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The realities of joining a startup – confessions of a serial entrepreneur


Lessons learned from a start up junkie

I recently decided to make the switch from running my own consulting firm, which I have been doing for 6 years, to help start the OnRamp. There are many differences between working at a startup versus an established company. You really have to weigh out the reasons why you want to start a business or work for a startup.

I often get asked to join start up tech companies as a CTO.  Someone comes up with a great idea, but have no idea how to get it online.  That’s where I come in.  I take the idea and work with the developers and designers to get it online.  A lot of times I have to turn down the request to join the team, because of the commitment that involves.  Or because the business idea isn’t fleshed out enough, I’m not confident that the team in place is capable of getting this idea to market.  Because once I say yes, I am 100% committed.

So before you jump in and start to live and breathe start up, make sure you have really thought it through.  Sure, it’s a “startup” and it sounds super neat to say you work for one, but what are the realities you will face while on this new path?  What are the potential pit falls?  The rewards?

Here is a list of a few key things that I consider before joining a start up.

  • There is very little process and structure. You must take the initiative, innovate, identify problems, and power through them. No one will be holding you hand.
  • Your work really does matter. Speak up, fight for the things you believe in. You have a voice now – use it.
  • You have more responsibility at a startup. There are no account reps, customer service specialists or accountants. There is you and your itty bitty team trying to make its mark on the world with no money and a big dream. So what does that mean? Long hours, no social life, wearing many hats (some of which you aren’t super comfortable wearing) and don’t forget about the bouts of manic perfectionism that will leave you unable to turn your brain off to sleep.
  • Being a speed freak. All good startups try hard to stay agile. This means getting from idea to launch as quickly as possible. Features need to become minimum viable versions of your dream features. Get the products into the wild and in front of your customers as quickly as possible. Learn from the customer – iterate. Rinse and repeat. This can be hard for perfectionists and has definitely been a struggle for me.
  • There will be awesome highs and soul crushing lows. It will be an emotional roller coaster. Stick with it, no one who ever created anything worth while did it overnight. As Lao Tzu said “Do you have the patience to wait until the mud settles, and the water is clear? Can you remain unmoving until the right action arises by itself?”
  • Choose your allies wisely. You are going to be in the trenches with these peeps for the next two plus years. You will see them more than your friends and family and you want to be pretty sure that you aren’t surrounded by assholes. Trust me, been there done that.
  • The money? Join a startup because you want to be part of something cool. You will most likely take a salary cut and that mythical payoff may never come. You will have a big impact and have ton of fun in the process, but if that isn’t enough – rethink.
  • You are now your startup’s #1 sales person, whether you like it or not. Clueless in terms of sales and marketing? Better hit Amazon and load up on some books. Every person on the team, no matter what their role is now a sales and marketing professional. There is no such thing as “if you build it they will come”. You need to be spreading the word every second of every day or your awesome product will get lost in the ether.
  • Remember you are doing this to have fun, learn a ton and try to create something brilliant.

Those of you that have worked in start ups, what else would you add to this list?

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