James Orsini | Scaling an Agency With the Right Hand Man to Gary Vaynerchuk

Sometimes life takes an unexpected turn which can take you to places you never thought you would go. 

Opportunities can arise which could change the course of your life forever. 

Many of us would recoil away from these moments, but James Orsini certainly did not.

After experiencing success in finance and on Wall Street, James had an opportunity for big change and decided to work with Gary Vaynerchuk, a wine critic who transformed himself into a social media guru. And he hasn’t looked back. 

James Orsini is President of The Sasha Group, a VaynerX company. James has been working with serial entrepreneur Gary Vaynerchuk for many years and iterations, beginning as Chief Integrations Officer for VaynerMedia before moving on to be COO, and now for The Sasha Group.

In this week’s episode, John sits down with James to talk about how he came to work with Gary Vaynerchuk, the differences between healthy and unhealthy growth of a company, and why it’s important to focus on one thing when you are starting out in business or marketing.

In this episode, we also talk about:

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  • How James Came to Work With Gary Vaynerchuk
  • The Story of How James Had the “amorphous” Title of Chief Integration Officer Becoming Chief Operating Officer of VaynerMedia
  • The Difference Between Healthy Growth of a Company and Unhealthy Growth of a Company
  • How The Sasha Group Came to Be
  • Who The Sasha Group is Named After
  • The Reasons Why James Went From COO to Working With The Sasha Group
  • What James Does is More than Consulting
  • The Criteria James Follows for Selecting Companies to Work With
  • Market in the Year in Which You Live
  • How James Uses Social Media
  • Why Gary Vaynerchuk Likes LinkedIn Right Now
  • The New Little V Cartoon Series
  • The Power of a Personal Brand
  • When Starting Out, You Need to “Pick a Lane” and Get Great at One Thing
  • Will Gary Ever Buy the Jets?
  • With Social Media, You Need to Make a Lot of Content
  • Who James Thanks for His Success

Resources Mentioned:

Sponsor: Rise25

Today’s episode is sponsored by Rise25 Media, the done-for-you lead generation service to get you a steady flow of new leads, prospects, referral partners and strategic partners coming in the door every month, month after month.

Rise25 Media was created by myself and my business partner, Dr. Jeremy Weisz, and is part of our mission to help connect more entrepreneurs with their ideal prospects and referral partners.

We do this through lead generation and proactive outreach, and we do this through our done for you podcast service, which is the #1 thing I’ve done in my business and life.

To learn more, book a call with us here.

Check out Rise25 to learn more about our done-for-you lead generation and podcast services.

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Episode Transcript

John Corcoran  0:40  

Alright, welcome everybody. My guest on this show is James Orsini, whose name you may not know. But he’s basically I’m going to say it the right hand man to another name, you probably know. And that’s Gary van der Chuck. Gary was nice enough to be a guest prior guest on my show a number of years back. James is the president the Sasha group, which is part of the Gary van der Chuck umbrella of companies. The Sasha group, mentor startups from a million to 100 million in revenues. We’re going to ask him all about that it’s relatively new initiative that they’re working on now. But previously, he was CEO for Vader media during a stretch in which they quadrupled in size and revenue. And vendor media, for those of you who don’t know is one of the largest independent social media digital advertising agencies out there. He also has nearly 30 years of experience in social and mobile media advertising, brand management, poker relations and Wall Street. So but first before we dive into that, this podcast is brought to you by rise 25 media, which is our done view boutique, lead generation and podcasting agency, helping b2b businesses to get a steady flow of new leads, prospects, referral partners and strategic partners coming in the door, month after month. Right. So Dr. Media was created by myself and my business partner done Dr. Jeremy Weiss. And it’s part of our mission to make the world a smaller place by creating connections helping to connect more entrepreneurs and business owners. They’re ideal prospects and referral partners they love to work with. So To learn more, visit us on the web at rise 25 calm or book a call with us to discuss your lead generation options at rise 25 dot com slash call. All right. Now on to the show. As I mentioned, my guest is James Orsini we recently connected over LinkedIn, you’re generous enough to come on the show. And now James, I want to ask you, and I want to ask you here so you seem like a really reasonable guy, humble guy. You’ve got deep experience in finance and Wall Street. Did your your family just think you were absolutely nuts? When you said I’m going to go work for this madman who you see all over social media. What was that conversation? Like?

James Orsini  2:39  

Yeah, it was kind of wild. I mean, I didn’t really know Gary, I must admit, I knew his brother AJ, I had sat next to AJ at a Seton Hall University basketball game about 10 years ago. That’s how we met. And we just kind of got to talking. And, you know, I was Chief Operating Officer Saatchi and Saatchi at the time. He I invited him down to you know, take a look around, see what it’s like when you get big. he graciously accepted it. And then we just kind of stayed in touch. And, you know, I’d like to say I was a little mentor to him. Asked me, you know, somebody that does? How would you do this? Have you ever done that? You know, so we stayed in touch over the years. I was CEO of a publicly traded mobile media company and called AJ because my developers had developed a product that they thought was right for Facebook. And he’s like, Yeah, come on, in. And I went in, there was a big company, there was like, 250 people back when I visited him. And after leaving the mobile company, I called AJ to just say, Hey, I’m going to be back and big advertising I’ll see in New York. And he was like, Jeffrey, me, my brother Gary. And I said, No, to Jeffrey, here, my brother Gary. And I said, No. All right, well, why don’t you Google? And he’s not gonna be hard to find. So I did mean, wasn’t.

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