6 Jan

2016 in Review — The year I became a CEO

My last few year-in-review posts have been written as “x years after [life change].” 2 years after I quit my job. 1 year after I quit blogging. 

And 2016 seems to be one of the biggest years of change I’ve ever had. Not because I made a different decision or some event happened, but instead because my job changed (again) and I really changed as a person.

2016 is the year I became a CEO.

Not in a slightly lame way like being the CEO of a one person consulting company, but I mean transitioning to leading a real company.

ConvertKit turned four a couple days ago and for the first three years my title was “Founder and Designer.” Officially I was the CEO, but I felt weird adopting that title. I didn’t feel or act like a CEO. Besides, c-level titles seem weird in 5 person companies.

Disclaimer: At this point it’s probably important to remind you—as I do every year—that these year end reviews are written for me, not you. So if this comes across as bragging or overly celebrating my own accomplishments, deal with it. It’s my journal to look back on a snapshot of my progress and mindset at a certain time (you can read my past reviews here). So with that disclaimer, let’s move on.

The moment

The first moment in the company that really felt different was at our team retreat in August. I had brought our entire team of 21 people from around the world to McCall, Idaho for a few days to meet each other and plan for the rest of the year.

The first night in our lodge I gathered everyone in the living room and said tonight was tonight was for celebrating what we’d accomplished.

Then I asked everyone to start sharing specifics to celebrate:

  • “Sending 100 million emails in a single month.”
  • “Supporting 5,000+ customers.”
  • “Getting profitable.”

The list continued. There was a ton to celebrate.

As a way to thank everyone for their work this last year Ashley (our director of operations) and I had done some shopping. So we handed out individually wrapped presents to each person on the team. Everyone was really surprised that each gift was personal. A few people even cried. It was awesome.

Ash and I had made notes from conversations in Slack (that’s how we knew to buy Nicole a waffle maker), browsed Pinterest for style suggestions, purchased from our favorite designers, and relied heavily on Huckberry for everything else.

As everyone showed off their gifts the organized group devolved (also, the fresh chocolate chip cookies Val made came out of the oven). After a few minutes of gathering everyone together again I did my best attempt a Steve Jobs, “but wait, there’s more.”

You see our biggest accomplishment up until that point was to turn the company around from losing money in January to a 50% profit in July. And it was time to share that profit with the team.

I handed out cards to each person. Inside was a handwritten note from each of the directors along with the exact dollar amount of their profit sharing bonus. The bonuses worked out to just over $800 for each month someone had been with the company. So the newest team members who just joined received $1,200+ and the veterans got well over $10,000.

Quite a few people cried. Even more said they didn’t think they would cried until they saw the person across from them start to tear up.

That’s the moment I felt like a CEO. Not just a CEO, more specifically, I felt like a leader.

Sure, I still have no idea what I’m doing half the time and I still make dumb mistakes, but I led the company to this point and all these brilliant people trust me to take us to the next level.

It’s exciting, very challenging, and definitely stressful. But I wouldn’t change it for anything.


Learning to change my role

Earlier in the year my day-to-day work involved working on growth, meeting with the team, designing new features, troubleshooting bugs, and just about everything else. Early in the year I became a bottleneck in so many decisions and processes that my leadership team finally called me out on it.

As the only designer in the company I was spending too much of my time on design and not on company-wide issues. Or when I’d get focused somewhere else I’d hold up the engineering team since they needed designs I couldn’t provide. So the directors team challenged me to not design anything for the entire month of June.

First, I panicked a bit. But someone had to design! We couldn’t live without a designer.

“Okay, then I’ll just hire a designer!”

Easy. Done. If I wasn’t able to design I had to get someone on the team who could still execute on my product vision. Obviously this is what my leadership team wanted. More time spent setting strategy and getting the right people in place and less time doing the hands-on work.

