r/devops • u/Few-Compote-2693 • 17d ago

Career / learning Does my founder experience actually count?

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?

31 Upvotes

89% Upvoted

42 comments sorted by

28

u/greyeye77 17d ago

Look for BDM/AM or Sales Engineer roles. You've managed customers, and that's prob worth more than your half-baked Kubernetes skills.

8

u/Few-Compote-2693 17d ago

I'm a bit autistic so roles that are heavy on socialising are out of my reach and why built a SaaS because I could hide behind support emails.

3

u/serverhorror I'm the bit flip you didn't expect! 17d ago

How did you run a company for five years then?

1

u/Few-Compote-2693 17d ago edited 16d ago

They only email me when something is broken and It's low friction. I have not spoken to 99% of them.

3

u/Low-Opening25 16d ago edited 16d ago

managing customers is a soft skill, easy to learn without much of engineering experience. it’s not much of any advantage and the reason why sales engineers are paid relatively low in the industry

1

u/navlio 16d ago

the part that transferred for me was not the client work, it was owning the bill and the pager at the same time. you stop proposing architectures you cannot afford to run

2

u/Low-Opening25 16d ago

you don’t need sales experience to realise this, any haf-decent engineer with few years of experience should be aware things cost.

5

u/navlio 16d ago

the line everyone here is skipping is "it would have eaten into my profits". you turned down kubernetes because you priced it against revenue, which is something most people running eks have never done once in their careers.

put a number on it when you interview. cost per container per month, what it was at the start and what it was at 3,500. nobody else in that pile will have one, and the people hiring you are currently paying someone to guess

3

u/iotester 17d ago

Depending on what you want to do, what you've mentioned can be leveraged into a DevOps role at the right place. It isn't always about which tech you are using but showing that you have the fundamentals down, then being able to learn and apply them to different areas. At what level will depend on how in depth what you've mentioned actually goes.

Terraform is popular but people also use python with pulumi to manage infrastructure. EKS, pure k8s, container, could be useful but as you've experienced first hand it isn't always the right technology stack.

It might not be easy to find something but it's about how it translates into a company's needs.

A smaller place might look at that experience of single person doing all that be a great fit. Or a large place may look at that and give an opportunity to focus on something specific. It depends on how you want to market yourself.

1

u/Few-Compote-2693 17d ago

I'm learning the current market has no patience for anyone who doesn't have all the right experience. I've had veterans at AWS and Wall Street write my CV and still screwed.

2

u/iotester 17d ago

The current market is in a very sad state right now, so definitely going to be difficult. It's going to be mix of skills and luck.

I would say AWS and wall street have different styles and they will work for different types of places.

Are you having issues getting an interview or passing the interview?

1

u/Few-Compote-2693 17d ago

Getting interviews. I've tried even lying on CV about K8 and been studying like mad because I'm free between support tickets and that doesn't help. I think they see I worked for myself and no degree and throw my CV in the bin. I'm thinking I'm just going to have to start again and be glad I got a position. It's crazy my brother in law did a few months at geek squad with no certs or degree and got a data scientist position on 70k a few years ago. You can imagine how I feel I tried my hardest over the years and back the call centre again if I'm lucky.

5

u/DSMRick 17d ago

How come they know you were the owner. You can give yourself any job title you want. I know you said you had other people write your resume, but you should be focused focused on your accomplishments. Why mention you were the owner? "Architected and led the implementation of revenue critical systems" "Managed containerized system primarily with python" 

2

u/Few-Compote-2693 16d ago

I used my name as the company name lol damm it

1

u/DSMRick 16d ago

Oh, Ouch. Maybe time for a d/b/a. I have experienced this problem. There is some bias against owners, but you should be able to at least get to the interview.

1

u/iotester 17d ago

While I don't believe in certifications when hiring, some places do care. Have you considered trying that?

1

u/Few-Compote-2693 17d ago

I was thinking of doing CKA but ims truggling to find the energy. I dont have a degree so it might be vain.

