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Starting, Growing and Leading a Start-Up Company

Below I’ll share how I answered this question on Quora: Where is the difference between running a 5, 50 and 500 employee company?

Since I have my own personal experience starting a few companies (Bills.com and Freedom Financial Network) and growing them from conception through the phases of the first hire; then ten employees; then 50; then 100… and now about 725, I can share my own perspective.  But, like most things, this is simply my own experience.

When I’ve lectured on the entrepreneurial journey, I like to analogize this question to being in a band.  The skills, the energy, the level of passion and the leadership challenges are incredibly different at all phases, and many leaders cannot (or don’t want to) be successful at the different stages of growth.

Here goes:

  1. You wake up one day with a burning desire to share a vision with the world (idea phase). Your idea inspires you, and you think you can get your grungy friends to share that vision and passion. You might be drunk or on your third cup of coffee, which makes the idea sound better than it really is, but you are convinced the world needs this now.  When you tell your parents, they say your are nuts and to go out and mow the lawn or get a real job. Them telling you it will never work inspires you even more (but in the back of your mind, you’re thinking maybe you are a little crazy).
  2. First, you are a garage band (pre-alpha). You scrape together friends. You think about playing other people’s songs and just becoming a cover band (microsoft, re-sellers or the type of entrepreneurs who just rip off other ideas) – but stand strong in your vision to be original and decide to write your own music. None of you have a clue what you’re doing, but you dress the part and get the haircut and act like you know what you are doing. You and your pals realize there is no one else, so you play the instruments. They elect you singer (you’ve never sung before) and they sort of randomly divide up the instruments. This will haunt you for life. No one but your mom is listening.  She typically tells you that you sound terrible and to turn it down.  Maybe you’re Bono and The Edge, but more likely you are a bunch of friends who sound horrendous.  No matter how you sound, youlove what you’re doing.
  3. You book some gigs and you have a smattering of fans that are willing to be paying customers. Most of your ‘customers’ though are coming for free, since your band is really in beta. You end up loading up the equipment, setting up, playing the songs that you wrote (hopefully you are learning fast and killing the bad songs from the set-list, and refining the harmonies and the good songs), taking down the equipment and driving the van to a new town each night. It’s brutally un-glamorous. You don’t sleep much. You thought it was going to be a lot more fun. Your friends question what you are doing. One of them drops out of the band. You give them all a speech telling them that you know you all are terrible, but miracles happen. If you are convincing, the band stays together. The music is just awful, but still, there’s something special.  You’re all together. You see your vision coming together. If you’re incredibly lucky, you have a hit single (Instagram) but more likely you wake up in a small town with little money and tired and wondering what you’re doing. You get good at hiding self-doubt from your band-mates and certainly from your audience. You think about putting out some rock tunes and leave behind your punk roots.
  4. Whoa! Some bigger band named Benchmark or the Kleiner Perkins Triolikes your material and asks you to open for them. They are taking a risk, but they’ve been lucky in the past. You have a hard conversation with your drummer (he cannot really play anyway) and tell him that he needs to join the roadies so that you can get a more talented drummer in the seat. If he doesn’t, the band can’t get to the next level. The whole thing is a mess and you feel terrible, but when the new drummer joins for a practice session your spirits are lifted. You’ve scrapped almost all of your original material and re-factor the songs that you play live, but it sounds good. Even mom is starting to like it.The line between the audience and the band gets brighter.  This thing may work out.
  5. You’re huge in Europe. You’re selling out small clubs, and not just in your hometown. You start spending as much time booking shows and doing logistics (including keeping the headline act happy) as you do writing songs or playing music. It’s becoming more of a business and less of a personal passion, but that’s cool. For the first time, the new drummer starts singing as many songs as you do. It’s feels strange, but you think there is a chance that the band could maybe play a show and you wouldn’t even have to be there… it wouldn’t be the same, but it would still be a solid act.  All of your songs are now full rock ballads. You like it, but it’s a different audience. Most of the band has turned over.
  6. The band takes a huge turn. You think it’s for the better, but the act has grown so much that you now headline your own shows.  No longer are you a punk band, or even a rock band, but you are now the maestro leading an orchestra. You use third party song-writers and recruit talent that you could have never touched before this moment. Instead of ripped jeans, you now wear khakis and a blue blazer.
  7. You stop even going to the shows. There are more talented musicians in the orchestra and much more talented conductors leading them. The whole venture is so big anyway, that you don’t have time for the music. It’s turned into a cirque du’ soleil type of thing, and coordinating all of the people, shows and global scale take up all of your time. You reminisce with your co-founder about the days when it was about the music and all you ever did was write punk songs and scream into the mic. Those days seem like a lifetime ago.
  8. You’re proud of what the little garage band has become. In your own little way, you’ve changed thousands of lives and, hopefully, made the world a better place.

Each stage is fun.  Each step is unique. Some people thrive as a punk-band lead singer. Some people thrive playing first chair violin. Some people are great conductors. Few people can be a punk band-mate and then play the cello in the back of the room.

Enjoy each step. Hire people better than you are. Never concede or cut corners. Start out with someone you love to share the journey with… for me, that’s my co-founder.  Have fun.

Comments
3 Responses to “Starting, Growing and Leading a Start-Up Company”
  1. Great blog you have got here.. It’s hard to find high quality writing like yours nowadays.
    I seriously appreciate people like you! Take care!!

  2. Chris C says:

    This is awesome. What a journey. Thanks for sharing!

  3. Gretchen says:

    Great post.

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