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Business Leader Expertise: James Orsini on Perseverance

Riley Smith
Content Contributor
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Business Leader Expertise: James Orsini on Perseverance

Know your strengths, and follow their lead.

This week, UviaUs spoke with James Orsini, President of the Sasha Group, a company in Gary Vaynerchuk’s Vayner X family. James was formerly Chief Operating Officer of VaynerMedia before taking on this role.

He’s spent the better part of the last thirty years in marketing and advertising, despite a start in accounting and Wall Street. He’s been COO, CEO, and CFO of companies of all sizes, as well as a KPMG auditor and Goldman Sachs analyst.

Throughout it all, James has been the type to persevere until he achieves a goal, but he also knows when to let go. In this enlightening conversation, James reveals the role humility and self-awareness have in perseverance, and how all three together can improve your life and career.

We define perseverance as the ability to pursue something, sticking with it despite any setbacks or obstacles. What role has perseverance played in your career?

I’ve got to admit, I didn’t really think about perseverance outright until you contacted me. But I can see how it’s been woven throughout my career.

You know I work with Gary Vaynerchuk, who is very big on the emotional ingredients to success. He’s also very big on perseverance in some way shape or form, whether he refers to it as a form of tenacity or a form of persistence, it’s all a part of getting what you’re trying to achieve.

Both in business and in life! For example, you have to have balance, and persist in fighting for that balance. I do that when it comes to family, work, philanthropic endeavors. You know, everyone wants me 100%.

So you really have to persist and fight for balance, despite any difficulties or delays that may be in front of you.

You mentioned Gary and his ideas about “tenacity.” Working closely with him, what would you say has enabled him to stay the course, despite whatever comes his way?

I’ve got his most recent book here, Twelve and a Half, where he lists the twelve emotional characteristics and ingredients for business success. So there’s all of those.

But what I’ve seen is a consistency in Gary. He’s the same person in the office, with his family, onstage, at a sporting event. No matter where, he’s the same person. 

We’re very, very different, Gary and I, but we’re certainly similar with our consistency. You know that this is what you get, each and every time. 

Because of that parallel, I even went so far as to purchase a VeeFriend, one of Gary’s collection of NFTs. I bought the Consistent Cougar, because I see that similarity in us. 

So consistency has a lot of meaning for you?

Yes, and talking about perseverance, I reached out to Andy, who is the President of VeeFriends, and I said, “You put so many characters together with all these qualities. What are you seeing from the perseverance standpoint?”

He said, “We have the Persistent Penguin and the Forever Phoenix. The phoenix rising from the ashes obviously speaks to perseverance in whatever you’re doing, while connecting with a mythological character from thousands of years ago.”

So tenacity, consistency, persistence, the Forever Phoenix, these are all components of perseverance on this quest to stay determined despite difficulties or obstacles.

When have you seen this quality of perseverance help you do something extraordinary?

When I got to VaynerMedia, which, since day one, has really been a social media advertising company. There I was, stepping through the door, 52-years-old and surrounded by 500 millennials. 

I really didn’t know much about social media. I knew general market advertising, branding, public relations, but social was the next territory for me to conquer. I really had to have perseverance to learn how to do it all!

You reached out to me because you’re following my content, so I must be doing something right! I call that a success story.

How did you learn about social media marketing?

Learning and gleaning whatever I could from the guru that is Gary. 

More importantly, I’m a big believer in reverse 360-degree mentoring. I wrote an article on it. We’re always talking about wisdom and experience and mentoring down, but you know, I learned a lot from mentoring younger people.

I really put that out there as a challenge to other mentors. Be open to learn new things from those you’re mentoring and guiding. 

I don’t believe there’s a substitute for wisdom and experience. I’m certain that's what attracted Gary to me, because that’s what he told me.

But generally speaking, I persistently wanted to learn more. I’ve been comfortable, but I never wanted to stay there.

In fact, when I left to become CEO of SITO mobile, there was an article in Mobile Marketer Magazine with the headline, “What Makes James Orsini Leave His Comfortable Perch at Saatchi and Saatchi to Join SITO Mobile?”

I’ve always felt you have to stretch beyond your “comfortable perch” to be able to learn more.

So perseverance requires a willingness to be challenged?

Yes. I have a friend of mine, Kathy Sharp Ross, who wrote a book called Re:invent Your Life. It’s about people who, at an older age, find a way to reinvent themselves.

I think that’s a big part of perseverance, as well. How do you make the pivot you need to?

Oh, and full disclosure, that 52-year-old guy entering the millennial world is chapter twelve. 

When setting goals, do you believe people should set audacious, “impossible” goals and persevere towards those, or do you advocate knowing your strengths and setting realistic goals?

