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14 Entrepreneur and Influencer Lessons I Learned from Crushing It by Gary Vaynerchuk: Part 2

Filed in: Entrepreneur



Hey entrepreneur; you’ve heard the saying that knowledge is power. Indeed it is! Last week you discovered my first 14 takeaways from Gary’s book and here are the next 14.


15. Work for less

As an entrepreneur sometimes you have to work for free (especially if you’re just starting out) or for less because that experience will pay off later. 

16. Outsource what you suck at

Are you really cut for this? 

Be smart. Outsource everything you can or hire people that are qualified to do the work. You can’t do it all. It’s so much more fun when you focus on what you love!

17. Analytics don’t tell the whole story

Stop chasing numbers and focus more on creating content that will bring more value to your customers.

18. Be patient

Patience is the key to success. Work harder than anyone else in your niche.

19. You’re only crushing it if you’re living entirely on your own terms

8 entrepreneur essentials for crushing it:

  • Intent
  • Authenticity
  • Passion
  • Patience
  • Speed
  • Work ethic
  • Ability to track consumer attention
  • Master social platforms and content

20. Eat shit

Gary says “eat shit for as long as you have to”. Okay Gary I already have. ☹

Eating shits mean you have to be the bigger person, that the customer is always right, put your employees ahead of you, don’t take many holidays, be methodical, pay off your debts, and on and on. Put yourself last.  From Gary’s perspective that is the entrepreneur way.

My exception to this is around my health and my loving relationships.  No matter what I’ll always make those a priority. I guess that means longer hours.  And when you have reached your brand and business goals, then you can start living it up again but of course not putting yourself back into debt again. It always feels good to save more than spend more doesn’t it?

Gary reminds us that smart entrepreneurs don’t care what other people think.

21. Stop agonizing over your decisions

Don’t be afraid to make mistakes. Gary thinks you are better off being wrong 10xs and being right 3xs instead of trying to only be right 3xs – like trying to and always get it right. 

Seriously. What’s the worst that can happen? Go for it. The market will dictate if you’ve got it or not.

I would not engage in a crazy financial investment that if it backfired would bankrupt me for life but calculated everyday business decisions… for sure.  Do the homework, use common sense, and pull the trigger.

22. Work hard

When you first start out, there is less time for leisure. That is if you truly want to crush it as an entrepreneur.  Gary recommends that you talk to your family, get on the same page, set a plan and a timeline and go for it. You can always adjust along the way.

I came across a recent article in Inc. magazine and Storenvy founder Jon Crawford on Founder Dating quoted “Work, sleep, family, fitness, or friends–pick three. It’s true. In order to kick ass and do big things, I think you have to be imbalanced. I’m sure there are exceptions, but every person I’ve seen riding on a rocket ship was imbalanced while that rocket ship was being built. You have to decide if you want it”.

I’ve  always been a hard worker, maybe a little too much at times. I’ve always been a go-getter. Always moving forward and always growing. I firmly believe you have to make your health a priority. Health is wealth. How can you expect to accomplish anything or spend time with your family if you are sick, or tired, or moody, etc. I certainly monitor how much I work. If I find myself getting cantankerous, I stop and breathe. My husband doesn’t deserve it:)

23. Time management

Decide on how you’re going to spend your time. Prioritize.

What I do every month is block off the hours where I must fulfill my obligations. For me that means my fitness workouts, babysitting with nieces, Sunday evening with the family, then work. 

24. Stop sitting on your butt

Nothing is going to happen for you as an entrepreneur if you sit on your butt and wait for things to come to you. If you want to reach your goals faster Gary recommends: Meet with 2-3 people per day who can get you awareness, distribution, or a sale.

If you’re not willing to do the grind stop bitching when your business doesn’t grow as fast as you want it to be. 

Because the truth is you can’t do it. Be practical with your choices. 

25. Leveraging socials

Gary recommends that you don’t get too comfortable with one social network and that you make the time to develop the skills and know how on the others work too. 

26. Credibility

Anyone can brand themselves all they want but if you don’t have credibility or have not done anything, it’s almost worthless. You can only sell something that’s actually good. 

This is why I studied and blogged about Pinterest marketing for business my first year. My dream was for Pinterest to reach out to me one day in whatever capacity. In my second year running my Pinterest management business Pinterest contacted me and invited me to be one of the experts in their Elite Business program. 

Getting acknowledged by Pinterest was the credibility I needed. 

I loved how Gary says that “you don’t get to call yourself an expert until you’ve put in the work. Basically the market decides, not you.

There are many of people out there who call themselves experts but actually can’t prove that they are. It’s actually not that difficult to see if they are experts or not. Heck, just Google their name and see what comes up. Are people talking about you? Does your name keep coming up when it is tied to a specific topic? Heck if you go on Google and searched for “Pinterest Expert Anna Bennett” you’re going to see a lot of my Pinterest interviews, articles, blogs, webinars , podcasts, etc. That’s credibility.

27. Take risks

According to Gary V learn from your mistakes, change it up, and try again. Put up your stuff and wait for the market to judge you. If no one likes it, take it down.  Put out something else.

But here’s the thing. Your natural gifts will only take you so far. Gary says if you want to be your best, you’ll have to work at it but avoid being a perfectionist.

28. Get discovered

Collaboration is one of the best ways to grow a fan base quickly BUT it could take you years, not months. If you don’t like the sound of that Gary says, close the book. ☺


If you read Gary’s book I’m sure your list of tips for being a successful entrepreneur will be longer than mine, there’s a ton of good stuff there. But like he said his book isn’t a step by step formula. He shares success stories about influencers that have been successful by leveraging social media. But it’s up to you to figure this stuff out. You can’t do this alone so you will need help. 

He doesn’t water down the fact that you have to have an amazing talent. But if have talent in addition to being funny, creative, or smart you will win. It may take you longer than you thought but it will happen. 

He also doesn’t shy away from saying that “success takes a shitload of work”. He says that multiple times. Because when I hear things like “put your business on auto-pilot” I’m thinking “yeah right”. There’s no short cut to success. You gotta work it. 

If you thought Gary was going to show you how to do something the easy way, well sorry, he’s not saying it’s easy. He will remind you that being an entrepreneur and an influencer is a different life compared to your day job but it’s certainly NOT an easier life. The good news is that you will have more flexibility and fun once you accomplish your goal.

So now, you get decide. 




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