Why Creatives Struggle With Sales (And How to Fix It) | Yaacov Steinberg

In this powerful and deeply relatable episode of Career Coaching Secrets, host Pedro sits down with sales coach Yaacov Steinberg to uncover the real reason why so many talented creatives struggle to sell—despite producing work their clients genuinely love.

Yaacov opens up about his journey from being an introverted outsider growing up—navigating ADHD, sensitivity, and social challenges—to becoming a top-performing sales professional and trusted coach. Instead of relying on traditional “pushy” sales tactics, he developed a human-centered approach rooted in psychology, empathy, and genuine connection.

This episode dives deep into the mindset shifts that changed everything for him—especially the powerful transition from focusing on perception to embracing perspective. Yaacov explains why most creatives fail at sales not because they lack skill, but because they’ve been taught outdated, transactional methods that don’t align with who they are.





Connect with

LinkedIn: https://www.linkedin.com/in/yaacovsteinberg/
Website: https://calendly.com/yaacovsteinberg/call?month=2026-04

Transcript

Yaacov Steinberg 0:00

Being the outsider, I didn't have any friends growing up in elementary school or high school until I I learned how to have those social keys. And that that comes with the ADHD territory, it comes with being introverted, comes with being sensitive and feeling like I had a target on my back. And when I was willing to step out of myself and stop looking at the perception that I had and pay attention to the perspective instead, that was a huge shift. I think a lot of people, they're in a certain moment. Am I even going to say, you know, fixed mindset to growth mindset? I think we just need to a lot of times change the way we're looking at things. That's the first point, you know, that I want to make. And that'll lead me into the second, which is that, you know, you mentioned objection handling. I always like to say, you know, even from when I had my podcast, a good conversation, as you demonstrated today, is three pieces. It's asking good questions in the right way at the right time.

Davis Nguyen 0:41

Welcome to Career Coaching Secrets, the podcast where we talk with successful career coaches on how they built their success and the hard lessons they learned along the way. My name is Davis Wynne, and I'm the founder of Purple Circle, where we help career coaches scale their business to $100,000 years, $100,000 months, and even $100,000 weeks. Before Purple Circle, I've grown several seven and eight figure career coaching businesses myself and have been a consultant at two career coaching businesses that are doing over $100 million each. Whether you're an established coach or building your practice for the first time, you'll discover the secrets to elevating your coaching business.

Pedro 1:12

Welcome to Career Coaching Secrets Podcast. I'm Pedro and today I'm joined by Jakob Steinberg, who has cracked the code on why talented creatives struggle with sales despite producing work that clients absolutely love. What makes Yakov's approach unique is his recognition that most branding experts, agency owners, web designers, and video producers aren't failing because they lack talent, but because they've been taught sales the wrong way or not taught at all. Yakov specializes in helping creatives land high-paying clients consistently without awkward sales tactics, focusing on clarifying messages. Dream clients instantly see value and using conversations to create demand rather than chasing leads. His clients consistently report dramatic results, with some closing K within three weeks, and others seeing 200% sales increases, proving that when you build the right system, sales can feel effortless rather than exhausting. Welcome to the show, Yakov. Thank you so much for having me, Pedro. Really excited to be here today. Yeah, it's great to have you, you know. And you know, I'm a super comic book nerd, and I love to dive into the origin story, you know, and rewind a bit because every coach has that moment where they look at their life and say, Yeah, I guess this is what I'm doing now, right? So when was that for you, Yakov?

