Noob School - Marty Osborn Turns the Tables: A Behind-the-Scenes Look at My Sales Journey

Episode Date: January 3, 2025

In this special episode of Noob School, the tables are turned. Instead of hosting, I’m in the hot seat, with Marty Osborn leading the conversation. We take a deep dive into my journey through the sales world, from my early days as a rookie to where I am now. Marty and I talk about the people, the challenges, and the key moments that have shaped my career over the years. Throughout the episode, we discuss some of the memorable experiences I’ve had, both the successes and the lessons learned from the missteps along the way. We also talk about the different roles I’ve played in sales, from being on the front lines to coaching others, and how my approach has evolved over time. It's a relaxed but insightful conversation about what it really takes to succeed in sales and business, and how adaptability and persistence have been key in my own career. Whether you’re just starting out in sales or you’ve been in the game for years, this episode offers a lot of real-world insights and lessons that you can apply. So, if you want to hear more about my sales experiences, the people I’ve worked with, and the mindset that’s helped me grow multiple businesses, this episode is for you. Get your sales in rhythm with The Sterling Method: https://SterlingSales.coI'm going to be sharing my secrets on all my social channels, but if you want them all at your fingertips, start with my book, Sales for Noobs: https://amzn.to/3tiaxsL Subscribe to our newsletter today: https://bit.ly/3Ned5kL #SalesTraining #B2BSales #SalesExcellence #SalesStrategy #BusinessGrowth #SalesLeadership #SalesSuccess #SalesCoaching #SalesSkills #SalesInnovation #SalesTips #SalesPerformance #SalesTransformation #SalesTeamDevelopment #SalesMotivation #SalesEnablement #SalesGoals #SalesExpertise #SalesInsights #SalesTrends

New School. Hi, welcome back to Noob School. Episode 137. And no, I am not John Sterling. I'm Marty Osborne. We got my sidekick in the seat over here, John Sterling. Hey, yo. What's going on, John?

Well, it's nice to be here. It's nice to be in the guest chair, you know, for a change where I can just relax and just answer questions. Well, it's good. I think, you know, words of wisdom always come out of your mouth. And so sometimes I think when you're asking the question, questions, we don't really get to know John. Yeah. And so today we're going to get to know John a little bit better.

Well, I'm excited. I'd like to get to know him better, too. To get started, I think one of the funniest things, you were just telling a story about one of your first job interviews in sales. Okay. So for all of you in the nubes out there, you know, wondering how you can become, you know, successful, don't despair if you make, let's say,

have a small indiscretion, you know, early in your career. So I was telling Marty, he was saying I ought to get this guy to come on the Noob School, very successful kind of EPSL's guy in town. I said, you know what? When I was just out of school, my dad got me an interview with this guy. And he said, well, John, the interview, the guy says, John, why don't we meet at Bojangles for breakfast at 7 o'clock on Wednesday morning? I'm like, I'll be fine, you know, it'll be fine.

So on Wednesday morning, I woke up at 10.30, and my mom was like jiggling my toe going, and get up, John, get up. So I had not only missed the appointment with this guy, I missed it by four hours. So that was not the only dumb thing I've done, but it just goes to show. I mean, nobody's perfect that if you screw up a little bit, just go find somebody else to talk to, right? Yeah. When we're young, we do some nutty things. Yeah.

And every one of them is recoverable. Yes, yes. And I think it's just to learn from that. And so, you know, one of the things in, I mean, episode 137, did you ever think you'd be doing 137 episodes? Heck no. Heck no. You know, I wrote this book during the lockdown years. And I was like, you know, I got to, I want to get this ideas about sales out into a book where people can read them.

and as soon as I finished the book, you know, some guy says, well, you don't need to do a podcast now. I'm like, oh, what? How do you do that? And so I figured I'll just try it. Yep. And it's been, it's been delightful.

I mean, it's been so much fun. I've enjoyed listening to the episodes. I've enjoyed being part of them. As you look back on those episodes, are there any of that just jump out at you, stick out at you or, you know, some lessons you learned that you didn't think you would learn? Well, one lesson I hear over and over again.

I heard it from Edwin McCain. You think about this guy who's this famous rock star, you know, and he's been interviewed by Letterman and Leno and all these people. And then the mayor, you know, Mayor Knox White, we think of him as being this great mayor and, you know, doing all these wonderful things for Greenville. And then Billy Campbell, you know, who's head of the Discovery. channel and all the cool things he got to do with Lance Armstrong and, you know, the biking and

stuff all around. All that stuff is really cool. But you got to, you got to back it up about 20 years to when they got started and say, what did they have to do to make that happen? You don't get to be mayor out of college. No, no. Right? And when Edwin started out, you know, he was working for a pizza, you know, where he could get maybe a pizza at the end of his shift. And then, you know, Billy was a little different in that he went high qualification. You know, he went to Harvard. He went to Harvard Business School. He did a year in China. Yeah. So, you know, he's kind of the kind of person that they look at to run these entertainment companies.

So he put himself in position. But the idea that, you know, you pick something that you like. Everyone loves music, Knox loves Greenville and, you know, being a mayor. Serving people. serving people. And Billy wanted to kind of get to the big time of the entertainment world. And they put a plan in place to get there and just pecked away at it until they're there. Yeah.

And I see that almost with everyone I talk to that's successful, they've had that same thing. Very few people have like, I tried this, then I tried this, and I tried this, then I got lucky. It doesn't happen that way. You know, sometimes people say they get lucky, but they made their own luck. Right. Right. They tried things and they put themselves into positions. I heard one thing, I heard a story about Gary Player, and he was out on the golf course

and he was practicing swinging. The guy comes up and says, God, I'd love to have a swing like you. And he goes, no, you don't. You know, 10,000 balls. I hit 1,000 in the morning to my hands bleed and then I do it again. And so. Just hit it perfect. But it's that work.

It's that thing behind it. And so it sounds like that's sort of the lessons you kept seeing. was, like you said, the early days of anybody's career. Yeah, you know, picking the right thing and then getting the network established in that area, getting your learning what you're doing, making your contacts, and then not being too big of a hurry, because nobody does it in year one or year two.

And I know just from our relationship going, you know, way back, we've been friends for a long time, you know, you pick the computer industry, you know, pretty much, right out of school and you went through several different places. One didn't work like you want and try another one and it worked pretty good. Then try another one it worked, I think, real good. And then you finally got to do your own thing and you crushed it.

But if you tried your own thing right out of school, you know, you wouldn't have been ready. Not only were you ready, but you had the contacts to help you and the company and just had all the stuff set up to make it work. Yeah. I think sometimes you also have the peace of mind. Yeah. Because, you know, the funny part is you always learn you're going to get kicked in the teeth. Yeah. And I think when we're young, we don't think we're going to get kicked in the teeth.

Right. And we do and we don't know how to react. Right. Are there any great stories of you getting kicked in the teeth, you know, as a salesperson or where a deal just went awry? Well, I think, you know, the biggest kick in the teeth that we had to deal with is a business. was when we had we had built a great business we were making money

everything was going with global business public company everything was good and we had a whistleblower you know just kind of make something up about a tiny office in China I don't know why

I can't speculate on that but someone said you know something's wrong with this office and the accounting's wrong or something so long story short you know our auditory had to spend an order amount of time and money trying to audit this little office in China. It was less than 1% of our revenue. And in the course of doing that, it just took so long that they couldn't verify our numbers,

meaning we couldn't report as a public company. Right. So eventually, they take you off of NASDAQ and make you a pink sheet company, which sounds pretty bad. And, you know, it was one of those things where, you know, Really, there's two paths. One is I give up. Right. I can't make, you know, $30 million for the sales this quarter to Fortune 500 companies.

If we're on the Pinch sheets. And the other is, we're just going to pretend like it didn't happen. Everything's fine. Everyone's got a number to make, and we're going to make it come hell or high water. Right. And that's what we did. And it turned out not to be that big of a deal. No.

The damn customer, you know what they cared about? Not where we're listed. can we help them solve their problem, right? Yeah. Was the pink sheet or being a publicly traded company going to help them solve their problem? No, so it was one of those things that, you know, I think we handle it correctly,

and probably the reason to handle it correctly was the other option was no good. We lose for sure if we do that. So we kind of picked the path that had a chance to help us. Right. So what are the things you've always talked about and always ask people, what's your favorite word?

And we've talked about your favorite word. Again, is there any words out there that somebody came up that you thought was unique or surprised you or just kind of different? I don't remember them. I've not been completely surprised by anybody. I mean, mine's absolutely. And it's partly because I've heard many sales reps and people, you know, when they say, Are you going to have a great year?

Well, I'm going to try to. Absolutely. I think I will. You know, everything goes well. No, no, no. Absolutely. Absolutely. Yeah.

So what we tell ourselves very often becomes the truth. And I think when you have an absolutely mentality, much more likely to get what you want. Yeah, I love that. Do you think our product can solve their problem? Absolutely. Like, absolutely. Because I've been in situations where somebody's sort of asked that question and the person's like, well, you know, and it's like they start trying to couch it like, then why are you doing this? If you don't believe that your product can solve their, I don't know if I remember you saying, I love that.

Absolutely. Well, we loved it so much in Marty and sales that we had tattoos made up. Really? Yeah. And we would, everyone had a tattoo in sales on their arm and said, data stream absolutely. Absolutely. So what are the things as we get into selling, and you've talked with a lot of people, and I think one of the other themes that I always hear is trust, right? It's people buy from people they like and they trust. What are ways that you really feel like a salesperson builds that trust?

Because it seems like, you know, we talked about sort of jab, jab, right hook, you know, that Gary Vanderchuk said is, we have to earn the right to hook and too many salespeople just want to go right into the pitch. And kind of curious, as you've been working with people, your thoughts on gaining trust, gaining, you know, a repertoire or, you know, a relationship with that person. Talk about that. Well, there's a couple things. I mean, the first thing is not to do. Don't tell them you want to be a trusted advisor.

I want to earn your trust, Marty. You know, it sounds so salesy. You don't want to sound sales. you don't want to bring it up. What you do want to do is at the appropriate time, if they say, or Marty, tell me why I should buy it from you. You want to honestly say, I'm honestly not sure you should. I don't know yet.

That's what I'm here for, to see if we can help you. And be honest about it, but tell them the truth, and they'll be like, I've never heard that before, you know? So that's one thing is to kind of reverse it and be honest to say, we don't know if we're a good match or not yet. And another one is at some point in the conversation, again, you use your tone of voice, not just words, but to say, you know, there's something, there's something sensitive I need to bring up. Right. I just want to get your permission.

You know, we need to talk about the money part. And if we don't do it, now, you know, we might be wasting your time. Yeah. You know, or something like that where, you know, you're not just being all smiley and insane. and everything's rosy. It's like you stop them and have a serious discussion about something. You're really good at that. I've seen you do it many times. But I think that's how you earn their trust. They say, I'm dealing with a person, an honest person, a brave person, not just a salesperson. Yeah, I think one of the things, it was funny. I learned a long time ago, they say the key to a good joke is to break the pattern.

So, A, B, D. You break the pattern, and it breaks in our mind. And so to me, what you just said, like about, is it okay if we talk about something difficult? They're not used to that. So you break this pattern of a salesperson's always selling, always selling, always pushing. And when you ask permission to handle a difficult question, they're like, wow. What do we have here? What do we have here? I'm kind of intrigued by this.

And, you know, I've always said I love the word no. The power of no, like when you give somebody the no chip, you know, and you say, look, it's okay if this is not the right thing for you. Just tell me no, and I'll stop. Yeah. And their defense is dropping. And they're like, I've never heard that before. Right.

And so, yeah, I love that kind of relationship thing. Yeah. Yeah. So just by all means do anything other than being a traditional salesperson. Yeah. And you've been out there. You've been promoting the book. Writing a book, we always have our favorite chapter.

I'm kind of curious. Do you have a favorite chapter or a favorite chapter or a favorite chapter? or a piece in the book that just speaks to it. I mean, the weirdest part, I think it's chapter two. It's about how a salesperson needs to take care of themselves first. Like, I have not seen one single person who's become like really successful, built a company, you know, done real well in sales, sells a million dollars a year, you know, whatever or makes a million dollars a year.

They don't take care of themselves. You know, the idea of the good. time Charlie who's like overweight drinks too much, you know, comes in late, you know, smells like fried chicken, you know, that's fun for a year too. But if you want to be that person who's going to be leading something like you did, no one's going to fall a good time, Charlie. Right. I'm not going to come with him, you know. And so being doing exercise, being in somewhat good shape, you know, good sleep, kind of being ready for action every day for a long period of time is kind of a prerequisite for success because all the other tips and tricks in there about getting early and make so many calls

and how to negotiate, it's not relevant if you don't have your act together. I love that. That is. I mean, I think it's taking care of yourself being that right person because if you're out all night, Remember, I think I laughed at my book called Night Jerry and Morning Jerry. You know, Night Marty goes out partying too much and he hurts Morning Marty. Yeah. So Morning Marty is not very good so he can't sell.

It doesn't make money. And then he hurts Night Jerry because Night Jerry doesn't have any money. Any money, yeah. And so I think it kind of goes to that taking care of yourself to be able to do the things you really want to do. Yeah. Get your act together. Yeah. Absolutely.

What other things, I guess, just I love that. just around yourself, any other, I guess, kind of words of wisdom that you've, you know, as you've been coaching thousands and thousands of salespeople. I think it really, I don't know if it's the next chapter. It might be chapter three. I think it's test yourself before you wreck yourself. I think it's the name of the chapter. But it's really to understand, to try to figure out who you are.

What are your natural talents? Where should you be? And I'll give you a good story. I mean, everyone looks at. Jeff Bezos now is being, you know, he's one of the richest people in the world, built Amazon. That's pretty damn cool. But if you back up, you know, to when he was younger, he was obviously one of the smart kids in school, right?

Yeah. He, you know, probably the high SAT, went to Princeton. He was majoring in physics. And he wanted to be one of the best physics people in the world. Do you know what happened? He probably flunked out. He figured out. Well, he was trying, right?

He was trying. But he figured out. There's like 40 people in his class, and he's like number 37. He's like, there's just people here that were born with something in their brain that made him a lot more clever at physics than him. They can solve the problem in like 30 minutes. He'd do it for three days. So what are you going to do? You're going to cry over spilled milk.

You're going to just accept it. He said, this is probably not the best fit for me. And he switched over to computer science, okay, where he did. pretty well. And he went from computer science, and he made another great decision, which was, I'm going to go to work for an investment bank that has a small specialty in Internet investments. And that's where he got his job. Dang.

And so he was paid to look all day for what's going to be going on with the Internet, and that's where he had the idea for Amazon. Dang. Isn't that wild? That is. It's all smart, strategic thinking. And I think one of the things is, as individuals, you know, we have to be open to what the universe is saying to us. Yes.

You know, I think sometimes we just, we have that deliberate. I'm going to get, yes. I'm going to get that deal. No matter what. No matter what, you know, persevere, persevere, persevere. Yeah. And we just miss things. And so I think that's a great story.

I want to change gears a little bit. But sort of the same thing around education. You're an athlete. And I thought about this that it kind of cracked me up is if you had a child and you went to the coach and they were going to play basketball and the coach said, you know what? Your kid's really tall. He's really good. We don't need to practice. We're just going to play games.

What would you do? I'd probably, you know, try to get my kid on another team. Another team, right? You know, but we're talking about practice. And I, you know, the funny thing about it is and what I love about Noob School and everything is, the real winners are the ones that practice, that they go to practice to be better, that they don't just show up, but for some reason in sales and leadership and whatever, we think once we become a pro, we just show up.

We don't practice. And I'm always amazed. I mean, your thoughts on that. Yeah, I agree with you 100%. I think salespeople should have some commitment to training every week, you know, two to four hours a week. that ought to be split up between sales training and I would call it customer training. Where you're learning kind of how it works with the customer.

So, and I must admit, I mean, we had a lot of training with our salespeople up front to get them ready. And then once they graduated, a lot of times we just leave them alone after that. Yeah, yeah. And then we might do training for, like, user group or sales meetings and stuff. But now I think, like, you need training every week. And training doesn't have to be somebody training you, right? It has to come from within. It's reading podcast, learning lessons.

Like, people just seem to want to show up. Yeah. And I think that really is, as I look through probably most of your interviews and so forth, everyone's a professional and everyone really hones their craft. Like how much time, how many hours you think Edwin McCain spent practicing. Yeah, so many. So many. So many. I totally agree. And that's something that's very common with the people that usually sit in this

chair that are successful people. It's all, they read everything. They read, read, read, always trying to learn, you know, more about what they're doing. And they just do it forever. Yeah. And the people that don't, Marty, I would just call them middlers. Yeah. You know, they're just, they're not horrible, but they're just kind of kind of stay right. You stay right there. And, you know, the solution is pretty simple. I mean, it's just, I mean, the most common characteristic of the most successful people in the world is they read. So just read.

Just read. Yeah. I mean, I always left in one of the chapters in my book is it was going to be, you know, readers are leaders. And then somebody says, well, I like audio books. So I was like, okay, leaders are learners. You know, I had to kind of, I kind of had to flip that script. But again, I think it's just over and over again when you're in Noob School, when you're in sales, that educational process never stops. And the best ones are, they never stop.

They never do that. And, you know, I like to ask a question to people is, would you pick yourself? Yeah. You know, remember that commercial? You ever see that? What was the insurance commercial? were they picking a basketball team and Barclay's in line with everybody else? The kid goes, I'll pick Barclay.

I'll pick Barclay, yeah. You know, would you pick yourself? And I think that's another thing people need to do. Well, you know, the Kobe Bryant story, you know, when he broke his day down and he would, people would be coming down for breakfast from the hotel, his teammates, and he'd be coming from the gym, already having a full workout.

And then, you know, he would do that, you know, two or three times a day. And he just did the math. And he's like, I'm going to end up practicing more, you know, almost twice as much as the other people. So I'm going to be better than them. And so the weird thing about that is not only did he practice and get better than everyone, but he thought he should be better.

And that helped him be better. And they shot, they thought he should be better. And that helped him better too. They're like, well, of course, he practices more than us, you know. Yeah, you do that. thousand hour rules, you're going to be great. And I, you know, we talked about this in one of the episodes when we had Johnny Bophilios on. And to this day, he still thinks about this is when you would record people. And you know how hard that is to record yourself and then to be graded, right?

And nobody's going to say, John, I want to do it more. But the more you did it, you're like, you learn so much about it. But our first instinct in our brain is, I'm not doing that. I know, I know. There was one moment. We talk about the Greg Gardner moment with the tape. Yeah. I told you that one? Yeah. Okay.

So Greg was one of my favorite all-time salespeople and still a good friend today. But I was making him do a tape. And he was making it with this girl named Maggie. So she would call and he would call and they would make the tape. And so they come to my office and bring me their tapes, you know. I put his in, hit play. And it's like, this is, he goes, this is so stupid.

He goes, I can't believe he's making me do this. This is so stupid. And she goes, Greg, just make the call. John has good intentions. He's trying to help us. I mean, I looked at Greg. He looked at me. I just started laughing so hard.

I was crying. And we became really good friends at that moment. But, you know, I can see why people think it's stupid. No fun. It's hard. Yeah. I mean, it's hard to hear yourself, and it's hard in practice. this like Edwin listening to himself at early days it's hard yeah well you know it's weird is we

one of the tips that I always tell people and I think I put it in here is you can hire a really experienced consultant for a day come and look at your what you're doing and give you their ideas and it can be the best money you've ever spent yep like we had a guy come in and look at our sales organization we had like seven people and he told me that I ought to start listening to him. He's like, you might find that that's the reason some of them make quota and some don't, right? And so I started, and one of them was just, I mean, it was so, let's just say there was a lot of opportunity to get better. People would just ramble, they would talk too much, they would say the same words over and over again,

they wouldn't cover everything in the call guide, I mean, just simple things. Yeah. And so we would fix those and get them where they could just literally just work their way down like they're supposed to. and it made everyone's life easier. Yeah. You know, one of the things that I learned, and I learned this early on through some of the work was writing my own scripts,

and I actually took this in negotiation when I was actually working our deal for our company before every call, I would write a page of exactly the phone call. Yeah. And then the phone call would happen, and my business partner would be like, how'd you know that was going to happen?

