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Thinking of joining a startup? One view of that world.

160318-news-silicon-valley Those who are regular readers know that I’ve spent the better part of the last two years at Provisioning/DevOps startup StackIQ. Last week that engagement came to an end.

I was knee deep in building Ingrained Tech when someone I trust called and told me “You have to check out my new gig. You’ll be impressed.”

I was. Even though I had clients and things were going well for Ingrained Tech, the idea that I could sit down and, using StackIQ’s tools, deploy a functional big data or cloud infrastructure in a short time, skipping all of the crazy “Oh did you forget to set this value in this specific config file?” It was an astounding piece of software, with founders that knew what they were doing.

So I jumped. I apologized to my clients, wrapped up existing contracts/work, and took the position. As happens with all startups, my role was broader than my comfort zone, and that was one of the things that appealed to me – after all, I was running Ingrained Tech, so what needed doing I was happy to figure out how to do.

I’ve worked in an array of startups in my time – from doing firmware for cell phones to CIO of a GIS startup – so I knew what I was getting into. And when I got the call that I was laid off, I realized I’ve never discussed the experience of startup work here on the blog. So I thought I would, because many people go into it relatively blind.

To be clear, StackIQ, and their open source project Stacki are still around, and will continue. The change was in needs of the organization, which happens in a startup… But we’ll get to that.

The first thing about working at a startup that you should know is that large parts of HBO’s Silicon Valley are real. Every startup I have worked for has been a collection of people trying to balance a conflicting group of audiences (investors, employees, big customers, average customers, contractors…), and all of them were doing so with an eye on funding, because that is the lifeblood of a startup. The longer you have to get the word out, the better your chances of succeeding. And every startup I’ve worked for truly believed in their product. Perhaps I’ve been fortunate or careful, but every startup I’ve worked for had good reason to truly believe in their product. The market and those competing constituencies on the other hand, not always so much to believe in.

If you’re considering going to a startup, others have said it before, but it cannot be said enough – expect to do new things. Indeed, expect that what you’re hired for may not be what the company needs at the moment, and you’ll be doing something completely different. There is good in that. For one, you’ll be expanding your skill set. For another, you are highly unlikely to get bored. And the final bit of good is the big one – you may carve out a new career in the process. By stretching beyond your comfort zone, you may find things you enjoy that you hadn’t considered before.

Since I was most recently at StackIQ, I’ll talk about it with them. This is already getting long, so I’ll focus on role change for the rest of this blog, and save the other things I wanted to talk about for another time.

When I interviewed at StackIQ, I was to be technical marketing/evangelist. Before I was hired, this was adapted based on company need (with my consent) to Solutions Architect. I spent my first week in sales training. This was definitely outside my comfort zone. I had trained sales staff, but no org had ever thought I needed to be trained, and as a remote employee, I spent a week between training sessions looking longingly over at engineering. The keys to the product and how it worked were locked away in engineering, but I understood I needed the sales info too, because it positioned us in the market, so I listened and learned (a lot, actually).

I spent the next six months doing sales support and working on demos that could be spun up at the drop of a hat. Anyone who knows about configuring the likes of Cloudera or OpenStack knows that “drop of a hat” is not something you generally associate with them. But we got to a point where we could show off the tool in those very environments (and more).

Then the direction of the company changed. The market we were in was limited, and there was a (correct, IMO) belief that there was more to do than simply spin up big data instances or cloud platforms. Both were interesting, but study after study was showing that they were not catching on as predicted, and the tool at our disposal could do so much more.

I spent May on the road talking about our big data products, then went home and moved away from solution marketing and more toward technical marketing/marketing/competitive analysis. Yes, for those working at F1000s, I do indeed know they are three different jobs. At some of the larger employers I’ve worked for the competitive analysis team rarely even talked to marketing except to deliver assessments of competitors. But startup land is different. You have jobs that need doing, and a limited staff to do them, so everyone does some. That was my bit.

I did take a bit of time last summer to make a whimsical newsletter for the marketing team that poked fun at the market we were in, while drawing out the strengths and weaknesses of different products. It started as a joke, and I kept the knee-slapping tone for several installments, but I like to think it helped solidify marketing’s view of the space. I had a lot of fun doing it, but don’t know that I ever would have shared it beyond the team.

