124: Motivation, Goals & Ambition With Scott Leese

Thank you to our sponsors, LeadIQ, Costello, SalesLoft, WorkRamp, and Dialpad for helping us produce this podcast. Head over to jbarrows.com slash blog for the highlights of this episode and explore resources you can use right away. Let's make it happen. Good afternoon, everybody. This is John Barrow's Make It Happen Monday. Hopefully you all had a fantastic weekend. I am super excited for my guest today because we've become good friends over the years and a little bit of rivals too. I do admit right now I should be wearing a Buffalo Bills gear because I did lose a bet to Scott. We bet on the Pats-Bills game, and they beat the spread. So they didn't beat the Pats, but they beat the spread. So needless to say, Scott leaves.

How's it going? Say hi to everybody. I'm doing good, man. Thanks for having me on again. Yeah, and you're wearing it. You got your gear on, so I like to represent it. Yeah, I got it. And hey, man, I got to be honest. I've been begging Jets fans for a while, please have a good team. Because I thoroughly did enjoy when the AFC East was actually somewhat competitive. It's just been such a joke these days. That's the knock that people have on the Pats. It's like, we already are going to win the AFC East anyway, so we're going to get a buy in the first round. So it's almost like we have a free ticket to the Super Bowl, right? Yeah, you start the season 6-0 the last 20 years. Right? So I actually do genuinely want that to change.

So the fact that the Bills right now are what, 5-1 or something like that? 4-1, I think. 4-1, 4-1. I got some hope here. So hopefully we'll see what happens later on in the season. But Scott, I'm excited to have you on. I mean, we met through Richard, right? Richard Harris, a good friend of both of ours. And your story is a real interesting one. So, you know, why don't you give everybody, because I think it'll lead to where we're going today. For everybody who's listening right now, we're going to be talking about that transition to going off on your own. And the reason is because I get probably, you know, at least 10 to 15 questions on a month on a weekly basis. And at least one or two calls every single week of, hey, John, I got that itch to go off on my own.

And I think sales in general, there's a little bit of that DNA in each one of us where we want to kind of go figure out what our own thing is. But what does that look like? And I'm scared to do it. How does that? So that's where we're going to end up. But Scott, bring us up to date, right? Like, walk us through that story. I know you got like a super interesting story as being a practitioner, but also your personal story. It'll be really helpful for the audience here. Yeah, you know, I got started super late. I think in my career, I didn't get into the sales world until I was 27 years old. Um, I was playing sports professionally and coaching kids and giving lessons and this kind of thing. And I was going to graduate school and then, you know, well documented out there.

But I got really, really sick. I spent four years in the hospital trying to figure out what was going on with me. I had autoimmune diseases. I battled some colon cancer scare, kidney stones all over. It's just like nightmare after nightmare after nightmare. Um, I had four life-saving surgeries, nine total surgeries, total colectomy, removed my large intestine, just nightmare situation. And through that four year period, got hooked on opioids, had to, you know, go through the recovery process and kick all of that kind of stuff. And here I was 27 years old. I really had no job experience, uh, in the business world whatsoever. And I got into sales because it was very similar in my mind to being an athlete.

You know, you work hard, you get paid, you do well, you get paid, you don't do well, you get cut and you're, you don't have a job. So like, I understood that, that mindset. And so just on a whim, I'm like, well, I should try, you know, sales. I think I can, you know, maybe be okay. And I know there's opportunity to make a lot of money and kind of play catch up and make up for lost time. And so that was, that was how I got into sales. Um, so I took a, you know, entry level job in San Francisco Bay area. Uh, I think my base salary was $30,000. You know, if you try to live on 30 grand in, in San Francisco, uh, you know, good luck. Yeah. So I, I really had to, you know, try to, try to make it happen and figure it out.

And it was really, really scary and tough for, for a little bit. Um, but that got really good, really fast, figured out the right mindset for me, figured out the process for me that, that worked. And then just pedal to the metal, you know, um, really outworked everybody big time. I was at a stage in my life where I had that time, you know, my wife was in grad school at the time working hard. We didn't have any kids. It was like, I was all in on, on trying to build a career. And so that was where I put all my focus and all my energy. And, uh, you know, took me a little while, six, seven months or so. And, you know, top rep in the company and got put into a sales manager role. And really for the last 15 years, I've been building and scaling sales teams all across the country.

Um, I've been an operator, VP of sales, six times, five of those companies have gotten to, you know, roughly $20 million ARR or so, all of them in under three years. Um, so that really became my niche. Like I've, I've been the guy who goes in early, helps, you know, figure out the go to market strategy. And it's like, so I'm going to get you from zero to 20, zero to 25, right? We're going to get you to that, you know, a hundred million, 200, $500 million, uh, valuation in that series C growth stage. Um, and I started getting this entrepreneurial itch that you, that you mentioned, um, about three and a half, four years ago and founded my own consulting company on the side. Took a little bit of a different angle.