Yaacov Steinberg 2:44

I mean, it's really interesting because like my story goes way back to when I was a little kid. I mean, I started sales coaching itself officially about a little over six years ago now. Um, but my origin starts as my parents like to tell the story. When I was five years old, I sold a secondhand pair of broken sunglasses to a classmate for like five bucks. And my parents made me give back the money, but they always like to say it started when he was young. Um, but for me, I'm an introvert. I'm sensitive. I was, you know, I've ADHDs, so I never really got how to sell myself. I was always the outsider in the story. And I was always that kid watching someone else sell at the lemonade stand, wondering how they got it done. And at a certain point, I'd say it was in high school, um, I really got sick and tired of being that outsider, started paying attention to the psychology, behavior, connection. You know, who did people want to hang out with? Why did they want to hang out with them? And what I started doing was really focusing on understanding that element. And that led me down the path of psychology. Eventually, it led me into the teaching space where I was able to get kids to be sold on their own potential, believe in themselves, and really believe they could make a difference and they had self-worth. I mean, some of my hardest sales were getting seventh graders to do things they didn't want to do. Like, I'll never forget. First test, first day, kid comes in and he goes, Oh, just write a zero. I'm an idiot. I'm like, first of all, come on, we're not gonna talk that way in this class. That that stays at the door. Second of all, let's go through it together. And that kid ended up in an amazing high school by the time he got there because he learned how to trust himself, how to believe in his own potential. Um, as time went on, I went into sales proper. And the amazing thing was is like in my first 12 months, I'm gonna say, in being in a sales position, I was already bringing in 20% of the monthly recurring revenue of the company that I was in. They had a free trial to paying customer that adoption issue by about 400% in that same time. Eventually I became their VP of sales or director of sales. And when I left that company after, I don't know, about three and a half, four years of being with them, um, I started other positions, but I started pro bono consulting on the side. I started just helping people. I felt like I had what to give back to the community and others around me. And eventually at the end of 2019, the people that I was helping were just seeing kind of ridiculous results, like 40K in 30 days, uh, sorry, 30k in 40 days. And it was just unbelievable. And I was about to go into a more corporate position that I was gonna plan on staying in for a bunch of years. And I'll never forget it. I my wife had just had a baby, and we were in the you know, after you go to the hospital, a lot of times you can go to like a special, you know, mommy daycare center kind of thing. And you know, the mom is taking care of the baby's taken care of. I was on the porch and I'm on the phone with my client, and she says to me, Yakov, you could totally go into this corporate position. You're gonna smash it, but we need more of you, not less. And I was like, Oh, come on. You get right where it hurts. You can't do that. I was like, I got two weeks, three weeks to make this work. I'll tell you what, I'll give it a shot. I ended up closing like three clients in those two weeks. I called the company. I was like, look, I gotta give this a shot. This is one of those moments. If I don't try this, I'll never forgive them myself. I had a great relationship with them. They were like, yeah, no worries, man. Doors wide open, go for it. And it became a dream come true. I mean, COVID happened shortly afterwards in uh, you know, February, March of 2020. And the crazy thing was, they were actually that company, that corporate company was hiring me for like an elite sales team. And that whole team had to shut down because of COVID. And they had to like rearrange everybody. And here I was in my own business, helping people trying to change, you know, the world. Fast forward six years, it's been a dream come true, right? My my job today, I like to say, brings my three biggest passions together sales teaching and helping people, but not necessarily in that order.

Pedro 6:27

You know what I mean? Oh my God. So high school, you were sick and you got sick and tired of being sick and tired, and then you move forward, start helping those kids, and then we move to sales. From sales, eventually you got yourself in a crossroad, right? Exactly. Do I take this corporate job or do I hear my wife who says, Hey, we need more of you, not less. I love the quote, by the way. Okay. Very interesting.

Yaacov Steinberg 6:52

And listen, that client today who said we need more of you, not less. Uh-huh. We have an amazing relationship. She's a huge advocate. And I we're always talking because, like, ultimately, like, I have such gratitude to her for pushing me in that moment, right? And realizing a lot of times we don't realize we're in a specific moment until like we're way beyond. But like, this was one of those times where in the moment I was like, This is that moment. Like, I'm gonna either hate myself for the rest of my life that I didn't take this chance, or I'm gonna take it. Worst case scenario, it doesn't work out, and we'll go back to whatever it is I was gonna do anyway. Okay.

Pedro 7:24

So I want to ask you something, and this is something I usually ask in the show. It's like the shift, right? When when did you felt it from I'm helping people to I'm building a real business around this? You know, I'm not sure it's the first paying client, I'm not sure it's the LLC or the first invoice, you know? But when you grabbed the hat of coach and CEO of your own coaching business, when when that happened, you know, when did you feel like you're telling others, like, hey, I'm a sales coach? You know?

