When I look back on 2024, I feel like I have to pinch myself to wake up from a dream. I knew it would be a big year, but I didn’t expect that so many of my long-term dreams could come to life in a single year. Including buying a 3 letter .com domain name, becoming a pilot, rebranding my company, launching an app store, and so much more.

For more than a decade, I’ve been writing these annual reviews and, as I say every year, this is more for me than for you. I love being able to look back and see what happened year to year. But also I get lovely notes from people who enjoy reading them, even those who I meet at conferences who then say they stayed up way too late reading a bunch of them (Hi Nicole!).

So without further ado, here are the highlights of my life and work in 2024.

ConvertKit → Kit

For almost 12 years, I’ve been building a little software company called ConvertKit to help creators earn a living. In that time it’s grown from a side project to a $45 million per year platform that powers the world’s biggest creators. We’re used by everyone from Andrew Huberman, to Jenna Kutcher, to James Clear, and 60,000 other paying creators (as well as over 500,000 free users).

I’m so proud of what we’ve built, but I always felt like our name was holding us back. We do so much more than help creators convert their audience, and a lot of creators were turned off by ConvertKit as a name since they were there to provide substantial value, not just convert fans to customers.

I tried to rebrand the company to a different name in 2018, but failed through some big missteps (you can read about that here). I felt like we had used up our one chance to rebrand, except for one name: Kit. There’s a long tradition of companies simplifying names as they reach scale. TheFacebook to Facebook, TransferWise to Wise, etc. We knew that going from ConvertKit to Kit would be a much simpler transition than a completely new name. But we also knew that we’d only do it if we could get Kit.com.

The domain

It’s kind of crazy to imagine that the future of renaming the company—if we were going to do it—came down to acquiring a single domain. Convincing one person (or company) to part with an insanely valuable asset. Well, it happened. I’ll write a full post about the timeline later, but for now I’ll just say this:

I can’t say how much we’ve paid, so for now let’s just say that if you’re not in the industry you’ll be shocked at how much it was—unless you’re in the domain industry, then you’ll also be shocked, but at what a great price we got on an English word 3-letter .com.

When we had an opportunity to buy the domain I thought long and hard about it. Now, almost a year later with the benefit of hindsight, I’d buy it again in a heartbeat.

Announcing to the team

At our team retreat in February we owned Kit.com, but only the executives and a select few people knew. Charli, our creative director, and I planned a presentation about our mission and vision and where the company was heading. We teased the need for a rebrand, but then pulled back and shared how much we’ve grown since 2018 as ConvertKit, then dove into our much bigger vision. 

It was really fun (and maybe a little mean) to watch the team’s faces as they thought, “Wait, are they about to announce a new name? Oh, I guess not… Wait…are they?”

Overall the team was really energized about the announcement, but with a ton of questions about implementation details. 

Rebranding in public

When we failed to rebrand in 2018, we kept it totally secret, then made a big announcement all at once. With the logo, website, and app all cutting over at the same time we told everyone on stage at Craft + Commerce. That meant we couldn’t really research or get feedback from our community. I think that was a huge part of the mistakes we made.

So this time we did something entirely different: we rebranded in public. 

We worked with a small group of creators for a lot of feedback, then in June at Craft + Commerce we announced the name change, but not a new logo and brand. We were going to include creators in that. 

Then from June to October, we gathered research, involved the community, refined our messaging, designed a ton of iterations, and more. It was such a collaborative process with all creators. My favorite part is that our brand team created a documentary along the way.

I’d see interactions online where a creator would say, “Why is ConvertKit rebranding?” occasionally followed by a confused or negative comment.” But then another customer would reply and say “Did you see episode X of their rebrand series? It explains it really well.”

Then we had creators asking when the next episode would come out. If you haven’t seen it yet, you can watch the whole series yourself here.

The launch

Originally we planned to launch September 15th, but we needed a little more time for the app redesign and SEO, so we pushed it back to October 1st. 

