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15 Raw Entrepreneurial Lessons from Gary Vaynerchuk

15 Raw Entrepreneurial Lessons from Gary Vaynerchuk Blog Feature

Tom DiScipio

VP of Product, Speaker, 8+ Years Sales & Client Success Expertise

April 1st, 2016 min read

garyveeI’ll never forget the first time I witnessed a Gary Vaynerchuk keynote. It was at HubSpot’s 2012 INBOUND conference.

Here was a guy I had never heard of, dressed like a skater, swearing like a sailor in front of about 8,000 people at 8am in the morning, and professing some of the most prolific, mind-bending stuff I’ve heard since assimilating into the marketing world.

After an hour of absorbing Gary’s words like they flowed from an uncensored firehose, I not only felt like I just looked into the future of marketing and entrepreneurialism, but also like I could conquer anything. His energy was game-changing… and contagious.

Flash forward to 2015 and Gary is asked to speak during a USC Entrepreneurship class where he again drops some epic knowledge about being a modern entrepreneur and what one should do if they’ve been blessed with that unrelenting spirit to “sell shit.”

Although this video is just over a year old, the lessons learned are no less inspiring than they are timeless.

Below are the 15 raw entrepreneurial lessons I took away from this keynote.

1. “You cannot teach entrepreneurship.”

The word "entrepreneur" no longer carries the negative connotation of just D & F students who couldn’t hack it in school. Rather, they're not seen as the ones with the million dollar ideas instead of algebraic formulas and social studies filling their brains. Entrepreneurship is a gift, a drive, a realization, a mindset, a way of life and not everyone has it.

2. Ultra competitiveness breeds and delivers value.

Be so unnervingly competitive that it sickens you to think that there’s anyone else that can deliver more value than you. Believe to your core that you’re occupying the same space as others who are merely 2s, 3s, and 4s. “The difference between a 1 and a 2, 3, and 4 is having a stomach.”

3. “Bet on your strengths…Don’t give a f*** about what you suck at.”

Society has sold us how to fix what’s wrong with us. Trying to check-off the boxes of things you’re not good at is a complete and utter waste of time. Instead, be self-aware, audit yourself, find out what it is that you are truly good at, and go all-in on those strengths. “If you want to be an anomaly, you have to act like one.”

4. “When you have a start-up or a business, you’re playing to the market.”

Because the market is an omnipresent, unwavering, selfish beast, you must have the ability to adjust and change immediately. Don’t be afraid to change your mind… every, single day. “Be comfortable in massive chaos.”

5. “Stick to your DNA.”

It’s great to admire other successful people, but it’s more important to recognize your own strengths and surround yourself with those that bring the opposite and complimenting values to yourself.

6. “It’s never been a better time to be an entrepreneur”

“Right this second is the greatest.” The cost to spin-up a business is easy. The internet is hitting maturity and is at scale, and at the same time, there are investors that are itching to spend their money on your next clever idea.

7. “The number 1 asset to everyone in the world is time”

If you’re thinking about kick-starting your own business, figure out a way to sell people back their time. It’s what Uber really did. They don’t sell a driving service, they sell you your time back.

8. Share ALL of your content and ideas

“The value of your thoughts can be extreme.” If you can share forward-thinking, thought-leading material, you could be 3 minutes away from changing the industry. Below is the reason why...

9. “Ideas are shit, execution is the game.”

‘Nuff said.

10. “A checkbox in the loss column can eliminate you from the next go-round”

An initial failure, although a learning experience, can create a ripple as you attempt to rebuild. Be smart about your decisions, manage your audacity in the marketplace, and adopt the mentality of a marathon runner versus a sprinter. “Give a shit about 10 to 14 years out.”

11. “There’s no excuse to not start RIGHT NOW”

The market can change within the next second, and your opportunity could be lost. If you’re truly following your entrepreneurial spirits and believe your idea can win, stop giving yourself excuses NOT to do something with it.

12. Use your EQ (Emotional Quotient)

Spend a majority of your time watching the behavior of your customers and the market. Reverse engineer their thought process to anticipate their needs or what the next big thing will be. EQ versus IQ.

13. “Regretting feels like the opposite of entrepreneurship”

If you’re busy regretting, you’re busy looking backwards. Your advantage comes by simply extracting data from your past wins and losses, continuing to keep your eyes pointed forward and using speed as the variable to execute and overtake.

That’s the same advantage people like Mark Zuckerberg and Uber's Travis Kalanick used to become the entrepreneurs they are today.

14. Have a vision for the ‘gateway drug’”

You should always have a pulse on what is truly feeding the beast (the market). When a certain product, software, or service has reached massive volume, at scale, anticipate the next disruption.

15. “All that matters is the Attention Graph.”

You HAVE to find out where the eyes and ears of your audience really are. If you’re marketing to young women between the ages of 16 and 21, you better be exploiting SnapChat. “100s of millions of users f***ing matter.”

And how about just one more for good luck?

“Invest 80% into the Jockey, and ‘believe enough’ in the horse”

Don’t be romanced by an “idea.” Make your decisions and trust that the person executing has the hustle to get shit done.


Here’s a secret: Video should be your best revenue driver. And it’s actually easier than you think.

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