Lesson learned. From then on I’ve worked hard to not be the bottleneck, though it’s a long process and I’m still far too involved. But we’re trending in the right direction.


At the end of 2014 I stopped focusing on my training business (books and courses on software design and online marketing) to go all-in on ConvertKit. You can read last year’s review to see how that went (short version: it was a good decision).

Those products continued to bring in $117,394 in 2015, mostly coasting on work I’d done the previous year. In 2016, unfortunately, that momentum ran out. Total revenue from books and courses was only $23,633. A far cry from the $299,088 back in 2014.

Revenue from all books and courses in 2016

Revenue from all books and courses in 2016

I did bring in another $30-40k from affiliate deals and other small promotions. Soon I’ll finish the books for the year to know the exact amount. From this I learned two things:

  • If you neglect a product or revenue stream it will dry up. Always.
  • If you have an audience there are plenty of ways to make money. Sometimes even a simple affiliate email can result in $20,000 or more in revenue! Pro tip: build an audience.

The good news is I didn’t waste a minute thinking about this drop in revenue, because I had bigger things to worry about (and celebrate): ConvertKit.

The rocket ship

In previous posts I’ve talked about the wild-ride that ConvertKit has been. From a quick-start, to nearly shutting it down, to turning it into one of the fastest growing software companies.

At the beginning of the year we had $98,000 in monthly recurring revenue (MRR) and $50,000 of cash in the bank (less than a month’s expenses!).

We closed out the year with $518,000 in MRR and over $1 million in profit for the year!


Our goals were even higher, but growth slowed later in the year. Still, I’ll never complain about growing over 5x in a single year!


We started 2016 with 6 full-time team members and ended the year with 24. I would have thought that kind of growth would be overwhelming, but it ended up being about the right pace for us. That surprised me since I resisted hiring a team for my books and courses business for so long.

The difference is that I don’t like having high fixed expenses (a lot of salaries) with a variable income (as is common in a launch-driven business model), but with ConvertKit it’s all recurring and predictable. We make more money than the last month every single month, without fail. So growing a team doesn’t add any financial stress.

I’m really excited to hang out with everyone again in a few weeks at our team retreat in San Diego.


Travel continues to be one of my favorite ways to spend time and I got to do plenty of travel in 2016. The highlight being a month long-trip to visit family members in Chiang Mai Thailand. We rented one apartment for the entire time, learned to drive on the other side of the road, and had time to establish our own set of favorite restaurants.


Locations visited:

  • San Francisco for SaaStr Annual
  • Portland for meetings
  • Breckenridge, Colorado for a friend’s bachelor party
  • Las Vegas for Microconf
  • San Diego for a mastermind retreat, then again a week later for social media marketing world
  • Atlanta for a friend’s wedding
  • Oakland for Hustlecon
  • Philadelphia for BaconBiz
  • Stockholm, Sweden for the Double Your Freelancing conference
  • Napa, California for a cousins wedding
  • Boulder, Colorado for the two12 conference, then again a month later for the correct dates (it’s a long story)
  • Portland for The World Domination Summit
  • Austin for SumoCon
  • Nashville for Tribe Conference
  • Chiang Mai for vacation
  • Langkawi, Malaysia for a quick weekend beach trip
  • Bangkok to speak at DCBKK
  • Austin for seanwes conference
  • Sonoma for a mastermind retreat

Only 20 trips for the year! No wonder Hilary thinks I travel a lot…

Besides Thailand one of my other favorite highlights was our mastermind retreat to Sonoma. It was our fourth retreat, but the first one that we invited spouses. Us guys have been close friends for years, but some of our spouses had never met, so we weren’t sure how much fun everyone would have for a weekend in wine-country. Turns out, they all love each other!

They said that each time in the future we go away for a mastermind retreat they plan to all gather in another city without us.

The only downside was all our luggage getting stolen in San Francisco, but that’s a story for another time.