Yaacov Steinberg 7:50

I mean, like, I definitely was telling people early on in the journey, probably in the first year, even that, you know, this is what I'm doing now because I'm a big believer. Like, if you're gonna do something, do it. Uh but it what it definitely didn't feel like it was something real until a couple of years in, right? I was doing the thing and all of a sudden I was I looked back and I was like, wow, I've worked with a lot of people in the last couple of years, and look at the impact that's had, the ripple effect when you work with the a founder-led sales company, right, in graphics or web development or branding, whatever have you, just giving some examples of some of the people I work with in the creative space. And they just have this, you know, all of a sudden this light bulb. You speak to them a couple years after you've worked with them, and they're like, you know, we started, I was doing 450k a year, and now I'm doing well into seven figures. And it was like, oh my God, these people have been able to hire so many more people, their business is set up differently, their families, those people's families. Like, look how far this really goes. And it, I just fell in love with the ability to impact so many more people by being in that moment and being able to be of service to my community and to others around me just by being able to be a sales coach and showing people that there is a better way than selling your souls and having to be like a used car salesperson that nobody wants to be around. And you're trying to call people and they're like, I can't talk to this guy anymore. I don't answer his phone calls. And all of a sudden it's like, no, I want to be around this person because they they're just being a human being asking me questions. And that's what a good conversation is all about asking good questions the right way at the right time. It's just a matter of us realizing it's that simple.

Pedro 9:21

Okay. So the spotlight is on me, so there's a lot of pressure. I'm asking the questions. I get it. Okay. I'm gonna try to do my best. I'm gonna try to do my but my now. I want to understand one thing, okay? Because after you got rolling, were the people that kept showing up. You know, I understand that we're we we talk in the intro, some creators and all that, but I want to understand the ones you realize when you're a little bit down the road in the business, okay, this is my tribe, you know? And even if you got to that point. Yes, I mean, initially it was much more general.

Yaacov Steinberg 9:50

From a sales perspective, a lot of times we speak about niching. A lot of people talk about this idea of niching or niching, depending on who you ask. And I'm a big believer that when you're doing it from a sales person perspective, and Marcus Chan talks about this a lot, a mentor of mine. You have to make sure that when you're targeting people, you know who that person is. Who's the ideal human profile person I want? So initially, when I started out, I didn't want to limit myself. So I was working with just general businesses, people, every everyday businesses, people in general. I remember I worked with someone in HR, I worked with someone in shipping and billing, medical billing, and that still happens today. But at a certain point, I started looking and I said, wait a second, why do I like creatives so much? Right. I started noticing a lot of people I was working with were in the creative spaces. And like I mentioned earlier, those are people that would say that are being branding, they're in photography, videography, they're in, you know, graphic design, web development, things like that. And I've noticed, as someone with ADHD, I'm a right brain thinker. And people in the creative space are also right brain thinkers. And a friend of mine had come to me around that time and he said, he was also in the training space. And he said to me, Yaakov, I don't get it. How do you work with all these creatives? I mean, like they speak a completely different language. I'll tell you what, you work with all the creatives, I'll work with everyone else. And I, it was like at that moment, I was like, like the it just fell like in that moment, like I got more of the story and like, why do I connect with these people so well? And it was because if I look back at the story that I own today, I definitely didn't own the fact that I was introverted and I was, you know, ADHD insensitive. I didn't get all that till, you know, a couple of years ago through a tremendous amount of therapy and being willing to stop being an extrovert that I had become and step back into being into that introvert, um, you know, which maybe we'll end up talking about. But it was in that moment that I realized creatives don't, it's it's the antithesis of who they believe they are to be a salesperson, to push somebody else. And in the original story I used to tell, it was like, yeah, I sold a second-hand pair of sunglasses when I was a little kid. And it made it seem like I always was a natural salesperson. And that wasn't true because even though I might have understood some of it, I didn't get how to do it in reality. I wasn't selling lemonade. I never was that entrepreneurial kid, right? And it was at that moment that I went, This is my people. It's the people that they don't get how to do it initially, like I didn't. I had to learn this skill, I had to learn this trade, I had to understand it from a psychological perspective, behavior, etc. And then I was able to go and actually do it. And that's when it hit for me that this is the people that I like to help.

Pedro 12:20

Ah, okay. Okay. Now I want to do a quick exercise with you, okay? Pretend I'm one of those creatives, right? I'm like your ICP, however, your avatar, however you want to call it. Now, how first marketing. How do I would be eventually find my way to you in the first place? A lot of people, it's a great question.

Yaacov Steinberg 12:38

So a lot of people find me through LinkedIn. A lot of it's word of mouth and referrals. Some of them is, you know, they'll find me in WhatsApp groups and stuff like that. Um, I have a podcast, so it could be that they'll come through, you know, the podcast journey, whether it's Spotify or YouTube or wherever have you, wherever they might find that. It could even be my newsletter, right? There's a lot of things out there that I believe strongly in, giving people knowledge and allowing them to, you know, consume it at their own pace. Not everyone's ready for one-on-one coaching, so I like to just, you know, put out information. So there's a lot of places that people will find me. I'm very active on LinkedIn. That's an easy place. Now they'll come into my space, they'll see more or less where it is that I'm, you know, what it is that I'm doing, how it is that I'm talking to people. They'll get a sense of what it is that I believe in. And then at some point along their journey, whether you know they went through a course, let's say that I put out, or they decide they want a strategy call because I like to, you know, help people just because we'll end up on a call, they'll see how it is that I interact with them, they'll see what it is that I believe in and the different mindsets that I'm sure you'll ask me more about. And then from there, they'll decide, you know, what it is that makes sense for them. Are they at the stage where they're ready to actually get structured help to really make a shift, which is what coaching is all about, as you know, we both well know. Or are they going to continue trying to do it the DIY version and spend, you know, twice as much time trying to get to that same position, but it taking a lot longer. Okay.

Pedro 13:57

So still in that exercise, I'm still creative. Like you said, I looked at your LinkedIn, I heard or listened to one of your podcasts. I'm like, hey, we got into a hop, we hop on a call, right? A sales process and all of that. Let's say there's alignment. I felt like, hey, Yaakov seems to know his stuff. I want to work with him, right? So walk me through the point of view of a client, be on board it. Okay. How does it look like? How do we structure a business and the potential outcomes I would be looking for, you know?

Yaacov Steinberg 14:24

It's a great question. So the people that come to me, most of the time, they're dealing with a couple of common issues, right? And a lot of times, I mean, the two main ones that I talk about are going to be feast or fame and sales where one month they're book selled, the next they're scrambling for leads, or selling just feels awkward. They don't want to be pushy, being nice isn't really helping them either. And they want to be able to feel confident, have clarity, and have structure. Those are the main things that people are missing. So it could even be that they believe in what they do, but they don't have the confidence to sell it or to pitch it, or they're not even sure how they should be talking about the offer, how they should structure their pricing, et cetera, et cetera. And there's usually about six different things. I don't want to spend too much time going through each of each one individually. But once we have clarity on what specifically is going on in their particular situation, so then I'll be able to show them one. I'm a big fan of trying to give empower people that here, these are things that you can change right now. You can go download this from my, you know, LinkedIn profile, or you can listen to this podcast, those things can help you. If we are going to go on the coaching journey, so then I'll take them through that process, what that looks like, and then we're off to the races in terms of you know working together, helping their specificity of what's going on and making sure that they're able to. I like to say there's two parts to this process is one building a vessel that can hold water, because so many people they have a leaky pipe, and then being able to fill that vessel with water and being able to make sure that right things are going into it and you can handle whatever's happening.

Pedro 15:50

Okay. Now I want to throw you a little bit of a curveball, especially for the coaching space, right? Uh and I can sense it. You're very passionate about the practice itself, okay? And your work seems pretty hands-on. We're talking about the sales process, we're talking about the coaching podcasts, you name it. Okay. Wearing a lot of hats, doing a lot of things. So, how do you think about capacity? So you don't stretch yourself too thin. You don't burn yourself out, you know. How does that play out for you?

Yaacov Steinberg 16:19

It's a great question. So I'm working with a lot of people that are founder-led sales, right? So a lot of those people, not everyone is gonna be. I mean, I first started off, plenty of those were in startup mode. I'm working now with, you know, seven, eight-figure companies, even the you know, six-figure level, where have you. There's a nice range. Now, ultimately, at the end of the day, these people need a lot of work in between sessions, right? So I even offer unlimited support in between session because I'm a big believer in implementation and execution. And a lot of that's gonna happen in between. So for me, a lot of the stuff that I need to do in terms of the, let's say, admin of the business, I make sure to use the right system. So I don't want to be, you know, at a certain point, I had to say, hey, wait a second, if I'm charging XYZ and let's break that down per hour, I'm actually losing money every time I'm chasing somebody for payment if I ask that because something didn't work. So I use a credit card processor. I make sure that I connect that, you know, with QuickBooks so that I have all my accounting is taken care of. You know, for me, I go in there, you know, once a day just to, you know, update things and, you know, once a month to make sure that everything's reconciled. I make sure to use a lot of Chat GPT for ideation and helping me to think creatively, not letting it rent my brain for free. But also making sure that I'm using AI in the right way to make sure that I'm constantly innovating, staying ahead of myself. And even now, like I'm actually in the middle of this process of getting to the next evolution of the business where rather than doing, you know, onesie twossies, it's you know becoming one-to-many. Rather than it being manual, you know, what in the attract phase, it's you know, we're we're working towards automation. When it comes to delivery, you know, all of these things need to shift as we grow as a business in order to continue helping more and more. Okay.

Pedro 17:58

Love that. Now, like uh I feel the need to, you know, highlight a point of your experience that I think it would be very interesting to go within a dip dive real quick, which is the you did pro bono work, right? And I've seen a lot of coaches that did pro bono work, and sometimes they tell me, you know what, Pedro, uh, what happens is that people don't have enough skin in the game, there's no commitment, and they know show and they don't really put in the work, you know, because it's free and they perceived it unfortunately sometimes as unvaluable, right? There's no it's worthless or something like that. So what's your take on it, right? Well, you since you did the pro bono and you're now charging, like, do you see that difference? How did that play out for you?

Yaacov Steinberg 18:40

Sure. I mean, I think that it has to be strategic, right? So, I mean, I have a friend um who was actually also a sales coach at one point, and today he does something completely different. He told me when he first started his second business, um, he actually went to a lot of big people on LinkedIn, offered them his service for free, had all of a sudden a bunch of testimonials and really big names on the platform, and then he started charging for his service. That's a really strategic way of doing the pro bono. Now, alternatively, anybody starting out has to have some people who are gonna vouch for that. Right? You could talk about your story and how amazing you are all day long, but if you don't have anybody who's backing you up, it's not gonna get you very far. So there is the strategic pro bono way of doing it now. When it comes to depending on who it is that you're looking to help, there is a big saying within the sales coach, within any coaching space, really, I should say, that if people aren't paying something, even a dollar, then they're not gonna ascribe value to what it is that you're giving them. And there is some truth to that. There's no question. At a certain point, people take it for granted. They don't, you know, they stop doing the work, but it really depends on who you're working with, right? And that's always been my take. Like I had, you know, different times in my own journey where I've been on the receiving end of people just being nice. And I like to pay that forward. And when I've done that as well, when you have someone who's really driven, but they're not necessarily in a position where they can necessarily pay for something, but they really need it. And you're saying, look, if you're gonna really commit to this and you're gonna do what you need, I'm happy to be here for you. The second that you go off the script and you stop doing what you need to and you stop committing to it, this is gonna have to stop. If you could set the right boundaries around it, it can work, but I don't, I still don't suggest doing that as a long-term, you know, strategy, right? It is good in the short term, it depends on you know each individual situation. Uh, but as time went on, I did come to realize more and more the people who really sunk their teeth in it all were those that were paying for it and ascribing the value that it took.

Pedro 20:38

Okay. Now, you kind of browse through it already about, but I want to talk about future, right? I'm curious about where you're taking all this. Like looking ahead a bit, where do you see the business going? Are you thinking about scaling, hiring, or is there a next step you're excited about, Yakka?

