174: Ryan Leavitt On The Entrepreneurship Path

What's poppin' y'all, it's your man, James Say What Sales Buckley, and you're about to join us for another episode of Make It Happen Mondays with your host, John Barrows. This edition is brought to you as always by our partners, Sales Loft, Gong, Vanilla Soft, Vidyard, Proposify, Zoom Info, Loom Cube, and Rise. Today, our guest is Ryan Levitt, co-founder of Pillar Booth. Pillar creates high-performance call booths that support a long-standing truth in sales. Our environment matters. We're so amped about this that we've collaborated with Ryan and the team at Pillar to offer, well, you guessed it, a JB Sales Make It Happen custom call booth. There's even some talk about us giving one of these away to a lucky fan, so stay tuned.

Ryan is going to be talking with John about taking risks, building a culture of passion, and much, much more. Be sure and check out jbarrows.com slash pillar to get some special offers through our affiliation with Ryan and Pillar. Talk to you soon. Let's pass it over to John and Ryan in the studio to make it happen. Good afternoon, everybody. This is John Barrows. Make it happen Mondays. Hopefully you had a good weekend. I had a surprisingly good weekend because my Patriots actually pulled one out at the last minute against the Jets, and if we lost to the Jets, I don't think I'd be able to watch them anymore. But anyways, it's a good week. It's a great week this week. Things are looking up, and I am here with a good friend of mine as well, which I'm excited to have a conversation.

Ryan Levitt, co-founder of Pillar Booth. How are you doing, my friend? It's good to be back, John. And I also had a great weekend, not because of the Bears, because they keep losing, but because of the 75-degree weather in November in Chicago. I will take that. Dude, I'm sitting there right with you. It's 75 degrees here in Boston in November. Now, don't get me wrong. My wife's an environmentalist, scientist, so we're like, this is not a good thing. But shit, man, 75 in November, I'm taking it. We'll take it this year especially. Yeah, no shit. Exactly. I mean, and it snowed. I don't know. Did it snow in Chicago for you like a couple weeks ago? Not yet. Dude, we got hammered with like seven inches of snow, not even a week ago, and it's 75 degrees this weekend.

Wow. Anyways. So, Ryan, what we're going to talk about here is entrepreneurship in general, right? So, a lot of people that I talk to are entrepreneurs, but then we pick the topic of what they're specialized in. And I think with your experience here, we're going to dive deeper into that entrepreneurship. So, why don't you give that background, right, of where you're coming from and how you got to what you're doing now with Pillar? Yeah, the quick background was basically, like, I started my career in big company, you know, in finance and in consulting, like the opposite of entrepreneurship. But actually, those experiences were amazing to help me figure out, like, this is the direction I always wanted to go.

I always wanted to be, I always had this entrepreneurial drive, and you kind of learn how to work and you learn about organization. So, anyway, started a few companies. Most recent one was a company called LearnCore, which was in the sales and development space. And that's how we got to know each other very well. We were very early in the sales and development world, focused on training and coaching. And personally, I love sales. I love marketing. I love interacting with customers and understanding what their pain points and what drives them to make decisions. And that's one of the things that was so great about LearnCore is that we worked with hundreds of sales leaders at mid-size and large enterprises across the world.

And we got to really learn not only what worked in sales and what didn't work, we got to know them and help them. It was a great experience being early on in the sales and development world as it started to grow. And then we sold that company a couple years ago, and I took some time to figure out what I really wanted to be doing. And it all goes back to a couple of things. It goes back to this idea of like, I love building companies and building teams and solving problems. But then I also love sales. And I love that side of it. And I personally could get into as we go, this idea around selling is the most important. I think one of the most important tools for founders that many are scared of.

We'll get there in a second. But Pillar Boot is a phone booth, right? It's an actual box. It's a physical box. It went from making sales enablement software to making a box for people that have privacy. And that sounds crazy. But there's a couple of sides to this. One is that it kind of is sales enablement, right? I'm in this world of the environment, the physical side of sales enablement, which is cool. But the other thing is that I'm just working with so many sales leaders. I saw there was a kind of a big opportunity to take what SaaS companies do from a sales and marketing standpoint when it comes to strategy and execution and take back the traditional physical products in the B2B world. So that's why I'm here.

I think it'll work. But we're still pretty early in the journey. Yeah. No. And I think it's actually it's funny. Yes. But, you know, again, opportunity, right? This whole COVID thing is the enclosed space is actually now, you know, when we start moving back into offices and that type of stuff, it's going to I actually think you're positioned extremely well with something like that, because there's going to be a shift in how offices are even set up these days because of what's happened here. And this is not the last weird shit pandemic thing that's going to happen to businesses. So they've got to be kind of preparing for that moving forward. And I think what you're doing is actually fits right in line with it, as a matter of fact.

But look, let's go back to you'd said, because I think you and I have had a similar journey to the entrepreneurship world. I don't I never thought I had the I never had the itch. I just knew I didn't fit in corporate. Right. So I started and it's funny because my backstory, my both my parents were they were consultants. They might not have been entrepreneurs, but they were kind of in the sense that my mom, you know, quit her job at Wang Laboratories when I was a kid and started her own little consulting firm. So at our house, my living room was on one side and my mom's office was on the other. So she always worked from home. My dad was a consultant for the FAA. So again, he worked for the house for the most part.