Speaking of SEO, that was the biggest reason people gave for why our name change was a bad idea. Citing WooCommerce moving to Woo.com (and then rolling it back), they said our traffic would plummet and it was foolish to rebrand. After talking to Collin who leads SEO at Kit and a ton of industry experts, we became convinced that we would take an initial hit, but then be able to recover. But that’s only if we executed a flawless transition. 

We hired another search firm (Relevance.com) owned by my friend John Hall to be a second set of eyes and provide advice on the migration. The entire migration went really smoothly. We saw the expected 20% drop in search traffic but organic search traffic fully recovered and performed at 108% to baseline to close out the year.

The best part of all? We kept the momentum up in every other part of the business, shipping an average of a new feature each week, all year. 

Free plan

Inflation has been the big economic story the last few years and all of our competitors have raised prices in response. But we’ve held firm with the same pricing we’ve had for nearly 10 years.

When we announced the rebrand to Kit, a common complaint was that it would come with a price increase. But instead we did the opposite and cut prices by making our free plan 10x more valuable. We:

• Increased the free subscriber limit from 1,000 to 10,000 
• Added automations to the free plan
• Added Creator Network to the free plan

The response has been wild. We now see organic recommendations of Kit up substantially. 

I’ve always admired Figma’s strategy of great engineering, combined with a widely open free product, and thriving ecosystem. For the last few years, I’ve been copying that same strategy into Kit. This phase is all about making Kit the obvious choice when you are starting a newsletter. 

Our mission is to help creators earn a living, and now they can do it completely for free with a huge amount of headroom. We’ve seen creators earning well over $10,000 on Kit and still be on our free plan.

Kit App Store

When we teased that we had a huge announcement that would change the company people assumed that was our rebrand: but we meant the Kit App Store. 

This makes Kit extensible by the amazing community of designers, developers, and creators that use it every day. Every creator business is unique, so it makes sense to implement an app store model where you can choose what’s in your Kit. 

This model is proven by the thriving app ecosystems of WordPress, Shopify, and iOS. 

We now have 15+ apps live in the store. A few of my favorites are KitBoard (Kanban style CRM on Kit), Transistor (my favorite podcast hosting platform), Mighty Networks (all the data and content from my community is right there inside the Kit email editor), and SavvyCal (calendar info updates in realtime—even after the email has been sent).

2025 is going to be absolutely huge for the Kit App Store. None of our competitors have anything like it and we’re already hearing creators say that our vision for Kit being the operating system for their creator business was a huge factor in migrating to our platform. 

Kit Studios

In 2018, I pitched our team on a crazy idea: what if we had physical locations where creators could meet up, learn, and create together? They’d be part genius bar, coffeeshop, recording studio, and coworking space. This vision to expand beyond software was part of the reason to move beyond “ConvertKit” as a name. “ConvertKit” worked for a software company, but not for my full vision of the #1 brand serving creators—both online and in the real world..

Business, life, a failed rebrand, a pandemic, and so many other things got in the way of that vision coming to life. But I still had it in the back of my mind. Then at the beginning of 2024 three things happened at once:

1. I decided to level up content creation for my personal brand, which meant I needed a professional level studio.
2. We had acquired Kit.com and were planning the rebrand to Kit—so I finally had a name that worked for physical locations.
3. I realized that a coffeeshop and coworking space were commodities, even if they were focused on creators. But the production studios were completely unique.

That also made it cheaper to operate. Coffeeshops and coworking spaces are expensive to staff and complicated to run. But the studio would just require one team member to manage it.

6 years after the original pitch, I started shopping for real estate. At first we were considering something modest: enough to fit my studio and one other. The rent for that would be about $2,000 per month in downtown Boise. But then I kept finding larger spaces for just 50-100% more. Then we found the dream space: rather than a studio buried in the basement of a creepy building, we had the opportunity for a bright, welcoming space in the ground floor of one of Boise’s nicest buildings. For $4,300 per month we could build 5 studios, a conference room, a large community area, and a green room for getting ready.

Here are some photos:

I’m used to residential real estate where deals move quickly and people are motivated to get things done. Commercial real estate is the opposite. Once we selected a location everything moved like molasses. The broker and landlord were slow to respond, negotiated all the smallest details, and had weird demands. The funniest thing was that they were convinced we were “one of those internet businesses that might fail at any time.”

