The Advanced Selling Podcast
Bill Caskey and Bryan Neale deliver practical, no-nonsense sales training through their signature blend of humor, real-world insights, and actionable frameworks. Each episode tackles the challenges you face daily: prospecting, overcoming buyer resistance, pricing strategies, cold calling, deal coaching, and building long-term client relationships.
Whether you're a sales professional, manager, or leader, you'll discover how to shift your mindset, leverage your natural talents, and create sustainable sales success. From mastering sales communication and handling RFPs to understanding buyer psychology and effective positioning, Bill and Bryan cover everything that actually works in modern B2B sales.
The Advanced Selling Podcast
Lessons We've Learned From Those We've Lost
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Every person you've worked with has a story you probably never asked about — and sometimes you don't find out until it's too late.
In Part 2 of their series on the people of sales, Bill and Bryan honor a handful of people who shaped their careers — a neighbor and airline pilot, a mentor who connected without ego, a customer who never delayed a decision, and a prospect Bryan gave up on too soon.
Each story carries a lesson you can use this week: ask people about their actual lives, don't wait to reconnect with old friends, decide fast, and don't give up on a prospect after just one or two tries.
It's the 20th anniversary of the show, and Bill and Bryan want to hear from you — send a short voice memo to listener@advancedsellingpodcast.com for their September anniversary celebration.
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Welcome back, one and all, to the Advanced Silling Podcast, the longest running sales training podcast podcast history. We are celebrating our 20th year in the podcast space in September. If you have a well, welcome, Brian.
SPEAKER_01That's right. Thank you, Bill.
SPEAKER_00This is our podcast, as I said. This is our. That's right. Uh if you have a story about the podcast and how maybe it's uh affected you positively or negatively, put you in the Insane Asylum because of our upfront three-minute rant, um, let us know. Send us uh an audio to listener at advanced selling podcast.com. You could you could do video, but audio is probably easier for everybody. So um just let us know where you listen, how long you've been listening, what you've taken from it. Um we've we we get all sorts of emails from people who say, you know what, I I led the I led my team last year in sales, and I was seventh year before, and I attribute a lot of it to what I learned on the yeah. Sometimes we get those those kinds of things all the time. So let's document those, send them to us, listener advanced light podcasts. We'll put in the show notes the link.
SPEAKER_01Yeah, we'll yeah, we'll do that. We'd love to hear from you. We just want to hear who all's out there and listening to all that stuff. We know you're out there, so we might start DMing you since we're playing our own party. We might show up just you gotta decide who's got who's yeah, who's gonna decide what we're gonna get on the cake? We should get a cake from Taylor's bakery, shouldn't we? We can't oh that would be good. I love it.
SPEAKER_00Like with the logo on the cake. Oh, yeah, I love it. Oh, that's a good idea. I could come down there, we could have a little bit live, right?
SPEAKER_01Oh, yeah. How about it?
SPEAKER_00That's turning into something now.
SPEAKER_01It's a thing. Now it's a thing. Um nobody else will plan once again, but since we're on um Indiana hometown nostalgia, I uh with uh I think there were six of my best friends from we've been friends since we were uh 13 or 12, like seventh grade. And a few of their wives and one of Guy Brown's daughter, and then one of my buddies, my best best friend, has been friends of him since we were 10. Uh, they all came in Indianapolis and we went to go see one of our iconic, historic, best music performers that that someone that just defines our life growing up in Indiana, and also in our our wheelhouse of our age, uh John Mellenkamp. And we were so impressed with how great his show was. Really? Uh he has been he's 74, I think. Is he really? And he played 74. He didn't try to play 30, and he could still sing. Yeah. And he sang what he could sing. He didn't try, he didn't press upper notes, he didn't scream when he you would normally scream back when he was younger. Crowd, you know, he played, I think, two hours 40 minutes. He played 26 songs. I knew 25 of them. Wow sing long, and it was just a very nostalgic night. And was that a Ruoth? That was at Ruof, yeah. Which we outdoor nice outdoor beautiful night. So, one, if you're a remote you music fan, you're like, Hey, John Mellencamp's coming through, you're like, ah, no, thanks. Go see him. He's great. Uh, now he he was he took for 20 years, he was been doing kind of acoustic. His music got a little off for me personally, but he's all hits uh nothing but this is for exactly 26 hits. Oh my god, that that's that's impressive because usually they don't they don't do that. No, and it was just absolutely fantastic. So yeah, and uh another reminder also, or just a little nudge for you. If you have friends from childhood or junior high or high school, don't put off getting together as you is, you know. I don't care how old you are if you're listening, you're 24, you're just out of college, get get in touch with your junior high and high school friends and do the same thing when you're 75, you know.
