
Another 50 chunks of business & life advice I noted down from Gary Vaynerchuk’s #AskGaryVeeShow (part 2)
About one year ago (almost at the exact moment) I posted my first ever Medium post, called “50 business and life gems I distilled from 9 hours of watching Gary Vaynerchuk answer questions”.
I started taking notes when watching Gary Vaynerchuk’s new YouTube show #AskGaryVee, and that resulted in a longread filled with Gary’s advice on business, life, stuff, social media, and on being an entrepreneur.
And then 2015 kicked off.
Gary started putting out content as a raging m*therf*ucker. And I started pushing up my hustle, which resulted in less time for me to watch his show.
But! I caught up.
Well… sort of. I finally made it to episode 100, but Gary already made 172 :-)
But hey, I present to you with pleasure: Gary’s best advice from episodes 51 to 100!
Extra tip: if you bump into a question, statement or piece of content you want to know more about, I strongly suggest to go watch the related episode on YouTube. Context, you know :-)

PS: Gary had the bright idea to… write the #AskGaryVee book! You can pre-order it here on Amazon (non-affiliate).
(Gary, if you read this, I’m right-hooking you right now: if this and my other post bring any value back to you, a signed copy of the book will make me very happy :-))
Let’s go!
#AskGaryVee Episode #51
On being a jack of all trades:
“There’s always room to get better in as many things as possible. You need to expand your arsenal because you’ll never know when you’ll need to tap into more than one skill. I’m a firm believer in the importance of being a ‘jack of all trades.’ It’s speaks to your agility and your ability to offer a number of benefits to a certain situation when the time calls for it. You can always get better.”
#52
On first impressions:
“Words are great, but energy is whole different game.”
On how certain platforms (like G+) that ‘fail’ can still be useful:
“Nothing is ever dead, and It’there’s always some value. It’s not about 100 or zero, it’s about where is that platform at this moment. Look at the merits; does the benefits still outweigh the costs.”
It’s not about how much you sleep, it’s what you do when you’re awake.
#53
On changing the “old minds” to accepting trying new ways:
“If you want to move mountains, you’ve got to come with thunder. Be aggressive, rogue, even a little disrespectful. But… you will need to deliver.”
#55
On marketing:
“when you do things that are smart, you get so much residual impact than just a blank ROI.”
When you do it right, right stuff happens.
On how NGO’s should act:
The same rules apply in the profit as in the non-profit world: have an absolute respect for the customer. Even as an NGO you stil need to bring a value proposition.
#56
On what personality makes a successful entrepreneur:
“It’s all about betting on your strengths.”
On the difference between Twitter and IG:
“Twitter is the downhill, the coctailparty of our society: when things happen, we go check it out on twitter.
IG probably has the biggest part of the end-attention of the customer.”
On posting the same stuff multiple times on twitter:
I think the Twitter firehose now replicates the ticker on ESPN, CNBC etc.
I change my mind consistently, and that is why I win. The game is changing — quickly and often. If you’re not adjusting… you’re gonna lose.
#57:
On strategy:
“Everything I do, and everything that you do, needs to have strategy behind it. The strategy at the time for us was to stay low and be quiet, and focus on what we were doing internally and focus on the energy that we needed to create to build an incredible business. So that’s what we did — BUT, that doesn’t mean that’s what you need to do. It all boils down to strategy and the mission at hand, so that’s what you should be focusing your energy on. The actions that you put out to the world need to replicate the mission you’ve set out to capitalize on. This isn’t a one-size-fits-all game. You need to understand what you’re looking to do and do whatever it takes to get that done. Period.”
#58:
On ‘The Middle’
“The middle is the commoditized work that everybody does. if you’re not trying to break things you’re not doing a good job.
What I mean by this is that everybody winds up doing what the market calls for. They’re focusing on what’s popular in the moment and not focusing on where the market’s going. DO THE WORK THAT NOBODY ELSE IS DOING. Don’t be afraid to break things, and hustle your face off ’til it hurts.”
