Makes Sense - with Dr. JC Doornick

How to Stay Relevant When the World Changes Fast with James Orsini - E-177

51 min
Jun 9, 2026about 1 month ago
Listen to Episode
Summary

James Orsini, a veteran business executive and advisor to Gary Vaynerchuk, discusses staying relevant amid rapid technological change, drawing parallels between the AI boom and the dot-com era. He emphasizes profitable growth over explosive scaling, the importance of human skills and side hustles, and the critical role of patience and fundamentals in navigating business transformation.

Insights
  • AI adoption mirrors dot-com bubble dynamics: companies are being rewarded for playing in AI space without proven business models or profitability, risking widespread failure like early internet companies
  • Profitable, sustainable growth outperforms explosive scaling; healthy companies maintain double-digit profit margins while growing steadily, avoiding the trap of growth-at-all-costs that leads to bankruptcy
  • Human skills like curiosity, kindness, financial literacy, and trade expertise (plumbing, electrical work) become more valuable as AI automates routine tasks, creating opportunity for those who develop these competencies
  • Career reinvention at any age is possible by mapping strengths, skills, and passions rather than relying on past resume; side hustles aligned with passion create optionality and can become primary income
  • Leadership is shifting toward kindness, flexibility, and meeting people where they are; hybrid work models and human-centered approaches outperform rigid, fear-based organizational cultures
Trends
Return to analog and human interaction: live events, in-person dining, and phone-free spaces gaining traction as counter-movement to digital saturationEntry-level knowledge work (paralegal research, document review) facing displacement; demand shifting to roles requiring human judgment and oversight of AI outputsRise of side-hustle economy as primary career strategy; individuals building parallel businesses around passion while maintaining stable employment for risk mitigationAgentic AI replacing traditional organizational structures; some companies moving from large teams to small groups of AI agents, creating disruption in live events and service sectorsFinancial literacy becoming essential life skill; gap in education creating opportunity for advisors and educators serving founders and business ownersPersonal brand importance increasing; authenticity and consistency across channels becoming competitive advantage as AI-generated content proliferatesShift from extreme positions to 'purple' middle ground; balanced approaches (hybrid work, blended digital/analog, patient growth) outperforming polarized strategiesFailure as business model: companies hiring consultants to fix failures; failure recovery and organizational restructuring becoming specialized service category
Topics
AI adoption and business model sustainabilityProfitable vs. explosive growth strategiesCareer reinvention and future-proofingSide hustle and gig economy modelsHuman skills in AI era (curiosity, kindness, financial literacy)Trade professions and automation-resistant careersLeadership philosophy and organizational culturePersonal branding and authenticityHybrid work and return to analogEntry-level job displacement from AIPatience as competitive advantageMentorship and knowledge transferLive events and human interaction valueFinancial literacy education gapOrganizational failure recovery
Companies
VaynerMedia
Gary Vaynerchuk's advertising and media company where Orsini served as advisor; contrasted with Sachi for fearless, c...
Sachi & Sachi
Advertising agency where Orsini ran the Sasha Group division, growing it from $10M to $20.5M in 5 years with consiste...
Goldman Sachs
Wall Street firm Orsini left in the 1980s to pursue public relations, demonstrating early career pivot away from lucr...
Rowland (public relations firm)
Boutique PR firm Orsini joined from Goldman; grew to become fifth largest PR firm globally under his financial leader...
CEDO Mobile
Publicly traded mobile media company where Orsini served as CEO; achieved cash flow break-even ahead of schedule but ...
Factotum
UK-based company partnering with Orsini and Bobby Lane to expand US operations; targeting $30M revenue in 3 years wit...
Vibe
Executive travel and learning platform co-founded with Andrea Sullivan; generated $1M revenue in first year after rap...
Merrill Lynch
Investment bank that rewarded dot-com companies for occupying market space without profitability, illustrating bubble...
IBM
Cited example of company that paused junior hiring then realized it would lack future managers; demonstrates unintend...
Priceline
Dot-com era survivor company that successfully transitioned from internet bubble, contrasted with failed competitors
eBay
Dot-com era survivor company that built sustainable business model, contrasted with failed internet startups
Apollo Global Management
Hedge fund making recent investments in live events, validating human interaction and in-person experiences as valuab...
People
James Orsini
Guest discussing career evolution, AI adoption parallels to dot-com era, and strategies for staying relevant during r...
Dr. JC Doornick
Host conducting interview with Orsini about business relevance and change management
Gary Vaynerchuk
Orsini's long-time mentor and business partner; referenced throughout for leadership philosophy, family values, and b...
Dr. Larry Marks
Orsini's first boss and mentor in his 80s; maintained relationship over decades; attending Orsini's daughter's wedding
Bobby Lane
Partner with Orsini on Factotum expansion; met Orsini after failed merger integration in London; seeking $30M revenue...
Andrea Sullivan
Created Vibe concept during COVID for executive travel and learning; partnering with Orsini to build commercial busin...
Jim Kwik
Met Orsini at Creative Con; launching 'genius campaign' focused on human intelligence as counterpoint to AI
Richard Heider
Wrote 'Consigliari: Ruling from the Shadows' book that influenced Orsini's understanding of number-two leadership role
Quotes
"I like leaving when people are throwing rose petals and not rocks. Every time that I've left, I was really at the height of my game in the particular environment that I was in."
James OrsiniEarly in conversation
"You can't cut your way to growth. Oxymoronic."