I’m a big advocate, as is Gary, of self-awareness. He often uses the example, if you’re 5’4’’, you can persevere all you like, but you’re probably not going to make it to the NBA. You know what I mean? Despite your love of basketball and your willingness to put in the work.

I think self-awareness is really important. At the Sasha group, we work with entrepreneurs and founders, and we tell them to surround themselves with people who are not just like them, but rather, those who have strengths where that entrepreneur has a weakness.

Is that why you and Gary work well together?

When he was interviewing me, Gary asked me, “Can you describe what you do in a single sentence?”

And I said, “Yeah, I take dreams and visions, and I make them into action plans.”

He’s like, “Great. You’re hired. I’ve got a lot of dreams and visions.”

I’ve always been an executor. I’m affectionately known as the “shit fixer.” A lot of times in my career, I was dumped into areas that were broken, and people asked me to help them through that. 

But self-awareness isn’t just knowing what you’re good at. It’s also knowing what you enjoy doing.

I told you I was the CEO of a publicly traded company. Not many people could handle that. But you know what, I don’t ever want to do again! 

I’ve been a great Number Two to a lot of successful Number Ones. As a result, I’ve been successful. I read this book called Leading From the Shadows. It’s about being a great Number Two. I was like, yeah, this is who I am. 

So you made a decision on what to persevere toward? How did you make that choice?

Let’s talk about how I got there in the first place. I was surrounded by a lot of people who were saying, “Hey, James, why are you always Number Two? You’re good enough to be Number One. You should be the Number One!”

I met with some recruiters, and they said, “Listen, you’re actually too nice to be Number One. You’ve got to be relentless if you want to be CEO. You’ve got to leave family behind. You’ve got to really be a cutthroat.”

When I resigned from Saatchi and Saatchi to take the position, the then CEO told me, “Three things, James. One, it’s a lonely job. Two, it’s a hard job, because what gets to your desk is the stuff no one else could figure out. And three, where is it trading now?”

I told him, “It trades on the bulletin board, but we’re going to take it up to NASDAQ.”

He said, “Oh, you’ll probably be asked to compromise your morals and integrity on a daily basis.”

I just shook his hand and left. It sounded like he was stuck in some movie fantasy.

Then six months later, I went back, and I was like, Oh my god. How deafening were those words? That’s exactly what I was experiencing. It was a hard and lonely job that had constant pressure to perform. 

When I got in that position, I remembered what I didn’t like about Wall Street when I was at Goldman Sachs. I just couldn’t comprehend their morality. Let me get this straight, I make earnings by a penny, and I’m rewarded. But I miss earnings by a penny, and I am crushed?

You know, who’s probably the more honest guy, the guy who misses earnings by a penny once in a while, or the guy who makes their earnings by a penny every quarter? It just wasn’t for me.

I’m still glad I did it. It’s a badge that not many hold. It’s allowed me to have a better understanding. In the earlier days, when Gary was making really hard decisions as CEO, leading his companies to where they are now, 1500 people globally, $300 million… I know how hard and lonely those decisions are.

I’m the only one in the building who could relate to that. But as for doing it again? I’ll leave that for the next guy.

I would like to serve on publicly traded company boards, though, because I’ve seen the impact that boards have in helping to steer the direction. I’m actively looking for that kind of opportunity.

So aligning your goals with your values is important for perseverance?

Yeah. For me, that was a search. After a 35 year career, I’ve come to the realization that you need to enjoy the process.

In the eighties, when I left the public accounting firm where I was a New York State CPA, I wanted to get to Wall Street. That’s what you wanted to do in the eighties.

Talk about perseverance. I wanted to get to Wall Street, and every recruiter was like, “James. You went to a non-Ivy League School. You’re the son of a plumber from Newark New Jersey. No, man. This is a stretch.”

I was like, “You just have to get me in front of the right person.”

And they did. A guy by the name of Mark Cohen was my recruiter at the time. I got in front of a guy by the name of Ron Hoffner, who I’m still in touch with today, and he took a shot on me.

For a couple of years, I did what I had to do at Goldman Sachs. I was there for Black Monday. It was a scary time, and I saw some things people were doing, and I said, “You know what? This is not the route for me.”

I couldn’t figure out why everybody there was bald in their twenty and thirties, and they told me, “Well, James, because they’ve worked a lifetime already!”

Now, they all had a lot of money, but it takes its toll. It wasn’t for me. So there’s an example of finding and searching.

The same thing happened with the CEO position. So, I became the CEO of a publicly traded tech company. I’d never been a CEO. I knew nothing about technology, and I’d never really been in a publicly traded company. I worked in subsidiaries, but I was never on the frontline. It was sort of an impossible task, and I was the guy they picked to do it.

