Jab Till It Hurts - Chapter 4: Mentorship


I’ve already talked a lot about what a big difference Gary Vaynerchuk has made in my life and my business, but I wanted to devote a whole chapter to mentorship because it’s just that important.

I first met Gary in New York City in 2014 at Lincoln Center. He was speaking at a one-day event with Dave Ramsey and Seth Godin. I’m not sure Gary remembers meeting me that day, but I totally remember the awkwardness of Dave Ramsey hosting Gary Vaynerchuk. Here’s an uber- conservative Christian who, I don’t think, has ever had a swear word pass his lips, with a guy who uses F-bombs like breath mints. I was impressed that Dave Ramsey, and his team, recognized that Gary was something special despite the style differences.

My understanding of Gary goes way back, and I have respected his honesty, his rawness, and the one-to-one relationship he has built with the people viewing his content since 2009. His YouTube presence was super small at that time; Twitter was his big thing back then. Instagram hadn’t yet come to life, and Facebook was really young. I was following Gary way before he had millions of followers.

Anyway, I met Gary at that event in New York, and I also met Seth Godin there. Seth and I had a really interesting conversation on the steps of the stage at Lincoln Center. He said something to me that I’ll never forget: “Spanky, what is it that you’re great at?”

I looked at him and said, “Storytelling.”

He said, “Then, do that. Stay in your lane and put the gas pedal down.”

That was the advice he gave me. Now, I wasn’t looking for sage advice, but that’s where the conversation went. It wasn’t until 2017 that I truly executed on his advice because of Gary’s knowledge and content.

Lead with Gratitude

I am one of the thousands of people who show gratitude to Gary in so many ways for all the great value and advice he delivers, for free, to the world. I didn’t go to Gary and say, “I have this startup, do you want to invest?” I didn’t approach Gary to offer a stake of ownership, I basically just said, “Hey, thank you. I started this little thing by accident, it’s growing, and it’s because I follow the stuff you preach every day.”

It was out of gratitude and thanks and humility that I reached out to him, and he responded. I think he naturally appreciates gratitude. When you don’t come to him with an agenda, when you come to him with true gratitude, he responds well to that. That’s why I’m able to write emails to Gary and get answers from him, and that’s why I have Gary as a mentor.

The takeaway here is if there’s someone you’ve been following and admiring for years, if there’s someone giving you a lot of value, don’t reach out with an ask. Just say thanks. You never know what might grow out of that kind of genuine gratitude. If you’re feeling it anyway, why not express it to the person? We’re all human.

Networking Like A Champ

Lots of people attend conferences, and there’s a good reason. I don’t attend conferences to go see the speaker and to sit in the breakout sessions at all. In fact, if you’re going to conferences for that, you’re going for the wrong reason. What you should be going to conferences for is to connect, and to rub shoulders with the people you need to connect with.

As you start down the path of building your business, there are going to be, inevitably, opportunities to attend conferences around your passion, your industry, your business. Find those conferences, and spend the money to attend them.

By attending these conferences, you will have access to everyone that’s in attendance. Go to the cocktail hours. Attend the brunches. During the breaks, figure out where the traffic is. Spend time being visible. Make sure you connect with the people you want to connect with. Don’t be the eye- darting leech that scans the room for your next victim. No, spend time with the people you want to talk to. Engage with them. Get their information, write their names down. Put them in your contacts on your phone. Start a dialogue with people, because at the end of the day every relationship you build is driving your network growth exponentially. Because that one point of connection could connect you to ten others—ten people who have high value for what you are doing. You just haven’t met them yet.

Use conferences like a tool. Be social. Connect, connect, connect. If you’re going to be a wallflower and hang out in the back, and watch people talk, you’re going for the wrong reason. If you’re going on the arm of someone, and think that just by being next to them you’re suddenly going to be noticed, wrong take. Get out there. Say hi to people. Shake hands, kiss babies like a politician. But mean it. Be genuinely happy to meet people, and excited. These are people who could potentially change the future of your business. You just don’t know it yet.

The Middle Seat Always Sucks...Or Does It?

I saw her coming down the aisle of the Southwest flight from Chicago to New York. I realized very quickly that her options were limited to sitting between me and the dude on the aisle, or a couple of rows back next to the bathroom. She wound up taking the seat next to me, and I could tell by her face that she didn’t want to be in the middle between two dudes and have to sit on this flight all the way to New York City, but she sat there. It was the best decision she made that day.

Sammy from Chicago is a stylist, a hair stylist. This adorable, young, vivacious woman started chatting with me when I looked at her and said, “Yeah, I hate the middle seats, too.” That broke the ice. She and I started talking and I asked what she did. She looked super trendy, she looked super fresh, she had style—even though I have none, I can tell when someone has style. She told me she was a hair stylist and then started talking about her passion and how she wanted to teach moms and dads of biracial children how to take care of their daughters’ hair. She also wanted to teach dads in general how to take care of their daughters’ hair— because most dads don’t have a clue as to what to do with girls’ hair. I’m raising my hand right now because I’m one of them, I’m that guy.

So, I asked her what her plan was to teach, and she really didn’t have a plan, she just knew that she wanted to do something in that space. The rest of the flight, that’s all we talked about. I started road- mapping a plan for her.

The plan we designed in the air that day included holding a free workshop on the Gold Coast of Chicago and advertising it to dads: “We’re going to show you how to do your daughters’ hair. It’s a daddy and daughter workshop!” A one-day event, and it’s free. She could use the salon space she works in or get a salon space somewhere else.

I told her that she could register hundreds of people for this free event, and what you can do is, if they all go away with a hair kit, charge for the kit. That way, everybody has all the supplies they need. It’s really, really simple, but what it’s doing is it’s created an incredibly high-level awareness for her brand as a stylist and giving her a ton of street cred at the same time.

That was Part 1 of her plan. Part 2 is she wanted to connect with parents who’ve either adopted or, because of interracial marriage have a daughter who is biracial, and may not know how to do their daughter’s hair. I said, “Why reinvent the wheel? Just do a separate event for these parents with a similar setup.” So, you’ve got two events coming up, both free, and they both achieve the same purpose of building your brand.

Now, the thing Sammy has going for her that a lot of other people don’t is that she’s gorgeous, she’s super outgoing, she’s bubbly. She has a personality. You put that on a camera and people are going to watch. First, because she’s attractive, second, because she’s giving value to the world in terms of hair styling. She has a very, very specific mission and purpose.

Fast forward: On a recent follow-up call she shared some great news. Sammy found another stylist who is going to work with her as a partner because this event is going to go way bigger than she had ever thought. She is putting together the first event of its kind for this particular niche. This is not to drive sales. This is simply to drive awareness and to add value to the community. Period. That’s how you build a brand.

Key Points from Chapter 4

  • Express gratitude to the people who have helped and inspire you. Don’t ask a potential mentor for help or investment. Just say thanks.

  • Spend the money to attend conferences in your industry, and go with the express purpose of connecting with other people.

  • Take a cue from Seth Godin and ask yourself, “What am I great at?”

  • Be open to giving and receiving mentorship anywhere—even in the middle seat.

  • Get specific about your mission and purpose, then figure out how to give value to people, whether it’s online or in your local community.


Did You Get Value From This?

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