My Favorite #AskGaryVee Takeaways and Excerpts

“Gary Vee is a douche man. How can you like that guy?” a friend once asked me. “Have you seen VaynerMedia’s Glassdoor ratings? Nobody likes working there.”

Maybe Gary is a douche… Hell, maybe I’m a douche and that’s why I like him. I don’t know.

I know I still watch clips of his keynotes to re-energize me when I’m in a rut.

I also know that Gary has been very successful in many, many business endeavors.

So, being objective for a second, if a very successful entrepreneur wrote a book (#AskGaryVee: One Entrepreneur’s Take on Leadership, Social Media, and Self-Awarenessanswering thousands of questions about navigating the emerging business world — that’s probably worth the cost of the book, right?

I tend to think so, but feel free to read a few of my favorite quotes from the first three chapters below and decide for yourself.

Smart work will never replace hard work, it only supplements it. – Gary Vaynerchuk

Gary Vaynerchuk's New Book #AskGaryVee

Clouds and Dirt

You want to be an equally good architect as you are a mason. You’ve got to be able to simultaneously think at a high level and get your hands dirty.

On What the Middle Is and Why It Sucks:

The middle keeps everything going the way it always has. The clouds and the dirt break things. All the best apps, companies, and products have broken the way we live life, transformed how we communicate, and changed our day-to-day. Good products evolve us.

The Importance of Having a North Star/Long-Term Vision:

You will stop stressing the dumb little shit day in and day out because you’re playing the big game.

On Industry Awards:

Awards are an energy sucker away from what matters.

On Prioritizing a One-Person Business:

Your first priority is sales because it generates cash, and cash is what allows you to do everything else.

Starting Out

There are two core things that bring people value: 1) entertainment, and 2) utility.

On Making Hard Decisions:

You made your decision for a reason, so trust your judgment. There’s no point looking back. Even if you discover you made a mistake, you’ll be okay, because every option will get you something. It might be return on an investment, or it might be a lesson learned.

On Adding Value to Forge the Right Partnerships:

Spec work. Providing your service or your product for free is a great way to build up points you can cash in later.

On on How to Overcome Complacent Companies Hiring the Same Firms:

If your work is great, that becomes your reputation, and that becomes the gateway drug to bring in business to your sales funnel. You may call the incumbents lazy, but I call it an earned reputation.

On the Biggest Obstacle to Success: Lack of Time or Lack of Money?

The real reason why you stop is not that you don’t have time or money, but that it’s hard.


The American university system has lost its value proposition in face of the speed and intensity of the current business marketplace. (Ed. note: I think this is absolutely true for business, not so much for medicine or engineering. See also: American Education – You Deserve Better)

Don’t be a student. Be a practitioner.

On Why Parents Insist Their Kids Go to College:

They’re still wrapping their own ego up in their children’s accomplishments.

Family Business

Cautionary Advice:

One of the best ways to go out of business is to make emotional decisions.

On Following in Your Footsteps:

Our job isn’t to prepare children to live our dreams, but to live their own.


On the #1 Lesson You’ve Learned As a Father:

The love we feel for our kids really is something bigger and more powerful than anything in the world. DNA is no joke!

On Investing in Rich Kids:

I’m not going to care if you were born rich. I only care if you were raised lazy.


On the One Tangible Thing People Can Do To Change Their Lives:

Hustle. It’s hustle, not talent, that is the differentiator between entrepreneurs who succeed and those who don’t. I have never seen anyone increase his or her natural talent, but I have seen people transform themselves by increasing their hustle.

On Being a Morning Person:

I’ve never really understood why it would be an advantage to be a morning person, or why morning is valued more than other parts of the day. Just work as hard as you can when you are working, and rest when it’s time. It’s not about how much you sleep. It’s about what you do while you’re awake.

On Working Faster:

It takes practice. Train yourself to do a little bit more in each hour than you normally would.

On Hustling Through Sickness:

Coming in when you’re sick doesn’t show dedication, it’s selfish.

Content and Context

On The Way to a Consumer’s Heart:

The rules of good storytelling have remained the same for business since the beginning of commerce.