I'm not, you know, like I wouldn't call myself the typical sales trainer. Um, that's not really what I personally love to do, right? I have to leave that to you and Richard and some other people. I really like to go in and talk to founders and CEOs and maybe, you know, first time heads of sales and help them get a repeatable, scalable process for them to do what I've been able to do as an operator on my own. Um, so that zero to 25 million space is kind of where I like to, to play. Um, so did a bunch of that stuff on the side while I was. Uh, an operator then a year and a half ago wrote a book about my experience and how I got into sales called addicted to the process. Um, that experience led me to kind of get a bigger, broader audience on, on LinkedIn and, uh, through LinkedIn about a year and a half ago, created this company called surfing sales, where I take, you know, 15, 20 people down to Costa Rica.

And in 2020, we're going to go to Nicaragua as well as Mexico. Um, so sort of like a micro sales conference opportunity to have a really powerful and intimate experience with other, you know, like-minded sales professionals, everybody from SDR to VP of sales, to, to CRO, uh, to CEO even. Um, and, uh, as of 17 days ago, um, I'm on my own. I decided that now was the right time to go all in on my kind of consulting business, try to grow surfing sales. And I'm in the process of writing a second book and, um, that's kind of how I got to, to where I am right now. So a lot of shit to unpack there. Yeah, a lot of stuff. Yeah, a lot of shit to unpack. But I want to, I want to go back to, I want to go back to, to your challenges of, of kind of that four to five years of you just going through shit, right?

From a health standpoint. And, cause I think of the, the, the mindset, uh, I want to chat with you about, cause I want to talk about your mindset through these phases. What, what kept you going through all that shit? I mean, it, like, you know, a lot of us get knocked down once or twice, like, fuck it, I can get back up after that. But after you get knocked down time after time, like what kept you going through that shit outside of just staying alive? Like, was there something that you locked into that said, man, like, this is why I'm going to keep pushing through this shit? Or was it just a pure survival instinct? You know, I think it was honestly survival instinct more than anything. And it was the first time that I, I, I sort of learned and figure out I need very small micro goals.

Yeah. Right. Cause it, it was a huge mistake to try to think like, okay, when am I going to get out of the hospital? Or when, when is this sickness going to go away? Right. It was, it needed to be, how do I get through the next hour? Cause then I know the doctor's going to come talk to me and I can get an update. How do I get through the next block of time before I can have my next dose of medicine or, or pain medicine or whatever. Right. How do, how do I get through till tomorrow? Because tomorrow we have this particular procedure we're going to try. So, you know, it's really, really important in goal setting to, you know, have a, have a big, huge, audacious goal. Right. But you've got to be able, I think, to, to show progress.

And that, that progress reinforces that you're on the right path and that you're, you know, succeeding. And, and, and I'm somebody who has typically had a hard time in my life feeling like I'm making progress until the payoff is there. And so that, that was the first time in my life where I was able to focus on these more, you know, small scale kind of goals. And I think that combined with the survival instinct is really what kept me going, you know, that I can't. And, and I hope everybody heard that because that translates so well into sales in general. Right. Because we get knocked down day after day after day. Right. We're all looking for that little needle in the haystack. And, you know, when I used to do management coaching, I do some now, but I don't like have a program around it.

But a lot of times, like you look at your A, B and C reps, right? A lot of people say, screw your C's, whatever. But no, you should work with your C's. The problem with your C reps, the ones who are in the shit, is that they're used to losing, right? So they're used to getting knocked down. So therefore they kind of stay down. And what, and so instead of sending these big hairy goals, right? And say, okay, now you, you need to hit your quota this quarter. What you do is, hey, today, can you make, can you make 50 dials today? Just like, let's try to hit a number. Can you make 50 dials today? Okay, good job. Now tomorrow of those 50 dials, can, can you get one, like two conversations with people other than gatekeepers?

Good job. You know what I mean? So you micro goal set. And what happens with that is you change the mindset, right? Because now you start winning. Now you start looking at those little things from a winning standpoint and it builds and builds and momentum is, is a, is a powerful thing, right? Yeah, a hundred percent. I mean, winning, winning is contagious. Absolutely. You know, so it's losing. So it's losing. Sure. So it's losing. So one of the first things you got to do is change the paradigm for yourself. You know, you've got to find a way to celebrate something. So even when I'm, you know, damn near half dead in the hospital, like I'm trying to create these, what these victories for myself to sustain me and keep me going, you know?

So, so let's, so now let's talk about mindset. Now you get out, you're good. Uh, you want it. You like you'd figure out what out, you know, you, you said, Hey sales, you made that connection there. I like it. Get a little barrier to entry. Fuck it. Let me, let me try this thing out. But it's, it's gotta be a humbling experience at the age that you were at 27 years old, right? To, to, to take a step back and go entree level into sales at 30 G's a year. So, so where did that mindset come from? Cause I think a lot of people, um, are not willing, like they get to a certain stage of their career where they're quote unquote successful at doing whatever they're doing. They're making okay money. Right.

And they might want to make a shift because they were either boarded this or whatever it is, but they're, they're not, I guess, either humble enough or willing enough to take that two to three to maybe even four to five steps back to then potentially, you know, really go at a different level in their career. So what was that? How did that happen for you as far as the mindset to, to, to be humble enough to, to, to take that, you know, entry-level role into sales? Well, I got, I got, I'm of two different minds about this. Um, number one, there is nothing more humbling than, than feeling like, um, you know, you're kind of a bit of king of the world. And then all of a sudden, like you can't do anything yourself physically.