Do you find there is a generational gap in perseverance? In your experience, do younger people struggle to “stick with it”?

Not at VaynerMedia! In fact, we’re the antithesis of that really. I was just boasting about the fact that as of October of last year, we had a 14.3% voluntary turnover rate in an industry that averages 35%. 

People tend to want to stay here because it’s a people-before-profit kind of environment. Not many places are like that.

You’ve heard me rattle off some great names of the great companies I’ve worked for, but very few of them have that kind of value system. 

When we peeled out the Sasha group, I took seven leaders with me who had been with the company on average for six or seven years. It was “top heavy,” or had more senior employees, because we were running it like a consultancy on the front end and an advertising agency on the backend.

But let’s talk in general. I did sit on the board of Regents for Seton Hall University, so I am close with a younger generation who I would say does have some impatience.

They have what I call the “semester mentality.” Every six months, the bell rings, and they’re ready for something new. I’ve had some younger people come to me and say, “I’m ready to be a creative.” And I say, “But you’re an account guy?” And then he’s like, “Yeah, but I’m ready to try being a creative.”

I tell him, “Most of our creatives are born creative or go to a school of design or something. You don’t just like, become creative.” So I’ve had those kinds of conversations with people. But generally speaking, I think that jumping around comes from a lack of self-awareness. Knowing who you are, right?

If you’re a good second baseman, you don’t need to play centerfield. We’ve got a centerfielder, you’re our second baseman, you’re good right there. You need to know what your qualities are, what you’re good at. Don’t focus on “improving” what you’re bad at.

As Gary says, double down on the stuff you’re good at, rather than, “Let me correct all these things I’m bad at.” Be excellent at the stuff you’re good at, because there will always be a role for you.

I remember when I put my son into private school. He’s a baseball guy, and they asked him, “Kid, can you hit?”

He said, “Yeah.” The coach said, “Well there’s always room on the team for a hitter.” They didn’t even ask, didn’t even care about what he was going to do in the field. They saw he had that one good quality, and because he had that, they made a place for him. “You’ll be in the lineup, don’t worry about it.”

When we’re talking about this younger generation, I suggest they work on finding the one or two things they really do well, and lean in heavily to those, and forget the stuff you don’t do well.

It’s okay. You don’t need to be everything to everybody.

So persevering isn’t necessarily about “muscling through” all obstacles? We should be willing and humble enough to accept ourselves as we are?

Exactly. Knowing your strengths is powerful. My son went on to be captain of his college baseball team. All throughout high school and college, I keep hearing from people, “He’s really coachable.” 

That was important! Not everybody could be the badass superstar who doesn’t listen, but knocks it out of the park. You put up with one or two people like that, but generally speaking, coaches wanted somebody who they could tell, “Hey, do it this way,” and then the kid would actually adapt to that.

I often feel the same with me in the Goldman Sachs example. I wasn’t going to make it. The recruiter was right when he told me that. I was a non-Ivy school, son of a plumber from Newark. 

Okay. I couldn’t change that. But I knew that my strength was, if I got in front of people, I could play up to their level. I was a faster learner than most others with Ivy League degrees. 

I grew up in the house where I was the youngest. My brother is ten years older than me, then a sister fourteen years older, and another sister sixteen years older than me. I knew how to play up to the adults.

I’ll never forget the interview question. “So, James, if you were at a brick wall, and I told you that you had to get to the other side, what would you say to me?”

I said, “Where would you like the wall to move to sir?”

He said, “That question got you hired. Everybody’s telling me they’d break it up into little pieces and they’d get a ladder and scale the wall.” But my comment was, “Where would you like the wall to move to, sir?” That got me hired. He didn’t care that I wasn’t from Wharton, that I didn’t grow up in the Hamptons, that my father wasn’t a banker. That didn’t matter.

Lean in on what you’re good at, and don’t pay too much attention to what you’re weak at.

What are you most excited for the future of Sasha?

I’m excited about how important small and medium sized businesses are to the US in this economy. We’re really helping them with education, consulting, and digital marketing. We’re empowering them for success by teaching first and then counseling them.

We talk about being a Maître d' versus a waitress. We don’t just cook up the order when they give it to us, but we tell them, “You’re asking for an apple, you might want to consider this porterhouse steak.” 

We’re very excited about the future of the Sasha group and its role within the Vayner X family of companies. We affectionately say that the Sasha group is the heart of Vayner X, and our logo prominently displays that heart.

Connect with the Sasha Group

Interested in learning more about James Orsini’s latest venture? Connect online and all social media platforms:

Want to follow James himself? Find him on LinkedIn and Instagram as James Orsini, and @JimmythePencil on Twitter.

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Moderated by UviaUs, the ABM agency for aspirational B2B Growth and Enterprise Brands.

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