March 11, 2026

Why AI Will Never Replace Human Connection in Sales with James Stephen-Usypchuk.

Why AI Will Never Replace Human Connection in Sales with James Stephen-Usypchuk.

James Stephan-Usypchuk brings 15 years of AI development experience and a psychology degree to a conversation about what machines can and can't replace in sales. We explore why trust still requires a human face, how predictive algorithms should be used as filters rather than closers, and why likability remains the ultimate competitive advantage in an AI-saturated market. James shares real examples from his work with private equity firms, including how his team uses AI to identify acquisition targets—but always injects the human element when it's time to have a real conversation.

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James Stephan-Usypchuk has been building predictive AI systems for 15 years—long before ChatGPT made it mainstream. He's a cancer survivor, serial entrepreneur, and someone who's worked with BlackRock, Blackstone, and private equity firms on deal origination. And he has a psychology degree, which gives him a different lens on the AI hype than most technologists.

In this episode, we dig into the real question organizations are asking right now: AI can do almost anything, but what should it actually do? James makes a sharp distinction between tasks that can be automated and the human elements that can't—and shouldn't—be replaced.

What we cover:

  • Why 82% of AI implementations fail when built on bad data
  • The difference between using AI as a "magnet in the ocean" versus having it "make sushi on the back of a boat"
  • How predictive algorithms can identify who's likely to sell their business—but can't close the deal
  • The stat that should scare every marketer: 15,000+ ad impressions per day, but only 3 seconds of recall
  • Why the best salespeople he knows are comedians
  • What happens when a sales rep is pre-sold and the rep still runs the script

Key insight: "AI can do everything, but so can 50 million other people using AI. When a human steps up with a likability factor you've never seen—automate that. You can't."

Connect with James:

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Transcript

Lee Levitt: Welcome back to the Thoughts on Selling podcast. Today it is my absolute pleasure to have James Stephan-Usypchuk joining me. We practiced that last name, James. Welcome aboard.

The first question, aside from how to pronounce your name, is: Who is James?

James Stephan-Usypchuk: I can say that I'm a man of many hats and many backgrounds. I'm a cancer survivor. I'm a philanthropist. I'm a family man. And I suffer from the chronic illness of serial entrepreneurship. As everybody knows, if you're an entrepreneur of any kind, you love abuse or else you wouldn't keep doing it.

I've run marketing agencies. I've run large companies. I've run groups in M&A. I've worked with independent sponsors. I've worked with groups like BlackRock, Blackstone, originating deals for them, working on mandates—everything far and few between. But most importantly, my expertise comes from a psychology degree and focusing on developing artificial intelligence way before OpenAI was a thing. This is talking about 15 years ago.

So it's kept me busy. I would say it's kept me sane, but it's also given me a very unique perspective into the world of where things are going—I would say two or three years before we actually get to the destination. So I guess that makes me a futurist.

Lee Levitt: It does. So the conversations we've been having have been focusing on the intersection of capability—technical capability—and what we can do today with a ChatGPT prompt, or a Gemini prompt, or a Claude prompt, or some interplay of all of those. The information that agent can find, information we can provide, put into it—the possibilities are amazing.

And a question I asked you was not from the individual, not from a salesperson sitting at their desk looking to improve their email. What is today? Organizationally, managers and leaders are looking at technology capabilities with a full stack already, saying: If we're gonna add something, what do we take away? And then two years from now, we know it's gonna be dramatically different.

James Stephan-Usypchuk: It's interesting. I think we are right now in a market where everybody is scrambling to catch up. And I think it's a race that very few will actually end up crossing the finish line with.

What I mean by that is—especially when you look at M&A—there is this obsession of, "Well, we need to integrate artificial intelligence into what we're doing." But then you see a salon saying that, and you're like, "What are we talking about here? How is AI going to run your hair dryer?"

So I think there's a critical thing that needs to be a little bit more enforced when we're looking at the application of AI. But that being said, there is a real world where AI is enhancing—and in some instances, replacing—jobs, queries, functions of a business where it's causing some real upside.

I recently met a gentleman who we were connected through an AI platform called Boardy—that's B-O-A-R-D-Y. What they do is this little bot built a massive network. I say "he" as if it's a person. It built a massive network, and from there is just a massive super connector. You tell it what you want and then it will connect you with people.