The person who recruited me into StackIQ moved along, the primary product changed, I kept trying to alert the world to the benefits of their (our at the time) amazing bit of software. I have left the company, so there’s no reason for me to sing praises, and I’ll still tell you that if you install more than a couple CentOS or RedHat servers in a year, go get Stacki. It’s open source, so it’s free, and if you need support, of course StackIQ will sell it to you. It will make your life easier by automating installation of the base OS and configuration of the hardware.

So I stayed. I could tell the needs of the company were changing, but I stayed because I figured the product and its potential was worth the risk. And I pretty much knew the risk – if the needs of the company change too much, it makes sense to reorg and start doing things in ways that match the evolving needs. While I was willing to do what was needed, the company had to see to its long-term goals. I’m good with that – I even tried to resign for some of the same reasons a while back, though I didn’t want to, I thought it would be best. They asked me to stay, and I did to help the company through repositioning the model, but after this was complete, the company made some management changes and we agreed to part ways.

I could not wish them more luck. The product is solid, adjusting resource allocation may give them a chance to get the word out further, I truly hope it does.

Would I do it again? Wrong question, assume I would, since I’ve done it several times over the course of my career, and if you are not a regular reader, you likely found this post because you’re asking “Should I consider working at a startup?”. Well, in less than two years, I have added to an already large skill-set. Specifically, I’ve installed and used all of the server provisioning tools – stacki, cobbler, etc  – I’ve installed and used all of the app provisioning tools – Puppet, SaltStack, Ansible, etc – I’ve learned a lot about Business Development, I’ve written/managed different kinds of press releases, done slideshare in formats I had not before, and I met people that are either (a) Smart enough I would just learn from them, or (b) Nice enough that I consider them friends. I’ve had to work some long days, which comes with a startup, but I’ve had some light ones too – that comes with being part of a family, and in a startup is generally not begrudged. I’ve learned new ways to do some things in Python, actually installed and managed Jenkins (as opposed to just being a user), installed most big data variants, along with being one of the first to check out Chef Habitat… All in all, I’d say I got a ton out of the experience, and you would too, if you’re willing to work for it.

Enough of the good, how about the bad? Okay, it’s risky. I have known people that joined a startup in good faith and were laid off a month later. It happens, and doing your research won’t necessarily stop it from happening to you. Those options you’ll get promised? They’re not worthless, but they’re worth less than you think most of the time. The stock held by investors and founders and a few savvy C-level execs is worth more than yours. I’m totally okay with this, since without those founders and investors, there would be no startup jobs at all. But you need to be aware that if the investors are losing money, you are absolutely not going to get rich off your options. But this is just another risk, and one that can be managed a bit. Demand options, then don’t assume they’re worth much. If you’re lucky and joined a unicorn, they will be – far more than your salary – but for most startups, they’re practically worthless. When considering a job, consider those shares to be like most startups.

And it takes time and effort. I strongly recommend that either the people, the market, or the technology be so worthwhile to you that you’ll put in the extra effort. It is harder to drive oneself toward the success of a company that is counting on you if you don’t have one of those things to remind you why an hour or two at 10 PM might not be a bad idea.

Should you join a startup? If in your view the risk is worth the reward of helping to build an entire company, yes. If the people rock – are smart, or good people – yes. If the technology rocks – is solid and does what it claims, has room for growth – yes. But don’t do it for the pay – you’ll absolutely earn every penny of it – and don’t do it for the stock options, most aren’t worth the effort in startup-land (though if you’re a gambler, or truly believe in the product/people, this can be a positive tipping point instead). If you have the flexibility to join one, your horizons will expand if you approach it from a “what does the org need?” perspective. For some (myself included), this alone is worth the risk.

I would recommend yes in the case of learning, no matter who you are. But that’s me.

What am I doing next? Well stay tuned, I’m still deciding. My severance from StackIQ was enough to let me take a breather and figure that out, so I am going to. While returning to Ingrained Tech full-time is tempting, I want to make certain I’m choosing my direction, not letting it choose me. And in case you missed it, a lot of stuff in high tech interests me.

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More Stories By Don MacVittie

Don MacVittie is founder of Ingrained Technology, A technical advocacy and software development consultancy. He has experience in application development, architecture, infrastructure, technical writing,DevOps, and IT management. MacVittie holds a B.S. in Computer Science from Northern Michigan University, and an M.S. in Computer Science from Nova Southeastern University.

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