Should I get my MBA? Is it a good idea to take a job at a startup? What are the career growth benefits of working for a large company? As a young, ambitious professional, your possibilities can seem endless.

In this episode of “The John Chapman Show,” John Chapman spoke with Chris Calkin, director of sales at CircleCI. Chris dives into his MBA experience and provides realistic advice for those thinking about getting their MBA or joining tech startups. This interview is full of specific insights to help those looking to smartly launch their careers and take the next step to set themselves up for success. Check it out.

AUDIO TRANSCRIPTION:

Announcer: Welcome to the John Chapman show, where we talk about the path of a wealthy millennial, uncovering the truth about building and protecting your nest egg. Join us on this journey as we hear the stories of millennials and mentors alike to help you plan, manage, and protect your wealth. John is an employee of WorthPointe, LLC. All opinions expressed by John and podcast guests are solely their own and do not necessarily reflect the opinions of WorthPointe. This podcast should not be relied upon for investment decisions and is for informational purposes only.

John Chapman: Hey everyone, John Chapman here. Thanks so much for joining us again on the podcast. We’ve got Chris Calkin here today. Chris and I go way back. We met in 2007 at the University of Washington. Chris is a total hard charger. I admire his work ethic and everything he does. Chris has a great story. He shares some funny comments about being deported from the UK when he was 21 and then just shares with us his career path through tech, getting an MBA at Oxford and then some best practices for those who are considering changing jobs or entering sort of a business development or sales career. Especially now that he’s a hiring manager and gets to see a lot of that. So whether you’re just starting out your career or in tech or thinking about being in a sales position, this is a must listen to. So hope you enjoy the episode. Thanks for again for tuning in. And now let’s introduce Chris. Chris, let’s start it off. Thanks for being here today.

Chris Calkin: Yeah, yeah. I’m happy to be here, John.

John Chapman: I want to make sure to give people some background. So just tell me a little bit about where you grew up and then what money was like in your house growing up.

Chris Calkin: Yeah, I mean, that’s a fair question. I spent most of my childhood in Colorado, just outside of Denver. My dad was a cardiac anesthesiologist. My mom was a band teacher, so I actually had to have my mom as a teacher, which was slightly embarrassing.

John Chapman: I didn’t know that. You’re a closet band geek. You never shared it with us.

Chris Calkin: It was the trumpet marching band that got me out of it. So, I grew up in a positive household with a lot of great things and got the opportunity to do things like ski and travel and have my own bedroom when I was young. But I wasn’t one of those kids who was super-spoiled or kind of got whatever he wanted.

John Chapman: Do you think your mom and dad intended to do it that way?

Chris Calkin: Oh, 100%. And my mom grew up in a household that wasn’t super wealthy. Both of my parents actually grew up in households that weren’t super wealthy. So yeah, they were very cognizant of spending, especially my mom. And she would be kind of almost to a fault, cheap at points.

John Chapman: Did she talk about it out loud with you guys or is that something you witnessed?

Chris Calkin: It’s more something that we witnessed, really. My dad would speak to us more out loud about it, especially as we got older and would start to have our own jobs and we are starting to ask for more and more things at the same time. There were certain things where my dad was always like, if you ever need books or if you’re ever interested in sports, we’ll take care of that. I think it was really cool because it showed me that there were certain things that are investments in your children and also made me happy and I became a really avid reader when I was younger and it was always fine. You know, we’d go to Barnes and Noble and I’d pick up 10 books. It was awesome. But if we wanted toys, then later video games, it was a different story. We were buying that stuff on our own.

John Chapman: Okay. Did you identify as a saver or a spender? It sounds like your parents were fairly good at being savers, but did you identify one way or another?

Chris Calkin: I think for me it evolved when I had my first job when I was a like 15 or 16. At a pizza shop. It was fun. I liked the pizza in Colorado. I was just earning money to spend it on something, right? Like I had some goal that I wanted to earn money for. And so I wasn’t gonna waste it on something that wasn’t what I was trying to earn money for, but I would spend it.

