Business Tips: Uncomfortable Truths About Being a Great CEO: A Conversation With Michael Ovitz

Business Tips: Uncomfortable Truths About Being a Great CEO: A Conversation With Michael Ovitz

Awesome Tip: Uncomfortable Truths About Being a Great CEO: A Conversation With Michael Ovitz



When you’re the CEO of a company, you deal with enormous pressure knowing that you’re the last line of defense.

My entire day is about putting out fires.

I have to deal with things like HR issues, client problems, even roof leaks in our Chattanooga office…

And I love it.

Really enjoyed sitting down with Michael Ovitz at Summit to talk about what it takes to be a CEO and running a business in a “post-internet” world. Check it out and leave me your $.02 in the comments!

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Gary Vaynerchuk is the chairman of VaynerX, a modern-day media and communications holding company and the active CEO of VaynerMedia, a full-service advertising agency servicing Fortune 100 clients across the company’s 4 locations.

In addition to VaynerMedia, VaynerX also includes Gallery Media Group, which houses women’s lifestyle brand PureWow and men’s lifestyle brand ONE37pm. In addition to running VaynerMedia, Gary also serves as a partner in the athlete representation agency VaynerSports, cannabis-focused branding and marketing agency Green Street and restaurant reservations app Resy.

Gary is a board/advisory member of Ad Council and Pencils of Promise, and is a longtime Well Member of Charity:Water.

Gary is a highly sought after public speaker, a 5-time New York Times bestselling author, as well as a prolific angel investor with early investments in companies such as Facebook, Twitter, Tumblr, Venmo, and Uber.

Gary is currently the subject of DailyVee, an online documentary series highlighting what it’s like to be a CEO and public figure in today’s digital world, as well the host of The GaryVee Audio Experience, a top 100 global podcast, and host of #AskGaryVee, a business and advice Q&A show which can be found on both YouTube and Facebook.

Gary also appeared as judge in Apple’s first original series “Planet of the Apps” alongside Gwyneth Paltrow, Jessica Alba and Will.i.am.

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45 Replies to “Business Tips: Uncomfortable Truths About Being a Great CEO: A Conversation With Michael Ovitz”

  1. Thanks Gary, this one has impacted me personally more than any other vid you've done. It's reassuring to know I'm not the only CEO who thinks about slitting their wrists on a daily basis, that this grind is normal, and that to persevere is actually the win.

  2. [2:52] The statement of the week: "[Entrepreneurs] need to learn how to build a proper container for [their business], and how to merchandise that container".

    Though when you get into "not everyone should be an entrepreneur. You might be happier being #7 at a company" – I would say many people agree, but they feel that they don't have a choice BUT to go the entrepreneur route.

    And the reason I say this is because, yes – many people don't want to be the "firefighter" and take on that massive amount of responsibility (it sounds exhausting).

    But when you work for companies where the company culture is toxic, if not destructive, or you work for your "unicorn company" to find out they're a donkey – how many times can you go through that disenchantment and disappointment before you say, "Fuck it. I might as well do this on my own"?

    Everyone has their reason for wanting to become an entrepreneur.
    For a lot of people, it may be because it's sexy or they want to make a lot of money.
    Cool.
    But for me, it honestly feels like I have no other choice but to, as you say, "die on my own sword".

  3. That was a freakin phenomenal video ….. Gary you never cease to amaze me with your different knowledge …. love how you called him out on his biggest L …. loved even more how he answered…. straight up

  4. Great interview. Had to do a big share on Linkedin just now thanks. LOVED The art of building relationships with everyone as being integral to being a great Producer/CEO – IMHO seems to have been lost to the millenials – Also LOVED that the success of your business story is only in if you get the cultural context right (ie pay attention to the music, popular culture AND who is doing what ALL around you ALL the time) is spot on. Also PAY ATTENTION to the Producers who have been doing this stuff for the past 30-40+ years.:-) We know a few things that will help you. Ah I feel better now. Going back to leading my team. #CEO #Producer

  5. You can really tell just how much Gary respects Michael. He never cuts him off and in fact lets Michael cut him off whenever. It's an insane contrast in comparison to most other convos with GaryVee.

  6. Started 9 months ago with 0 subs, now 9 months later I'm at 600, the grind has been slow and steady but each day brings me closer to my dream. Though there are some points where I'm just contemplating if I'm doing enough.

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