Chris Caldwell (00:00:00)

Moving into selling and dealing with that rejection was extremely difficult for me to deal with and actually created enormous amounts of fear, anxiety, overwhelm, “not enoughness,” imposter syndrome. I mean, you name it, I had it. I did not realize how much harder it was going to be to sell myself. There are just things I need to be doing every single day to earn the right to be an entrepreneur.

John SmallMtn (00:00:25)

Yeah, earn the right.

Chris Caldwell (00:00:25)

Like to earn the right to have my own business, to have this freedom. Like there are very specific inputs that I have to do for myself in order to earn that privilege. Just always, always remember what selling is. And at its most core essence, selling is being able to present your product or service as the solution to get the individual from where they are to where they want to be in a way that makes the juice worth the squeeze.

John SmallMtn (00:00:56)

Welcome to another episode of Founders Growth. My name is John Hill, aka SmallMountain. I’m the founder of Adapted Growth. And today we have Chris Caldwell on the show. Chris Caldwell is the founder of Sell As You Are, which is a sales coaching and training company, and one of my favorite people to interact with on LinkedIn. And I just have liked his content for so long that I kind of wanted him to be on here, but I was unsure. And then we started talking about his background, and his background was really, really cool. And it kind of shows that you don’t have to start in sales to get good at sales. And this is important because since this is a show for founders, you might not have any sales background at all. And that doesn’t have to be a reason not to try. So Chris, thank you so much for coming on the show. I’m super excited to have you here. Can we start with talking about what you were doing before you moved into this lane of revenue and sales training and coaching?

Chris Caldwell (00:01:48)

Yeah, sure. So it’s great to be on here. I’m excited for this conversation. I was a high school history and government teacher. I did that for nine years in Cincinnati, Ohio, and then in Baltimore, Maryland. I taught a lot of different courses. I coached three different sports. And most importantly to me, at least, I was fortunate enough to facilitate many of the retreats. And so it was an awesome career. And then in the summers, I would wait tables at a crab house in Baltimore to keep myself busy. So that’s what I did for almost a decade before I left and got into sales.

John SmallMtn (00:02:26)

Mm-hmm. Was there a day—I love that moment of the awareness, right? And then we decide to go do something else. Were you burnt out as a teacher? Did someone kind of just place this in your lap? Or did you just wake up one day and you’re like, “Hey, I like talking to people. I could probably go be in sales.” How did that work for you?

Chris Caldwell (00:02:55)

Yeah, I think it was a variety of things. I had started to get a little burned out from all of it, but that wasn’t as much due to the environment I was in as it was due to my own programming and how I was burning myself out. And so I started suffering my own self-inflicted burnout without realizing I was the creator of the burnout. So that was certainly part of it.

The second part of it was financially—we were pregnant with our second child and the reality of the situation was if I continued to teach, I was going to be losing money. It was going to cost more money to send two of my kids to daycare than I would make. So I was literally going to lose money if I kept teaching. I could stay at home with the kids, but I never felt called to that path.

And then third, I wanted more freedom in my life, to be honest with you. Well, yeah, you have summers off and you have a nice long break for the holidays, but there are very few professional jobs that limit freedom as much as teaching does. When the bell would ring, I had to be in there and I had to be doing something very specific for a set amount of time. I was a grown adult being run by a noise coming out of the ceiling. And after a decade of that, I was just like, “You know what? I want something in which I can have more freedom—freedom in my day, freedom with my creativity, with what I want to do.” And there was a part of me that was always entrepreneurial. I started a couple of businesses on the side for fun at the time.

And I wanted to work in a merit-based role. So after working for a decade in a standardized role, where it didn’t matter how good I was or how good I wasn’t, I was getting paid the same, I wanted to try out a merit-based role in which the better I was, the more money I would make. And so I just decided to go for it. I didn’t know what I was doing when I quit my teaching job. I just quit my teaching job and figured I would figure something out. So yeah.

John SmallMtn (00:05:08)

Whoa. So you were feeling this pressure, right? Second kid on the way, seeing that it’s going to be costing you money to try to raise them and do it the right way. And you just put in notice? You weren’t like, “Okay, maybe sales?” Was it even that clear? Or was it like, “I just got to do something else and I don’t know what it is, but I want to go try”? That’s fascinating. Whoa.

Chris Caldwell (00:05:19)

Yeah, I just quit. And so it was coming up on that time, it was the spring season. Usually you want your teachers to put in notice by February or March that they’re not coming back. I sprung it on them a little bit, but around the April or May timeframe, I told them that I wasn’t going to come back. And it was really shocking to everyone because I loved teaching. I loved the boys—it was an all-boys school. I loved everything about it, at least on the surface from what people saw. So it was really surprising to many. But yeah, I just quit and I figured if I can, I’ll find a job doing something and from there I can learn. I just wanted to find where I could go where I could learn the most, and that was like my North Star in the job search.

John SmallMtn (00:06:20)

Fascinating transition. Okay, so where did you go? Where was that first sales role?

Chris Caldwell (00:06:29)

Yeah, so my first sales role was at Sandler Training. I was hired to do outbound and to sell people into the training programs, and my colleagues would then run the training programs. So I was, for a period of time, just a full-blown outbound seller for Sandler Training, the office in Towson, Maryland, which is right down the road from the international HQ.

John SmallMtn (00:06:58)

Wow, yeah. Absolutely.

