Takeaways: The 9 Pages I Dog-Eared in #AskGaryVee

I have highlighter ALL OVER this book. It’s packed with delicious nuggets of wisdom in an easy to digest Q&A format. Of the three-hundred-and-some pages I’ve colored in with highlighter, I dog-eared nine pages for quick reference.

Book & Author

Title: #AskGaryVee: One Entrepreneur’s Take on Leadership, Social Media & Self-Awareness And Winning, Marketing, Venture Capital, Arbitrage, Digital Media, Influencers, Company Culture, Start-Ups, Attention, Content, Management, Empathy, Legacy, Parenting, Family Business, Crushing, Storytelling, Thanking, Jabbing, Right Hooking, Hustling, & the New York Jets

Gary Vaynerchuck entrepreneur, tech investor, CEO of VaynerMedia, public speaker, lots of other stuff…


Clouds and Dirt: Page 2

GV’s Cloud Commandments:

  1. Bring value to the customer
  2. Provide 51% of the value in any relationship
  3. Work for lifetime value
  4. Smart work supplements hard work, but it can’t replace hard work
  5. People are your most important commodity
  6. Patience matters
  7. Never be romantic about how you make your money
  8. Try to put yourself out of business daily (push harder and try more things)

Be a practitioner (dirt) and work on executing towards the commandments (clouds). Clouds and dirt go hand in hand. Ideas won’t get you anywhere without executing on them. Execution is meaningless without ideas.

No matter what business you’re in, you have to be a business person first, especially if you are an entrepreneur. As a graphic design contractor, I can’t just be a good designer. I have to run all parts of my business, which includes billing, selling, writing/approving contracts, ect. You gotta make sure you’re making enough money to do business.

Hustle: Page 89

How to hustle faster:

  1. Shorter meetings (the shorter the meetings, the better people prioritize)
  2. Don’t get lost on the weeds or get caught up in non-productive fluff
  3. Don’t be afraid to try things
  4. Stay grounded and straight-forward; don’t romanticize
  5. Don’t get paralyzed or slowed down by aiming for perfectionism
  6. Always keep moving

Content and Context: Pages 99, 119, 124

All companies should think and act like media companies. Content needs to:

  1. Appeal to the heart
  2. Be sharable
  3. Be native to the platform on which it appears
  4. Be noticeable

It’s hard to break through the noise of all the other content being produced. If you want people to know that you exist, take the time to produce good content regularly. Every time you post a new piece of good content, you are creating another opportunity to be found. The content doesn’t need to be your standard of “good,” it needs to be your audience’s standard of “good,” so experiment and see what they like. The more you produce content, the more efficient you’ll become at creating it.

Some businesses are relying on automated messaging and post creation services to increase their activity. DON’T. Automation shouldn’t be used to fake human interaction. Automated messages built to look like real human interaction often feel insincere and can damage your followers’ perceptions of you.

Jabs and Right Hooks: Pages 131, 133

Jab | verb

The content that entertains and/or informs; the relationship building content.

Right Hook | verb

The content that brings in the sales; the ask that says: “Buy my stuff.”

Lots of people are great at making lots of jabs, but are afraid of making the the right hook. Don’t be afraid. People expect the ask. Nobody who follows a company, entrepreneur, or content creator is blindsided by a sales pitch. Don’t be shy. Just ask. So long as you’re upfront with the ask and have been providing value, you’ll see positive results.

Effective right hooks look different across platforms. Know your audience on each platform and write posts customized for how they prefer to engage on each site. Study up on the promotional capabilities of the platforms you use. (Gary V swears by Facebook ads.)

Don’t just post on social media. Listen on social media. As Gray says, “Use Twitter Search as your bionic ears.” Check out what people are talking about and join their conversations. By listening to other users and responding to their posts, your spurring them to take interest in you. Engaging with people in a meaningful way prompts them to look at your profile to see what you’re about.

Create opportunities for discovery through your content. Not everything you post has to be related to your product. If you’re a car dealer and you’re participating an a walk for breast cancer, talk about it. People like that stuff. It helps them get to know you better.

LinkedIn is the best business professional contact book out there. It’s a great place to search for your target audience using business specific criteria, like titles. People also segment themselves by joining LinkedIn groups, which you can search and target. Find the groups that your audiences join and contribute to those group conversations.

***Notice that I use words like “contribute,” “join,” and “participate.” That’s because you should be a seamless addition to their conversations. Don’t just jump in with your sales pitch. People don’t take kindly to pitches that disrupt the flow of their conversations or feed.

Influencer Marketing: Page 195

Spend more time figuring out why the content you put out there is succeeding and use that insight to make better content. If the performance of your content plateaus and engagement becomes consistent, that’s when you should try influencer marketing. Measure your influencer marketing efforts against your plateaued content measures to judge success.

Partnering with a content creator is just that: a partnership. If you’re partnering with a popular content creator, remember that they are popular for a reason. You’re paying them to create content around your product using their voice and perspective of your product, so trust them do their thing.

Management: Page 244

The for thing Gary V looks for in a new hire:


Know that there is no immediate return in business.

Word is bond

Follow through on your commitments. Every time you do this, you are ranking up in people’s perception of you. When people trust you, they are more likely to advocate for you or accept your ask.


People make mistakes. What distinguishes a failure from a return to grace is your response to the mistake. Is your immediate reaction to look for blame or solutions?


People who show genuine gratitude tend to be more motivated to show their gratitude in their work and are nice to work with.

I’m at an early stage in my career. If I reread this book ten years from now, I’ll probably dog-ear a different set of pages as the insights in this book change in relevance to me. If you’ve read #AskGaryVee let me know your “dog-eared” pages.


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