Yaacov Steinberg 20:52

Yeah, definitely. So, I mean, like at this stage in the business, I mean, uh, we're really blessed. I thank God. We've been doing this for over six years, and we've had just about a hundred clients in one-on-one already. Um, so recently we put out I put out a course, um, which is really exciting, like a digital course that people can do, you know, self-paced, self-driven stuff like that. And for me, I see the next evolution as being more in, you know, groups, having still one-on-one, because I really like that power, but having more groups, more of the other offers that are gonna allow more people to be able to come into the space that I sit in and allow them to be able to get, you know, the information they need at, you know, different w tiers and ways of being able to grow it. But it being at a much higher level, whereas now at a certain point in the business, you have to realize you're trading time for life when you're in a one-on-one coaching business. That's just the reality of it. There's only so many hours in a day and only so many clients you can have within that time space. So at a certain point within the evolution of the business, you need to go from doing onesie twosies, as Taki Moore calls it, to going one to many. And when you hit that evolution, when you go into that phase, a lot of things need to, you know, change within the, you know, internal structure of the business to support it. But I do believe that's where we're heading right now. It's moving more into bigger possibilities of more people coming in and being, you know, within the space rather than it just being mainly focused.

Pedro 22:10

Okay. Exciting, you know, from one to one to one of many. And you I think you nailed it. It's it's like trading your time for money that that it's capped at the end of the day, right? Capacity, something like uh will be there present uh every time you just set it up on a one-on-one. Now, of course, whenever we're aiming towards the next chapter, we're talking about future here, there's always something we're refining, right? In the present. So what are you currently trying to improve or tighten up in your business right now?

Yaacov Steinberg 22:38

So, I mean, right now, one of the things that I'm looking at is the attract side of the business, right? Making sure that I'm not this well, you know, well-kept hidden secret within the, you know, sales coaching space. Um, so a lot of collaboration is happening right now. I'm speaking to a lot of other people that I connect with and uh, you know, a synergy level that I believe in. I like the work that they do. I mean, collaborating with them, you know, some would call it cross-pollinating your communities. I know, I think that's a little fancy, but for me, it's really just helping more people. And when you can find someone that shares the values that you find that you have, I think that it's a really great opportunity for partnerships and relationships that you can help more people. So that's one of the things that I'm doing right now, making sure that I'm giving the opportunities for more people to come into the space. Um, that's really the biggest thing that I'm focusing on right now is tightening that up. And then, I mean, that'll lead potentially for me right now. I'm actually, you know, I mentioned Taki Moore earlier. Uh, one of the things that I'm hoping, you know, is to join his um his potential May Black Belt program um that I'm actually in the coming, you know, the next day or two planning on uh applying for. I've been looking at it intensively. So I guess this is a plug for Taki Moore. Uh, but I've been intensively looking at that over the course of the last couple of weeks and just like, you know, it's the classic you you find somebody and you, you know, connect with what it is that they're saying, and you end up going through their ecosystem until you get to a point you're like, okay, I want to work with this person. Um so he does that really well, and he's amazing at helping coaches to be able to get to that next level as well, um, which is exciting for me because you know, I'm looking forward to seeing where that leads.

Pedro 24:08

Okay. You know, I want to tap into your experience for a second because people listening can really benefit from this. You've been in the game long enough, right? To hear all kinds of business advice. I wanna, I want to specify in the sales, okay? Because I feel like a lot of coaches struggle with that, right? Because they, like you said, they had uh the the bad experiences in the past, and they're like, oh my god, I don't want to do sales because I want I don't want to be that guy, right? So I want to hear from you, right? What's one piece of I would call it sales advice you hear all the time that you think is overrated or misunderstood?

