Mentoring To Iron Out Your Plans and Grow Your Business and Your Income

Last Updated on April 26, 2021 by Owen McGab Enaohwo

There’s nothing more precious than a good teacher, mentor, and guardian.

A person who understands the ins and out of a concept or idea and helps you understand them as well.

Today’s guest, James Orsini, is just that kind of mentor. In today’s episode, he tells us about his mentorship organization.

He explains how his organization helps clients identify and work through difficulties in the running of their business, and about himself, what it was like switching from one business line to another.

Listen to the audio interview

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Show Notes

0:05 – Introduction

0:26 – Dr. Jeremy Weisz shares the best solution that makes documenting standard operating procedures drop-dead easy, highlighting a 14-day free trial. No credit card required.

1:38 – Dr. Jeremy talks about James Orsini, who works alongside Gary Vaynerchuk and is president of The Sasha Group.

2:11 – Mr. Orsini introduces himself.

2:58 – Mr. Orsini shares more about himself, explains his philosophy, how he got hired, why he does what he does.

5:22 – The guest talks about some of the mistakes he helped VaynerMedia and The Sasha Group avoid.

7:50 – The guest speaker talks about what he did at VaynerMedia, and how he transitioned to The Sasha Group.

14:45 – Mr. Orsini talks about Stork, and a little about client profitability.

18:35 – Mr. Orsini talks about the limit of the number of people he allows to attend the Stork meetings in person, and he explains how his team handles each person individually.

19:08 – The guest shares the biggest breakthroughs he’s seen in clients as a result of what they learned at the virtual/live classes.

20:02 – Mr. Orsini explains how he decided on the pricing for the subscription to Stork.

21:51 – The guest tells the story of how Stork was born.

23:30 – Mr. Orsini shares where we can find the podcast Building While Flying.

25:30 – Mr. Orsini explains why he initially wanted to charge more for the Stork subscription fee.

27:34 – The guest speaker tells us what the transition was like, switching from VaynerMedia to The Sasha Group.

29:29 – The guest talks about the VaynerMentors.

31:24 – Mr. Orsini explains how he came up with the pricing structure for his business.

32:48 – Mr. Orsini talks about a great podcast his co-worker Gary did on behind the scenes of mentors.

34:06 – The guest mentions websites where he and the organization can be reached.

35:02 – Mr. Orsini explains how his hope is that companies he helps double their income, come back and hire him again, so he can manage their marketing.

36:41 – The guest gives examples of some of the types of clients he’s worked with.

37:18 – Mr. Orsini talks about the framework the business is built around.

38:24 – The guest speaker tells us about the influence Gary’s dad had on The Sasha Group, and talks about his encounter with him.

40:06 – Mr. Orsini talks about the Eisenhower Matrix, a decision-making tree that allows you to prioritize what’s in front of you, and how he’s applied it to his work.

44:51 – Mr. Orsini tells us at what point in the effort/profitability matrix is ideal for deciding which clients to focus your energy and money on. He also explains that less “ideal” clients have an important purpose in a company, and he tells us what that purpose is.

47:10 – Outro

Guest Profile

James Orsini works alongside CEO of VaynerMedia and entrepreneur Gary Vaynerchuck as the president of VaynerMedia.

He was previously chief operating officer for one of the largest independent social media digital advertising agencies.

Having studied accounting at Seton Hall University, he has various skills such as business planning, contract negotiations, product marketing, and many more.

Transcript of the interview

Speaker 1: Welcome to the Process Breakdown Podcast, where we talk about streamlining and scaling operations of your company, getting rid of bottlenecks, and giving your employees all the information they need to be successful at their jobs. Now, let’s get started with the show.

Dr. Jeremy Weisz: Dr. Jeremy Weisz here, host of the Process Breakdown Podcast, where we talk about streamlining and scaling operations of your company, getting rid of bottlenecks and giving your staff everything they need to be successful at their job. Past guest, you could check out episodes with David Allen of Getting Things Done, Michael Gerber of the E-Myth and many, many more. I have an amazing guest today James Orsini of The Sasha Group. Before I introduce him, this episode is brought to you by SweetProcess. And if you’ve had team members, James, maybe you can relate to this, ask you the same questions over and over. And maybe the 10th time you spend explaining it, there is a better way, there’s a solution. SweetProcess is actually a software that makes it drop dead easy to train and onboard new staff and save time with existing staff. And when I was talking to the owner, Owen, not only do universities, banks, hospitals and software companies use them but first responder government agencies use them in life or death situations to run their operation.

Dr. Jeremy Weisz: So you can use SweetProcess to document all the repetitive tasks that eat up your precious time. You can focus on growing your team and empowering them. And you sign up for a free 14 day trial. No credit card is required. But at, it’s sweet like candy S-W-E-E-T I’m excited today, we have James Orsini President of The Sasha Group. He works alongside Gary Vaynerchuk, the serial entrepreneur. He was CEO at VaynerMedia, which is a full service digital marketing agency working with fortune 500 clients. They work with clients like Budweiser, Toyota, Pepsi, and many more. And James was previously COO for one of the largest independent social media digital advertising agencies. He’s been in the space for a long time. I don’t want to date you or anything, James, but thanks for joining me.

James Orsini: If you’re showing video I am dated.

Dr. Jeremy Weisz: Listen, you have more hair than me, so it’s fine. If people don’t know your story, and oftentimes people ask “How’d you connect with it? How’d you get to it?” It was a random occurrence at Seton Hall game where you met AJ. He brought in, and you gave them advice along their journey and then all of a sudden you walk in their office, you’re like, “Whoa, you guys have lots of staff here.” And you formed a relationship together. I’m wondering that initial conversation because AJ brought you in, Gary wants to talk to you. You met Gary and then you have dinner. And you said a line that I love. And I’ll let you say it not me, but about dreams and visions. So he asked you about your background and you said what?

James Orsini: Yeah. He said, “Can you describe what you doing a single sentence?” And I said, “Yeah, I take dreams and visions, and I put them into action plans.” And he was like, “Hey, you’re hired, I got a lot of dreams and visions.” I think the important thing about what you’re saying there with AJ and the years before, is I was simply in a position to help and advise even though there was nothing in it for me for multiple years. I didn’t do it because there was something in it for me, I did it because I had some wisdom and experience and they needed some questions answered.

Dr. Jeremy Weisz: Yeah, I mean, if anyone follows Gary Vaynerchuk, that’s his philosophy, is helping people no matter what and just giving the people and lending your advice. And that seems like is your philosophy as well?

James Orsini: Yeah. And that’s why it wasn’t tough to find that we were kindred spirits, you know what I mean? When we when we got together, I realized that this is someone who’s passionate about this. We’re very, very different that’s for sure.

Dr. Jeremy Weisz: How so?

James Orsini: I mean, look, he’s a type A personality, he’s happy that we’re at 100 miles an hour, I’m a little more measured. I said, “Gary you’d be the type of guy that would jump out of a helicopter to go skiing and I go down the Bunny hill at Shawnee here, and wear helmet to do so.” So that’s the difference.

Dr. Jeremy Weisz: Well, I mean, it’s a COO, probably integrator mentality more than a visionary mentality, right?

James Orsini: That’s right. It’s being able, there’s nobody short of good ideas, it’s they’re short on the execution. Like how do you execute and actually get into market and that’s what I specialize in.

Dr. Jeremy Weisz: Yeah. One of the things that struck me when I was listening to you talk was, you talked about when Gary brought you on, he’s like, “I want to avoid 25 years of mistakes.” And you with Saatchi & Saatchi and SITO. All your experience in the space, I’m wondering what were some of those. Take me back to some of the mistakes that you helped VaynerMedia and now The Sasha Group avoided because what you saw?

James Orsini: Well, he was pretty clear, when he hired me, he said, “I want to build a $500 million integrated, international, independent, communications, company, can you help me do it?” And I said, “Yeah, I think I can.” So let’s take international as an example, when he said, “I want to be International, where do we start?” And I said, “Great, don’t do it like I did. You don’t need to be 31 offices in 26 countries.” I said “They’re still trying to close down stuff that I opened in the early ’90s.” So I said, “You could service the world from a couple locations.” And we talked about the first one being London, and the second one being Singapore. So he servicing Europe, if you will, from from a London post and an Asia right now from a post in Singapore, both offices are doing well. So that’s one example.

Dr. Jeremy Weisz: Keep going I can listen to this all day, James. So International, not 31 offices, two offices. What’s another piece that you remember, as an example?

James Orsini: Yeah. Remember, when I first got there, they weren’t really doing any kind of television commercials. They were doing social media posts and he wanted to understand, remember he’s not an advertising guy, so he’s a retailer by trade. And he wanted to understand how does it work? And I said, “Well, it goes storyboard, animatic, focus group, throw it away, do it again, storyboard, animatic, focus group.” And he said, “Yeah, well, that’s horrible.” He said, “We’re going to do three Facebook videos. So all of them are working on behalf of the client, and then we’re going to take the one that’s performing the best, and we’re going to tweak it up and bring it to television. And in that one example, he broke 150 year old model in like, 90 seconds. So this is-

Dr. Jeremy Weisz: I guess, you have to know the rules to break them, right?

James Orsini: Well, that was it. That was kind of what the role that I played for many years there, was just helping them to understand, how does it work in the industry? Remember, I was in public relations and branding and general market advertising and mobile and he wanted to do a little bit of everything.

Dr. Jeremy Weisz: Talk about what you did at VaynerMedia. And then we’ll talk about the transition to The Sasha Group.

James Orsini: Yeah, so early on he made a comment of, “Hey, I just want you to breathe my culture and my company. We don’t need to come in and tell me everything that I’m doing wrong here. It’s not about that. I want you to understand how we do things here. I sat in a lot of meetings, I sat in meetings were he presented, I sat in meetings where it was just he and his brother talking about operations at the time. Remember, when I was first hired, I was hired as what he called the chief integration officer, because his brother AJ was the chief operating officer. And he gave me that title because he said it’s amorphous enough to have you play in whatever I need you to do. So the first thing was the move to Hudson Yards. He handed me a manila envelope and had a sheet of paper and he was like, “Get this done.” It’s a move to to Hudson Yards.

James Orsini: And quite frankly, the deal that was there was not going to be a good deal for us. I said, “I don’t think you could do this, it’s going to bankrupt you.” So he was like, “Okay, great. Well tell me what I need to do.” And that included prices per square foot and security deposits and things like that. And he went back and renegotiate it and we got what we needed to move into to Hudson Yards. We worked on building out offerings within the company all really to his vision and then executing and getting him in. Build out a production studio in Long Island City, which was another really interesting project. And most importantly, built out a leadership team with a lot of chiefs around the table, chief strategy officer, chief financial officer, chief production officer, chief media officer, chief heart officer. A lot of those, chief marketing officer, many of which were personal contacts of mine, that he spent some time with and they were right for the fit.

Dr. Jeremy Weisz: It seems like they don’t… Yeah, go ahead.

James Orsini: Well, I was going to say, and then one day he just decided like, “Hey, you ready to start something new?”

Dr. Jeremy Weisz: What do you say to that?

James Orsini: I said, “What do you have in mind?” And he said, “Well, I’m on the cover of Entrepreneur Magazine, I got 10 million followers and we built a company to service fortune 500. I don’t have a company to service these small medium sized businesses.” So said, “I want to start a new company, I want to name it after my father for legacy purposes.” That’s where we got The Sasha from. And he said, “I think you should run it.” So off we went, we’ve been two years into the process now.

Dr. Jeremy Weisz: It’s amazing. Yeah, I was going to say, James you’ve been in this industry for a long time, but for most observing, it seems like a daunting task to hire all these larger leadership positions, was it something that you hired all at once? Or how did you prioritize it as you were hiring for these leadership positions?

James Orsini: Well, as the business grow. So when I got there it was, I think, 400 people over 42 million in revenue. I believe it ended probably close to 200 million last year, maybe 1000 People. So as the company matures, the needs expand and as his vision expands, the needs expand. So when we first got there, he didn’t have a great appreciation for creative as he does now. He got a better understanding of branding and creative and that led to the need for chief creative officers. With creatives come the need for improved strategy and insights, which then led to chief strategy officers. The two that he has in place now were both the Saatchi folks, in their past they’ve great caliber. Then he wanted somebody scale him on the marketing side.

James Orsini: So he needed a marketing officer and the one that’s in place there was from Interbrand. And clearly, he needed a strong finance as you’re now going to go international and double the size of your company. And so, as the chief financial officer, the gentlemen, I knew from from my Saatchi days as well. Then they build out a studio, need a chief production officer. So we have a gentleman who used to work at McCann, he certainly knew that media belonged with the creative. And then he hired a great chief media officer. So they just come it’s not like… But the first one that he really made a commitment to was the chief heart officer to scale him on on the cultural side.

Dr. Jeremy Weisz: Love that. What do you look for… You knew the person previously the chief financial officer, as you’re growing so quickly, and also having more products, another company. What do you look for in a chief financial officer, if someone out there looking to hire one?

James Orsini: So, remember, I told you nobody showed a vision. It’s the execution of division. So he wanted to be a $500 million integrated, international, communications company. So I said, “I’m going to introduce you to this guy. When I knew him, he oversaw something called Team One at Saatchi, which was the only integrated company that we had within our offering. So with advertising, public relations, events, marketing, all under one roof. He was International, he lived in both London and in Singapore. And you want to be 500 million. He’s currently at Sapient Consulting, and they’re $500 million. So your future looks like somebody like this.” So that’s how you execute against a vision.

Dr. Jeremy Weisz: Love it. You mentioned offerings, all right. And also when you go into the Hudson project, you’re looking at making sure it’s profitable and everything’s working as it should. So I wonder if you talk about project or client profitability, and maybe we talk about STORK. And I’d love to talk about virtual 4D after that. So because you launched STORK, tell me about STORK?

James Orsini: Yes. So, STORK is a membership model, it’s not a subscription model. And the difference is the membership model gives you access to the full database of content as opposed to a subscription model, which says “You get it from this point forward.” So we had been talking about it for a while, we talked about a SaaS product. A product that keeps delivering, because when you talk about the other topics that you want to get into, that’s for any service sector company. A labor realization client utilization, a client profitability labor utilization. Those are all service sector companies. But a SaaS product is ongoing revenue. So we wanted to come up with a product where it was short tactical videos that come out on a Monday, five to 10 minute videos, followed up by additional written content on the topic that comes out on a Wednesday and culminates in a Friday asked me anything live chat.

James Orsini: So yeah, you can dial in and talk about the whatever, Monday’s topic were. And it could be, how to find a local influencer for my business, how to advertise I’m podcasting. I did one a couple weeks ago, which was how to write a business plan. So we launched it during the pandemic as a free service because so many people would now work from home, they were pivoting their business, quite frankly, they were lost. So we launched it for several months as a free a model before flipping the switch to a paid model which is still reasonably, priced is $300 a year for all the content. And we’ve had about 450 plus people sign up so far in a couple of months that we’ve been running it as a paid model. It came from, the other things that you mentioned, which is our 4Ds. Our Daily Digital Deep Dive and think of it like a day in the life and in a Disney or Zappos sense, where you’re going to come in and really get a full immersion. I think would be the best way to say it. It’s eight in the morning till six at night, when it’s live. It’s pricey, it’s 12,000 a seat in New York, and various prices, whether it’s held in London, or LA or Chattanooga, Tennessee.

James Orsini: And then what happened was, the pandemic came, and we couldn’t run anymore, we had run 20 of them very successfully. And now we needed to figure out how do we pivot to a virtual room. Gary is in the room as well, so he offers a real value as they go around. But we condensed it, we lowered the price to now 4000 and we limit the number of people that are in there, so they get the personal attention. And we covered things like all the platforms, how the consumers consume the content, and the platform’s, creative development, personal branding, culture. And then Gary is for a session that runs usually 90 minutes of the four or five hours that the program runs. So we had one yesterday, again, sold out, March 4 will be our fourth virtual 4Ds that we’re conducting.

Dr. Jeremy Weisz: So talk about James, the people limit online versus in-person, how many people do you allow?

James Orsini: We allow anywhere from six to eight. And then typically, what happens is some of those people will bring a plus one. So we had that happen yesterday two brought one extra from their team to sit in. So we like to keep the boxes on just one screen if we can, you know what I mean? And it allows you to go around the room and allows Gary to handle a pointed question about your business.

Dr. Jeremy Weisz: What are some of the big breakthroughs you’ve seen in that live or virtual?

James Orsini: Oh, well, I mean, I’ve seen business models change, I’ve seen direct consumer approaches launched, I’ve seen podcasts launched, I’ve seen books written as a result of what they’ve learned in that room, remember we don’t ask them to do anything that we wouldn’t do ourselves. And we have Gary as a great model for that. So we are sharing some of his success stories and what’s worked for him live and open, right there in that room. And I had a gentleman from yesterday’s meeting, send me a note back that he had 42 takeaways from his four and a half hours, 42 things that he was going to be following up on personally.

Dr. Jeremy Weisz: That’s amazing.

James Orsini: Yeah, I’m pretty well.

Dr. Jeremy Weisz: How did you decide on pricing of STORK?

James Orsini: So we did a lot of homework on that actually. We were in Beta for probably 11 months prior to that. I originally wanted it to be much more than what we actually landed on. But we determined that we were going to have certain things that we give back to our community that are free, like we just launched a podcast now, Building While Flying, that will be free content. And then there were certain things that we really felt that they should have been paid for. And STORK came about because we didn’t have a product for sub $1 million businesses. So we wanted to keep them in our ecosystem, in hopes that they would get to the 3 million mark or more.

Dr. Jeremy Weisz: They graduate from STORK to virtual 4D to hiring the agency for full time ]done for you stuff.

James Orsini: Exactly. I mean, that’s the blueprint. The Sasha Group runs a little differently than VaynerMedia, because VaynerMedia is predominantly an agency. Sasha Group runs like a consultancy. So it’s a consultancy on the front end, and an advertising agency in the back end. So I was able to take some of my experiences from KPMG and Goldman Sachs and Interbrand, which are more consultative in their offering. And marry it up with the experiences of MSL Group, or Saatchi & Saatchi, which ran more like an agency.

Dr. Jeremy Weisz: And so you’re doing these live virtual 4Ds and then virtual 4Ds. And you are thinking, well, we need something to serve the other businesses that can’t come to this, and that’s where STORK was born?