On Thinking Like a Supermarket:

Supermarkets know you came for essentials so they put the milk and eggs far away from the entrance so that you have to travel the whole store to get what you came for. Along the way they try to show you endcaps and displays of items to raise your bill, but they don’t block the milk from you or make you go downstairs (i.e. give people what they came for, but use content to sprinkle added value).

On Pleasing Everyone:

What alienates me from one person is probably the very thing that draws someone else with a different sensibility to me.

Jabs and Right Hooks

On Having No Expectations:

How many people do (anything) without any expectations in return?

Very, very few. Be one of those few. When you have no expectations people can sense it, and funny enough, the absence of pressure or obligation actually makes them want to reciprocate.

On Closing:

Heart, Brain, Wallet. Every time.

The Platforms

On Why Marketers are Afraid of Snapchat:

Most marketers suck because the suspicion and reluctant with which they approach it (Snapchat) is the same they have for every new app. It’s why they’re late to the party every freaking time and then spend an inordinate amount of money and effort scrambling to catch up once they get there.

On Traditional Media:

Traditional media isn’t what it doesn’t serve a purpose, but that its overpriced for the limited audience it reaches.

On Paying For a Course to Learn More:

The more you practice an analyze your results as you go, the better you’ll get. Being a practioner is the only way to achieve meaningful success. We live in a world of headline readers and shallow pundits. I want you to be different. Go deep.

Stop With the Excuses!

On Creating Content for a Boring Product or Stale Industry:

There is no boring if you tell your story right.


Gratitude is my weapon in my day-to-day life.

On Non-Profits Asking for Donations:

Most of the nonprofits that ask me to help them assume that I’ll be compelled to give my money or use my clout on their behalf just because they’re working for a good cause. But when my time is limited, I’m going to focus my attention on organizations that have bothered to build a relationship with me, not the ones who approached with their hands out.

On Using Social to Promote Non-Profits:

For NGOs and charities to succeed in social media, they have to do what all the for-profit businesses out there are doing — hustling, listening, creating dialogue, solving problems, building relationships, and storytelling.


On the best way to solve problems:

Don’t ever start offering solutions before asking tons of questions.

On Complaining:

Problems happen. Life isn’t fair or perfect. Complaining fixes nothing. Only taking action does.

On the Universal Rule Gary Would Teach Everyone:

Depth matters more than width.

Go deep. Reach out, provide value and be there.

On Staying Motivating:

Gratitude is amazing fuel.

On Keeping Others Motivated:

Some people need to be constantly challenged or they get bored.

On Where to Focus:

Betting on your strengths might be the most underrated strategy in modern business. I’m much more interested in doubling down on the two things you’re good at instead of the one where you’re behind.

On the Two Mandates to Running a Business:

Build teams and sell stuff. Anyone who’s good at both is in a position to succeed at the helm of a company. Any company.

On Leaving a Legacy:

I’ll be judging my success by how many people I think will come to my funeral, not how much money I ultimately make.


What Makes a Good Manager:

The ability to reverse-engineer every person that works for you and put him or her in a position to succeed at the task for which they’ve been hired.

On What Agencies Should Prioritize:

Their employees first, a client’s customers second and the client last.

On Making Culture (and Your People) a Priority:

Business is business when it comes to financial or contractual negotiations, but not when it comes to deciding what happens to the human beings who make your business run.

Gary’s Best Time Management Tip:

Learn to say no to the things that keep you out of the clouds and dirt.

How Do You Make Staff Meetings More Productive?

Cut them in half.

Gary’s Favorite Interview Question:

“Where do you want your career to go?”

By giving people opportunities and helping them achieve what they want, I keep my relationships with my employees positive and open. Such a positive environment not only makes it hard for people to leave, it ensures I always know what’s going on.

Specialist or Jack-of-all-Trades?

Many would argue that by trying to be good at many things, you’ll never master anything. Bullshit. If you work hard at trying to be good at many things, you’ll get good at many things.

What 3-4 Values Do You Hold Highest in Life?

  1. Patience – Success takes time.
  2. Word is bond – Stick to your commitments no matter what.
  3. Empathy – Listen. And look for solutions, not someone to blame.
  4. Gratitude – Don’t take anything for granted.