Yaacov Steinberg 24:43

Overrated or misunderstood. I think the idea of I'm gonna go the other way, so I'll apologize for this in advance, but I think it's misunderstood. So a lot of people, there's this thing called the zone of resistance. Josh Braun talks about this all the time, right? And I think we've all experienced this in one way or another. It's a department store, it's an outlet store. You walk in, and the first thing that the person does when you come in, a rep comes over and he says, Hey, welcome to Brooks Brothers, how can I help you? And right away you're like arm's length, like, nah, I don't need any help, please go, right? And what if instead that person came over and they said, Hey, welcome to Brooks Brothers, I'm over here folding shrimp shirts, just let me know if you need anything. And you're like, Yeah, I'm looking for that shirt and get a blue. Right? What happened? And I think that one of the biggest things that people misunderstand when it comes to the sales is that in the first example, we felt a pitch coming. So we automatically close up, we clam up, and our arm's length, please go away. Right. In the second example, what they did differently, they ended up and one of the biggest mistakes I think that people make, and I think that is misunderstood, is people aren't inviting people in, right? They're not inviting people into their space as an opportunity. Hey, this is the value that I bring, this is what I'm doing. You want a part of it, you want to be here fantastic. If not, that's also great. Right? Nobody owes us anything, right? They'll do pre the from the sales rebellion that um I have a great relationship with. Shout out to the sales rebellion. So, you know, there's a a really big aspect in terms of changing that a lot of you know, classic salespeople, they're knocking on doors, they're pushing an agenda, right? And we want to leave that at the door, right? Right? We want to be of service, we want to go the extra mile, we wanna be able to have a true servant leadership. And that comes from situational awareness and trying to make sure that we really are creating a win-win for everybody as well. Like, can we see everybody within the conversation? Can we project a future outcome where everyone's gonna win, right? Et cetera, et cetera. And when we do that, when we truly are of service from a sales perspective, not because we want another sale, not because anybody owes us anything, but because we truly believe that this is the best way to create experiences, to do things that are different, that maybe are a little edgy, but that are gonna give someone an experience that they're never gonna forget and they've never been treated that way before. We're truly able to do things in a completely different and I think more human way than people that people have forgotten over the course of the years, where sales has been around forever, right? There was always bartering, there was always something going on. But I think that human interaction, that human aspect of it has been forgotten along the way. And I think it's truly misunderstood what sales really is and the part that it plays in every business. Every business owner is a salesperson, right? And at some point they, you know, maybe move into more of a you know backspace. Um, you know, they're not as involved. So it's more back end and they let other people take that, you know, role of salesperson. But there's going to be sales in every single business.

Pedro 27:31

And the question is, how do we approach that opportunity? You know, you remind me of the time I was a high-ticket sales closer. And uh before that, I had a, I would call not a bad experience, but not optimal with uh sales. And there is what there was this belief that if you gave people a way out, they would take it, you know, and that's coming from a scarcity mindset, like, oh, I cannot give people a way out. I need to push them towards this funnel or towards this offer. So that really hits home, you know, and and how that that is just not, I think, the way to do things. And I think you nailed it, you know. Now, yeah, on uh but now on the other side, what's a piece of advice you wish more people actually took seriously in sales, for example?

Yaacov Steinberg 28:16

Seriously that is good or seriously that it's bad?

Pedro 28:19

Seriously, that they should be listening or they should be doing X, Y, and Z. So good.

Yaacov Steinberg 28:24

So in reality, I think a lot of people, I hear this all the time. They say, you know, I'm I'm speaking to people and it's not working. Right now, there's a couple of different reasons why that could happen, right? A lot of times people will say no for a myriad of reasons. Let's say the three main ones are gonna be the lead is off, you're talking to the right person, the pitch, you don't sound exciting enough, you're not hooking them in, really showing them an actual pain point they're experiencing, something of relevancy, or the timing is off. Now, within timing, let's say that's something you can't really control. Okay. Within the leads, you can get better at figuring out who is the person you're talking to, right? We'll call that the ideal human profile. Who do you really need to speak to? And the pitch. Who is it that how is it that you need to speak in a way that people are going to tune in instead of zoning out? And I think those two pieces are the biggest things that people hear, they need to focus on it even more, I believe, in terms of really nailing down, they take it seriously and making sure they have this demographic down and they have clarity on this is the person I want to talk to. It's, you know, a mother got a bunch of kids, drives them in an event, and you know, XYZ. And a lot of people in branding, they'll focus on some of that surface level stuff. But the real people that are doing it, a lot of the the real professionals, they're going a step deeper and they're going into the psychographics. And I think that that is something that is very important. And it leads to no like and trust when you can speak the right way and you're saying the right things, and people are like, oh, yeah, that's that's exactly what I'm experiencing. But I think it could even be taken another, another level deeper. And really understanding the psychographics. And what I mean by that is the deepest desires, needs, wants, fears, worries, the limiting beliefs external, internal, that your potential client is experiencing and understanding what's going on up here. Marcus Chen talks calls that the whisper test. Can you walk into a restaurant where your perfect client is sitting having dinner with their spouse, let's say, and you walk over and you say, Hey, John, you know, I know that you're dealing with X, Z is keeping you up at night, and F makes you just want to quit. I'm gonna be sitting over there if you want to talk to someone. But if you hit those on the head, they're gonna come walking over. I don't care who they're talking to. Right. And it's because when you get it right, and that leads to you saying the the, you know, what I like to call the context pitch in the right way to give over who you are, what you do, the people you've worked with, let's say, and the impact and results that that's had, it's a different game. Completely different conversation. Not from a manipulation perspective. I don't believe in that type of stuff, but from a revealing perspective, you're revealing urgency, not creating urgency. Creating urgency is fake, but you're revealing the urgency that's already there, but that they don't even realize.