So I was always kind of around it. I didn't know it. Right. But when I got into the corporate world, my first job was DeWalt, Black and Decker. Then it was Xerox. And I just remember just being like, ah, something doesn't feel right. Right. Because I didn't like the whole concept of you had to spend two years doing this and then two years doing that and then two years doing this and you get your merit raise here. And then like I just I was like, yeah, but I want that role. Like, how can I get there? And I'm better than everybody at this role. So why can't I go there faster? Right. And it never jived with me of no, no, no. That's the way it works here. So thankfully, a buddy of mine, Chris, as you know, started a startup and I had never thought of startups because I'm an East coaster.

You know what I mean? That's usually for the West Coast weirdos back in, you know, 30 years ago. And but I got into it and it just clicked. Right. And all of a sudden that itch that I didn't even know was there was scratched and I never looked back. And so you you started at big corporate firms. Right. Did you always know even going into that, that you you were using that as a as an avenue to get to where you wanted to go? Or did you learn it along the way? It's a good question. So I and it's funny, I tell the story a lot because I think it's relevant. So it was, you know, in the early 2000s, I was at the University of Michigan in the undergraduate business program. And it was probably one of the top two or three undergraduate business programs in the country.

I think I think it still is. Hopefully not the football team. We don't talk about that. I went to you. I went to you, Maryland. I'm excited. It's still good. And so we and I say that because like it's this great school and it's great university, but we were kind of like funneled into three paths in the business school. There was finance, there was marketing and there was consulting. There was no venture stuff. There was no entrepreneurship stuff. There's and like now today there is. You could go to the business school. All that stuff is there. But, you know, 15, 20 years ago, it didn't exist. And so I went into finance almost by default. I didn't want to go into marketing. I don't want to go into consulting.

So I went into finance. And I went into what I consider the most entrepreneurial part of the finance world. It was in private wealth management. And it was a golden sacks where there was each team was basically its own business. And that's why I went there. So like I actually got to learn about operating and running businesses in this little team. But the other thing that I learned, and I always had this inclination that I was going, that I was very entrepreneurial. But this was in like the three worst years ever, 2000, you know, six, seven, eight, nine. So that's when I graduated. I was lucky enough to graduate then and go into finance when people stopped getting bonuses and stopped getting paid, which was actually a blessing in disguise.

Because if I was making a ton of money, I probably would have stayed there, right? What I got to do is really understand like, hey, I wanted to do what my clients were doing. I wanted, they were all executives. They're all entrepreneurs. They were founders. That was so interesting when I got to talk to them. And so then I left there with the consulting so I could just learn more. I didn't want to be consulting and travel four days a week, but I wanted to learn and get involved in big companies. And I did some, I did some pretty cool stuff. And I was in something like big airline merger integrations. And I learned a ton and then I left to start my first company, which was a huge failure really quickly.

It was a company called Deal Umpire, which was in 2009, 2010. And like the whole daily deal space was blowing up like crazy. And we didn't think it was a good, I mean, one of my business partners didn't think it was right for small businesses. And he owned small businesses at the time too. It's like we really understood that side of it. So we built a company to be, sit in the middle, it was like a referee. And so there was deal sites on one side and there were small businesses on the other. And it started to work. We had 99, we never crossed a hundred. We had 99 deals. And then like literally a month later, the whole industry died. And it just all, it all collapsed. Like everything that I thought was going to happen over like five years happened in two months.

Oh, there's all this bad news about Groupon and all that stuff. And so that was my first experience. Like I did, I did basically everything wrong in that experience. I built a sales team and we shouldn't have. And if you look like you're going to ask questions. I was going to say, how old were you again? When, with that failure right there? Ah, 25, 26. Yeah. Cause, cause I think it's important for people to hear that that's when you should make your mistakes. Yeah. Right. I, I fundamentally, I mean, you know, now both of us, wife, kids, that type of stuff. Like once you have responsibilities and shit, your risk profile goes down drastically. Yeah. But in your twenties, you, you should try and fail at as many things as you possibly can.

So what do you say to those kids out there? Cause I think actually now, I mean, I started two companies in two of the worst economies ever, right? 2000 was when I graduated and that's when we started Thrive Networks. But it was a, it was a huge opportunity, right? Cause when everybody else is always me, I'm like, wait a minute, there's an opportunity here. Let's run. 2007 is when I effectively started Jay Barrows, but more can say partners that morphed into it. And again, 2007 was brutal. And now, I mean, this is different than anything any of us have ever dealt with. But I think there is a huge opportunity here if you look at it the right way. So what is it, your, your risk profile, if you will, help me understand how you look at opportunity.

Because my, the way I look at opportunity is I'm not a risk taker. Like a, like Chris, my buddy who got me into start, that kid's a risk taker. Like he will live on, live in his parents' basement, eat ramen noodles and, and bet the farm on it and fail 700 times and figure out a way. And eventually one of the, I'm not, I need to have a certain amount of things in place for me to, so I'm a calculated risk taker, but I'm also an opportunist. And I've been able to kind of, the skill is that I have is I can look at something and put only a few pieces together and say, that's a good idea. Let's go for it. Right. Without overanalyzing it. So how do you suggest that people look at that if they do have that itch, if they are in a company right now and they're like, you know what, there's an opportunity.