Yeah. Uh, you know, when I was playing professional soccer, I'm six foot two, I weighed probably about 190 pounds. And, you know, in a span of two months, I weighed like 140 and couldn't move from the hospital bed to the restroom without assistance. Um, the, you know, so I had humility thrust upon me unwillingly to be honest with you. Um, and you know, I, luckily I think for me, I, I, I accepted that particular lesson. I, I, I don't know that I'm special in that regard, but, um, it would be a shame if you go through something like that and you don't have a bit of a different perspective. So I was already humbled. I was already like, dude, I have nothing. Right. I, I have nothing. I am nothing.

Like I gotta, I gotta build this thing from scratch. So that, that's the first piece to, to answer to your question. The second piece is, you know, I did not fancy myself a, in my mind, like a frontline worker, a frontline thinker, a frontline leader, if you will. And so I needed to move up the ladder as fast as possible. And this is an important thing because, um, I took steps backward financially time and time again. So not just to get into sales, but you know, I was the number one sales rep in the company. I moved backward because I wanted to be a sales manager. I was making good money as a sales manager. I moved a bit backward to become a senior sales manager. I left a senior sales manager role to take my first VP of sales role at a tiny little company where I had no guaranteed commissions or we didn't even have a product hardly built yet.

Right. Then I left that gig and went to another VP of sales gig where, so every time I made all these bets on myself, right. And then I finally got a VP of sales gig that gave me equity. Well, then I left that gig that was doing really well. And I got a bigger salary, a bigger OTE and more equity, but I had to start all over from scratch. So I kept being willing time and time again to go a step backwards or two knowing that the reward later on would be larger. And, you know, I talked to people all the time who are like, Hey Scott, I've been in sales for 20 something years. Like I'm locked into this income bracket now, you know, but I don't want to be on the phones anymore. Like, I want to be a sales manager.

I want to, I want to do what, you know, you've done. I want to be a VP of sales. I got a lot of things to teach and I'm like, well, you should, you should do it if you can. And they're like, yeah, but the money. And I'm like, yeah, bro. You know, I hear you, you know, I don't know what to tell you, right? Like you're going to have to be willing to, to do that. So, you know, I, I, I just, I was able to make that those choices early on before I got locked into particular income brackets. And I think that was a big, big help for me. Yeah. I mean, I did the same. It was funny because I went from Black and Decker to Xerox and I was making decent, you know, actually I wasn't making very good money at Xerox.

I was making like $40,000 a year, but I vividly remembered my boy started a, a, a, a startup company, right? And I had never really thought of startups, but I always had that itch. And, and I remember it was coming to the end of the year at Xerox and I had put all this effort into these accounts, right? And if I had just waited till January 1st, I would have gotten a paid a commission check of $30,000. It was literally doubling my salary, right? I would have got, it would have been the biggest paycheck I had ever gotten in my life at that point in my, you know, 23 years old, whatever. But my, my, you know, the startup was like, nah, we need you to start December 1st because we need to get you ramped so that January 1st we can start running.

And I'm like, can, can you just wait until this January 1st? I'm like, then I'll take your bullshit because they weren't going to pay me shit. Right. And, and so I was like, ah, but then, but they were like, look, dude, if you don't take this job, we're going to have to go find somebody else. And I was like, all right, fuck it. You know what I mean? Like, all right, see you later. 30,000. I mean, literally some kid walked into my territory after me, like sign the contract, got a $30,000 check. And I sitting there and I, you know, I had to bite my tongue on it. But, but I, I, I guess the question for me, for you on that one, I didn't, I kind of stumbled my way through for a while, like not knowing what I, and I, cause I think I was so young, right?

Like I didn't have perspective. I just kept working, working, working, and kind of taking calculated risks along the way, but I never had necessarily a plan for my career. But at 27 years old, when you actually got into this and you said, I'm going to start from the bottom, did you have kind of a vision of what you ultimately wanted to be that helped you accept the fact that you had to take a few steps back to make a, you know, more steps forward? Or did you just fundamentally realize that, you know, was it, was it more of a stage thing where it's like, okay, I want to get to that stage. So I got to do this. Or was it like, Hey, you know what? Five, 10 years out or whatever, this is really what I ultimately want to do.

So therefore I know what I need to do to get there. No, it was very much a stage thing with me. Okay. Um, however, once I got to like the kind of senior sales manager level, then I knew like, I want to run sales organizations. Gotcha. Right. Cause it was like, I could see what wasn't working from the sales management, sales leadership perspective in my first organization. And I'm like, I can do that better. And I want to do that better. And this is what I, this is what I love. Right. Like I was, I was doing really well as an individual contributor, but I had a couple of friends that were ICs right next to me. And like, I started kind of helping them and seeing them do well. And I'm like, this is way more rewarding and fun.

Right. And so I knew kind of quick, I'd say after about a year and a half total work experience, I was like, I need to get to the VP of sales kind of level. Like, that's my, that's my goal, you know, and I've been at or slightly above that level for a long time now. And I, you know, you start to get this other itch, which is like, uh, maybe I should run this thing myself, or maybe I should run something myself. Um, and that's where that kind of entrepreneurial spirit starts to kick in. You know, some people get it really early for me, it started at much, much later, you know, um, it's only probably in the last four years, really, that I even started to have these kinds of, these kinds of thoughts.

