Life at a tiny company

It's been a year since my cofounder and I let go of our team and buckled down to take on 2015 as a tiny, 2-person company. Turns out, 2015 had a lot in store for us: a couple high highs, a couple low lows, and a whole lot of just doing the work, grinding it out, one day after another. I'm proud of what we accomplished. I've never produced so much with so little. But for an ambitious company, the state of "tininess" is a special one: it's proud and independent, it's satisfying when it's not frustrating, and it's a lot of fun—when it's not driving you absolutely mad.

A tiny company is nimble. We were sitting in the last row at a presentation about ethics in data handling when I leaned over and whispered to my cofounder, "Remember that project you were talking about?"


"We should build it. Let's just build it."

He nodded. That's when the decision was made. A tiny company can make big moves fast. There isn't much research, many meetings or pitches or proposals, there aren't slide decks or whitepapers or lawyers or a prolonged stakeholder buy-in process. When you're half a tiny company there are only two people who get to decide, and in a single, quick exchange, you take the first step toward shipping a whole new product.

A tiny company doesn't have an office. Or meetings. Or HR. Or a vacation policy. Frankly, being half of a tiny company is kind of weird. It doesn't look very professional. This year, for me, it meant working in my basement office most days in my jeans and a tee-shirt and instant messaging with my cofounder till all hours of the night. It meant going out one or two days a week to meet up at a $10 per day rent-a-desk coworking space, or camping out at friends' offices. It meant constant, ambient chatting and almost no formal conference room meetings or inter-company email. We share a Slack account, Dropbox, calendar, and a GitHub account. You don't ask for a sick or personal day; when I needed to take a vacation, I said "Hey, I'll be offline these days. Take a look at these open tickets while I'm gone." There's no middle manager giving you side-eye if you show up to work late. There are no middle managers at all. You're both the bosses, the employees, and everything in between. 

Sounds great, right?

It is, until you check your bank balance. Which you do, several times a month.

A tiny company has a poverty mindset. When you're a tiny company you're tiny because you're just making ends meet, and that means every dollar that comes in matters a lot, and every dollar that goes out has to have a really good reason to make an exit. There are no off-sites or catered lunches or open bars or Monday morning donuts or Friday afternoon drinks or company-provided dual monitors or health insurance or retirement funds or even company tee-shirts with your logo emblazoned on them. There's you, on your laptop, constantly tinkering with a spreadsheet, brainstorming ideas for revenue growth or expense cuts.

A tiny company gets set back easily. When you're a 2-person company, one person's sick kid staying home from school means the company is working at half-capacity. One unexpected task delays development on everything else. One payments API deprecation can put the entire company's revenue stream into danger. Going to a conference, a dentist appointment, getting stuck in a long line at the DMV—all these things can slow down the company's progress because it's only two of you moving things forward. And if you're both not moving things forward, the company is standing still.

A tiny company wings it. In my time running my tiny company, I've had to get good at an array of tasks, which all have dedicated professionals who do only these tasks all day long in large organizations. Nowhere else can you be a software company's sole developer and also get to work on copywriting, email marketing, project management, user experience design, customer service, user feedback response, billing, managing a profit and loss statement, and reviewing stupid amounts of legal paperwork. (Okay fine, I'll admit I hired a attorney to do that last one.) Company tininess means your specialties and deep expertise matter less than your ability to learn just enough of the skill you need that particular day to achieve the goal at hand. Figuring it out and getting the job done brings a special sense of satisfaction, tinged with a hope that someday, you'll be able to hire one of those dedicated professionals.

Life at a tiny company is exciting, and difficult, but most of all, it's educational. In the past 12 months I've learned more about myself as a working professional than I have in any other year of my career. If you're committed to independence, pride yourself on rolling up those sleeves and figuring it out, and enjoy having more control (if smaller impact), life at a tiny, 2-person company is a daily education in capitalism, creativity, and survival.

Dive Deeper

If you want to know more about the Pastry Box Project, you can read about the genesis (and goals) of the project.

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A stream of all the thoughts published on the Pastry Box Project is available. Keep it open somewhere, and lose yourself in it whenever you feel like it.

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