I don't know what it is, but I, and I don't know how to get there. How do you frame your mind around that risk assessment there? I'm similar to you. I'm not a, I am a risk taker, but I'm a calculator risk taker. I'm not someone, I also don't, I'm not the person that's going to go out and build a $20 billion company that's going to change the world. Like, I just, I don't have that, that vision and I don't think of that idea. Right. And, and I probably don't have the risk tolerance to go after that, where there's a 99% chance you fail and 1% chance that you crush it. Yeah. Elon Musk, right? Like that motherfucker. That's not me. I'm the person, I'm more like you. I'm like, all right, I see an opportunity and I know I have these pieces in place and they fit into my skillset and I can go after it.

So take pillar booth, for example, okay, pillar booth, I know nothing about manufacturing. Now I do, I did not two years ago, right? I knew nothing really about how to sell furniture. Now I do. But what I know is I understood the pain point. I had a great network of people who validated one, this is a pain point to, they could be very, very valuable distribution channel, one of the three largest furniture dealers in North America is a good, I became good friends with them through the business world over the last 10 or 12 years. And from day one, I've been talking to the owner of that company, the president of that company to really understand the pain point. How do we get into other furniture dealers?

How do we build our brand? How do we, how do we understand that side of it? Right. And then for me, when I look at it, I understand the pain point. I know it's a huge market and I'd love to sell. And when I look at this industry, the big opportunity to me is that there might be two dozen phone booths out there. There's one company that does an outstanding job in marketing. And there are 23 companies that do a very bad job in marketing. And most of them only sell through the channel. They don't sell direct to business. So we can go direct to business, we can sell through the channel and we can do a better job in sales and marketing. We might not do better at marketing than that company that's crushing it, but we can be the second best when it comes to marketing and we can be the best when it comes to sales.

And those two things I know we can do. So I look at it and I'm like, all right, big opportunity. This is going to be fun. I'm going to, I'm going to learn a lot of new stuff. I'm going to kind of like help to build a more, a bigger picture of the world in my mind, right? I'm going to go from software to this side, but I know a couple of things. Is that like with my two business partners, right? Who I've known for 25 years. And one of them is one of the smartest people I know. And the other one is also very intelligent, but he also happens to be a engineer, architect, furniture designer, my trade, right? So we've got the right people to start with. We have the right network. And then we have, I think, a pretty conservative strategy to go after it.

And because of that, I felt confident, right? But if, and likewise, when I invest in companies, right? And I, and I look at companies to invest in, I'm similar to you. And I look at them and I say, okay, I can address the situation pretty quickly. I can understand, is there a pain point? Are they solving it? What's their, how are they going to, how are they going to tackle it? But then the number one question to me there is, is the founder going to do the sales? If the founder will not do the sales early on, or they're scared to sell, they're just going to keep building product and they're never going to sell. And I've seen that happen so many times, like that to me, when I invest, is the number one thing.

And then you pull it back here, like you, you're going to sell, you're going to make the cold calls. I'm going to do the same thing. And so that helps to control that process. Yeah. I actually wrote a blog post a while ago called The Founder's Dilemma, right? And it's based on the engineering founder, the smart founder who, who comes up with a product. By the way, those people are way smarter than you and me. Way, way, way smarter. Okay. But, and you know, and you said it earlier, you know, well, you alluded to it, you know, the number one reason that most startups fail isn't because they're not smart people, isn't because there's not product fit. It's because they can't fucking sell it. And if you, and the founder's dilemma is that engineer, because I, you know, sales, I believe is the transfer of enthusiasm, right?

And what happens is a founder comes up with a product, service, salute, whatever it is, and they get all excited about it. So even the dorkiest engineer, when they sit in front of, usually in their first sales pitches, they're all friends, families, and fools, right? So there's, they're pitching to an audience that is receptive. They are passionate about what they're selling. And then they might get, you know, two or three people to buy into it. And they're like, holy shit, this is easy. Everybody loves this. Let's just go hire a bunch of sales reps and, and, and go. And then those sales reps, because they don't have the passion, they don't have that transfer of enthusiasm. They don't have a real understanding of the problem.

They go do their thing and they fail usually pretty hard. And then the founder gets pissed that sales sucks. And then they go to marketing and they say, okay, let's do, you know, SEO, because obviously we got to do inbound here because the sales reps blow at this. And then that only gets them to a certain level, right? So without that... We're basically saying what happened in my first company, except we didn't get to the point of doing SEO. Like we just, we couldn't figure out how to sell it. And we just ran out of cash in the market. Like it was like this whole, that's exactly what happened. Yeah, it's almost, and it leads to my other part of the, that you brought up, which is the team that you put together.

And I think this is so critical because yes, you need to sell, but you also, you know, Chris's first company thrive. Like when he started that company, he was the tech guy, right? The idea guy. But he, he didn't go into business with a couple of other tech guys. He had a finance guy and he had a CEO who was like a strategy guy. So that it was like this three headed monster that all worked really well together. And then with the management team, I was the VP of sales. And then we had a, a CTO, a director of professional services. And what happened was I would look at them and yes, I would challenge and push back, but ultimately I didn't know how to do their job. So I wouldn't suggest on how to do their job.

So everybody complimented each other. After that, after we sold the staples, I was always with salespeople and I was, and I was finding myself like always arguing because inherently, I don't know if you, if you agree with this, but inherently if you and I do the same job, okay, like if you're a sales and I'm a sales, we're competitive. So I, I look at it as I could, I could do your job and, and, and I'm kind of better, right? But if you're an operations person and a finance person, I do, I have no fucking idea how to do finance. Go ahead and do finance. Let me go do sales. How do you think of building your team? Cause I think that's a part of this is where people want to start moving off on their own.

They got to have that team in place or at least a partner, but not a partner that does exactly what they do. So how do you look at building out your teams for startups and entrepreneurs? So team building is, I think, really, really difficult. You get better at it, right? You get better as you go and you like anything else, you make the mistakes and you figure out who you need to find, who you need to hire. Like a general rule of thumb is like early on as we're first getting going, right? You need a bunch of journalists who work really hard and can figure stuff out. And then as we scale, it's hiring people that are better than me and my co-founders at each role. Like we're not, and then we get to the point where we're not specialists, right?

Where we might be great at one thing, but like we're, we can't do everything anymore. Which is actually one of the fun things about being back at like this really early stage. You know, go back eight years at LearnCore when me and Bashal and Ethan were, we were the only three people on the growth side of this company, right? The three founders were doing everything. So we were BDRs, we were AEs, we were sales engineers, we were customer success, we were everything. And then we got to build on a team of people who were way better, right? And they were, they were so much better than us in those roles and actually got to scale it and, and actually build a kind of a machine out of it. But because of those early days, we got to understand the customer, right?

We got to, we got to really build those relationships. Like that's how I got to know Doug so well. Like me and Bashal were out there with Doug every second from day one. We were able to build this great relationship and he became a huge, huge advocate and also helped us understand the market. Like those are the things that founders can do early on. And then you could keep pushing that mentality into start something that we actually, that I, that I see a lot with kind of like that growth stage company is that they get past, they lose that entrepreneurial edge, right? And so then they get to the point where they've got sales reps, they've got managers, they've got directors, they've got VPs of sales and nobody asks any questions.

And they actually miss, they miss some opportunities because people like are so focused on this like really regimented process that might be great at SAP or Oracle, right? But at a 200 person company, you need to still be entrepreneurial. You need to still like analyze the situations and figure out like, one, how do we close this deal? Two, what does this say? Is this a bigger opportunity set than we're actually even going after today? And like continuously try to think like that. And I think the best like growth minded founders will always see that. How do you build that culture though? Like, you know, it's funny when we were, you know, 50. So story on my, you know, Jack Welsh, right? So when I, when we were Thrive Networks, we were 10 people, everybody's all in, super passionate, right?

Challenging each other, everything. 20 people, all right, we're still good, right? 30, 40. And then we hit 50. And I think 50 is the mark. Because the 51st person that we hired, it was a job to them. It was a job, right? And I remember Jack Welsh came to Boston and he did one of his huge, you know, Q&A seminars. And there's like a thousand people in the seminar and you just stand up and you ask him a question. He answers, right? I guess paid like 300,000 to do it. It's ridiculous. But anyways, I remember standing up and I said, Jack, you talk a lot about passion. You talk about, you know, that type. You know, we started this company and we're at 50. That 51st person just doesn't have the passion.

So how do you instill your passion on them, right? And he corrected me in front of a thousand people. He said, you can't instill your passion. You got to hire it, right? That's why hiring is the hardest thing. But so with that, how do you foster in the early days? I think it's easy. But once you hit that 50, 100, how do you continue to foster that entrepreneurial spirit, the challenging, the looking at things outside the proverbial box? I think it's easy as a founder or leader of that size when you do 50, 100, 200 to just only stay at the, you know, at the high level view and only focus on high level strategy and managing the management team. And I think that as a leader, you actually need to stay deep in the business.

You can't get your hands out of it completely. You get your hands out a lot because that's way better for efficiency, right? But like if you lose touch, then you can't, you can't instill your passion, but you could show your passion. You could lead a passion. And if people see you doing it and see how you interact with customers, that will resonate through the team. And as soon as you stop doing that, that's when it becomes an organization of people who have jobs. And I think that's the biggest difference. Yeah. And I also think that there's like the vision, like do you buy into it, right? And most people don't live their vision or even articulate their vision. And I've always said that you can never get somebody to do something more than their job if they don't believe in a bigger picture thing, right?

So how transparent are you when you're growing companies with your organization as far as the finances, as far as if you're building this to sell, if you're building this for IPO? Like what's your suggestion on that as far as the transparency level that you should have with an organization and how far does it go? I think transparency is really important. I think we didn't do a great job at LearnCorp early on. I think we got better later on as the years went by. And part of that, a lot of that was just by listening to our employees, right? Listening to the team and saying like, okay, like getting feedback, hearing one-on-ones, hearing just like in all hands meetings. Those were questions people asked.

And also, we didn't always understand what transparency meant. When people say we want transparency, as a founder, you're like, oh, they want transparency in thin numbers. We'll give them more numbers. We'll talk about that stuff. That's not what they want, right? They want strategy. They want to know why. They want to be involved in decision-making. They want to be heard. That's what transparency is. And once we started to understand that, things got a lot better. That's a huge part of building a good culture. I think with Pillar, we're going to be building a much more transparent organization. I think part of that comes with just learning. Part of that comes with maturity. And also, I think times change, too.

Things are very different now than 10 years ago. And they'll be even much more different than 10 years. So I think we have to continuously evolve as well. Yeah, I mean, I think that and it's even the bad news, right? I mean, what frustrates me is when you're sitting in an organization, you've reached a certain level, and you know the founders having weird conversations behind closed doors with people you haven't seen before. And it's obvious that the company's on the blocks, right? To either get sold or to take another step. But the CEO just stands there. No, no, we're good. You know, just we care about everybody. Like, my whole philosophy is, like, if you're going to sell, tell everybody in the fucking company that you're going to sell.

