Many of you know that this month marks iClick’s ten year anniversary. I started iClick on Dec 31, 2001 in my Seattle apartment with 14 credit cards, a computer connected to dial-up, and a half-baked idea to import digital cameras.  I could use this opportunity to reminisce but I did that already at our holiday party.  I could tell you about what I learned but I fear it would sound like regurgitated entrepreneurial rhetoric.  I could tell you about all my successes and how I overcame adversity but you would probably stop reading.  Instead I want to tell you about something that leaders rarely share in public.  I want to tell you about my fears and insecurities.  Here goes… I was scared to fire employees.  I don’t believe anyone gets over the fear of having to fire someone.  The first person I let go was a salesman.  I procrastinated four weeks before doing it.  Afterwards I went home and cried.  I don’t cry anymore but I’m still scared of having to let someone go.  Never believe anyone who says they like to fire people.  They have either never done it or are lying.

I was scared of failure.  Not the act of failing but the thought of having to tell people that I failed.  When I exposed myself and took the risk to start a business I feared what people might say behind my back.  In person they were supportive but I suspected they left and said, he’s probably going to fail.  I feared I would prove them correct.

I was scared to say no.  For fear of not seizing a potential opportunity I said yes to meetings with people I shouldn’t have, sales to the wrong customers, and partnerships that didn’t make sense.  I was insecure and I didn’t have the strength to stand by my convictions.

I was scared to ask people to invest their money.  In 2005 I raised money from Seattle angel investors to help iClick grow.  I was great at pitching the business and getting people excited.  I never had the balls to simply ask them if they wanted to invest and if so, how much.  I waiting for them to say so.  Asking for money from investors is the same as asking for the sale.  Good salespeople know how and when to ask for the sale.  I don’t have that knack because I’m afraid.

I was insecure while alone at organized networking functions.  I still am.  I don’t have the confidence to walk up to someone and introduce myself.  I simply don’t know how to start the conversation so I don’t even try.  Instead, I stand nervously hoping someone will talk to me.

I was scared when I left Seattle last year and moved to Boulder.  I left my city, my company, my culture, my friends, my desk.  I left everything.  I didn’t just build a company, I built a life for myself.  And at that moment I was saying goodbye to that life that I conceived ten years ago.

I am scared now that I can’t do it again.  That the first time was just a fluke.  That I’m not smart enough to build another success.  That the “I Told You So’s” will be right there when I fail on whatever that next venture is, whenever that is.  I am scared, but not deterred.

It’s OK to be scared.  We all are.  Don’t ever let that deter you from reaching for your dreams.

(Cross-posted on Lon's Blog).