Make It Happen Mondays Podcast

Kyle Porter on How to Stay Consistent as a CEO from Startup to Acquisition

with Kyle Porter

April 4, 2022

This episode of Make It Happen Mondays features a conversation with the CEO of a sales technology company who recently led a partial acquisition of the business by a private equity firm at a multi-billion dollar valuation. The discussion centers on how he stayed in the top role from the company's earliest days through that milestone, how his personal values and communication style evolved without losing his core identity, and where he sees sales technology and skills heading over the next several years. It also touches on personal reflections around gratitude, decision making, and staying grounded through major life and business changes.

What you can take from it

Leadership consistency through company growth stagesBalancing authenticity with personal evolutionMission driven decision making and killing a profitable productThe future of sales technology and unified workflowsSkills future sales professionals will needGratitude and perspective as tools for resilience

Questions this episode answers

How did the CEO stay in charge of his company from startup through a major acquisition?

He described refusing to pigeonhole himself into a single stage of growth, treating feedback about his blunt style as something to adapt rather than defend, and committing to learn faster than his own experience. He also credited surrounding himself with strong co-founders, investors and staff, and building organizational health into the company's operating rhythm.

Why did the company shut down a profitable early product?

The product was being used by sellers to send mass, impersonal outreach, which conflicted with the company's founding mission around respectful, sincere selling. Even though it was generating meaningful cash, the founders judged it would never scale to the size of business they wanted to build and chose to abandon it rather than compromise the mission.

What skills will sales professionals need in the future according to this episode?

The episode argues sellers will need to become genuine experts in whatever they sell, able to teach and earn trust with buyers, while diagnosing specific customer problems and guiding them to solutions. As technology takes over data storage and routine tasks, human strengths like creativity, intuition and emotional connection become the differentiator.

How can someone decide whether to stick with a hard job or move on?

One approach discussed is imagining yourself much older looking back and asking whether the current decision fits the life you actually want to build, rather than judging the task only by how it feels day to day. Having a clearer long term vision makes it easier to tell whether short term discomfort is worth pushing through or a sign to change direction.

Read the full transcript

A conversation between John Barrows and Kyle Porter, recorded April 4, 2022. This transcript is machine-generated and will contain errors. Where it disagrees with the audio, the audio is right.

Hey, everyone. Welcome back to Make It Happen Mondays, where we talk about sales, business, entrepreneurship, personal growth, mental health, and everything in between with guests who I truly respect and I believe make a positive impact on the world around us. Now, this conversation I have been waiting for for a while. Now, you've heard him on the podcast before, my good friend Kyle Porter, CEO of Sales Loft. Kyle and I go way back when he first started Sales Loft and I first started JV Sales. We got together and we've been friends ever since. And talk about a rocket ship. He just sold his company or a portion of his company to Vista Equity Partners for $2.4 billion valuation. And guess what?

Kyle has been the CEO from day one. And that is extremely rare, which is what we talk about. I talk about how do you stay consistent as the CEO of an organization from startup all the way through such a massive acquisition like that? Because most of the time people kind of fit a very specific part of that growth and Kyle's been able to stay consistent all the way through it. We also talk about how he's changed as an individual, not necessarily his core values and how that's always guided him, but how he's had to change his thought process and how he interacts with people. Talks about what he's excited about in the future and what this whole sales tool world is going to look like moving forward and the future skills necessary to be an effective sales professional based on what's happening out there.

So this conversation was a blast for me. I learned a lot from Kyle. He's one of those people that is behind the wall and in those meetings that I'm just not in. And so I got a lot of that information out of on this one. I hope you enjoy it. Enjoy the show. What's popping y'all. Huge thanks to our partners, Gong, Proposify, and Vidyard. As you know, Gong provides great recordings for reviews and coaching, but it's also a great data source that helps you know where you can improve and where you should spend your time making these changes that are essential for business growth. Knowing where to spend your time is super important for any frontline rep or leader. Proposify simplifies the proposal and contract processes for both buyer and seller.

What a win. E-signature, inline editing, and all the frills that come with Proposify get me real excited about paperwork. Vidyard is always out there creating incredible content, but even more than that, they are delivering a wonderful product to help frontline sellers create better videos for prospecting and closing more deals. Learn more about all the things that Vidyard can do to provide for your sellers as they get more comfortable using video in their sales cycles. Let's pass it over to JB now and see who's coming in with him this week. See you soon, everybody. All right, let's just get right into it. I'm here with a really, really dear and good friend of mine, Mr. Kyle Porter. I don't even want to like CEO of sales love, but just a good friend.

Kyle Porter, how the hell you been, man? How you doing? Well, I'm excellent and I always get very excited when you invite me to come on and spend some time with you. You know how much I admire you and all that you stand for and stoked to have a conversation today. Yeah, man. And this is going to be a fun one. We've been, first of all, like I always tell this story for people who've listened to this podcast for a while. They've heard it before. It's like we legit started when you started your business and I started mine and somebody in my training sent you one of my emails and you wrote a blog post about it. And then I reached out. I was like, yo, I trained that kid, you know, any chance, you know, CEO.

And then we just, one thing led to another. And the thing that I've always appreciated is the shared values piece of it. Cause it was very evident as soon as we got together that we, we saw things very similarly, like from a core value standpoint, not necessarily from a strategy business, but, but just from a core being a good person, and, and what we're here on this earth to do. And that's why I think our relationship has lasted over the years and it's been stronger than most. So. John, you had a quote, you said it a long time ago and I wrote it down. It stands in my Evernote under my quotes folder. And it says, remember that you're not better than anyone else and nobody is better than you.

And I think about that a lot. And I want to thank you for that quote. There's many, but that's one that, you know, helped me know that you were kindred spirit, man. Love that. And that one is about ego and confidence, right? Like ego is, I got to tell everybody how good I am. Confidence is knowing how good you are and not needing that. And I think, I think you've, you've been a shining light for that over the years is because I mean, there's plenty of, there's plenty of stuff that I think you can be egotistical about, man. And I'm going to dive right into it, man. A $2.3 billion valuation exit to Vista after all these years. Um, I want to, I want to hear what it's taken from you to, to, to get to that point and stay the leader of an organization from day one through that, because first of all, that's bananas, right?