#59:
On how to push your team beyond their best
“Everybody is driven by things, so first and foremost, you need to use your ears and listen. You need to sit down with your employees and understand where they want to take their careers. Once you understand then you can set them up to be in a place for them to deliver: listening + over delivering for them on what you hear creates a scenario to make them over deliver. Provide for 51% of the relationship forcing them to be good enough to deliver on the other 49%.”
#60
On social media efforts:
Lack of consistency is a huge vulnerability
On technology and its effect on traditional professions
“There’s a false sentiment in the market that technology eliminates humans. Technology sets up the humans that know how to use that technology to leverage against other humans that don’t.”
#61
On hiring and working with friends:
“If you lose a friendship from somebody because you had to fire them or they left, because it didn’t work out, then your friendship wasn’t as strong a you thought.”
On how to tackle your ‘grey-haired’ business if it seems harder than other businesses, like f.e. the funeral business:
“You should become a media company in plain sections that are related to the industry. And furthermore: understand your industry, but disrespect it and innovate!
On how to turn on your brain:
When you love what you do and when you have passion about what you do, there’s no friction whatsoever to ‘turn on your brain’.
#62
If you’re not building up your equity, you’ll always be making less dollars then you could be making.
#63
Social media is the plumbing to word of mouth in our society. Social media speeds WOM up… but you’re product needs to be good!
Do this:
Put in the work
do the right things
listen to your audience
hustle — work
try
do the right practices
do not automate
#64
If you want to be an anomaly… you’ve got to act like one.
On finding the time to focus on your own brand AFTER working on your clients projects:
“You need to work more and faster in the time you have. You might also need to prioritize what’s important and what not.”
#66
When talking about how ads are more entertaining again like in the 60`s and 70`s:
Old is New
On going on the offense:
“a lot of people are not moving their business faster because of lack of offense: offense in hustle, offense in finance, …”
On how to market a new, higher priced product to your audience:
“Maybe you shouldn’t. You may have to go out and find a new audience.”
#67
On firing people:
“The firing process is immensely important in every organization because there are a lot of angles: not just firing fast, not just not firing, it’s also how you fire, etc. You need the EQ and the people skills (or find someone who has them).”
On if brands should be on every platform:
“No, not every brand needs to be on every platform, but I also don’t think they should just be on the popular ones. Don’t be on the popular ones when: you don’t know how to communicatie or when your audience isn’t there.
Be in the right place, regardless of it’s size. Choose the best platform for your business, based on who you are trying to reach.
You have to reverse engineer the demo you are selling to or who you are aspiring to sell to. And that’s where you need to storytell around the attention graph of that person predicated on the platform that matters most.”
#68:
On optimizing hashtags on Twitter and Instagram:
“Hashtags are not own able. Everybody can jump in and use the hashtag. So… flip it. look for the hashtags that are already trending and popular on both platforms and try to reverse engineer into them so you can “ride the wave”.”
On marketing for traditional stores and retailers like bookstores etc.
“I would sell 30–50% less books (or product xyz) to clear up the square footage to really activate the physical location to find other ways and means to make dollars. f.e. make it an event space, coffee shop, coworking space, … make a secondary income of what was your first income. Go for multi-use, experiential, …”
On how to overcome your people-pleasing nature:
“Easy. You don’t. It’s not a weakness. Your weakness is you don’t know how to throw a right hook.”
I’m a big fan of becoming the honey and letting the bees come to you
#69
On different ways to monetize media sites:
“Organizing events is a big moneymaking opportunity, but also getting one ‘anchor’ brand: one keystone partner like a stadium name sponsor.
And I also see mediasites and agencies combining.”
On ‘creative’ Superbowl ads versus those more direct advertising the product/service solution. (f.e. the Nationwide superbowl ad)
“Advertising is supposed to make you remember, think and recall. I’m pro the Nationwide piece of content because it made me think about what this people are offering a hell of a lot more than where people bring back old school celebs and 10 minutes later you don’t even remember which snack, soda or beer it really was…
I’m a big fan of going countercultural in a crowded environment. There’s a lot of value in always playing the other side of the equation, and the content is at least closely tied to what Nationwide does for a living.”