And only in the last three years where I acted on them. Okay. Uh, can I ask you a question on that? Um, your parents, what did they do as front of the board? Just, just out of curiosity. Yeah. Uh, so my dad has been an accounting professor at Chico state university in Northern California for 40 years or so. Um, he still works there. He's 72 years old now. Uh, and my mom was a part-time nurse. All right. So did they, do you think, cause I look back at my growing up, right? I didn't know I had the entrepreneurial itch until I got into corporate and just felt uncomfortable. And I didn't know why I felt uncomfortable, but it was because when my mom, my dad's been a, uh, you know, he worked for the FAA, he was a contractor for the FAA, but almost always worked out of the house and, you know, went into, you know, Hanscom Air Force base here in Massachusetts, that type of stuff.

My mom, she actually had a job, um, at Wang Laboratories, which back in the day was like Salesforce. Like it was like a baller ass company. Right. And she had a great job there. But when, uh, when I was born, I was nine years after my sister, I was a happy surprise. Um, so, but my mom had been a stay at home mom for my sister and she didn't, she wanted me to have that same experience. Right. So what she did was she quit her high paying job and she started a consulting practice for, um, career consulting. Right. So helping people find jobs and stuff like that. And she worked out of the house. So our living room was literally half of our living room was her office. The other half was our TV. And so I just came home every day and I would see my mom in the office and I would kind of whatever.

And I didn't even think anything of it. Right. Fast forward 40 years, you know what I mean? Or 30, whatever years for me, I'm doing the same shit that my mom was, you know what I mean? My mom and dad were doing. So I think they instilled something in me that I didn't even realize until I got into corporate and literally I, I felt so uncomfortable in corporate, in the corporate structure that, that thankfully my buddy is the one who kind of forced it. Like it started the company cause I'm not a full risk taker. I'm not like a drop everything, live on my parents' couch, eat ramen noodles type of guy. Like I'm a calculated risk guy where if the pieces are there, I'll make the leap. Right. But you know, and, and, and through, you know, and take that risk.

But I'm wondering, like, do you think that you said the itch came for you a little bit later on in your career? Yeah. Do you think it was inherent always? Did you feel that itch early? No. But you just didn't know what it was? No, I don't, I don't think I felt it early at all. I think that I grew up very different than these, you know, my parents were very, they valued stability and security. And early in my career, my, my, my dad in particular would be like, I don't understand what you're doing with yourself. You keep moving from one job to another, you're in sales. That's crazy risky. You're in startups. I don't understand this. Um, so I didn't grow up around that. I think it came out on me by being around more people in the kind of startup corporate world who were entrepreneurial.

Right. I think it developed over time just for me changing, you know, who I spent time around, which makes total sense. Right. You kind of become who you spend time with. Right. Um, and like you, I'm very much a calculated risk taker as opposed to full blown risk. Right. Like, you know, I, I, I very, uh, in my mind, strategically built my brand and my consulting practice and even surfing sales. I built all these side hustles to the point where I de-risked losing guaranteed income on some level. Right. Um, so yeah, I, it, it definitely, I think just developed in me later. And you hit on something I'm, I've always struggled with. And I, this is me asking you for, for advice here on this. Um, you say you surround yourself, right?

You hear every, you hear Gary V talk about it. You hear, you hear all these people like surround yourself with success. Like Gary V says that the number one hack to build confidence in yourself. Like he, he always says that his mom built confidence in him, right? Like, like when he opened the door, when he was nine years old for a woman, his mom like acted like he won the Nobel prize. And so he, he, he was fortunate in that his parents built confidence in him. But he said, the number one way to hack that is to literally surround yourself with people with confidence and positive people. Right. I've always, so I agree with that wholeheartedly. What I always struggle with though, is the people who aren't that like the, the, your friends who you grew up with or people that have, you know, at a certain stage of your life, but that are, aren't necessarily the most driven people you've ever been around.

You know what I mean? Like how have you had to let go of through, through your, and through your career, have you had to consciously let go of, of friends, of acquaintances that were not necessarily adding value to your life? Or how do you deal with, you know what I mean? You know what I'm trying to get out here? Like I, cause I feel like I have a bunch of people in my life that aren't there, that are, that don't elevate me that are, you know what I mean? That are cool, but they don't elevate. They don't push me. There's very few people in my life that, that like literally push me to get better. And so I, I have to take a lot, my wife and I talk about this all the time. Um, I, it's almost like, I wish I was out in San Francisco to a certain degree, because, because that ecosystem out there is such a powerful support structure.

If you get into it, whereas East coast, we're a little bit more inclusive here. Um, but have you had struggled with that? Like, what are your thoughts on that? Yeah. So, um, you know, I live in San Francisco for a long time and I live in, in Austin, Texas now, and I can tell you that people in Austin are much more inclusive than they are. In San Francisco, San Francisco has a rap for being, you know, everybody's going to help everybody and all this kind of stuff. And I got to be honest with you, some of that is bullshit, you know, it's like New York city light, you know, especially nowadays. Um, I don't know how much the location like totally plays into it. I, but I think maybe, you know, where you are in Massachusetts or even where I am, like you might have to work a little harder to do it.

