2019 in review – A year of balance

Overall 2019 was a really balanced year. I didn’t rebrand the company, launch a massive new project, move to a new house, have a huge amount of stress, or really anything that crazy. I still did a lot, but everything was balanced and the result of having a large, talented team. 

Before we dive in, if you haven’t read any of my past reviews you can check out the the last 8 years (2018, 2017, 2016, 2015, 2014, 2013, 2012, and 2011) in my previous posts.

Family

A new addition!

For years Hilary and I debated whether or not to have more kids. At first we were perfectly content with just two, but over time we started to lean more and more towards trying for a third. We got pregnant last fall, but then lost the baby at 11 weeks. So we’re especially thrilled to welcome a new addition to the family!

Josiah Laurence Barry was born January 1, 2020. What a way to kick off the decade! He’s 6lbs 10oz and 20 inches long. Quite small compared to August, who was 9lbs! Hilary was incredible through the whole labor and birth. Both she and Josiah are doing well.

As I write this I’m a couple weeks into paternity leave and I took a break to head to a coffee shop to help maintain my writing habit. 

The farm

This year on the farm felt like two steps forward, then one back. Last year we got our irrigation system in and turned our back field nice and green. Unfortunately this year our septic system failed and we had to spend $15,000 to build an entirely new system…which tore up a lot of our beautiful field. 

But we did make major progress, particularly on the front of our property. We planted trees down the entire front of our property and cleaned up all the weeds. Then we turned our riding arena into a soccer field.

Fitness

Speaking of soccer, I played just as much soccer as ever. Averaging 2-3 games per week and playing on as many as 4 teams at a time. 

I also made it to the gym fairly consistently and got quite a lot stronger. That combined with intermittent fasting (just skipping breakfast most days) meant that I hit my goal to drop from 196 lbs down to 175 lbs. After some delicious holiday meals I’m up a few pounds, but with solid routines that will come off easily. 

So what finally made a difference? Well, I had a friend put together a workout routine for me so I always knew what I was doing when I went into the gym. Then I found a gym I liked (olympic weights, very few machines, not too busy) a half mile from my house. And finally, cutting down to two meals a day meant that I could slowly and consistently lose fat without putting in any real effort. 

For the first couple weeks it took some willpower to not eat in the mornings, but now I don’t miss it at all. If I feel hungry I just take it as a cue to drink water. Then around 11:30 or noon I eat a meal, which is usually breakfast food (eggs, sausage, fruit, etc) since it’s my favorite meal of the day. 

If you are planning to lose weight in 2020 I highly recommend you try intermittent fasting. 

Travel

1. Oceanside team retreat
2. Hawaii (big island) for our annual family vacation
3. Skiing in Colorado
4. Atlanta for Menfluential
5. Malibu for Wild Ventures
6. NYC with Hilary
7. Cerro Gordo to visit our ghost town
8. Bend for a bachelor party
9. San Francisco for a sailing class
10. Portland for WDS
11. Gatlinburg for a team retreat
12. Vancouver for Barrett’s babymoon
13. Washington DC for Fincon
14. Phoenix for the Inc 5000 conference
15. Cabo for Mastermind Talks
16. Columbus for a keynote, then Nashville for a wedding
17. LA for Disneyland!
18. Portland for our board meeting

Flying to Cerro Gordo

Last year we got the chance to invest in a ghost town in California called Cerro Gordo. We took an 11 hour road trip down to see it in November. This year I wanted to go back and bring family and friends. 

Lone Pine, the small town closest to Cerro Gordo, has a small airstrip that is only a 2 hour flight from Boise. I started talking to charter companies about flying down, but most declined because the FAA lists the runway in poor condition (cracks in the pavement, weeds growing through them, etc) and they didn’t want to charter a flight without scouting it first.

Then I talked to Jackson Jet Center, who have a few Pilatus PC-12s in their fleet. This turboprop plane ended up being perfect for the trip since it has the spacious interior of a small jet, but can handle a short unimproved runway. Our pilot, Thomas, did a lot of research and talked to local pilots about the runway in Lone Pine and decided it would be just fine to fly into. 

This was the perfect trip for chartering a plane as it allowed our group of 9 to visit a difficult to reach location (from Boise) for a quick weekend trip. If I were reading this the first question I’d ask is, “how much did it cost?” So, full disclosure, chartering the plane was $7,000 all in. That included round trip flights from Boise to Lone Pine and keeping the plane in Lone Pine for 3 days. 

Here’s a full vlog episode I recorded from the trip:

Sailing!