So first of all, first and foremost, holy shit about the 2.3 congratulations. That validates everything that you're doing right now. And I think a lot more. Um, but it is extremely unique to me to see, I've always said stages of a business, right? You always, you always kind of fit. Like once you figure out where you fit, it's a liberating thing. I'm not a corporate guy, for instance, you know, I thought I was early in my career and then I got into startups. I'm like, I love this. And then when my first company got bought by Staples, I was like, Oh no, I can do this. But then when I come back into this state, like that organ, like the corporate structure, I fell apart. Cause I, you know, I don't have a filter.

I don't like playing politics. So they fired me. Right. And I figured out where I fit. And I say that for a lot of people, like, you know, some people are zero to 5 million, others are five to 25 million. Others are 25, but you've stayed through it all the way through to this acquisition. And now you're on your way to an IPO. How did, I'm just going to start with a really general basic question here. How the hell have you been able to do that? Um, you know, tough question to answer. I know lots of things and people, I will tell a story. I remember a moment. It was many, many years ago. And a friend of mine, a mentor had sold his company and had been right around the $10 million mark. And I remember reaching out and he told me, he said, I'm a one to 10 guy.

And he used that phrase. And I remember thinking through my head, I go, I wonder if I'm a one to 10 guy. And that's what I said to myself. I go, I wonder if I'm a one to 10 guy. And, and, you know, over time, what I thought was why pigeonhole myself into being that thing. And, you know, if I can be a one to 10 guy, why couldn't I be a 10 to a hundred? Why couldn't I be a hundred to 500? Why can't I be a 500 to a billion? And I just said, I'm just going to keep going. And, you know, if it ever gets terrible, then I'll back away. You know, I think that's the first piece is it was just like, okay, well, can I, you know, there's this book, uh, what got you here won't get you there. And it's like 20 things like phrases to think about that, you know, might've helped you to reach the point where you are today, but may not help you get to the next stage.

And one of them was this thing called an excessive need to be me. And it was negative. It was basically saying there's a lot of people out there and they have this excessive need to be them. And I recall once in 2000, let's call it 12. And I told one of the gentlemen I was working with, uh, John Birdsong, you know, John Birdsong, early sales loft employee, great friend of mine. And at one point in time, I said, John, you know, I'm just aggressive and direct and I'm sorry if I've ruffled some feathers, but that's just me. And he goes, well, you might have to change that if you want to get to where you want to go. And I remember thinking, Oh man, you know, like, and, uh, and it was that kind of great feedback from John that I took to heart and it, you know, hit me like a dagger when it, when he gave it to me, but you know, we put it to work.

And there's this saying that I've had running through my head continuously. And, you know, I think about it weekly and I used to write it down on things. And it just said that, you know, my job is to learn faster than the rate of my own experience. And so it's, it's become a mantra for me. How do I learn? You know, of course I'm going to make mistakes and learn from those, but it's better to learn from people who have done things and been there. And so I think that's a part of it. And then the last thing, you know, you know, tactically, I guess you could say, um, one, we've just surrounded ourselves by amazing people at sales loft, whether it's the investors, my co-founder, Rob Foreman, our executive team, uh, the staff, the SLG frontline, everything, you know what I mean?

We just really want to be around people that we love being around that are lifelong learners and that are out to make a difference. And that's been really helpful. Um, I, you know, shout out to my family. My, my dad is a servant leader and he's always shown me what the role of a leader is to serve. And I learned that from him firsthand. It took me a long time to internalize it, you know? Uh, but I think that's a big piece of it. But, you know, and then as a business, we, um, we put organizational health at the center of everything we do. And we think it's the biggest sustainable differentiating advantage of our business because it creates all the other sustainable differentiating advantages.

And so we've got a real strong rhythm around this business. We've got, you know, folks who are aligned, they're excited, they're learning more, they're doing more, they're becoming more, they're taking their talents and skills and using them to the fullest to serve others. They're finding fulfillment. And we're not worried about things like the great resignation as much as some other companies have to. And our customers get to get continuity of the, uh, of the person they're interacting with throughout their engagement. You know, it's really cool stuff like that. So I think it's just a combination of all these things and, and then luck, you know, we just happened to, it just happened to be that I love sales.

I love technology. And I entered my entrepreneurial stage at a time where salespeople had been underserved by technology for decades. And then we hit a couple of things, right. And it just kind of grew from there. So timing is everything, of course, and, you know, luck, but I guess it's a combination of those things. It is. And, and, you know, there's not one secret sauce here. I want to go back to some things you said though, that, cause I'm to a certain degree struggling with it. Um, you know, you, you, you might not be able to be all of you if you want to get to that next level. Right. And so, you know, like, you know, I'm authentic to a fault in a lot of ways, right. I say stuff that just comes out of the, like, I got no filter at all.

And that's been limiting in some ways, um, as far as, you know, opportunities or whatever, maybe I'm not the most polished dude out there, but I've always struggled with how do you keep that core level of authenticity and you being you while evolving and adapting in an environment that you need to fit in without losing your soul. And I think the, like, and I say that because I like, you're one person who I look to, who has stayed consistent with core values, had stayed consistent with who you are, but it's real easy to kind of forget where you're coming from. You know what I mean? Because now, you know, I went from startup to scrapping to, you know, people might, you know, might, might, might click, if you will, might not have been that high level baller.

Now I'm talking to all these huge conversations and like with other types of people, how do you stay true to who you are while evolving to the scenario? Yeah, it's interesting. I, you know, I thought about a story. I was in college and I was at Georgia Tech in downtown Atlanta and I was trying to get somewhere that I didn't know. This is before Google maps, you know, and I'm on my, in my car and I'm trying to drive somewhere and I call my dad and I ask him, where is this place? And he's like giving me pretty good instructions. And he lived in downtown, he went to Georgia Tech, he worked at SunTrust. He's giving me pretty good directions. So I'm just following him and I'm like starting to trust his directions.

