James Orsini: The Legend of "Jimmy the Pencil"

James Orsini is the President of The Sasha Group, a VaynerX company named after Gary Vaynerchuk’s father. Working alongside Gary, Orsini leads the group to help small businesses reach explosive growth potential. James has more than 35 years of finance and operations experience across a broad range of marketing and communications disciplines.

James previously served as Executive Vice President and Director of Finance and Operations for Saatchi & Saatchi in New York before moving over to Vayner, where he worked closely with the CEO to provide strategic and day-to-day direction of all financial and operational functions.


This Episode’s Heavy-hitters:

- “A dream without a plan is nothing more than a wish” spoken like a true operator, this is one of James' common words of wisdom to strive for.

- James met Gary Vee through his brother AJ while they were building Vayner early on, and by maintaining that relationship James eventually took a job at Vayner as they were disrupting via the social media space.

- James realized that he was more interested in being an operator than a finance guy while working at Interbrand, when he had the opportunity to focus full-time on a CFO position. He was able to secure a joint CEO position acting as the COO alongside another executive at the company.

- When hiring James to work with him, Gary explained his reasoning: “You’ve made 25 years of mistakes I don’t want to make, so help me avoid the potholes and move faster.”

- The Sasha Group operates so well not because they know about the nuances of every small business– but instead, because they understand each consumer and have the capacity to learn about each business with time and consultation.


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