Chris Caldwell (00:06:58)

Yeah, because David Sandler is from Baltimore. So that was my first job. And it was between that and Dale Carnegie Training, which had also offered me a job to do a dual track selling and learning how to be a Dale Carnegie trainer. Going back to that idea of freedom, the Sandler opportunity offered me more freedom. And there was also a gentleman there who said he would be my mentor if I chose to work there. He was David Sandler’s fifth employee, a guy named Rush Burkhart. He actually invented the upfront contract with David Sandler way back in the day.

Yeah, very cool, right? And so he told me that if I worked there, he would teach me everything he knew. He was partially retired and just had a book of business that he was managing. And so I was like, “Hell yeah, let’s do it.”

John SmallMtn (00:07:33)

Wild. That’s crazy. What a cool—I did not—I know a lot of Sandler trainers, spent a lot of time in that framework as well. I did not know that though, that’s flooring. Okay. Wow.

Interesting. So what I would like to talk about for just a second—I’m obsessed with overlap, right? So I’m curious, when you started there and you’re just doing outbound and trying to figure it out and everything, what helped you from your teaching background, or did anything map over that helped you in those early days? Because in the beginning, there’s blind spots and fear and rejection and all these things that are tied to our personality and our self-limiting beliefs and everything. Did anything help from your teaching background or coaching background in those early days? Because people don’t talk about it, but it’s a lot to push through that initial phase and to get really honest with yourself.

Chris Caldwell (00:08:51)

Yeah, you know, I think that I had a few things working for me, but many more things working against me. One of the few things working for me was time blocking. Because growing up—or not growing up, but for the first decade of my career—I was a teacher, in which everything was time blocked. My classes were at nine o’clock, 10 o’clock, so I didn’t have a choice; I had to be in there. And so that was helpful in that I built up that discipline of going into the classroom and teaching even when I didn’t feel like it, or when I was really tired, or when I just didn’t have it that day. And so that built up like a callus in me to be able to go do it even when I didn’t feel like it. So that was helpful.

If I can be honest with you, my 10 years of teaching set me up for immense amounts of failure in sales. Personally, this is just my personal experience with it. And that’s because I had an enormous need for approval: to be liked, to be accepted, to be seen and heard, to feel like I belonged, to feel significant—like all these different human needs. I had them very strong in my wiring, which is probably one of the reasons I chose to be a teacher in the first place. That was a place in which, for 10 years, while the paychecks weren’t huge, I was getting my emotional needs met in a wonderful way.

And then moving into selling and doing 100 to 150 cold calls every day and dealing with that rejection was so dramatically 180 degrees from what I had been doing for the last decade that it was extremely difficult for me to deal with. It actually created enormous amounts of fear, anxiety, overwhelm, “not enoughness,” imposter syndrome. I mean, you name it, I had it. And it was very, very hard for me.

John SmallMtn (00:10:52)

I mean, I had all that in the role before I got to work with my business partner. It was my first field role and I was selling to surgeons. I didn’t even have a big enough market to where I could really even go for the “no” or do any of these mantras that are so popular. I was just so fearful and nervous. I would pull up in front of offices and not even have the resilience to walk in. I’d be changing the apps on my home screen and stuff like this.

Chris Caldwell (00:11:21)

Yep, I feel that.

John SmallMtn (00:11:22)

And it feels really justified right there in the moment, you know? And that’s why avoidance and procrastination are such dangerous things, right?

Okay, so when you’re in there and you’re grinding and you have this mentor—and Sandler, I think, has a lot of value for a lot of people—did you have a moment where you were like, “I got it. I’m going to be okay”?

Chris Caldwell (00:11:50)

Yeah, I did. It started, I think, when I was able to consistently make the calls no matter how I felt. That’s when I realized I was going to be okay. And then I closed a couple of deals and brought in a couple of clients. I was full commission, and as I mentioned, my wife was pregnant with our second, so she was quitting her job. And so I was a teacher, had no savings, I hadn’t been making any money, so there was an immense amount of pressure. But after I closed my first couple of clients and got them in and started seeing their results and how much they were loving it, that’s when I began to realize like, “Okay, yeah, I can do this.”

And really, it took it to another level when I was able to get up in front of the room and start doing the training, because teaching is my gift. Teaching is my thing; that’s what I love to do. I had had my Malcolm Gladwell 10,000 hours. And so I was unique in that there aren’t a lot of sales trainers who have a master’s in pedagogy, and I in fact did. And so once I got up in front of the room and could be a teacher again, then I started to feel much more confident, like, “Okay, yeah, I got this. I can do this.”

John SmallMtn (00:13:13)

Yeah, my Sandler coach had all the struggles with trying to bring on people onto his team and stuff like this, right? People wanting to come in, not really develop themselves as salespeople, but just show up as the coach and the teacher. And it doesn’t work, right? If you don’t know the territory, everyone knows, right? And when your only advice is “just do more,” people run out of that pretty quickly.

So when you are—okay, so you’re going through this and you’re commission-only, which is crazy to think about, right? How long did it take you to hit that point of being back in front of the room? I think there’s a cool thing if you want to do delivery, right? It kind of brings us up to the tier of—most people aren’t cut out to just be pure salespeople selling other people’s stuff. But I think founders can find a way to summon the will to go do uncomfortable stuff because it’s kind of their baby. How long did it take you to get to that place where you were back in front of the room and you kind of felt like you were selling a thing that you could deliver on?

Chris Caldwell (00:14:26)

Probably about six months. Yeah, I would say probably.

John SmallMtn (00:14:27)

Six months, dude. That’s not that long in the grand scheme of things. I’ve met a lot of Sandler trainers who battled harder for longer and took longer to get success.

