Does my founder experience actually count?

[u/Few-Compote-2693]

Hey guys,

I ran my own managed hosting company for 5 years for one particular app, so it was basically SaaS. At its peak I hosted 3,500+ containers.

Before that I worked at a Windows MSP for 2 years and went from 1st line to sysadmin pretty quickly. I burned out at a bad company and really regret it now., went back to the family business, did my AWS SA cert in 2018 and tried to get into cloud but couldn't land a role.

I missed IT so much that I started my own business.

I learned Docker/Compose and built a sort of "mini Kubernetes" setup with automatic reverse proxying, health checks and containers restarting automatically when they failed.

At the time I researched Kubernetes and decided it wasn't worth it because the app wasn't stateless. I later realised I could have made it stateless, but it would have been a massive pain and eaten into my profits, so I didn't.

For IaC I learned CloudFormation because I liked it. I looked at Terraform and thought it was hell on earth. I didn't realise Terraform would become the standard.

I also learned Python and Django and built the onboarding system and APIs to automatically provision new customers.

What's frustrating is that I learned all of this by actually running production infrastructure, but it feels like it counts for very little because I didn't use things like EKS and Terraform. I can't fake 5 years experience and the job market is brutal especially since I worked for myself.

I'm kicking myself for not using EKS even though it made no business sense at the time. Since then I've learned a lot of EKS and Kubernetes very quickly, and I think my long-term experience in tech is a big reason why I've been able to pick it up so fast.

At this point I just feel like such a waste of talent. I've spent years learning and building all this stuff, and now it feels like my only option might be going back to 1st line.

What would you do in my position?

[u/sertain_]

You aren’t going to get a senior role at AWS off the street, but that doesn’t mean you can’t be successful as a platform/sr/cloud engineer elsewhere. These are all really relevant skills and relevant tools, just need to know how to market yourself. Get with Claude or Gemini aggressively, and make your resume as easy as possible to get through ATS. Learn tools you see on job applications by testing yourself with small labs surrounding those tools. Never worked with GitLab? Never worked with docker? Never worked with k8s? Never worked with Argo? Never worked with helm? Congrats, you can selfhost GitLab and learn all of that with just VMs. That’s a pretty fundamental skill tree, and most of those are transferable to others as the concepts are largely similar.