James OrsiniMid-conversation on AI growth
"It feels painstakingly similar to me as the dot com implosion in 2000, 2001."
James OrsiniDiscussing AI era
"I embrace the fundamentals to achieve success. There's a difference between swelling and growing. Both get your big one is healthy and one is not."
James OrsiniOn profitable growth
"Fail fast, fix fast, learn fast."
James OrsiniOn failure philosophy
"I take dreams and visions and tournament to action plans."
James OrsiniDescribing his role with Gary Vaynerchuk
Full Transcript
Have you noticed that the world that we live in has been doing most of the thinking for you? That your beliefs, perceptions, reactions, fears and doubts have been shaped by unsolicited outside noise? How easy it's been for you to slip into that default sleep walking mode and label it as life and reality. Yeah, that ends here. Welcome to the Make Sense with Dr. JC Podcast. This is your opportunity to start thinking for yourself, reclaim control and step back into that role as the shock caller and dominant force of your own reality. It's when you change the way that you look at things that the things that you look at begin to change. So let's wake up, let's rise up and let's make sense of why and how shift happens. Welcome to the Make Sense with Dr. JC Podcast, Mr. James Orsini. I also call what you have just entered the dragon's lair. So welcome. That sounds great. Thank you. Good to be here. I always start off as a way of getting people caught up. In the introduction, I've mentioned all of the wonderful things that you've done and we're going to get into some of that. But my first question is, what is it like to be James Orsini these days? It's a good life. I have a beautiful family that I love spending time with. I've got some great friends, have had and continue to have a great career. It was funny because I was on a call right before this. And I said, I'm in touch with every boss I've ever had. And the guy was like, really? And I said, yeah, I said, and if you think about it, I had to quit everyone to go on to the next role that I had. I've been fortunate enough to do it in such a way that everybody feels good about it and still there to help whenever they need. In fact, my first boss and mentor will actually be a guest at my daughter's wedding on August 1st. Wow. I've been in the wash years with this guy. That says a lot about you. Funny that you say that and it encompasses a chapter of my book, but my first mentor, his name is Dr. Larry Marks and that whole story is really funny. But he's in his mid to late 80s now, but this is a guy that I speak to very frequently. If I called him right now, he would call me back within five minutes. And all I do is I just call him up and I thank him so much. But what's interesting about what you just said is there's this general consciousness that you're supposed to stick with the same people in the same company. I don't know who made that up, but it makes sense that we evolve and we move on to the next thing. So that's great to hear you say that. Yeah, especially if you feel it's in your growth path. Not like, hey, I'm going to do exactly what I was doing here right over there now for your competitor. Yeah. You know, I think for me, it was a lot of zig and zagging throughout my career and everyone that I was with understood why I was doing the next thing that I was doing and supported my growth. Not part of my set questions, but you just triggered this in my brain. How do you know when it's time to move to the next step? You know, I like leaving when people are throwing rose petals and not rocks. Every time that I've left, I was really at the height of my game in the particular environment that I was in. It was never really a reason to leave. But the advice and counsel that I give to students and everything is, it's okay to take a call. Always take a call. You know, not that I'm looking to leave or have myself out there or I'm on a job board or anything like that. But it's always helps to listen. And there were times where I listened, didn't take the role and put somebody I knew in the role. You know, it was so funny because in that mentor situation that I just mentioned to you, he had lost his role in the company that we were in. He was on the sideline. I got a call from a role and then I said, I called him up. I said, listen, this role is beneath you. But the guy that's above is pretty much my peer. So I'd be kind of stuck. If you take the job, you will quickly outshine the guy above. And I'm relatively certain that they're going to put you in that role. And that's exactly how it played out and why we continue to be friends and colleagues all these years later. His most successful role was a role that they called me for. What I love about that, and it kind of makes me want to apply for a job to work for you because it would indicate that you as a mentor or a boss would probably be trying to raise me up to leave, you know, like we would a child. I would assume that that's part of what you try to do with the people that you mentor is. Absolutely. And then I support them for success in their next lifestyle. So I ran a company for Gary called the Sasha Group. We had seven really senior leaders, all but two have left now and are outside of Gary's hallways. And I do what I can to position every one of them to be successful. But I did learn a lot about leadership and about empathy and kind candor and all that from being close to Gary for so many years. You just made me realize that I got to set a new goal that one day people will refer to me as just JC and everyone will know who I am. Gary, Gary, you know, Sort of like Cher. Yeah, exactly. I want to be like a shacker at Gary. I want to talk about what I find so fascinating. You know, I had the opportunity to hear you speak at Creative Con and ever since then I've kind of been stalking you a little bit and learning more about you because you're somebody that has so much experience and you've, you know, you're such a powerful source of knowledge, almost like a historian or like a sommelier of business and all these things that you've been through. So I want to talk a little bit about the speed of change right now. You know, we're going to try to make this a little bit of an advisement from the great James Orsini. So you've already survived multiple business revolutions. You know, it's unbelievable what you've been through and grown through as well. Does the AI era, which is everybody's topic right now, I find the human behavior is more fascinating than ever. Does the AI era feel fundamentally different to you or from your experience? Is it just another version of managing rapid change? It feels painstakingly similar to me as the dot com implosion in 2000, 2001. Wow. Okay. I remember reading a prospectus for a company and in the prospectus it said, we do not know how to make profit. If we do make profits, we will not sustain profits. And that was a company that IPO at 11 and closed at 121. And I remember going to a friend of mine, Merrill Lynch, I'm saying, look, I write all these books about basic New York State CPA, I understand finance. How can you not make profit? I said, what are you guys doing? And he said, James, we're rewarding them for taking up the white space. Okay. Because we don't understand this whole internet thing and we're just going to reward anybody who plays in it. And I see this painstakingly similar approach in this AI. If you just mention AI, if you play in AI, you're going to be rewarded. And let's look back on the dot com era. Other than, you know, price line and eBay, most of them imploded because they didn't have a business model. This is what I kind of see and feel around this whole AI thing. A great term that I learned earlier this week without a human in the loop. You have to be really, really cautious on what it is. You're talking about it at the conference where I said, I'm just waiting to see what's the growth from AI. Because at this moment, I see it's about cost savings. It's about efficiency. It's about speed. But I haven't seen many examples of it. And here's how we're going to grow. You can't cut your way to growth. Oxymoronic. Yeah. Isn't that funny? So just in your observation right now, how does somebody stay relevant in this AI right now? I mean, here, my observation is that everybody is kind of like, almost like a stampede, like a worried stampede. I see that everybody is trying to like learn everything they can about how to use AI. And when you think about a topic that you talk about a lot about future proofing your career, what human skills in this relevance topic, what human skills become more valuable as AI starts to progress? Because Jim Quick, as you got to meet him at that event too, he's launching a genius campaign right now all about human intelligence. So what human skills are more important than ever right now? I think curiosity. I think the willingness to learn. Don't be an ostrich bearing your head in the sand and hope that it just passes you by. Be aware. But they in the middle. This is kind of what some of the problem is with our country where we hang on the fringes of the extremes all the time. I saw an article recently that said IBM had stopped hiring some juniors and then they quickly realized, wait a second, we're not going to have any managers five years from now if all of our entry level work is done by AI. There's going to be nobody to promote, to be a manager. So staying curious, one of those seven leaders that I mentioned to you that left the Sasha Group now, he has done some cracking up the code of AI and it's worked personally for him. He started some smaller businesses using AI as a support. He put himself a diet and a regimen, lost 45 pounds using AI as a tool rather than drugs and things like that. So he's now pivoted and he said, you know what? I know enough basic about AI that I can help the normal Joe. So I'm going to do this 90 day learning program, charge 1500 bucks and just make the average Joe who is an entrepreneur founder, leader of a startup, learn some basic skills on how to apply and utilize AI today in your normal walk of life. So I think that's brilliant. I think that's really smart. You heard me at the conference say the reason why I like the two roles that I'm supporting here in fact totem and vibe is because I think there are going to be people who lose their jobs at AI and then those people will become founders and entrepreneurs and do some interesting thing. Yesterday I'm scrolling through TikTok and there's a professor who said, and by the way, the next round of millionaires are not going to be Silicon Valley guys. It's going to be plumbers and HVAC guys because AI is not going to fix your boiler. You're not going to climb under your deck and fix the pipe. It'll never happen. So those guys are going to be in demand. Yeah. One of my kids is kind of going the route of FBI, you know, and the other kid is probably the real smart one. He is in school to become an electrical engineer. And I said, it sounds like a good idea. I think it's brilliant. And I hear Gary talk about that as well. You know, Gary is always saying like, you want to make a ton of money, become an electrician. You know, I love that. Well, those guys are pretty much started six figures with no college debt. They're way ahead of the game. You're talking like a decade ahead of the game. Here's an interesting question. What is one thing that people may need to unlearn right now if they want to stay relevant in the next decade? I think it's sort of protectionism. You know, I always compare what it was in the hallways of Sachi versus the hallways of VaynerMedia. We were always afraid that somebody was going to take our idea because we were in an environment of fear. Is this the day the client fires us? And then when I got to VaynerMedia, I realized, wait a second, this is an environment of fearlessness. Right. There's nothing that they believe they can't do. And they're willing to collaborate because they're confident in their ability. They're not worried about the next guy taking their idea. They're embracing the enhancement of that idea. So you know, I think you got to release the, I got to protect this. This is me. It's me, me, me. It's my idea. We four no more kind of approach. Is it safe to say that you're a big advocate of people staying in the creative process and coming up with their own ideas? Yeah. I think, well, Gary likes to say you're only one piece of viral content away from fame and fortune, right? Right. So then you're busy around. And if you approach every piece of content with that mind, this could be the piece that changes everything. You know, you're going to put that effort in. And you're going to look for others to help round it out and soften it up. And I always tell people, you know what this is? This is the difference between static and beautiful classical music on the radio. You don't have to take a hammer and smash the radio to change the channel. Sometimes it's just a little tweak. So I spend my day tweaking entrepreneur ideas. Well, these entrepreneurs come to me with an idea. I'm like, I just tried that. You know, I've seen it done that way once before. Maybe look at it that way. Here's an example of how you could do something like that. You might want to talk to that guy over there. He's done that. That's my day. I don't produce decks. I don't make presentations. I tell stories from my life. Yeah. Maybe before you decide to retire, we should create a new platform called like Orsini GPT Orsini GPT. I did decide to retire and now I'm not retired. Well, I mean, I mean, when you actually really decide to retire, you know, I'm the same way. I want to talk a little bit more about future proofing, but first it's funny. You made me think of this. I had a, I'm getting pitched on stuff all the time and the pitch unbeknownst to them because, you know, if you're just pitching and not getting pitched, you don't understand how similar your pitch is to everyone else's, which I find humorous. So I always accept pitches. I'm like, sure, let me hear about it. You know, this guy was telling me about this really cool platform, but it has nothing to do with what I'm doing right now. And it's, it wasn't interesting to me. I thought it was cool, but he was basically saying, you know, like, if you don't take advantage of this right now, which, you know, it's like a big commitment to do all that stuff, it's going to pass you by. And I said to him, I go, that sounds kind of nice. If that passes me by. So, um, what do you have to say to people that are frightened? You met John Lee. John Lee is, you know, entrenched in AI. And that's all he does is he's teaching AI and I'm friends with him. And he, every single week he goes, all right, forget everything I said, everything's changed again. Everything's changed again. So what do you, what do you have to say to that person that has that like fear of missing out or they're trying to catch up with something that's, they're never going to catch up with it. I say, embrace the fundamentals to achieve success. All right. So, so there are just some basic fundamentals. What do I mean by that? I think anybody can grow a company that's not profitable. I think it's a real unique skill to grow a profitable company. Right. I often say, there's a difference between swelling and growing. Both get your big one is healthy and one is not. Wow. Right. So, so I spend a lot of time on basic blocking, tackling and telling people, let's figure out a plan to grow healthy. When I ran the Sasha group, okay, we were a little under 10 million a year, one, 12 and a half and year, two, 15 and a half a year, three, 17 and a half a year, four, 20 and a half and year, five, never dip below a double digit profit margin in a year, including COVID. That is healthy, profitable growth. Now, that's not explosive growth, okay, which some carries companies do. They have explosive growth, right? From 40 to 350 million, that's explosive growth. Some years more profitable than others. It's just a different style for me. I only know how to grow profitable companies. Right. When I was the CEO of a small publicly traded mobile media company, I got the company to cash flow break even a year and a half ahead of schedule. A new board came in and they said, James, you run this company like a general motors. Okay. We want explosive growth, no profits. I said, I don't know how to do that. I could only run a profitable company. Let me help you find the next CEO. And that's kind of what we did. We parted ways, you know, like I said, I had a three year contract. I said three and a half years. You know, I don't know how to run a company. It's not profitable because I embrace the fundamentals to achieve success. I'm not chasing a shiny object or a star. By the way, that company won't bankrupt several years later after two CEOs, three chairmen to the board and two CFOs. Not that I'm anybody's savior. It's not about that. It's just careful what you wish for. You know, it's so funny. I guess I'm the minority, but explosive growth doesn't get me all hot and heavy. You know, I love the idea of profitable. I mean, our family is focused on family. And, you know, that's one of the things that I got a lot when I was having a talk with Gary about, you know, we were just talking about our family. We weren't talking about business and stuff like that. His favorite topic, by the way. Oh, for sure. I picked that I picked up on that right away because I asked him a question about like kids and and technology and he got all fired up about it. But this idea of explosive growth, it doesn't get me excited. I love profitable and I love I love a good living. But what is going on where I see in business, especially in the young generation, if you don't have explosive growth and you don't become a billionaire, you know, threatening trillionaire, it's like you're a failure. You know, it seems like some sort of a trap. Well, look, you know, so Gary wrote the wrote a book called 12 and a half about the soft skills of leadership and patience is one of those characteristics that he highlights the there's really 13 he calls it 12 and a half because he hasn't mastered the kind candor side of it. But patience is really important and we're in a society that is impatient. And I sometimes see that, you know, even with myself, you know, I'm hitting buttons three and four times, you know, standing around waiting for an elevator, right? Like, of course, somebody hit the button. That's why we're here. Then somebody else is going to come up and I got the magic finger. Let me hit that button. Yeah, hit it again. You know, faster, right? So, but patience is learned. It is a skill. I've had many times people like James, you're not sensing the urgency. I said, I understand the urgency. I said, I'm just not my hair on fire like everybody else in the room. Somebody's got to stay calm and get us through what the situation is, right? The thoughtful plan to get us to the other side. So patience is really, really important. And somebody youth don't have it. You know, so my wife and I are trying to be a good, a godly example to our three now grown children. One already married with a baby on the way, one getting married in August. You know, one living in Manhattan tearing it up in the city. I mean, we're just still trying to walk a walk of example because they will gather more from what they see than my words. Right. So I need to demonstrate what it is I'm saying to them. Yeah. Right. And as I'm working with these entrepreneurs, it's the same thing. I am sharing from my experiences. Okay. Don't, don't do what I did here. Here's, here's a mistake that I made. You could avoid that. Okay. You don't need to go down that path. And by virtue of avoiding a mistake, you're going to pick up speed anyway. Right. This is what Gary hired me. He said, James, you've made 25 years of mistakes that I don't want to make. Help me avoid the potholes and move faster. Genius. Yeah. It was, it was great. One, he was brilliant for hiring somebody like me when he did. I was a big investment at the time, but it was a retailer trying to become an ad guy. He's not the voice of an advertising industry kudos to him, but it was also, you know, at the very first meeting, very first meeting, he introduced me to his 400 plus people and I said, I'm here to help keep the trains on the rail. He said, hold on, hold on. No, time out. Time out. You're here to help me hover above the rails like the trains in Japan to move faster, recalibrate everything right there in a second. And then I understood, okay, this is, this is my role. Yeah. It's all about speed for him and we'll have to, we'll have to leverage my experiences to bring him speed. I know that you're involved with, you know, factotum and vibe right now. And I want to hear more about those, but kind of in the same sense, what kind of scenarios and projects get you excited? You know, I find it fascinating that you're a guy that can come in and help write the ship of somebody that is like completely stuck and thinks that there, things are not going the right way. What is it about that scenario where you come in and, and fix things? Is it, is it's always been like a superpower of yours and how is that got you reignited after retirement here to engage in factotum and vibe? You know, well, I think it's, uh, I enjoy, uh, helping others actualize their vision. Right. So, um, you know, when I was the CEO of, of that, uh, CEDO mobile, it was a hard and lonely job at number one. Uh, and then I read a book consigliari, ruling from the shadows by a guy by the name of Richard Heider, and it was about being a great number two. I was like, wait a second, that's kind of, that's who I am. In fact, if I had somebody like me, when I was a number one, I'd be hugely successful. I didn't, I had a number two who wanted to be a number one. So, you know, that's, that's a difference. Um, so, you know, for Gary, it was, can you describe what you're doing a single sentence? I said, yeah, I take dreams and visions and tournament to action plans. He's like, great, you're hired. I got a lot of dreams and visions. You know, I'm partnering both with Bobby Lane, I'm fact totem and Andrea Sullivan on the vibe. Two amazing human beings, by the way. Yeah. And they are both leaders that I'm helping actualize their visions. You know, the whole vibe initiative was really birthed during COVID when Andrea was stir crazy and was taking a fortune 500 female executives to far away places like Bali and Costa Rica, just to have human interaction because we were all locked down in our homes. So she was traveling to places where COVID wasn't as, uh, as prevalent and then they were doing good things and serving communities, but also learning. That was the gist of Vive and Gary Sutter. And he's like, James, I think there's a commercial business model on what she's doing there. She's doing it for fun, but check it out and let's see if we can make it a real business. And then I did, you know, it's a combination of his vision to make it a business and her vision to, you know, do this thing for people. And in that particular case, we wrote a business plan in January. We programmed it in February and March. We sold into it in March and April. We launched the first class in May. We did a million dollars in the first year. So that was really cool. Uh, Bobby came to me, uh, and you know, in both those situations, I worked both Bobby and the past. I'm Andre in the past. Bobby came to me with this idea probably 15 years ago. And I was like, you know, not really cooked up yet. Uh, not right for me, but you know, swing, swing back when you got a little something, a little more meat on the bone. And then over the last six years, he's really plowed efforts into it. And, uh, and he had, uh, uh, some successful case studies in the UK. And he's like, what do you think? And I said, you know what? Now there's clay on the wheel. I think I could help. What do you want? A vase, a cup, a dish? Cause you know, I do want me mold this. And he's like, look, I'm looking to you grew, you grew Sasha to 20 million in five years. Can you help me get fact totem to 30 million in three years? If I give you a 10 million head start. So that's my role. That's what I'm trying to do now and helping them stand up the US operation to what is a very successful UK operation. How does James or Cini view failure? Cause you get involved in these things and it's like very exciting. And you know, you obviously don't get involved in something and you don't, you don't think it's got clay on the wheels and all that stuff. But there is that possibility of the unknown. What's your thought on that? Yeah, my thoughts are fail, fast, fix, fast, learn fast. Right. So if I can just kind of, kind of do that, uh, I'm really, I'm not afraid to fail. I have enough success now after 40 years that I'm not really proving anything to anybody else. That's, that's the beauty of where I sit right now in my career. It's hard for my wife to understand too, cause I got a little shoulders back, kind of moxie, uh, like, you know, if it ended today, um, I'm like real good. You know, like it's, uh, it's people like you who want to talk to me and hear about it. Um, you know, I think today you are my 75th podcast that I've now done. So that's a busy day. No, no, not just today. And in total, but it's, uh, uh, you know, so I fail less because I look at some of the things that I have done in the past where, you know, I think I shared the story where how Bobby and I met was it was a failure that I was a young global CFO and I bought three companies in London and I merged them together. And I didn't pay any attention to culture and it was a dumpster fire when I was done and that's how Bobby came. I'm like, look, you're going to help me fix this. I need somebody on the ground who can unravel the mistake that I've made. So, uh, you know, it's not all success stories. It's, it sounds great in a one page bio, but yeah, there were definitely bumps in the road. So if I want to get Bobby's attention as a potential partner, I should just fail. And he'll be impressed by it or something like that. Well, you know, we have a lot of folks that are failing that are hiring in fact, told him right now. So, uh, hey, the failure is a big business. So I like to keep my finger on the pulse of what some of the giants are doing. And, you know, through some pretty good resources, there's some very big companies that operate that have traditionally operated on a massive scale in the live event and, you know, they have big organizations that are about to completely fire everybody and just like replace them with like two like agents. You know, there's this whole agentic AI thing. So this is happening like everywhere. And then there's also startups that are just not even hiring people and having AI agents, you know, do the work. What are your thoughts on that? And is there an implosion ahead there? I think it's a mistake. I think one of the things that we were talking about recently is this switch to analog from digital, right? A return, a return to analog, a return to phones down. You know, Gary owns restaurants, right? Yeah, it was at the fish one. It was a five fish club. Right. So we're actually a little maven this week. He wants his next club to have lockers. So when you're walking, you got to lock up your phone, right? In order to enter the restaurant. So we're seeing a lot of that. I just came back from a client of mine in Maryland who ran a conference. This is a 30 year doing it. 700 people. It's for automotive dealership guys and everything. People are starving for human interaction. Apollo, the big hedge fund company, your last two investments were more purchasing big events. Come. So I don't think live events, concerts, anything like that are going anywhere, anytime fast. OK. I just, you know, a couple of years ago, I voted the Ares tour with my daughters and my wife for Taylor Swift. It was actually cheaper for me to fly to four of us to London by the tickets at Wembley Stadium than here in the States. So live human interaction is big. We're going to swing back this pendulum to