Brian Casel
Brian Casel

2021, a 'shake-up' year

by Brian Casel on December 28, 2021
See what I was up to that year · Subscribe

In my 13 years in business, a few of those years stand out as “shake up” years.

“Shake up” years mark the end of a major chapter in my career and the start of my next one. To date, my “shake up” years were:

  • 2008: became self-employed
  • 2015: Sold a business, started the next
  • 2021, welcome to this short, but exclusive club. You deserve it.

2021 was quite the “shake up” year for me.

The headlines

The challenges

There were many. Mostly mental. I’ll share what I can down below.

For now, I want to preface with this: There were (and always are) more challenges than what I can (and should) share publicly. So if any of this sounds like an overly rosy year full of wins, it certainly was not and it didn’t feel like it a whole lot of the time.

But I’ll take the wins too and writing about them here helps me stop and give them the recognition they deserve.

Celebrating with lifestyle upgrades

“Shake up” years, like this one, mark the end of a multi-year stretch where I was grinding it out, building toward some kind of outcome.

To help mark the passing of these chapters, I’ve made a habit of trying to physically upgrade my/our lifestyle in a meaningful way that we’ll feel day-to-day.

In 2009, after completing my first year of self-employment, my girlfriend (now wife) moved in together in a much nicer NYC apartment.

In 2015, after selling my business, Restaurant Engine, we used that money on the down payment for our house with plenty of space here in Connecticut.

Casel Family My backyard office at our home in Connecticut.

In 2021, I ordered a Tesla :)


But I’m still waiting on delivery :(

Now let’s get into it. What happened in 2021?

I sold my previous business, Audience Ops

The full story is in my post about the exit here.

Now that we’re 3 months after the sale, here’s an update:

First of all, no regrets :) It took a lot of internal debate and emotional management to bring myself to the point of being ready to part ways with Audience Ops, the business I had been running for almost 7 years (not to mention, our primary income source). But sitting here today, I can say with certainty I don’t regret the decision to sell.

Even though I wasn’t spending a ton of my time “in” the business when I owned it, having exited has definitely brought a new level of freedom (mental freedom more than time freedom). I’m able to fully focus on strategy and execution toward building the next big chapter of my career.

One surprising note: The post-sale transition has required–quite literally—zero of my time and input (beyond handing over passwords, introducing the team, etc.). I think this speaks to the incredibly talented and well-organized team who operated day-to-day without a hitch throughout this transition. It also speaks to the experienced leadership and organization JD and his team built with SimpleFocus and their products portfolio, as they’ve been able to pick up and run with this business so smoothly.

I started my next business, ZipMessage

It started as a “shiny object” idea in late 2020, but by January 1st, I felt it was time to give this little idea, ZipMessage, a shot.

I built an MVP in 3 months and had first paying customers in April, 2021. It had pretty clear and consistent uptake heading into the summer, and by that point, I had a strong feeling I was onto something—not just a side hustle, but what could be the business that will occupy the next big chapter in my career.

The signals I was seeing were:

  • Widespread positive feedback from more people across more networks than I’ve seen with any of my other products to date.
  • Users signing up, actively using, and upgrading to paying customers at a faster rate than my previous products.
  • Simplicity and ease and speed for someone to “get it” and then share and talk about ZipMessage—again, that felt easier and faster than all my other stuff before.

Those signals continued throughout the year, with steady customer and user growth every month. I’m incredibly proud of the product my small team (essentially me plus 1 FT developer) have been working on every day this year. The product has come a really long way in such a short time! I couldn’t be more excited about growing this product in 2022.

December 2021 turned out to be ZipMessage’s best month yet—a nice capper to it’s first year of existence. It has already surpassed my previous businesses in terms of number of paying subscribers and continues to see healthy, but still gradual early traction.

I wouldn’t say it’s reached the “promised land” yet but it’s well on it’s way and the path ahead is exciting… But still lots of work and growth to unlock. More on that in my 2022 outlook post!

