Six years, four startups, one company of my own. Hired as one of the first ten employees three times...this is the shortest short version of my resume.

It's been a wild six years. Most of the time things were exciting and fun at my companies, and I learned heaps about business and life. It's crazy to think how fast you have to learn new things with little structure at a startup...

Some people say working in a startup is like getting a "mini MBA." I wouldn't go as far as to say that, but its pretty damn close!

Certainly, there's a lot of hype today surrounding the startup ecosystem and entrepreneurship. College age people across the globe are building apps and getting million dollar valuations super quick. Every industry is being disrupted. SNAP recently IPO'd at a $25 Billon valuation. You get it. 

If I had a dollar for every time I heard someone say, "I'm at a startup," or claiming they're an entrepreneur, I'd be pretty rich.  It's no longer rare. In fact, according to Global Entrepreneurship Monitor (GEM), nearly 41 Million Americans were involved in entrepreneurial activity in 2016.

I've been involved in entrepreneurship and startups my whole life. From Lemonade stands to my event company and then working with tech founders to find product marketing fit and scale the past six years...I've experienced the un-sexy realities of startups first-hand.

The following is from my personal experience working with founders at startups. Just some things to consider before you enter into your first startup (especially pre-Series funded):

To stand out, you need to add value well beyond your job title

No secret: your worth depends on how much value you can offer. If you're a one-trick pony you probably won't thrive in a startup environment (again, talking about pre-Series funded startups).

There was a time I worked in sales and wanted to become a product guy. So I said to my colleague at the time, "I'm so over sales and really want to get into the product side of things." His reply: "Add value wherever you can, whenever you can."

The next day I asked the Product Manager where I could help her and she walked me through JIRA. Next thing I knew I was grooming the product backlog, just like a real Product Manager...

Not sure where/how to add value in your job? Give one of these a whirl -

  1. Have a casual conversation with the CEO asking her/him what they personally need. Tell them you just want to help
  2. Think about a company-wide process that sucks and the solution. Email the team proposing the enhancement
  3. Sit in on meetings with leadership and take notes. If people ask what you're doing, tell them you're there to take notes FOR THEM. Before you know it you'll be involved in the discussions

More often than not, showing that you care about the company and your work, and that you truly want to help beyond your job description is super simple- just ask someone you don't normally interact with if they need help and go from there. If you're in sales, walk up to the CTO and ask them. And if you're an engineer, do the reverse.

Successful startups have 24/7 leadership

One startup I worked with had a super cool executive team. They were young, hungry, and always had their doors open. I joined them because they were passionate and seemed to have their shit together. I looked up to them. I wanted to be like them.

Then one day I heard a few of the founders talking about my colleagues behind their backs. I was crushed.

I felt bad for everyone involved and knew I'd never feel the same way about the company's founder ever again.

The situation taught me that true leaders act like leaders 100% of the time. Startups are unpredictable and it can be hard to tell if the leadership team are "true" leaders. Generally, you want to find a startup that has at least one experienced founder.

Advice to founders: If you can't be a 24/7 leader, find someone who can, otherwise your employees and colleagues will lose trust and faith in your abilities slowly, but surely. This leads to high turnover, poor moral, and all together bad working environments. When there are only 15 people in the company, you better be sure no one is listening behind your back...

If you don't have equity, don't fall in love (even if you do have equity, still, don't fall in love)

Look, I'm not saying don't be dedicated to your company and love your work. What I mean by "don't fall in love" is simply don't become so obsessed with it (the company) that it becomes your only reason to be alive.

If you don't have ownership it's not worth spending 80 hours a week working on it. Simple as that. Even if you DO have equity, still, probably not worth it. You have a higher chance of being struck by lighting twice in one day than cashing out and becoming a millionaire from a startup. 

When I moved from Chicago to Austin I searched far and wide for a game-changing startup to work with. After three long months of hunting, I finally found it. My dream job had arrived!

I was employee #9. Didn't get any equity when I joined, and that was fine. I knew that there was a massive opportunity in front of me just by joining early. Then, after one month of waking up every morning more excited to start working than ever before, I was laid off.

Ever feel like you're in a movie? That's how I felt when I got the call. A startup burning all of their cash just a month after hiring me?! Not right.

I moved on to yet another startup and got equity, only to be laid off 10 months later...

The moral of the story? While working at a startup has it's perks (no rules), falling in love because you have "ownership" is not worth it (from my personal experience).

 Advice if you're evaluating startup opportunities: 

  1. Ask the founders what the cash situation is like. Only four months of runway? Proceed with caution.
  2. Ask the founders what the turnover has been like. If they're churning through employees, something ain't right. Proceed with caution. 
  3. If the company is pre-Series funding, ask them what the timeline is for Series-A. No plans for another round of funding is a red-flag that they may not be forecasting correctly. Proceed with caution!