What I learned Working at a Startup

Estimated reading time: 6 minutes

I know this is not the first, nor the last piece about working at a startup, but I have a unique perspective on the matter.

My role in a startup was different than most. I was a full-time employee, but getting paid by someone else. I was in my last few months on active duty in the military and participated in a program called Skillsbridge. The Skillsbridge program is meant to allow service members who are leaving the service to work at a regular job for up to their last 180 days in uniform- all while still receiving military pay and benefits. The intent is to help ease the transition into civilian life for the veteran and provide discounted (or free) labor to employers and help them see the benefits of having veterans on their teams.

(As a side note- this is an EXTREMELY underused program. If you are a transitioning service member I strongly encourage you to look into it. If you are a company looking for talent, start off calling the employment office at the nearest military base. You may have to go down a path to find the right person, but the program has very little red tape and is very user-friendly to the companies.)

Having my own entrepreneurial desires and wanting to eschew the corporate vibe- I opted to work with a tech startup in Durham, NC. And when I say start-up, I mean when the founder hired me I became the second person in his company, besides him. We rapidly grew- to four people, including another veteran in the same program and someone else working part-time.

This was a really unique position to be in. I was in on the ground floor of a new business, but I had a comfortable paycheck and benefits still coming in from the military. I had zero skin in the game. This experience was just meant to help me learn how to work at a civilian job and, frankly speaking, get out of army life for a few months. All this to say that I can provide a fairly objective lens to look not only at the business I worked for, but the other businesses around us.

While I do not have a business background that bolsters my credibility as a business analyst (my military job was most closely akin to marketing-, but you wouldn’t think that on the surface) I do have a deep passion to start my own business. I’ve read dozens of business books, perused many an article on Medium about entrepreneurship, and listened to hours of Tim Ferriss interview successful entrepreneurs about starting their business. Again- by no means an expert- but through all that learning I saw many consistent themes put forth by the experts. And you would not believe how often I did not see these themes play out in reality.

So what did I learn?


  1. Don’t start playing business when you don’t have a business

There’s a reason the lean startup method exists. Without customers and revenue, you can start burning through capital. Fast. Real fast. And without a product? Even faster. Figure out the minimum you need to get to market and focus on making that happen.

Everyone wants to feel like they are an entrepreneur. They want to have the office in the cool space, pass out fancy business cards, and commiserate with others on the grind of being an entrepreneur. But without a business- and that means a product and customers- you are just funding a hobby.

2. You need customers

It doesn’t matter that you have the most whiz-bang amazing product or the software that is going to revolutionize humanity. If no one is buying it you don’t have a business.

3. No one is going to care about your business like you do

No one.

No.

One.

Not investors, not customers, not other entrepreneurs. There is a Grand Canyon-sized gap between interest in your business and action resulting in investment or revenue. What is going to fill that gap? A great product that solves the needs of your customers.

Want your team members to be more passionate about the business? Unless they care about the problem as much as you do or have equal skin in the game, they will not. Without the passion to fix the problem, this is just a job. Without skin in the game for them, this is just a job.

4. For your first team members, get people who want to solve the problem

Life on the startup grind is, well, a grind. To make the project work you might have to pull some early mornings, late nights, and lonely weekends. When looking for your first team members, look for people who also want to solve the problem you are trying to solve. These people are going to be underpaid and overworked- that’s the nature of a startup. But they need to believe in the why.

There’s a reason leadership guru Simon Sinek has a book called “Start with Why.” People can accomplish so much wore with purpose, shared vision, and believing that they are working toward something bigger. At the start, place a premium on the people who share your belief on the problem.

5. Don’t let the stats scare you

There are scary numbers out there about how early and often new business fail. The typical number I’ve seen is that half of new businesses fail within the first year.

Do you know what blew me away working around other start-ups? I was an intern, and an unpaid (by the startup) intern at that, and I was one of the first 3 people in our co-working office every morning and one of the last 3 to leave. And my hours? I was usually in about 8:15 and left around 5:30. That’s not the crazy-insane-stay-up-all-night-hectic workload of startups that people think of.

There were also a lot of tech startups around me and I saw many of them putting a lot of effort into building their product, but not nearly enough effort in doing market research and customer development. They were operating under the premise that their product alone would be good enough to solve all problems. Without proper customer development, you will not know if your business is actually going to meet the needs of your customers and without the right market research, you will not know if anyone is actually going to pay you for this.

This final point is here to illustrate that I learned you need to do the basics. Work hard and do your homework. That’s how you defy the odds.


Did any of that sound crazy? You have probably heard that same advice repeated a dozen times over by all the business minds on the internet. But if successful entrepreneurs keep pointing to the same themes, maybe it’s worth taking a look at them.

So did I leave the experience running away toward a regular job at an established company? Absolutely not. I loved it. Being a part of a small team trying to do something big felt great. Things moved fast and new challenges always came up. The start-p life is for me, and now I know what to do for the next one.

Related:

How the DoD Skillsbridge Program Works

Military to MBA (Part 1/7): Is It for You?

You Should Learn to Code. Seriously.