Chris Caldwell (00:14:36)

Sure. I think I had a couple of things going for me. What I mentioned earlier is that I had this career in teaching, so getting up in front of the room or coming up with a lesson plan for the foundations class or the sales masterclass was like, “Great, let me get in the lab and put something together.” So I just had that.

And then the mentor that I worked with—I probably talked to him for one to two hours every single day. I was literally in his office just asking him question after question after question. And he was just telling me everything he knew. So I was able—it’s like The Karate Kid and Mr. Miyagi, right? I was able to catch up and surpass so many other people that I came into the business with. I was just miles ahead of them six months in because I had had 300 hours of one-on-one mentorship with someone who had been doing it for 35 years and shared an office with David Sandler for five years. So it was like I was getting the transmission right from Sandler through Rush. That was hugely beneficial. And I give myself credit for being so open to it and being so interested in it, but obviously the credit would go to Rush for all the time he spent with me.

John SmallMtn (00:16:06)

My coach would always do this thing where he would say, “Well guys, if you need anything, I’m here.” And because of my background of training in martial arts and everything, I have zero problem monopolizing anybody’s time who’s willing to give it to me, right? Similar to you, when there’s knowledge that I want, it’s just better for everybody involved if you just give it to me—don’t hold it away, don’t try to linchpin me or anything else like that. Just give it to me, because I’m going to go figure it out, you know?

And so I started doing the same thing, right? I’m like, “Okay, I’ll spend an hour after class, I’ll take you to lunch, I’ll bring you a coffee early, I’ll show up early.” And kind of that same thing, right? There were people who had been in that class for a long time, and then all of a sudden they’re like, “Man, John, you got notes?” And I was like, “Well yeah, you’re not taking notes?” They’re like, “Nah, you know, I’m just going to take the lesson learned at the end of this thing.” And I’m like, “Okay, you know?”

So fast forwarding—because I think we could talk about Sandler and great mentorship for probably a couple of days—let’s talk about you going out on your own. What were you doing? Were you still with Sandler before you opened Sell As You Are?

Chris Caldwell (00:17:24)

So I left Sandler and I was a VP of Sales for three years. I had a non-compete with Sandler, as all trainers do, so I couldn’t just go off on my own. To be honest with you, I had ideas of what types of changes, updates, or adjustments I would make—how I would create my system and my process and the language I used.

Through that anxiety and the overwhelm and everything I felt early on, I really leaned into personal development, psychology, spirituality, human communication, et cetera. And so I was learning so much outside of the Sandler stuff that I wanted to bring in. I really wanted to help create a confluence of the being and the doing.

But first I wanted to try it. I wanted to see if it worked, if it would actually work on a sales team—like if the things that I really believed would work would actually work. And so I took a VP role in which I led a team at a company up in Baltimore, and I did that for a few years and I learned a lot. I learned a lot about what I thought would work, whether it worked or not, and why it did or why it didn’t. I learned a lot about leadership. I learned a lot about managing people. I learned a lot about myself.

And so after a few years of that, then I felt fully ready to go off on my own, and whoever decided to work with me, I would be able to bring the solution that they really needed—not just based off conceptual understanding, but real-life application.

John SmallMtn (00:19:13)

I’m floored at the thinking of, “I want to go test the mettle, right? I want to go see how different this is, how unique it is, and then what works and what doesn’t work.” Because I tried to do a similar kind of path. Whenever I was going through Sandler and working with my coach, I was working with a business partner and we were doing affordable websites, and I’m learning about selling on the basis of solutions and problems, gaps and challenges, and all of that other stuff.

When I launched this business, it wasn’t to be a sales coach or trainer. It was just to build CRMs for people, because I knew these really great trainers that I had been learning from and everything. And I had head trash of like, “Is my stuff really any different?” Because I knew there was a bunch of stuff I wouldn’t use that I was hearing from certain Sandler trainers that I just was like, “Nope, not doing that, not doing that, not doing that.” So I’d kind of built my philosophy a little bit. But it was still very much around the idea of like, “I’m not a hunter. Everyone just wants hunters, right? So this is just how I’m going to sell.”

And then in the pandemic, someone was like, “Well, can you teach someone to sell the way that you sell?” And I had this moment of like, “You don’t want me to teach your people, I’m not a hunter type,” and everything, you know? And he goes, “Well, I’ve just really appreciated this conversation. I would like this if you can do this.” It was a super surreal moment, because I was seeing friction with the CRM thinking and some of the builds that I was doing. Because your CRM is tied to your philosophy if you’re actually the one building it. Now, you can hire a really great systems admin to go build your CRM for you, but it’s probably not going to be attached to the reality and the vernacular that you’re using as you’re going about trying to get your work done and everything. And so I just wanted to build a CRM because that was the feedback loop that I couldn’t lie to myself anymore, right? It forced me to get coachable.

It took me a long time. I had different head trash around that whole thing, because it was less about “I think my stuff is different,” but it was like “Nobody wants this kind of stuff.”

I love that idea of going out and proving it. What did you think was going to work that just categorically didn’t? Is there anything top of mind for you where you were like, “I’m going to be different in this way,” and then you do it and it just catastrophically blows up in your face? Do you have anything like that?

Chris Caldwell (00:21:41)

I think that there were a couple different areas of the sales process that I had been taught should be non-negotiable, and I actually felt like, “They can be really negotiable, and I can water them down and they don’t have to be as non-negotiable.” And that did not work. The things I was taught should be non-negotiable really are non-negotiable.

