Tuesday, July 22, 2014

Confessions of an entrepreneur - six years in.

Last week I drove home from Steals.com at 1:30am, for the third night in a row. As I tried to keep my eyes open from lack of sleep and mental fatigue, I reflected on lessons I've learned the last six years while building my own company. Here is some of what I've learned - besides the obvious "I had no idea it would be this hard."

I've learned that since you're the boss and you're not able to share your feelings about particular situations with people anymore, that is quite often a very lonely feeling.

I've learned that people look at the life of an entrepreneur and think they want that for themselves, but they don't understand the risk and hard work that really comes with it.

I've learned that it makes you feel like you're being taken advantage of when employees take your company (and their jobs) for granted. Don't they know this started from nothing? I've also learned to quickly eliminate those that feel that way.

I've learned how difficult it is to read between the lines when people tell you what you want to hear, not what is accurate. You're the boss now, and you'll unlikely get the whole story or the full truth.

I've learned that it is very easy to critique your boss. But when you become one – you are finally able to relate to decisions you've seen your old bosses make in the past that you judged at the time.

I've learned that being an expert at a task doesn't mean that person will be good at managing people that do that task.

I've learned to never hire employees that need to be told what to do on a daily basis – unless their job is repetitive and easy to train for.

I've learned that there is a fine balance between creating process and structure, and fostering innovation.

I've learned that no matter the level of experience or college degree - it's often beat by hard work, passion and desire to win.

I've learned that smaller groups get more accomplished.

I've learned that sometimes people spend more time searching for answers than solving problems.

I've learned that firing someone is one of the hardest things in business to do. However, it can be a gift you give them – to move on to something that is a better fit for them.

I've learned that laying someone off is even harder - because they didn't necessarily do anything wrong.

I've learned that companies are teams, not families. You can't pick your family and you're stuck with them regardless. A team gets to pick who's on it, and holds each other accountable for their spot in the team.

I've learned that there's a lot more going on than meets the eye and when people judge your decision, they don't know what other data you had to consider when making that decision.

I've learned to manage people to their strengths rather than penalize them for their weaknesses.

I've learned it's a lot more fun to build a company than manage one.

I've learned that just because you hire more people doesn't mean you will get more things done faster.

I've learned adding more people sometimes just adds to the complication, not the efficiency.

I've learned that it's impossible to eliminate bureaucracy as the company gets bigger, even with the best intentions.

I've learned that there is as much reward seeing someone on your team reach their goals as it is to reach your own. And ironically, they're the same.

I've learned that no matter how professional I become, I am still affected emotionally by things that happen.

I've learned that when you're emotionally invested, it's hard not to take it personally.

I've learned that when running your own business there are amazing days, and there are terrible days. Each one makes up for the other. There are very few average days.

I've learned that many things you have to do in business have nothing to do with the business itself.

I've learned that just because you are busy, doesn't mean you're accomplishing anything.

I've learned that until you've been an entrepreneur, you'll never understand what it's like to be one.

I've learned that you have to make a tremendous amount of decisions every day.

I've learned that when money is no longer an object, you realize it was never the object in the first place.

I've learned that people do not get put into roles, they create a career for themselves.

I've learned the business is not about your income. It is about the outcome. If the outcome is good, everything else will fall into place.

I've learned that entrepreneurs only see opportunity. Not roadblocks.

I've learned that sometimes people use these roadblocks as excuses.

I've learned that being successful does not make you popular.

I've learned that you have to refuel your pump because no one will do it for you. People assume since you are the leader that you have all the fuel you need. Note again the lonely comment above.

I've learned that leadership has more to do with instilling confidence and setting direction instead of telling exactly what to do.

I've learned that everything you do becomes a reflection of your company. You are the brand.

I've learned that no matter what – unless it is your company it is not possible to care about it the way you do. Kind of like your kids.

I've learned that it's impossible to satisfy everyone at the same time.


I've learned that people assume that since you're an entrepreneur you can work whenever, wherever you want. Reality is - you get to choose which 90 hours of the week to work.

I've learned that humans are influenced by irrational behavior of others. Just because someone said it or read it, doesn't mean it's accurate. You can't believe everything you hear, or read on the Internet.

I've learned that the more you do, the more that is expected of you.


I've learned that a good attitude, positivity, raw talent and hard work go much further with me than an impressive resume. Hard work beats talent when talent doesn't work hard.

I've learned that an impressive resume only helps an entrepreneur if it's coupled with ferocious tenacity, laser focused dedication, courage, hard work, a can-do attitude and really good gut-feelings.

I've learned a lot - and clearly I have much more to learn as I continue down this journey of entrepreneurship and building a company. Hopefully these lessons can be of value to other entrepreneurs along their journeys.