Right. I go, I didn't. But I followed a script in my phone call. my mind, psychologically, I followed that process, and I was in control where the person on the other end didn't know where it was going and they weren't. And so to me, what I loved about that story was it helped people develop a process and a mental hack that just keeps them on track. They know where they're going as opposed to, oh, they said this. I don't know what to say next. Yeah. I mean, having a guide, you know, I call it a call guide, but just having a guide of where

you want things to go. We want to say hello and be polite. We want to agree on the agenda. We want to ask them what the problem is. Explain it to me. And then try to figure out if we can help them or not. I mean, it's more complicated than that, but basically there's a flow to it.

Whereas without that guide, you might call up and just say, well, hey, Marty, so how's Clemson doing? You go into Texas? You know, blah, blah, blah. All of a sudden, you're all over the place. Call's over. And I would say, how is the call?

And this were up we go, it went great. Marty's a great guy. He's going to Texas. He's a big Clemson fan. So what's going to happen next? I said I'd call him in a couple of weeks. Hopefully Clubson wins. Yeah.

So, you know, there's a lot to the basics of making that kind of stuff. And most of the companies that I work with, not all of them, but most of them just need some of those basics to help turn their small sales team into something that they can predictably grow. Yeah. And again, my word has always been intentional

like in the call and it was funny we used to, and this is sort of a tip for your listeners because we get somebody on the phone and you know,

think about any salesperson who calls you, what's going through your mind? Get off the call. Yeah. Dang it, I can't believe I answered this phone call. It's cheesy.

Yeah. Oh, crap. And so we would just be like, hey, John, this is Marty Osborne. Do you mind if I borrow a minute of your time? And you'd be like, no, I really don't have time. I said, well, then can I steal it?

And I get that, laugh, laugh. And you get the laugh and they're like, okay, let's do it, right? And so anytime we can kind of flip the script. So, all right, well, we're probably going to wind down here with you and I. I'll talk forever. But I kind of want to go back and just, I'm kind of curious, a favorite John Sterling childhood memory. Like, what's a favorite memory of yours?

One time, I used to go fishing with my dad a lot when I was. was a kid. And I had made a homemade stringer, okay? You know, I thought it was real cool, you know. And so I had this homemade stringer made out of a string and had a little thing on the end of it. And we had, it was the mother load day. We had crushed it. We had caught so many fish, you know, bluegill and bass and all this stuff.

And so, you know, we would put the fish on the stringer and stick it back in the, you know, the side of the deal there. And so we're trying to fish for some more. and I look out in the water and all the fish are swimming away in tandem like they're a school of fish still on the stringer yeah they'd pull out from the shore

and I just had this moment where I just like it was like nine years old and just so crying like a little baby for like five seconds and then dove in dove in the water went out there and grabbed that stringer

and brought it back And you're like, there it is. There it is. What'd your dad say to you? He was like, yeah, you know, that's the way. It's the way, you know. And I think that's a good, a good memory or a good lesson for life. Is, you know, are you going to dive in and grab those fish?

You're going to cry about it. You know, what's you're going to do? I love it because I think that's John. I think that's you, that in your life you love doing things with people. You love one-on-one and that sometimes things go awry. And your reaction is, dive in and get them. Dove it and get them. So I hope you enjoyed this session.

I've enjoyed being on this side of it. You did a really good job. Well, you're a great side-ticking. Is this like Leno taking over for Carson kind of deal? It might be. If you ever, you know, if you're sick or you have a day off, I'll be glad to sit in the chair. I'm not leaving for at least another two years. Well, thank you, Marty.

Thank you. And it's been great. I hope everybody had fun. and we'll see you again. All right, thank you. Thank you. All right. Thank you, buddy.

Thanks, John. Good.