And I ended up like taking a turn down a one way. And I remember I yelled at him on the phone. I'm like, dad, you turned me down in one way. And he's like, how on earth would I possibly know I'm on the phone with you, you know, and I felt dumb or whatever. But I remember I had this attitude. I remember I told myself that I was bad at directions. And I gave myself that label. And you better believe as long as I gave myself that label, I was bad at directions. And so I came to some conclusion, it was probably like six, seven, eight years ago where I said, I'm never giving myself another label unless it's positive. I'll give myself a label that says caring or kind, right? Or smart or hardworking, right?

Or great friend, great husband, great dad. I'll label myself those things all the time. But if I exhibit a habit that is not positive, like, let's say that I'm late, two to three times in a row, I'm not going to then label myself as a guy who's just late, right? Because then it's going to perpetuate. And so that was a mental, I don't know, it's philosophical. But that was one thing that I kind of went through in my head. But I know that doesn't completely answer the question. But it helps. It helps. You know, because it's the attitude, you know what I mean? Like, I think it speaks to the evolution, right? I mean, I think a lot of us have self-limiting beliefs about ourselves, about our scenarios.

And I'm a big believer in the, you know, law of attraction and positivity and kind of putting that out there to strive for as opposed to negative talk of, oh, I suck. And, you know, I got a bad memory or whatever that is, you know, and trust me, I get locked into it, unfortunately, probably more than I'd like to. But I think that journey of figuring out who you are, do you ever, in your opinion, do you ever kind of, it's a journey of figuring out who you are, but when do you feel like you settled into who you are? Well, I, you know, I kind of, I like to say that I matured early in relation to my peers, the fraternity brothers, if you will, because I got in trouble in college, and I got arrested multiple times.

And I had to go through a big experience of dealing with all that. And, you know, what I had realized is that I was, you know, everybody, I believe everyone has been given a unique story. They've got special talents and skills and capabilities. And I believe that they were put on this planet to use those capabilities to make an impact, to serve others, to make the world better, right? And here I was taking all of my talents and just straight squandering them, right? And so I had this moment, November 29th, 2002, I'll never forget it. And it really led to me having this attitude like, wow, I've been wasting my talents. And I don't want to do that ever again. And so I made a commitment that I'd take those skills and capabilities, my unique story that was unique to me, and I'd use it in a way that would serve people and make the world a better place.

And, you know, of course I screwed up and didn't always stay true to it, but it was the overarching principle of my life since then. That's almost 20 years ago. So I've been kind of living in that moment and that attitude. And, and, and part of that journey to get there was sharing all the stuff I'd been through and, you know, back to childhood, right? I was born with a rare blood disease. I wasn't expected to live past infancy. I had to deal with parents and doctors telling me I was going to die. And, and so it was just sharing those things openly and transparently. And I think I've gotten more and more comfortable over time, just letting it loose and, and, you know, and being kind of, you know, everything that I am.

And, you know, it's not always easy and sometimes I screw up and, you know, but it's a journey. Yeah. And I think it just goes back to, you know, if you got those right core values and you're doing things for the right reasons, you can screw up and people will give you the benefit of the doubt, right? I mean, we're, we are in a little bit of the cancel culture world, whatever you want to call it. But, you know, I know I'm very conscious of noticing people who I know are good people. And when they screw up, how it's reacted to and how they're supported versus people who are trying to be good people, you know, pretending to be good people, but are really rotten at the core for whatever reason.

And when they screw up, it's like, it, it, like, you know what I mean? Like they, they aren't, they're, they're pretending to be somebody else. And then when they're uncovered for who they are, it's like, oh man. And that's where you fall, see them fall off. But the people that stay true to who they are and for all the right reasons can weather almost any storm. Yeah. Well, that could be a debate for another day is are people rotten at the core? Well, true. I, I, okay. I'll take that back. You're right. I don't think people are rotten at the core, but people who do things for various reasons that, that may or may not be with the best intentions. Let's put it that way. And repeated behaviors.

Yeah. Exactly. So where was, let's go back to kind of that confidence that you've had as far as the stages of growth that you've seen and, and you're like, Hey, am I a one to 10 guy? Why not go to the billion dollar mark? Where, what part of this journey for you was the biggest question mark for you to get to the next stage? Like where, was there a point where you're like, Whoa, like, I really don't know if I'm made, if I'm, if I'm ready for that next step here. And I might need to reassess here. Was there, was there one stage that was harder than the rest for you to come to grips with as far as your abilities? There were a couple, I think one that comes to mind is early in the journey, very early in the journey, a company that many of us know came calling and, and, you know, had an offer for acquisition.

And it basically was like an echo hire at that point in time, I think, you know, just looking back on where the business was, but it would have been good, you know, life-changing money. And I remember, I remember exactly where I was in the hallway of Atlanta tech village, uh, with Rob Foreman, we went in the staircase and I said a word to him. I said a phrase to him that I now know was totally false. And I learned it was false, you know, quickly after I said, man, we could just sell this thing and then build another one, just like it, you know, like maybe not the same space or whatever. And, and it was, it was wrong because what we ultimately created was so magical. And it was not about just us and our abilities to just create a company, you know?

And so I think it wasn't long until I realized that, no, what we have is special and we want to hold onto it. Um, so I think that was one moment. There was another moment where, you know, we, uh, we abandoned a product and I know, you know, this story with sales law prospector where it was tough, you know, we kind of had this thing that was growing super rapidly, throwing off tons of cash, but it wasn't a long-term business opportunity and, you know, it didn't line up with what we wanted to do. How did you know? I'm going to like, let's dive into that. Cause that's, that, that was, had to be one of the hardest decisions for any founder to make. I mean, you, for people that don't know, you know, sales off first started and this was when we first met, it was like, okay, it was really just a simple trigger thing.

It was like, when somebody moved jobs on LinkedIn, what's that job change alerts.com. Yeah. And I'm like, oh, I love this. Right. And then all of a sudden you shut it down and I'm like, whoa, whoa, Kyle. I remember reaching out and being like, Kyle, what the fuck, man? Like this thing's awesome. What'd you do? And you're like, ah, LinkedIn's going to change their algorithm next month. And so it's going to be irrelevant. I'm like, oh, okay. And then you turned into this prospector thing. And I was like, oh, this is baller. Right. Um, and then you shut it down again and it was spinning off cash. And I'm sitting there going, dude, what? Like you got a profitable business right now that's spinning off cash that.

So how did you, what process did you go through to make that brutal decision to shut down and basically start from scratch with something complete? I mean, not completely new, but you know, some of the core tenants were there, but what, what evaluation criteria did you look at from a future standpoint to say, this isn't, cause I think there's a lot of founders out there that are holding onto a dream that, ah, like I created something and I, I know it's not great, but it's got, it's paying the bills right now and it's everything. So I got these golden handcuffs. So how did you make that, that decision? Well, I think we had a lot of things in our favor. One, we had started the business off with a clear mission that we were operating within.

And I'd kind of failed even before jobchangealerts.com to the point where I said, I'm going to run this business mission first, you know, values and mission. And so the mission was, you know, at the time it was a world of sales with sincerity. You know, we've really since evolved the language to really creating a world where sellers are loved by the buyers they serve. Uh, but that was at the core of the business from the very beginning. And, um, and so that came into violation with this product where sellers were using it to spam blast their customers. Yeah. They were downloading these large lists. They were throwing them in the marketing automation grinder, spinning the wheel and out would come the thing that you and I hated the most at our core.

And that's how we bonded from day one was we hate sales spam. We hate sellers who take shortcuts. We hate selfish, self-serving, you know, like those types of sellers. We don't like that. And we stand against that. And here I was creating a product that was helping make that happen. So that was a slap in the face that we realized. So that was one piece of it. Um, you know, another piece of it is that I was inside the Pardot offices when they were acquired for a hundred million dollars. Yeah. And I saw that journey up close and personal. And I knew I wanted to create a bigger version of that story. So it was a $10 million business. So I, and that was a hundred million dollars. So I wanted to order a magnitude bigger.

I wanted to create a multi-billion dollar. I said a billion dollars at the time. That was the goal is a hundred million in revenue and a billion dollars. And so when I realized that this product would never get to that stage, um, you know, that was another deterrent. And then I got to say that, you know, we generated a lot of cash off that product. And so we had capital to keep going and to do the new version. And then we had already started to build sales off of what it is today. So we had built the, the vision for cadence. Uh, we had interviewed all the sellers and learned what they were doing and what was working and what wasn't. We built the first versions of, of sales loft now, you know, then just called cadence and, and it was taking off as growing double digits monthly.

It was, you know, generating a lot of cash. We had control over it. Um, owned by the way, there's large company in the world who didn't like prospector. Right. And they made it known that they didn't like it. I don't know if they could have stopped it or not. It turns out some other people have been able to, you know, win some court cases and get past some of that, but you know, we didn't want to play that game. And so it, it actually was an easier decision than it, you know, seems like on the outside. And, um, you know, we have, uh, uh, uh, candlelight candlelit vigil at the office that was for the prospector and we lit it and we, uh, chanted and, uh, we said goodbye. Nice. I mean, that, that takes, I mean, cause I think almost there's so many people that would die to have a, just a $7 million company, you know, what I mean?

They like most startups don't get like 90, what 95% of startups fail after the first five years or something like that, you know, like less than 1% of them get to where they are. And so to me, that was, uh, an extremely, but I, but now that you say the mission driven piece, now I can see how much easier that decision was. Cause if you morph, if you, if you start with mission driven first values first, right. People over everything in a lot of ways. And then you realize you're getting off track, you know, you can start to, you can start to marry it up and say, Hey, this is still fit. Right. Yeah. Yeah. That's right. And is that, has, have you evolved? You said you've changed the language, um, over the years with your mission, um, as far as authenticity and, you know, those types of things.

Um, how is it, how has it evolved? Have you added to your mission? Have you, have you adjusted it along the way? Cause cause I think a lot of people have a vision. They, they, they put it up on the wall. They don't live it. And then, you know, they do a different activities, but you've seemed to have held pretty true to a vision all the way through, but I'm curious, has it, how has it evolved? It's just, it's just lived deeper in my heart. And I've been able to, uh, transfer it to other people through communications. And I've been able to find other people who have that in their heart and bring them in and connect with them. Uh, there's been a few times where I brought together a group of people, whether it's a leadership offsite or mentors board.

I mean, not that many times. I talk like two to three in the whole 11 year history of the journey where I just say, here's what, here's how I say the vision today. Here's why I don't like the way I say it today. What I really wish is that it said, meant this and sounded like this and, you know, felt like this when you heard it. So I've been thinking about saying it this way or saying it this way. And then they'll go, what about saying it this way? Or what about, and we just, nah, that doesn't work and just kind of bounce it off and forth. And I got to give credit to Rob Foreman and, um, uh, uh, a couple other folks on the ELT that we were at offsite, you know, a few years ago, probably five years ago.

And we said, you know, they came back after kind of hearing me talk about it. And they said, you want your sellers to love their buyers, not like loving your heart, but loving your actions. You know, like you want them to deliver sales love is, you know, we kind of talk about this term and, you know, why do you want them to do that? And I go, well, you know, I want them to do that so that they add the most value to their buyers. Right. So they can serve them and solve their problems. And, and he's like, well, you know, if they do that right, then buyers will love them for the experience that they received. And, and someone just said, uh, like Sean Murray, I think it was, you know, Sean, uh, fellow past fan.

I know you guys, that was the one thing that I didn't like about him, but, um, yeah, I think he said a world where sellers are loved by the buyers they serve. And I was like, that's beautiful. And so we, you know, I started saying it that way. Uh, so it's kind of tweaked a little bit, but it's always like, it lives here. And then it just like kind of gets tweaked as it comes out. Yeah. I think that's similar. You know, I went to the Gary V, you know, uh, 40 session and we did the Y, you know, and I kept pointing around and it really just came down to sales done. Right. Which is the simplicity factor. Like, you know, just do it right. And my definition of right might be different than yours, but it comes from authenticity.

It comes from, you know, and, and you and I say this, have the same philosophy here. It's like, I don't really sell you anything. I help you achieve your goals or solve your problems. That's it. And if, and I can't do those things, then please don't buy from me. That's the last thing I want you to do is spend money on something that you don't need right now. That's going to help achieve one of those two things. So I love sales done right, because it encapsulates, you know, how you treat the people that, I mean, it's, it's everything. It's how you treat the people that you're interacting with, but also are you doing the sales steps the right way, you know? And it's like, I mean, so it's art and it's science, it's form and it's function.

It's, you know, soft and it's hard. It's, you know, it's all those things. And I love that. So that's really cool. Yeah. It's been, but I think it's, I think it just like you, it's been more of a tweak and a clarification than an adjustment to, because I wasn't on the right track. And I think that's art doesn't change. It's just the way you describe it does. Yeah, absolutely. What's up everybody. I know you're enjoying this conversation. John does a great job with genuine curiosity on these episodes and our guests consistently bring the heat. We want to take a moment here and let you know that you've got an opportunity, an opportunity to become better than you were yesterday. And you can do so by gaining access to all of JB sales content.

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Let's get back to the show with JB and our guests for this week. I mean, look, the next stage for you is IPO, which I got to imagine is another cool journey stage here. It's something different for you to figure out. But as you sit right here- It's like upgrading from the minor leagues to the majors. Yeah. Well, shit, man. Majors. If you're in the majors now, then fucking I'm in junior high. I'm in grade school. But as of today, and I'm going to take the ones I know you'll say first out of the equation, as far as your family, your daughters and your son and your wife, what would you say you're most proud of at this moment right now? You know, I went straight to home, but I took that off the table.

Take those away. Sorry. Family's not like, because you and I, like, there's no, there's not even a close second when it comes to the pride I have for my family, my wife, my daughter, and that quote unquote accomplishment so far. I remember walking back into the office in 2015 after we had raised our first institutional round of capital from Emergence Capital. Yep. And the way we were structured, we were originally structured as an LLC and, you know, I didn't know what the business was going to be. And, you know, we didn't, we had a staff, but we didn't, they weren't all shareholders of the company. And part of the deal with the Series A was I'm going back and giving equity to every member of Sales Loft.

And I remember walking in that room and offering that up, you know, telling everyone you're now shareholders in this business. And to this day, for some reason, that kind of hits me as one of those moments to just, you know, really, really, really proud of it. Another moment is, you know, I came into the office and for some reason, maybe we won't go into too much detail. All of the management team's profiles on LinkedIn were gone. Shut the fuck up. Yeah. And it was my fault. And, and so I had to work really hard to get them back. And I remember being like, you know, here, I remember being so sad because here I am working really hard to create an environment where others can come to learn more, do more, become more, take their talents and skills, you know, all these things we talked about.

Yeah. And now I'm like killing their social, their, you know, social networking accounts, like their professional profiles gone off the internet because I'm, you know, upset somebody with our product or something. Right. And, and so working through that to get them back online. But I had a call, you know, we just did this deal with Vista and it's a really unique deal. You know, it's not selling the company and it's not going public. It's not, you know, being now part of a large strategic business and it's not now, you know, some new company just runs the business. It's a, you know, partial exit, like a mini exit, if you will. And, and one of the things we wanted to do as part of that deal is allow lofters to participate in the value they had created.

Whether you're a current lofter, whether you're advisor, whether you're a former lofter, we wanted them the opportunity to sell stock in this company that they worked really hard to create the value of. And I had a call with a friend of our mutual friend of ours, Tammy McQueen, uh, when the wall street journal article hit and she was our head of marketing for two and a half, three years. Uh, unbelievable, just amazing person. And, you know, I loved having her on the team and love watching her since then she's done amazing things. And she calls to congratulate me after the wall street journal article comes out. She doesn't say anything about her stock or anything like that. And I said, Tammy, um, you know, you're a shareholder in the company and I'm looking on the spreadsheet with her name.

And, uh, and she goes, oh yeah, yeah, yeah. He, she goes, um, thanks for, um, convincing me to buy those options. Right. Cause I guess I told her when she left, like exercise, exercise your options. And, um, and she got, I go, do you know how much those are worth? And I'm not going to get into that on this, you know, no, but she goes, Kyle, when we were working together, you told me if we did really well, I might get a Honda, a Toyota Camry or something like that with the money. And I was like, yeah, you're going to be able to get more than that. And so that was, and then of course, when I told her the actual number, she just goes berserk and she's yelling and screaming and crying. And, you know, it's hard not to feel great on the other end of that phone call.

And there's just so many awesome examples of that. Well, I mean, you made that call to me, man. I mean, it was funny because I, I remember when you asked me, you know, early, early days to be on the board of advisors and your board of advisors and just kind of be, you know, and look, I was tied to you guys anyways, because I believed in your mission and what you were doing. And I was like, sure. Yeah, no problem, man. Like happy, you know, quite honestly, I'm so, I was so ignorant of stocks and options and, you know, all that stuff back then. I was like, yeah, sure. Sounds, sounds good. And then I remember when you hit the billion mark, the billion valuation, I was like, wait a minute. I'm like, I think I, I think I have some shares.

And I looked back and I was like, holy shit. And then, and then I didn't know, obviously, but then when you hit the 2.4 and you, and you called me before you launched, I was, I was in an interesting spot. And that helped not just from the dollar figure standpoint, but from a lift standpoint. So I, I, I don't think I told you that, but the year was rough last year, like personally. And I was like, Ooh, you know, man, like the, the, the, the highs and lows of last year were, were, were more extreme than I've ever, I've ever experienced. And, and all the shit that I went through with dad passing away and all this other stuff. And then at the end of the year to have that, get that phone call from you, it was a little bit of like the universe coming back and saying, all right, like, you know, here, here you go.

Like, it's not, it's not all bad. You know what I mean? Like, there's, there's people out there that care. There's, there's things that are happening on a macro level that, that will keep you going. And so it meant a lot to me that call more than just the dollar figure, which obviously was, was fantastic. But, but I, I genuinely appreciated that phone call from you, man. I did. Well, I'll tell you, man, you earned every penny of it. Even if you hadn't been such a great friend to me and sales loft, the stuff you do in our market and in the sales community, that alone earns you and you deserve, you know, those types of rewards. So, uh, honor and pleasure and, uh, super exciting. Yeah. Thanks, man.