John Chapman: Right. You remember it’s a good lesson to have when you’re 15 and getting a first job. It’s your money that you can spend on some sort of goal.

Speaker 3: Right. Which I think is important for everyone. You have to have some kind of drive. But I think later, when we were in college together, I remember sitting down and eating some chicken ramen with my girlfriend at the time. And I remember just saying like, I hate being poor. This sucks because I’m not able to get the things I want, but the things I know are beneficial for me, whether it’s my health or my wellbeing. And so I started to think about money a little bit differently then, when I was 20 or 21.

John Chapman: Do you feel like in hindsight 20-20, there was a moment that was really a light bulb?

Speaker 3: I think the light bulb was starting to turn on then. You know, I wish I could say I had one big turning point in my 20s that turned all of a sudden and I was great at saving. No, I’m still spending money on stupid things and wasting money. And then when I was really into my first career, I was still doing the same thing because I had more money than I ever knew what to do with. I started thinking I need to be able to save for a rainy day. And it’s not just a rainy day. It’s, you know, maybe I’m going to have a hospital expense or maybe I’m gonna want to take a trip to, you know, see my grandparents or something like that. That’s going to be important, but you don’t think about it when you’re 18; you start thinking about it a little bit later.

John Chapman: You start realizing you’re wasting money — not getting a lot of return from this spend. So we talked about that briefly in our conversation while we were setting up this podcast, about being in such a frustrating point in life when you’re poor in college that as soon as you do start earning money right out of school, it’s easy to spend the next dollar you’re earning because you’re just so desperate not to have top ramen. We talked about the type of trap that can be, though, because then if you spend maybe even just one or two years right out of school, while I’m continuing to live that little bit more frugal lifestyle. You know, the percentage of your savings, a percentage of your income that you can save can be actually like wildly dramatic.

Chris Calkin: Right? Oh massive. And there were so many things I was really lucky to have when I did graduate. You know, I had some speed bumps along the way, but you know, ultimately, got that first job in a startup that was actually successful and rather than fizzling out. I’ve talked to a lot of very smart, very ambitious people who’ve just chosen the wrong company and it has not worked out for them. There’s so much luck in that point in time moment, which is frustrating, especially because you don’t know — you’re 22 years old and you really don’t know what to look for or what to do. When we talked before where I was like, if I could go back and go, okay, this is your money now. This is what you need to be thinking about and it’s fine.

Chris Calkin: Go have fun, go spend money. You know, this is the fun time. This is a fun time to do that. But if you don’t spend it on this thing this way, you’re going to be netting out a lot more positive outcome later. And that’s, yeah, something that I wish I could go back and say. Then eventually I started to realize that.

John Chapman: I have to pause there because I was thinking about that after we last talked and in preparation for this, like where’s the line between being told some good advice and taking it to heart versus just like learning from the school of hard knocks, because you did learn through that and thankfully you probably learned that earlier on compared to maybe others out in there in the world. And so that was a valuable lesson. So maybe it was like totally worth it, but had somebody told your younger self, would that have even made a connection or if you did follow their advice, I wonder if you would’ve just eventually had to overcome that obstacle?

John Chapman: I guess just for everybody who’s listening, I’m wrapping my mind around this idea between taking good advice versus like learning from the school of hard knocks and trying to figure out where those intertwined, and it’s not an easy thing to answer, but I’m interested in your feedback on it.

Chris Calkin: Yeah, it’s a fair point. And I think that just applies for a lot of things, where someone can give you very sage advice, but ultimately are you in a position to be receptive to that advice and then actually act on it. I think the best way for me, if I were to talk to someone who is 22 to 23, I’d say, “Hey, go talk to someone maybe a few years older than you who you think is being successful in the way you want to be.”

Chris Calkin: Get the advice they can relate to a little bit more. Like we talked about with being raised in a family that definitely understood the value of money. That did a lot for my foundation. But if I was to go back and talk to my dad when I was 22 about his finances, how he was managing his finances, it wasn’t going to be as relevant for me. Right. If I talked to you now, if I talk to someone who’s, you know, 27, 28 and successfully doing things in their career path that I can relate to, that would resonate the most. At the same time, I still think you have to have at least one hard knock because it doesn’t really set in until that happens. And you know, there’s some people who are better about that than others, but I think getting advice from someone who’s relatable would be my recommendation.