So it connected me with this gentleman who had an AI firm, a bunch of engineers. It turns out what they do is very synergistic to what I do. They work with private equity to effectively solve a pain point, error, or problem, leveraging AI to generate return on investment—lift on the balance sheet.

So say I'm a car parts company. I have inbound calls. I can't handle them because I need to work on the car. They created a solution to solve that, which increased revenue. That's a real problem that they identified, prescribed, and then built a solution for.

That is where AI is going—very quickly. Especially from a banking and private equity space, there are funds that I work with who have told me, "We need to figure out an AI thesis for our portfolios. We need to figure out how do we integrate and get up to speed."

But one of the things I've been challenging everybody with is: speed is relative. There is something to be said for doing it for the sake of doing it versus doing it properly. AI can automate just about anything. It can do just about anything. But if it's not on the foundations of good data, you might as well set your money ablaze.

So for me, the future of AI is: everybody has access to it, but the application and execution is poor. We're having to quickly find those subject matter experts that can fix that or that can somehow architecture a solution that makes sense and makes them relevant.

But that being said, whether it's marketing or sales, the fundamentals of the human condition are and have always been the same since we started advertising. The only difference is how much noise there is in the ocean.

And right now, like you and I were talking about, we need to be very cognizant of how much we're producing in terms of noise and digital pollutants. But at the same time, how are we able to still maintain that authenticity with the customer?

Because at the end of the day, whether AI is doing 100% of the work or 10% of the work, the trust factor between human to human is still gonna be what champions everything. And I would argue that the more that is automated, the fewer staff you might have, but you still need that one-to-one relationship, which cannot be automated.

Unfortunately—and I'm in the business of creating relationships for a living—I use AI and predictive algorithms to go out, identify groups that are looking to sell their business, or groups that want a certain product or have a certain pain point, and originate that opportunity. But we always inject the human element when it's ready to have a conversation.

So you use it like a magnet in the ocean to collect all the fish and the type of fish you want, but you don't have it process the fish and start making sushi on the back of a boat. We still have to do a lot of that because there's just not that level of trust.

Maybe we get there one day for certain elements, but I think it's part of the beauty of business—that two humans are doing a podcast, or buying a product, or solving a solution. And I think it goes beyond commerce. I think it goes to where we need to interact with each other.

Lee Levitt: So James, your undergraduate major was in psychology, right?

James Stephan-Usypchuk: Yeah.

Lee Levitt: Someone with an undergraduate major in computer science might say, "Oh, we can code that in. We can code in trust building. Our agent will build trust with their agent and they'll get to some level of mutual high-level machine trust. Your bits are clean, my bits are clean. Let's do business."

James Stephan-Usypchuk: I would argue that no matter how clean the bits are, very seldom—or I would say even a rarity—do you see the person writing the check completely automate that process.

There is a level of control and contingencies that are around any kind of financial decision, no matter how everything checks out. The report could be AAA, but those things could be fabricated too. If systems can be taught on how to ingest things, then that means that what they're ingesting could also be doctored, manipulated. It could cause them to hallucinate. It could cause them to give false information.

It'll critically think within the box that it has. Even with agentic AI, even with all these different elements that are being developed, you look at the human part of any running business—unless the business is 100% humanless—that process will always still need a person to pull the trigger.

Which comes back to: they need confidence. And I can guarantee you one thing. Let's say they go through all of that and they pull the trigger on something that no human ever did a vetting on. It takes one person to be wrong for millions of dollars to go down the drain, and the trust behind the system erodes very quickly.

Lee Levitt: You know, I don't usually find myself playing devil's advocate on behalf of our little electronic friends, but fully autonomous driving is far safer than letting most of those lunatics out on the road.

James Stephan-Usypchuk: I definitely think there's an argument for autonomous driving. But at the same time, there's anxiety for people that are using those platforms. I mean, I've seen people that are in the self-driving cars—Waymo or something—and they're saying, "This thing is bumping into cars, doing collision warnings every two seconds."

I think at the end of the day there are some things that have a function, but I would argue that those functions replace very mundane or almost non-essential type of work-related things that we do. These are quality of life improvements.

