Entrepreneurs
After Spending A Day With Gary Vaynerchuk, Here Are The Brutal, Harsh & Required Lessons You Can Learn.

Gary Vaynerchuk was in Melbourne recently and I spent the day listening to his advice. A lot of what he said was like a slap in the face combined with a bucket of cold water thrown on my head every ten minutes or so. He speaks the truth and he does not hold back.
He’s gone from just being a social media guy to someone who aims to inspire – sort of how Tony Robbins and many others that created the self-development movement did in their day.
Here’s what Gary taught me that will be instantly actionable for you:
Never forget the underdogs and the people who are struggling.
At these type of events where Gary was speaking, there is a class system (love it or hate it). The people that spent the most money sit at the front in the VIP section, and as you go further back in the room, the seats get cheaper and often the wealth of each individual decreases.
When question time came, lots of people put their hand up and Gary went straight to the back of the room. He did it to prove a point. The people in the front could see him after the event and they generally had already made it.
Gary’s interested in the underdogs and the up and comers. This is because he knows that they’re the people that have the most potential and he knows what it’s like to be one of them.
What this simple lessons taught me is that you should never forget the people who are or used to be just like you. How much money someone has should never be a measure of where you focus your time. If you really want to make a difference, then serve everybody.
7 pm – 2 am is where your dream begins.
Many people say they don’t have enough time to follow their dreams. Gary is a practitioner who is busting through people’s BS excuses and he hates people that complain. So when someone asked the question “How do I find time to work on my business in between work and family?” Gary responded with 7 pm till 2 am.
That’s the time when your dreams are executed on.
“When you come home from the office, it’s time to get to work and not drown yourself in booze and Netflix”
We all have the time; it just comes down to whether we’ll use it or make excuses for why we can’t do stuff.
For me, my time is a bit different. I practice what Gary preaches except I do it from 4 am to 7 am and from 7 pm until 10:30 pm. Do what works for you. Bottom-line, you have to work.
Control your expenses man!
One young man got up during Q&A and told Gary he doesn’t have enough money to start a business. Gary’s face lit up and he was ready to pounce on the poor man.
“Do you have a wife and kids?”
“Yes sir I have a wife and no kids.”
“Where do you live?”
“In a four-bedroom house close to the city.”
Gary exploded and screamed that he needs to control his expenses. Many of the so-called entrepreneurs out there make up excuses about money. When you drill down, we all have enough resources to work on our side-hustle or our dream.
The problem is that we buy useless stuff we don’t need. It comes down to priorities. If your dream matters, then as Gary says, sell your four-bedroom mansion and eat dirt for a few years by living in a one-bedroom apartment.
You don’t want to learn the new stuff.
Many of you got somewhere with email and landing pages and made a bit of money. Now you don’t want to learn the new channels like Alexa and Virtual Reality. What you did until now will not take you where you want to go into the future.
When you’ve got something, you tend not to put in the work to keep it. If you’ve got nothing, the time is now for you. Having nothing is in many ways your greatest asset. Having nothing gives you a sense of hunger that money can’t buy. That’s why many of you who are living this life of entitlement are drowning in your failures.
The world owes you nothing. Go out there and be phenomenal.
Embrace your vulnerability and have the courage to take massive action.
“Not wanting to learn the new stuff is making you ignorant of the success you could be happening”
Lives built on one pillar.
Gary spoke a lot in Melbourne about people he’s met who have their entire lives based around one pillar of success. So many people have built their lives on one knockout punch, one arbitrage, one hack, one freebie they give away.
You can’t have sustained success if you keep doing the same thing over and over. The market changes. People change. Even you change.
You need multiple pillars to your success and that will change over time. Stop complaining and become a lifelong learner. You don’t have all the answers and the game is constantly changing. Either grow and learn or die in your own success. This is brutal but true.
Give away your best information for free.