One of my goals for the year was to learn to sail. In order to make that happen I took a week long sailing class in San Francisco bay, taught by Hilary’s uncle Ray. I now feel confident to charter a boat myself—though the challenge will be convincing a charter company that I have enough of a sailing resume! I’ve now sailed in the Florida Keys, San Francisco Bay, and the San Juan Islands. 

We’re working on planning a sailing trip in 2020 in order to stay current on our skills.

Watch the full vlog from San Francisco:

Personal Projects & Investments

Tiny house

One of my biggest goals for the year was to build a tiny house. I didn’t get it finished in 2019, but it’s getting really close. This has been such an incredible experience to design and build from scratch. I don’t know when, but sometime I want to build another one (or help a friend build theirs).

Here’s the vlog episode on the tiny house:

Since recording the vlog I’ve finished painting, installed the floor, and started on the finish electrical work. Another month or two of work on nights and weekends and I should have it completed.

Airbnb

I didn’t make the our guest house airbnb a priority this year. I had it blocked off for a lot of time as family was visiting or we just were busy and didn’t feel like hosting guests then. But I was surprised to see even with that we beat last year’s income by $1,000!

Digital products

I said last year was the final time I’d publish numbers for my digital products…but surprisingly they still sold a meaningful amount this year at $9,526! That said I haven’t put any effort into them and with everything else going on I don’t have any plans to change that. 

The latest venture

My good friend Patrick (who I featured in my Ladders of Wealth Creation article) and I have been talking about doing a venture together to remodel a house and run it as an Airbnb. This summer we started to look at properties in Nampa near where he lives (so it would be easy for him to manage). We were looking for anything we could add a second unit to (converting a garage, adding a tiny house, etc). 

We ended up finding a fourplex that was in poor condition, but had a solid structure. Because of some water damage, mold, and needing a new roof, most banks wouldn’t finance it. Conveniently Hilary and I still had the cash from selling our old house a little over a year ago. We were able to use that plus more money from savings to buy the property in cash ($330,000). 

Because this property was more expensive and four units instead of the two we planned for, we brought in Philip and Ashley as well. Along with them we put up the $150,000 necessary to remodel the entire building and furnish four units. 

After 8 weeks we have the first unit fully remodeled and accepting it’s first guests! The plan is to finish the remodel this spring and the refinance to get our cash back out and ready for the next project (perhaps a tiny house hotel?).

Angel investing

This year I invested in Future and Wellnesse. I don’t do much angel investing and plan to keep it limited so I can stay focused on ConvertKit. Though it is fun to have some skin in the game for companies run by friends!

The rest of my investments are performing well, with ManyChat as the top performing company. They raised an $18 million Series A from Bessemer Venture Partners this year. 

I also increased my investment in Cerro Gordo this year. Now I’m the single largest investor. It will still be a while before there is any kind of return there, but the people and project are fantastic. It was also fun to see it featured in Episode 4 of The World According to Jeff Goldblum on Disney+.

ConvertKit

And now on to the main event: ConvertKit! Each of those projects and investments I mentioned earlier take less than 5 hours a week combined. ConvertKit is where I spend 95% of my time and energy. Here are the results from that:

ConvertKit by the numbers

Our annual run rate grew 40.6% from $14 million to just shy of $20 million. Our customer base grew 32.5% from 20,644 to 27,382. And our team grew from 35 to 48 incredible humans. 

We were named the fastest growing software company in the United States by INC Magazine and reached the #23 spot for all companies on the INC 5000 list. 

A few of my favorite highlights

• Our team retreats – As a remote team it is so special when we can get our team together in person. This year we hosted two retreats (our 6th and 7th) in Oceanside, CA and Gatlinburg, TN. As the team grows I always worry about losing the magic of our intimate culture, but since we’ve grown slowly and deliberately each retreat is still special. 
• Craft + Commerce – Ever since I surprised the team by setting a goal of hosting a conference in my 2016 review post, we’ve hosted an annual conference in Boise, Idaho. This was our third year and it was definitely a favorite! Each year the event becomes more polished, has more attendees, is easier to sell out, and loses less money! I’m so excited to welcome 400 creators to Boise again in 2020!
• Meeting Peter Thiel – Thanks to an invite from John Durant from Wild Ventures I was able to meet Peter Thiel at a party at Peter’s house in the Hollywood Hills. Not only was the venue incredible, but I got to meet so many good people for great conversations. The highlight was an in depth conversation with Peter himself on education and homeschooling. 
• Coaching – We hired executive coaches from Reboot for our entire leadership team and it continues to be some of the best money we spend each month. 

