Don't read this book - Ingest it into your ethos.
As a lot of creatives do, we long for the structure and stability of some of our corporate counterparts with their steady paychecks, clear path to success, and mentors to help usher them along the ladder. Thankfully, with the age of social media we live in now we’re able to follow and subscribe to any influential person we find inspiring, entertaining, and motivating.
This book, #AskGaryVee, made me do a lot of thinking about everything that I’ve experienced in my life up until this point - and in reality, it should for you too or else you’re not doing what you should: shutting up & listening. For a lot of people, that person is the ever brash and bold, Gary Vaynerchuk also known as Gary Vee. For some, they recognize the name but don’t quite know the person, so I’ll tell you a bit about why you should.
Why you should know gary vaynerchuk
It’s been said a lot, with the age of online coaches, life coaches, booming sexiness of entrepreneurship from the media and society, it’s tough to know who to trust when you’re looking for someone to follow. Yet one of the most simple age old tenants still holds true - listen to people who have actually built shit. One of the most interesting passages in the book was where Gary mentions that he didn’t even start working on his personal brand until he was almost 10 years into his career; he knew he had to prove himself and just do the work before ever opening his mouth for people to listen.
The early part of his career is one the is synonymous to a lot of immigrants who came to this country. Coming from Belarus as a small child, his parents worked hard to make a life for their family in this new country, while instilling their old-school work ethic on their children. Five years for the Vaynerchuk family seems to be a magic number, as his father came to the US with no job, got work as a stock boy in a liquor store, saved all his money for 5 years then bought his own liquor store. For Gary, early lessons in the heartache of entrepreneurship lead to him borrowing $1,000 from his father to buy baseball cards for his baseball card business, which was lost in record time. Yet, knowing it was a friendly gift from a parent, Gary then hustled his ass off to pay his father back plus interest. Which he did in typical Vee hustle fashion; joking that "selling $2000-$3000 a weekend when I was 13-14 in the malls of New Jersey. I don't know about you guys, but when you have $30,000 in cash under your bed and you're 14, and you're not selling weed, you're doing a good job." As hilarious as it is, it’s true - Gary knew how to sell and run a business which combined with an eastern European work ethic was a winning combo. Then the time came for Gary to join the family business.
This meant working for his father at his own liquor store at 14 years old for $2 an hour; a far cry from his baseball card selling days. While Gary hated it, he took interest reading everything he could get his hands on to learn about wine, especially since he couldn’t drink yet. But, the real epiphany came at 16, when Vaynerchuk realized that people collected wine like he did baseball cards. The rest, as they say, is history. After taking over the day-to-day operations at 22 years old, he launched Winelibrary.com in ’96, used email marketing + online advertising and Wine Library TV on YouTube to build the $3 million dollar business to a $60 million dollar business in just five years. Remember that magical Vaynerchuk number?
Fast-forward to starting VaynerMedia with his brother AJ, which has grown in similar fashion to over 500 employees & a list of blue chip companies anyone would love to have in just a short few years - you guessed it - about five of them. The point is, as much as Vaynerchuk can attest to having oracle like predictions and be a very entertaining speaker (which if you’re in the Maryland area April 19th, come see him speak at University of MD), at the core of it he’s got the business chops.
What chapters made me rethink my life
While I’m usually all for never shutting up, I want to make this section the quick & dirty on what chapters spoke to me. Rather than make you scroll for the next 20 minutes reading, I’ll keep it short and encourage you to find your own favorite chapters & let me know which they are.
Chapter 1: Clouds & Dirt
From the very first page, I was hit with the truth many of us know but very few remember when you’re plugging along in the day-to-day, frustrated that your efforts are not bearing the fruit you want just yet. Like I’ve mentioned earlier, one thing that Gary has is the grit to do something every single day for years before anyone pays attention - I don’t know many people who can attest to having that kind of determination, patience, and big-picture ethos that is required.
Can you really say that you put your head down, do the work, and remember to look up and make sure you’re still aligned with your big picture?
Chapter 4: Family Business
This chapter immediately stood out to me for a few reasons: Jessica being my rock, how becoming a parent of young kids recently changed my life, and my own family dynamics.