#70
On why you should go work or intern pro bono when you’re looking for a job as a recently grad:
“You could spend half a day working for someone for free so you can: pick up skills, network, learn your craft, create the leverage for that employer to hire you or make them tell somebody else to hire you. Put your skills into action!”
The number one underrated brand in the world is human beings. People are good 99,9999% of the time.
On how to throw a good right hook after a lot of giving:
“You just honestly ask and go for the sale.”
On how to leverage social media when you are an up and coming actor/musician/xyz:
“You’ll have to map your target audience, look for the exact names and go after them directly, meaning: I would try to put content in front of them on Facebook, I would literally @reply to everyone of them on Twitter (=respond to what they’re talking about). Find out who you’re looking for and go directly at them by either running ads against them (Facebook Dark Posts) or look for shared connections and leverage those (ask them to RT etc). Find the way that is tactful, not too forceful.”
#71
On the language in which you should produce content if living in a non-English speaking country:
“speak in the language of the people you are trying to reach. Speak in the native tongue unless English is also the 2nd language and is covering 80–90% of the speakers and you profit form your content going outside your country’s boundaries.”
You are who you are. Most brands say “our brand represents this so this is what we have to do.” That’s not true. What you do becomes your brand.
On how to market a business in an industry that has a bad rep or when people only use it in emergencies. (f.e. like a towing company):
“Become a media company. Create a site, a place, and become a community hub of content & information and then every few posts you can talk about your business.”
at some level I think it can be slightly dangerous that we trust the people that most talk about the things we talk about. I challenge you to once a day, once a week, at least once a month to read heavily with an open mind the counterpoint to the things that you believe.
The Thank You Economy is quite easy my friends. It’s not about the tactics, but about the religion of actually doing it.
#72
On working for free:
The problem is when you are doing something for free, it needs to be strategic. By giving away something for free you create leverage to do something that is not for free.
If you understand WHY you do something, it becomes much easier to do it.
#74
On the challenge that social networks face
“My belief is that the supply and demand of noise is the real issue in social networks. Restrictions is where the action is.”
On ‘Riding The Hashtag’ on Facebook by using content that already works:
“Make sure there’s no dilution regarding your main message. Does it help you accomplish what you want?”
On getting sick:
“I think getting sick and being sick is actually psychology. The brain is the most powerful tool.
When you are sick or sleeping, rest. Your body is telling you something.”
#75
On automation in social media:
“Automation has its place. Automation is great if you’re just trying to make thinks happen, like in: getting the task done. But what about the result that you’re trying to accomplish? interaction, native conversation, etc?”
#76
On the clouds and the dirt and the balance between them:
“You need a healthy balance: stick to minimum 70–30 clouds versus dirt. If you’re DNA says: be a big thinker, go 70 there, but keep the humility and the practitioner skills to bang out the other 30.
But also do consider the occurrence of the flow: the balance mostly needs to move at certain times.”
Ideas are shit without the execution and vice versa
On how to right hook to get people to your content, when your content is the content:
“The key is to put out micro content. Traffic to your site is a byproduct. Your audience wants to go to your website, but they rather be in all those other places. It’s up to you to be there and use that as a gateway drug to get them there. At the end of the day, communicating with your audience is the number one thing that you should be doing at all times.
Whatever you think actually communicates and has an ROI versus time that you put against it, do that.”
#78
On the value of traditional advertising like bathroom advertising:
“I don’t hate all traditional media. The truth is I just care about the attention graph. Show me where the eyes and ears are, and I show you something I believe in.”
Everybody can be in everybody’s business if you have the talent.
On how to get in the know of your audience:
The very simple tactic I used to overindex on social in 2007, ’08 and ’09 is listening.
On posting videos on Youtube versus Facebook:
“Where should you post your video: on Facebook or Youtube? I say: both. Because you never know where somebody is gonna see you. One view could change your life. That one view could be Oprah…”
As a musician, if you’re not on soundcloud, not on snapchat, vine and instagram, than you don’t exist to a 25y old (and under).
You want to make enough (dollars) to really crush it and do what you love? Well then you’ll have to care about your audience. One by one by one.
#79
On the ROI of jumping in on a hashtag, conversating with non-customers:
“The value is very low, but the one upside is the homerun, the anomaly: you get somebody because they care about that trending topic and they amplify you, which then brings awareness back to you. It’s a tactic that needs strong strategy around it.”
