50 Lessons I’ve Learned From 50 Episodes of #AskGaryVee Show

askgaryvee_showWhat is your best way to become smarter?

To me it’s undoubtedly a chat with a person who’s a hundred times smarter than me.

“If you’re the smartest person in the room, you’re in the wrong room”, – absolutely love this quote.

But unfortunately the smartest people in the world are too busy to spend time chatting with you, even if that’s just a few seconds.

And that’s the reason I love #AskGaryVee show so much.

The #AskGaryVee Show

This show is basically a Q&A session between Gary and just about anyone, who will tweet him a question using #AskGaryVee hashtag.

The vast majority of questions are about marketing, social media, and entrepreneurship, but Gary really has an answer to just about anything :)

And this is truly an amazing chance to learn from Gary, who’s undoubtedly one of the smartest marketers in the world.

You actually ARE getting smarter just from watching this show, and here’s what I’ve learned from it…

50 Lessons I’ve Learned From 50 Episodes of #AskGaryVee Show

What goes below is a selection of my favourite quotes and takeaways from this show.

I made some of the quotes “tweetable” in case you would like to post them on Twitter.

Sometimes I would throw some of my own comments, if I feel that context is required; and sometimes I would embed the actual video, if I think that you ABSOLUTELY have to watch it.

By no means this article is designed to replace those 50 episodes of the show. This is rather a “trailer”, that should motivate you to go watch all of the past episodes.

Subscribe to Gary Vee’s YouTube channel if you want to get notified of the new episodes (you can also subscribe with iTunes).

Lesson #50: On white lies

“If you feel like you’re growing into it within weeks or maybe maximum a coupe of months – I think that’s ok.”

[watch episode #50]

Lesson #49: On business

“Any time you can sell ahead of your expenses – you do it! One of the biggest reasons so many people go out of business is they don’t know how to manage cashflow.”

[watch episode #49]

Lesson #48: On competition

“Do I know what my competition is doing? At some level. A little bit. Contextually. But I never go deep. It’s all “headline reading”. I know who’s making some buzz and some noise. But I truly believe, that the biggest mistake so many companies and entrepreneurs make is “looking around them”.

[watch episode #48]

Lesson #47: On accents

“Do I think that people look at accents as a sign of inferiority, not as much intellect – I absolutely believe that to be true. On the flip-side, I think, Tim, my friend, you’re looking at the negative – what about all the people who DO have accents? As a “marketing person” you’re speaking to entrepreneurs and many of them in this amazing country DO have accents.”

[watch episode #47]

Note from Tim: That was my own question to Gary and if you want to see how I look/speak – just check the video below.

Actually the question about accents is relevant for many people, not just me. I even got a few emails from my readers (who considered me a US person) asking if I thought it was possible to tap into American market while leaving in Europe, Russia, India, Philippines etc. And I think that’s absolutely possible!

Go watch a speech of an american idol, with terrible Austrian accent.

Oh.. and I’m actually from Ukraine, not Russia. And this didn’t matter to me until some recent events.

Lesson #46: On getting mentors

“You want something so amazing from somebody, which is their time and their energy, and your opening question to that person is “Hey, can you give it to me?”. You want a mentor? Why don’t you provide that mentor with so much upfront value, that you guilt her or him into mentoring you.”

[watch episode #46]

Lesson #45: On new marketing tactics

“People fall in love with the way they’ve made their money, because it’s working right now. They get romantic and don’t try new things. Every person should always be spending between 5-20% of their money or their time on new and innovative things”

[watch episode #45]

Note from Tim: No matter how good the tactic works for you right now, there’s always a decay. That is why you should innovate and try new things or you’re going to fall behind your competition.

Lesson #44: On kids & Social Media

“It’s amazing to watch 13-year old girl behaviour where they’re spending 45 minutes on the lightning and the angle of an Instagram photo. And then, if it doesn’t get enough likes in the first 3 minutes – they take it down.”

[watch episode #44]

Lesson #43: On rich kids

“The reason I think my “rich kids” are gonna be ok, is because if they act too rich-kid’y, I’m gonna punch them directly in their mouth.”

[watch episode #43]

Lesson #42: On time management

“There’s plenty of “damage” between 11pm and 3 in the morning.”

[watch episode #42]

Note from Tim: Many people complain that they don’t have enough time to build their business and come up with tons of different excuses. Well, I loved Gary’s take on this so much, that I’m actually embedding this episode here. The rant starts at 4:37.

Lesson #41: On meetings

“The best way to make meetings more efficient is to cut them in half. People will fit 10 pounds of crap into a 10-pound bag. You give them a 15-pound bag, that’s what they fit it into.”