I spoke at six conferences this year which allowed me the opportunity to give the same talk four different times. This was a game changer. By editing and reworking the same talk I got quite a bit more comfortable, tweaked the stories, and most importantly, worked on my jokes.


There was one joke that was getting a good laugh, so the next time I decided to play it up more. Even more laughs. This last time I made it really awkward and long by turning my back to the audience and slowly walking to the back of the stage. It worked perfectly and the audience laughed like crazy.

Writing a new talk each time is a great way to give a mediocre talk. Without repeating the same talk I never would have been able to practice and improve those moments. I’m excited to keep practicing public speaking and be able to refine all of my stories.

If you run a conference on marketing or business I’d love to come and speak.

The best decision I made all year

With that click-bait title I’m sure you want to keep reading, right?


The best decision I made all year was to go to counseling. 

For years I’ve fought with depression. and at the end of 2015 I started going to counseling and continued for all of the last year. It had a huge impact.

If you’re out there looking for life hacks or little tricks to make your life better, try talking through your issues and concerns every couple weeks with a professional. It made a world of difference for me.

I hope the negative stigma around going to counseling continues to decrease.


This year hasn’t been a great year for fitness. I was in decent shape before I went to Thailand for a month and stopped going to the gym. Then I started a habit of doing pushups every day, but that dropped off after I got sick a month in. Basically, all the usual problems when forming habits.

I have been consistently playing indoor soccer, which is a lot of fun. I’m still not good, but I have seen a lot of improvement this year. Starting next week I’ll be on four different teams, so I should be playing at least 2-3 times a week!

Now I just need to practice consistently to improve my footwork.

Good & Bad

What went well

  • Company growth. Can’t complain about passing half a million a month in revenue!
  • Travel. I loved the amount of travel we did this last year. Can’t wait to keep it up in 2017. Staying in one country for an entire month has been a goal for a while, so it felt good to be in Thailand for that long.
  • Emotional health. This year I spent plenty of time working through core issues with family and it made a huge difference. Like I mentioned earlier, counseling is highly recommended.
  • Speaking. Giving the same talk multiple times was a great move. I want to do more speaking (at new events) in 2017.
  • Woodworking. I didn’t mention this earlier, but I continued to build new projects and learn new skills. I have a few new tools that I can’t wait to try this next year.
  • Meetups. In the second half of the year we held ConvertKit customer meetups in over a dozen different cities! These were a huge success and I’m excited to do a lot more.

What did not go well

  • Fitness. This year I tried a bunch of times, but always broke my habits and didn’t stay consistent.
  • Working while traveling. Working from Thailand was a lot harder than I expected. I regularly worked from 9pm to 2am, which took it’s toll. Also my team is still pretty dependent on me, so they were all really happy when I came back. I want to get a lot better about that in 2017.
  • Writing. This is the first blog post I’ve published since July. Ouch.
  • Photos. Quite minor, but we didn’t take many quality photos this year. I relied on my phone instead of a DSLR and I miss having more great photos.

Goals for 2017

  • Host a conference.
  • Cross $1,000,000 in monthly revenue.
  • Take a solo international trip.
  • Redesign this site.
  • Write 12 blog posts (even one a month is better than what I’ve been doing).
  • Practice soccer 4+ times per week.
  • Launch a massive new (secret) project.
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46 Responses to “2016 in Review — The year I became a CEO”

  1. Nathan Clark says:

    Always love seeing these years in review, Nathan. Great to see ConvertKit on the trajectory it’s on.

  2. Congratulations Nathan! You are the inspiration! All the best for 2017!

  3. Love seeing recaps like this! Can’t wait to see what you’re up to for 2017 ??

  4. I love the honesty of this. I’m super pleased ConvertKit is doing really well. It’s a truly great story. Perhaps more importantly, the fact that you’ve kept so many other areas of your life in great shape too is fantastic. You said your health suffered a little from your goals but in every other area you did brilliantly. Very much an inspiration. Thanks Nathan.