And so that is actually what I found out: by weakening the process and by watering it down, and by really teaching something that my sales team actually wanted—like the part of them that was scared of really being in their power and making people uncomfortable was like, “Yeah, let’s water this down, that’s a great point”—by giving them permission to do that, I was actually not helping them at all and creating just too much gray area.

So, yeah, that I think is what I learned more than anything else. And I was reminded of a lot of things that I just didn’t feel like had to be so—like, I’m not a black-or-white guy. I live in the gray area, and my relationships often exist there. And so I felt like I’ll just bring more gray area, more nuance to it. And I actually made it leaky and made it weak in many ways.

John SmallMtn (00:23:17)

I don’t even know how to respond to that comment, man, if I can be really honest, because my path is so mirrored to that, but so completely different. Because I was always feeling friction, because I am a black-or-white guy. I’m a C on DiSC. I’m much more of an engineer than I am actually a salesperson. And honestly, my sales trainer told my business partner, like, “Maybe not John for the sales partner inside of the company.”

And whenever he showed me DiSC and my results and everything, I just had this moment of like, “I just need to go find people who were similar to me and stop trying to learn from people who don’t have a manner with which to convey the information to me in a way that is helpful.” Because busywork is like the bane of my existence. It always has been. We were talking before the recording about serving; I was a server for a long time, and running duties and side work—I hated it, I hated it, you know? And it led to some struggles in early sales roles until you really just kind of develop the discipline and habits so that way you can get it done the right way.

And so for anything, I’ve had to get more into that gray area of not being as rigid and things like that because, especially for this thing that I do now, I do not work with anybody by force, right? So I’m not going to make big promises. You have to want the development of this whole thing, not just the outcome of it, because otherwise we’re not going to be aligned, you won’t make the changes, stuff like that. And so I’ve had to get way more just okay with like, “Hey, you say this is a big deal, but maybe not,” in that disconnecting from the outcome, right? Because with it being very black or white, as soon as I put it into a box, I’m making all these assumptions that get in my way and stuff.

So I’ve had to go the other way, which is just interesting. But it makes sense looking at the personalities, right? I versus C, we’re kind of on the opposite angles.

Chris Caldwell (00:25:10)

Yeah, for sure. And I also think that that allowed me to then adopt a “yes, and” in recognizing that like, okay, these things are non-negotiable, but let’s talk about the energy of it that should be non-negotiable—not necessarily the exact word or the exact phrasing, but let me talk about what are the energetic boundaries we’re trying to create here, and then how does each member of my team manifest and express those boundaries in their own way. That’s what I try to do. I say we have very specific non-negotiables, but those are more like boundaries that you should set in your process. It’s going to look and sound a little bit different for everyone, but the boundary is the same.

John SmallMtn (00:25:48)

Man, I have to tell people, don’t try to sound like me, right? Sometimes when you’re really good at coaching and teaching, you can just drop into a roleplay and say, “Well, here’s a question, here’s a way you could pose that, here’s a talk track.” And then people are like, “Can you say that again?” It’s like, don’t take the wrong note here. I’m not telling you what to say. You need to find a way to convey this as yourself, because there’s a handful of things from my business partner that are beautiful conversational levers, right? I can’t use them, because I just hear his big dumb voice in my head the entire time and I just feel fraudulent, right? Talk about this idea that you really need to own your messaging, right? It can’t just be empty technique. It has to be intentional. Not to get too much in the weeds, but I think that’s one of the gaps inside of Sandler: they’re giving out all this technique, but there’s no real ownership of it. It’s not taught how to use it, so a lot of it becomes like crutches for people.

Chris Caldwell (00:27:00)

Yeah, if you understand the why and the how, the what becomes so much easier. My decade of coaching sports taught me that, especially when you’re trying to coach teenagers how to do something. If they can understand why they should do it that way and specifically how to do it, then they’ll do it. But if you just tell them what to do and they don’t understand why it’s actually in their best interest to do it, then they won’t, because the juice isn’t worth the squeeze, right?

The thing that makes me the most effective as a sales trainer with my clients is being able to help them understand: this is the pattern you are in, and this is exactly how you’re causing your own suffering. This is why you’re doing it from a psychological perspective—like these are the needs you’re trying to get met, this is how you’re giving your power away, and this is how you’re sabotaging yourself. When you can communicate that to them, then they’re like, “Whoa.” It’s like, yes, now let me show you how to behave out of that. What would it be like if you didn’t do that? What would it be like if you were in control, if it was more predictable, if you could be more present and authentic with people? Now they’re enrolling themselves into a different way of doing it. From there, I just tell them what to do and they do it.

John SmallMtn (00:28:30)

One of my favorite lines is: when the student is ready, the teacher will appear, right? There’s a whole backside to that line, but we’re just going to keep it to the part that’s super popular. It was so funny, because teaching martial arts before any of this stuff—that’s actually where I met my business partner and my first field sales boss, was in a martial arts school. We would have these conversations of like, don’t try to go too deep, because if you try to go too deep too early, they’re not going to hear it. Then it’s just endless, “Well, you don’t get it,” or “In my old school,” all these avoidance tracks that happen.

It was interesting coming into this and working with my coach and learning about avoidance and that just because I have a reason doesn’t make it a good one, and all of that beautiful stuff. If you’re working with a really great trainer, they should be getting deep with you, because the tactics alone aren’t going to make you do the hard things willingly and consistently.

