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The Hardest Thing About Starting VaynerMedia

By December 10, 2014September 4th, 2022No Comments3 min read

Joining the agency world with zero experience didn’t make me nervous.

I wasn’t worried about starting a new business from scratch. I wasn’t worried about my lack of knowledge of the industry. Those things were just not on my mind.

So, what did make me nervous?


The typical things you might expect me to have been nervous about did not apply. I was confident in my decision to leave my last business, and confident in the business partner I found in my brother. For me, the hardest thing about starting my agency VaynerMedia was being crippled by thoughts of what could have been. Options. Over the first nine months of the agency being open, it was very difficult for me not to think about the fact that there were 800 other things I could have done.

Did I pick the right thing?

VaynerMedia started in 2009. My daughter Misha was born in 2009. My second book Crush It came out in 2009. All those other things were happening. So when people ask me what the hardest thing about starting VaynerMedia was, I tell them that the hard part wasn’t starting it, the hard part was asking “Is it a good use of my time?”

I know everyone reading this will know exactly what I’m talking about. We are all crippled by this same thing. Kids when they pick a college. Managers when they are hiring. Entrepreneurs with investments. Not knowing if the decision you made was the right one is a huge burden, and I get that. And I definitely have my struggles with looking back, right?With all the options available to me, I’m always questioning if I have chosen the right path.

Here is my advice: at some point, you have to put your big boy pants on and say “I’ve made this decision” and you move on. The “buyers regret”, or remorse, or thinking “Did I do the right thing” is never going to be helpful. Because guess what? Every option will get you SOMETHING. That something could be a return on an investment, or it could be a lesson learned. Doesn’t matter. You’re never going to be left with zero results. That is my advice to you. Suck it up. Make the call.

Because guess what? To be crippled by options is a blessing and a half.