But when we're talking massive, life-changing decision-making—I'll use M&A as an example—that are talking tens of millions of dollars that move markets, I don't think the gravitas of that equates to the self-driving car.

Lee Levitt: Yeah, I mean, you're quite right. Autonomous driving is designed to replace the task of guiding a 4,000-pound object on a boring journey. And by the way, as a driver, I don't see driving as a boring task. I see it as the journey.

I had a Jaguar SVR for quite a while, and let me tell you, if you told me I was gonna automate my 600-horsepower car and lose all the fun out of it, I would've been like, "Well, I wouldn't have paid for it then." It removes the enjoyment.

James Stephan-Usypchuk: I actually have a Genesis now and I love it, but I look for driving to be as much of a function as it is an experience. I enjoy that a lot of our companies work really hard to give you a positive buying experience, a positive driving experience. Hell, my car will massage my butt for 10 minutes if I drive more than 30 on the road. Or it'll scan my eyes and start playing music in different ways.

But all of that for me is part of the experience. This is fun. And it adds to and enhances the human experience because we're all here for experiences. But at the same time, I still think it comes on the precipice of maintaining authenticity while enhancing your overall enjoyment of the product.

Lee Levitt: So I can't overstate the message you're delivering. What you're stating is that when important decisions are being made, trust is what causes that decision process to complete.

If I'm a buyer—if I'm buying a business or if I'm acquiring a major new technology capability—what I'm looking for is not the information that says this thing works. It's the comfort factor in looking into the eyes of the person sitting across the table from me saying, "I've worked with 35 companies like yours before. Here's what goes well, here are the challenges you're gonna have, and here's how we're gonna help you get across the finish line."

And by the way, the finish line for the salesperson is not the finish line for the customer. When the deal is inked, that's when the customer starts doing the work. It's like buying a car. When you go to the dealership to buy a car, your experience really starts when they hand you the keys. It doesn't end when the test drive is over. It starts when they hand you the keys.

James Stephan-Usypchuk: That's right. Not only that, but I would argue when you're looking at people going through an experience with AI or an experience with any kind of product or financial decision, the authenticity at the end of the day is what ends up cutting the noise of what we're seeing and what we're exposed to.

So if we think AI can do everything—yeah, it definitely can—but so can 50 million other people who are using AI. But when a human is able to step up and be like, "Oh, this guy has got a likability factor I've never seen. I don't care what his tech does. I wanna work with him." Automate that.

Because that is where you will struggle, and that is where that human connection is hard to make.

Now, I will argue companies are coming up with AI-generated avatars that look and sound like people. I've even experimented with voice agentic agents and stuff like that. But there's ethics around how to use this type of technology, and there are disclosures that need to be made when you're talking to an AI agent.

And I will say that a lot of people who look at these opportunities get excited at the thought of replacing someone. But when you have to follow the disclosures of "you're using an AI," you completely disarm its actual use—where it was supposed to replace the human condition and create this authentic piece. But by immediately having to disclose it—or else you're tricking the client, lying to them, and effectively causing harm, which you should never do—you're undoing whatever magic you think you were harnessing to begin with.

I see it a lot in cold email and cold outreach, and it's the biggest fallacy out there.

Lee Levitt: You know, this conversation reminds me of the conversation I had with Garth Fasano, who is the founder and CEO of Rainmaker, which is an agentic AI inside sales organization. And his initial target is the small business person who doesn't wanna be awake at three o'clock in the morning to take a call from someone whose pipes burst and needs to schedule a plumber. That plumber needs their sleep.

James Stephan-Usypchuk: But that's okay. That replaces an otherwise mundane function. You don't need authenticity to book that. But you do need authenticity when you're convincing people they need to buy something—you're solving a pain point that they haven't figured out how to plug a product or solution and remedy.

But when you're looking at the overall finance landscape and you're saying, "Well, where are we gonna be in a couple years, and what do we do with the technology that's coming out?"—it always comes back to: the more personalized you can be and the more authentic you are, the more you stand out.

I'll give you an example. Recently there was a company that reached out to me and my partner Cassandra. We're going back and forth, and I said, "I'm curious. I've got my AI, I've got my data, I've got my reputation. Why did you pursue—" They were looking me up for six months. And their answer was, "We like you."