Going forward, you go into this role, you’re working with the team, you’re testing your ideas, things are working, you’re seeing improvement, and you’re iterating on this thing. Can you talk a little bit about the decision to leave that team and to go out and launch Sell As You Are? What happened there?

Chris Caldwell (00:29:39)

Yeah, I did it during COVID, which is not ideal. No one had budget for anything. I knew what I was getting myself into—no victimhood here—I knew, but I was just ready. I had a conversation with a guy named Justin, who was my boss in my corporate role, and I let him know that this is what I wanted to do.

When I interviewed for that job, I told them, “I have a one-year non-compete. If you hire me, you have me for one year, and I will give you everything I got while I’m here. If I really like it, I might stay longer.” I ended up staying for three. It wasn’t a shock to him when I told him I was ready to go off, so I was able to continue to work with them and they became a client.

Then I had some people from my days in Sandler who had told me that they were waiting for me to start my own thing so we could work together, which was really cool. So I reached out to them, and the rest is history from there. I was able to bring on some critical members to my team to help me build out the content, the design, the branding, the website, the online course, all of those things. A woman named Kate Barry has been insanely valuable in my business—just a true creative genius. I’ve given her free reign for years in my business.

My job is to coach, to train, to be the one coming up with content and putting the curriculum together. I’ve recruited Rush over, my mentor, to work with me. He helps on the corporate side of things with strategy and keeping my head on straight sometimes. So it’s just been a lot of fun. Really hard—way harder than I thought it would be—but that’s classic because I have some real arrogance to me, so that lines up well. It’s way harder than I thought it would be, it’s been beautiful, it’s been everything I could have asked for, and who knows what the next five years will hold.

John SmallMtn (00:31:36)

Man, what a cool story. That kind of leads me to my next question, because we do have this background, right? We’ve been putting ourselves out there, doing hard things, challenging ourselves. Well, this is just the next thing, and we have this background, so it can’t be that hard, right? That’s honestly why the show exists, because you can be good at it, but that ain’t nearly enough to find success as a founder trying to launch your own thing. Where did that show up for you the most, launching Sell As You Are? What thing just blindsided you that you didn’t think you were going to run into?

Chris Caldwell (00:32:42)

I did not realize how much harder it was going to be to sell myself. Even when I worked at Sandler, I sold myself—I was the trainer that they were hiring, I would be the point person—but I had the brand behind me. I had the largest sales training organization in the world behind me. I had everything behind me. When I went off on my own—and as you can tell by my background, it was a very unconventional background for a sales trainer—when I went off on my own, people really challenged me. They really asked me questions, and they were really skeptical.

That was very hard for me, because it reflected these parts of me that doubted myself, which I would often push down and not give voice to as a pattern that I developed in my life to find “success.” When those other people would speak the things that that part of me was actually trying to say, it would amplify it and make it very difficult for me. As I’m doing all of this, I’m also going through my own awakening and my own spiritual evolution, in which I’m learning so much about myself and going very deep in those practices. So it was just a lot for me to handle. That was the hardest part.

John SmallMtn (00:34:01)

Interesting. You talked about when you were the VP of Sales, you were testing some ideas and you had to change some of your thinking. Did anything change during that time that maybe you had hard opinions on, or you’d been coached or trained on, or maybe you just thought, “I’m not going to do it that way, I’m going to try it this way”? Did anything change in that season of trying to get comfortable selling yourself with your own brand and your own thing?

Chris Caldwell (00:34:31)

Well, I think in that season, what was really reinforced to me was the importance of doing the basic blocking and tackling: making the calls, doing the behaviors. At Sandler, that was something I always tried to creatively avoid or justify my way out of. But after I worked with enough sales professionals where, when they were on track and doing that, they would get one result, and when they weren’t, they wouldn’t, it became non-negotiable for me.

I had a rule at my corporate job. What I would tell them is: “You get paid two incomes. Your salary and your benefits is the income we pay you for showing up and doing your job and executing on your scorecard—doing your behaviors, logging everything in the CRM, showing up on time, being a professional, everything else. Your commission is what you get paid for doing it really well.” If you would like to not show up and do these behaviors, then you can give your paycheck back, because that’s literally why you’re getting a paycheck.

I was able to carry that over when I started my business, even though I didn’t have two incomes, a salary, or health benefits. I was able to carry that over, recognizing that there are just things I need to be doing every single day to earn the right to be an entrepreneur—like to earn the right to have my own business, to have this freedom to be able to go hang out with my kids for an hour in the middle of the day, to show up and work when I want, to log off when I want. There are very specific inputs that I have to do for myself in order to earn that privilege. So that was really helpful.

John SmallMtn (00:36:17)

Yeah man, it’s funny. I’m a big Jocko Willink fan and I’ve read Extreme Ownership. That “discipline equals freedom” thing is that same thing for me and how I got there. That’s fascinating.

Jumping ahead a little bit, when you think about how you train now versus the other training that you’ve done, or the leadership that you performed when you were the VP of Sales, what have you changed your mind on the most as a trainer now, selling your own thing?

Chris Caldwell (00:36:42)

I don’t know if it’s changed my mind as much as I’ve realized things that I just wasn’t aware of before. What has been most—some things I have realized is how important the art of attunement is in sales: really attuning to the individual you’re talking to, really understanding them, showing up in a selfless way in that moment in order to help them in a win-win scenario. That’s been a really big one for me.