It might not be as easy because you can't just walk outside your office and find, you know, five super successful CEOs from five really successful companies at Starbucks. You, you, you got to reach out a little more, you got to cultivate some of these relationships a little more. Um, to answer your question, I very, very consciously, and some might argue cold heartedly let go of some friendships and relationships and whatnot. Uh, you know, I, I think I developed that, uh, from going through what I went through. I, I emerged from that with a different perspective on opportunity and the limited number of chances and, you know, at bats, if you will, to steal a sports term that we have. And I, I, I almost felt like offended, like, listen, motherfucker.

Like we've been friends for 10, 15 years and I've been dying to get a breath of fresh air and you're still working at fucking Costco. Like, what are you doing, dude? Right. And then, you know, I had to let go of all sorts of people who are just like doing the same drugs and alcohol and, you know, this different kind of lifestyle. I've had multiple friends who have passed away and OD'd, um, you know, I, I cut, I cut a lot a lot of people out and I didn't really stop. Like I, as I kept trying to level up, I would push you. So, you know, if you and I had been buddies 15 years ago, like, and we hit this six figure mark for the first time, I'm the guy who was like, well, how do we get to buck 25?

You know, how do we get to 150, right? How do we get to 200? And I had lots of buddies who were like, dude, I'm cool at like 100 something. Like I'm 30 years old. I don't got no kids or whatever. And I'm like, not me, man. Like I'm on borrowed time as it is. You know what I mean? I'm not even supposed to be here. Like all this shit could get taken from me at any moment right now. So I got to run hard while, while I have the energy and, you know, I want you to run with me, but if you're not gonna, like, I got to find other people. You know what I mean? Do you think you can hack that? So I think you went through a unique life experience that gave you perspective, right? Um, I don't know where mine came from as far as always an appreciation for what I have, because I actually grew up, it was funny, like I worked for Jack and Susie Welsh for a little while to get their online MBA program off the ground.

And Susie asked me to question when I went down to interview her, she's like, well, forget about your job experience. She goes, help me understand where you can, like your background, right? So I walked her through. I was like, well, I got two parents. They've been married for over 50 years. You know, we lived in a decent town in Massachusetts. You know, I had a sister and, you know, a decent house, upper middle income, you know, I went to college and I just kind of mapped out and she goes, she literally stopped. She goes, so you're the one. And I was like, what do you mean? She's like, you're the one fucking person on the planet that grew up in like the quintessential, like 2.5 children with a dog and a white pick.

Yeah. Right. So I don't know. I constantly ask my parents like, Hey, like, what did you do? Right. So I'm, I guess I'm wondering from your perspective, how do you hack appreciation? Yeah. Well, I think there's a difference between, um, appreciation and wanting to do even better. I, you know, if I got deep into my psychological background, I'd be thinking to myself, you know, you might have an issue walking away from that or, or going after something bigger and better than that, because you might view it as a little bit disrespectful or not showing appreciation to where you came from. True, true. Right. And, and I don't think those two things have to be mutually exclusive. I think you could be extremely grateful for the upbringing you had and the opportunities that you had and some of the people that, you know, uh, you grew up with while also being like, how can I elevate this whole group from where we are now to this next level?

Right. Right. And how can I elevate myself? How can I give my kids an even better opportunity and a more stable home than what I came from? Yeah. Um, and it, I'm not saying it, I'm not saying it's easy by any stretch of imagination, but I just don't think that they need to be mutually exclusive, exclusive. Like I appreciate my parents and everything that they did and the stability that they provided for me. They kept me financially above water through my health issues and all this kind of stuff. I love them and can never repay them back for that. But my mission since I got started on this is I'm trying to change the game financially for myself and for my kids and my wife and the next generation.

And I've been trying to elevate friends around me for 15 something years now. You know, I give Richard shit all the time because Richard is somebody who, you know, he'll tell you too, this is not really putting him on blast, but like I will outwork him. I am more ambitious than he is. I am more competitive than he is. And so I'm, I push him a little bit and, you know, he pushes me to calm down and take care of myself a little more, which I need. Um, and so there, there's good, there's good balance there. But, uh, I'm, I guess my point is like, I appreciate everything I have. I appreciate where I came from. I also want more. I want to provide more for other people, especially those closest to me.

And, and I don't, I don't feel guilty about that. No, absolutely. And I don't think you should. Do you practice gratitude? Uh, not as much as I should, but the answer is yes. So for a few years now, my wife and I do this exercise where we sort of write down all our accomplishments for this particular calendar year, and then write out all the goals that we have for the next year. Um, I try to make a point to reach out and thank, um, those people around me and in my life who have been helpful, not just in a like, Hey, thank you. But like, I try to keep repaying it all the time. Um, and I, you know, I take, I'm sure you do this as well, but like, I help people for free all the time, like emails, phone calls, text messages, introductions, like, you know, I got provided opportunities even, even to get the sales job for the first time.

And I, I got to give those opportunities back to people, you know? Um, so that, that's my way of showing gratitude is, is to try to give as many people the opportunity that, that I've had. I love it. So now you kind of, let's talk about what I, what I had, uh, originally had this conversation about. And like I said, I, I, I, I just really enjoy talking to you just in, in, from a perspective standpoint, that's why I'm, I'm asked, you know, a lot of this podcast for me is me learning shit, right? So that's, this is how I learned from, from people who are smarter than me and have, have different experiences for me. But now, now you're, you know, you've kind of a, you said you, you started, you know, after, after your health issues, you started at the bottom, you worked your way up, you found your niche.

Um, and I think that's a powerful thing. I've talked about this a couple of times is like, once you truly find your niche, it's, it's a very liberating thing. Now I had to have mine forced upon me in the sense that when I started my company, you know, seven years, VP of sales, great. We sold it to Staples. I was kind of bored. But then when Staples came and bought us, I was like, oh, cool. Now I'm going to integrate my little $10 million company into a $20 billion organization. Right. And I thought I was the guy. Cause why not? Right. I can figure this shit out. Staples actually had to fire me for me to figure out that I wasn't the guy. Right. Cause I just don't fit in the corporate culture.

Like I, I, so now to your point, you're a zero to, you're a zero to 20 or, you know, maybe a two, five to 20 million guy. Right. That's what you, that's where your niche is. And so now that you found that niche and, and now that you, you know, what made, what drove you to say, because that's a comfortable niche. I mean, you could literally go now like two to three years, you could go find startups in that phase and say, look, I'm going to come in, I'm going to be your VP of sales. I'm going to set you on fire. And I'm going to take you to that next level. What, what, what drove the desire to go off on your own? Cause this is a risky thing. A lot of, a lot of our audience that listens to this, I think has that itch to go off on their own and go do their own thing.

But they're like, fuck, how could I possibly do that? Or who am I to go do my own thing? Like, so what clicked in your head to say, I want to go off on my own now and take that risk. Yeah. There's a few different ways I could take that. Um, a few years ago, about eight years ago, maybe I had a conversation with a friend of mine who is a coach and trainer and consultant and has been for a really long time. And, uh, he sort of said something to me like, wow, you know, you're really an expert in this. And I had never thought of myself as, you know, an expert before. Can I ask how old were you? How old were you when that happened? No, I was 34. Okay, cool. Go ahead. Yeah. 34. And I still, even a few years after that, struggled with the fact that like, wow, I actually, I actually do know a lot about this.

Yep. And I think a lot of people struggle to come to grips with the fact that you actually are an expert in your particular field or discipline. I'm still struggling with that every day. You actually are worth two, three, five, 10x what you're comfortable asking for. Yep. Right. Um, so that part clicked in, you know, a while ago, um, starting a sales org from the ground up is exhausting. It is. If you've never done it before, um, you know, you, you might think, you know, how exhausting it is, but like, it's exhausting, man. Yes. You know, and I have done it a half dozen times now, uh, and I'm not as young as I, you know, used to be. Right. Um, but your priorities change as you get older and your schedule changes as you get older.

Right. So like when my kids were really little, I didn't have practices to go to every afternoon and games to go to all weekend long. Right. And I'm not willing to sacrifice those things anymore in the ways that I did earlier in my career and earlier in their lives. Um, I don't want to travel a ton for the same kind of reason. Um, also traveling a lot, it's a little bit difficult on my, on my health. So it's a kind of long winded way of saying I starting to, I started to have a change in priorities and started to desire some freedoms a little bit more in my schedule and how I run my, my days. Um, and I'm sure that there's plenty of VP of sales jobs out there that, you know, can give you that same kind of thing.

Um, but I also started to be like, well, you know, I kind of know a lot about this stuff and, you know, there are perfect situations out there I'm sure, but 99.9% of companies are not perfect and relationships are difficult inside of companies, especially when you have one, two, three, four, five, six, very, very smart, capable, uh, confident. Uh, stubborn individuals, right? A type personalities. Yeah. A type personalities, right? Like butting heads periodically and whatnot. And, you know, my experience is like, you go, you go start a sales org. It's like year one, people leave you alone. Cause you know, they, they admittedly don't know anything. And like you, you crush things. I'm like, you're a God.

Yeah. Right. And everything is, is gravy. And in year two, like the stakes get a little higher. There's more people involved. They start to try to poke holes in what you're doing and asking questions. Like, so year two is like, well, I still love this, but like, just kind of getting like a little annoying. Right. And then by year three, they're like, Oh, you should be doing it this way. And you know, we, we, we, we read 17 books about sales leadership and whatnot. And like, I don't, I don't know. You know? Right. And so year three is just like a white knuckle, like fuck off. I'm hanging, I'm hanging on here, man. Like, we're still doing good. I still, I still, I love you guys and everything, but like, damn dude, like this is, this is getting tough.

Right. So I, you know, after doing that so many times, it's like, man, I, you know, I need a break for that from that. Right. And the last piece that I'd say is, you know, it is scary to go off on your own. And I'm not at all trying to say that, uh, you know, I'm not, I'm not scared because I've only been doing this for 17 days. I've had a couple of days where I felt like the king of the world and this is going to be great. And I've had about two weeks where I felt like, Oh, like, what have I done? What did I do? Um, I still have that by the way. Yeah. But I fall back on a couple of things. I fall back on, look, man, I have already been through the hardest thing that I'll probably ever go through in my life.