And I was like, "Fair. I appreciate that."

I'll use another example. My good friend Sheldon Poin from Drive Marketing—same thing. Tons of marketing agencies out there. People go up to him like, "We've been looking at you. We're interested in this." "Okay, we have these products: A, B, and C." "Yeah, yeah, yeah. That's good. When can we start?" "What do you mean?" "We like you."

That—as much as you can put up all the noise you want about how great you are—likability is very hard to mimic. That is a decision that people make based off of what they see and the intuition of what they get out of you, especially when you're showing your authentic side.

So there's likability, there's authenticity, and there's—what would be the third?

Lee Levitt: Trust?

James Stephan-Usypchuk: Trust, compassion. There are things that are hard to emulate.

A bot can be compassionate. I'll give you an example. Cancer patient. They're trying to book an appointment, distressed. They're trying to go through their treatment. An AI bot can be programmed to have empathy—

Lee Levitt: To ask the questions. "How does that make you feel?"

James Stephan-Usypchuk: Correct. "Are you okay? I'm sorry to hear that. Do you need something else?" And just be the person who listens. But when it comes to the actual human condition, this person needs to speak to a doctor, a nurse, a therapist—that gets on a wavelength that we will very seldom and with difficulty replicate.

Lee Levitt: I heard you almost say "never."

James Stephan-Usypchuk: Oh, I don't wanna say never because, you know, Blade Runner is a very good movie and I liked it a lot. And you never know—so is Altered Carbon.

But at the same time, I would like to think that we are in a society that still appreciates what is being said to us by whom—the credibility and the trust that that person has. Because whether they're a doctor or whether they're a person, the more credibility they have, the quicker you are to trust them.

But you need to be able to be in a situation where you can take them in as a person and say, "Okay, you know what? This person—they looked at me, they heard my problem, they're giving me ideas."

Lee Levitt: They put their pen down and they listened.

James Stephan-Usypchuk: Correct. And that's where moving above and beyond the noise comes from the human condition, which is something that I don't believe should be automated and I don't think can be automated.

Lee Levitt: Let's take that recommendation at face value. I'm in 100% alignment with it. So that suggests that we should not try to replace ourselves with machines.

James Stephan-Usypchuk: I think the only way that we should look at replacing anything is if we were to prolong life, end suffering, prevent disease—anything like that.

Do I think that we should plug cybernetics into our body? I think it's relative. I mean, there's the guy who has the Neuralink. He has a new lease on life. Who am I to tell him, "No, that's an aberration and that has no business"? No. If it helps a person and it's a novel of technology that improves quality of life and the human experience, go for it.

Lee Levitt: Let's go to the example of—I'm of two minds on this. If I'm a salesperson and I want to be better prepared to have a conversation with a new prospect, I can go and look at their website. I can go and look at LinkedIn. I can do all sorts of time-consuming research manually. Or I can have a service deliver that information to me in a nice, neat two-page package with bullet points and recommendations and key takeaways.

And that work can be done today. 20 years ago, we outsourced it. In large organizations, we nearshored it so that people who were paid a modest amount would do that research. Five years ago, we could Google it. Today, we just tell ChatGPT to go figure it out.

And I think that's good to a point. It's when we hand off the critical thinking and empathy building that it—instead of being a tool that helps—becomes a tool that masks the human condition you referred to. And now we're just reading from another script.

James Stephan-Usypchuk: Yes. My firm, Ecliptical, we do a lot of that on our own. We have tools that we've built, databases we've built. It goes out, finds the firmographic information, finds the stakeholder or the owner, gives us a psych profile. What's important to them? How old are their kids? Are they gonna graduate soon? Does the owner want cash to buy them a house?

I have all that data. What it doesn't replace is the fact that even if you have all that data, if you cannot connect with the person, they're never gonna give you the keys to their business.

So you have to use that data in an ethical way, but with the likelihood of trying to assess: What's my level of risk in pursuing this person, and what's the likelihood that they're gonna be interested in what I have to say?

The next frontier that I've been working on for the better part of eight years now is using that data to come up with predictions and probabilities of how likely something is to happen, so that way you maximize the time with those that you are connecting with on the human condition. That's where the honeypot is.

