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My goal to become an entrepreneur recently led me to an opportunity to interview Gary Vaynerchuck. 

Gary is an entrepreneur-immigrant from Belarus who has gone from his hugely successful e-commerce business to his own YouTube show, to now focusing his multi-million dollar company, Vaynermedia, on becoming the foremost authority on using social media to build brands.

Below is the core of our dialogue (abridged, full audio at the bottom of the page), which changed my life and gave me the last push I needed to take the plunge in starting my own business. I am totally doing this.

Kendel: One theme that you have built upon in your business is caring. You are the guy that cares the most. What are three, specific under-utilized ways to show caring and build goodwill?

Gary: It all comes down to effort. Three ways are:

     1. Answer in a personal way, personally.  In 2010, I personally answered every single email and tweet that I got.

     2. Storytell about others, not just yourself. I am a LinkedIn influencer, and some of my favorite articles were highlighting people that were underrated, people that more people should know about. Giving people opportunities to be discovered through you is a great way to show that you care.

     3. Make yourself accessible.

Kendel: I love how you are goodwill-building minded. What are some questions you ask yourself to maintain this focus on goodwill-building. How do you keep this heightened awareness about this part of your business?

Gary: Mainly because the only question I ever ask myself with regards to my business is “What is my legacy going to be?” I’m not worried about short-term financial gains. I am dramatically more concerned about that. There will be people who make more money, build businesses quicker, more exposure and air time. But I am going to have a tough time being beat as being known as the entrepreneur who cared the most.  That is where I want to be. My ultimate goal is to get every person I have ever met to show up at my funeral.

Kendel: So like you were saying earlier in your career—“legacy is greater than currency”.

Gary: Well, if I do aspire to that and make that my biggest goal, a funny thing happens along the way—I gain financial success as well because the principle tends to drive the result.

Kendel: We’re in an age where you’ve said there is never a better time to cash in on your passions. What are some things that keep people from discovering their passions and really breaking out and pursuing it? 

Gary: Number one is not realizing how possible it is. I think that is why my book, Crush It!, is such a big book. It opened people’s eyes to the notion that this is possible. Number two comes down to practicality. If there is no income coming in, how are you going to pay your bills and live your life? That makes a ton of sense. That’s why I push the 7 to 2am mantra. There are risks. You might choose the wrong thing. You have to find the crossroads of passion and expertise. And then you have to put in a ridiculous amount of work, right? We’re talking every day. Most people are simply unable to get to that level.

Kendel: That’s where I’m at. I feel like I am an outlier, very passionate, but I am not ready to break out and go at this whole entrepreneurship thing.    

Gary: Try things. Try a different blog topic, it might go more viral than what you’ve tried before. But just trying—test and learn. That is why I wrote my latest book, Jab Jab Jab, Right Hook. It is kinda a followup to Crush It!  It is a manual, tactically organized, telling people what to do to break through the noise.  And as I have been doing these interviews and meeting people, I get this either “Hey, you changed my life” or “Hey, I believe you, you’re right, I just haven’t been able to break through.” That second response motivated me to write the book—answer the question “How do you use free tools like SnapChat, Instagram, Twitter, and Facebook to achieve success?”

Kendel: What are some top mistakes that people who think they have passion enough to start a business make?

Gary: They do something around what they want to happen, but don’t really have expertise in it. For example, be a business coach, but never really sold anything. Number two, they don’t actually realize how hard it is. It sounds so good on paper, but you have to do it every day. They think 3 or 5 days a week can pull it off. So, the lack of awareness of what it really takes. Third, they don’t educate themselves up front to get the knowledge they need.

Kendel:  I have several interests that I want to pursue and I have done things in relationship counseling and niche consulting, but I have no idea how to monetize passions like that. How do I go about starting?

Gary: That’s why I wrote Jab Jab Jab, Right Hook. It sounds to me like you’re a jabber. You know how to jab which means you know how to give. Jab Jab Jab, Right Hook stands for “Give give, give, ask.”  But if you can’t land a knockout punch, you’re not going to be successful. It sounds to me like you are doing the right things, you just need to figure out what you want to do to monetize that whole scenario and number 2, you need to figure out how to ask for it.

Kendel: I have a hard time asking for things. It feels awkward.

Gary: You have to understand you’re not asking for favors, what you’re doing is asking for reciprocity. You’ve brought value. It’s like what we’re doing right now. I’m helping you build up your blog. My hope is that you will go out and buy 5 copies of my book instead of one because of the value you have received. You just have to know what to ask for (once that is in place) and #2, you can’t be scared to ask it. If you are scared, start with email. It is a little safer and easier.

Kendel: I don’t have one in place, what am I looking for?

Gary: Maybe you can consult on how to throw jabs. That is how you have gotten attention in the first place. Maybe you start approaching people that are doing a lot of this (usually about selling). Teach them the soft skills you use to get attention for what they are trying to do. Or, maybe you can write an e-book for $20 that talks about all your tactics. Then once you help someone out, forward them a link to buy your book and say, “Listen, I’d really appreciate you supporting my book.” These are the things we are talking about.

Kendel: Is Amazon the place to publish?

Gary: I think Amazon is a great place to go. But you’ve gotta set up something monetizable, otherwise, what are we talking about here? We’re talking about businesses.

Kendel: I really do feel poised to do this. I did two years of Teach for America where I worked until 2am in the morning every night for the cause. I know what it is like to dedicate myself to a cause, I just don’t know how to do that for myself.

Gary: It is a very common thing. If you don’t take a real good, hard try at it, you’re going to end up being 75, 80 years old and never getting to it.  You’re gonna hafta give it that “at bat”, you just have to. I’ll tell you this, I feel we have a kinship, we’re very similar. But I will tell you this: there is one thing that makes me different. And that is the selling part. And the best way for you to feel good about it is to feel good about what you’re selling. I’ve never sold anything I wasn’t proud of. That is what you have to strive for. If you write your e-book, or come up with a course, or if you sell underwear or whatever it is that you do, make sure you price it in a way that you are proud of it, and then you are on your way. Maybe you finish the e-book and you think it is worth $9. So sell it for $8. You’ll feel great. Get it?

Kendel: Right. Interesting. Got it. What is one thing you tell yourself when you’re really not feeling it, how do you get into gear?

Gary: I remind myself that I’m going to die soon. And if I don’t do it now… I keep things very big picture. This is about life and death. This is about legacy. I make my decisions based on this. I am very self-aware about the fact that regret is a terrible thing to have, and I hound against that notion… go speak to a 90 year old person, they’re never regretting what they did. They’re regretting what they didn’t do. Always. Every time.

Kendel: One of the things I run into is a mindset that doesn’t look at broad possibilities. How do you tactfully invite people to think outside their current world of what they think is possible?

Gary: Storytell with empathy. I’m a straight-shooter, and often it is the only way to break through. People are dramatically cynical by nature. Be noble.

Kendel: Well Gary, I just want to let you know that I have made a decision in this conversation to start writing my e-book in the month of November.

Gary: I’m excited. I want you to email me on Feb. 1 because I expect you to not only start in November but to be done by then and even started marketing. So I expect a full email on Feb. 1st. I’d love to know an update. Thanks my friend and have a great day. Take care.

Kendel: Thanks again.


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