Exactly. So perspective again, like, what the fuck am I afraid of? Right. Like, give me a break. The worst thing that can happen is, you know, you strike out and fail at this particular thing and, you know, you got to do something else. Right. So that's very liberating. I think, and I think if people can just draw back on their own experiences and be like, you know, John, like you've been through something harder before than your business, you know, not working out the way you want it to work out. Right. Like whatever that is for you and whatever that is for the audience, we all have that. It's like, dude, give yourself a pat on the back that you are where you are and you've made it to this particular place.

And you will be okay if your current work situation falls to pieces. Right. And the other thing is, you know, back to the de-risking of yourself, like, if I go do this and it doesn't work, like, I have to find another VP of sales job. Okay. Like, honestly, that's not going to be very hard, I would think. Right. So, like, what am I really worried about here? Right. Right. And so just getting to that place, you know, finally just, you combine all those elements. Finally, for me, it just gave me the courage, really, to just say, fuck it. And, like, now's the time. You know, you said something a little earlier that I think people have to really internalize, which is you bet on yourself. You know what I mean?

Like, as an example, going back to risk takers, like, I was always scared to death from a sales standpoint to take a 100% commission job. You know what I mean? Like, personally, like, early in my career, I was like, no, no, no, no, no, no, no. I'm not going to, like, I have to have a base salary just in case I lay an egg one month and can't pay my bills. You know what I mean? So that was my mentality. Then it was thrust upon me that, and it was a little bit later in my career when I, so Staples, like, even at Thrive, like, even my first startup, I, there, again, I'm not the ultimate risk taker. I'm the secondary risk taker. Like, I'm not the guy who's going to start the company. I'm the guy who's going to come on as number two and light this thing on fire once there's some components in there.

But I wouldn't have even made that switch if they weren't able to pay me a $30,000 base salary back in the day, right? And so, and so then we sold to Staples. Then I got to Basho. Then Basho literally fired all of us on the spot, right? All of us on the spot. And, and everybody else flipped out and said, oh my God, I go to go find a job from a security standpoint. But I, like I said, I'm not the, I'm an opportunist, more of the, like a risk taker. I looked at it and I said, well, shit, this just guy left, this guy just left a $3 million company on the side of the road to die with a product that everybody loves, a revenue stream that's already there. And, and, you know, uh, you know, like, fuck it.

Let me go see, let me go see what I can do there. But what happened was it was now I was a hundred percent commission rep, like note for not by choice, but I mean, I guess I chose it, but I was now, and, and man, I'll tell you, I'm a pretty self-motivated person. If you want to get fucking motivated to get out of bed in the morning, be a hundred percent commission rep and see what you do. And, and I think that is that betting on yourself. Like I said, fuck it. I'm going to bet on myself. I know I can work hard. I know I can figure this out. I'm going to bet on myself. And that year I made more money that year than I had ever made in my career by far. You know what I mean? And so I think that, that, that motivates me.

Now I got, I got to do that myself. Right. But, but I mean that bet, I mean, but I mean that belief in yourself, I don't think enough people have that belief in their self or, and I came the same realization that you did at a certain, that's why I asked, how old were you when you did it? Right. And I think your perspective gave you a little bit more of a jump on it than, than I had in the sense that like, it was around 40 years old for me where, you know, I always say to people in your twenties, you don't know what the fuck you're talking about. Right. So you're always kind of look, I don't want to say asking for permission, but you're always kind of looking up and saying, is this right? I don't know.

Right. In your thirties, you're, you're, you're a practitioner enough. If you stay in your field that you start to kind of say, okay, I'm figuring shit out. But in your forties, you start having conversations with people where you just start talking and people like, Oh, that makes a fucking ton of sense. And you're like, what? Like that was like that. Like that, that seems like pretty fucking common knowledge to me. Right. And they're like, no, no, no, dude, that say that again. Like that was fucking genius. Right. And I'm like, it's literally around 40 years old. I was like, fuck, apparently I know what I'm talking about here. You know what I mean? But still to this day, I, I, I am inherently uncomfortable with how much people pay me to stand up and talk.

Right. I, I, cause I'm just like, well, fuck, this is just me sharing some stuff that works. Like who am I to sit there and be on stage and, and, and have people pay me for this stuff. But when you see the difference that it makes, you know what I mean? When you, when you get those emails back from those reps, that's why I'll go, I'll, I'll get the shit kicked out of me and I'll travel to Singapore for a day and I'll, I'll, I'll take a, I'll sleep in an airport and all that other stuff, which is fucking horrible. But that one email that I get from that rep saying, John, that fucking training changed my life. Like no shit, you know, after your training, this is what happened and this is where I am in my career right now.

I know you probably don't remember me, but that, that, if I get one of those a month, right. And I get more thankfully, but if I get one of those a month, I'm like, this is fucking worth it. Yeah. I totally relate to that. Those, those, those moments are so special and it's just an, it's enough to keep you going. I mean, I have a, I have a whole folder where anytime I get an email, I'd put it in that folder and it's, and it's a, it's a gratitude. One, it's a flip side gratitude. Right. And it reminds me to be grateful for what I have and what I'm doing and help me keep going. Right. Yeah. Yeah. Love it, man. Well, look, we're, we're coming up here. Fuck. I could talk to you for six hours here.