And, and, and look, um, what's next for you? Like IPO. Cool. But for you, what, what, what are you excited about now? Like now that, now that we've hit this milestone of exit where you now can pretty much do whatever you want to do for the rest of your life. Right. Um, and you, but you're still part of this, this engine that's moving here and you got a lot of people doing what, what, you know, you can offload a lot of stuff. Right. You got a lot of structure in place, a lot of great people who share your values. So you have the opportunity now to grow personally a little bit, I'm guessing what, what, what excites you? Okay. Cause I want to talk about that. And then I want to talk about the industry itself for a second, but I want to see what you're fired up for in the next, you know, moving forward.

Yeah, I'm not done. Of course, you know, we're not done with our mission. We're not done with what we set out to do at sales loft. I have, uh, many customers, lofters, soon to be customers, yet to be customers, you know, friends in this community that, you know, I want to deliver for. And, uh, and I'm learning so much more now than I feel like I've ever learned before. So I'm learning, I'm growing. I love my job. I love the people I'm doing it for. So, uh, you know, I'm ready to keep growing this thing. And, you know, what we've done at sales loft is, is been stay really, really, really close to salespeople, understand their pains and go out, innovate the market on creating solutions. That solve those problems.

And there's like no shortage of problems, right? And there's no shortage of runway on innovation. And we've got so much traction. Our market is huge. I mean, it's just, I almost wonder if like more companies are brought into the market every day than my whole category of software gets to been, you know, sell to. It's like the market's growing faster than we even can sell. And, uh, and so that's really exciting, but, you know, we've got a lot of things in place and, you know, the product is just unbelievable in terms of being the most comprehensive across modern sales. Um, just today was ranked by G2 as the fourth top software product and all of software, you know, thousands of software products for 2021.

And, uh, you know, it's really exciting stuff. So, you know, I'm in and, and, and, and, you know, attacking this mission, uh, building a great team and, you know, serving our customers. So as that relates to the market, like, so this market that we're both in and you're in from a tech standpoint, where is it going right now? Because my whole take on this is I really, really do feel like we're right in the middle of a pretty drastic transition in the sense that we're back in the manufacturing days in the sense that there's that widget stamper who was sitting on the assembly line stamping widgets going. And there's no way a machine can do widgets as good as I can. I'm the best widget maker ever.

And then holy shit, massive amounts of people got laid off and replaced through technology and stuff like that. And to your point earlier about, you know, sales done right and, and not spam engine and those types of things. Like there are so many people out there that are going through the motions and, and misusing, you know, some of these tools to, to do it the wrong way. So with that, with the buyer gaining more insights, with artificial intelligence coming in at every level, with, with the customer experience being everything now and how everything has been commoditized except for that experience, which you're that, that's why I think I have a lot more faith in you than almost anybody else because of that drive to delight the buyer.

So where five years out, 10 years out, are you, are you seeing this from a sales rep standpoint using the technologies here? Well, I think it comes back to the pros and cons of machines. Yeah. You know, machines can do some things way better than you and I can. They can hold more data than you or my brain, right? They can process that data. Well, they can access more data. They can bring it up faster. Whereas like, I mean, the human brain is bananas and, you know, my memory is terrible, but they're still trying to map this sucker because it's still the best computer out there. It's just, they can't find out information a lot faster, but I hear you. Yeah. Well, but it, but, but the human has things like intuition and creativity, right?

And nuance. And it's got things that computers just don't have. And there's not really a lot of signs that they're going to pick a lot of those things up in any sort of near term future. And so that's where I see things going in sales is let the computers do the heavy storage, the heavy lifting, the memory, you know, those things. And let humans do the, uh, the care, the extra creativity, right? The, the connection, the emotional side. And I think that's critically important in sales because, you know, I guess it was, um, it was Jeff Bezos. And he said, people always ask me what's going to change, but I tell him, I tell them, well, it's more important to know what's not going to change. And what's not going to change is customers want an incredible experience, right?

They want to be catered to, they want to be understood. They want to make their life easier, right? And a computer is going to get you to some point and then humans are going to take you the rest. And so it's basically just like the power of the computer keeps rising and rising and the humans just have to stay a step above them. And so for me, I believe the future of sales is from a technology perspective is a single place that sellers go. And right now today, like, how do you get things done? You got a to-do list, you got a calendar, you got a CRM, you got a task, you got email, right? That's basically the majority of all people, not just salespeople. So salespeople have all those things telling them what to do.

And that's a really inefficient way to operate. So the vision for the future of selling is that there is a universal queue of tasks and it's tailored and different to every single person based on what their use case is. Are they top of the funnel? Are they middle of the funnel? Are they post deal? You know, are they in manufacturing, selling manufacturing? Are they selling short sales cycles, long sales cycles, big deals, small deals, you know, whatever. And they log in and instead of having to go to email, calendar, task list, the CRM task, God forbid, the worst one ever, like the worst software in B2B. They come to this one universal queue. And this queue tees up the actions that they need to execute on.

And it's not just sending the same routine, templated email over and over again. It's tailored. And it brings up insights about the buyer at the point of communication for tweaking so that you can remember the last interactions or see information about the things that they've done. And those sellers are executing on those tasks. So it's a smart task list in that it's auto populated. It's a helpful task list and it lets you execute on the things. And it's powerful in that it knows that you did it and can improve over time, right? And so I believe that's the future. And think about it in terms of our micro market, right? You've got a frontline manager. They're going to go coach a rep on a call.

They're going to go log into their conversation intelligence and go look for that or maybe see it in their email. Then they're going to go submit their pipeline review or their forecast on another system. But the future of selling is they go to one place and it says, submit your pipeline review, one-on-one with this rep. This is a frontline manager's job, right? Coach this call, right? Jump on this call with this person. And they have one place that keeps them on track to all. And you could do it for sales enablement. You could do it for sales operations. You certainly do it top of the funnel, middle of the funnel, post-sales, pre-sales. And you can do it for execs. And so the world to me is just going to be smarter and smarter and smarter in terms of populating the things that you need to do, allowing you to have creativity to execute on them.

And they get smarter about recommending the next new steps for you. And so that's what we're building with the Modern Revenue Workspace. Love it. So what are the skills that are necessary for that Modern Sales Reps, right? Because I think they've obviously changed over the years as far as relationship development, you know, because it was face-to-face. And then it was, you know, ability to get your message across in a succinct way and ask the right questions. And then it was customer-centric selling, being able to, you know, ask the right questions. What are the skills you think? Like if you're, like, say, you know, this is Brooklyn, right? How old is Brooklyn? Seven. Seven. So, and how old is, what, Clark?