[watch episode #41]

Lesson #40: On advice to your younger self

“Hook up with more chicks and not work as many hours… while you’re 21.”

[watch episode #40]

Note from Tim: What Gary meant to say here is that if you’re this young – you should allow yourself to have a little more fun, you’ll have your chance to accomplish things as you get older (I guess a lot of people would love to argue that).

Lesson #39: On micro-management

“The thing I hate more than anything in the world is “micro-management”. I want to kick “micro-management” in the face.”

[watch episode #39]

Lesson #38: On Social Media ROI

“It’s never been more easy to prove the ROI of Social Media than it is right now, because you could just link it to the .com attribution. You cannot do that for print, or radio, or television. You just can’t.”

[watch episode #38]

Note from Tim: I’ve seen too many bloggers obsessed with their follower counts and retweets. But that is not ROI, you guys. Leads and sales – THIS is what ROI is all about. And actually, the whole episode is so awesome, that I just have to embed it in full:

Lesson #37: On first impressions

“The first “taste” that you have with someone, the initial context, that first moment, that first impression… when it is sh*t – you’ve lost.”

[watch episode #37]

Note from Tim: In case you didn’t click the link to watch the full video, I’m going to give you some context. Gary was talking about the automation of your Direct Messages on Twitter once someone follows you. Here’s the thing: there’s no way to make a good first impression with an automated message, especially if you’re trying to immediately sell them on something.

Lesson #36: On PR and Social Media

“PR is very B2B. When you’re a PR person and you’re working with a client, you’re trying to get them press in NY Times, NY Post, ESPN – you’re working directly with a human being who’s the gatekeeper to make a decision. When you’re doing social you’re dealing with all the fans and it’s much more B2C.”

[watch episode #36]

Note from Tim: One more episode that made it to the shortlist of my favourite ones. So here’s the full video:

Lesson #35: On hustling

“To me “hustle” – is maximizing the energy you’re putting into something, making every minute count. “Hustle” – is waking up one day, the day before you die, and realising you gave it your all.”

[watch episode #35]

Note from Tim: If you’ve been following Gary for at least a while, you must know that the term “hustle” is something that he would mention almost every single time he speaks. So it was fun to hear him define what it actually means. You need to see that:

Lesson #34: On building a personal brand

“For the first 10 years of my professional career I didn’t say a damn thing. I did nothing in building the Gary Vaynerchuk brand. I did the work, that allowed me to have the audacity to build the Gary Vaynerchuk brand.”

[watch episode #34]

Note from Tim: Gary seems to be a huge contradiction on this one.

HERE he says that for the first 10 years of his professional career he “didn’t say a damn thing”. What he did was work, that allowed him “to have the audacity to build the Gary Vaynerchuk brand”.

And HERE he says that he kinda regrets that he didn’t “map his journey” and suggests others to start producing content early in their careers.

Both of these pieces of advice make perfect sense to me, but at the same time they seem contradictory, so I feel I’m missing something.

I even reached out to Steve Unwin to see if I can get an answer from Gary. And Steve liked the contradiction a lot and asked my permission to have Gary answer this in public:

hopefully Gary will answer this in one of the future episodes

hopefully Gary will explain this in one of the future episodes

Lesson #33: On exposure

“Even in the world where you do not have a huge audience, you have a way to bring value to somebody. If you can figure out how to do that and then leverage that value for them to give you what you want (which is exposure) – you will win.”

[watch episode #33]

Lesson #32: On landing interviews

“People that have leverage and have fame – they like to TALK.”

[watch episode #32]

Note from Tim: I think this particular episode is very relevant to bloggers and content marketers, so it should be embedded here:

Lesson #31: On automation

“The way to humanize automation is the follow-up.”

[watch episode #31]

Lesson #30: On listicles

“I love the customer, I don’t love anything else. So as long as the customer is enjoying it, clicking it – then that’s what it’s going to be.”

[watch episode #30]

Lesson #29: On watching successful companies

Here are three tangible things you should do every day:

  1. Read Jason Hirschhorn’s newsletter;
  2. Read Techmeme;
  3. Go to iTunes AppStore and look at the top 150 paid and free apps.

[watch episode #29]

Lesson #28: On project management

“The best way to be a great project manager and get things done is to be a great listener instead of talker. The way you win is by listening to the people up to why they’re not doing well. If you actually apply empathy and understand what’s going on there, you become known to everybody as the project manager that gets it.”

[watch episode #28]

Lesson #27: On Twitter following

“There’s an absolute strategy on following a bunch of people on Twitter. It is about giving them something they want. And when you give people something they want – they appreciate it!”