And then give everybody a little piece of it so that they feel like when this thing goes, you know, they're a part of it. Because they'll help you get there. But if you hide it from them, you'll start to hear dissension. You'll start to, people will start to look for other jobs. It'll erode at what you're trying to ultimately do. So, you know, obviously there's certain things that you can't tell the organization. But, you know, I tell my team, 95% of almost everything, even how I'm feeling, like, fuck, you know, we're kind of screwed. Or, no, I think we got a chance here, right? That type of thing. When you're a 5 or 10 or 15 person team, I think having that level of full transparency is very important.

Because these are the people that are, like, the most important people on the team forever, right? They're building the core and the foundation of the business. And so, like, that level is really important. And also, if you have 10 people, 15 people, and your company is going to be acquired, like, then, you know, everybody actually will probably need to be involved in that process, too. So, you know, they want to understand why and understand, you know, what's in it for them. As the company grows, right, it does get a little bit more delicate of what you can share with. But I 100% agree with you, like, especially as a company smaller, 5, 10, 15, 20 people like that, you know, the smaller it is, the tighter it is.

And if you ever get to 50 or 75, 100, and assuming those 15 or 20 people are great and great culture fits and, you know, are aligned with the vision and where the company is going, you're going to want them there. And you're going to want them growing within the organization, which is another thing that we did not do early on. We did not do a good job with growth paths or education or training or giving people leadership opportunities. And that's really, really important to build a great team as the company scales. Yeah. And understanding what drives each one of those individuals, too, right, whether it is progression or family or money or whatever, and kind of, like, let them go, get that and help them get there.

I think one of the, you know, one of the most proud things that I, you know, with Thrive, it's not that we sold the company, it's that the people that I hired, like, I saw them become successful. You know what I mean? And I didn't, I don't take credit for their success, but I put them in a position to be successful and they took advantage of it. And now, you know, they're supporting their families, they got nice houses and all that other stuff. And regardless of what we sold for or who we sold to or what we did, seeing that, to me, is far more satisfying than any check that I might get, you know, out of the, to the outcome here. I mean, we still, like, I know it's only been a few years, but, like, like, Pat, you know, Pat, Pat's the CEO now of a company in Indie, also in sales tech, which is so cool.

Brian is now, he's the head of sales for a company called Screencastify, which they were called Acquire a couple years. So, like, you get this, this, like, family of people, to your point, and, like, they get to keep going and you get to watch them grow. And it's, it's, it's great. And that's why hiring is very fun. It can also be very challenging. Brutal. Well, I think hiring is the hardest part. I mean, I got, you know, Scott and Gregor from something new right now looking for somebody else to come on board and do training for us. And, you know, kissing a lot of frogs here because I'm, I will not compromise on values on these type of things. And, you know, it's, it's a brutal process because you, like, as a small business, you make one bad hire, it, it could bury you.

Right. Not only financially, but reputation wise and everything else. We, we used to, like, really come down on this idea of accountability, which sounds, it sounds harsh. Right. But it's like, it's not. And the way that we describe it is, I mean, think about a football team, right? Like, if the offensive line isn't, isn't, you know, pulling their weight, but it doesn't matter how good the quarterback is. The quarterback can't do anything. They're getting sacked. They're getting flushed out of the pocket. They're getting hit. They're getting knocked down. They're getting injured. Right. And a company is no different. Right. And so like, everybody is accountable to, for themselves, right. For their team and the company.

And when you start to drill that in, right. If somebody isn't pulling their weight, it actually impacts everybody else in the company. Everybody else in the company should get upset about that. Right. Because like, they are, they're working their ass off and they're, they're involved in, in, you know, strategic planning and growing the business and, and, and like really aligned and passionate. And if someone else isn't doing that or isn't treating customers the same way, or isn't like upholding the company's brand the same way, that impacts everybody else. And that should piss them off. Right. And I want that to, I want them to come to me and they're like, I love this company and this person isn't cutting it because of X, Y, and Z.

Like that's the stuff that I want to hear. That's how you know that everybody else is really bought it. And you've got this great team and if you have 90% great team and 10% don't uphold that, then great. Like you could continuously improve that and get there, but you need that core. Ryan's experience comes out big time in this conversation. There's a lot to be said for being willing to understand that you don't know everything. And there's always someone out there that can teach you something. Don't forget to send me your sales wins at james at jbarrows.com to be highlighted on next week's show. Today, we're given a big shout out to Bella Ho of Twilio in Sydney, Australia. After joining JB Sales On Demand at the beginning of October, 2020, Bella understand her role so much better.

By the end of the month, she was able to schedule 17 meetings and create 15 new opportunities. Her November is also starting off strong with 13 meetings already on the books on the 16th. She's loving her role more and more every day and seeing consistent success like that is a big reason why. Way to go, Bella. Keep selling better. Don't forget that you can join JB Sales yourself and start learning to sell better just like Bella. The courses and certifications at JB Sales On Demand are game changers for results and performance. Visit us today at ondemand.jbarrows.com and start living a sales life instead of surviving one. Let's get back to the show. You know what? So, team, let's talk about the external team because you brought up earlier about your network, right?

And how you were able to tap into that. I think networking in the sense of going out there, meeting people, grabbing coffee, going to, you know, that type of stuff. And, you know, I was such a hardcore networker when I first started in business. I went to every networking event I could go to. I went to every networking group, right? And what happened was when I was ready to start my business, I could, and I did so many favors back, you know, early days, like the whole give-get mentality here. I would give way more early. Even if I needed something, I would just, hey, how can I help out? How can I help out, right? And so, when I was starting a company, almost everything I needed was one call away.

Hey, I need a payroll. John, no problem. I'll take care. Hey, I need a website. No problem, John. I'll take care of you. So, it was like, I remember my business partner, when we split from Basho to Kensei Partners, I had us up and running in a week. We had a website. We had an LLC. We had all these things. And he was just like, what in the shit? He's like, how did you do it? I go, well, I just, I don't know. I got all these people. So, how do you look at networking? And then let's put that in context of today. Because my fear today is we are now in this COVID world where it, this, you know, those events aren't happening. Those groups aren't happening. So, how do you build your network? First of all, how important is your network to you?

And then how did you approach it? And then how would you approach it now in this environment? Especially if you're a young kid with no connections at this point. My network is everything to me. Like, that is, that's your personal brand, right? That's what, like, over the last 15, 20 years, everybody I've worked with, everybody I've built a relationship with. And to your point, like, I love, I always tell people it's like a sick passion of mine. But I love to help people find jobs. Like, that is, like, because if I know a business owner or a hiring manager and I know a great candidate, like, put them together. And I love it. And, like, to me, like, I get so much gratification from that. And, like, it doesn't really, it doesn't do anything for me or my business or whatever.

Like, ultimately, maybe it does, but, like, I love that. And what you end up doing is you're building trusted relationships. Going to have coffee with someone or drinks with someone is cool. One time doesn't really work, right? How many times do you, if you've met someone once and then two years later, like, hey, remember to grab coffee? And you're like, oh, like, yeah, I remember. And you look them up really quick because you don't have coffee. Like, it's, like, it doesn't actually move the needle. It's finding common grounds. It's finding, like, things that you can, like, bond over and that you can work together on. It doesn't necessarily lead to business, but if you could add value and help someone else out, and then you can meet them again, and you could actually build a really strong, sound relationship.

And over time, that will allow you, like, it doesn't happen in a day, right? But, like, that network continues to be built. And you have to work hard to nurture it. You have to, you know, be thoughtful about it. But it snowballs, right? It's exponential to some extent. And, you know, that's, in my opinion, the way that I look at it. When it comes to, I think your second question was, how would you do it today? Yeah, like, how would you, like, in this environment? Because what I worry about here is I was given the opportunity to have deeper and healthier relationships because I could go meet anybody, anywhere, at any time. And that face-to-face, sitting down, talking shit, grabbing a few drinks, getting a little drunk, you know, that type of thing, those things matter.

But now, I feel like this whole generation that's coming into the workforce right now is being robbed of that. So, do you have any thoughts on how to, as a young business person, outside of your college, right? Because I think a lot of times you have your networking college that you try to tap into, right? But when you're in the business world, how would you even approach networking in this environment? So, Zooming's really hard, right? Like, because it's really easy for someone on the other side of the conversation to be checked out. So, it's really difficult, to your point. And then the other thing I'll say is that at LearnCore, we did a horrible job marketing. It was all just, I mean, bootstrap company.

And if we could do one thing, we were going to spend way more time and money in marketing. But the best thing that we did from a marketing standpoint were these little events. And you were a few of them in Boston. And we would go around the country, and we'd get 15 or 20 people in a room. We'd buy them drinks, and we wouldn't say a word. We'd just talk, and we'd let them talk to each other. And then we came out of it with our customers are happy, our prospects are happy, the thought leaders, the people that are speaking were happy. And it was a great event for everybody. And you can't do that now, to your point. I mean, you do virtual events, but, like, there are a ton of virtual events. So, it's hard for your startup to get traction with those.

So, from a networking standpoint, I don't know what the, like, you know, obviously, you have to get in front of certain people as you can. But it has to really, really be value-added now. So, like, if it might be fewer conversations, but more impactful, more value-add, if there's something that you can offer someone, or you have something really that's really pressing, and you can get connected to people who really, one, care about startups, but are interested and excited to share their insights and their thoughts, those people will be really good door-openers at some point, I'd imagine, too. But it's just, it's being selected. And if you used to have, you know, meet five people a week, maybe just try to meet one person a week who you can actually add value to, and you can connect with them at a deeper level.

But it's also just really, really understanding your network, and who your friends know, and who your family knows, and who your co-workers know, or former co-workers, and whatever it is. And, like, asking all those questions, almost qualifying your networking activities before you ask for the intro, because it has to be, you know, it has to be good, or it's going to be, or it's going to be forgotten. And that's been scary. Yeah, and that's my fear, right? It's like, you have a, you know, these informational interviews and stuff like that. Look, I did them, you know, when I was coming out of college. You know, I think they're a little bit overplayed these days, and I wish kids would, like, I wish there would be just a quick little handout for kids to say how to run an informational interview.

Don't just show up and say, tell me about your background, you know, bullshit. But also, the, like, having that, I think you have a goal of meeting a certain amount of different types of people on a weekly, monthly basis. But then, you know, I think the lost art in sales is the art of the referral, right? Of asking who you had a good conversation, hey, who else should I talk to? And I don't mean from a business standpoint, like, yes, that's a lost art as well. You know, who else do you think could benefit from my services? Okay, fine. But who else do you think I should talk to based on where I am in my journey? Right? And I think that's... It's asking, it's asking for the referral. It's also thinking about who you can refer.

