Your Hustle Isn't Working

Several years ago, I noticed something had changed for Gary Vee, founder and namesake of VaynerX.  In my conversation with Claude Silver, VaynerX, Chief Heart Officer, I learned why.

She told him that what he was doing wasn't working.

As Claude explained the situation to me during our conversation, many of the young men who worked at Vayner expressed anxiety and frustration because they couldn't match Gary’s intense work ethic.

Right about now is where we need to have a heart-to-heart conversation.

I'm going to share about my struggles early in my leadership career. 

My work ethic pushed people away.  

Now, I don't know if it was the motor— the drive to move and do work—I had, or I still have, I do more at a slightly slower pace now than I was 20 years ago, or the intensity I possessed when doing the work.

It pushed people away in a way similar to, but slightly different from, how Gary did.  As Claude mentioned, people felt like they couldn't measure up to Gary.  They were not Gary, and according to that metric, they were failing.  

This week, I have heard in multiple conversations and Roundtable sessions that people are challenged in leading the youngest generation of the workforce.

They are disengaged, act with entitlement, and are unwilling to put in their time.  Yet I know from my own reading and experience that this isn't a new phenomenon.  It's lasted for millennia. Some early Roman military leaders wrote about certain groups acting entitled and believing they were above the work required of their profession.

HUSTLE

Gary Vee was one of the poster children for hustle culture.  It was shared in all his video content, in the Vayner offices, and systematically a part of the cultural lexicon until it wasn’t.

But as she referenced, it was driving a wedge into the company.  Instead of focusing on performing at their best in the pursuit of the mission, they were trying to mimic Gary and falling short.

Gary's incessant focus on hustle took away from his real genius, being empathetic.  And that is what Claude was able to reveal more clearly to him.

Gary's true empathetic nature and desire to have a business with the same value were evident when he asked Claude why she wasn't ‘All-in.’  He was able to sense what Claude thought she had hidden.  She wasn't fully trusting.  She had never had a boss before that she could trust.

The takeaway here - do we have people who are willing to tell us what we need to hear when we need to listen to it?  Or, are we surrounded by people who tell us what they think we want to hear or what helps themselves?

Claude's ability to express to Gary how Gary's demeanor was negatively affecting the youngest team members was born out of empathetic trust.  Gary could have easily doubled down on the hustle vibe and discounted those who felt they couldn't measure up.

He didn't.  In one fell swoop, it was all gone, forever.  Since that day, hustle is not a part of Vayner culture.  And if you've taken in any of Gary’s content over the last 7 or 8 years, you too can almost pinpoint precisely when the change occurred.  It was that abrupt.

At the same time, this further demonstrated that she could trust him, be fully herself, and go all-in on the mission of VaynerX.

Be Yourself at Work

The ability to be yourself at work is everything.  Much to the chagrin of a recent book, “Don’t Be Yourself” (I wish it were a tongue-in-cheek title, but it's for real). Not being yourself is exhausting and defeating.

Trying to be what others want you to be or ‘hustling’ to be what you see others doing completely spoils the entire process of doing what you are best at.

Claude helps people be themselves at VaynerX by fostering an environment of trust and empathy. She encourages self-awareness and personal growth by providing frameworks and support for individuals to explore their strengths and vulnerabilities. 

She emphasizes the importance of showing up authentically and offers guidance to help people navigate their self-discovery journey. Creating a safe space for open conversations, allowing individuals to express themselves without fear of judgment, and connecting them with resources and mentors to aid in their development is essential.

Being myself hindered and separated me from others.  Gary was being himself, which set him apart from others.  Claude was being herself, and it kept her from trusting.

All the while, once it was expressed to me how others experienced me, I realized that was not the me I wanted people to experience.  It was a version of me I was displaying to accomplish a means.

Much the same happened for Gary and Claude.  Then, in an environment of trust, growth, and appreciation, they each rose to a new level.

The same can happen in any and every organization.  It's not about changing values; it's about aligning values and accepting similarities without discounting differences.

In her book, Be Yourself at Work, Claude further shares her personal journey of coming of age.  Not far off the obscurity that Gary is famous for rising from.  It was with diligent, hard work, all aimed at a worthy mission.

With that, she shares these key lessons:

1. Authenticity unlocks performance and connection.

Showing up as your true self—without hiding behind perfection or conformity—creates both personal fulfillment and collective strength. Pretending to be someone else drains energy, while authenticity builds trust, creativity, and meaningful impact. “When we show up, we stop wasting energy pretending to be someone we’re not. Authenticity helps us “unlock our potential, amplify our impact, and unleash the work we’re meant to do.”

2. Psychological safety and trust are the foundations of thriving teams.

Claude, as mentioned already, reinforces that belonging and trust—not just talent or efficiency—drive team success. A team that works together matters more than who is on it. Teams flourish when people feel safe to speak up, make mistakes, and be vulnerable.

3.  Emotional bravery fuels meaningful leadership.

Claude gives a call to lead with heart—emotional optimism, bravery, and efficiency. “Authenticity is not a liability; it’s your greatest strength,” and that courage, compassion, and presence are what leave lasting “heart prints” on others. True leadership isn’t about control or perfection—it’s about being real, creating trust, and modeling vulnerability.

I’ve experienced the same.  Two totally different people with massively different experiences, industries, and so much more.  Both fully and totally aligned with heart.

Find Claude's book here.  Pre-order now to get it next Tuesday, October 28th.

Did you catch this podcast? If not, listen to it here.