It took lots of financial documents, tax returns, bank statements, and meetings to convince them that we’d be in business long enough to honor our 5 year lease and that we could afford the monthly payment. At one point we said, “With our current cash on hand, we could pay this monthly lease for more than 100 years without running out of money.”

All of those delays took us to a crazy deadline: we got the keys 29 days before Craft + Commerce. When 300 creators would descend on Boise for our annual conference.

Haley Janicek, who has been a star on the Kit team for 7+ years, took on the project and brought it to life. From hiring the crew to build out the studios, to contractors for the remodel, endless Amazon deliveries directly to her house, and everything else in between.

Dream Studio did an amazing job helping us build the studios themselves (they made an entire behind-the-scenes video covering the whole process).

We spent weekends setting up furniture, moving boxes, finishing the remodel, and whatever else was necessary. We even recruited our kids to help (and they loved it!). 

While I had the original idea for Kit Studios, it was Haley’s vision and insane hard work that created what we have today. 

The response blew us away. Creators were just shocked that ConvertKit—now Kit—would build physical spaces for creators. And make them free.

Did I not mention that part? We built world class video podcast production studios—the kind of places that you pay $200+ an hour to use—and they are free for Kit customers to use. 

Here’s why:

1. We want to have the biggest and best creators using Kit. That comes from recruiting amazing creators (the roster who joined this year blows me away) and developing the creators we have.
2. We want to remove every barrier to creating world class content. We’ve seen plenty of creators fly to Boise, record their entire course in a few days, and then do launches that are a multiple of what they expected to do.
3. And because we can. We spend hundreds of thousands a month on advertising. What if instead we poured more of that back into creators by offering truly unique value? That’s Kit Studios.

From here, we are planning further expansion into more cities. We’re launching Chicago in February 2025 and are planning a 3rd city (just working on lease negotiations). If those go well, we’ll explore additional cities.

Kit Studios will become a network of world class recording studios that you have access to as a Kit customer. So whether you have one in your home city, or you travel in, Kit Studios are there to help you level up your content.

Challenges

It wasn’t smooth sailing this year. Every win was hard fought as we overcome a lot of challenges, including:

• Recruiting a new director of marketing who didn’t work out
• It took longer to scale our ads business than I hoped
• Revenue growth slowed at the end of the year
• We hired a firm, but they weren’t able to get us meaningful traction
• Letting go underperforming team members (I hate that part of the job)
• …and more. Businesses are hard.

Momentum

Kit is moving so fast now that I can’t mention everything, but here are a few more highlights:

• Continued to scale creator network
• Inked a huge partnership to scale our ad network
• Refined and scaled our email editor
• Overhauled the media gallery
• Dozens of quality of life improvements
• Polls
• …and so much more

Another huge shift was how many celebrities joined the platform. Just in the last few months we launched Kit newsletters for Matthew McConaughey, Hasan Minhaj, Ellen Degeneres, Morgan Freeman, and Lil Jon.

It’s really interesting to see how differently we are treated in the world of star creators with the name Kit, compared to ConvertKit. I really believe our old name was holding us back from some of those opportunities.

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Personal brand

This year I decided to get serious about using my personal brand and audience to grow Kit. That meant bringing Kara, my head of marketing, onto the core team at Kit and turning my hobby audience-building work into a core focus.

Podcast

2024 was a great year for the podcast with a rename, 50 episodes, the new studio, and launching  a new podcast YouTube channel and grew it to 7,000 subscribers (please like and subscribe).

Renaming the show

Originally when I launched the show with Rachel Rodgers we focused on creators using attention to build equity, based on my essay called The Billion Dollar Creator. When Rachel stepped down last year to focus on rest and pursuing other ventures, I considered finding another co-host for the podcast. But I ultimately decided that I wanted to have conversations with creators and do more live coaching as a unique angle for the show.

The aim of the show is the same—I’m still focused on creator businesses and leveraging audiences and attention to create wealth. But I wanted a show title that felt a little more approachable. Not everyone is trying to build the next household name, and that’s okay. There’s so much you can learn even if you’re not building a billion-dollar business. Calling the podcast The Nathan Barry Show gives it room to grow and the flexibility for me to have conversations with many different and interesting people.