James Orsini: Yeah. And it was also we did a lot of surveys. So we surveyed the 4D alumni who had already had an experience with us found real value. And what we found was they said, “Wow, I got so much it was like drinking from a firehose, I often don’t know where to begin.” So I was like, “Okay, so we’re going to give them tactical, how to videos, on topics that we cover in the 4Ds.” So, here is how you begin right here. here’s how you do media buying on Facebook, here’s how you find the influencer for your local restaurant. Here’s how you could advertise on podcasting. So tactical how to videos.

Dr. Jeremy Weisz: Yeah, I could see both ways. I could see someone coming to the 4Ds experiencing going,” Listen, I’m going to join STORK just keep up with everything.” And I can see vice versa, someone joins STORK and go, “I want to do the 4D experience.”

James Orsini: So if you do a 4Ds and you then sign up for STORK that day or the day after, you get it at the founders rate, which is half the price. So a 4D member is going to get a STORK for the same price that the founding members did, and that’s $150 a year. I mean, come on $150 a year.

Dr. Jeremy Weisz: It’s a no brainer.

James Orsini: It’s a currently no brainer.

Dr. Jeremy Weisz: You get one idea that gets you a half a customer, and it pays for itself for the year.

James Orsini: Absolutely, and then-

Dr. Jeremy Weisz: And I’m wondering about… Yeah, go ahead.

James Orsini: And then you could still get free content from us by listening to our podcast. Building While Flying.

Dr. Jeremy Weisz: Yeah. So give a shout out to the podcast. Where can people find Building While Flying? Where can they go?

James Orsini: Yeah, our first session actually launched last week. And it’s on Apple, it’s on Spotify. Building While Flying, it’s hosted by Katie Hankinson, our Senior Vice President. Oversees our branding, as well as our international business.

Dr. Jeremy Weisz: I thought you’d say you? I would have been you in there?

James Orsini: No, because, we’ll get on that topic, but I’ll tell you why it’s not me. And Mickey Cloud, who runs the Sasha South. So he’s the Executive Director of the Sasha South office down in Chattanooga. I’m not hosting it, because it wasn’t my desire to host it. These two had an actual personal development goal to want to launch a podcast and I said, “Great, I’m going to help you do that.” And we’re going to do that, you saw that in one of the articles that I wrote on 2020. A Dream Without a Plan it’s Nothing More Than a Wish. It was on our Eisenhower Matrix that we would launch a podcast in 2020. So these two really drove it home. They were interested in voice and podcasting as an outreach. We leveraged my network to come up with the first four or five guests. And now we’re going from there.

Dr. Jeremy Weisz: I’m excited. Everyone should check it out, I’m going to check it out. And I want to talk about pricing for a second but I will ask about Eisenhower Matrix. I don’t know if you can see this that is top of my notes list here to ask you about the Eisenhower Matrix, because it’s kind of a framework that you didn’t come up with but you use. But back to the pricing first, because I’m fascinated by your thought process with this, James. You said, “I wouldn’t have charged 300, I would charge more, because it’s obviously worth a lot more than that for the year.” What were you thinking?

James Orsini: Well, we were also balancing the fact that Gary gives away a lot of free content and he’s noted for that. So we were walking a fine line, this is the first time he’s allowed one of his subsidiaries to charge for a SaaS type model, if you will. So we needed to know, okay, this is one we’re giving it away for free, this is one we’re monetizing it. So we looked at it as a feeder, into into The Sasha Group. Remember, our goal is to get clients to outgrow The Sasha Group and grow into VaynerMedia. So it’s all this this feeder thing and we continue to develop products that are right for a sub fortune 500 audience. And we found that in surveying many of the clients that we walked away from.

James Orsini: And when I say walk away from it, because when Gary announced The Sasha Group, we had 4700 inquiries in the first 48 hours. So when we peel back the onion, 3000 of them were businesses below 1 million in revenue. And we really didn’t have a developed product for that. So STORK is our first attempt at that. And now, in 2021, we have a new product for them coming out of our consulting division where you can buy a package of consulting hours, 20 hours, 60 hours and then we will rotate in the leader that’s appropriate for your question. Is it a creative hour, you talk to a creative, isn’t a media hour need, you’ll talk to media, is it business, you’ll talk to me.

Dr. Jeremy Weisz: Yeah, it’s really interesting. What was the transition like, now you’re in VaynerMedia, you go over to Sasha Group, what was that transition like? Basically you are a startup at that point?

James Orsini: Yeah. So when Gary and I discussed it, I said, “Look, a few things Gary, let me let me not run it, like a mini VaynerMedia, let me run it differently.” This is where we talked about the consultancy versus agency model. We run it on three pillars which are education, consulting, and digital marketing. I asked for the Chattanooga office. And I think that was a surprise for him.

Dr. Jeremy Weisz: Why?