But whether you have that data or you don't, the endpoint of how you convert, how you close, or successfully conclude that relationship is still human. It's still the human condition. All this does in between is speed up the process and maximize who you're talking to.

Lee Levitt: And then it's still up to the individual to have that human-to-human interaction.

James Stephan-Usypchuk: Yeah. You might get people saying, "Oh, it's serendipity. How did you know?" You were very accurate. But at the end of the day, accuracy only brings you so long. If I am accurate and an asshole, it's not gonna happen. It's not gonna move the needle. They're gonna say they're never gonna talk to me again. So that human condition is very important.

Lee Levitt: So how does the next generation learn to be the critical thinker when they're fed this fiddle of information just for the asking?

James Stephan-Usypchuk: Well, it's the typical W's: Why, what, how, what's the purpose? Always ask why. Why am I doing this? Why is this information important? Why might I use A over B? How does this impact the person I'm talking to? How does this improve their life? How does it improve their business?

And if you can't answer those questions and you're just running blindly with what you're given, then you're a cog in a machine that has no direction. You are effectively part of the ChatGPT ecosystem rather than dictating and operating the ChatGPT ecosystem.

You need to know why you're doing what you're doing and that you are not harming anybody or causing any kind of damage when you're actually reaching out and leveraging the information.

But at the same time, you have to be critical about assessing what's good. My system spits out 90 out of 100 scored targets all the time. But before it goes to a client or a private equity firm that we work with, we always vet: Does this actually make sense?

This is 9 out of 10 for all the good reasons, but the company—the owner might be willing to sell, but the company just went through a lawsuit that's not been public yet or that's only recently released. That changes the multiples and the logic altogether.

So you need to really dig deep and understand why you're doing what you're doing, and does it still have relevancy even after consuming the data.

And you also have to question: Where's the data coming from? How accurate is it?

In my opinion, the best practice is to build your own data source that you know and you trust and that you constantly tailor and nurture like a garden. Because at the end of the day, God forbid something happens and you lose access to GPT or whatever—you still have that powder keg that you've just been filling for years and years that you can leverage, whether it's historical or you can use it as a reference point to find new groups.

Lee Levitt: The simple example I use is: you're an enterprise field rep working for XYZ Company. You're going to visit the VP of Marketing at a company in downtown Montreal or New York or Detroit or wherever. You get on the elevator. You're about to hit 3. And someone else steps on. You look over to her, you realize that's the CEO, and she hits 27.

You're not going to 3. You're going to 27. What are you gonna say?

James Stephan-Usypchuk: What can you say? At the end—

Lee Levitt: Well, I mean, you can pull out your phone and say, "Hey, ChatGPT, remind me of the deal here."

James Stephan-Usypchuk: Well, yes and no. At the same time, going back to likability—does that CEO really want to talk about a deal? They're on their way between—

Lee Levitt: Yeah. I mean, I didn't mean to use the word deal. You have 45 seconds-ish to make an impression on this person.

James Stephan-Usypchuk: Yes.

Lee Levitt: It's not about the deal. It's, "I'm here as a servant leader to help your company achieve better results in some area."

James Stephan-Usypchuk: I would argue in the 45 seconds you have, what are they gonna likely remember? Your ability to recall information? Or how charming or likable you were?

It's a lot easier to play to your strengths than it is to recall something. Because at the end of the day, it is the recall that is being replaced. That is not valuable.

The likability, the charm, the fact that you have emotional intelligence—that is what they remember. And next time they step in the elevator with you, they'll be like, "Oh, hey James, how's it going?" "Oh, great." "Same. Doing London Fog today." "Long night, whatever." "Cool. How are the kids?"

That's how you build rapport. And I can tell you, I know a lot of people who—let's say they exited one company, went to another—you'd be surprised how many people bring people they like or gravitate towards just because they know they work well together or they like how they vibe.

That's a big deal. And you're not gonna get that with ChatGPT regurgitating recall information.

Lee Levitt: Right. So one of the messages there is: if you count on your tech as the crutch—so you spend an hour with your tech and then five minutes on the phone with someone—when you hit that elevator, your tech doesn't exist.

James Stephan-Usypchuk: The only tech that matters is up here, man. That's really what's gonna drive the needle for anything.