When asked how important is it that your significant other share your entrepreneurial vision, Gary’s response echoed my own feelings. For a lot of people, they see relationships or lack there of in the business world in two ways: they either distract you or empower you. I know for myself being a single person for many years who just dated, I mostly focused on my photography work and let the other stuff fall in place. Yet, later in my late 20’s-early 30’s after meeting Jessica & co-parenting two kids, if I’m being honest with myself, there were times I missed being single to feel no guilt about grinding so hard and being able to do whatever it took to succeed; sublet an apartment, move on a whim for a new job, road-trip around the country, and moving back in with my parents for a spell to save up money. Don’t judge, you’ve felt it too - don’t lie. However, his follow-up response is what resonated with me as I have accepted this idea myself.
“I don’t mean to say that I wouldn’t have been successful without her. Without a doubt I would have. But I’m sure I would have been an unhappier person, less healthy, and less fulfilled.” That last word summed it up for me - less fulfilled. If I was honest with myself, the times I was ‘grinding everyday’, what I really was doing was throwing myself into my work to distract myself from the unhappiness I was feeling - the unhappiness with my stalled out career (more on that later), my lack of long-term relationships, my ‘outsider’ feelings regarding friendships I had, and not measuring up to my own high standards. But that all changed when I met Jessica and really let myself be present - seeing that what I gave up in terms of my ability to live like I’m on the run from the KGB with a small rented room, a mattress on the floor, a stool for my laptop and a Pelican case of camera gear and nothing else (not joking, it was off-putting), I made up with feeling fulfilled. With having people who support you when no one else will, who hold your head when you just want to cry and not judge, who you go out wanting more than anything to make proud with your accomplishments. For me, that’s Jessica and the kids, Lyric & Riley - they’re the best thing that ever happened for me and a realization that the empty feeling I had all those years was the family I wanted to help raise. I know when Jessica and I have our own child together, it’s going be another game-changer that will push me even more to build own my legacy.
As someone who’s the youngest of three kids by quite a bit, a brother 7 years my senior and a sister 10 years my senior, I often longed growing up for the closeness siblings had whom were closer in age. Yet, I also realized that I had built-in mentors to watch grow before me, taking on life, and leaving me to take notes on what to do when it was my turn and with that, we’ve all grown up with our own careers, families, and priorities. Being transparent, when I read that Gary’s brother, AJ, was 11 years his junior, I then envisioned my brother, Anibal, and I. The idea that we would one day start our own business together blows my mind, and more personally, makes me tear up to think about having that connection that I grew up longing for, enabling us to build stronger family bonds. I hope he reads this paragraph and smiles like I am now.
Chapter 6: Hustle
The fact is, we all secretly love to follow those #Entrepreneur, #MillionaireMentality, #HustleOrDie, #EatFuckingFaces type Instagram accounts to feel motivated, but with that said, we all know it’s bullshit. We all feel like we’re just millionaires waiting for the big break, yet don’t really do the shit-touching jobs nobody wants, but are necessary to hit that tipping point. As I write this it’s 3 AM in Vegas and I’m sitting in my hotel bed with my laptop. Why am I even mentioning this? Because with everything going on on this trip, I had to finish this tonight - I didn’t want to, but I knew if it meant staying up all night I would do it. It’s important to really take a hard look inward to ask if you could be doing more. I knew I could do more.
Remember earlier how I mentioned that Gary didn’t open his mouth about his personal brand for almost a decade? He knew the importance of shutting up and just doing the work. To embrace the hustle and make an impact - only then could he rant about shit and command people’s attention whether they liked him or not.
Chapter 8: Jabs & Right hooks
This is another book in it’s own right, Jab, Jab, Jab, Right Hook: How to Tell Your Story in a Noisy Social World, so I won’t ruin it and just tell you that should be the next book you read if you haven’t already. Instead I’ll share the one part of the chapter that stood out the most:
When asked about the best advice to give salespeople in today’s digital age:
Just. Freaking. Ask.
If I were the CEO of Toyota (and I’m being very serious here), my Super Bowl ad would sound something like this: “Hey, I’m Gary Vaynerchuk and I’m the CEO of Toyota. I want you to buy my cars. What do I have to do to make that happen? Let us know.”
