Sales Hustle is now Sales Transformation
Feb. 28, 2022

#254 S2 Episode 123 - Live The Life You Want with Bobby Dysart

In this episode of The Sales Transformation with Collin Mitchell podcast, Collin talks to Bobby Dysart. Bobby talks about his sales journey and how he pursued the life that he truly wanted to live. Bobby's experiences from starting as a door-to-door salesman to becoming a consulting VP of Sales for various companies has taught him that everything in life should be done with intentionality, and he's here to share his story.

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  • Cold-calling 97 doors in the first day of the first sales job
  • Going back to the basics after experiencing a setback
  • Getting back in the groove and achieving success in software sales
  • Quitting VP position to pursue consultancy 
  • Introducing Quotaless 
  • Salespeople should be living better lives, but they're not


Bobby: "Companies like up to 50, 75 employees  they really have a hard time nailing the VP of Sales hire. Most of the time  they don't get it right. They hire somebody too big, too expensive, maybe even overqualified for that exact stage in time. 

Bobby: "I think there's an element of consulting that I think could be presented into the W2 world and the world of work as it's always been where there's just a transparency of  either you're doing your job and getting it done and the company is helping you do it that way, or not. And it's okay if it's not happening, it's not working out. Let's figure something else out."

Bobby: "With consulting, having that month to month setup has really given me that clarity and transparency to say hey, every month either I'm creating that value or I'm not, and I want you to have the flexibility to tell me when I'm not. Hopefully give me an opportunity to correct it. But I don't want this to be something that just doesn't feel good because we signed something that we thought was gonna work out better than it does." 

Bobby: "People in sales should be living really really awesome lives and they're just not. And I've been one of those people for a long time."

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Learn more about Collin in the link below: 

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[00:00:00] In the world of sales, you either sink or swim or breakthrough to the next level. My name's Colin Mitchell, and this is sales transformation, a new kind of sales show designed to bring you through the epic life-changing moments of elite sellers. So you can experience your own sales transformation.

[00:00:24] All right. Welcome to another episode of sales transformation. Fire it up for today's guests. I've got Bobby Disert on a long friend coming on the pod today. He's got some interesting things going on that we're going to talk about. He's got a very successful story, which we're going to dig into an interesting path.

[00:00:43] He helped start up founders, sales leaders, and software sales professionals lives the live, the lives that they want. He's a podcaster, he's an author and a very good friend, Bobby, welcome to the show. How you do. Colin. I'm great. It's uh, it's wonderful to finally get on here. I think I've been just like bumping elbows to try and get in here, but, uh, thanks for making some room for me.

[00:01:06] Yeah, man. There's always room for you. And who knows probably have you back again. I'm sure. Um, so yeah, I want to kind of go back. Where did your, where did your sales journey start? Or even if you want to take us back a little further than that to just give us a little context. I mean, when I think of my sales.

[00:01:24] There's nothing more that comes to mind. Then my first day in Los Angeles. After a week of training, I went out to sun valley. Do you know where sun valley is gone somewhere in the valley about 20 degrees hotter than what I'm used to? Yeah, so it was, it was July, I believe so. Yeah, it was, it was almost a hundred degrees.

[00:01:45] It's just north of Burbank and Glendale. Um, very industrial neighborhood and I cold called 97 doors in a suit. And I thought I was on top of the world cause I set three appointments. So that's where my journey begins. Uh, with sales, uh, at that time I had just moved from Ohio and, um, the first job I could get, uh, during the recession that nobody told me, I was in, um, was selling communications packages, uh, for, for, and there were B2B communications packages and, and we went door to door.

[00:02:19] Wow. So it was a little bit warmer than Ohio. Yeah. It's like a hundred degrees. You're knocking on doors, probably sweating a little bit, probably loving life. I mean, bro, I really did. And you know, we, we were taught to, to cold call 50. I think that just shows like, you know, going the extra mile 97, just sort of shows like from the beginning I was locked in to like, Uh, the idea that you just get out of sales, what you put into it, you couldn't just do three more, more, three more doors.