Pro-active. Right, yep. So not waiting for the other person to ask you, but saying, oh, John, like, you got to talk to these two people because they're, you know, growing big sales organizations. They need, they need you, right? Like, at the very least, it'll be a good conversation. Let me reach out to them, see if it's cool, and I'll connect you. And if you could do that, right, if you could leave the other person with that, you know, that's the value add piece, right? That's something that you can offer them. They're going to help you, right? Like, again, like, the give and get side of it. But at least you'll be remembered. At least there'll be some sort of connection beyond you sat on a Zoom for 25 minutes and, you know, talked about whatever, sports, whatever you want for the first 10, and nothing came out of it.

Yeah, and it's kind of like that Gary Vee jab, jab, jab, right hook, right? Or like BNI, there's a, I don't know if you're familiar with them, but Business Networking International. You know, a structured networking group, and their whole philosophy is giver's gain, right? So that actually taught me early on how to structure network, right? Because it was a weekly meeting. There was, you know, it was downtown Boston. There was 30 people. Everybody had a different skill. Everybody had a different industry. And you literally had to come with referrals. And not just, hey, here's a company you should probably call. It's like, no, no, no, no, no. Here's Ryan's name. I told him, you know, you were going to talk to him, and you should talk to him.

This is why, right? And so you stood up. You give your 30-second pitch of what you do. And then you said, I got three leads for Ryan, and this is why, right? And that giver's gain, that mentality sunk in with me early and paid so many dividends, and still does to this day, that I can't, like, to your point of doing everything you can to help as many people as you can out in the short term, like, in your early ages of sales, and then not expecting anything in return, but it will. The best quality that I look for when I hire salespeople is this idea of just being genuinely curious, right? If people are asking questions, not because it's on their script, right? If they're asking questions because they care about the answer, then they can offer help.

And that's the exact same thing in networking, right? If you're asking questions because you care, and you're interested, and you have ways you can provide value, and it's not necessarily selling your product, right? It's something else that can be valuable to the other person, then you're building a relationship, and then that will hopefully snowball from there. It's not a volume game, right? It is a quality game. Absolutely. And that actually leads, like, coming back to, like, offices, right? And so people say, like, offices are – some people think offices are dead, or people have come back to offices. I completely disagree with that. I think it will be a different type of office. It will be used for different reasons.

There will be more flexibility. People will definitely work from home, all that kind of stuff. But the number one reason – I don't know if it's the number one, but one of the most important reasons in my mind that I always come back to with why people need to go to the office are for young salespeople or young customer success people or customer service or people that, like, sit and, like, try to work independently. They have their managers, they have their team, their job is independent, right? And if they never come into the office, one, they're only going to know their team and their manager, and it's all going to be virtual. They're not going to have exposure to any other departments in the organization.

They're never going to learn what other people do. And they actually will almost get stuck into, like, a position, which may be cool. Maybe they want to just go up the ladder in sales. Maybe they don't. Maybe they want to be in marketing. Maybe they want to be in customer success. Maybe they want to be in human resources. Who knows? But, like, if they're only in that one role and it's all virtual, there's the opportunity to learn to network and to have, like, mobility goes away, and they won't get to meet anybody. And that, to me, is, like, the scariest part of it, which goes, you know, straight back to networking virtually. Like, it's – hopefully it ends soon, but you've got to make the most of it.

And you have to ask. You have to be proactive. You have to be more proactive than your – I don't want to call it your competition, but the other people that are in the same boat. Well, I think that's the last thing that we can, you know, dive into, which is that curiosity factor of how businesses are run. You know, the one thing I wish I had done a little bit more early in my career was paid attention. And I say that, you know, I was just there for a job, right? Well, not really, but, you know, I was doing my job. And I wasn't, you know, and when a new comp plan would get rolled out, I'd react. You know, I'd be like, all right, that's either good or bad, whatever. Fuck it. Let me go figure it out.

And then let me go sell. What I didn't pay attention to was how they rolled out that comp plan, what the communication was, what was the feedback from the team and how did they react to it? How did they fire people and let people go? You know what I mean? Like all these different pieces of what happens in business that you can learn. And if you're in, that's what my suggestion is for a lot of reps right now is if you're in a job right now where you're not thrilled, right? And you want to maybe try something different, at least if nothing else, use your situation to learn what, if not what to do, what not to do so that you can take that learnings and apply it to whatever you're going to do next.

What are some of the things that reps should be paying attention to right now? If they have that entrepreneurial itch, they're in a job right now where they're, they're okay. You know what I mean? They're, they're, they're doing their thing, but they're like, I think I want any suggestions on what to look for, what to pay attention to from a business standpoint that will help them get to that next level outside of their job. Well, of course, asking questions, but I think it's, it's understanding it's, it's actually no different than sales, right? So in sales, you're going to have a far better opportunity to close a deal. If you understand the customer's pain points and understand why and understand the process and all that kind of stuff.

It's, I don't think it's any different around thinking about your next step in the journey or starting a company or whatever it might be. It's trying to understand what are the pain points out there, right? And if you, if, if the goal is to start a company, which I think it sounds like you were asking if someone is entrepreneurial and they want to take that step, understand, is it a real problem? Talk to people, talk to the customers, right? They're not your customers, but they're the potential customers. They're the thought leaders or the experts in that space. And, you know, do your, do your prospecting, send them emails, send them in mail, send them whatever, be genuine in your, in your outreach.