The second one, which is actually a step in my process, is ascertaining their level of commitment—like, how committed are they to really solving the problem? This came from a talk from a Buddhist teacher named Alan Watts. He was giving a speech in England and he said, “If I tried to charge for a Dharma talk in the East, they would ridicule me. They would flame me; this wouldn’t work.” He said in the East, they don’t charge money—they just make you wait outside all day long. He said in the West, the energy of commitment is expressed through what you’re willing to pay.

That hit me, and I was like, “You know what? Before I have any conversation about people’s budgets, I need to ask them on a scale of one to 10 how committed they are to solving the problem.” That question changed everything for me, because I thought people I talked to were in so much pain they had to be a 10 out of 10. I’d ask and they’d be like, “I’m a three.” And vice versa—I’m thinking, “This guy doesn’t even seem like he cares,” and I’m like, “How committed are you to solving this problem?” He’s like, “Oh, a 10, it’s driving me insane.” It’s like, okay, are you really? So that’s been a really big one for me.

The power of attuning to people and the importance of gathering commitment have been critically important. Then really reinforcing to me that I do not give presentations or talk through in detail my plan for someone unless they’re ready, unless they have told me what the next step is going to be. It doesn’t have to be a decision in that moment, because a lot of times there are too many decision-makers involved, but I have to know: if everything works out well, what are we going to do from there? Then I get that on the calendar, too. Being able to maintain control after that point in the process—those were three huge things I focus on.

John SmallMtn (00:39:38)

Man, I love that. There’s this line in Kung Fu that the student who won’t spend a year in the horse stance is not really a student, you know? It’s around the idea that you’ve got to have those foundations, and you have to be willing to do the hard parts—the thousand punches to try to get 10 that are okay, and stuff like that. Thankfully, I already had some of that coming into sales.

I think really what I needed most specifically was room to bring that same kind of thinking, but also working with someone that kind of took it to that level, right? Actually had a curriculum, actually had not just like, “Okay, watch me and do what I do,” which makes me nervous now. Gosh, I’m floored at that response. That made me lose my next question, but that’s great.

Chris Caldwell (00:40:20)

Well, I had a transition in teaching at one point that really taught me a lot. That transition was the first year I taught an Advanced Placement course. I ended up teaching quite a few by the time I was done, but that first year, I recognized at the end of the year they would take a test, and there would actually be an objective measurement of how effective I was as a teacher.

John SmallMtn (00:40:41)

Did that make you nervous? Did that put stakes on you, or was it like, “Let’s go, I’m going to smash this”?

Chris Caldwell (00:41:03)

Like I said, I have quite some arrogance to me, so more the latter than the former, but I was also scared. There was one part of me that was like, “I can totally do this,” and another part of me that was really scared. But what I learned that year was that I’m not there to teach; I’m there to help someone learn. And those are two dramatically different things—potentially sometimes it’s the same thing, but other times it’s two dramatically different things. So it didn’t matter how good of a quote “teacher” I was or how well I presented the material; if they didn’t learn it, I would be exposed on the test that they didn’t learn it.

For me, that’s one thing I learned working in-house when I was directly responsible for the revenue these individuals were bringing in: when I was a Sandler trainer, I could just get up in front of the room and they’d be like, “Man, that sounded great. You nailed it. Great job.” And I’d be like, “Yeah, thanks,” right? But once my role was responsible for whether they were actually learning it, I became much more nuanced and much more skilled at meeting them where they were and teaching it in a way that they could learn it. That’s been really helpful for me at Sell As You Are, just bringing that humility to it. My colleague Kate, who I mentioned, is always like, when they’re not learning it, the first thing we ask is: “Okay, how could we be communicating this better?” They’re not getting it, so if they’re not getting it, it doesn’t matter how good we think we are—they’re not getting it. They’re not going to change; we need to change to figure out how we can help them get it. That’s been a big key for me.

John SmallMtn (00:42:35)

Man, that hits me so hard square in my chest, right? Because before we turned on the recording, we were talking about one of my favorite books—and most people have never even heard of this book—The Inner Game of Tennis, right? We were kind of nerding out about it. Everyone should go read this book.

When I read that book, I was already an instructor in Kung Fu, and I’d had a couple of conversations because I was the guy who was taking it super deep. I was over-explaining and looking at how smart I am, trying to get my needs met as a coach and a teacher of Kung Fu. Then one time my Sifu—my teacher—pulls me off to the side and goes, “Hey, how many different exercises or techniques did you work on with this person?” I was like, “God, just two. They’re rough, you know?” And he goes, “Okay, why only two?” I was like, “Because he’s not good—they’re not good at this stuff yet. My job is to make them good.” He asked me this question and it just blew me out of my body. He goes, “Good at whose level?” Because if you’re an instructor, your version of good should be astronomically different than their level of good. You’re not trying to make them your level of good as a brand new, fledgling student on this path. Get a couple of reps and then move on, move on, move on.

It wasn’t until I read The Inner Game of Tennis—because I was like, “Okay Sifu, for sure, I’m going to change, I’m going to change.” But habits and patterns and precedent run pretty deeply in all of us. Then reading that book, I was like, “I’m still doing that. I’m still doing that a little bit.” It’s fascinating to hear that kind of thinking over there, because I still do it a little bit now. We kind of fall into the things we’re excited to teach and train and talk about, and we sometimes forget—we call it the curse of knowledge—that you forget you even have to talk about the things that were easy for you, because it might not be easy for somebody else. But over-coaching because of needing to get my needs met and show how smart I am and everything—that’s a big well.