[00:02:54] Your story would be so much more interesting now, just kidding. You would think that, but like, it took so much to get to that 97. Like I think I was out there until like six o'clock and I still had to go back to the office to share what I'd done with my manager. Uh, and that meant getting on the five and running into a bunch of track it to traffic 90, get back till seven 30 or eight.

[00:03:16] And you had to get back and get those outta boys, man. That's right. That's right. And, and, and, you know, it's funny, it sounds like really hard and it was, but, um, I ended up staying at that job for four and a half years, um, because, uh, I was just super. Grateful for the leadership that I was surrounded by. I ended up advancing really quickly.

[00:03:37] By age 27, I was running a sales office of 30, um, where everybody else was in their early twenties. And I was way in over my head, but just having a blast and making good money. And it was a great way to start out my sales career. Wow. Wow. Okay. And I always have so much respect. I've never, I've never been a door knocker.

[00:03:56] I've never cold called via doors. And. I would kind of wish it was part of my story. Sometimes I know I've said this before, but as like, man, if you can survive knocking on doors and do 197 in a day and do it for four and a half years, like what can't you sell? That's right. No, I mean, it was really fun. To, to just think back to like how quickly, you know, I sound like the old guy now, like just how quickly sales has changed, but it really has, you know, my wife's in sales as well.

[00:04:31] And her first experience was at my, one of my favorite startups that I worked at company called blue. Um, and she was an STR that had showed up and her first day, you know, she's, she's answering, she's replying to inbound leads from Australia and getting on calls with folks from down under to try and sell them like sort of starter packages.

[00:04:52] And anything that she brings in is just icing because we weren't really going after that market at the time. And then, you know, she, she quickly got into an AED route. I'm sorry, what a different experience, you know, at the, and at that point, like there was tons of sales jobs in tons of software, uh, and it's just really, really changed.

[00:05:13] So, uh, yeah, it, it, it, it definitely taught me a lot. I'm glad I started that way, but I'd be lying if I didn't say I was a little jealous of how my wife entered into the sales. Yeah. Yeah. I could see that. You're like, you've got it made, you know, it's kind of like those parents, we used to have to walk in the snow mile with no shoes knocking on doors, bro.

[00:05:36] And, and that is where it fell. You know, stuff just kinda funny to look back on and thought about that in a while though. That's good. Yeah, it's funny. I had, I had Katie on the, on the podcast. Right. And he's like, um, one of his first, uh, he hasn't actually been in SAS that long, right before he was at a snack, a snack company where he sold snacks as a service.

[00:05:59] Right? Yeah, that's right. And he's like, man, once I got some software, like, forget it. I was selling snacks in a box. Like, you know, I mean, it's funny to say that I remember my. Two months in to a BlueJeans AI, I blow my quote out of the court, like just blown it out my first quarter. And we had a ton of accelerators and all I really did was like dig into Salesforce.

[00:06:27] And there was just like thousands of leads. And I just sorta sent them a bunch of emails and I call it herding the cats, and I just made a ton of money. And I was just like, I went back to, uh, to Ohio on Christmas that year. And I was. It's for real, like, is this a real job? I just, I just sold these usernames and passwords over email and over video conference and made more money than I did any time, you know, cold calling all those doors, um, out in the heat and, you know, it's, it's definitely a different world, so I can understand where, where Katie's coming from.

[00:07:00] Software is just a whole nother bag. Yeah. So what, tell me a little bit like, okay. So after knocking on doors, you know, spending some time there leading a team, What were you doing at blue jeans? What role did you have there? Well, I started as an individual contributor and it was because I was coming off of a year and a half hiatus where I tried my own startup.

[00:07:21] Um, and so I tried my hands at, uh, at entrepreneurship, opened up a web company. He got some funding, um, alongside a really good friend and, and, and a, uh, a gifted programmer. And when I showed up to blue Jean. I was just out of money, man. I was in debt and, um, had, spent, spent most of the money I got from my four and a half years, um, uh, at that previous company.