How old is four? Four. All right. So Brooklyn's your oldest, right? Yeah. So say she's getting into school and she's got an affinity for sales, right? She's like, you know what, Daddy, I really like what you, you know, you're doing out there. I think I want to create my career. She's now coming out of high school and she's looking at college or looking at not college, you know, whatever. But it's like, and you want to give her some direction on, sweetheart, if you're going to be successful in five years when you really hit the sales market, these are the skills you need to absolutely have and learn before you can, before you can really hit a home run there. What are those? Yeah. Well, I think it's like, it's learning first.

Yep. Whatever you sell, you have to be just as good at that specific thing as the buyer you're interacting with. You know, I tell our sellers, I tell our sellers that when they meet a CRO, they don't have to know how to hire or, you know, talk to the board or, you know, win an enterprise deal, but they do need to know more about sales engagement than that person does. Okay. So that they can transfer knowledge, right? So you need to learn enough to where you're an expert at something and you grow into it and you get pieces of it along the way. Then you need to be able to teach that back. You got to be able to earn trust so you can open up those lines of interaction. And some trust is easier to build than others, depending upon what you're offering, right?

If you, if you want to buy, you know, something that only one person in the world makes, then that person doesn't need to earn your trust as much other than the fact that they represent that product, right? And that's happens. They need to earn trust and they need to be able to diagnose specific problems, especially in enterprise and complex sales. They need to be able to diagnose challenges and they'd be able to help guide the customer to the solution. And I think those are the big, you know, the big kind of things that sellers need to do. Yeah. I think the, I mean, I think the belief, it always starts in the belief to me is like, do you believe in what you're selling? Right. Because if you don't, I beg you, and I say this, you know, a lot, if you're listening to this podcast and you're selling something that you don't believe in, I beg you to go find something that you do, because that's, those are the people that give us a bad name, right?

They're out there just trying to get a commission check and just screw people over, whatever the Glen Gary, Glen Ross is the world, the boiler, the rooms of the world and all that shit, you know? So a, it comes to the belief, which is why I think the core values, I, this is the exercise of the core value exercise, I think is a really critical one for a lot of people to go through. And I think COVID hopefully reset this in a lot of ways, which is like, what's important to me, because once you really get comfortable with that, then you can start to look for opportunities that align with those core values. Right. And that's why, like I've always said about us and, and sales, oh, look, you know, and you've heard me say this a million times, like I'm never going to work for anybody ever again, because I'm a pain in the ass for the most part.

But if there was one company, it would be sales loft because of the culture, because of the values, because I know I could slide right in. And, and it, it would, it would be like, yep, well, cool. Let's move. Right. So I think that, that understanding of what, you know, and I say, people say, follow your passion. I don't know about that. You got to find it first and then you can follow it. Right. So, but those skills of, of the human interaction, the psychology, because you said something important the other, a little while ago that, you know, what doesn't change is, is human psychology of why people buy and how people buy all the techniques, the technology that'll all change, right? Techniques come and go every week.

It seems like, you know, there's a new one or something else is irrelevant anymore, but why and how people buy that doesn't change much. And so human psychology, on this, on this front, you know, I think one is there's an old, I think, I don't know if it's Jim Collins or someone. And he talks about how a guy goes into his therapist and says, you know, I don't, I no longer love my wife. What should I do? And the therapist says, love your wife. And he's like, I don't get it. You know, I just told you I didn't love my wife. And, you know, you're telling me to love my wife. He goes, yeah, love your wife. And it's just like, you know, you just, you just go out there with that attitude of like, you know, loving and serving.

And it just kind of makes things all better. I think that's one perspective. Mark Cuban wrote a blog post and I think it was like, you know, clickbait title, how to get rich. And in it, it was like, find something you love and do it over and over and over again. And then I always think, you know, when I started sales life, we had a lot of junior people coming into the organization. And I'd talk a lot about, you know, what you want to be long-term and what your plans are. And a lot of people would say, I don't know. And my response to them was, there's that old song. It's like, if you can't be with the one you love, love the one you're with. And I would say, that's cool, man. You know, you, you don't know yet.

And a lot of people don't know, and I wouldn't expect everybody to know, you know, but you're doing something right now. So love it deeply, right? And, and just go after it. And then you might find, Hey, I like this thing more. You know, I love this other thing. It's going to open your mind up to a bunch of other stuff. So that's always kind of been the attitude that I've had. I love that. And I think that's that, that balance right now. I'm a little concerned with the newer, you know, generation coming in of the, the patience, if you will, to, to, to work through something, work through that hard part to, to figure out whether you actually are do like it. Cause it, cause it's so easy to hit, like to get involved in something and be like, ah, that's too hard.

I'm out. I'm going over here, but the, just the tenacity and the ability to, to work through that. So where do you, in one of the last questions I'll ask, how do you make that determination? Say you're doing something right now and you're in the middle of it and you're like, I don't know if I really liked this and, and, and, but yeah, my dad's telling me to earn it and I got to, you know, pay my dues and all this other stuff, but I really don't like, eh, like where is that line for you of a decision criteria that you would say, you know what, it's time for me to cut bait here. Or no, I got to stick this one through because I know on the other side of this, I, even if I don't ultimately like it, I'm going to learn what it's like to figure this out.

And then I'll be able to apply that later. Like, is there anything that you can help like people out there in that scenario? Well, one, I can tell them that they have it harder than I bet you and I did because, you know, when I was grinding early in my career, there just weren't other options. It wasn't, I mean, I couldn't just go get a 150 K job anywhere I wanted. And, you know, I wasn't looking online on my Instagram and seeing people on private boats and, you know, I didn't have all that life, you know, it was like, you know, I just got to go grind out and make it happen. So I think that that's kind of one thing that's probably changed significantly. You know, the other end of this thing is like, I always do the like grandfather test.

