#AskGaryVee: One Entrepreneur's Take on Leadership, Social Media, and Self-Awareness

#AskGaryVee is an almost perfect reflection of it's author, Gary Vaynerchuk. It is fast-paced and world-wise, blunt yet kind, and filled with freewheeling yet well-considered advise. It will get you up to date on everything you should know about social media, but it also gets into the clouds and the dirt of so many other issues. As the book's sub-subtitle suggests, it discusses marketing more broadly, and dives into topics such as "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, and the New York Jets." Left out of that list is wine, the industry in which Gary made his bones—famously taking his family's wine business from a $3 million business to a $60 million business in just five years before he set off on his own (well, with his brother AJ) to start VaynerMedia—but he even devotes an entire chapter to wine at the end of the book.

The book, as you can probably tell from its title, is written in a questions and answer format, drawing from "the most useful and interesting questions that Gary has addressed on his popular show." And there are a lot of questions answered. The book is almost 400 pages long, and there are usually multiple questions on each page. One of the longer answers, though, comes in response how and when to automate, which Gary is not generally a fan of.

Let me be clear: You should never automate your content to pretend you're generating content right then and there—in other words, to help you fake a human interaction. Ever. Especially tweets, for reasons you'll read about below.

 

That does not mean you should never automate, though.

 

Automation is extremely useful when you want to confirm receipt of an online order, a registration or a subscription, or email correspondence from a customer. It reassures people that their emails or orders aren't disappearing into the ether. It offers peace of mind, and that's good customer service. There. Now you know when you can automate. In almost all other cases, don't. Here's why:

 

It makes you look insincere.

 

Automation should not be used to replace human interaction. Even in the case of an automated confirmation email, you should never sign off with your own name. You can sign your company name, or even as "The Team at Insert-Your-Company-Name-Here," but unless you actually hand-type your customer's name and hit the send button, that email is not really from you, and you shouldn't pretend it is.

 

Think about how much it means to get a personal reply from someone in today's world. The importance social media users place on a tweet or favorite from someone they admire, whether its an individual or a company, is huge. Let's say you arrange for anyone who follows you on Twitter to receive a direct message that says, "Thanks for the follow @whoeveryouare!" Now you've led Whoeveryouare to believe that you're actually engaging. But you're not. And that's not only dishonest, it's spammy. Same if you automate a follow on Facebook. I mean really, does it take that much time to say a quick "thank you" in person?

 

The idea that automating human behavior is acceptable in the interest of saving time in a busy world goes completely against all the authenticity and transparency that make the social media age so unique and wonderful. Bottom line: I actually adore automation as long as its intent isn't to trick someone into thinking it was done by a human being in the moment.

There are two other reasons he gives: It puts you at the mercy of others, and it makes you look like an a**hole. (Vaynerchuk does not asterisk him own writing.) To explain how it puts you at the mercy of others, he mentions an incident in which the New England Patriots automated a response to every fan that retweeted a celebratory tweet. He explains how that plan soured on them:

Unfortunately, one of its fans had a horrible user name that I will not repeat here because I know better than to mindlessly repeat such an ugly thing. Because I'm human. But the computer didn't know better, because it's not. And so it created a jersey bearing the offensive Twitter handle and tweeted it, leaving the Patriots to grovel for forgiveness when the Internet went crazy on them.

He also tells a story of friends automated tweets celebrating new product line launches and stating what a great day it was… as the Boston Marathon bombing was unfolding. I'll leave it up to you to discover why it may make you look like an a**hole.

And then you're off to get his advice on overly edited photos on Instagram, what advice he gives to people who want to grow their companies but may not have his outsized personality to do so, and what the best way for a real estate agent to gain trust on Twitter is—all in the next two pages.

There are 157 episodes of The #AskGaryVee show on YouTube. At "12-25 minutes each," it's going to take a long time to catch up if you're just joining in. Think of #AskGaryVee as the analog version that you can take with you anywhere and help get you caught up while you're away from your screen(s).

We have 20 copies available.