I think I'm about to create the same failure that I once did, by doing too may things at once, and it scares me. 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 very heavy in operations mode with VaynerMedia and other companies that we're incubating, like Resy. I also 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.
Once I left Wine Library, I was ready to go "play the field." This is where things got crazy and I had my hands in everything, from books, to online shows, to building wine-focused social networks. The truth is though, is that I can't apply the same principles when I'm operating a business versus when somebody else is and therefore I need to be smart in choosing my battles.
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's some great product people and some great marketing and sales people out there, but there's 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.
This is part of a Q&A session I did with the students of Cornell Tech Program. For more, check out the playlist here: https://www.youtube.com/playlist?list=PLfA33-E9P7FAwwMY6gqBd2pc7m-qjcpr-

Gary Vaynerchuk is a New York Times and Wall Street Journal Best-Selling author, self-taught wine expert, and innovative entrepreneur. Find more at http://garyvaynerchuk.com
Jab, Jab, Jab, Right Hook is now available on Amazon! http://bit.ly/jjjrhamazon

11 thoughts on “My biggest failure”
  1. Avataaar/Circle Created with python_avatars Harriot Hawkins says:

    gary whats the most amount of money you lost in a deal also how and what could you have done different ?

  2. Avataaar/Circle Created with python_avatars MakingThisTrend says:

    Can we make this CC please.

  3. Avataaar/Circle Created with python_avatars ArchimedeanEye says:

    legs

  4. Avataaar/Circle Created with python_avatars Craig Cherlet says:

    People are the foundation of any company and unfortunately good help is still very hard to find.

  5. Avataaar/Circle Created with python_avatars Glenda Siagian says:

    Awesome video. Very insightful. Thanks *****ย 

  6. Avataaar/Circle Created with python_avatars CYTROXIAN says:

    This 3 minutes… Incredible! Scale the unscalable….

  7. Avataaar/Circle Created with python_avatars David Howell says:

    This looks like an entrepreneurial AA meeting lol

  8. Avataaar/Circle Created with python_avatars Mechanic says:

    Interested to watch the rest of the series of videos, but as Jiftuq noted, they are marked Private so we cannot view them.

  9. Avataaar/Circle Created with python_avatars Ouss says:

    vids are private

  10. Avataaar/Circle Created with python_avatars Countdown Social says:

    I've always been amazed with your ability to time manage and accomplish so much, especially considering how much time you still spend with family and at Jet games.

    You have an excellent track record of being the first on "the next big thing" before anyone else, do you think that you've lost some ability to see the beginning of potential game changers since you're occupied with seemingly bigger fish? To rephrase, do the little things get your attention before going mainstream like they did ten years ago?ย 

  11. Avataaar/Circle Created with python_avatars Luis Biggs says:

    I like your point about HR being paramount. And that if you don't have retention, the loss of energy and IP becomes a waste of time.ย 

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