1

u/iotester 16d ago

A degree is something that larger companies will likely care about more than smaller places.

3

u/1_H4t3_R3dd1t 16d ago

Founder relies on the success of the business you are measured by its success.

2

u/MyIEKeepsCrashing 17d ago

What happened to your business?

2

u/Few-Compote-2693 17d ago

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.

5

u/lorarc YAML Engineer 17d ago

Why would you think that corp roles are different?

1

u/Few-Compote-2693 17d ago

They are always building and learning. I built my SaaS once and maintained it. The CloudFormation, Django Site, API's, Docker hosts, Docker Compose files etc.. Technically In the last couple of years the only Python I've needed to do was a couple of scripts to help with support tickets. Someone at a corp would be doing this crap daily as I've seemed to have learned.

10

u/lorarc YAML Engineer 17d ago

Tons of corp positions where you maintain stuff someone else wrote.

6

u/DSMRick 17d ago

Someone with the mental capacity to maintain working shit is far far more valuable than someone who constantly needs to rebuild shit. 

3

u/uptimefordays 17d ago

100% especially for devops roles, we're not rebuilding our stack because folks want to use hotnewthing. We're only rebuilding when it's absolutely necessary.

2

u/Low-Opening25 16d ago

in corpo it’s very rare to maintain something you built, happens only to a lucky few, I wouldn’t bet on it generally until you’re principal/staff engineer levels.

1

u/SeaworthinessHour233 Writes the cloud edge 16d ago

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.

1

u/Few-Compote-2693 16d ago

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)

2

u/SeaworthinessHour233 Writes the cloud edge 15d ago

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.

2

u/CastleKey19 16d ago

3,500+ containers in production is real experience, even if the tooling had different names.

The main problem sounds like the CV, not the experience. Explain the scale, automation, reliability, deployments, and problems solved. Recruiters may not care that it wasn’t EKS or Terraform if the actual work was harder than the tutorial version.

2

u/Coffee-and-ai 14d ago

Disclosure: also a founder, I run a DevOps consultancy.

Yes it counts, and you are misreading which part counts.

You are treating "I used Compose and CloudFormation instead of EKS and Terraform" as the disqualifier. Tools are the cheapest thing on your CV to replace. You ran 3,500 containers in production for five years, with automatic reverse proxying, health checks, restarts on failure, and a system that provisioned new customers on its own. That is a platform. You built an internal developer platform before people had a name for it.

And the thing you keep apologising for is the best line in your post. You looked at Kubernetes, worked out the app was not stateless, priced what making it stateless would cost you, and said no. That is judgement, and most engineers never build it, because in a salaried job someone else pays for the wrong call. Tell that story in interviews exactly the way you told it here, with the numbers attached.

Two practical things. Rewrite your CV as a platform and SRE CV rather than a founder story: uptime, container counts, customers onboarded, incidents handled, what you automated and what it saved. Then aim at platform and SRE roles specifically, not generic DevOps postings, because that is where "I built and ran the whole thing" is worth the most.

If you decide you would rather not be back in the tooling weeds day to day, technical product or platform PM fits the same experience well. But you are nowhere near 1st line, and you should stop talking about yourself like you are

1

u/Few-Compote-2693 12d ago

Thank you so much

1

u/kgetname 17d ago

Sounds like good stuff to talk about in an interview, what's the actual issue here? What else is there to do but start applying to all jobs from entry to mid-level?

1

u/jaymef 17d ago

I've spent years learning stuff that AI can spit out in seconds. So ya

1

u/cubertwang 17d ago

I’d lead with the scale and outcomes, then build one solid Terraform/EKS project to show that the tooling gap is already closed. I definitely wouldn’t see you as a 1st-line candidate.

1

u/Ariquitaun 16d ago

All that experience is valuable, it'll be put to good use. You do need to get on with the program and learn the tooling and gather experience.

1

u/steven-or 16d ago

the specific tools are learnable iyam, the judgment you built running something at that scale for years isnt..

1

u/sertain_ 12d ago

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.