The one thing missing from peoples repertoires in this world is the listening. One of the biggest jobs you can do at scale is go and twitter search people talking about your topics and then jumping into their conversation. You jab within the listening.
On how to handle negative reviews:
“You should jump into any Yelp-or-whatever negative review that you have to jump in and answer away any one of them immediately. Don’t fight it, fighting it is feeding the wrong energy. The optics of you jumping in, to the rest of the world, is more powerful in the amplification of who and what your intent is. And the depth of really giving a crap about that person, really matters.”
Everybody is watching when they want, how they want, outside of live tv shows which are basically live result shows, award shows and sports. (And without sports the tv industry would be in such a different place.)
#80
The truth is you can only talk about, and demand and command attention and respect around something you’ve actually accomplished.
#81
On how to choose (or follow the advice) on short versus long format web shows:
“Quality trumps everything. The length is not the variable of the quality. It is the message!”
On how to rock a stage:
“Talk about stuff you know.”
On Facebook’s video push versus youtube:
“Facebook is a massive competitor to youtube. The data that Facebook sits on top of, and that allows you to target against, creates an ultimate machine.”
Competition breeds innovation.
#82
On how to tackle rising ad prices on social platforms:
“My overall plan is to go to new platforms, be there but hold my breath for 3–7 months when it’s not as valuable, to make sure that when it does become more valuable I am there and then ride that wave for 12–24 months before those platforms become mature and add an ad-product.”
you don’t necessarily need to hire millennial to market to millennials.
On how to retain and increase followers when starting from scratch:
“Reach out, engage and bring value. You need to talk great and need to listen great.”
#83
On the value of blogging:
“People understand they need great skill to be a wonderful storyteller within social networks. You have to be good at the bar before you get a chance to do something at home.”
On what to consider when creating a long term social media strategy:
“It all comes down to reverse engineering. Everybody is different and everything is determined based on your (client’s) current long term and short term needs. But the truth is: short term and long term needs are really balanced based on a moment in time.”
‘Vaynerchuk’ is just a name. Names don’t mean crap. What you make that name mean is the real game.
#84
On jumping on US platforms that have not yet picked up in Europe:
“The upside of being an early mover in a new platform that has the potential to pop is so much greater than the downside of going to a new platform and wasting 4–5 weeks (or 10 months) and it didn’t pop.”
On how to dress customer service on an e-commerce website:
“It comes down to realizing people act surgical and are execution-oriented on your site. And you as a marketing engine need to be great at creating discovery across the whole web and then funneling it to surgical execution on your site.”
#86
On delegation:
“The number one rule to delegation is recognizing that 99,9% of things don’t mean shit. From the moment you start thinking that those things actually aren’t important, it becomes a helluva lot easier to let somebody else do it.
Ego oftentimes is the issue with delegation.”
Intent trumps everything
On the retention of people in your business:
“When you’re pure, when you want to win with, not on the back of, people start sticking around.”
#87
Leadership is knowing when to listen and knowing when to talk. Knowing when to take a step back and knowing when to jump in.
On FB videos versus youtube videos:
“The virality that Facebook allows you is greater than the virality Youtube allows you. And, you know what you’re getting from Youtube from looking back at the last decade, but by not tasting what Facebook could be bringing to you is just a mistake in overall strategy.”
#88
On when to hire someone as a freelancer or as an employee:
“When the moment you fall in love with them and want them to join your team because they bring value to your business. Or, when it’s necessity (new clients, business is growing, you’re selling more stuff). Or when the freelancer really wants to join, and you are willing to invest on short term to get the long term ROI when it starts kicking in 9 months from now.”
On why putting out jabs also matter in B2B:
“If you love something, by talking to the world even if one person is listening, all you need is that one person to share it and the pipes of social media get into motion.”
You’re always one piece of content away from having your life change.
(why I do well in business is because I realize) nothing really changes, things just evolve.
On how Meerkat/Periscope will be used:
“Everything that is live on tv, Periscope and Meerkat (and any other livestream app) have the chance to play in.”