Okay. So I'm 65, 75 and I'm sitting on a rocking chair somewhere and I'm thinking, am I happy that I made those decisions? Right. And I'm trying to think about like putting myself in that person's shoes is why we had a third kid, you know, like I didn't want a third kid. My wife wanted a third kid. I didn't want a third kid. We kind of battled over it for about two years. And then I just imagine I was like sitting on the rocking chair with like some, you know, Arnold Palmer in my hand and, you know, seeing the grandkids running around there. And I'm like, I want more of those out there. Okay. We got to start now. You know, we got to, we got to put another one out there. So that was kind of the attitude.

I don't know. I mean, I think that's maybe one perspective, but it's a tough one because I haven't lived what they're living. Right. And, but I do think, but you said something important there with the grandfather thing, because I look at it as vision, right? Like, you know, what, what is, what does the future look like for you? And it doesn't have to be, you know, perfect. Right. But what does it look like for you in our, in our, is what you're doing right now going to help you get there? You know, I always kind of joke about the five, you know, where you want to be in five years. Like that's like, that's a, I don't think that's a great interview question, right? You know, I'll be a manager that no, but it's a great life question.

You know what I mean? Like five years out, what does life look like for you? What does lifestyle look like for you? Forget about the job and the, right. But what kind of, do you want to be married? Do you want to have a kid? Do you want to have a house? Like, what does that look like? And then let's back into what kind of money do you need to be able to have that? And what kind of job will allow for that money? And then based on what are you doing now to, to help you get there? Because I tell people like SDRs, let's bring it down to that level. You know, I get SDRs that come into me all the time. They say, Hey John, I'm kind of, I'm not really happy. I'm thinking about bouncing. Like, what do you think?

And I'm like, well, what's your plan? Where are you, where are you going to go? And they're like, well, I don't know. I go, look, without some type of guidance, without some type of plan here, like you're just going to go around, look, I'll eat a shit sandwich. Okay. And I'll be the janitor. If it's going to help me get to that next level, that's going to get to that next level. That's going to help me get. But if I don't have that vision for myself, I'm just going to go around looking for better tasting shit sandwiches. And you know what I mean? And, and, and, and really probably not like any of them. So I think that grandfather thing is, is a picture of the vision of, is this helping me get there?

And if it is cool, I'll, I'll stick with it. If it's not, I might go find something else. That's cool. I literally, I remember early in my career, someone, I was talking to some really accomplished person and they said, so I ate a mile of shit there. And then I got to the end and it was great. You know? And I remember thinking, I was like, okay, you got to eat a mile of shit to get to where you want to go. But I like what you're saying is like, you got to know where you want to go. The other thing I do is a little mental trick is whenever I get into something hard, I, uh, I had to, I don't know why this happened, but I started to have this like literal visualization that I'm in the foxhole in like Vietnam.

And I'm like, am I going to just cower in the corner or am I going to fight? And I'm like, well, I, if I was born in that era and put in that war, I'm going to go and I'm going to, you know, I'm going to do what I can. And I go, if I could handle that, then I can handle whatever this is. You know? And if my grandfather could handle that, then I can, I sure can handle, you know, doing whatever OKR, you know, I got accomplished. Man, it's all about perspective. I mean, I don't watch the news anymore because it's just too depressing. But for a while there, I watched it and there was, there's only one reason. I mean, I watched it obviously stay up to date on what's happening and whatever. But the main reason I watched it was to remind myself that literally, no matter how bad my day goes, I could legitimately have the worst day of my life.

OK. And I look up on that TV screen and I say, well, shit, it ain't that bad. You know what I mean? Like, I'm not sitting there worrying about drones over my head, dropping bombs. I'm not worried about where my next meal comes from. So I think it all is gratitude and perspective that have helped me stay somewhat grounded. I think the gratitude thing for me these days has really been a lifesaver. And I say that kind of, but not really. Like, in the sense that, like, I've had to, to a certain degree, force positivity because of some of the things that I've, you know, been experiencing. And this little stupid gratitude journal that I keep every day of the small things that happen throughout the day, it's one of those things where, you know, I look at it at the end of the day and no matter how bad I think the day went, I lost a deal, this happened, oh my God, whatever.

I look through it like there's like five, six, seven, eight things that happened positive that all I got to do is change my lens a little bit. And that's been a real just kind of comfort blanket, if you will, through these times here, which makes a difference. It's almost become like cliche to say it, but you know, the old phrase, it's like, if you found some, if you're, if you found yourself or someone else depressed, like the best way out of it is to do something for someone else, you know? And it's just like, pop, you're done. Well, I mean, you hear it every time and we're coming up on that point, but I say it all the time. I don't know where I started or why I started, but I say this every time, like at the end of the podcast, no matter how bad your day goes, go out there and make somebody smile.

Because if you made somebody smile today, literally no matter how bad your day went, you actually had a good day. The world needs a lot more of that right now. So on that note, brother, look, it's always fantastic to catch up. And I feel very fortunate to call you a friend, you know, business stuff aside. Thank you for, for being one of those consistent, give a shit people that continues to show up. And yeah. So, I mean, I don't know if there's anything else you want to leave with the, with the audience here about, you know, any guiding, you know, any last words of wisdom or any of that stuff. But thank you. Yeah. Honor and a privilege, man. And thanks everyone for tuning in and appreciate spending time with everyone.

Absolutely. All right, everybody. I already said it, but like I said, go out there and make somebody smile. Uh, world needs a lot more of that right now. Thank you all very much. Thank you so much for your time today and listening to the podcast. I hope you enjoyed the conversation as much as I did with your support and our incredible guests. We're one of the top sales podcasts in the industry with over a million downloads. And I can't thank you enough to keep the momentum going. If you could go to your favorite podcast platform and leave us a five-star review, I would greatly appreciate it in return. I will answer any question that you have on Instagram. Hit me up there at John M as in Michael Barrows with a video question or a DM, and I will get right back to you.

I promise. And last but not least, if you're looking for training, I'm adjusting my training approach this year, and I'm actually going to be delivering training to the masses. I'll be delivering live training the first and second week of every single month with our two marquee courses, filling the funnel and driving a close to anybody who wants to join. And it includes membership in our on-demand platform with weekly AMAs. So you can go to jbarrows.com slash open to check out the details. Thanks again and have a great day.

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