Just try to have those conversations, try to understand, is it a real pain point? How big is the market? And also like that, that's actually a pet peeve of mine is that people talk about like town, right? The size of the market. Town doesn't really matter. It matters if you're, it does. I mean, I'd say it doesn't matter. We want to go out to a tiny, a tiny market, but like not every business is supposed to be a billion dollar company, right? There could be a lifestyle business that's spitting off a few hundred grand a year. It could be a nice business that has a five or $10 million exit. There could be a big lifestyle business. You could bootstrap it up to, you know, a ton of revenue or you could go down the venture route, right?

Like there are all these different routes. And so as long as it's, the market's big enough, you can figure out what path the company will take. And they're all good. They're all great paths. And a lot of times in, you know, being in the Midwest and being in the East Coast, more so than the Midwest, right? Like you look at the coast and this fundraising side of things glorified, especially in the West Coast. But in the Midwest, it hasn't really been until recently in the East Coast. It was a little before this, but like there's other ways to build businesses. And I think that if you find a, if you find a problem that you really understand, you talk to the customers, you validate it and you're passionate about it and it's a, it's a big enough market to have some sort of, you know, successful business, then those are the, those are kind of the validation steps that I would take before we do that.

But that's all having those conversations. Yeah. It's funny. Like the, if you watch, you know, Shark Tank, right? It's like anytime somebody's like, it's a $60 billion industry. And if I just got 1% of it, then I'll be, you know, and they just fucking immediately like, all right, dude, beat it. Like just shut up. Right. So, um, and I'll also on another note with the networking internally too, and they asking questions and being genuinely curious, you know, I, it, it blows me away that, that sales reps don't take the opportunity to engage with their executives who are not their boss. Right. Cause once executives, and you can, you know, tell me if I'm wrong here, but once you get to a certain level in your career, one of the things you take, most people take genuine, uh, pleasure in is helping other people out, right.

And, and, and showing them the way, if you will. So if I'm a CEO, even of a huge company and some sales rep on the ground floor comes knocking on my door and says, Hey, can I pick your brain for 30 minutes about your strategies and how you got to this and dah, dah, dah, dah. Like you'd be surprised at how many executives will actually take their time. And the amount, the lens that will put on you, as far as that kid that is now somebody that is on the up and up is, is huge. And the amount of stuff you learned from just taking that risk of asking that question to the CFO, to the, like, if you're trying to sell to CFOs, go talk to your fucking CFO and say, Hey, what are your challenges? What do you deal with?

Like that type of stuff. Right. And it's, some people will have that drive to go get those meetings. And like you said, people say yes. And I'll, on that note, like, it also is external. If you have a startup, you're a founder, don't be afraid to ask people in your network for some really, really high profile meetings. There was one time, I remember we went, we flew down to Charlotte to sit, to meet with the CEO of Red Hat. I think it was Raleigh. It was North Carolina. We met with the CEO of Red Hat. We were like 26 year old entrepreneurs and we're sitting there like, he's not our buyer, right? Like, but we had a network, we had a connection into him. We flew down there, sat with him for an hour.

And like, he was one of the nicest people we've ever met that was so helpful with our business. We never worked as Red Hat. But like that meeting, it was, it was just, it's so insightful to have those conversations. But if you don't ask, you can't get that. And it's a, it is, it's about asking, it's about your network and it's about, you know, not being afraid to have the hard conversations. Yeah. Awesome, man. Well, cool. Let's, I got to wrap it up because I got a training I got to do here in a minute or two, but, uh, uh, talk to people about like what's going on with, uh, pillar and where can they find out more information about what you're doing these days? Yeah. So pillar booth, we, uh, we make soundproof office phone booths, far cry from sales enablement, although it's not really good.

Can't wait to get mine by the way. Which is, which is because we have our, uh, we have our Jay Barrows pillar partnership coming out soon. So we're, we're on the verge of that, but there is, there is a, there is a lot of, um, a lot of similarities to the sales training and coaching world, but we, uh, you can find out more at pillarbooth.com. It's a industry, which is, is pretty early and it's growing. And as people start to go back to the office, they're going to need much more modularity, much more flexibility within their space and privacy is going to be really important. So the booths are great. They're, they're, they're high quality. They look great and they're good price. And so having, having some fun.

Love it. Awesome. And for those of you listening, it's Ryan Levitt, L E A V I T T. You can hit them up on LinkedIn and it's pillar booth, P I L L A R booth. Hey, is that the website pillarbooth.com? You got it. All right. Perfect. Awesome. Ryan. Well, man, I appreciate it. It's always great catching up with you. So fun as always. Thanks, John. No problem, man. Love, love watching the journey too. So, so keep me updated along the way and I'm looking forward to get my booth. I'm going to redo my attic and have a whole setup and I'm going to go as part of it. So anyways, hopefully you all got some value out of this and enjoy the conversation as much as I did. And like I always say, look, you know, even if you're having a shitty day, go make somebody smile today.

Cause if you make somebody smile today, you know, you had a good day. So go out there and make it happen, everybody. Thank you all very much. All right, everybody. We know that Ryan's insights were super helpful for so many of you out there. Be sure and smash that subscribe button and make sure you catch every episode of Make It Happen Mondays released every Monday, every week. Don't forget to join us at ondemand.jbarrows.com where you can subscribe and start streaming all of JBSales courses, tips, webinars, recorded live casts, Q&As, and much, much more. The journey to sales success begins with you investing in your own skills and professional development. This has been another fire episode of Make It Happen Mondays with your host, John Barrows, where we focus on selling better together.

See you next week, everybody. Thank you.