Recording in-person only

A big pivot this year was to make the rule that I only record the podcast in person. At first I did that because I wanted higher production quality and better chemistry with the guests. But then I found that in addition to those, I just had more fun.

The downside was that what was a 60-90 minute commitment for a virtual recording turned into a half day or more by the time we got to the studio and recorded in person. Then we started batch recording.

Instead of recording one episode per week, we record four episodes every month and make an event out of it and host a dinner for people to connect. In just a day and a half, we have enough episodes for the entire month.

That allowed us to double down on the coaching format, which I think makes for some of the most unique, actionable content in the creator business world.

If you’re not a regular listener, start with one of these episodes:

1. How I’m Launching My $5,000 Course in 4 Steps (Coaching Session)
2. Ex-YouTube Employee on How to Get 100,000 Subscribers FAST
3. How to Make $2,000,000 From Courses and Quit Your 9-To-5

If you’re a creator earning $250,000/yr or more, feel free to apply to be on the podcast.

In 2025, I want to keep doing more of the same with the podcast: steadily producing content I’m proud of. I wrote a newsletter about this (Maybe you’re already doing the right thing), but with the constraints and target audience I have for the show, I think I’m doing exactly what I should be doing and just need to stay consistent.

Creator Flywheels course

I was so inspired when I read Good to Great and heard Jim Collins talk about flywheels, but then I was so disappointed when I couldn’t find any meaningful material on how to implement them. So I spent the last 3 years researching, studying, and creating a curriculum around practical flywheels for creators.

Last year, I taught a bunch of workshops and two cohorts of a course, then this year I polished all that together into the final curriculum and launched the full Creator Flywheels course and group coaching program just before Thanksgiving.

We sold $107,000 in the initial launch, which was great. The community is going well, feedback calls are a ton of fun, and we’re continually expanding the curriculum with practical examples.

In 2025, I want to:

• Build an ads flywheel for the course to really drive ongoing traffic and sales.
• Scale to $1 million in revenue for the course and community.
• Grow my example flywheel library to 50 flywheels you can clone into your business.

Book(s)

One of my biggest goals for 2024 was to finish writing my book—and I didn’t hit it. I started strong and got to a solid outline before realizing the concept wasn’t quite working. I know the book will transform readers’ lives and businesses, but I haven’t yet been able to get the perfect packaging and positioning.

In the fall, I got together with James Clear (we hadn’t hung out in person since before COVID!) to talk through ideas. He loved where the book was headed, but agreed we didn’t have the perfect packaging yet.

He actually pitched me on writing an entirely different book next. Whichever book I write, it will be my first book in over a decade.

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It’s a bit frustrating to write 10,000+ words on a new book and still not really feel any closer to finishing than I did before. I know how to write a good book, but at this point in my career, the bar is so much higher. This isn’t something I want to rush. So I plan to keep working at it until I can deliver something that is truly world class.

Other business ventures

Outside of Kit, I have a few other business ventures:

Paperboy (a newsletter growth agency)

Paperboy had a great year working with clients like Ramit Sethi, Morgan Freeman, Lil Jon, Matthew McConaughey, Chris Donnely, and so many more. We continue to be the growth engine behind so many of the largest newsletters on the web.

Not only are we delivering really solid growth for clients, but we’re also producing quite a lot of cashflow (well over $100k distributed to me in 2024). 

Short-term Rentals

It was a rough year for our short-term rental business:

• I owned a duplex with a friend and that partnership fell apart. I had to buy him out and then work to fix it up and get it back on the rental market.
• We decided to part ways in our main Airbnb business and are working out a deal to buy out one of our partners.
• We got served with a frivolous personal injury lawsuit and are dealing with that (both in the court system and getting insurance to pay).
• A large water leak resulted in substantial repairs on another duplex.

It’s still a good business in the long-term, but we got dealt an unusually bad hand this year.