And again, it comes back to: the more I want to cut through the noise and get remembered—and I'll give you a stat: the average person sees 15,000 to 20,000 ad impressions per day.

Lee Levitt: Say that again, because that stat is just insane.

James Stephan-Usypchuk: This was from 2012, so I guarantee you it's even more. The average person sees 15,000 to 20,000 ad impressions per day. That's the brands you wear, material you see online, where you drive, what billboards you see, what you hear on the radio. Everything you can imagine.

And if you imagine that much saturation—that we only have 24 hours in a day, you remove six if you're lucky for sleeping—now you're seeing all these different brand impressions. And you need to stitch together 12 to 15 to maybe 20 touch points, 20 quarters of a millisecond of seeing information, for you to remember three seconds of something for you to actually recall something.

Think about that and how advertisers are trying to get in front of you there. And then think about how does this three-second memory get compiled if I'm having an authentic conversation with somebody and I have 100% of their attention.

Just think of how you're supercharging that. And they're gonna be like, "Oh man, James, he's a funny guy. Or James wears funny shirts." Whatever. What matters is you caught the three seconds, and that's what they're gonna remember.

Lee Levitt: So, you know, for you and I who are public speakers a lot, the rule is: people don't remember what you told them. They forget 95% of it before they've left the room.

James Stephan-Usypchuk: Yeah, they might even forget your name. They might even forget your face.

Lee Levitt: Yep.

James Stephan-Usypchuk: They'll remember the feeling.

Lee Levitt: They remember how you made them feel.

James Stephan-Usypchuk: That's right. And I'm a goofball, so—

Lee Levitt: So am I. That's why we get along so well.

James Stephan-Usypchuk: You got it.

Lee Levitt: So in technology, the technology industry fights that because it is so focused on competitive positioning. "Our stuff is better than their stuff." Or, "Our stuff is 30% faster." "Our stuff does this and their stuff does that."

And it's like, I don't remember any of that stuff. All that's column fodder. We're gonna put that in the spreadsheet for making a decision, but that's not how we decide.

James Stephan-Usypchuk: A good friend of mine, his name is Michael O'Connors. He's the CEO of Life Change. It's an MSP in Kentucky. When I started working with him, he was always telling me his description of sales was "winning the hearts and minds of people."

And I always thought it was funny. I was like, "Man, that's such a weird and unique way of saying it." But the more you take a step back and look at it, that's exactly what it is.

It's, "I'm an MSP, I have all these differentiators. Sure, whatever." But do they like me? Am I someone they can trust because they feel good when I'm around or when I'm doing something?

Lee Levitt: Do they feel comfortable giving you a piece of their business?

James Stephan-Usypchuk: Exactly. And these guys work with utilities, infrastructure, government, banks. That's a high-trust environment with high-ticket sales. That just doesn't materialize overnight.

But if you think about it, his methodology and logic—regardless of theory, it was just his practical intuition of what he calls it—it's bang on. And it is absolutely the right way to think about it.

Lee Levitt: As we go headlong into this AI world—and by the way, it's not the first time we've done this.

James Stephan-Usypchuk: Nope, definitely not. And it won't be the last.

Lee Levitt: It won't be the last.

James Stephan-Usypchuk: But just to say, we're going into a space where AI is getting more aggressive. What, five years ago we were talking about crypto? And before that, Web3. And before that, programmatic advertising. And before that, social media. So there's always something.

And now ChatGPT is rolling out ads. The next frontier is, "Well, how do you optimize for ads in ChatGPT? How do you optimize for GEO and SEO so that when people look up something on ChatGPT, it pops up like Google?"

But the reality is those are all competitions to cut through the noise. But even if you get to the top, if you cannot connect on the human level, forget it. Forget it. You might as well save the money because you're not gonna be able to close all that top-of-funnel traffic that you're optimizing for.

And I can tell you I've had dozens and dozens of scenarios where I was brought in—or pulled in, in some cases, by my hair—saying, "We need help. We need to fix this." And then when you do an actual audit of the funnel and you realize that the issue is not on top of funnel but all the way at the bottom—it's the human element that's often forgot.

Lee Levitt: Yeah. You know, in talking about the funnel, four to five reps fail on the first call because they're pitching rather than asking questions. This is in enterprise sales. One out of five actually asks good questions. They actually come in with a point of view and a business value hypothesis and they ask questions and they start a collaborative discovery.

