---
title: "Meet James Orsini, CanvasRebel Magazine"
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summary: "James Orsini shares his 35-year career journey from CPA at KPMG through Goldman Sachs, Saatchi & Saatchi, and Interbrand to his current role building the VaynerX empire alongside Gary Vaynerchuk. He discusses challenges to profitability in the advertising industry, his pivot from leading The Sasha Group to launching vYve by Vayner, an executive training and leadership development initiative."
tags: "advertising, leadership, entrepreneurship, profitability, career-pivot, marketing, executive-training"
key_entities: "James Orsini (person), Gary Vaynerchuk (person), VaynerX (organization), The Sasha Group (organization), vYve by Vayner (organization), KPMG (organization), Goldman Sachs (organization), Saatchi & Saatchi (organization), Interbrand (organization), Siegel and Gale (organization), CanvasRebel (organization), profitability in advertising (concept), leadership development (concept), New York (location)"
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# Meet James Orsini, CanvasRebel Magazine

Stories & Insights Meet James Orsini By Stories & Insights August 25, 2025 0 Comments Share This Article Share Post Share on Facebook Share on Twitter Share by Email Copy URL to clipboard Newsletter Sed ut perspiciatis unde. Subscribe We were lucky to catch up with James Orsini recently and have shared our conversation below. James, thanks for joining us, excited to have you contributing your stories and insights. Let’s jump right into the heart of things. Outsiders often think businesses or industries have much larger profit margins than they actually do – the reason is that outsiders are often unaware of the biggest challenges to profitability in various industries – what’s the biggest challenge to profitability in your industry? Advertising like most service sector companies is based on rates and hours. Our industry has often been their own worst enemy and have been racing to the bottom. They’ve been undervaluing their services for years. But time is money, and ideas are of great value. What about song writers who write a song in 1 hour? Is the value of that song only worth a few hundred dollars? The rate x hours model rewards inefficiency. The longer it takes to do something the more it’s worth?? Speed is punished rather than rewarded. James, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations? I cut my teeth as a New York State Certified Public Accountant. I was an auditor for KPMG 40 years ago and I had Siegel and Gale a branding agency as a client. I remember saying “I could see myself in a place like this someday.” I left KPMG and went to Goldman Sachs where I was an analyst. I got a call that changed my life. They Saatchi Brothers had bought a Public Relations Agency in NYC and were going to build a worldwide company. 5 years later we build the 5th largest PR firm in the world, and I became a global CFO overseeing 31 offices in 26 countries. I left PR to go to Interbrand where I was global CFO for 4 years and North American Chief Operating Officer for 2. I got a call back from Saatchi & Saatchi to become the Executive Vice President of Finance and Operations for their flagship Agency in New York. After 5 years I left to become the CEO of a small publicly traded mobile media company. I did that for nearly 4 years before meeting Gary Vaynerchuk. I’ve been with Gary now for 10 years and have held 4 titles and played 5 different roles in helping to build the VaynerX empire. So, the last 35 years in marketing has seen me in Public Relations, Branding, General Market Advertising, Mobile Media and now social media and digital. I feel fortunate. Have you ever had to pivot? I was recently asked to pivot from President of The Sasha Group an agency which was launched to service small, medium size and challenger brands. Here we built a company to service founders and entrepreneurs with a consultancy on the front end and a digital agency on the back end. We educated, consulted and provided marketing services. I lead this new company for 5 years doubling the revenue and tripling the staff size in that time frame. We prided ourselves on never dipping below a double-digit profit margin. Gary asked me at the start of 2024 to help launch a new initiative. An executive training, leadership development and masterclass offering to help service Fortune 500 marketers and Entrepreneurs. We called it vYve by Vayner and we cross pollinated these two cohorts while teaching them leadership skills drawing from Gary’s two most recent NY Times best-selling books. We bring in speakers from the business world, as well as the wellness world. Yes, Nutrional wellness, sleep wellness, mind and meditation wellness. We are trying to help make more well-rounded team leaders who are empathic, kind and gracious. Any insights you can share with us about how you built up your social media presence? I wasn’t active on social media before I met Gary. In fact, I was 52 years old and joined a company with 400+ millennials. I did however quickly realize there is no substitute for wisdom and experience, and I had both. Working for arguably the most well-known social media guru, I had to take action quickly. When I was in college I had a pencil thin Clark Gable type mustache. As I said previously, I started my career in accounting. These two factors lead to my twitter / X handle of @jimmythepencil. It’s now my TikTok handle as well, and I must admit it gets a ton of attention. I found it best for me personally to bifurcate my social media. If you want my business postings look to LinkedIn, if you want my family postings look to Instagram, if you want my passion postings look to X or TikTok. I write on medium as well and have at least 30 articles there. I’ve done over 65 podcast interviews. These two sources provide a ton of repurposed content for me. Fortunately, people want to hear what I have to say. Contact Info: Website: https://vaynerx.com/ Instagram: @jamesorsini Linkedin: https://www.linkedin.com/in/james-orsini-4b1aaa7 Twitter: @jimmythepencil Other: tiktok @jimmythepencil Suggest a Story: CanvasRebel is built on recommendations from the community; it’s how we uncover hidden gems, so if you or someone you know deserves recognition please let us know here. 0 Likes Share Post Share on Facebook Share on Twitter Share by Email Copy URL to clipboard