[watch episode #28]

Note from Tim: This strategy is obviously very relevant to Gary, being a public figure who’s famous enough to make people follow back and then read his tweets.

But what about newbie bloggers? Do other people care about a random blogger who have followed them on Twitter?

Well, if you refer to the famous 1% rule of the internet, the vast majority of people (99%) consume content, and only a few (1%) create it.

If you’re a blogger, you’re one of a few, who is creating content. And your job is to get yourself in front of thousands of content consumers and make them interested in you.

These people don’t get new Twitter followers too often, so they will likely check your Twitter profile once you follow them and if your profile is cool enough – you might get yourself a new follower.

Lesson #26: On failure

“It’s WHO are you afraid to fail in front of. Is it your mom, is it your best friend, is it your sister. That’s the only thing that holds people back.”

[watch episode #26]

Lesson #25: On innovations

“The way I’ve always been innovative is lack of education (and I’m not joking). And two – I look to other industries (just the stuff that has nothing to do with your industry). Because the best way to stay within the zone and not innovate is paying attention to everybody else, cause they are doing the same crap too.”

[watch episode #25]

Lesson #24: On young entrepreneurs

“The problem with young entrepreneurs is that they want “stuff” (fancy cars, private jets). I don’t want stuff. I want the sweat and the pain and the gratitude and the happiness that comes along with the work.”

[watch episode #24]

Lesson #23: On content marketing

“The problem with “Own it, Own it, Own it” is when you’re doing it on your own site – you’re at the mercy of how much traffic you’re able to establish on your own site.”

[watch episode #23]

Lesson #22: On call-to-actions

“There’s a time and the place for a Call To Action, but that isn’t every single time and every single channel, because they you just become a sleazy salesman.”

[watch episode #22]

Lesson #21: On time management

“My tip for time management is to have an assistant who you make the Tzar of your time.”

[watch episode #21]

Note from Tim: I guess this kind of advice can’t be adopted by everyone, since only a handful of people can afford hiring someone to manage their time. But I’ve learned another thing from Gary – see Lesson #13.

Lesson #20: On retaining clients

“The best way to keep clients from not running away from you after they get something out of you is to still have something to give.”

[watch episode #20]

Lesson #19: On public speaking

“You’re only as good as your last talk. Even though I’ve had a great seven-year public speaking career – none of that matters the second I hit the stage for the next time. The way I prepare for a speaking gig is the same way I would prepare for WAR.”

[watch episode #19]

Lesson #18: On content marketing

“Distribution, distribution, distribution. I highly recommend you ask yourself “What are the 100 websites that are the biggest in the world that speak in the genre of my show”. And then literally email them one by one and ask them if they would like to distribute your content.”

[watch episode #18]

Note from Tim: actually I loved the whole episode quite a lot, so let’s just put it here:

Lesson #17: On word of mouth

“There are only two ways to empower your community to buy your product and also spread the word about it:

  1. The product needs to be good. It should be well-worth its money. People will only tell their friends about things that are truly great;
  2. Good old-fashioned honesty. You should be really upfront with them of what you want from them.”

[watch episode #17]

Lesson #16: On business strategy

“The only core strategy I have is “collecting people”. Finding the individuals I think I can jam with for the next 15-45 years professionally. That to me is a global strategy. Who I can do business with as a teammate forever.”

[watch episode #16]

Lesson #15: On principles

“I think human beings overthink shit!”

[watch episode #15]

Lesson #14: On hiring

“Way too many people make decisions on who they fire or hire based on money. They make it the “financial decision”. All MY decisions on firing or hiring are emotional. What is it gonna do to the collective community. If I fire this person who’s so popular internally, because they have great “people skills”, will that hurt everybody else?”

[watch episode #14]

Lesson #13: On giving advice

“What works for me does not necessarily work for you. So many of you do so many things better than I do that it makes me want to vomit on this football. So what you need to do is take a step back and figure out what you’re good at.”

[watch episode #13]

Lesson #12: On doing things for free

“People SHOULD do things for free, for exposure. There is strategy in doing things for exposure that then lead to bigger money in the future. One needs to understand that money is not the only way to pay. Giving people a nap back, the platform, the exposure IS an absolute “monetary” way to compensate them.”

[watch episode #12]

Lesson #11: On education & work

“Most people say “What college did you graduate from?”, not “What was your GPA?”. So you should easily be able to become a solid D-student, or C, or whatever is needed to graduate. Which should give you the flexibility to become a massive YouTube sensation.”

[watch episode #11]

Lesson #10: On luck

“Luck IS part of the equation. But at the end of the day success is really a combination of everything: confidence, skill, hustle, talent, luck.”