Here's an interesting stat: customers typically change what they're looking to achieve three times in an enterprise deal. So even a good rep has to both follow that process and guide that process.

James Stephan-Usypchuk: Yes. I actually lived this last week. I was on a call. It was a product that I was curious about. I was demoing it with a buddy of mine.

The sales rep got on the call. We introduce ourselves. We're pre-sold. We are pre-sold. He says, "Hi. Okay. I'm gonna just start..." And then blah, blah, blah, blah, blah.

And I'm like—we were messaging each other on the side, like, "Is this happening? Do they not realize we just want to see the product demo and get confidence that this is not bogus?"

Lee Levitt: Read the room.

James Stephan-Usypchuk: Yeah. But again, a lot of people don't know how to get out of that comfort zone. Their comfort zone is this script. "This should always work. This should always work." But you lack the critical thinking and the emotional intelligence to figure out, "Oh my God, I just need to get this person to like me."

I've had PE firms that'll say, "Proposal is no problem. We're a hundred million dollar company. You're asking for whatever—20K, 30K a month. Doesn't matter. Finance is not the issue."

You get to know them a bit. You go back and forth. And you realize it was trust, and it was they need to like working with you. That's it.

That is the simplest of all the recipes. It's not more ChatGPT. It's not "what can Claude tell me to say differently." It's not what Crystal can say with their psychographics. You get past that. And the final part is the art of—I wouldn't just say selling. It's the art of—

Lee Levitt: Being a human being.

James Stephan-Usypchuk: Being a human being. Exactly. The art of improv. Listening and being in the moment.

Lee Levitt: Some of the best salespeople I've ever met have been comedians, because they're quick, witty, likable, on their feet.

James Stephan-Usypchuk: Yeah, Dan Pink says that improv and enterprise sales are the same thing. And when I first read that, I jumped right into improv and I joined a local improv troupe.

Lee Levitt: Oh yeah?

James Stephan-Usypchuk: I've been having a blast because you have to be present. You don't have time to think. I've been told this before: thinking gets me in trouble.

And so being in the moment and responding—having the muscle memory to know how to respond when a customer says X, and follow their lead or guide them—is far more powerful than sitting there thinking, "What's the best response to that? What should I say in response to what that person says?"

It's like, now you're not being a human being. Now you're writing and then reading a script.

Lee Levitt: You know, talking about two goofballs—before, when I started my business, I was 17. I had no idea what I was doing. But I got quite a few clients pretty quickly because they just thought I was funny as hell. "Okay, let's give this guy a shot. He's hilarious."

James Stephan-Usypchuk: Yeah, exactly. Worst case, it's comedy. Best case, you got something. Obviously, I delivered. But it's a very interesting social experiment. I have a lot of friends that are quite funny. And the common denominator is they're really good at sales.

Lee Levitt: Those attributes go together.

James, this has been a fabulous conversation. Where can people find you?

James Stephan-Usypchuk: So you can find me on ecliptica-ops.com, which is our firm. I would say the second-best place to find me is on LinkedIn. I have 15,000-plus people on there and I'm very, very active. I occasionally am on different forums like Search Funder, et cetera, but LinkedIn's the safest place.

Lee Levitt: I will put links to both your company and to your LinkedIn profile so people don't have to try to spell your name—although it will be on the screen.

James Stephan-Usypchuk: Talk about the human condition. I guarantee you they won't forget that.

Lee Levitt: There you go. James, this has been an absolute pleasure.

James Stephan-Usypchuk: Thank you, Lee.

Lee Levitt: Another deep dive into the topic of sales excellence and the performance mindset. If you found this conversation interesting, I would appreciate it if you would share the podcast with a coworker or two. And to explore this topic in more depth, send me a note via the contact form at podcast.thoughtsonselling.com or find some time for us to talk at aceleragroup.com. Thanks.

James Stephan-Usypchuk Profile Photo

Managing Partner

James Stephan-Usypchuk is a strategist and operator with 15+ years across AI, marketing, sales, and deal origination. He works with founders, private equity, and family offices to build off-market pipelines, capital readiness, and scalable growth systems—turning messy opportunities into decision-ready assets.