It’s Lonely Out There

Growing up I always admired the polished corporate executive and set my dreams to climb up the corporate ladder.  It wan’t until I got my MBA did I finally wake up to the miserable nightmare I was in as part of corporate America.

Life was ok, pay was excellent and I had started to become complacent.

I suddenly hit 30 and my mind was on the verge of exploding from routine boredom.  Mid-life crisis hit me strong.  I was going nowhere in my job.  I had excellent reviews from my supervisors but actually spent more than 50% of my time either working out in the corporate gym or reading 20-something startup stories and VC blogs.  Anxiety hit strong.

This was amplified when I decided to support my wife in her own aspirations of leaving her horrible job and opening up a consulting business.  So, I had to put off my entrepreneurial dreams for a couple of years.  During that period of time, I started drinking heavily and going out with friends just to numb the feeling of nothingness.  Reading about the Big Bang theory and black holes did make the experience more tolerable.

During my nights out, I saw a well known VC partner at a strip club. He was the spitting image of Waldo and I would never have guessed he would go to such places.  He was probably celebrating with a company he recently funded.  They came from the upstairs VIP lounge and his hair was all messed up.  This is when I said to myself, I definitely need to get them to fund my startup when the time comes.  I wonder how they end board meetings.  Trips to Vegas?

After my wife started doing well, it was time for me to finally quit my day job.  

It wasn’t all sugar and spice and all that’s nice when I quit. I am single founder and bootstrapping the startup using my own funds.  I have a few clients. The pivot that I am currently pursuing has been getting traction from both users and advertisers. It is starting to look a bit brighter on the other side.

During the last few months though, it has been a very lonely ride.  I would have loved to have a cofounder but the field my startup is in is not that sexy.  Definitely not like Foursquare or Facebook.

Most of my time is spent developing, bug fixing and cold calling potential clients for business.  I thought having a startup would be much more exicting than this.  Filled with booze, women and pranks.  Oh, wait, that’s what SXSW is for.  

What I learned from my startup is to definitely pursue something you have experience in, have a strong passion for and already have an established network of potential customers/partners in.  I think a successful founder will have at least two of those three traits.  Without any of these traits, it will be hard to build something and keep going.  Especially, when the original idea does not do as well as you thought and you become discouraged.  Only to find out later that there might another angle to this business.

I think I will reach my goal and hopefully have Waldo on my board soon.  If not, the contingency plan is to open a food truck somewhere in Hawaii and surf most of the day. 

  • If you don’t love what you are doing, stop doing it. Don’t do it for the money and the strip clubs, do it because it is what you want to be doing. If you want to be in Hawaii surfing most of the day, that’s what you should be doing.

    • Maybe I did not communicate it well in my story but I love what I do now, I wish I had more funding, traction and co-founder but hoping that comes my way soon. It is a lonely road in the beginning especially when you do not know where the start up is headed to. But definitely an exiting ride.

  • Nice story. I started up as an entrepreneur quite young and had some success, haven’t done millions or received millionaire investment, but certainly made a decent living out of my own Startup. Yesterday I turned 30, and for the past couple of months have been living through something similar to what you describe you went through in the corporate world. I’m bored, very bored. Lonely, at times, and quite frankly I don’t know what to do. I know I can nail it and build a successful company, but I’m not even sure that’s what I wanna do any more. So I’ve been thinking to get into a corporation and start doing a career there, but then I’m quite old for that already, and I’m not sure I’m very passionate about that either. Although a steady flow of money sounds promising for a change. I don’t know, just wanted to share my story.

    • I doubt that dealing with corporate politics is something an experienced entrepreneur can deal with well based on how colossally wasteful it is. Just imagine coming up with great improvement after great improvement only to have it shot down or stolen because that is what fits with someone’s personal agenda.

  • Working on your business at home is probably the worst thing you can do.

    If you’re starting a business, you need to be part of a startup ecosystem – surround yourself with other founders, investors, and mentors. Those people have the combined experience to help you succeed and know what you’re going through.

    If you dont have a strong startup community in your city/town then start one. Go to and start a meetup where you host an event every week of every 2 weeks for entrepreneurs to come and shares their stories or the problems that they’re having. Reach out to local successful entrepreneurs and invite them to speak.

    Once you’ve built relationships with VCs and successful entrepreneurs, make a proposal for them to invest in a co-working space (if one doesnt exist near you) so that all of the entrepreneurs, investors, creative people, engineers, etc have a hub where they can meet each other and build awesome companies.

    Thats what you need to do. Do that.

  • I would highly recommend finding a co-founder as your first order of business. If you can’t make something appealing about the opportunity in front of you to somebody (could be the missions, the money, the freedom, the disruption, the challenge, whatever) it’s not going to get any easier to convince buyers or investors.

    • With friends, after a night of going out. Hehe, I wish it was made out. The VC person who was there is famous in the community.

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