  5. Thanks for opening up your life, business, and being honest about success and failures. I’ve quietly enjoyed your work for several years, and can’t wait to see what’s on the horizon. Perhaps we’ll meet at this year’s conference? ;) All the best to you and your team, Nathan.

  6. I enjoyed reading your frank look at a year of ups and downs. I’m glad it was mostly ups for you and your beautiful family!

  7. Congrats Nathan on a stellar year!

  8. Thanks for always sharing as you go and being open. You’re an inspiration to us all! It’s been incredible following the journey, and I know it’s just the beginning.

  9. So happy I was able to meet you in person. It’s been great reading through your blog, and seeing your growth. An inspiration indeed.

  10. Congrats on a growth-filled year Nathan, both personally and professionally. Appreciate all that you and the ConvertKit team do to build up and encourage this community. Best wishes in 2017!

  11. Cory Miller says:

    Really incredible, Nathan! Cheering you and your team on for this next year. If anyone can do it, you can.

  12. Hi Nathan,
    being open about depression and counselling is courageous and so needed in this world. Thank you for choosing to be vulnerable yet strong about this!
    I’m on a similar path with both and can only commend you for drawing people’s attention to their mental health.

  13. Awesome post man. It’s really cool to see what you’ve been up to this year! Best of luck in 2017!

  14. Hearing about you sharing profits with employees almost made me cry! So awesome.

    Love knowing that the dollars I spend with ConvertKit are being invested in the lives of multiple people!

  15. Emile Ackbarali says:

    Thanks for keeping it real Nathan and being open about the ups and downs. It helps remind me that I am not alone on the bumpy road that is entrepreneurship. All the best for 2017.

  16. Always enjoy reading these; inspirational and thought-provoking. Thanks for being so open and transparent as you share the ups and downs of your journey!

  17. Great stuff man! Congrats of the growth. Have always been inspired by your transparency and honesty.

  18. Yeah…pretty much awesome. Thanks for being willing to share all of this Nathan. ConvertKit was the first investment I made into my own business, and it is GREAT to see it grow, and to see your roll change/grow/develop.

    So very proud to say that the team at ConvertKit is part of my team!

  19. Thank you so much for sharing! I was diagnosed with depression at age 13 and counseling has been the best thing that’s ever happened to me.

    Congrats on ConvertKit and all its success :) I love everything about CK – the software, the team, the growth. Keep going!! <3

  20. An inspiration Nathan and huge covertkit fan so thank you!

  21. Excellent year!

  22. I love these year in review posts! I have been following you since last year so I’ve read 2015 and 2016 and really enjoy seeing your progress and reflection on your life. Love that you sought counseling as well! The title CEO seems to come with this “always perfect” connotation and the truth of the matter is that the person behind the title is a normal human being chasing after his dreams, finding purpose, and living life. Sought counseling in 2014 and it was the best decision I ever made! Keep improving yourself, your life, your work, and looking forward to 2017’s year in review! :)

  23. Thank you, thank you, thank you for being awesome! Was fantastic to hear you speak at the Seanwes conference in Austin this year. I’ve enjoyed all the value and transparency you’ve shared over the years. Thanks for being inspirational to do the same.

  24. Nathan, I always look forward to reading your annual review because it’s genuine, honest, and always inspirational. I had no idea about the profit sharing story, that’s incredible! You’re building an incredible company. Keep up the good work.

  25. Nathan,

    I learned about you and Convertkit two months ago and have become a fan. I enjoyed reading you annual review. Doing it like that is a great idea. Which country will you visit for a month this year?

  26. Nathan,
    You are such an inspiration. I have myself struggled with depression. And have attempted to speak (blog) about it but never really found the courage. Good to hear your story. The depression and counseling does not take anything away from you, in fact it adds more respect for you in my mind.