[watch episode #10]

Lesson #9: On humour

“Humour happens to be one of the most attractive personality traits. Overall this trait is no more important than the other things people are very attracted to in others: caring, empathy, gratitude, kindness, beauty. It’s just another core tenet, but if you have it – use it!”

[watch episode #9]

Lesson #8: On focus

“Focus on 1 thing and make that 80% of your nut. And then have 20% of complete and utter chaos. This will keep your life spicy and interesting and at the same time allow you to grow this singe thing where most of the focus goes (but this thing might not work for everyone).”

[watch episode #8]

Lesson #7: On taking action

“What is more valuable… enthusiasm or action? The answer is – both! If you’re only about one of these two things you won’t get that much result as if you combine both of them in you.”

[watch episode #7]

Lesson #6: On social media leads

“It’s not always necessary to drive traffic from social media networks where you’re at to your website. If you can get people to leave their email or buy your stuff right from Twitter, why would you want to send them to your website?”

[watch episode #6]

Lesson #5: On public speaking

“If you are not known, you do not deserve to get paid. You know why you get paid to speak? Because you put asses in the seats, because people want to come and see you.”

[watch episode #5]

Lesson #4: On sales

“Biggest piece of advice that I’m willing to give to sales people in this world is ironically “Jab, Jab, Jab, Right Hook”. The truth is – everybody is trying to close too early, it’s just lack of patience, it’s not providing value. Be tactical, but understand the “Religion”, which is: “Provide value upfront”.

[watch episode #4]

Lesson #3: On marketing

“The marketing will matter only if the product is serviceable at some level. Great products always need less marketing and great marketing doesn’t fix crap products.”

[watch episode #3]

Lesson #2: On first customers

“To get the first 10 customers you have to grind. Go to every single person in the world that will possibly buy your thing and ask them to buy your thing.”

[watch episode #2]

Lesson #1: On selling

“Don’t try to convince somebody to buy a fax machine. Go find the people who already “bought in” to the fax machine and just sell it to them. Because if you’re too early in a theory or a business where nobody has “bought in” – you’ve lost.”

[watch episode #1]

Want More of Gary Vaynerchuk?

In case you’ve made it all the way to the bottom of this article, I guess you loved what Gary V. has to say and you want even more.

Here are a couple of my favourite podcasts, articles and interviews mentioning him:

Oh, and I guess you have to know that Gary has published three awesome books on the topics of business and marketing:

Back To You

So did you ever stumble upon any of the episodes of the AskGaryVee Show?

Can you share the most memorable lesson you’ve learned from Gary Vaynerchuk?

I'm the guy behind BloggerJet blog. I'm also the guy behind TweetDis and Content Upgrades PRO. But that's like 10% of what I do these days, as the other 90% is devoted to doing marketing for an awesome SEO toolset called Ahrefs.

10 Comments

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  1. WOW, great article and thank you for the kind mention…I am honored!

  2. Hey man!

    GREAT list and thank you for sharing. Huge fan of Gary and I love his special style of podcasting (to name the least).

    Top notch and shared! #BOOM!

  3. Hi Tim,

    I intend to meet this guy on Saturday at the Wine Store; it’s right by my hometown in NJ. So excited!

    Real gems here!

    I like to talk and it hasn’t hurt me. Just last week I spoke to a class at NYU bout blogging from paradise, and talking like mad helped me land the gig. Of course I promote others super freely too, to open doors for myself, as when you give, you get…..but overall, don’t fear talking, engaging, asking and answering questions, and promoting yourself to make things happen online.

    Thanks Tim!

    Ryan

    • Tim Soulo

      Hey Ryan! So did you meet with Gary eventually? :)

  4. Great article Tim…I love all the different quotes and insights. My fave is #48:

    “Do I know what my competition is doing? At some level. A little bit. Contextually. But I never go deep. It’s all “headline reading”. I know who’s making some buzz and some noise. But I truly believe, that the biggest mistake so many companies and entrepreneurs make is “looking around them”.

    It can be a killer to get too caught up in what everyone else is doing….

  5. Hey, nice article bro :)

    • Tim Soulo

      Hey, nice comment bro ;)

  6. Great Article Tim, love how you create your articles, do you mind if I will copy your style on my blog one day or another? Hahaha, just joking… or maybe not :D However. I had never heard about Gary before, thanx for sharing this amazing experience!

    • Tim Soulo

      Hey Andrea! You are free to copy my style, because it will be YOUR own copy :) The Beatles were copying others for a very long time, which helped them to find their unique voice!

      never be afraid to copy someone ;)

  7. James

    Great quotes, man! ;)

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