James Orsini: Because he said, “Why do you want Chattanooga?” And I said, “Well, because I feel like every time I go down there, we’re selling sunglasses in Seattle, and we should be selling umbrellas.” And I said “We’re trying to sell into big clients and there’s a lot of small, incubated Silicon Valley-ish type companies down there.”

Dr. Jeremy Weisz: It made sense.

James Orsini: So he allowed me that. I wanted to take over a few things that I was familiar with, and help launch like, the 4Ds and the educational side, and the mentors program. Very interesting program on the consulting side, if we have some time, we should talk about that. So I wanted to take over some of the things that I helped sort of co-authored with him and he was cool. And then I over indexed on senior people, because that’s what a consultancy does. So I had eight vice presidents and above for a small company and only had 30 people in at the time that we did it. And the question was, can you actually make money with all these heavy salaries? But I knew the model that we were running and we did, in fact, make money in year one, and we made more money in year two.

Dr. Jeremy Weisz: Talk about the mentor side. So we have STORK, we have the 4D. And then talk about that.

James Orsini: We have something called VaynerMentors. This came up in a breakfast that Gary and I had, I think it was probably 2018. And he said, “James, I want a consulting offering to help with small business. I want like a Deloitte ask kind of offering. And I want to be able to take a piece of the upside if we help them break through their problems.” Why would you come to Vayner or The Sasha Group now for that serve? Because we’re going to use Gary’s model of explosive growth, and we’re going to have you see yourself as a media company first. So you’re a media company happens to manufacture nail polish, you’re a media company that happens to sell corporate snacks, you’re a media company that that happens to be a furniture retailer. So that’s what we did.

James Orsini: And we looked for businesses that had been around at least three years that were doing about 10 million or more in revenue. And that had plateaued. Either they were not growing as fast as they wanted to, or felt that they can grow faster than what they currently were. And we charge a fee for it. It’s the only place in VaynerX where Gary’s actually written into the scope of work. So you get an hour of Gary’s time on the front end and half hour of Gary’s time on the back end. Together, we determine what are the pillars for growth that will move your business, we deploy them over a couple of months. And then we stay in the game with you for three years. And if we break through, if we help you surpass what would have been, that you could have done on your own without us, then we take a share and a piece of the upside.

Dr. Jeremy Weisz: How do you decide to structure that piece?

James Orsini: Well, I quite frankly, came up with that structure. And it was that if it’s based on a profit goal, like let’s say you were doing $10 million in revenue, you were producing a 10% margin. So that’s a million bucks, and you paid me 200,000, for the consulting services, I would add that back, and now the million goes to 1.2 million. You can grow that 10% without me so then it goes to 1, 3, 20 and we sharing anything above that 50/50. There’s others that we’re already growing on the top and bottom line and said, “Listen, I need you to help me grow more.”

James Orsini: Then we take a percentage of the revenue in excess of a particular target as if we were a salesperson getting a commission. So what we found is that we’re in the game for three years, because typically year one, there is no share because you’re kind of doing what we asked you to do. You’re making some investments and stuff like that. There’s a modest share in year two. And then if all things go well, we win when you win in year three.

Dr. Jeremy Weisz: Love it. It’s a win-win situation.

James Orsini: Absolutely. There’s a great podcast that Gary did on that, Behind The Curtain of Mentors. Because the first mentor that we had completed his three years now. And we helped him to double, his target was double his business in three years. So he wanted to go from a $10 million nail polish manufacturer to a-

Dr. Jeremy Weisz: I know Habib, actually. Actually I interviewed him and this was pre-working with you guys. We had a conversation after I interviewed him, I’m thinking it was like the time when he was thinking about doing this mentorship. And then he had emailed me in the middle he said, “It’s amazing.” And I didn’t realize what happened on the other side.

James Orsini: Yeah, it exploded. He exceeded 20 million in year three.

Dr. Jeremy Weisz: That’s amazing.

James Orsini: He was selling to licensed cosmetologist, in nail salons and we help them go direct to consumer which was brilliant. Because obviously during the COVID, all the nail salons closed and everybody was doing it yourself at home. We don’t have a crystal ball to predict the future. But we do have a good feel for business. And he reaped the benefits of that and we reap the benefits alongside him.

Dr. Jeremy Weisz: James, where can people… Should they just go to The Sasha Group website? Where can they find out more about the mentor site?

James Orsini: Yeah, that particular one, thesashagroup is our website. All of these offerings are on there, you’ll find that about STORK, you’ll find out about it 4Ds, you’ll find that about mentors. All of our handles are thesashagroups on LinkedIn, on Twitter, on Instagram. You’ll find each of those, Facebook as well. So I mean, we’re pretty public about all those. In fact, I just posted something today on LinkedIn because another one of the mentors completed his three years and put a little video montage together as a thanks and post it on LinkedIn. I reshare it today.