Changing topics, Chris, because I want to be super respectful of your time, and this has been a really cool conversation—I think we could probably talk for about six weeks and just bore everyone to tears who doesn’t really love sales yet—when you think about your company now, I’m curious: there’s so much sales advice online, there’s so much dogma, and I love how you’re always trying to go in and give some perspective about not being as hard-edged. Sometimes discounting makes sense; you’re always a voice of reason in the comments. I’m curious: what is the lesson that you see now—the tweet, the social media post—where when you see it now, you’re like, “Yep,” but you couldn’t appreciate it until you had to learn the lesson the hard way?

Chris Caldwell (00:45:34)

You’ve referenced martial arts a few times. I have a t-shirt with Mr. Miyagi, and it’s “wax on, wax off”—master the fundamentals. Absolutely master the fundamentals. There’s a great story of a basketball coach—a guy who ran basketball camps for kids—who went to Kobe Bryant’s camp to learn from Kobe on how to run camps. He asked Kobe one time, he said, “Hey, I’d love to watch you work out,” and Kobe’s like, “Yeah, sure, come at 5:00 a.m.” He was like, “Okay, I’ll be there.” Of course, Kobe works out for three hours and then goes running and runs a camp all day in the offseason. So he shows up, he watches Kobe work out, and Kobe finishes dripping in sweat. They’re both walking off the court, and the guy said, “Hey, can I ask you a question?” Kobe said, “Yeah, sure.” He said, “You’re the best basketball player in the world right now, and you just spent 45 minutes doing footwork drills that I teach to 10-year-olds. What gives?” Kobe just looked at him and said, “Why the heck do you think I’m the best basketball player in the world?”

It’s that. The biggest blind spot I see with my clients is their unwillingness to humble themselves to master the fundamentals of what I’m teaching them. Sometimes they get their hungry ghost and they’re like, “Can we get new stuff? Can we get new stuff?” It’s like, yeah, I have a lot of stuff I could teach you, and you can’t actually do the things I’ve taught you. You think you can; you can’t. We can role-play it right now and I know you can’t. So really, just that humility—and that comes from the sports I played and the sports I coached, similar to your martial arts experience—the humility of: you have to master the fundamentals, or everything else becomes leaky.

That is the thing that, when I see it online or see someone post about it, really speaks true to me. It’s also the same thing that drives me crazy when I’m on LinkedIn or online, because people are just looking for nuggets, looking for nuggets. If it’s not within a structured framework that you’ve mastered, then it’s just going to be a distraction.

John SmallMtn (00:47:51)

Absolutely. The crutch line that I said earlier actually comes from Kung Fu: if you give students technique before they’re ready to use it because they don’t have the foundational components, it becomes a crutch, right? We would always talk about this, because in the Kung Fu school, you’re totally allowed to look at people that are at your level or lower, but you do not look over here where seniors are and the people who are teaching you. If you were looking over there, you got called out so hard. Focus on your own stuff; don’t even be paying attention to that. You’re not ready for that. It was such part and parcel of the path and the community there.

I’m the same way. It’s so funny when I talk with people and I’m like, “Okay cool, let’s role-play this,” and they’re like, “Well, I can’t do the fake stuff. I can’t do the fake stuff.” I’m like, cool, if you can’t role-play with me, you are not running anywhere close to this framework, or doing these things with efficiency, or being poised, or feeling comfortable, or really even being able to hear what they’re actually telling you, you know? It’s always so funny.

Chris Caldwell (00:49:12)

Yeah, it’s like a hitter in baseball saying that he hit .500, and you’re like, “Great, let’s hop into the batting cage. Let me see your swing.” And he’s like, “No, I don’t hit balls off a pitching machine.” It’s like, okay, whatever.

John SmallMtn (00:49:26)

Yeah, yep. There’s people in martial arts who refuse to spar, right? Whenever I run into that—I don’t care what discipline or style it is—all those people who are like, “Well, I train and I drill, but I don’t spar.” Okay, cool, so you think you’re good?

Once again, just like all these people on LinkedIn who are posting about sales advice who have never carried a bag, never carried a number, never actually helped anybody else get to any kind of traction in a sales role, and are just pushing their own personal preferences—it’s like, you’re causing more harm than good. I get so riled up about it because this job is hard enough, right? If you take the wrong advice from the wrong people—and everyone has weird sales dogma that they love to push because they think that that’s the right answer—you can’t take sales advice from people that have not done the job. It just sets you up for failure.

Going back to this thing: you have a lot of technique, you have a lot of knowledge to pass on around sales. If someone was starting today, brand new, first hitting the scene, and they have no background in sales, Chris Caldwell, the sales trainer—what is the advice he would give that first-day founder? Just hung the shingle, let’s go make it happen from a sales perspective.

Chris Caldwell (00:50:23)

I actually posted about this this morning. I would say to just always, always remember what selling is. At its most core essence, selling is being able to present your product or service as the solution to get the individual from where they are to where they want to be in a way that makes the juice worth the squeeze, right? That will bring in ROI.

Like, that’s it. That’s all sales is. Therefore, every moment you are talking about yourself, your product, or your service that isn’t contextualized in that specific frame, you are telling, you’re convincing, and you’re just marketing. Now, that doesn’t mean it can never work, and that doesn’t mean that you can’t get them excited about it, but you’re not actually selling.

The art of selling is being able to properly frame what you do and how you do it in between the space of where they are and where they want to be, in a way that will make it worth it for them to go down that journey with you. So I would say if you remember that as a founder, then you can remember to properly prioritize discovery. Remember to ask them about impact; remember to ask them how committed they are to fixing it. Really fully diagnosing what’s going on, and having enough reverence and respect for yourself to not talk about that stuff too early, because in the end, people don’t have half of the enthusiasm about what you do as you do, and they don’t care. Just like you want to talk about yourself the whole time, they want to talk about themselves the whole time, so just let them do that.

