My Journey with Gary Vee
November 1, 2023
It was back in the nexus of 2012 and 2013 when the world of marketing began to captivate my professional curiosity.
At that time, I was part of Slagle Roofing, where I contributed to scaling the business into the bustling residential market. As serendipity would have it, Gary Vaynerchuk's spirited
clips
on YouTube caught my eye, infusing a blend of innovative marketing tactics and an invigorating sense of self-confidence into my approach.
This marked the beginning of what would become a decade-long odyssey, a period where learning about brand dynamics and marketing strategies became as routine as morning coffee. The creation of The Big Fish Contracting Co in 2015 was a decisive leap, driven by an ambition to craft a brand that transcended the typical expectations of a trade-focused enterprise. It was imperative that our brand resonated with memorability and that our commitment to customer satisfaction was unparalleled.
Navigating through the digital deluge of Gary's extensive content became a challenge, yet his philosophies resonated with me, echoing in the corridors of my mind, encouraging me to press forward. His discourse on the burgeoning field of cryptocurrency prompted me to take a calculated risk, leading to my initial investment in Bitcoin. This financial foray rekindled another passion of mine: the art of trading baseball cards, a hobby that not only reconnected me with my childhood joy but also allowed me to forge connections with fellow enthusiasts across the nation.
My rendezvous with Gary in 2019 at The National was nothing short of momentous. In Chicago, I willingly paid a premium for a Michael Jordan autographed rookie card, not as a mere transaction but as a passport to express my gratitude for the inspiration his content had granted me. The exchange culminated in a treasured selfie and my Gary Vee KSwiss shoes, emblazoned with his signature, became a cherished memento.
2021 was a pivotal juncture for my entrepreneurial journey. I was self aware of the fact I needed to find an integrator that could complement my vision and I partnered up with Rob Tokay. His financial endorsement was a tangible vote of confidence in the vision I held for Big Fish And of myself. It was with this bolstered support that I ventured into Gary's NFT venture, VeeFriends , where the spirit of camaraderie and community further fueled my desire to empower others.
In response, I launched The Big Fish Cares podcast , a platform designed to rally the entrepreneurial spirit in others, showcasing that perseverance paired with belief is a potent formula for success. VeeCon in 2022 was a testament to this philosophy, an event that exemplified the collective power of a community bonded by shared aspirations. At VeeCon 2023, I had the honor of initiating a CEO panel, a moment that crystallized my belief in the power of dreams. My recent exchange with Gary at this year's National Sports Card Convention was yet another landmark, I traded him a stack of Veefriends cards so I could interview him in his iconic office in NYC.
This podcast episode is not just another installment; it is the essence of my entrepreneurial journey, and I invite you to be a part of it. Your subscription, comments, and emails are not just appreciated—they are the lifeblood of a community that thrives on mutual support and encouragement. As much as you are there for me, know that I am unequivocally in your corner, cheering you on every step of the way.
This marked the beginning of what would become a decade-long odyssey, a period where learning about brand dynamics and marketing strategies became as routine as morning coffee. The creation of The Big Fish Contracting Co in 2015 was a decisive leap, driven by an ambition to craft a brand that transcended the typical expectations of a trade-focused enterprise. It was imperative that our brand resonated with memorability and that our commitment to customer satisfaction was unparalleled.
Navigating through the digital deluge of Gary's extensive content became a challenge, yet his philosophies resonated with me, echoing in the corridors of my mind, encouraging me to press forward. His discourse on the burgeoning field of cryptocurrency prompted me to take a calculated risk, leading to my initial investment in Bitcoin. This financial foray rekindled another passion of mine: the art of trading baseball cards, a hobby that not only reconnected me with my childhood joy but also allowed me to forge connections with fellow enthusiasts across the nation.
My rendezvous with Gary in 2019 at The National was nothing short of momentous. In Chicago, I willingly paid a premium for a Michael Jordan autographed rookie card, not as a mere transaction but as a passport to express my gratitude for the inspiration his content had granted me. The exchange culminated in a treasured selfie and my Gary Vee KSwiss shoes, emblazoned with his signature, became a cherished memento.
2021 was a pivotal juncture for my entrepreneurial journey. I was self aware of the fact I needed to find an integrator that could complement my vision and I partnered up with Rob Tokay. His financial endorsement was a tangible vote of confidence in the vision I held for Big Fish And of myself. It was with this bolstered support that I ventured into Gary's NFT venture, VeeFriends , where the spirit of camaraderie and community further fueled my desire to empower others.
In response, I launched The Big Fish Cares podcast , a platform designed to rally the entrepreneurial spirit in others, showcasing that perseverance paired with belief is a potent formula for success. VeeCon in 2022 was a testament to this philosophy, an event that exemplified the collective power of a community bonded by shared aspirations. At VeeCon 2023, I had the honor of initiating a CEO panel, a moment that crystallized my belief in the power of dreams. My recent exchange with Gary at this year's National Sports Card Convention was yet another landmark, I traded him a stack of Veefriends cards so I could interview him in his iconic office in NYC.
This podcast episode is not just another installment; it is the essence of my entrepreneurial journey, and I invite you to be a part of it. Your subscription, comments, and emails are not just appreciated—they are the lifeblood of a community that thrives on mutual support and encouragement. As much as you are there for me, know that I am unequivocally in your corner, cheering you on every step of the way.
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By Benny Fisher
•
August 20, 2026
I walked into a leadership meeting with a client's team about a year into working with them. Twelve people around the table. Everyone had a status update. Everyone gave their status update. An hour later, we had a shared understanding of what had already happened and nothing had been decided. That is not a meeting. That is a group status email that required everyone to show up in person. WHAT A REAL LEADERSHIP MEETING DOES There is a version of the weekly leadership meeting that most teams never experience. One where the issues that have been bouncing around in people's heads all week get named out loud, get owned by the right person, and get resolved before they become next week's bigger problem. That version requires three things that most teams skip. First , the issues have to be named honestly, not diplomatically. Diplomatic issue identification produces incomplete lists. What you are actually worried about has to be said in the room, not saved for the parking lot conversation after. Second , they have to be solved at the right level. Most of the time the founder is not the right person. A mature team asks who is actually closest to this problem, and puts the solve there. Third , the priorities have to stay honest. Most leadership teams do not need more ambition. They need fewer things on the list, held with more discipline. When every item is labeled important, people quietly stop believing anything actually is. WHAT CHANGED WHEN THEY CHANGED THE MEETING We rebuilt the format with that client. Same people, same time slot, different structure. A short pulse on the numbers, a review of what moved and what stalled on the real priorities, then time to identify and solve the actual issues, not report on them. Three things happened in the first month. The founder stopped carrying half the company's unresolved issues home over the weekend. The team started solving things without waiting to be told. And the leadership conversations shifted from status reporting to real decision-making. The meeting did not fix the business. It created the conditions for the team to fix the business themselves. THE QUESTION TO BRING TO YOUR NEXT MEETING Before your next leadership meeting, write down the three things you are most worried about in the business right now. Not the agenda items. The real things. Then ask: do these get named and solved in our weekly meeting, or do they stay in my head until they become a crisis? If the answer is your head, the meeting needs to change. A business that still depends on the founder's nervous system to hold its unresolved issues has not yet built a real leadership team. It has built a group that reports to a person. What is sitting in your head right now that belongs in a room with your team? Prepared by Benny Fisher | Visionary Navigator | bennyfisher.com