[00:07:46] And so I just came in and not only did I need money, I just wanted a break from trying to think. All the things that you have to do as, as an entrepreneur, like, you know, the, the, the list is long and, you know, there's really no way to figure it out, except figuring it out and going through. And so when I showed up to BlueJeans, I was just like, man, just give me a territory.

[00:08:07] Uh, it happened to be Southern California, uh, and let me go to work. And, um, and yeah, so I was selling to companies of, I think, between, let's say, let's say 720 500 employees. It's kinda like a mid market. Yeah. Okay. And so that was probably a little bit hard. Yeah, just kind of like after leading a team, you know, having the startup thing that didn't necessarily work out, but then also maybe a little bit relieved drivers, like just give me something to sell.

[00:08:36] So don't worry about all this other stuff. Right. You know, it's funny you say that the humbling piece, I mean the humbling piece was, was failing at the startup. So, so, you know, going into blue jeans, I was actually licking my wounds a little bit and just being like, I was starving for leads. Too, you know, I, you know, as, as I'm sure, you know, entrepreneurship can be lonely, um, particularly if it's not going well, if you're not figuring things out.

[00:08:59] And I was used to those four and a half years, I was surrounded by, you know, really strong executives. You know, it was a bit, it was a big company, it was a publicly traded company. And I thrived in that environment. You know, I thrive in an environment where I'm surrounded by people, surrounded by energy, surrounded by leadership.

[00:09:15] And so when I went into. I was like, nah, just, just give me some more of that. Um, you know, make quick friends with my VP of sales, my VP of channel. Um, I even incubated a, sort of a, a small training, uh, training group, uh, for all the younger guys. Cause I had gotten a lot of training and they didn't have that at that store.

[00:09:35] Yeah, blue jeans. It was moving so quickly. And so I just, I just sort of grabbed a shovel and started digging and, and was like, this is great. It's just great to be back in, um, in, in, in this kind of environment and trying to fix. Yeah. Yeah. How long did it take for you to just kind of get back in the saddle and feel like, ah, this is what I was built to do.

[00:09:56] Not, not long, not long. Um, again, you know, what was great about coming into that environment was I just had some. Um, tools, tactics, and, you know, scar tissue just built into my being at that time. Then when I went in there, you know, it's, it's interesting. I think it startups and I saw this happen a lot. Um, you know, startups move so fast.

[00:10:19] They're not there. They're sort of processed light training light a lot of times, and there's a bit of figure it out as you go. I think that's just sort of par for the course of that kind of role pros and cons to that a hundred percent, a hundred percent. Um, and for me though, I was like, I'm just going to do what I always did.

[00:10:38] Right. Which I got on the phones a lot. Um, I knew that I could control my activity above all else. I knew that I didn't know that much about, you know, enterprise video solutions and integrating. You know, different, um, you know, central control units and all the different things. I just knew if I talked to a lot of people, someone was going to take note of my, of my personality and sort of the product I was representing.

[00:11:05] And it worked out pretty quick. And. Yeah. Okay. And then, so talk to me a little bit about your, your time there at blue jeans, you know, first experience with SAS. Um, what was that like and what roles did you hold while you were there? Yeah, so, um, again, I, it was an education and where the world is going from a, both a sales perspective and a technology perspective.

[00:11:29] And so I just loved it. I lapped it up. Um, I quickly figured out that the best role I could play. Is helping companies that want to get the most out of the technology do that. And so I, you know, I found a couple of really key buyers actually that, that were partners. Um, they really, really were partners.

[00:11:49] They were like, Hey, if you could help me figure out how to do this. And then I'll, I'll, I'll expand, um, doing that. And, and really early on, I was just lucky enough to partner with a couple of CEOs on some, um, some deals that re. You know, hundreds of thousands of dollars in revenue and expanded across thousands of employees.

[00:12:08] And that started to just give me this vision of like, ah, this is, this is really a deployment sort of a, a job of creating value across large companies. And I just, I just repeated that recipe, um, for, I'd say my first year and a half. And then I, I, I took on a channel role where I was helping deploy, um, Sales methodology and our product across, um, big partners like CDC.