Kind of funny, right? Why? Because it’s so simple and to the point, people laugh at how complicated we tend to make really simple things. We’re human - it’s kind of the most proficient thing we do. Instead of over-complicating things, we should strive to stand out by keeping it simple and honest.
Chapter 15: Management
Full-disclosure: I interviewed at VaynerMedia last year after I got laid off. And if I’m being honest, I shit the bed on the interview. Why? Because I wasn’t upfront about being laid off from my last job. Instead, I painted a picture that I wasn’t happy and wanted to move on to have a chance at more growth because I was scared that laid off would just read as: he sucked and was fired. I realized later, it seemed like I didn’t want to be patient, put in the work, and have realistic expectations as an employee. And that’s on me.
Yet the biggest part that made me stop reading and think: hearing that if given the chance to hire a specialist for part of his team or a jack-of-all-trades, he’d hire the jack-of-all-trades. Wasn’t expecting that either, I’m sure. For many of us millennials, as by-products of the new gig economy we find ourselves in, we often do more than just one thing. However, over the years when I kept interviewing for regular jobs, people looked at my resume and said my experience is too scattered, to which I always argued that it was actually a good thing, that it highlighted more life experience I accrued in various fields. While it sounds like a good rebuttal, I never did seem to be able to convince them to look past it and hire me.
When asked about the three values he holds highest in life and looks for in new hires, Vaynerchuk said he had more than three: Patience, Word is Bond, Empathy, and Gratitude. If those four values don’t make for an amazing employee and leader, I don’t know what to believe. Everyone wants to enjoy going to work everyday and to do that, you have to balance all four of those values in yourself and bring them out in others.
Chapter 17: Self-Awareness
As one of the last chapters, it came at a time when I really wanted to ask myself: Do you really know yourself as a whole? All of your strengths, weaknesses, faults, and short-comings? I know, like most people, I struggle with this idea because no one likes to think they could end up not liking what they see.
However, if that is the case you now have the outline of how to change it, how to better yourself. For me, it’s learning to accept myself, my good parts, the shitty ones I sometimes deny, and most importantly - betting on myself, instead of waiting for everyone else to give me a shot. That last one is the hardest for me, because of all the rejection I’ve received over the years. It’s not easy to say you busted your ass in college to do well, went on to grad school, got your MBA, and then couldn’t find work for six years. It makes you really take a hard look at yourself and learn what could you be doing to self-sabotage your success. When do you stop looking for validation in others, and just do your own thing? I still struggle with it, and every few years when I go through the trials of interviews for companies, I wonder why I keep taking my foot off the gas with my own ventures.
Self-awareness is the key to pushing through those glass-ceilings we feel throughout our careers. Knowing what you’re capable of, and how you can improve on your strengths to make them killer. I’m going to keep betting on my strengths that arise as I become more self-aware.
See the whole sad and real part of it is, remembering that everyone unrealistically sees themselves as millionaires just waiting for the big break to launch them into fame and riches as I mentioned earlier. Yet, not even 5% of us are going to really put in the hard, shitty unglamorous work to make it happen. Not the work everyday since 14, make YouTube videos everyday for two years before anyone even watches, 12-13 hour workday away from their family, on a plane every two days type work ethic that Vaynerchuk has been priding himself on to make shit happen. It’s the harshest truth no one wants to hear - you don’t work nearly hard enough to make your dreams come true.
Being honest with myself, I know I felt that way about my career - never being able say I put in the hard work long enough for it to see it’s true potential. The patience portion of the equation only came in as I got older. Which was why when I came up with idea for The Angry Millennial Show, I went all in and put 110% of my attention & efforts into doing the best show possible, traveling around the country on my own dime, sitting with people like Chase Jarvis, Peter Hurley, Brad Lomenick, Chris Sullivan, Michael Paul Smith, & Mickey Cucchiella, all to give listeners the best damn content possible. Who thinks Gary Vaynerchuk should be one of our upcoming guests on the show in the future? Be sure to let him know in an email, Facebook status, Snapchat, tweet, or Instagram post - you know he’s going to see it, but how on-point you are will determine if he’s going to respond or not.
I hope you came away with a better understanding on why constantly educating yourself and never feeling like you have nothing left to learn can only help you. Keep betting on your strengths, and jabbing your way into people’s minds & hearts. You know Gary will.