---
title: "James Orsini: The Legend of 'Jimmy the Pencil'"
url: https://stacklist.com/card/2204ef6b-295b-44f8-b139-3be4f0547312
source_url: "https://www.thepozcast.com/james-orsini-the-legend-of-jimmy-the-pencil/"
stack: https://stacklist.com/stack/e2657183-cda2-4f70-a71d-40f1eb5a2eb6
summary: "The POZcast episode features James Orsini, President of The Sasha Group, discussing his 35+ years in finance and operations, his journey from accountant to operator, and how he helps small businesses achieve explosive growth. The episode covers key lessons on planning, hiring, scalability, and building invaluable business relationships."
tags: "podcast, entrepreneurship, business-operations, finance, small-business, leadership, growth"
key_entities: "James Orsini (person), Gary Vaynerchuk (person), Adam Posner (person), AJ (person), The Sasha Group (organization), VaynerX (organization), Saatchi & Saatchi (organization), Interseller (organization), Interbrand (organization), Interseller (technology), small-business-growth (concept), financial-operations (concept), The POZcast (event), New York (location)"
classification: "transcript"
content_hash: "sha256:4be63d6baa271ebcb6de55b3299a1bf9f7c1939eb9b7544c2c1f35572c39fa54"
acp_version: "0.2"
token_counts_approximate: 789
visibility: public
agent_accessible: true
status: "final"
---

# James Orsini: The Legend of 'Jimmy the Pencil'

Welcome to our new website! Search Oct. 15, 2021 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. If you enjoyed this episode, please leave a review: https://ratethispodcast.com/thepozcast #thePOZcast is brought to you by our friends at Interseller – the prospecting + outreach platform of recruiters and sellers. Whether you’re doubling down on business development or recruiting talent, Interseller does all the heavy lifting of finding contact data, automating the email and follow-up process, and syncs all that rich data into 20+ CRMs and ATSs. Reach out and get going in a 2-week *free* trial today and let them know you heard about them from Adam on #thePOZcast. Check out a free demo today! https://bit.ly/2Fbm/BZ Show Notes 1:03 - Journey towards Accountant side 2:15 - Evolution of technology 3:19 - Core Fundamental Key Lessons 5:00 - Disadvantage for younger folks 6:03 - New Employees Onboarding Process 9:00 - Passion for Business 10:46 - Learning experience 12:11 - Idea for Execution 13:08 - First Interaction with Gary 16:56 - The Secret Sauce 19:20 - Early Conversation with Gary 22:40 - Scalability 23:00 - Ideal clients for Sasha Group 23:30 - Recruitment for Sasha Group 25:42 - Hardest challenges for small businesses during Pandemic 26:40 - Be Invaluable 27:12 - Initial Process with a new client 29:22 - Happiest in career 30:10 - Long term relationships 35:10 - Legacy to leave behind 35:50 - James's North Star