Dr. Jeremy Weisz: Nice, I’ll check it out. Does that keep going after the three years? I know it’s a three year plan but it like “Okay, James we’ve doubled, bye or like let’s double again for three years.”

James Orsini: My hope is that they come back and hire me now as an agency, you know what I mean?

Dr. Jeremy Weisz: Got it.

James Orsini: Actually do the marketing for them. And in the case of Habib, here’s his journey because it’s an interesting journey. He talks to a friend who says “You should really check this guy, Gary Vaynerchuk out.” So he sniffs around, he looks at the YouTube video, he inquires a little bit about the mentors, about the 4Ds. He comes in for 4Ds, he gets value from the 4Ds. Inquires a little further, he joins mentors, he gets value from mentors, he asked us to help him find some staff members, we actually helped recruiting for him. The business has taken off now, he’s got a pivot some of his content for direct to consumer, he comes to us for video. So he’s been in and out of hallways over the course of three or four years. And when he exceeds his capacity in media buying or planning or video content production, my hope is that he comes back. In fact, Habib went so far as to recommend a friend. So we have another gentleman, Sasha, who owns Harvest Dental, who is a current mentors client right now. And that was a recommendation of Habib and his brother Greg.

Dr. Jeremy Weisz: So a company that’s maybe stagnant in growth for a couple years and is typically north of 10 million. Is that a good mentor side client?

James Orsini: Yeah, absolutely. We serve as clients up to up to 50 million in that space. So we’ve done furniture retailer in Panama City, Florida, a $20 million corporate snacks company at Parsippany, New Jersey, we’ve done that insurance company out of Miami. People always ask, “What do you know about insurance?” And I said “Nothing, but I know more about the people that purchase all your stuff than you’ll ever know. So that’s why you come to me. You know what I know and I know what I know.”

Dr. Jeremy Weisz: Yeah. Well, you have a framework that business is business, I guess, and you have a framework that you can lay on top of the business.

James Orsini: Well, it’s interesting you said that, because after we built a studio in Long Island City, it wasn’t running the way Gary wanted it to run. And he called me in as the chief operating officer said, “Listen, I need you to go and run the production studio in Long Island City.” And I said “Gary, I never ran a production studio before.” And he goes, “It’s a business and you’ve run a business go over and fix it.” And I was like, “He’s right. It’s a business and I’ve run businesses before. So let me go on.” And I spent six months there and that’s that led to the the hiring of our chief production officer. Yeah, so I’m also affectionately known as a shit fixer.

Dr. Jeremy Weisz: That should be your LinkedIn importation.

James Orsini: I had it on my Twitter handle, but it was upsetting some people from the church.

Dr. Jeremy Weisz: Not, [kissing 00:38:09], right? Before we get to the Eisenhower Matrix, I want to talk about… You mentioned legacy with The Sasha Group, right? It’s called The Sasha Group for Gary’s dad. Talk about Gary’s dad’s influence and you probably get to know-

James Orsini: Yeah, you know it was quite an honor when Gary bestowed that upon me. And he did tell me “I want you to go and spend some time with my dad who runs the Wine Library in Springfield, New Jersey. A Belarus, Russian immigrant who came over. And just a wise man, a strong man but yet gentle. And really gave the liberty to his sons to be more than just heirs to a retail liquor store. Really allowed them to do much more with your life. In fact, encourage them not not allowed them encourage them to do that. So yeah, he’s first guy to get any of the swag that we make that has the Sasha name on it. I make sure I drive it there personally and give it to him. And we don’t spend a ton of time together but he’s proud of what it is that has his name on it here and I take that very seriously. And look to make sure that we continue the legacy.

Dr. Jeremy Weisz: Love it. Thanks for sharing that. The Eisenhower Matrix, you have an amazing post that I suggest anyone check out which is on Medium. I don’t know if it’s on your website also. And you talk about the Eisenhower Matrix, and you’re hitting your goals by using it.

James Orsini: Yes. So this is something that I’ve used for many years really. Started back at Interbrand, used it at Saatchi as well, certainly used it SITO and now I brought it here to both Vayner and in The Sasha Group. And it’s just this decision making tree that allows you to prioritize what it is that’s in front of you. So helps you separate the important from the urgent. I’ve used it in the case of client plotting graphs. So if one side represents revenue, and another side represents a marquee value to the agency and plot our clients that way, that’s how we use in Interbrand and Saatchi. I’ve used it to help determine effort, if the y-axis represents money and the x-axis represents the amount of effort it takes. It helps me see where we are spending time.

James Orsini: So I’ll give you a few examples. Before using a client plotting graph at Interbrand, we were winning 33% of the business that we pitched. After instituting the client, a matrix and understanding how much we were willing to invest in a client in each one of the quadrants, meaning not every client opportunity was the same. We increased our hit rate to 67%.