that. I run a family at home at the Jersey Shore for two weeks every summer. And my kids can't wait to be a part of just this board game, porno hole, toss, beach life for two weeks straight. I think anybody who just is building a world that is solely digital is really missing out on some stuff. And I think there is going to be a return to back back to basics and having a blend. You know, I mean, still leveraging attack, but but having this blend of it's an and and rather than an and. One of the funny observations that I have about the advancements of AI is that people are feverishly trying to get AI to be so good that it looks real. It's like, why don't you just be real? You know, it's like almost like real human interaction and interface and also social media. Probably one of the reasons Gary's been so successful with that is that it's just raw and real. It's not fancy and everything like that. So let's talk a little bit about this future proofing concept, because I think a lot of people are mesmerized by this idea of just taking risks and going for it and everything. And I don't see a lot of people and there's poor parenting probably in there as well. But I don't see a lot of people like doing any like planning. You know, they're just like all in and they're just going to like go for it. What industries or career paths do you think are most vulnerable right now because the world simply doesn't need them anymore in any way, shape or form? I think research, paralegal, you know, those entry level positions in service sector companies that spend their day looking through files and researching. That stuff is going to be a real problem, you know, because they could do it quicker. Now, can't do it just machine, have to have human in the loop. Somebody's got to still look at that. But, you know, that's not an entry level who's looking at it. That's a little level up, right? So but I think that's the danger. Anything that was there, grinding, if you will. OK, and coming up with the legal brief that now you're going to, you know, you're looking back on previous legal cases for historical data that that's all being done through machine now. And then it's fairly accurate. I give it 80 percent, not 100 percent, but it's fairly accurate. So if somebody just has a human in the loop for 20 percent of the time, that's that's going to be that's going to be important. Yeah, if you ever catch some of the old movies, you know, like the Tom Cruise movies with the lawyers spinning like the entire night reading all the law books and stuff, exactly those guys are out. They're followed with three guys carrying all the binders as they walk into the room. Right. There's one lawyer arguing the case and there's three dudes behind them and did all the research behind it. That stuff, you should be worried about that. Those guys need to find something else. So if somebody wanted to future proof themselves now, it's going to be a lot of people listening. You know, I always want to make sure that people kind of like know what to do. If somebody wanted to start today, future proofing themselves, where would you recommend that they place their focus? I think they they should have a side hustle around their passion. OK, so the days of dedicated to I'm just a robotic for the corporate man. I forget about what I like to do. OK, I like to bake. I like to, you know, do trading cards or whatever. I think you should simultaneously be running the side hustle because if and when your passion becomes your profession, it is lights out. Right. You you've already won, you know, when you're smiling every day, when you're whistling every day that you're that you're doing this. So I believe this gig economy of side hustle is is really important and leads to some hugely, hugely successful businesses that were outside of, you know, what you thought your profession was. So big big proponent of that. Yeah. Well, that's what the dragon is doing as you are looking at him right now. You know, I mean, I I left some very, very lucrative businesses to start a podcast and everybody said you're out of your mind. And it took me eight years, but, you know, I'm having a ball now. And I'm also playing the guitar. Yeah, look, it's not the first time I've heard out of your mind, right? When I left Goldman in the 80s to go to work for a single public relations firm in New York City called Rowland that nobody had ever heard of. They were like, you're crazy. Who's leaving Goldman Sachs in the 80s? Everybody's trying to drive there. You're leaving it. Yeah. But within five years, we built the fifth largest public relations firm in the world. And I was a global CFO overseeing 31 offices in 26 countries by the time I was 30. So didn't look foolish in the rear of your mirror, looked foolish at that moment. But I knew I didn't like what I was doing anyway. I was making money, but I really was not enjoying my role in Wall Street. I quickly recognized like this is not for me. And if I don't leave pretty soon, I'm going to make too much money where I can't leave. So, you know, it was it took a shot. So I think there's more people taking shots now. And by the way, if you could do it with the air cover of I got a full time job that's paying me and giving me benefits, everything, I'm going to do this thing. After hours, I would wake up early in the morning. I'm going to, you know, a lot of people making a lot of money on collectibles and trading cards and stuff like that. I don't do that personally because it's not what I like to do. But there are enormous businesses around that, you know, just flipping stuff. You know, this whole world of live shopping now, you know, can really put anybody in the mix of a moving product. And it's easy to put up a Shopify site or direct a consumer. The fulfillment gets a little harder because obviously you've got a lot of stuff in your basement boxes and stuff like that. But but generally speaking, I had a niece who, you know, recognized she was selling medical products and then realizing the operating room. When they opened the package, they throw away the tools. And she's like, wait a second, I'm going to collect those tools. And I'm going to sell that to morgues and veterinarians who don't care that it was an unused tool. Right. I mean, that's a whole side hustle in front of another business because she just recognized like, put all this waste, I can do something with that waste. It's funny when I'm at a place now when people say, what are you out of your mind? And I go, oh, well, thank you so much for noticing. I appreciate the compliment. And they go compliment. I've been trying to get out of my mind my whole life. It's gotten me nothing but, you know, trouble. Here's an interesting one. What skills do you believe will never go out of style, no matter what? No matter how advanced technology gets, you know, I want to empower somebody listening right now and just what are some human skills that will just never be replaced? Well, we talked about certainly we talked about the trade industry. Right. So so the