How Do You Push a Team Beyond Their Best?

By listening, getting to know their ambitions, and being supportive in all their endeavors, even if they don’t necessarily benefit you. Now, you want to do that so incredibly well, and instill such a sense of family and loyalty, that your team would do almost anything rather than let you down.

On Delegating:

You’ve got to know when good enough is good enough. Let the bright, interesting people you hired do their jobs and make yours easier. It takes humility to accept you’re not as unique or indispensable as you think, but it’s also freeing.

On Hiring Slow and Firing Fast:

I don’t think what’s most important is to fire fast, but to fire well.

On What Makes a Good Hire:

Empathy, self-awareness, respect for others, amazing work ethic, and patience.

On Documenting Policy, Procedure and Process:

There is no business on earth that won because it had a supertight handbook. Work on building your values and culture. Make sure everyone knows the mission of the company, where they’re going, and why.

On Getting an Employee Inline:

Managing is a never-ending 365-day test-and-learn. You don’t want to get into the habit of using one move (tactic) over and over. It’s kind of like medicine; if you use it too often, it stops working as well.


On Horses (Companies) and Jockeys (Founders):

When looking at a horse, I’m looking for companies that are built on concepts or ideas that are only about two to three years away from hitting mass consciousness.

At this point in my career I am spending more and more time vetting the CEO and team. I want to know are they self-aware enough to team up with people who fill out their weaknesses. I also want to know if they’ve got the stomach for business.


Gary’s Billion-Dollar Idea:

A formula made up of gratitude, empathy and self-awareness.

On the Easiest Way to Become More Self-Aware:

There’s one hack, and it’s asking people straight up to tell you your strengths and weaknesses.

They Key?

Get yourself a thick skin.

On Overcoming Your People-Pleasing Nature:

You can give, give, give all you want, but if you never step up and ask for something back, you’re not going to win.

It’s a tremendous personality trait to want to make others happy. Just don’t forget to look out for yourself.

Public Speaking

Why Gary Doesn’t Care If You Care About His F-Bombs:

If you’re operating at such a micro level you can’t get beyond my language to hear the bigger message I’m trying to communicate to you, you’re just no someone I want to do business with or take on as a client.


On Increasing Your Income and Brand With Limited Hours:

Your talent is what it is, but the level at which you increase your income and brand is limited only by the scope of your ambition and willingness to hustle.

On the Fallibility of Planning:

You can strategize and plan ahead all you like, but you’d better be ready to adjust and improvise.

Entrepreneurs need to have the emotional composure and the intestinal fortitude to make real-time adjustments and come back from the brink.

On Gary’s Favorite City in the World to Drink Wine:

Wherever my friends and family are. My happiness is always about the who, not the where.

Gary’s Dating Advice:

Better to experience the brief, temporary pain of rejection than to live forever with sad regret for all the things you were too scared to do.

On Automating His Position to Just Spend Time With His Family:

Absolutely not. I would suffocate if I couldn’t work to create the things I want to create. I love the process, the grind and the climb. Most young entrepreneurs want the stuff–the watches, the cars, the planes, and the bling. I just want the pain, the gratitude, and the happiness that come with the work.

On the Importance of People

Guess who you meet on a climb? People. Many on the same route as you. Find those who fascinate you, who challenge you and who help you look forward to getting started every day. Treat them well, provide them with value, show them why you’re worth keeping around, and you’ll get tremendous return. I find the individuals I think I can jam with for the next fifteen, twenty, thirty years professionally, and I bring them into my circle to make the, the next generation of operators.




In the spirit of transparency, I received an early copy of #AskGaryVee in exchange for helping to spread the word about the book’s release.

That said, I would never endorse a book here, on my blog, if I didn’t think it would add value to all of you. I didn’t receive Gary’s book from the publisher in time to finish it before today’s official launch so all I will say is that, based on what I’ve read thus far, I envision Gary’s advice and answers in the book to be worth at least the $18.00 required to purchase the book.

I look forward to finishing the book and updating this review with more great takeaways and insightful excerpts.

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