kicked the tour off with a bang.
- Nashville — Our next tour stop and probably my favorite mastermind of the trip. Tim Grahl taught a great workshop on setting your 3-year strategy as a creator. I’m excited for him to teach it again at Craft + Commerce.
- Camping at City of Rocks (again) — Hilary wanted a break and our good friends were going, so I took the three boys solo. We had a great time!
- Atlanta + New Orleans — Mo Bunnell and Shawn Blanc hosted an excellent mastermind in Atlanta on Mo’s farm. Then I went over to New Orleans for a live episode at Fincon. We did it on the main stage in front of an audience of 1,000+ people, which was pretty wild!
- Austin + LA — This was probably the busiest week of my career. I recorded a ton of podcasts, met with so many friends and creators, taught two masterminds, two live recordings, and talked to hundreds of attendees. So fun (and so tiring)!
- NYC + Charleston — I started with a quick meeting with our growth leadership team in NYC, then down to Charleston for a mastermind with 25 of the best marketers in the business.
With a final trip to the mountain house during the Christmas break, that capped off a very busy year. But I loved nearly every bit of it.
Family Sailing Trip
Our family sailing trip was my highlight of the year. I captained a 50-foot catamaran in the British Virgin Islands with Hilary’s brother Daniel as first mate. We went with our friends Luke and Erin Bechtal and their three kids. Hilary’s parents flew with us down to St Thomas since we had room on the chartered flight, then they did their own thing for a week while we went sailing.
We sailed through storms, snorkeled amazing reefs, dropped a boat hook and had to fish it off the ocean floor 35 feet deep, and managed to keep the boat and everyone on it safe.
It was a full boat with 5 adults and 6 kids, but we all had a great time. The 50-foot catamarans are definitely a lot larger than the 40- and 45-foot catamarans I’ve sailed before. Overall I found the extra space to be really nice and not too cumbersome to sail.
The sketchiest time on the boat was our last night anchored on Jost Van Dyke in what seemed like a very protected bay. But the winds picked up to over 30 miles an hour and we started dragging our anchor. Because I was worried about that happening, we had put out a second anchor and plenty of chain, but the two of them combined didn’t hold in the wind.
I woke up at 5am to the sound of the chain dragging and hurried to get the engines on before we swung into another boat. Since we needed to return the boat and get back to US customs, I decided to just pick up the anchors and head out early.
Sailing is fantastic and I’m a little bummed to not have a trip planned yet for 2024. Maybe in the late fall?
I’ve always wanted to be a rockstar. Not actually, but I do think it’s cool to travel from city to city and meet fans and create great content. So that’s exactly what Rachel and I did with the Billion Dollar Creator podcast tour.
We hosted events in five different cities (New York City, Nashville, New Orleans, Austin, and Los Angeles).
It was amazing to meet so many fans in person. In addition to recording an episode of the podcast live on stage, we also hosted masterminds in each city. Those were especially great.
The lesson I learned is: choose yourself. Normally, a podcast tour is something you’d do when you’re well into hosting a show. But we decided to launch the show with a tour in order to really drive growth and stand out from the beginning.
The week we did Austin and Los Angeles was definitely the busiest week of my year. I wrote a bit about it here.
Reviewing 2023 goals
- Learn to ski — Done! I still consider myself beginner to intermediate, but I can do powder and black diamonds through the trees. I want to get a lot better in 2024, but so far we’re having a terrible snow year.
- Get my private pilot’s license — So close! I’ve met all my requirements and just need to finish studying and take my check ride.
- Run a 5k in 21 minutes — I got injured this year and running fell by the wayside. I still competed in the ConvertKit 5k, but my time slipped all the way to 26:26, which is a long way from my personal best of 21:50.
- Go sailing twice — We went on one epic sailing vacation! I didn’t make a second one happen.
- Grow my personal audience — My goals were Twitter 200k (actual: 125k), LinkedIn 100k (actual: 25k), newsletter 40k subscribers (actual: 40,900). Creator Network drove a substantial portion of my list growth.
- Be a lot less stressed — I give myself 50% credit here. I think I am able to take on significantly more than before without increasing my stress, but I’m still a long ways from where I hoped I’d be. Though I did take a sabbatical this year!
All in all, I give myself 100% on skiing, 90% on a pilots license, 0% on the 5k, 50% on sailing, 40% on audience growth, and 50% on stress. So that’s… 55%. Not great, but I’m still really proud of the progress I made. Particularly on my pilots license. I was reading my journal from the last few years and learning to fly was always something that I aspired to but never felt like I could make happen.
Looking ahead to 2024
2024 will be the year of the flywheel. I spent 2023 refining systems for other people and testing theories. This year I’m implementing them everywhere in my business and life.
The three main flywheels I want to implement are:
- Polishing my content flywheel. There’s a single flywheel that drives my podcast, newsletter, and content, but it’s not running smoothly right now.
- Social content flywheel for ConvertKit
- Affiliate + workshop flywheel
Beyond focusing the theme on flywheels, I have six more goals for 2024:
- Finish my book — I have ideas for five books and had I stayed on top of writing, I could have published one a year the last five years. This year I’m creating the systems (daily writing) and getting the support (I’ve enlisted coaching from my friends Kara and Tim) so it’s finally happening.
- Fitness — I have two fitness goals 1) run a 21 minute 5k and 2) dop down to 185 lbs while increasing muscle. Working out with a trainer twice a week has gone really well so I plan to keep doing that.
- Get my private pilot license and instrument rating — I’ll take my private pilot check ride in February or March and then I plan to start working on my instrument rating.
- Host an entrepreneur gathering on the farm — I’ve wanted to do this for years and still haven’t made it happen. Now I’ve got the farm ready to host people. I plan to host a small mastermind and then a larger gathering with a few founders and their families.
- Grow ConvertKit to $53 million in annual revenue — We ended 2023 at $41 million across all of our business units. My goal is to grow our subscription revenue 25% to $47.8 million and then have an additional $5.2 million in our network businesses.
- Consistently exceed 100% net dollar retention — The holy grail in SaaS! We’ve been so close and I think 2024 is the year we can consistently stay above 100% net dollar retention. That means building the best possible product and driving as much revenue and growth for creators.
That’s it! 2023 was a great year and I’m excited for 2024. As I write this, Hilary and I are about to land in Puerto Rico for our first trip of the year. Mostly vacation, with a couple conference talks thrown in there for fun.