2016 in Review — The year I became a CEO
Life | January 6th, 2017
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 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.
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.
- 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.