plumbing, the electrician, the other stuff, I don't think that'll ever be a fully automated at a box. But I think understanding finance has made me a hugely successful businessman, OK, because I never had to walk into a situation blindly and rely on somebody else to tell me what this means. You know, my wife has a whole profession of helping to educate and bring financial literacy to female founders and business owners. OK, who started business, but, you know, we don't know how to balance a checkbook or anything like that. I think it's a big flaw in our colleges and universities and high schools, even that you're not teaching somebody basic budgeting skills. No, we all have a checking account where you've got to have a balanced budget. You know, I shared that even with my children, like, look, you've got to have some kind of basic understanding. You're not all accounts. I get it. But, you know, you have to understand money, the power of it, the fear of loss and how to just, you know, know that the pluses need to be greater than the negatives or you're in trouble. So, you know, a big, big proponent of that. Even Gary talks about, you know, there are certain things you have to go to school for, right? Medical accounting, legal, you know. But, you know, if you're going to be a major of African-American studies or something like that, you know, maybe maybe you don't need to have three hundred thousand dollars worth of debt. He laughs at those that are majoring in entrepreneurialism. He said, we just got to work. Like, why? I mean, to be an entrepreneur. If you're an entrepreneur, you know it. I had a very famous speech at Columbia where, or now it was USC, I think it was, or where he said, who here is an entrepreneur? And the people raised their hand. He's like, all right, get out of here. Go be an entrepreneur. Why are you listening to me? You're in the wrong place. Oh, that's great. That's genius. That's, this is, this is also funny. And I'm just thinking that probably anybody could probably just call up anybody that's in an Orsini, even if it's one of your kids and just get some financial advisement, you know, just thinking about them growing up in your family. I mean, they got to know more than most people. Well, look, you got to know enough to realize I don't do my own taxes. I have my own, you know, financial and wealth advisor. Like, I know my lane too. I don't try to be everything to everything. Well, but you have a basic understanding, though. Yeah, I have an understanding enough to realize that I'm not going to be current on tax loss. Right. So I better, I better go to somebody who's, who's paying attention to everything that's changing because 2026 is different than 2025. You know what I mean? So even those kind of things, you know, doctors are specialists, right? So there's specialists in the finance field as well. Yeah, that was a golden cage. That being a doctor was, I mean, there was, there was a lot of good stuff to it. But I was so happy to free myself up from that. I want to talk a little bit about identity. You know, I just talk to people all the time about it's like they know what to do, but they got to get out of their own way. So one of the things that I've noticed is that people often kind of become trapped by the version of themselves that created their previous success in this fast changing world. Have you seen that? Have you seen people? You know, I mean, like the story that comes to mind is the whole, you know, Blackberry concept, you know, it seems like you got to be agile now. You can't be caught up in who you think you are based on who you were. You know, how important is it for people to be? I think you said it before, open and curious and agile. Yeah, I think it is important. I think the whole concept of personal brand is important, right? And what does your personal brand stand for? And and can it stand on its own? You know, I have when I write an article, I actually have some people thanking me for for writing the article myself because they realize it's not AI. That's me talking, right? So that's when you when you have a personal brand where people actually recognize that really, you know, really important in in standing that standing that up. And there's times where both now and in fact, I'm here in the United States and in the past with CEDA mobile, where in the early stages, my personal brand was bigger than the company brand. And they had to have to lean on my personal brand first to help stand things up. And then the company brand takes over. But, you know, look, I'm a big consistency. I'm the same guy, you know, on the call with you here that I am with my clients, that I am with my family, that I am at my church, that I am in my philanthropic endeavors. That's how I've managed my world by not having to change out and wear these different masks from time to time. But to what you see is what you get. And I think that was the beauty of Gary, because people ask me, what is he like? And I'm like, what is he like? You're seeing him on. He's exactly like what you see on video. That's that's who he is. Right. The fact that you quickly realize family was important to him. That should be a surprise to anybody. OK, that's the most important thing that he has, you know, and that was our kindred spirit. We are total opposites. I mean, you never total opposites. Right. I would joke and say I wear a ski helmet going down the bunny hill at Shawnee and he jumps out of helicopters, you know, to totally different people. But mutual respect for what it is that we do. Family, very important principles, very important kindness, important, helping others, important. You know, so those were all the things that aligned for us. So funny, you just reminded me I was at a comic con with my son, who's a freak for that stuff. And we're just walking, walking around. And, you know, I see over at I think it was a V Friends booth or something like that. But Gary's there and there's like, you know, there's like at least 150 people online to like, I don't know, shake his hand and get an autograph or something like that. And we were just walking by and I had met him a couple of times. But I didn't like know if he like knew me, but we were just walking by. And I'm with my son. It's like perfect timing that what Gary did. He goes, he goes, dragon. And I turn around and I'm like, and I walk up and I shake his hand and my son meets him. And my son goes, we walk away. He goes, you fucking know, Gary V. And I said to him, I go, apparently, apparently, you know, he's got a great memory. You remember great, great politician. I'm horrible with names like that. But, you know, he's like a politician who remembers everything. Similar story, a friend of mine was wearing a jet hat at Comic Con. And Gary's like, you know, Jets. And he goes, Gary, where's James Orsini? And Gary goes, he's back at the office doing work while I'm here. It was so, it was so funny because the guy's like, I can't believe like he actually had a little dialogue with me, guys. That's the funny thing about success