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Lessons learned from 11 years in start-ups

I’ve been working in start-ups for nearly 11 years now (holy cow).

I’ve gone from a junior employee just out of college making less than $35K a year –– during which I paid off a $10K student loan! –– to managing teams, working closely with the top names in venture capital, and even making enough off of an IPO to buy a house.

In many ways, I’ve lived the dream within the start-up world. And I’m from a small town in East Texas –– and was just lucky enough to stumble into tech when I graduated in 2010 –– after 4 months of applying to 10+ jobs a day. That recession was rough.

Here are some things I’ve learned:

  1. There is BS everywhere.

The grass always look greener on another team, at another company, etc. It isn’t. There are skeletons in every single company’s closet, and it’s usually best when you know what they are and how to work around them – which means you have to stick around long enough to figure it out. (Clearly if there is some real BS happening, like all the isms, leave immediately).

  1. Teamwork truly makes the dream work.

There’s not a lot of room for ego in start-ups –– though you can bet your bottom dollar it exists there! Folks who aren’t teamwork oriented don’t last long. Do your best to suss out an “on my own” mentality from a “tide that rises” mentality when hiring. You won’t always get it right. That’s ok.

  1. The best results take a long time –– like…years, not months.

Start-up founders don’t like this. Start-up investors know it’s true. Create flywheels. Optimize for growth. Yes, yes. But start building your moat now. Small wins compound – and what is 5% growth WoW now is more than 1,100% YoY.

  1. There’s only one playbook I know that works - every single time.

That’s building your network and trusting them to help you when you need it. Use the investors and board members’ expertise and connections. Re-hire people you know you work incredibly well with. It doesn’t matter if that’s full-time or contract. Set up monthly or bi-monthly calls with these folks –– become friends. Prioritize this even over other high priority items at work. Your mental health depends on your ability to do this.

  1. People who are bad at the above often play office politics. Don’t play with them.

  2. Good project management is the real key to scalability. It increases productivity, makes it easy to see who is doing too much, and even easier to cut what isn’t as important as everything else.

  3. Finally, do everything in your power to not tie your identity to your job. You are more than your job. You are more than your social media network. The best mentors and offline network will remind you of this often. Trust them. They mean it.

Take the vacation, the mental health day, the hours off to help your brother move. This start-up isn’t forever. Neither are you.

  1. 1

    Thanks for the insightful article .. What are the most important principles to cultivate healthy and sparking teamwork environment among members ?

  2. 1

    There is BS everywhere.

    Preach

  3. 1

    Thanks for sharing such insights. I'd like to hear your thoughts on improving project management. What are 3 main things you secure when you want the project to run great?

  4. 1

    Seems like you've faced with harsh reality many times. There are so much pain under these words, so that I don't think now that it's a great idea to start a company.

    1. 1

      "Hard choices easy life, easy choices hard life"

      Running your own company or working in a startup is tough but also so much more rewarding.

      Not saying you have to do it but it's worth some consideration 😁

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