From Boise (a local newsletter)

It’s so fun to watch Marissa build From Boise into a sustainable business. She’s hired a small team, grown the newsletter, and continued to grow social. Sponsorships are still the primary revenue source and going strong. 

Fitness

2024 was one of my best years for fitness. I started working out with a personal trainer in March 2023 and have stayed really consistent. Halfway through 2024 I bumped my schedule up to 3 days a week, and am now pretty consistent at 4 days a week at the end of the year.

I ended 2023 weighing 200 lbs and planned to cut to 185 lbs in order to try to get visible abs. I spent the first half of the year learning what worked for me in order to cut weight. Out of everything I tried, what worked the best for me is doing 48 hours fasts every week or every other week. Eating smaller portions or making slightly better decisions is hard for me, but doing something absolute like skipping breakfasts or a 2-day fast is easier.

What worked best is to eat dinner, then eat nothing until dinner two days later. The first time was quite difficult, but each fast after that became progressively easier. 

With fasts and consistent workouts, I dropped from 200 lbs to 187 lbs. But then I decided I cared more about putting on muscle than getting skinny. So for the rest of the year I bulked up (hitting 150-200 grams of protein per day). I stayed moderately lean as I added muscle, until I broke my ankle and had to stop all cardio. 

Breaking my ankle

This fall, I broke my ankle in a city league volleyball game. I went up for a block and the guy hitting on the other side came under the net. I landed on him and went straight to the ground.

The worst part? The score was 1-0 in our first match to 25 points. We were 60 seconds into the game. Also this was the game that Hilary came to watch. Rather than getting to watch me dominate at the net (I’m not actually that good), she got to see me crumple to the floor in pain.

At first I thought I just sprained my ankle, but the next day it was worse so I went in for x-rays and confirmed that there were two small fractures, one on each side, as well as a piece of bone chipped off. Thankfully it didn’t need surgery, but I did need to spend a month wearing a boot.

I stayed consistent at the gym, but was pretty limited in what I could do. My legs got skinnier and my midsection grew. I put on more muscle, but gained fat as well.

The biggest challenge was that a month in the boot really aggravated my scoliosis, and I spent another month with severe back pain. But thankfully the same stretches and movements my PT friend gave me a year ago helped me get back on track.

Now at the end of the year, I’ve put on quite a bit of muscle, but also weigh the most I ever have at 205 lbs. I find the balance of trimming fat while maintaining muscle to be pretty challenging. But that’s the goal for 2025!

My biggest lesson learned is to just stay consistent. I could have easily sat around for a month when I broke my ankle, but instead I didn’t miss a single workout and pushed through.

Family

Oliver turned 13 this year. He’s all the sports, all the time. This spring he played pickleball for the first time and loved it. Over the summer he did a multi-day pickleball camp and became obsessed. Since then he’s played in a few tournaments and done quite well. A highlight for me was him and I playing together in a doubles tournament. Now I just need to keep practicing so he’ll keep playing with me.

August turned 10 and is all about making things and running businesses. We gave him a Ninja Creami for his birthday and he used it to run an ice cream stand in the park. We also got an Xtool laser engraver at the end of the year and he spent so much time with it.

Josiah just turned 5 on New Years Day. He loves playing games (he’s very good at Splendor and Monopoly Deal), gymnastics, and Kid Strong. It’s interesting to watch him try and keep up with his older brothers, and in doing so develop athleticism earlier than they did.

We also got a puppy named Sadie. 

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Farm

This was a quieter year on the farm, though we did a few projects:

• Built a swimming hole / play area in our creek (we plan to level it up in 2025). 
• Buried water and electrical pipes to give easy access in our garden.
• Bought a bigger above ground pool was a lot of fun this summer. Though we couldn’t keep it as warm, so we need to improve that next year.

Since we aren’t renting out our cottage on Airbnb anymore, it was really fun to have more friends stay there. It became a thing for friends to stay on the farm, hang out in Boise, then record an episode on my podcast.

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Travel

While I still did a good number of trips, it was a lighter year for travel than last year. The only family trip we did was spring break in Palm Springs with some good friends of ours. Otherwise it was just camping and little weekend trips.