John Chapman: That’s super interesting. So I want to come back and think about that. When you did graduate, you went down to San Francisco, and you chose not to go into the big four accounting companies.

Chris Calkin: So how did I end up going to San Francisco and choosing tech? Well, I don’t know if you remember, but I got deported from my first job in England.

John Chapman: Oh, I forgot about that. I actually totally forgot about that. Tell everybody how that happened.

Chris Calkin: I mean this is a naive story, right. Of a 21-, 22-year-old who’s entering their career. I had a family friend who was a very successful entrepreneur in the UK. I approached him and asked for an internship, which I think was a very mature thing at that point. He was like, yeah, it sounds good. And then before the internship was scheduled to start, I was kind of concerned cause he wasn’t very responsive and I ended up packing up my stuff and flying to London. l had totally taken a risk. And then I get to customs and they say, well where is your P visa? And I was like, I was told I didn’t need that type of visa. I was interviewed, and told, “you can stay in London for the night, but your flight back home leaves tomorrow.” So, wow, that was a huge shock. And that’s when I started to realize, okay, you’re not in college anymore. You’re taking care of yourself. Everything you do, there’s going to be some ramifications. And in a long run it was actually amazing. I think about everything that’s happened in my life that would have been different had that one conversation at Heathrow gone differently.

John Chapman: Yeah, it was that impactful. I mean weren’t you feeling embarrassed or frustrated or wanting to scream or call this guy?

Chris Calkin: All of those things. And I remember sitting on the tube just thinking what am I going to do? And I had really heavy bags with me, too, because I was planning on moving my whole life. So absolutely. When I got back, I really took charge of things lot more. I didn’t rely on other people as much, depend on someone doing the right thing. That really served me well because then I was able to take accountability for not only my own actions, but my own wellbeing and welfare. And I think that led to a lot of really positive things. I worked in Seattle with a startup for two years and then I moved down to San Francisco with that startup. And honestly, for the first two years, I didn’t think about money.

Chris Calkin: It wasn’t really my main goal. My main goal was just growth and learning within that organization and taking on more and more responsibility and ultimately make sure that organization found success. And today I still look for people who are thinking that way. You know, it’s fine to be money hungry, but if you’re only that, a lot of times I think that can limit your career growth. So you might do very well in that one position. But you won’t get beyond that. I got five promotions. Would that have come to before I decided to move on between Seattle and San Francisco?

John Chapman: Oh wow. That’s amazing. There’s so much you talked about that I want to come back to. I mean first, you did revisit the UK. And I want to talk about your business school experience in a sec. And then I also want to talk about, now that you’re on the other side, you know, 30, and hiring people coming right out of school and talking about sort of what attributes they should or shouldn’t have. So maybe we can come back to those in just a second. Let’s see, you moved down to San Francisco and you were there for a few years, certainly growing and learning a ton. When was the point where you thought that, well, business school was the next most logical step?

Chris Calkin: I think it was a life piece more than it was a career piece. I looked at what I’d done and I was proud of what I’d done, but there were certain things that were limited to me because I was still 26 or 27 at the time and you know, I was thinking, okay, I want to get that next step in my career, but I’m not sure this company is really where I want to do that or where I want to continue. I loved the company, met a ton of great people, but it wasn’t necessarily what I wanted to do. So I was like, you know, what would be great is if I could kind of step away from thinking constantly about getting that next job and really be more thoughtful about what my approach is and synchronize for a second. That’s smart. But also at the same time, continue to learn and advance my life. I took the GMAT —  I’d taken it four years before — and I was like, I’m going to get my MBA now. It’s time.

John Chapman: Okay. Right. And you could use that score from four years earlier?

Chris Calkin: Yup. It expires in five years. And you know, I had just taken the test kind of randomly. I wasn’t necessarily thinking about going for my MBA right then. I did it mostly because I was bored at home and decided to study for it and take it.

