My first full year as an entrepreneur.
In retrospect, it was a year of a lot of growth pains and learnings. But I’m fortunate to say that 2021 was not a bad year. Unlike many others I know who lost loved ones, struggled financially, or faced mental health battles, my struggles pale in comparison
In fact, I’d call 2021 a breakthrough year.
I like to follow James Clear's annual review template, which leads you through answering three questions:
If you have a question about any of this or feel like there's an important piece of information missing, please do let me know and I'd love to fill it in as it probably a simple oversight.
My little membership site has managed to make it to “default alive” this year. The first part of the year was a slog if I’m being honest. A few of the items in the “what didn’t go well” section distracted me from making meaningful progress on Swipe Files.
It wasn’t until a candid conversation with my mastermind group that I realized I needed to focus exclusively on SaaS, create a lot more content, and drastically increase the price.
So I positioned all the copy for SaaS founders and marketers, the price increased from $99/yr to $499/yr, and I knocked out tons of newsletter content as well as recording a new course, Marketing Like A Media Company.
Immediately after positioning for SaaS, I noticed myself feeling inspired again. It’s been a huge unlock and a major reason for new member growth.
It’s also allowed me to effectively pitch and onboard a handful of sponsors for the entire year in 2022.
Here’s a list of places we traveled to this year:
Looking back at the list of trips we made this year was surprising in a couple of ways. We stayed fairly local, having only gone to Cancun outside of the US. I had completely forgotten about most… even though we made almost one trip a month. And our only real extended vacation was to Cancun back in April thanks to my wife who won the trip from an appearance on The Ellen Show all the way back in late 2019.
One of my goals from 2020 was to exercise more and find fun, active hobbies.
Enter: Pickleball.
Long-story-short… one of my close friends’ parents started playing and invited them to play, who then invited us to play.
We were immediately hooked. If you haven’t played before, I like to say it’s halfway between ping pong and tennis. The court is a quarter the size of a tennis court and is normally played with doubles.
It’s been our go-to active hobby and as someone who needs a weekly quota of some sort of sport or outdoorsy activity, I’ve felt a huge difference in my overall happiness since picking it up.
I’ve also played a bit of basketball, volleyball, and spikeball, which were nonexistent in 2020.
In June, I picked up a habit to do some weightlifting at the gym or at home and have stuck with it 2-3x per week since then.
My gains are small, but for the first time I feel like I have a routine that I both enjoy and can map back to differences in size, strength, and tone.
Lots of firsts in this category.
My first first is getting into DeFi thanks to Cathryn Lavery and Nat Eliason. My cash-on-cash returns exceeded 100%. And if you count the ENS airdrop I participated in and flipping my $PEOPLE tokens from the ConstitutionDAO, crypto produced over 5x return.
2021 saw an explosion in equity crowdfunding thanks to regulation changes. I went a little nuts investing in 21 companies, albeit with very small amounts. I figured that the regulation changes would trigger a boom that would surface a lot of top tier opportunities, and then it would slow down a bit afterward. The market as a whole hasn’t slowed down, but the quantity of quality companies raising crowdfunded rounds has definitely gone down since, so I don’t expect to make too many more investments through 2022.
I also wrote my first (very small) angel checks into Userlist, SparkLoop, and Wynter.
Nothing to report on yet, but I also got accepted as a Calm Fund scout, which I hope will be fruitful in the next year.
While I can’t share too much about numbers or specific projects, I’m personally very happy with the growth of SavvyCal and the consulting relationship I’ve built with Derrick. It’s been a breeze and very thankful that everything has been going up and to the right!
When I joined the On Deck No-code Fellowship, I started working on a capstone project as part of the program. That project was “Help A Creator.” I’ve been a frustrated HARO user for a long time, and the thought behind HAC was to compete and do a better job of connecting to creators and B2B writing teams.
The only problem? Per usual, marketplaces are incredibly tough to bootstrap. And I just didn’t have it in me. Plus, Elise Dopson launched Help a B2B Writer, which felt like a much better version of what I was trying to create and she’s much better positioned to do it.
I drastically underestimated the time I’d sink into it. I estimate it was somewhere between 70-100 hours invested. And when I finally decided to let go of it, I experienced some burnout in May and June.
Similarly, I launched my podcast Everything Is Marketing in February thinking it’d be a large audience-building project. How naive of me… Growing a podcast is HARD. Maybe the hardest internet asset of all to grow. While recording was fun and I’m proud of what I put out, it ultimately didn’t pan out as a positive time investment.
I also decided to buy some podcast ads in podcast players, sinking in $2,000 to grow the show. And that didn’t return any tangible difference in the analytics.
While it isn’t a net negative, I let go of my VA since they were mainly spending time on podcast production. They were immensely helpful with that process, but unfortunately that process just wasn’t a profitable endeavor.
Where do I start?
One of the themes that really clicked with me this year was the idea of leverage. When I’m juggling so many projects concurrently it’s easy to feel like death by a thousand cuts (or death by a thousand emails). At some point, it clicked that most of the work I do doesn’t matter. Not that it doesn’t need to get done, but it’s going to meaningfully help me progress toward my goals. At the end of the year, only 10-20% of my time will be spent on high leverage activities, and those will drive the lion share of the results.
I’ve been a yes man. Always have been. But that needs to change. Now, I count every hour as precious. When I first left Baremetrics, it felt like I needed to take every opportunity I could. Now, I need to choose wisely because there’s massive opportunity cost.
I remember Lenny Rachitsky politely shooting me down to be interviewed on Everything Is Marketing. His explanation was that he only does a couple interviews a year, and he just can’t say yes in order to keep up with his current workload. At the time, I thought it was a cop out. Now, I understand why he’s been so successful. Lenny, if you’re listening, thanks for the valuable lesson! 🍻
Another lesson I grasped was from Li Jin on “100 true fans.” Because time is limited, it’s generally better to have 100 true fans than 1,000 true fans. The economics are much easier to achieve and sustain as well. This was one of the big factors to 5x-ing the membership price of Swipe Files toward the end of the year.
Going into 2021, I was still doing a fair bit of marketing coaching for founders and marketing leaders. At one point, I had 12 clients. I learned that (1) losing 1.5 days a week to meetings was exhausting and (2) I’m not naturally fit to be a coach. If you’re an online coach, you’re likely extraverted, interpersonal, empathetic, accountable, flexible, and don’t mind answering the same questions time and again. I’m… the opposite of all those things. While I loved getting the inside scoop into marketing programs, I phased out of coaching entirely by August and didn’t look back.
Another crucial lesson has been on sleep. Previously, I’d wake up earlier and stay up later in order to get more done. My mom calls it “burning the candle at both ends.” And I figured that was fine since I was picking myself up by my bootstraps and making a run at this entrepreneur thing.
Then I got burned out.
And I learned that I was actually far more productive throughout the day when I slept at least 8 hours and didn’t work 12 hour days. I could focus, crank through the day’s tasks, and call it day in 7-9 hours while still feeling good versus getting up early, working 12 hours, staying up late, and feeling crappy the whole time.