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Q1

• ROI Summit in Puerto Rico with Hilary. It was nice to mix a business trip with a getaway as a couple.
• Mastermind in Scottsdale. This was with a really fun group of business owners.
• Team retreat in Cancun. This is the retreat where we got to announce the Kit rebrand to the team. So fun!
• Speaking at Babybathwater in Cabo. Such an amazing community. My flywheels talk was really well received.
• Mastermind in Cabo. This was our second year with the same group. I look forward to this every year.
• Palm Springs for Spring Break with the family. August and I flew the three hours down to Palm Springs as my first long-distance flight as a private pilot (without an instructor).

Q2

• NYC and New Haven for documentary filming and speaking at Yale. We were recording the Kit rebrand documentary during the earthquake, so I caught my reaction on video. 
• Portland for Travelcon. I flew my plane in a quick hour and 20 minute flight to Portland. Before heading home I was at a meeting that was going well. The person asked, “when’s your flight? I don’t want to make you late.” That just showed the benefits of flying my own plane: leaving whenever I wanted.
• Columbia, Missouri for Capital Camp. This was my first time and I plan to go again in 2025.
• Camping trip with 4 other families. When you have kids, it’s so much fun to camp with other families with kids.
• Dallas for a waterpark. This is a trip that August planned and it was really fun.

Q3

• Boulder & Fort Collins. My sister-in-law was in town visiting so we took a trip to Colorado for work meetings and to see her friends. Flying across the Rockies was pretty cool.
• Team retreat outside Portland. Another trip to Portland on my plane. This time I made a quick stop outside Seattle to have breakfast with my sister.
• Coeur d’Alene with the kids. This was to escape the smoke (more on that later).
• Las Vegas with James Clear. James and I hadn’t hung out together since before COVID, so we looked at our travel schedules and found a city to rendezvous in. I also got to hang out with Alex Hormozi.
  
  

Q4

• Los Angeles for Tiago’s conference & meetings. It was fun speaking there, recording two episodes with Mark Manson in his studio, and meeting a ton of great creators.
• Mastermind in Atlanta + recording day. Shawn and Mo host a fantastic mastermind. Since there were so many great creators there I stayed an extra day and recorded 4 podcast episodes.
• New York for our board and executive meetings. Dave, Kit’s CRO, has an amazing place in the Catskills where we hosted our exec offsite. 10/10.
• Charleston for a mastermind. Another amazing group of creators.

Based on how the podcast tour went in 2023 I thought we’d do a lot more in-person podcasts, but we only did three: Yale Startup Week, Travelcon in Portland, and in Boise at Craft + Commerce.

After a quieter year of travel in 2024, we’re kicking off a much busier 2025 with a trip to Thailand to spend 12 days with Hilary’s sister.

Flying

Last year, I started flying, soloed, bought a plane, and just missed getting my license before the end of the year. Then after some delays from travel and weather I took my checkride (the last test before you get your license) in March.

The checkride consists of roughly a 2 hour oral exam followed by a 2 hour flight exam. I passed the oral exam just fine, but unfortunately failed the flight exam on my steep turns. It was a bit bumpy that day and I couldn’t maintain the tight tolerances (do a 360 degree turn, at a 45 degree bank angle, maintain your altitude within 100 ft, and roll out within 5 degrees of your starting heading). 

One nice thing is that if you fail a maneuver, you’re able to keep going and try everything else. Then you only have to retest what you missed. I ended up missing the short-field landing as well (I didn’t raise the flaps after touchdown). After some more practice flights I did my checkride retest a week later and easily passed.

Having my license and a fast plane has opened up a whole new world of opportunities. 

Escaping the smoke

This summer Idaho had the worst wildfires we’ve had in decades. The result was the worst air quality in Boise of my entire life. A normal bad year is 4 days with an AQI above 150. The worst year since 2000 was 11 days. In 2025 we had 38 days. 

One weekend in September, I got sick of the smoke and pulled up two charts: how far I could fly in under 90 minutes and the wildfire smoke map. That gave me three great destinations: Bend, Salt Lake City, or Coeur d’Alene. There are fun resorts or hotels I’ve been wanting to visit in each one. Then based on weather forecasts I chose Coeur d’Alene and made a reservation.