John Chapman: Wow. Closet band geek turned closet GMAT nerd. I don’t know of anybody who would like willfully want to do that.

Chris Calkin: Well, when you’re still in school mode, you probably have some of that muscle memory of studying and more free time and less responsibilities. It is a nice card to have in your back pocket. I certainly liked not having to take the test when I was 27. I would caution people to not jump directly into their MBA without work experience. It’s not going to be as applicable. And you’re not going to understand and appreciate the value right out of college.

John Chapman: I totally agree. I think you know, I haven’t gone to business school. I considered it very briefly and I decided for my career path for being a financial planner that wasn’t something I really wanted to do. You know, when I was considering it, I thought of like your typical UCLA or Berkeley, Chicago, Stanford, yada yada. How did you come across Oxford?

Chris Calkin: I was thinking the same thing, right? When I was taking the GMAT, I was thinking Berkeley would be amazing. But then when I really wanted to actually do it, I was like, why am I doing this? I’m doing this to give myself a new perspective on my career path and to go somewhere like Berkeley, which is an amazing school. I didn’t believe that would have given me as a diverse perspective as going somewhere like Oxford. In Berkeley, I’m going to be interacting with people who have backgrounds in software or technology, backgrounds that were similar to mine. At Oxford, that was not the case. There were very few people, if any, who really had a similar background. And there were 58 countries represented. Ultimately, it had that brand value.

Chris Calkin: You know, there are a lot of great schools in Europe, but I think few of them translate to the U.S. just in terms of, you know, as a hiring manager, understanding, okay, you know, NCI, that’s a great school, but have I heard of it? But Oxford, everyone has heard of it, so that was attractive for me. The other big thing, a huge reason I decided to go to Europe, is for life experience. I traveled to 11 countries while I was there and that was really fun. Also, it’s just a one-year program, so you’re not only not paying for a second year, you’re working that additional year as well. It’s a lot less of a financial and time investment. Two years on the surface isn’t like a long time, but I think in the thick of it, it could feel like forever, like exactly.

Chris Calkin: For others, it might make more sense to do a two-year program. I felt that I was already kind of at a little bit more of a senior stage of my career, so I didn’t necessarily go into the MBA thinking, okay, I need this two years to build my resume to then get a job at a big four. That was not the route I was going to take. But a lot of people I know have had a ton of success with those two-year MBAs, so it’s not that the one-year MBA is the end all be all, but I think for me in my position, it was the right thing to do.

John Chapman: So another thing I hear about MBAs is that people use them to change careers. We had friends who were teachers and wanted to go into careers in corporate finance, but they weren’t necessarily going to get hired for that because it just wasn’t a clear logical step. So, they use business school as a steppingstone for that. For you, you had worked in tech in San Francisco. Did you assume you were going to go back there or did you start with a clean slate when you were going into business school? Like you wanted to use this as a steppingstone into HR or something else?

Chris Calkin: That’s a great question. I didn’t quite have a blank slate. I very much so enjoyed working in software and working in technology and I was fairly confident I wanted to continue to be in that space in one capacity. That’s what I was really evaluating.

John Chapman: Okay. Like being in sales versus management or what? What do you mean by capacity?

Chris Calkin: I talked to companies like Boston Consulting Group’s digital ventures, and was like, okay, I can do consulting work, but I can also involve investments and technology. That sounds like a very cool blend, you know? And I had a substantial background in marketing. It’s definitely still an area I have a lot of expertise in. And so I was looking at a lot of things like that, too, whether it was kind of head of demand generation for a software company and how that would be influential. So that was part of what I was going back to reevaluate. But I really thought technology, and we were also re-evaluating where we wanted to be. I was pretty confident that California was where I needed to be, but I was open to the idea of living in the UK or elsewhere to pursue that next step of my career.

John Chapman: Were you engaged at this point when you were married already? That’s another note. Another layer to the deciding factor. How has being married changed how you go about thinking about your career or even just your day to day?