[00:12:35] It was probably one of the biggest ones and that was a whole nother learning curve and a really exciting experience. I was, I was traveling to offices. I was working with other salespeople. I was sort of using my, my, my managerial muscles too, which was really great. Um, yeah. And then I, you know, I became sort of a, I think I definitely became a leader in a, in a mainstay at the organization.

[00:13:01] I think I was there. And how long was I there at least four years. Um, and it was a really great experience. And, yeah. Where was the, where was the company at like revenue wise when you first started and where was it when you left? There was, I think, I remember I was like sales person, 19, maybe the 90th employee, something like that.

[00:13:24] And when I left, there was like 600 folks and revenue wise, I think it was like, 20 million to a hundred million, we'll say 20 million to 80 million. Maybe it sounds like it's probably a little bit of a wild ride. Huh? It was, it was in more ways than one in more ways than one, like, um, I saw in short order us going from this small startup that like can't, that, that everything we do is really great because it's never been done to an end, but nobody knows us.

[00:13:55] And we just have this funny name too. Oh my gosh. You guys are like really making waves and you are the king of this very small castle called, um, ubiquitous, you know, virtual video to. Oh, my gosh, there's this crazy company called zoom that you had never heard of before, that is going to eat your lunch, dinner, breakfast, whatever.

[00:14:17] And it, it, it, it happened so fast that we were like, we were nobody, we were definitely somebody to, we were getting left in the dust and like four years. And it, it was. Well, not to mention meeting your wife there. Oh yeah. And, and, you know, I got caught up in an inner purse in a inner company relationship that ultimately was the love of my life.

[00:14:37] And one of the main reasons I live, so yeah. Wild ride for sure. Yeah. So talk to me a little bit about. The work that you do with folks today and like how, what sort of led up to that? And then we'll kind of get into like some of the changes that are going on. Yeah. So in 2019, I left my job as a VP of sales, uh, on a Friday.

[00:15:02] And then on Saturday I got married. Uh, and then two days later I went to Bora Bora for two weeks with my wife. So I'm sitting, I remember this specifically, I'm out sitting on the back deck. You know, we're overlooking the water in, in those, uh, over-water bungalows, Tracy's asleep, I'm drinking some wine and it was, it was crazy.

[00:15:23] It was like one, one night. I'd be like, man, I'm so lucky. I'm the greatest, this is the greatest thing in the world. And then the next day, or the next night, it'd be like, holy crap. I can't believe I quit my job. Like, what the heck am I going to do? But, um, I knew in the back of my head, I wanted to do some consulting that, uh, and I always knew I wanted to get back into entrepreneurship and I thought con consulting.

[00:15:45] Yeah, it's sort of a low barrier to entry to entrepreneurship. It's sort of a smart way to do it. Um, and I had managed to talk my, uh, my current employer into bringing me on part-time as a consultant and sort of helping me, help me live out this dream of entrepreneurship. So when I got back, I started talking to my referral network.

[00:16:05] Um, to just talk to early stage companies that needed stand in sales leadership. Um, there was another thing I think I noticed with the market at that time is, um, is companies like up to 50 employees up to 75 employees, they really have a hard time nailing the VP of sales. Most of the time they don't get it right.

[00:16:24] They hire somebody too big, too expensive. Um, maybe even overqualified for that exact stage in time. And I think the tenure is like 15 months something crazy. And so I offered this different solutions. Let me be a bandaid, hire me month to month a fraction of the cost. Let me install, you know, your, your first sales model, your first sales software stack, hire your first sales people.

[00:16:50] And let's see how far we can get. If it doesn't work, you can fire me a lot easier than a full-time VP of sales that you invest a lot of time, money and energy in. And the market responded really well. I picked up four or five clients. That had me on retainer, uh, very quickly. And, um, yeah, it's, it's, it's been a great ride.

[00:17:09] That's really still how I make my money today. Obviously I've got interested in a couple other paths along the way. Um, but, um, I'm super grateful for those initial customers and just, just the lifestyle that it's afforded me. Um, it's, it's been really great and I've learned a lot. It sounds like such a super risky business model though.