Within 2 hours of getting the idea for an overnight trip, I had the kids in the plane and we were on our way for a lake getaway. We had a great time swimming, hiking, and playing pickleball. All in clear air.

There was a thunderstorm that came through Boise, so I decided to stay an extra night. It was great to have the flexibility of remote work and owning my own company to just be able to shift things around the next day.

Tetons with Hilary

Hilary and I did an overnight trip to Driggs, Idaho, which is on the Idaho side of the Tetons. It’s about an hour flight and takes you into a fantastic airport with a great restaurant right there in the FBO. We grabbed our rental car (they deliver it planeside) and went for a hike then had dinner at a brewery with a view of the mountains.

The next morning, Hilary asked two questions: “How far is it to Yellowstone from here?” and “When does Old Faithful erupt?”

Only a 20 minute flight and the geyser would erupt in about 90 minutes. We could make that.

We drove to the airport, did the preflight, and took off. The timing worked out perfectly. We flew 2,000 feet above Old Faithful as it was erupting, then spent another 45 minutes touring the national park. Seeing all the highlights from the air. 

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Hangar remodel

When I bought the plane at the end of 2023, I bought a 30×50 ft hangar as an empty shell. I thought it would be easy to put a bathroom in it (the stubs for plumbing were already there) and add a couch. I didn’t realize how much work it would be to get the permits and to do the whole project.

The biggest surprise was that none of the utilities were actually hooked up (the city had said they were) and so I had another $15,000+ in unexpected expenses for water and sewer hookups.

The project took a full year to complete, but I’m so happy with how it turned out!

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I now have a comfortable, heated place for my passengers to hang out before and after each flight as I take care of the plane. 

One other fun thing I did this year was mount a Starlink Mini in my plane for super fast internet at any altitude. The Cirrus is set up perfectly for it with an upward facing rear window. It’s really great to be able to get updated weather and routing information in realtime. And let’s be honest: it keeps the kids happy when they are watching Netflix in the back seat.

Instrument rating

I’ve had to cancel a couple flights or change plans because of cloudy weather, so getting my instrument rating (so I can fly through clouds) was my big goal for 2024. Unfortunately, I didn’t make as much progress as I’d like. I still have about 10 hours of instrument flying to complete and to finish my written test. Between the kids’ activities, family life, and a very busy year for Kit, I wasn’t able to set aside as much time as I’d like for studying. 

January is really busy, but in February I’m really going to focus on studying for the written test. 

Aviation has become a very rewarding part of my life

Learning to fly and buying a plane have given me a huge amount of flexibility and fun. So many times I’ve thought: “I can’t believe this is my life!” thanks to the epic aviation experiences. 

It’s not all rosy. There are a few downsides of aviation that I hit this year:

• It’s a lot of studying and training. This is hard—as it should be. Just don’t expect that you can pick up flying as an easy way to save time traveling. You’ll spend hundreds of hours to become (and stay) proficient.
• I had a few cancellations because of the weather. Flying a general aviation plane means that you can’t fly high enough to get over weather or icing. So often that means delaying a trip or having a backup commercial flight. Over spring break, we went to Palm Springs but had to leave the plane there and fly Alaska Airlines home because the clouds were full of icing and the tops were higher than my plane can fly.
• My family just isn’t that into it. Everyone enjoys having the plane for where it takes us, but I’m the only one in love with every part of aviation. I’d go and fly just for fun, but my wife and kids only want to go if we are visiting a unique or fun destination. 
• My Cirrus SR22T is a very capable and fast plane, but taking it all the way to Southern California or Phoenix is a big time commitment (3-4 hours of flying). Often it’s better to just fly commercial for work trips if there’s a direct flight. Often at events people ask, “did you fly yourself here” and I have to say, “no, it would take multiple days to fly my little plane from Boise to New York.”
• It’s expensive. Aviation costs me about $100,000 per year. That would be a lot cheaper if I had an older plane and had partners in the plane. 
• There’s a lot of administrative work to own a plane. To cover income tax, liability, FAA regulations, and sales tax requires a lot of documentation and careful setup. I hired the wrong advisors when I bought the plane and had a huge amount of work to clean it up.