Chris Calkin: More than can be explained. I think as another married man, you know, but when we were first married, there was a lot of financial stress. And looking back, I’d come back from my MBA, I was starting a new job. I’d moved back to California and we were getting married and we were doing it ourselves. Right. And so that was a lot.

John Chapman: Yeah, that’s a perfect storm of three super hard things. Yeah. I would not recommend that for other people. I’m glad you survived.

Chris Calkin: Yeah, I’m glad we survived, too. And ultimately I think we were stronger for that. But actually the experience with the MBA helped us, in terms of our financial outlook and in terms of our financial plan. Because I think before my wife was very much so thinking like, I’m making money to do things. You know, not thinking about the long term. And that really caused us to say, hey, you know, we want to have this type of life if we’re going to have this type of life in the long term for our life and for our children, hopefully, we need to start doing some, some things differently. And so that was really good. At the same time, you know, there are pieces now where I’m not just thinking about kind of my own financial plan, I’m thinking about her and I’m also trying to give her some flexibility to work through her career.

John Chapman: I feel like I’m even thinking about so many things that I can talk about. I’ll bring it back in then. Let’s think. Another thing we had talked about in our previous conversation is sort of this like this — the dangling carrot of equity and how Silicon Valley specifically and private companies that are tech startups, they like to sort of dangle this ahead. And I’m wondering if they’re invoking this greed and excitement, almost like winning the lottery. So for our peers and most of the people who were your colleagues in San Francisco, how many of them actually get to receive equity and then find any type of reward from it? You know, we only hear the stories of the 0.01% of the population that might get lucky on an Uber IPO or is it more common maybe than just 0.01%?

Chris Calkin: Yeah, I mean I think that you’re absolutely right in that it is uncommon. Even if you’re working in a more senior role for a startup that’s successful, your probability of netting real, real cash from that is pretty low. And the value of equity diminishes significantly. You know, at the same time, I think the way companies use equities, they try to use it as a carrot for those more junior employees they’re trying to bring in with a lower salary or they’re really early stage and they want to convince people that are used to making more money to join their organization.

Chris Calkin: For me, again, I think money is always going to be important. You have to be thinking about your salary, your variables, are all those pieces best in terms of things that are aligned down how much equity you get or don’t get with that company. You know, I think that’s something you can always discuss, but it’s really more of a cherry on top. It’s more of an extra if things happen to turn out. Well, I wouldn’t say I know most people, you know, many people at all, even in more senior roles, who have made substantial income from equity.

John Chapman: So I want to think about like now your role, you do a considerable amount of hiring. I can’t remember the number of persons you’d hired in a short number of years. How many years have you been in this new job post-MBA? How many people have you hired? And then I guess the other question as I’m thinking about things, being down here in Orange County and people talking about Silicon Valley, one of the things on the surface you hear is that people jump around a lot. So in actual practice you’re looking at people’s resumes. Do you see people move around a lot and is that any type of concern or is that just part of the culture? So there’s, there’s 15 questions for you, but I guess tell me how long have you been at this new job and how many people have you hired?

Chris Calkin: Sure. So I’ve been with my company for a little under two years. I probably hired just over 30 people, between account executives and sales development roles in really all kinds of sectors. So kind of some more senior account executive salespeople who have plenty of experience. You know, some sales development reps are just coming out of college. I find myself sometimes getting in a rut and having conversations with account executives and then I go to interview a sales development representative and I’m kind of like, well, they don’t have, you know, any of these abilities. And then it’s kinda like, they’re new in their career as it takes a second for me to pivot. Now, your second question regarding jumping around.

Chris Calkin: We do look at that. That is obviously a massive trend. I think people are looking for how they can jump steps in their career, kind of leapfrog up in their career by going company to company. But I’ve very rarely seen anyone successfully do that. And if they could have done that, it’s usually that they have some promise of more money. So this is the most common where I’ll see someone say, you know, I went to this company and then this other company offered me more. So I decided to jump there and then they went under or they were restructured or x, y and z happened. You go join the right company, get behind a product you like, behind leadership that you like, because whether you stay with that company or not, you’re going to be successful in that role. You’re also going to hopefully benefit from the relationships you established there and then you’ll probably spend more time in there than you would otherwise. You’ll probably get promotions there. On that same note, I certainly reaped a lot of benefits from working with a small organization and I’m biased, but I personally would recommend that people do start their career in a little bit of a smaller organization.