Pedro 30:55

I love that, man. And and if someone listening and wants to connect with you or follow your work, where can people find you and connect with you?

Yaacov Steinberg 31:02

So, I mean, anybody can find me on LinkedIn. Um, I'm very active on the platform. So, you know, and my handle over there on LinkedIn is just Yaakov Steinberg, Y-A-A-C-O-V, S T E I N B E R G. And so that's one easy way that people can find me. You could look up my podcast, Win More on Purpose. Um, so that's Win More, comma on purpose. People always ask, what why the comma? I said, well, it stands for two things win more doing it on purpose, and win more with purpose. That comma's got to be there. And so that's the podcast. You could find that on, you know, Spotify, Apple, uh, YouTube as well. We have, I think, about 50 episodes that are up there. For right now, the podcast is on pause, but that is there, and all of that can be found. The links to that stuff uh can also be found on my profile on LinkedIn. Um, and there's a newsletter there as well. So, I mean, those are all places, and I think that uh there's a lot of opportunity for people who want to learn more about what are some of the different ways that they can be doing things and show up in a different way.

Pedro 31:56

You know, there were a few things that you shared today that really stay with me. I would say the secondhand sunglasses for four bucks, right? The origin story, I really like that. That's very interesting. Um, I would say also what you brought up about the the car salesperson that nobody wants to be around. Sometimes it's so much about the past, right? When we're talking about sales, bad experiences, and and the the misconception most people have of sales based on just terrible reps, I would say like that, you know, and and sometimes not even their fault. And that will be add to my third point, which is when you mention are you talking to qualified leads, right? Talking to ride pit, the people or the pitch, you know, are you doing the proper pitch, the demo, or some people may call. And what that brings me up to is two things, right? If you have that not dialed in and it's not optimal, eventually, first you you're potentially burning a lot of reps, you know, the the sales reps, you're you're firing people based on sometimes something that lacks structure, first of all. And second, it's like the objections, right? I see a lot of people talk about objections, like they're but there are the symptoms. We need to attack that. But sometimes if you do a very decent and in a very proper way and you're talking to the right people, most objections, they wouldn't, they sometimes they'd even they don't even show up, you know. It's so naturally done and so well constructed that it's just like, hey, how do we work? You know, it's like it's and and when you see that happening, it's something that is really magical because I see a lot of coaches that they're looking at their, I don't know, like their less email list and they have zero nurturing effect, and they're like just pushing like a salesperson or a sales car, a sales bad person, and they're like, Hey, why am I not generating revenue? When at the end of the day, they're just thinking about selling instead of serving. So I love those reminders, especially personally for me, right? Because I was in the game, so yeah, absolutely. This is my long-winded way of saying, Yakov, that I appreciate what you do. She appreciates you being here and sharing so openly today, okay? It was great having you on.

Davis Nguyen 34:02

That's it for this episode of Career Coaching Secrets. If you enjoyed this conversation, you can subscribe on YouTube, Spotify, Apple Podcasts, or wherever you're listening to this episode to catch future episodes. This podcast was brought to you by Purple Circle, where we help career coaches scale their business to $100,000 years, $100,000 months, or even $100,000 weeks, all without burning out and making sure that you're making the impact and having the life that you want. To learn more about our community and how we can help you, visit join purplecircle.com.