John SmallMtn (00:52:48)

My pet peeve—but it’s also my favorite thing—is whenever I’m listening to sales reps’ or founders’ call reviews and they do this thing: “Now, you didn’t ask about this, but this is my favorite part, so I just want to show this.” Why are you doing that? If it didn’t come up in conversation, if they don’t have a gap or a challenge around this thing, you’re trying to get your needs met. You’re trying to show off. It has to be contextualized or else it’s just there for yourself. It’s such a problem, right? It’s got to be for them, or else it is by default for you, and it’s going to be problematic.

Chris Caldwell (00:53:19)

Yes, yeah. If it’s not contextualized, it’s not selling. You’re just talking about something; you’re not actually selling.

John SmallMtn (00:53:29)

Yeah, I’m just talking at them, for sure. Great nugget, dude. Thank you so much for that.

Last question, and then I’ll let you get on with your day. You’ve been in this space for a while and you’ve seen things change, right? Everyone’s in AI and all these things. For someone who’s starting today, what is the advice you would give a founder with your knowledge, but also seeing where things are right now, so that way they can have better hopes of getting traction sooner rather than later?

Chris Caldwell (00:53:34)

I would encourage them to always remember that the ceiling of their business is their own personal ceiling. That’s it. And the beautiful thing—just like you can say in a romantic relationship, or with a child or a parent—your relationship with your business is a mirror. It’s a mirror to you and what’s really inside of you: the things that cause you fear, the things that cause you anxiety, the patterns that show up. It is all pointing to something inside of you that is asking to be seen, to be dealt with, to be included, to be processed through, to be transcended.

If you can really own that your entrepreneurial journey is simultaneously as much a journey of self-discovery as you choose for it to be, then even if it fails on paper—which it might, whatever definition we want to give to that—it can still transform who you are and it can still change the way you look at the world and the way you look at things. It can help instill different values in you.

So that’s what I would encourage for any entrepreneur, for any founder: if you allow it to be a mirror—like the grist in the mill, as Ram Dass would say—allow your business to be the thing that changes you. Then even if the business doesn’t work for whatever reason, you are now changed, and now you’re going back into the world, back into the job market, whatever it would be, as a different version of you because of it. But the odds are, if you really embrace it with that perspective and that humility, it will work out just fine.

John SmallMtn (00:55:25)

Wow, man. I’m going to add on a question, because we’ve talked about a couple of different philosophies and lines of thinking over the course of this conversation. I’m a philosophy nut. I’m curious: where would you point founders in the name of philosophy or this kind of stuff that we’ve been talking about and alluding to as a good starting point? Do you have a particular place? Is it Watts? Is it Thich Nhat Hanh? Is there a good entrance door in your perspective?

Chris Caldwell (00:56:23)

Stoicism is great for a founder, especially with all the distraction we have in today’s world. Marcus Aurelius—Meditations by Marcus Aurelius. Ryan Holiday is a contemporary author who writes about Stoicism. I think that that’s wildly valuable.

Adlerian psychology is something that’s been powerful for me, specifically the book The Courage to Be Disliked. That changed everything for me when I read that book. I went down a lot of rabbit holes around Alfred Adler. I don’t align with everything he says, nor should I, because I’m not him, but he has been very catalyzing for me. So yeah, I would point people in that direction.

John SmallMtn (00:57:03)

What’s fascinating about that is I read that book—I’m not sure how it got onto my radar—and I was like, “This is so interesting.” I try to share books with people who are interested; I don’t try to force it, because not everyone’s a reader. But a really good friend of mine, who’s a big “I” type—and what I have found is that “I” types specifically get so much value from that book, right? Because a lot of their core wiring is around being liked and being the center of attention and stuff like this.

I was reading it, and we checked in, and I was like, “There’s this interesting book.” He went and consumed it. It was a great book for me and super helpful, but for him, it was, I think, as meaningful as it was to you, which is a really cool thing, right? Since most salespeople and founders are going to be way more of an “I” type than they are typically going to be a “C” type, I love that as a recommendation. Thank you so much for putting that out there. That’s awesome.

Where should people come hang out with you if they want to learn more about you, or if they just want to see your content and see where you’re going? Where would you point people?

Chris Caldwell (00:58:17)

LinkedIn. LinkedIn is the channel I’m on the most. There are a lot of Chris Caldwells out there; I’m the one in Annapolis, Maryland who runs Sell As You Are. So it’s LinkedIn. They can check out my website, sellasyouare.com. That’s where I would encourage people to find me, connect with me, shoot me a DM, and follow me for more insights and perspective.

John SmallMtn (00:58:20)

Awesome. Chris, this was everything I was hoping it was going to be. I really appreciate you coming on here. I get to talk about sales a lot, but I don’t normally get to talk about it at this level. I really do think that this is going to help some people, especially if they don’t come from sales backgrounds, right? Because most people are holding it a little bit badly. So I really appreciate the depth, man. This is really, really cool, and I think it’s going to help some people. Thank you so much for coming on.

Chris Caldwell (00:58:46)

Of course. Yep, I would agree. Absolutely. You too, man. Thanks for having me.

John SmallMtn (00:59:10)

You’re more than welcome. I’ll talk to you soon.

Chris Caldwell (00:59:11)

All right, sounds good.