    I love all that you do and especially love your tagline “Teach everything you know”. In fact I am going to go search right not if you sell merchandise with that message. Oh, and I’m also going to call my therapist and setup an appointment.

    Power On!

  27. Congratulations on a great year, and thanks for sharing so openly!!

  28. Katarzyna Krolak-Wyszynska says:

    Thanks for sharing your thoughts and accomplishments! I take some inspirations for myself :)
    Have a great 2017!

  29. I confess. I’m not actually a customer. I can’t even recall how I came to sign up for your updates and I rarely sign up for ANYTHING (email OCD!) but I absolutely love your style. “Inspirational” is wildly over-used, but you are. I’ve read your updates 4 times. I learned so much, thank you. PLEASE blog monthly – I’ll hold you to it ?

  30. Great to hear you are flying, it’s my turn this year I hope you can keep up.

  31. All very inspiring, Nathan. Congratulations. ? I’ve battled off and on with depression since my early 30s. Counseling, yoga, meditation, being in nature more, being more communicative, and good nutrition have all helped me to keep it at bay. It can be tough, I know. With where you are in your business and life, I propose you might be interested in a Vision Day with Rob Berkley http://visionday.com/ He’s a remarkable coach, and works with people like you. My wife and I have had a Vision Day with him and my friends Travis Miller and Jimmy Vee of Gravitational Marketing are his clients of many years.

  32. This was incredible Nathan. Thanks for sharing and for the inspiration.

  33. Looks like a successful year to me Nathan! Congrats!

    Regarding your habits, I recently read “The Power of Habit” which gave a lot of insights on how habits work and how to change or create habits in your own life.

  34. Great recap! I’ve been blown away by Convertkit’s success and have also been struggling with the expansion and hiring of a team. So good to hear when it works out well for a company.

    It was great to meet you at seanwes conference and I’m looking forward to reading more you in 2017. Cheers!

  35. The best takeaway was something I’ve slowly observed over the years:

    “Writing a new talk each time is a great way to give a mediocre talk. Without repeating the same talk I never would have been able to practice and improve those moments.”

    I think that’s the secret that pros know that amateurs don’t. I always assumed every talk had to be brand new and amazing, but there’s usually so little overlap in physical audiences that it makes sense to repeat the same one several times.

  36. Very cool Nathan! Your Thailand pics look awesome. :-) So awesome to see you take the time to travel and be generous. No matter how busy you get. Thanks!

  37. Thank you for all your hard work! 2016 was a great year for you! I can’t wait to see how 2017 goes!

  38. Paritosh Praharaj says:

    Hey, you wrote about this post being coming out as if you are bragging. Not necessarily so. To me it comes out as motivation and drive to do better work in my field. I have read your book on software design and loved it. I don’t think you need to mention about the bragging part. Smiles:)

  39. Amazing story there Nathan, very inspiring! Thanks for sharing.

  40. Beautiful, man. Here’s to 2017!

  41. Killing it. Well done! Now do some pushups.

  42. This was incredible Nathan. I enjoyed reading you annual review which gives me a courage and inspirations of a accomplishment. Thank you for sharing and have a happy and success yet to come in 2017.

  43. Wonderful post, Nathan. You share so much of your life and journey so freely – and that in itself is an inspiration. Thank you for leadership and the amazing team you’ve built. Last year, I became a client of ConvertKit, then fell in love with CK and eventually changed my career track because of it – from running a personal development site to teaching email marketing with Convertkit! I am a ConvertKitty and so happy to be part of the CK extended family! Thank you! Thank you! Thank you!

  44. You grew Convertkit 5x (and a bit more), just like planned!

  45. Steve K says:

    Been following this dude since 2012! Keep it up, very encouraging to me as an entrepreneur – thanks much!!!

  46. I’ve enjoyed reading your updates for a couple of years, Nathan! You’ve really inspired me to start sharing my review publicly as well. Can we expect another Year In Review at the end the month?

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