[00:17:31] Fire me whenever you want. Well, if you do good work, you don't get fired. So exactly, exactly. You know, and there's two reasons for that. Number one, you know, 20 safe risk, right? Like, again, this is a guy who, who quit the day before he got married. Um, you know, I, I, you know, there's, there's something to, I think, leaping in the net appearing that, that I just hold true.

[00:17:53] Um, it's worked for me. Forever. I left for California the day after I graduated Ohio state. I didn't have a job. Um, I landed on my feet again pretty quickly. And you know, about the 97 doors. Um, the second thing with regards to risk with my clients is. I think it's twofold. One, like I don't have the, you know, th the attorney resources to go hunt them down, to keep them locked into a contract that they signed and be, I don't wanna, you know, be it.

[00:18:22] I want it to be very, I think there's, there's an element of consulting that I think could be presented into the W2 world and the world of work. Um, as it's always been. There's just a transparency of like either you're doing your job and getting it done. And the company is helping you do. That way or not, and it's okay if it's not happening, it's not working out.

[00:18:44] Let's figure something else out. And with consulting, having that month to month set up has really given me that, just that clarity and transparency to say, Hey, every month, like either I'm creating that value or I'm not, and I want you to have the sort of flexibility to tell me what I'm not, hopefully give me an opportunity to correct it.

[00:19:04] Um, but I don't want this to be something. It just doesn't feel good because we signed something that we thought was going to work out better than it does. Yeah. Yeah. I mean, I'm sure it's like a fresh breath of air for, for your clients. Right? For, because a lot of startups are in that sort of phase where, you know, they, those, those first essential hires or that first sales leader or a fractional sales leader, or, you know, consultant is, is really key to growth.

[00:19:34] Like it can either. Take them to the next level, or it could be a bad relationship that really hurdles growth. And, you know, doesn't allow them to maybe raise money or, you know, folds the company like those, those are like really key decisions based on. You know how, where the company goes next and, you know, having that flexibility and being able to make that decision, um, and not, you know, maybe overextend themselves or, you know, get into a relationship or hire actual sales leader.

[00:20:03] That's, you know, probably more than they could afford. Um, it isn't quite needed yet. Um, can, can hurt the company in a big way. Yeah. I mean, the stacks are tracked. The S the chips are stacked against. Entrepreneurs in, I want to be part of the solution, not part of the extra obstacles that, that they're already facing.

[00:20:26] So I, I truly know. I think you mentioned it, right? Like the average tenure is super short. It's like, I think it's 15, 18 months or something like that for, you know, like a VP in a, you know, earlier, you know, sort of startup, right? Yeah. And I think it's just matchmaking. It's not really anything on the candidate.

[00:20:43] And anything on the company, it's just a bad match from the beginning where usually how I see it is, is the VP is maybe, you know, a lot of times I see clients hire a big splash VP from like Workday, Salesforce, Cisco, what have you. And they're used to operating at a level that. Way different, you know, they have resources, they have personnel, they have built-in strategies, partnerships, et cetera, for budgets, much larger budgets.

[00:21:10] Right. Right. And then, um, conversely on the company side, they, you know, they a little goes a long way. Like, you'd be real surprised con how far. Um, you know, just, just installing like a training program, like just training every, you know, once a week for 30 minutes on a few specific items, how far that goes, just helping, um, you know, draft a different set of pricing goes or, or just figuring out like, where is our time best spent, um, in terms of like account focus and prospect focused, like those, just those getting down in the nitty gritty and doing those little things can really like when you're talking to.

[00:21:47] No 500,000 revenue or a million in revenue like that can lead to doubling that revenue, like pretty quick, uh, pretty easily, pretty effectively. Oh yeah. And, and, and the biggest challenge is like, you know, hiring some big name, VP, somebody who, you know, can Excel in a company like that with, you know, where it's maybe going from, you know, 10 to 50, that's not the right person to take you from zero to five.

[00:22:13] Like, that's a totally different person, you know, unless they've gone from zero to five or five to 10 or 10 to 50, like those are very different people that have very different skillsets. You know, somebody who can take use here at a five is a much scrappier person and knows how to, you know, implement those little things.

