Nothing Has Blown Up... So Far

The last 9 months have been the most relentless roller coaster ride by far. Greyouts, blackouts, you name it 😵‍💫

It’s been almost a full year since I published my first post on Substack. I told myself repeatedly that I needed to post again, but I never got to a finished post. I had a full-time job and whatever free time I did have was spent on customer support and making tweaks to my apps.

In other news, I recently got engaged and laid off, all in the span of 6 days! Oddly enough, I had been longing for this for months. With little to no time to spend on my HoldCo, I ended up in a losing battle trying to juggle everything. I neglected my businesses and was miserable at my job. Tuesday through Thursday, I would wake up dreading going to the office, just to twiddle my thumbs and push up a couple frontend changes. Having an actual business that I *could* work on made things worse. All the money in the world won’t matter if the work doesn’t engage me. This is actually why I left Amazon after 3 years. But that’s a story for another day.

Enough about me, let’s get into the business. Despite some shrinkage and churn in my first two acquisitions, the whole portfolio has consistently generated ~$2000 in monthly revenue for 9 straight months. This is a great signal, because it means that I’m on the right path. Given how treacherous of a journey this is, I could have easily crashed and burned at multiple points along the way. In all honesty, I should’ve been making $3 - 4K per month, but things didn’t exactly go according to plan.

When I explain the journey to those interested, I break it down like this. My first acquisition was the wrong business at a bad price. The second acquisition was the right business at a better, but still not great price. And my third acquisition was the right business at a great price (shoutout to Ryan Kulp!).

No matter how much due diligence I did, there was still a lingering uncertainty that an acquisition could sink instead of swim. So after enough deposits in my bank account, I could safely say that things were still on track without feeling delusional. PHEW.

So what’s next? With all the time in the world to work on whatever peaks my interest, I’ve been focused on my Shopify apps. I rebuilt and rebranded Extra Verification, which was one of two apps acquired in my third deal. The app is now completely automated with an updated UI. A couple days ago, I submitted another Shopify app to their app store for review after getting an idea to pivot away from TryOnify, my second acquisition. Looking ahead, I plan to iterate on these apps by developing new features and doing guerrilla marketing. There’s another app that can be rebuilt with special integrations in the Shopify ecosystem and other ideas that I have as well. This might sound like a lot, but I’m only taking on apps that are small enough to be finished within 2 - 3 weeks. Given how much AI has progressed, this only becomes more achievable now that I’ve cemented my tech stack and tooling.

In the near term, SaaS will command most of my time. I’m also in the middle of selling a home and have attended a few classes in Santiago Valdarrama’s **Building Machine Learning Systems That Don't Suck**. The boldest decision I’ve made (aside from getting engaged and selling a home 😉) is to stay out of the job market for at least 1 - 2 years. This will give me a fighter’s chance to see if I’m able to at least match what I was making previously as an employee, now as an entrepreneur. After dodging furloughs and hopping between companies for ~8 years, I also needed a break from Corporate America. I might be chasing fool’s gold, but knowing what I know now, I have to see things through. Put simply, I’d rather go down having fought, than not getting in the ring at all.

While micro SaaS and reeducating myself in AI and ML are potential pathways, my biggest bet will be to go all in on acquiring an IT MSP. I’ll still be able to leverage my technical background and the MSP industry is a lot bigger than I initially thought. The “worst case scenario” is I strike out on securing capital to make a deal happen, or again, shit hits the fan. It’s not really the worst thing that can happen though.

In my mind, the dumbest thing I can do is jump back into interviewing for Front End Engineer roles. Whether or not Software Engineers are automated out of a job by their own ingenuity, Front End development has always been too niche for its own good. And after the washout of “Web3”, AI has rung in one of the most exciting eras in software. The abstraction of Front End development is going to continue. Even if that doesn’t lead to the extinction of Front End devs, it’s not headed in a direction that makes me want to continue to stake my career on the future of it. I’ve also been doing it for 8 years and need a new challenge. As I recently explained to a close family member, growth comes from trying new things and making mistakes, not just staying in one lane forever. I considered adding design into my skillset and becoming a “Design Engineer”. Or I could go upstream and finally face my fears of backend development. To me, neither of those juices are really worth the squeeze.

Back to AI, there are 5 distinct levels to the development of AI (credit to Joe Lonsdale for breaking this down). If it turns out that I’m not intelligent enough to pivot and make meaningful contributions at the lower levels, I can still earn my keep in other areas. There’s plenty of room for everyone to eat. The question becomes, what lights a fire under my ass and sparks enough curiosity to keep me going? For now, having full autonomy over software that I own outright is enough to keep that fire burning. Even if the ship sinks and I go down with it.

Outro: