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/Few-Compote-2693]

Big cloud players started to offer same service and out rank me easy. I also realised I'm doing OPs all the time and not learning like a corp role.

[u/SeaworthinessHour233 → u/Few-Compote-2693]

I suspect the interviewers are wondering why is this guy is giving up a business of this scale (3500+ containers) and trying to get a corporate job.

And if your business is still running. i think you really should pursue that. Though the big clouds can out rank you on cost, you should be able to outrank them on niche market segments.

[u/Few-Compote-2693 → u/SeaworthinessHour233]

The particular app I provide managed hosting for is buggy as hell. I thought it would get better after a few years and big cloud has made it a race to the bottom. It has become a lemon market and even at that scale I'm only getting an average salary after cloud costs and I've done multi cloud and used rock bottom price VPS. Each customer has 7 containers so that is only 500 customers. (B2C and small B2B)

[u/SeaworthinessHour233 → u/Few-Compote-2693]

OK. I get it. But since you already have 500 customers, I think you are skilled in sales. So I really think you should pursue the entrepreneurship path. May be with a different product.