[00:22:29] Like you mentioned, that can go a long way for a company at that stage. Yeah. I mean, unfortunately for better, for worse, I was just thinking about this. I realized I've gotten really good at helping people go from like zero to one or, you know, 500,000 to 2 million, you know, one hired at 10 and it's just hard work, uh, starting from scratch.

[00:22:51] It. It really is, but, but I agree with you a hundred percent and, um, I've gotten pretty good. Yeah. So tell me a little bit about quota lists. What is it? What's, what's the reason behind it, you know, uh, give me, give me all the goods, how people understand and where they can learn more about it as well. Yeah.

[00:23:09] So quota lists is an evolution of my own podcast and newsletter, uh, formerly called student of intention. And you know, that podcast and newsletter was sort of bore out of my own awakening for lack of a better word. Um, And that awakening has just led to this focus. Um, and this just almost the zest, this obsession with living with intention, with figuring out like why out of the billions of people in the world.

[00:23:37] Some people just seem to live exactly how they want and others just dream about it. And now I've just brought that into the focus of the sales community, because I think the sales community on one hand could really, really use help figuring out how. How to live a sustainable sales life and feel good about their work while they're making money and be, um, they're, they're most primed to do it.

[00:24:04] You know, sales could be the most, it sort of lends itself to the most flexible work-life balance because if you get the numbers there, you're good. Right. Um, you can do it from anywhere. We have all these different sales tools, et cetera, right. People in sales should be living really, really awesome lives.

[00:24:24] And they're just not. And, um, and I, and I've been one of those people for a long time, you know, I think I didn't really explain why I quit my job the day before I got married or the day I got married, but oh, I can only imagine finding that both ends, right. I mean, which is typical and especially in a fast paced, you know, SAS, it's growing like crazy and you know, it's hard, you know, sales people, and I've experienced this even firsthand.

[00:24:50] It's very common to. Uh, you know, attach yourself worth to your number, right. And you're only as good as last month. Number last quarter's number. And so, you know, naturally. Most salespeople, um, are workaholics and don't get to enjoy life as much, uh, because they're obsessed with their work. Yeah. Yeah. So, um, I'm trying to work on that problem.

[00:25:14] It's a big problem too. You know, I think we've all heard the different stats out there that like 60 or 70% of sellers aren't hitting quota. Right. Um, you know, the burnout rates, you hear all the stories, et cetera. You know, part of me is, is, is really just invested in trying to tackle that big vision, that big problem.

[00:25:33] And today I'm starting with what I already have sort of groomed, which is a podcast, a newsletter. And, um, I'm also doing some in-person workshops with teams. So. That's that's kind of the evolution of quota lists and it's, it's officially launching next week. So thank you for nice. I'm excited, man. Uh, I know I've, you know, we've had a few conversations behind the scenes a little bit, so I'm, I'm very excited to start, you know, seeing, uh, seeing this happening for you.

[00:26:04] Um, I know that you're gonna be doing some awesome work and helping folks, where can they learn? Quota Um, just go there, follow me on LinkedIn, Bobby dice R uh, but you go to, please subscribe to the newsletter. It's going to come out weekly on Tuesdays. It's totally free. Um, I've been writing my other newsletter for almost a year and a half now, and I've learned a lot.

[00:26:27] I promise I'm going to pack a ton of value. Keep it concise, extinct, um, good stories and good things. You know, bill confidence, sell more and get your time back, get a little bit more freedom and a. Awesome. And I love it. We'll drop the links for everybody there in the show notes. Bobby, thanks for coming on.

[00:26:45] If you enjoy today's episode, please write us a review, share the show with your friends. It really does help us out. And as always, I'm listening for your feedback, you can go to sales, transform. Dot FM drop me a voice DM and I will get back to you. Hey, you stuck around that tells me you're serious about your own sales transformation.

[00:27:06] If you're tired of doing things the old way and want to get started in your journey with other people on the same path, head over to sales,, and crush your numbers on your leaderboard. Yeah. It's free sales cast, doc community. Send me a DM with your best pitch and mention this ad. And I might even give you free access to our best templates.