Features and product changes

All in on landing pages

At the end of 2018 we made the decision to focus on landing pages and make them a core part of the product. That meant rebuilding our editor from scratch, adding more integrations, and building a ton of templates (we now have over 30 landing page templates for everyone from authors to podcasters to video creators). 

The features include:

• A direct integration with Unsplash to access hundreds of thousands of royalty free photos
• Custom domains for your page
• Thank you pages for building a mini-funnel
• More advanced content formatting tools

We’re already hearing from so many customers that with the product we have they are now able to cancel LeadPages and other landing page platforms to streamline their business (and save money!) to just use ConvertKit for landing pages and email. 

All new email and template editors

In order to provide better formatting options and a beautiful writing experience we wrote a new text editor for broadcasts, sequences, and landing pages. It combines the simplicity of Medium with the power of any other rich text editor. 

We also rebuilt our template editor to enable beautiful email templates. But unlike other platforms we start simple and let you build up from there, rather than forcing you into a complicated template to start and making it difficult to strip it down from there.

Creator Pro

As our large-list customer base has grown over the years (we now host email lists for Tim Ferriss, Gretchen Rubin, Tim McGraw, and many more) we get requests for advanced features that are different from what our normal customers want. In order to serve them better we rolled out a new plan called the Creator Pro add-on. It includes some great new features like a Facebook Ads integration, advanced reporting, a dedicated account manager and more.

My personal favorite feature—which I’ve never seen any email platform do before—is the ability to change a link after an email has been sent. So if you make a mistake and send an email with a broken link, you can fix it after the fact! It’s simple to use and feels like magic when you bail yourself out of an embarrassing mistake!

A new business model

Finally, on the last day of the year, we announced a new business model: ConvertKit is switching to freemium. It’s starting with our landing page product available for free, but then if you invite a friend you can unlock email sending as well. That means thousands of creators will now be able to launch their next creative project completely for free. Then they only have to start paying once they start to get traction!

Freemium is brand new for me, so I’ve been learning from as many articles and conversations as possible. The early numbers from the first week look good and I’m excited to see where this takes us in 2020! As we learn from this first experiment we plan to keep increasing our free offering so that choosing to use ConvertKit over every other email product becomes a no brainer.

In 2020 our goal is to get to 500,000 free users on ConvertKit!

Let’s recap 2019’s goals

• Complete at least 50 weight lifting sessions – Done! I tracked 72 workouts in 2019, so just over 1 per week on average. While not incredible, it’s now a habit! In addition to workouts I played well over 100 soccer games (sometimes as many as 4 per week). 
• Publish 50 blog posts – Not quite… I had a good streak going for the first few months, but unfortunately I broke it and only published sporadically throughout the year. Ending with 29 total posts. But I’m really proud of some of them, especially The Ladders of Wealth Creation.
• Grow ConvertKit to $1.6M MRR – Done! But I really wanted to hit $20M ARR, which is about $60,000 more than this goal. Missed it by $16,000 in MRR. Unfortunate, but we’ll hit it in the next week or two. 
• Build a tiny house – Done! Mostly. Almost. Are big projects like this ever really done? Another month or two and I’ll have it wrapped up and ready to be my office.
• Publish 12 vlog episodes – I’ve published 7 so far with 2 more coming. 9 out of 12 isn’t bad!
• Sign a book deal – This year I signed with Lisa DiMona to represent me as my literary agent (she represents Seth Godin, Ramit Sethi, James Clear, and many other great authors). Then I spent a lot of time outlining the book and writing sample content. The proposal is done and I’ll start shopping it around in the next few weeks. I just need to finish one more sample chapter.
• Redesign this site – Done! And it looks great. Thanks to Darrell, Rafal, Chris, and the whole crew at Authentik!

Also, as I mentioned earlier I hit my 2018 goal of getting down to 175 lbs!

New goals for 2020

• Grow ConvertKit to $28 million in ARR (growing at 3% month-over-month)
• 500,000 free users for ConvertKit
• Publish 12 vlog episodes & 12 educational videos for 24 total videos
• Launch a woodworking business with Oliver and August to sell handmade goods at the farmers market and other venues (Oliver keeps asking to do this!)
• Visit one of our philanthropic projects in person (either with charity:water, New Story Charity, or the clinic we are building in Burma with Earth Mission Asia).
• Charter a sailboat to practice our newly acquired sailing skills
• Complete 100 weight lifting sessions

I’m aiming for an ambitious, yet balanced year. That means pushing hard to grow ConvertKit to the next level with a new business model, but also being deliberate with my time and spending a lot of time with family.