SPEAKER_00Stop with this. I don't have time BS. Oh, right. Uh my come on. It will inspire you. I mean, uh, it will it will just inspire you to re to go back to those times where you didn't have a whole lot of responsibility and no money, but no responsibility. And those were the those were great free times. So true. Yeah, it's good. Well, we talked uh last week we started this uh what we think is at least a two-part series, who knows? Uh, because it is our show, and we'll decide how many how long the series is. But we talked about the people of sales and the people that we've met over the years, and the people you've probably met, and trying to derive some lessons from whether they treated us well or not, and how we how we have tended to judge people and have been wrong. Um, and you just mentioned the the whole uh going back in time and grabbing your people. I I've got a story that a friend of mine, a neighbor, you you might know Jay, Jay Strauk. He was the airline pilot. He was American Airlines, and he flew the 787s to China, Beijing. And he he just retired about five years ago. And he was a great guy, big golfer, loved golf, just a just a really good. He's a man, he was just a man's man. He's really a cool dude. Well, he died two weeks ago.
SPEAKER_01Oh man.
SPEAKER_00Yeah, and he had he retired five years ago, worked all his life and looking forward to playing golf, and got some kind of weird cancer, and he fought it. He played golf for two years and fought this damn thing for three years and finally succumbed. But we went to the uh it's one reason I had to cancel the last recording, we went to his funeral service, and funeral services are great because you learn about people the things that you didn't know about them when they were alive. And I thought, what a shame. What a shame that what a shame that we didn't know what kind of a human being you know we live next to for 25 years. But but you don't ever have those conversations. Instead, you're talking about who do you have cut your grass? You know, who's you know, all those stupid. And and when I started to find out you went to the Air Force Academy and he bailed out, you know, in a jet that was crashing into a mountain. I mean, all these things, it's like, why did I never know that? Well, I know why you didn't know it, Bill, because you never sat down and asked him. You never sat down and and asked him about his life and his life in the military at the Air Force. He flew airlines for flew airplanes for 30 years or whatever. Had to have been some harrowing moments. And that's a lesson for me that you know we we have to learn about people because everybody has a story, and you have it, and we all have stories, and you know, the more we're in conversation with people at that level, I think they're it just makes life richer. That's awesome.
SPEAKER_01That's awesome. Well, I'm glad you uh uh said that. That's a good thing to say, that's a good thing for everyone to hear um because it's the truth, and everyone's a moment away from making a different decision on that subject. All you have to do is pick up a phone and call somebody. That's all you got to do, or invite them to something, or come over or sit down with them, or doesn't matter what it is, and just breathe on that. That's really, really good.
SPEAKER_00We just we just we're we're busy putting out fires and yeah, tending to our external BS of our lives, and we we don't stop and say, you know, we haven't seen the Smith family in a while. Let's invite them over for dinner. Yes, or let's let's go to dinner, or let's, you know, whatever. Go to a movie. You know, movies are bad because you really don't talk much in movies, you just sit next to somebody. But unless you well, you get older people talk, people like that.
SPEAKER_01What do you say? What's what's he saying? Okay, where is she going?
SPEAKER_00It's funny, isn't it? Or my or my brother-in-law will say, Why did he go into that bully? It's like because of script.
