If you haven’t heard of Gary Vaynerchuk by now, you’re likely not listening. He’s an entrepreneur inflamed with the same fiery competitive spirit as some of the fiercest athletes on the planet.
Vaynerchuk’s a serial entrepreneur, operator and investor. He was an early investor in Facebook, Twitter, Uber, Venmo, Tumblr, Resy and more. He co-founded VaynerMedia and Vaynersports, agencies servicing Fortune 500 companies and world-class athletes everywhere. Between the two businesses, Vaynerchuk employees over 600 people.
His rise to prominence began in the late 1990s when he helped take his family wine business from $4 million to $60 million in annual sales. Today, he’s one of the most sought after public speakers and venture capitalists, and a four-time New York Times bestselling author. And get this — Vaynerchuk didn’t crack open a book until after high school.
Vaynerchuk’s a competitor. On our Suiting Up Podcast, he went as far as to say that he’s unbeatable. With a guest as dynamic as he, distilling 60 minutes of motivation and metaphorical roller coasters into three takeaways can be difficult — but I think we got it. Here are Vaynerchuk’s three keys to increasing your winning percentage.
1. Find your edge.
By definition, resilience is your capacity to recover quickly from difficulty. The more resilient, the better your ability to endure, and eventually win. Vaynerchuk hates to lose, calling himself “outrageously competitive.”
One of the best ways to identify your strengths is to uncover your origin. Vaynerchuk wasn’t born in the U.S., telling me he was once an outcast, couldn’t speak English and was a 4’11” eighth-grader who got picked on. He was destined to prove people wrong.
Today, he’ll be the first to tell you he’s not your classic entrepreneur. Instead, he’s developed skill sets that differentiate him from his competitors. He’s crafty, a practitioner and tenacious. He told me he’ll be known as one of the best entrepreneurs of his time because he “knows how to communicate, distribute content and loves people.”
2. Get creative.
Vaynerchuk told me, “The reason most entrepreneurs can’t beat me is they want to compete with me in math, and I beat them in coloring.” He uses his creativity and emotional intelligence to find solutions. When addressing a market, he’ll begin with identifying macro trends, then hedges his predictions using micro implementation.
For example, in media, Vaynerchuk foresaw the impact the iPhone would have on a connected content consumption marketplace. At a micro-level, he hedged his bet and became a first-mover in video, capitalizing on YouTube. This catapulted his Wine Library sales and led to confident, early stage investments in Facebook and Twitter.
His next big prediction? The resurgence of audio as transformative mass consumption.
3. Fight unfair.
Vaynerchuk stopped focusing on his schoolwork in the 6th grade. He knew the traditional education system was a categorical weakness of his, but his entrepreneurial spirit was his strength. He opened his first lemonade stand when he was 10, turning it into a franchise with multiple locations. When he was in middle school, Vaynerchuk purchased thousands of dollars in football and baseball trading cards, then resold them on the secondary market for sizeable profits.
When most stick to the traditional school system and start their entrepreneurial career in their twenties, Vaynerchuk decided to punt on school and start his entrepreneurial life at age 10. He got a head start. Vaynerchuk told me to “better your strengths and punt your weaknesses.” When he fights unfair, he doesn’t break the rules. He’s thinking outside the box, leveraging his strengths, and burgeoning his enterprise value.
Having met Vaynerchuk several times, watched him on YouTube, read his books and listened to his podcasts, it’s worth noting that what you see, hear and read is exactly what you get in person. To be a successful entrepreneur, I recommend personalizing Vaynerchuk’s three keys with high intensity, integrity and authenticity. There will be a number of folks that try to get in your way or slow you down, but if your mission is your truth, you’ll win — and be happy about how you got there.
Hosted by professional athlete and entrepreneur, Suiting Up with Paul Rabil is a podcast that explores the psychology, playbook of tools and strategies of the most influential people in sports, entertainment and business. Navigating each conversation, Paul unpacks how world-class performers think, compete, improve, operate, train, eat and sleep.
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