is that, you know, the world starts to perceive that you're different, you know, and sometimes I guess people get caught up in that. I hear him speak about this and I've heard you speak about it too. But just as kind of somebody that really has their finger on the pulse, you're still in the game. What advice do you have to give someone that is looking to reinvent themselves at like 40, 50 and 60? Because I very often meet people that I perceive, you know, in those age groups, they have a lot of wisdom and experience. I think they're highly capable of doing some big, big things. But they kind of have this impression that they've missed the boat and that, you know, what do you have to say to those people? So with those people, I say that they should do what I call an SSP matrix, a strength, skills and passions matrix. These are my strengths. These are my skills. These are my passions. Forget about your resume and what you've done in the past. Okay. I'm going to give you my wife as an example. So she was a big corporate, you know, finance and international director of financial reporting, like big stuff and big corporations. And then she, she sort of that ended and wanted to want it to end. And I said, what do you want to do? She goes, I want to help. I want to help female entrepreneurs with financial literacy. And I said, that's fabulous. I said, I know somebody who owns a bookkeeping firm down in Florida. And most of her clients are female business owners. So I said, let me call her to see if she's willing to meet you. She's not looking for somebody like you, just so you know. But when you tell her about your strengths, your skills and your passions, she doesn't have somebody like you in her 12 person company. And they got to talking and they hit it off. And my wife loves her life now. Now she's making, you know, one 25% of what she used to make, but it wasn't about the money. It wasn't about it. It was about smiling when you're doing this task and helping people, you know, helping people find their way. So she's now the sort of video overlay that explains the financials to a bookkeeping firm that was just turning over books and records. So now there's an interpreter of, hey, what are these things actually telling me? You know, and I'm just watching the change in her. I mean, you know, she's glowing at doing this thing that aligns with her strength. All right. So she has a strength in that she's a female wants to be dialogue with other female. She's got a skill in accounting and she has a passion for helping other people when you married it up. Sounds nice. I always tell my kids, I mean, like, you know, my kids do great. They play sports in there. I'm totally fine with them playing Fortnite at night. But I always say to them, I'm like, you really love those games, don't you? And they're like, oh, man, it's so great. I'm like, well, why don't you get involved in that business? And they're like, I don't know, you know, I'm going to go do something that sucks. What do you think the future of leadership looks like? A lot more in kindness, a lot less rigid, a lot more flexibility, COVID proves that we don't have to all be in the office 24 seven. Okay. So, you know, recognizing and meeting people where they're at. I think I think the hybrid blend is going to be the best, not not fully remote, nor fully in the office, but I like the hybrid blend. You know, it's more in the middle. It's what Gary calls purple. Okay. More life in the middle, less on the extremes. You know, come come back, come back to the middle and have have a much better, much better lifestyle. Is my dragonfly NFT going to be worth money one day? Come here, mount the gods of years. I got a couple of B-francs as well. I'm there on the consistent cougar as you would, you would picture that as my right personal brand. Perfect. If I was going to own one, would you picture me with a consistent cougar? Because it is who I am. Yeah. Well, I could care less if it, if it makes money. I love it. I just looking at it. All right. So what I want to do now is I want to do a couple of rapid fire questions because we're at the end. You do your best. Biggest mistake people make during change? Lack of patience, expecting it to happen too fast. Hmm. There's that patience thing again. How about this one? Most overrated business trend? I would say, I've got to be a millionaire by my 20s or 30s. One thing AI will never replace plumbers. Blumbers. From a family of plumbers. Plumbers and electricians. My grand, my grandfather was a plumber. My father was a plumber. My brother was a plumber. Most underrated human skill? Kindness. Yeah. It's just be nice, man. One thing people should stop doing immediately. Chasing the shiny object. Yeah. I love that. These are good. You're good at this. Definition of relevance in 2026. I think it would be an awareness of your surroundings. What's what's happening around you and how might it affect you in some way? What scares you the most right now about the future? To tell you the truth, I don't fear the future. I embrace the future and there's not much I fear. And what are you excited about most about the future right now? Oh, for me, being a granddad, coming down the pipe here and, you know, I don't know what that entails, but I'm excited about it. And I hope I hope I live up to the title. Well, I think everybody is going to be a little bit wiser. And a lot of people are going to probably figure out that some change might be on the horizon for them in a positive way. And now people know that you're actually a pretty cool guy that has his shit together. So that's pretty cool. You know, thanks so much for being here. If people want to step into your ecosystem, what's the best way to do that? Yeah, I am James Orsini on LinkedIn and Instagram at Jimmy DePencil on X and TikTok. That's great. And I will say that James is like a very, very nice, friendly person on social media. Like if he shares your stuff and things like that, he's wonderful. I shouldn't say that to everybody, but thank you so much for being here. I just really enjoy, you know, you're the kind of person that I would love to talk to you for a lot longer, but, you know, I'm sure that we're going to cross paths over and over again, and I'm excited to see what happens with factotum and vibe. And, you know, and I'm not going to even try to make a prediction of when you're going to retire. Thanks, JC. Appreciate it. I hope your audience enjoyed it. Hi, this is James Orsini and this podcast makes sense. That's it for today. To support the Make Sense with Dr. JC podcast, be sure to subscribe, like and share, as well as follow the Make Sense sub stack for free daily quotes, live streams and blogs. And remember, learning without action is just another form of distraction. If something hit home and you learn something today, give it away. That's the only way it's going to stay. See you next time. Makes sense. If you liked the show, please take a moment to rate, review and subscribe. It really does help the show to grow. Thank you for listening.