Taking funding from the Calm Company Fund

After running 100% bootstrapped for 13 years, ZipMessage was the first time I took any outside investment.

For this product, and for this moment in my career, it just made sense. I explored several funding options (including the option to continue to fully self-fund), but in the end, Tyler Tringas and Calm Fund made it an easy no-brainer. Good offer, good timing, easy, no-stress process from conversation to deal to done.

I’m still settling into the Calm Fund community. I had a couple mentor calls already and I’m super excited to do a lot more of this in ’22.

2021 Challenges

As you might imagine, the career shake ups I described came with a heavy dose of stress. If I’m honest, 2021 was probably the most difficult year for me, mentally.

Earlier in the year, the decision of whether or not to pursue a new business idea vs. stay focused on the one(s) I had brought a major mental weight. I don’t take this decision lightly and I batted it around with my friends/advisors and myself a lot. Second-guessing myself on a daily basis takes a serious mental toll.

Then there was the decision of whether or not to pursue an exit from Audience Ops. There was a period of indecision there, but ultimately the time felt right. 

Once I was in a deal to sell, I found that process quite stressful. Between the secrecy of it all, the twists and turns in deal structure, the legal and accounting stuff… Not fun. I said to some friends at the time: “Even when a deal is progressing perfectly fine, it’s still stressful AF.”

Then (while in the deal to sell my business) I was also weighing the decision of whether or not to take investment for ZipMessage. Again, lots of indecision and analysis paralysis. Thankfully, the process of moving forward with Calm Fund was delightfully fast, smooth and lightweight.

All of that was happening amidst year 1 of my new SaaS business. All I wanted to do was stay focused on building the ZipMessage product and onboarding our first 100+ customers. This work was clearly my favorite highlight of this year. But man, there was a lot of other stuff on my plate throughout it all.

Excercise in 2021

My primary method of computing mental stress is to stick to daily morning exercise. I’m not 100%, but there’s no doubt: The days I exercise, are days I feel good and do good work.

Throughout the nicer months, I cycled and walked in local parks and by the water.

Water My favorite spot to walk and think in coastal, Connecticut

I tried (and failed) to get into running. Too painful.

I recently came across Peter Attia’s info about Level 2 exercise (I started here) and went down the rabbit hole that led me to pick up a new indoor Schwinn IC4 + Rouvey iPad app. It’s great for Winter morning workouts.

Books in 2021

2021 was the year I got back into reading, listening to books. I paired this habit with morning exercise and that combo works perfectly for me.

I’m a fan of biographies and real stories. Here’s what I listened to in 2021:

My music hobby in 2021

Making music in my home studio is my lifelong passion, and now my go-to creative hobby.

The challenge is I spend so much creative energy when designing products (especially a new product) that I hardly have any juices left to throw at my guitars.

But I still managed to pick it up a few times and gather the nerves to Tweet some half-baked jam ideas.

By the way, anyone wanna start a remote/async band? ;)

3 Takeaways from 2021

  • Daily exercise really helped me feel better mentally. I wasn’t 100% consistent, but I’m a lot more aware of this connection now.
  • Simplicity and speed in product is everything. With ZipMessage, I’m seeing that first-hand, more than anything else I’ve worked on.
  • When you feel it’s time to move on, move on. Numbers won’t tell you when. You tell you when.

Travel in 2021

Family trips in 2021

  • Several roadies to skiing in the northeast US.
  • A week-long spring road trip Asheville, NC
  • Cape Cod, Massechusetts
  • Washington, DC,
  • Bar Harbor, Maine
  • Day trips to NYC and Boston
  • Florida with a day at Disney

“Work” trips in 2021:

2021 Photos

Daddy daughter chairlift My daughter Emma (7) started riding the lift with her Dad!

Glamping “Glamping” in Maine

Asheville Chilly hiking in Asheville, NC

Disney OK, I think we’re good on Disney trips now.

CaboPress pool Talking products by the pool at CaboPress.

Fall hike Hiking and talking business in Colorado.