John Chapman: I have a different perspective that I’ll share because it’s different, but not necessarily in a bad way. I can see the pros and cons in it, but sorry, I interrupted you.

Chris Calkin: I can understand a different perspective, but I think that for me, a small fish grows bigger in a small pond. You can have those opportunities to advance, you have those opportunities to do more just your role, and whether or not you officially get the promotion or that next step, you usually have to take on some more scope and that equips you better for whatever’s next. If you join a very large organization in a sales role, a lot of times that role is going to be so structured out, you’re going to have very little opportunity to kind of go beyond the scope of that role. And then if you’re trying to join a startup, you’re all of a sudden like, I don’t know how to do all these other things that you’re asking me to do.

Chris Calkin: When you’re very well equipped, you can actually add more value to that business because you’re like, hey, I can do all of those things. I can do even more. That’s my recommendation. But like I said, I’m biased a little.

John Chapman: Totally. I think you brought up some good things that I didn’t think about before. I think just super quickly, like my experience out of college, I was very confused on what to do. I wasn’t a finance major, which is sort of odd when I tell people now that I’m a financial planner, so I think I needed the structure of a big company to like give me a box to work in. And then eventually, once I latched onto it, I was able to flourish.

John Chapman: I really didn’t take my career seriously actually until two years into it, when I did my CFP certificate, that certified financial planning and then I was like, okay, I got it. I wish I was as focused in school. And so I kind of thankful that the big corporation sort of let me be an idiot for two years until I figured it out. But, then once I realized what I wanted my path to be, I quickly needed to jump ship. I want to ask about hiring one more time, but then I also want to ask about building wealth via some type of business development role rather than just moving up some corporate ladder.

John Chapman: So I want to hit on that in just a second. So hiring, do you have maybe a fun story to share, or one or two quick do’s and don’ts for people looking to change jobs, from your perception as a hiring manager?

Chris Calkin I’ve certainly had my share of interesting interviews and also interesting hires. I’ve had people flourish with me and I’ve had a lot of people go, which is obviously never fun. I think one of the keys I look for is actually what questions people ask. And I think a lot of people say that. But it’s not just, hey, do you have 40 questions to ask me because I don’t have the time to answer 40 questions. It’s your choices on which questions you ask that demonstrate a lot about how effective you’re going to be in this role.

Chris Calkin: Because to me, if someone’s thinking about the opportunity seriously, they’re going to ask about things like, how are you dealing with this competitive situation that just occurred in the news? They’re also showing me they’ve done the research and they’re demonstrating their ability to be successful in that job and be interested in the potential opportunity. That means a lot to me. I also think that I’m kind of an old-school person and a young body, because I really appreciate people who are organized. People show up on time, people work, people go beyond the call of duty.

John Chapman: Oh great. Just some basic blocking and tackling that gets usually overlooked, you know?

Chris Calkin: It’s especially important given how many people want to work from home or have flexible schedules. For me, there have been a few people I’ve seen be successful in those type of roles, so the only folks I would give that flexibility and autonomy to are those who’ve shown me they’ve earned it. They’re still the ones who are first in the office and last out at the end of the day, you know? And that means a lot to me. I’m in favor of flexibility, but I just think it has to be earned. And a lot of times people go in thinking it’s assumed, it’s something they already have the right to. I think that’s a fatal assumption. Whether the organization’s policy is, it’s not going to work out well with that attitude.

John Chapman: Wow. That’s super fun. We’re getting close to our time. We gotta wrap up soon. Another question: At this point, you’ve had obvious learning steps that you’ve referenced before and now that you’re married and you’re thinking about your family in a different way, that’s one of the things that drives you. But what’s a shiny star off in the distance? What do you envision for yourself in the future? And is that what’s driving you day in and day out? So what’s the underlying motivation for your career at this point?