It’s counter-intuitive but it works. I’m living proof of it. My best work is all free and that’s how I reach millions of people per month. I can also make money as well and that works even though all my content is free. It works because people have to know you first before they’ll trust you with their time.
Respect people who comment.
There’s a lot of you who have online communities who take them for granted and don’t respect the people that give you their attention and their time.
Gary religiously looks at people who have a reasonable size audience and he notice’s one thing: many of you never respond to the comments you get on social media.
Obviously, you can’t respond to everyone but if you never reply to people, you’re disrespecting everyone. Learn to respect people and inspire them, and then you can be a leader in whatever field you’re in. Ignoring everybody is not good for you. Chances are your ego might be too big.
There’s a lot of fakepreneurs.
Gary talks a lot about entrepreneurship being the flavor of the month and he’s right. There are a lot of fakepreneurs who don’t respect the game and try to take the easy road. The beautiful thing about capitalism is that when we have a market correction (Global Financial Crisis), all the fakepreneurs who are doing it because it’s cool will go back and get a job again.
You can’t fake it. You’re either an entrepreneur or you’re not. It’s okay if you’re not. Stop pretending and get to know yourself better.
Just because you haven’t figured it out yet doesn’t mean it’s not happening.
“The ROI of a basketball is zero. For Lebron James, the ROI is worth billions of dollars” – Gary Vaynerchuk
If you haven’t found the answers yet, then that doesn’t mean something doesn’t work. Just because you don’t have the answer to a problem, it doesn’t mean you’re right. Trying to be right all the time is a disease that will infect every aspect of your life and screw you like the casino.
There are people succeeding somewhere in the world at whatever you’re tyring to do. Rather than complaining, go find these people and then offer them mutual value in return for their strategies.
Only do what you are good at.
Facebook Live is useless if you are boring or don’t know what you are talking about. The social media platform is irrelevant. You actually have to know your stuff for anyone to join your tribe. Double down on your strengths and the ROI of your time will increase.
We will always choose time.
You will pay money and give up your privacy for time. Uber sells time, not transport. It’s quicker to delete than it is to unsubscribe from an email list. Audio is the next big thing, says Gary, because it sells us back time.
If you are an entrepreneur looking for a channel to grow an audience from, start a podcast or any content that is centred around audio. The most basic podcast you can do is interview someone who has an audience, and then syphon their brand so you can get access to their audience.
Focus on creating.
The world is changing and if you’re not talking to us all via either video, text or audio, then you’ll become irrelevant very soon.
Start sharing your ideas.
Create content.
Create value for as many people as you can.
What happens after you get phenomenal, great advice like this?
You’ll be pumped for a few days. You might attend an event like this yourself. Then next Thursday comes and you face a massive life challenge and go back on the defense rather than living your life on the offense.
Don’t just get pumped up for a day. Keep the momentum going. Listen to podcasts from people like Gary and Tim Ferriss. Read non-fiction biographies of the greats. And most of all, keep taking action towards your goals. That’s how the pumped up feeling will last.
Thanks Gary Vaynerchuk for coming to Melbourne and inspiring us all. Much love and much respect.
If you want to increase your productivity and learn some more valuable life hacks, then join my private mailing list on timdenning.net
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While there are, of course, cases where management could do better, this isn’t just a “bad boss” problem. The relationship between leaders and employees is complex. Instead of assigning blame, we should explore practical solutions to build stronger, healthier workplaces where everyone thrives.
Why This Gap Exists
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1. Practice Mutual Empathy
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2. Maintain Professional Boundaries
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5. Empower Employees to Grow
Empowerment means giving employees responsibility that matches their capacity, and then trusting them to deliver. Encourage them to take calculated risks, learn from mistakes, and problem-solve independently. If something goes wrong, turn it into a learning opportunity, not a reprimand.
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10. Recognize Efforts Promptly
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Design compelling career paths
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Simplify HR processes
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Redefine the value HR brings
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Organizational success starts with people, always. Build the relationship with your team first, and the results will follow.
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