I’m Not Going to Repeat My Mistakes. Here’s How:

There is a possibility that I am about to replicate one of my biggest failures, and that scares me.

Let’s back up. Once I left Wine Library, I was ready to go “play the field.” That was where things got crazy and I had my hands in everything from books, to online shows, to building wine-focused social networks.

It didn’t work.

Other people were operating those businesses, and the truth is that the principles I apply to businesses I operate can’t be equally applied to the ones I don’t. I learned that, and I learned that I need to be smart in choosing my battles. That’s why investing is great for me. I can leverage my skill by writing checks for companies I see potential in and apply my entrepreneurial tendencies when I can.

Right now, I’m in very heavy in operations mode with VaynerMedia and other companies that we’re incubating, like Resy. I had a lot of success in the “box” space with both BirchBox and BarkBox, and now we’re working on Faithbox, which is more tailored to the social-good side of things.

This time around though, the partners are a crucial component to my decision process. The reason I built an agency wasn’t to build an agency. What I’m really doing is grooming operators, which I think is the biggest thing that’s missing in our space. There are some great product people and some great marketing and sales people out there, but there are simply not enough people that know how to actually run a business.

My style is a little bit different than others in that my number one principle is Human Resources. EVERYTHING falls from HR. I work to avoid the turnover and create an environment where the culture breeds happiness. I need operators that are assassins, but are also motherly and caring. And the only way I can figure that out is by being as involved as possible in HR.

And so, my intentions are to groom them and put them in my projects and investments in order to scale the unscalable — which I believe, is humans. And with a good set of humans around me, hopefully I won’t re-create the events of 2009.

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Thanks for reading. Quick question: Have you checked out my new podcast yet? It’s on iTunes!