Here’s Why You Should Work at a 3 Person Company (Startup, Or Not).

Posted on the 15 September 2015 by Rwilner


This is an article about why I think everyone should work at a very small company.

This could be a “Startup” or not…it could also be a small consulting firm, or a bakery, or a house cleaning business, or an online school, or a dog walking company, or an art studio, or a house painting business.

The aspect that’s important is that there’s you, and a few other people, and a common sense of purpose that binds your success or failure together.


At my first job out of grad school, I was one person in a three-person company.

This was not a silicon valley social media crowdsourcing cloud computing venture capital backed startup. We did not have a ping pong table.  (we barely had a conference table)

We designed, manufactured, shipped, installed, and supported maritime control systems — the electronic things that control the ship’s engines, steering, autopilot, etc — for high performance marine craft (boats). Our customers were the US Navy, international Navies, luxury yachts, and commercial ferries, as well as some small high performance craft and working boats, like firefighting boats.

Our funding didn’t come from angel investors, investment bankers, or venture capital.  Our funding came from two places: the founders and customers.

I worked 90 hours a week.

I wrote code, designed circuits, and fixed hydraulic and mechanical systems to make the things work. I wrote the technical and user documents that explained how the things worked.  I assembled and tested things, and then packed and shipped those things.

Then I installed them.  I did a lot of the work myself and coordinated teams of people. Many of those people didn’t speak English very well. Most were not interested in taking direction from a 24 year old kid. (who could blame them)

Then, I provided support for them all over the world. Remotely if possible, but sometimes you have to get on a plane. (I was not flying business class.)

I had that job for about 5 years (full time and contract).

I learned more about myself than I could have imagined.

I wouldn’t trade this experience for any degree…what I learned, can’t be learned any other way.

Here is a defining story from this period of my professional life. I carry this with me today (for better or worse).

It is a story about getting the confidence to tackle the hard things in business and in life…and a philosophy on how to approach any challenge, in any size company.


We won a new contract for a custom control system. The customer was a navy in Asia, and the application was a “special mission” boat. The system was complex and required some special software and changes to our standard hardware. It was also challenging to nail down the user requirements due to the time difference, language barrier, cultural differences, etc.

So we spent most of a month designing, building, testing, redesigning, rebuilding, retesting.  And when I drove the 75 pound box of stuff we had made to FedEx at 9pm on a Tuesday, I knew it would not be the last time I would “see” this system.

It took three months for shipping and installation…just long enough for me to have forgotten all the weird changes I made to get the system to (theoretically) work.

2am on another Tuesday, my boss called me. I knew he wasn’t calling to say that everyone was just! going! great!

Nope, the boat wouldn’t turn left (“port” in maritime speak). They were about 3 miles out to sea in the Pacific.  No way to turn left.  He really wanted to turn left.

He said, Rich, why won’t the boat turn left?
I said, well, I’m not sure.  It SHOULD turn left.
He said, well, we need to turn left. There are 15 people on this boat and we would like to no longer be on the boat and that requires us to turn left.
I said, OK, but I don’t know what’s wrong.
He said, Rich, sit up in bed. Look all around you. (I remember actually doing this.) If you don’t fix it, who will?

…Who will?  

I thought about that.  I had no engineering department, or quality engineers, or vendors or contractors or suppliers to lean on for help (even google wasn’t much help because this was 2004).

I had me.


I went to the office, set up the test rig, fixed the software, emailed the file to the ship yard.

They sent a motor boat to the ship with a USB drive.  (I slept for 2 hours while that happened)

Then I walked an officer through the fix in very broken English. It would be unfortunate if the software patch didn’t work after all of that.

But…the boat turned left. They were able to dock the boat and everyone was able to get off. (Phew)


I made one observation immediately:

The horribleness of causing the problem was matched only by the elation of fixing it. I don’t know of any other way to get that feeling. (If you do, please let me know)

During my time at this job, I had several other experiences like this one.  As I thought about these experiences, I discovered something else…something that has been a prime mover in my career and life:

I developed the confidence that I could figure something out, even if that thing was unfamiliar, complex, and important.

I learned to be self-reliant.


OK, I’m now going to get on my soap box. (Please indulge me)

People say “big companies should act like small companies!” “They should act like a startup!”

What does that even mean? “Big companies” are not people or cats or chimpanzees that have the ability to “act” like anything.  The way big companies “act” is the sum of how all the people within that company — and especially leadership — act.

I think what people mean is: people in big companies would (or could) be more effective if they BEHAVED like they were in small companies…and specifically, if each actor in a big company was more self-reliant.

Self reliance is a trait that is ingrained deeply and celebrated in the American value system (probably many other value systems too).

We romanticize it: the farmer that can fix anything on her farm, the cowboy that builds civilization in the wilderness, the entrepreneur that pulls an idea from thin air and simultaneously makes a billion dollars and changes the world.

In a company, you may know self reliance by another word: accountability. It means you tie your personal success to the company’s success. It means the success you enjoy (or failure you learn from) is tied directly to the decisions you make.  It’s on you, and you’re cool with it.

Here’s what I believe: there should be one approval on a document. One owner of a decision. A single point of accountability for the things that drive the business (or fail to).

I certainly don’t mean that this accountable person is not the only one with input into making the decision. But they are accountable for getting all the input, assessments, analysis, data, and consensus needed to make the best possible choice…and they are accountable for the business result.

In this model, the company relies on a person to deliver something. That person relies on her team to choose the right thing, plan it, monitor it.  And that person relies on herself to deliver it.

This requires trust…the company leadership must trust employees, and employees must trust each other (and their subcontractors and consultants and vendors). It requires commitment, and delivery.

But I believe this model of the “empowered individual” can deliver more for less than any bureaucratic decision by committee ever could.

I don’t have a raft of scholarly articles to back up this claim.  All I have is my own personal experience.  And this claim has been proven to be true for me over and over again, at 10, 1000, and 100,000 person companies.


Is self reliance revered in your company? Do you value it in your daily work? Do you strive for, and advertise, your own personal accountability with your colleagues?

I’m not going to tell you that you should. I wouldn’t presume to know what the result would be. But what I do know is that if everyone in one group, or one department, or one entire company approached their work from a place of self reliance…the work would be better, and the results would be too.

Because if there’s one thing I look for in someone I rely on, its that I know that person can rely on herself.

Can you be that person to your colleagues?  Try to be.  See what happens.

I predict only good things will come to you.


  • Next Read: Here’s Why You Should NOT Work at a Small Company / Startup. –>

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