How the Company-Startup Thing Worked Out For Me, Year 11: Massive Changes

Every year, I post a retrospective about what it’s been like to start up a company. If you want to catch up, check out past posts in the Brent Ozar Unlimited tag. This post covers year 11 of the company: May 2021 to April 2022.

Normally I do a blog post that weaves a few things together into a story, but this year, let’s just dump the rollercoaster into a bullet point list:

• June: Stack Overflow got acquired, and Erika and I had a financial windfall thanks to Jeff & Joel’s very generous stock option grants. We almost built a house in Iceland – we bought two plots and picked a builder, but Erika and I couldn’t agree on the details.
• July-August: our time in Iceland drew to a close and we started planning to come back to the States. I decided that Black Friday 2021 would be the last year for my Live Class Season Pass, and I would gradually start retiring from live classes before my 50th birthday.
• September: while still in Iceland, Erika and I decided to divorce. We’d been together for ~21 years.
• October: we moved back to the States, into separate places in San Diego.
• November: my annual Black Friday sale brought in about $1.5M, the best one so far. However, to minimize the number of weeks I was stuck in front of a camera, I had redesigned the teaching schedule in a compact, challenging way. I would teach European classes Mon-Weds starting near midnight my time, and then taught US classes Weds-Fri. That let me get down to teaching just 1 week per month, but those long-hour, time-zone-flipping weeks were mentally and physically demanding.
• December-January: I closed on a condo in Mexico thanks to Erika’s help, and I moved down there. I planned to stay there permanently and coast into retirement there.
• April: after really missing people and cars, I bought a house in Las Vegas and moved back to the US. That also changed my retirement strategy – I would need to keep working if I wanted to buy fancy cars.

This year was one of the most mentally challenging years of my life.

Some years, I feel like I’m steadily making progress towards a goal. Looking back at Year 11, I was running around like a chicken with my head cut off. I don’t have a nice, methodical story to tell for Year 11. I think if any one of a number of things would have happened just a little differently, Year 11 would have had an entirely different outcome. Year 11 was like one of those Seconds From Disaster shows where a whole bunch of little things add up to a surprisingly bad consequence.

So let’s just zoom out and talk big picture.

~18 months into the pandemic, I ran out of gas.

Erika and I were living in Iceland when suddenly my health started taking a weird turn. I coughed constantly and I started dry heaving – often enough to where I had a hard time keeping my asthma medicine down. At first, I couldn’t pinpoint the root cause: a volcanic eruption had made the air quality worse, I couldn’t get my normal asthma medicine in Iceland, and our diet had been changing a lot.

Looking back, I can see that it was stress. I was out of gas, and it was taking a toll on me physically.

That’s a weird thing to write because Erika and I were about as lucky as anybody could be during the pandemic. We were gallivanting around Iceland, making a great living teaching online classes, and didn’t seem to have a care in the world. However, the divisive politics of the time were leading to tough relationships with family members, we struggled with what we wanted out of life long term, argued a lot about our future, and I was coming to terms with my pansexuality.

Starting the divorce process obviously made the stress worse in the short term. I had a very clear vision that my life for the next several months would be running on a track, jumping over a series of hurdles. None of the hurdles were large, and none of them were life-or-death. I just needed to do the best job I could of making forward progress, jumping over each hurdle in order, and continuing on even if I didn’t clear one of them as well as I’d like.

The hurdles were things like taking an inventory of our assets, getting my own place set up, writing the marketing material for the Black Friday sale, teaching the first week-long stint of my Mastering classes back to back, closing on the Mexico condo, etc.

The finish line was December 11, 2021. On that date, I’d be done teaching the first round of classes after the Black Friday signups, and I sprinted down to Mexico.

I hit the finish line in Cabo,
and realized I couldn’t live there.

I loved Cabo and that condo, but two things became clear to me within a few months.

My friends and family weren’t traveling due to the pandemic. I’d bought the place hoping they would fly down for visits. Nobody wanted to fly to another country given all the COVID-19 travel restrictions – they kept asking me to come visit them in the States instead. <sigh> I guessed that would probably change in the long term, but it was really just a guess. Looking back, it was a good guess – my parents have gotten older, and are no longer able to do long international flights.

I missed cars more than I thought. Cabo is a terrible place for cars. The huge potholes, dirt roads, and salty air conspire to turn them into beaters in just a few years. I wanted to have a couple/few nice cars, do road trips, and attend Cars & Coffee events, but that wasn’t going to happen in Cabo.

So I decided to keep my home base in the US. Where to live? My heart will probably always be in Southern California, but a nice house there with plenty of garage space was wildly unaffordable in 2022. I looked for a place with low state taxes, great driving roads, great restaurants, and easy travel, and ended up with Las Vegas. I bought a 5-bedroom Vegas house that needed some work, and I could make it my own.

I was so excited by the prospect of a 3-car garage that I bought, uh, five cars. Near the end of Year 11, I had a Ferrari 328 GTS, Porsche 944 Turbo, Porsche Speedster Replica, Jaguar XKR-S, and a Range Rover. Went a little overboard there, especially for a guy who telecommutes, and today I’m still trying to balance that out. Looking back, I think I was overcompensating by diving into my hobbies because I was hating what I was doing for a living: teaching live training classes. Well, I loved teaching, but…

People loved the Live Class Season Pass,
but they just didn’t show up for class!

All through the pandemic, I’d been selling the hell out of my Live Class Season Pass. People paid once, and then could attend as many of my live classes as they wanted, whenever worked for them. In the Year 10 post, I wrote about how hard I worked to build a kick-ass set of live online classes.

On one hand, it worked really well: I sold a lot of Live Class Season Passes.

On the other hand… the students didn’t show up for class.

Over and over, I would teach a live class and only 5-10 people (out of hundreds of buyers) would show up. The students were just thinking, “I’ll attend some other time.” And… they never did. It’s hard to be upset about that as a teacher, because I was making great money, but it was just extremely demotivating to bring my A game only to have a handful of people actually show up.

During Year 11, I grew to actively resent the students for not showing up. I hated every time I had to show up for class and teach an empty room. First world problems, right? I should have been happy for the easy money, but… yeah, no.

So I closed out Year 11 in a grind.

Grin and bear it, I told myself, and saw October 2022 as my next finish line in the hurdle running. The Nov 2021 Live Class Season Pass buyers had a right to attend live classes for a year, and I’d scheduled classes through Oct 2022. But I was done with that, and I couldn’t wait to teach the last live online class, shut that down, and then never offer a Live Class Season Pass again.

My resentment towards my work led me to work less than I’d ever worked before, I think. I really hated what I was doing, and as a result, I stopped working hard on my blog posts, the First Responder Kit, PollGab, and pretty much anything else that required me to be in front of a computer. I just couldn’t get away quickly enough, and I needed all the recharging time I could get. That recharging went on through Year 12 as well, and seeing friends & family & conferences definitely helped. I knew I liked people, but I didn’t realize how much I liked being with people until a couple years into the pandemic.

I didn’t plan it at the time, but Vegas ended up being the perfect place to recharge those batteries. In Vegas, it’s like the pandemic never happened. We have a good circle of friends, we go out all the time, we hug and kiss cheeks, we taste each others’ drinks. When I travel to other places, I’m reminded that a lot of the US is still struggling with that, and it worries me that so many people are probably still in the bad mental state that I was in during Year 11. The feels. Everybody needed a good hug back then, and we still need good hugs now.