I’m now at 235 hours of flight time (still a relatively new pilot) and am just working to steadily build experience each week.

Goals

My biggest goal was to implement flywheels throughout my life and business. This went well, with some really thriving, others took longer to get going.

• Podcast flywheel: going really well. 
• Kit’s social media: going fine, with plenty of ways to improve in 2025
• Affiliate workshop flywheel: started late, but has some really good early momentum going. Who wants to do a workshop in 2025?

Finish my book — Not even close! I made a ton of good momentum, but still can’t figure out the final positioning of the book. I may shift to writing a different one that I already know how to package and position.

Fitness — I didn’t hit either of my fitness goals (run a 21 minute 5k and drop down to 185 lbs while increasing muscle). But I did make a ton of progress and am really happy with where I ended the year.

Get my private pilot license and instrument rating — I got my private pilot license, but am only about halfway to my instrument rating.

Host an entrepreneur gathering on the farm — I didn’t do this. I need to schedule it more in advance and get invites out.

Grow ConvertKit to $53 million in annual revenue — Unfortunately, we didn’t meaningfully grow our network businesses, so we didn’t hit this goal. We ended the year closer to $46 million. 

Consistently exceed 100% net dollar retention — Nope. We bounced right around 99.5% NDR. So close! I’m still determined to hit it in 2025. 

2025 goals

• Fitness — For 2025, my goal is simple: 160 workouts. In other words, stay consistent and work out at least 3 times per week. By combining that with good nutrition I know I’ll get to where I want to be.
• Flying — I’m still just getting started in my flying journey. In 2025, I want to get my instrument rating, take an epic multi-state trip, and fly to the ghost town. It’s criminal that I didn’t make it down in 2024, despite having my own plane where I could get there in under 3 hours.
• Kit — The plan is to grow subscription revenue to over $50M ARR (this is just our subscription business). Then to really get the our Kit App Store and Kit Ad Network thriving. We’ll also close a secondary round to get liquidity for the team (email me if you want to buy shares). In order to help with all of this I am going to recruit an incredible COO.
• Personal brand — The goal is consistency and scale. I will publish 50 podcast episodes, scale top of funnel growth (hit 100,000 followers on LinkedIn), and drive $1 million in flywheels course sales.
• Farm — I want to finish three farm projects this year: our swimming/hangout area by the creek, build a pickleball court, and landscape the rest of our berm.
• Finish my book — I have so many ideas to get out into the world that I need to make consistent progress. Rather than only setting a top line goal to finish my book, the specific leading indicator will be 100 book writing sessions.

A final question

One of my favorite quotes is from Rudyard Kipling: 

“If you want something and don’t get it, there are only two reasons. You either really didn’t want it, or you tried to bargain over the price.”

I’m pretty clear on what I want in life, so where am I bargaining over the price?

1. Writing a book — On an episode of How I Write, Tim Ferriss talked about how there are plenty of mediocre books and so you shouldn’t write one unless you can dedicate at least a full year of your life to it.
   This year I tried to write a book on the side and it didn’t work. Not to say I should only pursue a book if it’s my number 1 focus (as long as I’m CEO of Kit, that will never be the case), but I need to block out a lot more time to bring it to life.
   
2. Fitness — I’m trending in a good direction, I just want to get there faster. If that’s the case, I need to be much more serious about my diet.
   
3. Instrument rating — I need to buckle down and study. If I was more serious about it, I know I could have gotten it done.
   

Really this comes down to focus. My version of bargaining is that I say I can do it all at once. The universe is just like “Okay, let’s see how that works out.” I overcommitted in so many areas in 2024. I’m going to scale back and focus in 2025.

At Kit, I’m working on doing more things in sequence rather than in parallel. I think that’s what I need to do for the rest of my life as well.

2024 was an incredible year. As I said at the start, my dreams came true. So many of you reading this played a role in that and I’m so grateful. Whether you’re a friend, customer, or regularly consume my content: thank you for helping me build this dream life.

Here’s to an epic 2025!