SPEAKER_01It's the writer, that's the writer. That's what it called. That was what the blocking called for for him to walk through that door. Following order, that's all he was doing. Oh, geez. Uh well, I'm gonna um go and talk about another mutual friend of ours that I know you know, who is also passed away, and that is Bob Porn. To honor him, we talk about people you've come across in sales. So, this is a this is a double whammy story for me. Bob Poeman was partners with a longtime friend, one of your first clients, Dave Harding. Is that correct? The first first client ever. Yeah, uh, and so I, when I started working for you, got to meet uh these guys, and I was incredibly intimidated by them when I knew the size of their business and who they were, and just their names in town, and just you know, very, very just intimidated. I was like, Oh my gosh, I can't believe I'm like actually in business close to these guys. And I struck up a bit of a business mentorship with Bob. Um it sort of just evolved. And uh the things that that guy taught me, um, and and what I loved about it, he taught me by doing, not by telling me what to do. He taught me by showing me, not by telling me what to do. And the biggest thing he taught me was the uh power of friends helping friends and connecting and networking with people in a market. And he sat down with me at a sushi joint called Kona Jacks one day, and he's like, Okay, I said Bob, I I just I'm not catching on to this networking. Like, I know people, and he's like, Okay, where are you hanging? You ask him all these questions. He's like, Where do you go to church? Because he knew I was Catholic. I'm like, Immaculate Heart. You don't have any business owners who are to go to Immaculate Heart. I'm like, Yeah, he's like, You don't think they want to work with guys that go to Immaculate Heart? It's like you know, a thing. So I made this big list. He's like, Who else you want to meet? I got this big list and gave it to him on a Saturday morning. I'm sitting there, all of a sudden my email starts peeing, and it is Bob connecting me to like 30 people in our town who were big, you know, in our world were big names, like big business people. I'm like, oh my god. Ended up having lunch with several of them. Um and I just thought, man, that's it. And what Bob taught me there was he was giving, he had lots of fish to fry, that's right, and to help some 27-year-old punk kid trying to build up sales training practice, but he didn't care. He did it on Saturday morning and he didn't have any ego around it, and he just did it to help, and that's how the world worked. And Ben that flipped a switch for me, and I've done everything I could since that moment to emulate that behavior and him, and not the get not the asking part, oh good asking, but also just trying to be someone that brings people together with no ego as best I can. Uh Lou Garrett's disease, I believe ALS passed away. Yeah, yeah, and man, what a great humor he's gone to.
SPEAKER_00You know, I worked for his dad at McAllister, uh caterpillar dealer, back before I started this business. So I didn't know uh Bob Jr. was just I knew I knew Bob Poorman Sr. had a son. But anyway, you know, one thing I I remember about Bob was, and it's not necessarily meant to be a tribute to Bob, but again, lessons we learn from people. And I remember we uh I went in to give him a proposal. I don't know if you were there or Brooke or somebody, and we were talking, and uh he said, What do you got for me? And we kind of laid it out. And he goes, uh, okay. And it was it was a lot more than what we had done in the past, if I remember right. And uh he goes, Okay, as you guys look at this, is there any reason that I should not do this? Like uh what a question. Is there any the customer says, Is there any reason that that I shouldn't do this? And I said, I don't think there's any reason. He goes, Okay, let's do it. He signed it and we were done. I mean, this was a 10-minute meeting, but what that taught me was he decision, fast action, yes, make decisions, not just because he said yes to us, but he I'm sure he did that everywhere, not just us. So good. Um, and I thought, how many times do we just put off a decision? Well, we'll think about it. Well, we'll think about well, I gotta think about another year and then I'll do something. Then he was like five minutes, there's no reason I shouldn't do it. Okay, let's do it. Next, what's next? And that's the way he built his business, and and that's how you build relationships. And do you think we didn't go the extra mile for him the whole time? You did, I did. Yeah, because of just the nature of him.
SPEAKER_01Yes, always a straight shooter. That's good. Got another one?
SPEAKER_00Um, I do have one that is a unusual one. Uh, back when I first started the business, I was making cold calls. And uh I I called on this radio station, called on a guy who owned this radio station, WBRI. It was a a religious Christian. Uh and I was just making cold calls because I was trying to fill this program. I can't remember what it was called, Breakfast Club or something. I was trying to fill this $2.95 a person. I mean, it was crazy cheap. Um, I think I worked with him for like a year, I don't know, for $2.97. It was it was an awful model. But I remember this guy, and I can't remember his name now, but I remember this guy, and and uh I could never get a hold of him. I tried and tried and finally I just gave up. I gave up quickly back in those days. I because I didn't like coal calling it. So what am I gonna do? Do this for six months, try to get a hold of him, but I gave up pretty quickly on him. And I had heard that he was experiencing some health issues, and so I think I gave up on him when I heard that because I thought, what, I'm not gonna battle that. He's got his own stuff. Well, he ended up dying uh of a heart, heart condition like a year later. And this might sound like ego and it's not meant to be, but I always think, well, what if I would have been able to go in and help help him oversee his sales team? Because that it was stressful. I mean, being in the media business in that time where there was a hundred radio stations, everybody's buying for the same advertising dollar. Could I have helped his team so that he could have maybe enjoyed another year of life or just relieve the stress? Because I'm sure he was stressed about the business. And could I have taught him something about detachment or about intention or about something that would just have relieved it? I'm not saying it would have cured heart disease, but and and I always think, you know, when you think you're when you give up on somebody, just give them a few more times. Just don't don't give up quite because sometimes people have, well, they always, everybody's stuff going on in their lives that prevent them from returning a cold call. But sometimes if you hit somebody just at the right moment, it might be the fifth call or the fifth outreach. You hit them at the time where they say, Yeah, you know what? I've been thinking about this. I need to do something. That's a great one so don't give up too early. Again, could you save a life? Probably not, but maybe you can make somebody's life a little more enjoyable. Try to find the guy.
SPEAKER_01I mean, not and he's not here anymore, but his name is very Yeah. Uh I I'm yeah. I'll try to find him. W B and I, what was it called? W A R I. Okay. Um find him. Uh okay, I have time for one more. Yeah, let's go. All right. I'm gonna say my co-owner of this podcast, Bill Kaske. Oh right. So you took a chance on me in 1997 after I had was bankrupt, and I was at the lowest point of my life. At that point, I've since been in some lower points, but at that point, that was as bad as it gets. And I'd have a pot to piss in, and you didn't have a big business to pay a big base salary that I was making a PNG or not even big or anything. But you would you agree to do a deal with me, and uh I'm um I was four months in and I didn't have anything going. And you you you probably don't know if you remember this, but you're like, look, dude, you're not gonna make it if you don't get an edge here. You gotta get an edge, like you need to get it at something, like get mad or get get something to or you're get snippy, you get a little snippy, and I love the training part of it. You let me do some classes, I was in love with that. I'm like, I gotta make this work, but that little talk you had, I'm like, dang it, I've got to save this thing because it's what I want to do, and it feels like what I'm on the planet to do. And uh, none of nothing that I've ever done since then would be possible if it wasn't for you. So I'm beyond grateful, man, um, for all that stuff. And then here we are 20 years later, still uh talking the microphone, still nobody, or maybe it's a nobody.
SPEAKER_00Is that is that what we're doing? But it's been awesome. What is our show though? 25 years. No, yeah. I mean, uh, you're you're welcome, and yeah, I I've not regretted for one second anything that's ever happened to us. Um so yeah, uh, I I just remember that when you came along, I I just liked you. I mean, you you and I you and I had a chemistry, I think, that I didn't want to lose too, because yeah, I'd had some people where I didn't have the chemistry. And so I think you know, we we all bring something to the table. Don't think that the only thing coming to the table is what the other person brings. And this is a good lesson for us in sales, too. It's like, you know, your company brings value, but you do too. Your personal brand, your reputation, your knowledge, your instincts, your voice, you bring a lot of value. And sometimes I think we we lose that and we start to think, well, it's the business, or well, it's my company's comp plan, and really it's all us. It just gets back to us, and that's what you realize and you fixed it, and here we are.
SPEAKER_01It's true. And you know who else doesn't see that to me? The managers and leaders sometimes. Yeah, back to that. You don't see that everyone there is teeth is teaching you something. You're learning something from every single interaction you're having with those people. Yeah, that was good. It's a lot of people. Good job.
SPEAKER_00Yeah, a lot of people there. Hopefully, we didn't offend anybody and throw people under the bus. We tried to pick deceased people so we could say their name and speak highly of them. That's right. That's right. You always are more highly spoken of in death than life. That'd be a lesson. All right, we'll see you next time. Bye. Bye.