#89
(This episode is with Jack and Susan Welch)
On failure:
“Qualifying the failure is important.
Failure also helps you realize that afterwards, the world does not end. Failure makes people better at handling tough situations.”
I don’t need peacetime generals. I need wartime generals.
On letting go the bottom 10% of your team (when striving for a top team of performers)
“Tell them what’s wrong and what they’re not doing right, and give them a chance. If they don’t make it, let them go. But when you let them go, you love ’em as much on the way out as you loved them on the way in.”
On policies and handbooks:
Forget documentation, have a culture.
#90
People will pay for anything if they perceive value.
On what questions to ask in a first meeting with new client in a client service agency.
“First: what’s your KPI: what is the one thing you want us to accomplish? Is it views? Sales? Perception? Press?
1 A: how are you judging us? And 1 B: what are the results? And second: what are you willing to tell me about your warts/issues? Are there any politics or money issues we need to know about?”
#91
On how you should incorporate extra content for your website visitor:
“Make added content and give added value, make it part of the overall experience. Make that the (or an extra) reason why they come. Add, not substract. “
On sponsorships for shows etc:
“ Try to be in the brand association pricing. I would price it as humanly high as possibly and let it land to where the market actually says.”
On how to approach pricing:
“A lot of people don’t price accordingly: they directly ask for what they want, but usually you should at least double or triple what you eventually want to get, to leave room for negotiation.”
#92
It doesn’t matter how you start, it’s how you finish.
People with big brand equity (athletes, musicians,…) should not endorse products or services, that should own them.
On what comes first: choosing your target group or business model:
my actions were setting up my counterpunch and that’s a very strong model for business.
On how to fund sponsorships on social media:
“Use Twitter search for terms around your subject, see which businesses are already engaging by putting out content or engaging with content around it, and then replying to them in a conversation. (Counterpunching!”
#93
On how to keep your company hungry:
“Everything stems from the top.”
#94
On the importance of IQ versus EQ in business:
“Both are important. But it’s about doubling down on your strengths. The key is self-awareness, so figure out which one you are: more IQ or more EQ.”
Technology will push us into a corner where the shadows of society will not exist.
#95
On Facebook dark posts:
“The way to be successful with dark posts on Facebook is to understand the psychology and salesmanship it takes to create a narrative to the end consumer that you target that predicates an action for them to purchase something that you want to happen.”
On how to tackle heavy topics in your communication (like f.e. human trafficking):
“Certain content has to be done in a certain way. The information you put out needs to be truthful, and needs to be contextual to the platform. I would use narratives that actually educate the market.”
The best way to respect content is to respect the content.
#96
Ideas are shit, execution is the game.
On the one thing to prioritize on as a one person business:
“Sales. Money is Oxygen.”
#98
The more you ponder, the more you squander.
On how to deal with pissed-off customers:
“First, get to know if they’re right. I judge how right they are. If 100% right, I’m coming in with nothing but empathy and ‘how do I fix it’. If they’re wrong, I come with offense. I tell them I get it and I’m sorry, but than I call them out and explain.”
#99
On the importance of real life meetings (in business):
“Real life meetings matter because there’s just so much context that can be done in human interaction that doesn’t happen over digital.”
#100
On automation:
“There’s a place for automation, but don’t go automating human interaction or making pretend it’s you.”
Sell to people that are willing to buy.
On presenting:
“People overthink presentations. But why I’m so confident is because I just talk about what I know. I stay in my lane. It’s hard to talk above your execution, so don’t be an expert before doing anything. Walk in with humility, talk about what you know and communicate the way you’re most comfortable communicating.”
On where the sharing economy (connecting people) will go:
Q: human inefficiency is the most interesting biggest upside market. And people will more and more pay for time.
On investing:
Bet on the jockey, not on the horse.
Technology is the gateway drug to human interaction. Use it!
Serendipity is where the magic happens. All of it.
On passion, skills and strengths:
“Passion can be a strength. But passion plus one, two or more skills is more interesting.
Skills come in two forms: you went and formed it, or it naturally comes to you. But always bet on your strengths.”
#101
… we’ll get there in a few months from now :-)
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