Um, uh, but so let, but let's talk about what you're doing now. Cause I, I do want people to, to understand like your niche now of what you're doing. So, so if there are people out there listening where they're at this stage of their business, uh, to, to bring you on in, because man, I like, like I said, I'm, I, if I was at this stage and I, you know, I'd bring you in in a fucking heartbeat. So what are you focusing on right now? Yeah. I'm, I'm, I'm focused on working with companies in that zero to 25 million ARR space who, you know, are maybe trying to go to market for the first time or have gone to market and, um, are struggling a little bit to kind of get off the ground or they're looking for somebody to kind of bridge the gap between where they are now and making their first head of sales hire.

Um, those are the people, those are the companies that I'm looking for. And the work that I do is with founders and CEOs and sometimes heads of sales. Um, a lot of, you know, my network is so big now all across the country. Um, and even in certain parts of the world that I've been able to wrap a lot of recruiting services into, to my offering. Oh, cool. Um, so my role is, is more of like a strategic advisor. It's, it's not a sales trainer to the stars type, type thing. You know, I want to go in and help you operationalize your, your sales machine and get all this stuff right. So you're, you're set up for success. Um, that's, that's really who I, who I feel like I am. That's my niche, my sweet, my sweet spot.

And that's who I want to work with. Yep. Um, is it mostly tech or is it across the board? Yeah. One more time. Is it mostly tech or across the board? It's across the board, but it, but it is primarily tech and SAS companies. Um, but it is a little bit across the board. Um, and then, you know, I'm, I'm growing surfing sales, you know, this, I haven't really announced it publicly yet, but if you looked at the surfing sales.com website, um, surfing sales four is up. We just booked the houses last week and, you know, getting everything dialed in. It's February 24th to 28th. And we'll probably do, we're doing at least two, maybe three other ones in 2020. Um, so, you know, just kind of keeping that, that going and growing that, you know, a little bit, a little bit slowly.

Um, and then I'm really excited about, and you know, I know you'll like this cause you, you just released your book, which is fantastic by the way, and I can't wait to wrap it and give it to my niece and nephew and my, and my kids for Christmas. You got them, right? Did you get them? Oh yeah, I got them. Yeah. Okay, good. Yeah. I got them. They're, they're wrapped and in my closet already hidden away for Christmas. Um, so I'm, I'm working on my next book and, uh, my next book is, um, I don't really, I don't have a title yet, but it's basically like, you know, so you want to be a VP of sales and it's going to be cut up into a couple of different sections. It's kind of talking about what you need to get good at in order to be a VP of sales and get that gig for the first time.

Yep. And then kind of the good and bad and ugly and some war stories of what it's actually like to be a VP of sales, right? The pressure, the stress, the ways that people might try to pull a fast one on you, all this kind of stuff that is behind the curtain, not advertised too publicly. Um, and then the last section is like, I want to speak to people who are hiring VP of sales and try to change this dynamic a little bit where our lifespan is like 16 to 18 months. And, you know, I think it's a real travesty, um, that people in the VP of sales roles have the smallest job security I can think of maybe other than being a professional football coach or something like that, right? Um, you know, how come marketing executives and VPs of technology and VPs of product, like you trying to tell me they don't miss goals and deadlines, right?

Come on, man. Right. But you don't, you don't see their job security in the same way as VP of sales. So I'm going to talk about, you know, all those kinds of things. And, um, I'm pretty excited to, to get to it and get that book out here. I, from what I can tell, there's not a lot of literature out there speaking to these kinds of things. And I feel, uh, I feel a bit, you know, right time, right place coming out of what I, what I've, what I've been doing for the last 15 years and still fresh on the pulse of everything. So I'm excited to try to get that out next year. Awesome, brother. Well, definitely keep my eyes out before I let me know when it lands so we can push it out there. All right.

Will do, man. Awesome. Well, it's been great talking to you, man. Um, if people want to find out a little bit more, it should do, what is it? LinkedIn? Like, where's the best place to hit you up on? Yeah. I mean, I'm all over LinkedIn for sure, but, um, you can check out surfing sales at surfing sales.com. And, uh, my website is scottlease consulting.com. And, uh, yeah, I'm happy to talk to anybody. I, like I said, I, I follow up with people religiously who reach out to me. So reach out, happy to get to know you in chat, see if I can be of use to you. Awesome. All right, everybody. Well, hopefully you, you enjoyed this conversation as much as I did and yeah, check out Scott, what he's doing, man.

Cause across the board, uh, just a lot of lessons learned a lot of, a lot of, a lot of stuff to learn, um, and follow that journey. So anything I can do to help Scott, let me know, but, uh, hopefully everybody else can, uh, can jump on board as well here and join. All right, John. Always good talking to you, man. Hopefully, uh, hopefully, hopefully we can not just beat the spread, but also win the game next time. Yeah. So we'll, we'll, we'll do a bet. We'll, so I will do a little video with a, with a bills. I'll find a bills hat. I got to order it on Amazon right now, but next, next bet we'll, we'll bet something legit and, and we'll do something legit. And by the way, I, I do promise that I will get to surfing sales one of these days.

I promise I do. So let me know what the schedule is. All right. All right, bud. All right, everybody. Well, thank you all so much. Um, just like I always say, just if you don't do anything else today, go make somebody happy, right? If you make somebody smile today, you know, you had a good day. All right, everybody make it a great week. Thank you all very much. Make it happen.