Dr. Jeremy Weisz: Wow, what were the quadrants? What did those look like?

James Orsini: It may have been greater than 10 million in the upper right hand corner, and high marquee value. So a client name that you would have heard of like General Electric as an example. And it becomes clearer in the move to Saatchi when we use a similar client plotting graph and the upper right hand corner were to clients that we were known for, like Procter & Gamble and General Mills. And then there were some that weren’t spending as much money. But we’re still notable clients, like Ameriprise, or JCPenney. And then we began to say, “Great, so we don’t need every client in the upper right hand box.” If we came down to the lower box and said, “Hey, these are marquee clients, these are great to have in the first and second quarter, because we may be able to get them to grow to be clients in the upper right hand box, okay.”

James Orsini: Then there was upper left hand box where nobody really heard of the client per se, but they were still giving us good money. That’s great in the third and fourth quarter servicing, because money is green, nobody cares how you make your budget, they could care if it’s on Reynolds Rap, right?

Dr. Jeremy Weisz: Yeah.

James Orsini: And then the lower quadrant, where you would say, “We don’t ever want a client in this lower quadrant. Because it’s not a lot of money and nobody’s ever heard of them.” And I would say, “Yeah, but that’s the training ground for your next level of managers.” And what they would see, like they did in VaynerMedia, London was, “Why is your leadership spending so much time on these clients in the lower left hand box? It’s not meant for your leadership, your leadership should be spending time in the upper right, or in the in the lower right.” This is a training ground where you don’t care if it blows up, per se you know what I mean? This is how your next level of account director moves up to vice president or an account sup becomes an account director by servicing some of these smaller clients.

James Orsini: So a healthy mix of clients was what we were demonstrating there. Now, let’s move to The Sasha Group, when we first started, the head of media came to me said, “Okay, James, I need to hire seven more people.” I said, “We’re not hired seven more people. We’re not going to build a kingdom of media here.” That is a model that’s worked very well in VaynerMedia, where they had 300 people service and 300 million in media. So I said, “I want you to plot the clients based on effort and profitability. And each time that you come to me for hire, I want you to exit a client that is taking a lot of effort and bringing a little profitability.” And that’s how we held the headcount the same and increase the profitability of the company.

Dr. Jeremy Weisz: At what point do you assess that effort in profitability? Once you bring your?

James Orsini: Yeah, you’re assessing it based on three months in and how’s it working and if you’re grinding on it. Now, there were some that he wanted to exit and I said “You can’t exit those. And he said, “Why?” I said, “Because I’m making a lot of money on the creative with those. So I understand you’re not making the money in the media, but that’s okay because I’m looking at the portfolio and my money is being made on the creative. That is one that you will not exit. Pick a different one.”

Dr. Jeremy Weisz: Yeah. In that situation, they didn’t have full picture of the whole, all the scope of services that were being done?

James Orsini: That’s the role I play. That’s why they pay me.

Dr. Jeremy Weisz: I love it. Yeah. Because in the article, you talked about the urgent and important, important but not urgent, urgent but not important and neither urgent nor important. This is for plotting goals.

James Orsini: Right. So that was… In November of 2019 I met with Gary and we talked about what this 2020 look like for The Sasha Group. And I said, “I think we could do 12 or 13 million in revenue.” And he said, “How are you going to get there?” And at that time, I couldn’t say it’s these clients. So I said, “We’re going to do these things that should result in our getting to 12 or 13 million.” And, and he said, “Great.” And he moved a couple of the dots around and reprioritize them and he said, “Okay, let’s get these done.” And we did, that’s the purpose of the article. We got every single dot addressed and as a result of that, we landed right where we’re supposed to be in a COVID environment.

Dr. Jeremy Weisz: James, I love it. I want to be the first one to thank you. This has been fantastic. Everyone should check out They should check out your podcast Building While Flying. Are there any other places we should point people online? Obviously, you can check out-

James Orsini: Yeah, my personal stuff. So I am @JimmyThePencil on Twitter.

Dr. Jeremy Weisz: Why JimmyThePencil pencil?

James Orsini: That’s a story for another day.

Dr. Jeremy Weisz: Makes me think of a [crosstalk 00:46:52].

James Orsini: It’s story for another day. But do we remember I am in New York state so [crosstalk 00:46:57].

Dr. Jeremy Weisz: Don’t mess with JimmyThePencil.

James Orsini: Yeah. And James Orsini on LinkedIn and Instagram.

Dr. Jeremy Weisz: Awesome. Thanks, James. I appreciate it.

James Orsini: Great, thank you. Good to see you.

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2 responses to “Mentoring To Iron Out Your Plans and Grow Your Business and Your Income”

  1. james orsini says:

    This was really well done. Thanks for the opportunity to share

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