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As I considered topics to write about for this week, my team suggested writing about things I’ve learned from Gary given how long we’ve worked together. It was a wonderful idea, and I was quite excited to reflect on the experience since it will be 15 years next week! Except, I then realized, it was only 14 years, which is a great lesson in and of itself…


Lesson #1 – It’s Never Too Late

I started working with Gary in 2009, when he published his first book, Crush It, and in that book, he outlined what would later become the Influencer Economy. His theory was anyone could make a living being an online expert, in any subject matter. Nine years later, in his follow-up, Crushing It, he told the stories of people who did just that.

The people who were able to take advantage of this new digital economy all had one thing in common. They got started! They didn’t wait for the perfect opportunity. They didn’t wait for the market to develop. They didn’t wait for someone else to prove it was possible. They had belief in themselves and got to work.

Often motivating people to work harder, shift careers if they are unhappy, or realize an opportunity, Gary always implores people to realize how much life they have left ahead of them. It’s important to have a proper perspective and be ambitious. Regardless of the project, if you start tomorrow, you’ll lose a day. If you started last year, think about how much further along you’d be. It’s truly never too late to start!


Lesson #2 – Authenticity is the Key to Connection

Profane, foul-mouthed, vulgar. I’ve heard Gary described all of these ways, and couldn’t disagree more. Does he curse? Sure, but it is never done in a derogatory way, or for the sake of profanity. Rather, it is authentic to who Gary is and the way he talks.

Gary has built a reputation and brand by being able to connect directly with people through his social media and from the stage. He has amassed a sizable following because he speaks from the heart, and is truly authentic.

In the speaking business, the best speakers are just that, authentic. Audiences are smart. They can tell when someone isn’t being true to themselves. Being authentic isn’t easy either, it takes self-awareness and a willingness to fail, but so many of the most successful people in business have built their careers by remaining authentically them.


Lesson #3 – Don’t Fear Failure

To take a line from Gary’s own official bio, “He is a prolific angel investor with early investments in companies such as Facebook, Twitter, Tumblr, Venmo, Snapchat, Coinbase, and Uber.” However, he relishes the opportunity to remind people he could have invested $25,000 in Uber in the earliest of rounds, which would have been worth about $300 million at one point. Suffice it to say, we see all the successes but often forget the failures. 

While he is quite prescient, he has had plenty of failures along the way, and it never holds him back from trying new things if he believes in them. It could be timing, operational issues, technological problems, or any number of things, but you cannot be afraid of trying something you believe in for fear of failure. 

At VaynerSpeakers, we are regularly making changes behind the scenes when we see a better way of doing things. We aren’t afraid of something not working out, but rather experiment and recalibrate based on what we learn along the way. If it doesn’t work, we know we tried something and have new learnings to use for our next endeavor.


Lesson #4 – The Power of Empathy in Leadership

Many view leadership as being about strength, authority, and decisiveness. While these traits are important, Gary’s leadership style is grounded in empathy. He values his team’s emotional well-being, understands their unique challenges, and appreciates their perspectives.

I’ve learned that leading with empathy promotes loyalty, motivation, and productivity. It fosters an environment where employees feel valued, understood, and are more willing to contribute their best efforts.

I find that empathetic leadership means empowering people to perform, which builds trust in both directions and allows your team to grow having learned many valuable lessons along the way.


Lesson #5 – Patience and Long-term Thinking Win

Gary’s mantra, “Macro patience, micro speed,” encapsulates his philosophy of working hard daily while maintaining a long-term vision, and believing in your macro philosophy. He acknowledges that real success takes time and isn’t achieved overnight.

From Gary, I’ve learned that short-term wins are important, but investing time and effort into long-term goals pays off in more substantial ways. Patience, perseverance, and a strong vision are the cornerstones of lasting success. It’s okay to recalibrate, but don’t lose sight of the big picture.


Gary has not only been my client for 14 years, but my friend. He is a great partner who is there when you need him and doesn’t micromanage. There are hundreds of lessons I’ve learned, both big and small, that are not just applicable in business, but valuable life lessons. 

It’s been an honor to learn and grow alongside Gary. If these lessons can impact you in any way similar to how they’ve influenced me, I’ll consider this a success.

Remember, life is a marathon, not a sprint. Be yourself, without being afraid to fail. Understand and connect with those around you, be patient, and always keep an eye on the future. Embrace these principles, and you’ll set yourself up for enduring success.