Chris Calkin: I probably have a more concrete idea about what I want in my career than I’ve ever had, which is nice. And it’s also challenging because knowing what you want and then knowing what it’s going to take to get there can be daunting. I’d certainly like to be VP of sales at my current company. It’s essentially what I’m doing today, but it’s not the title I have. I’d like to move into that role and ideally then own the entire organization. So not just the sales team, but also the customer success team. For me, that’s the goal. That’s not necessarily financially driven. It’s just my personal goal. Financially I would like to be able to not rent anymore. You know? And that’s extremely challenging in San Francisco. Totally. But ultimately, it’s something that’s achievable for me, probably within the next year. That would be a massive achievement, and it’s really what’s driving me now.

John Chapman: I like that you’re breaking it down into maybe less is more in this moment. And one of my big things that I encourage sort of young accumulators and the millennial generation, too, is we can focus on things like college or retirement savings, but it’s so much more impactful if you can just home in on one or two goals and save or invest like a madman to achieve one purpose. It ends up happening a lot faster if you can say focused on that thing. I’m sure it can translate to other parts of life, but it’s cool to hear that’s what’s keeping you going right now. Anything else on your mind that we didn’t talk about that you want to say?

Chris Calkin: We didn’t talk about the sales and business development piece. And that is one thing I would just want to preach about for a minute. Ultimately, I think when I was in school and you probably felt the same way, I didn’t look at sales as a career that would really be super beneficial for me or propel me to, you know, great financial success.

John Chapman: Yeah, it had a stigma, too, that word, or is it just the word sales was off-putting. Nobody connected the dots.

Chris Calkin: Yeah, it’s absolutely that. That’s true. And I think people aren’t like, oh, you need to have a business school degree or an MBA to be successful in sales. And I think that’s absolutely false. The most successful salespeople I know are very well educated; they’re very effective at understanding other customers’ businesses because they have that business understanding and they’re also very financially successful. So I would say that for those people who are thinking about having very high earning potential relatively early in your career, you can really grow that massively and you can also increase the scope. We talk in our last conversation about how salespeople often can move into a VP of sales role, but as you move into really any senior role, you’re going to have some elements of sales involved. And so getting that experience early on is something I just recommend.

John Chapman: You’ve preached a little bit about sales and the changing mindset, that it’s not just an icky word, but what it can actually mean for your career. So the people you’ve seen in sales, what are they like and what are some of the attributes we should be thinking about and changing our perspective on that word?

Chris Calkin: I think the traditional take on a salesperson is a kind of precarious, life of the party type person. And that’s really more rarely the case. It’s usually the person who’s actually very well educated, understands business, understands the customer’s business, and really has a deep interest in the product and technology they’re selling. Because that’s then conveyed to the customer. And then ultimately they’re actually able to add a lot of value rather than just kind of pushing a solution. And so that’s where I’ve seen a lot of success. I’d also say that for people in the early stage of their career, it’s one of the ways you can earn a lot higher. You know, when you’re relatively junior and then as you’re advancing your career, it really becomes a requirement regardless of your industry or your role that you have some ability or experience in sales. And we talked about this before, but even if you’re an engineer and you’re working in an engineering firm, as you get to a more senior level, you’re going to have to then work with customers and that requires some sales acumen. When some people don’t take that step, don’t learn sales, they’ll fall on their face.

John Chapman: Yeah, it can be really beneficial regardless of vision or career to get some solid foundational knowledge in it. I can totally relate and I think I felt really put off by just everything around sales. No one explained that to me or sat me down until I started reading more on it and then understand that if you just reorient your mind on what you’re doing, which is actually learning about somebody’s pain point and using any type of service or product you have to solve an issue in them, what you’re doing is potentially changing this person’s life. It took me probably a few years to really reach that understanding. And so I’m still new in that type of thinking, but couldn’t agree more. I could go on for another hour or so. So we’ll have to have you back another time. Chris, thanks so much for being here, man.

Chris Calkin: Absolutely. Enjoyed it, John. Thanks a lot.

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