The 3 "Revenue Ceilings" That Stop Most Businesses From Hitting $10M

Sean Weisbrot: Welcome back to another episode of the We Live To Build podcast. This is 139 with Jeff Mains. He is the founder and CEO of Champion Leadership Group, a growth accelerator, which helps businesses grow from 1 million per year to 10 million per year, which is the topic for today. He's also the founder and CEO of intelligent contacts. A SaaS platform that helps hospitals make their billing as great as their bedside manner before these two businesses. He previously started and sold four additional businesses that were each grossing over 10 million annually, when he sold them. And he is also the host of SaaS Fuel, a podcast that started almost a year ago that seeks to help founders spark creative thinking on their wild journey of entrepreneurship. Thank you for taking the time to talk with me, Jeff. I appreciate it. Why don't you tell everyone. A little bit more about your journey to getting started with entrepreneurship, and then we will go into the topic of how to grow companies.

Jeff Mains: Thanks, Sean. It is great to be here and talk about building, and that's really the topic of the podcast is, how do you scale a company? a lot of my journey and background has been entrepreneurial. Yeah, I don't really know how to be an employee, and so it's one of the things that I've probably learned pretty early on and just had a real talent for finding ways to, to make money. And so whether that was, starting, a business as a, a teenager and, being my own boss, hiring people to, to do fulfillment, all the way through starting multiple companies. And so it's been a really interesting journey. overall, it's far different than what I expected it to be. The entrepreneurial journey is described as running from one crisis to another with enthusiasm. And I think that really describes my journey in a lot of ways. It always has a lot of ups and downs. It's never always up into the right, of course that's what you'd read in the magazines. That's, that's what it is. You just roll out a bed, start a company, and make a bunch of money. But it's been very different from that. A lot of ups and downs, a lot of mistakes along the way. But a lot of great moments and successes and the ability to, to give back, to the SaaS community, to give back to other business leaders andto support nonprofits is I think one of the greatest benefits of being able to do that.

Sean Weisbrot: The thing that's most prescient in my mind is you're on your fifth and sixth companies. One of them is already over 10 million. One of them is on its way to 10 million. Is there a secret recipe for getting to 10 million per year or more that you need to know before you start a company? Is there a certain kind of company that gets there or how did you come up with the idea on the fly and then said, I'm gonna figure out how to make it do 10 million, or, like, how does that work? Because I know a lot of companies that they're never gonna get there. Maybe it's the business that is the problem, the model is the problem, or maybe it's the founder that's the problem. Or maybe it's both. I don't know.

Jeff Mains: It can certainly be all of those or any combination of those. But, if you're looking to build a company, I never really started out thinking, I'm gonna get this to, to 10. It's always, what do I need to get to the next, to start it out, what do I need to do to get to one? And then what do I need to do to get to two and three and five and seven and 10 and 20? Beyond. So it's really thinking about doing things for the right next step. And I think that one of the big challenges is, reading a tactic or reading a book or hearing somebody talk about something that worked for them and thinking, Hey, I can try that and it'll work in my business, and they try it and it doesn't work. I think, well, well, that was a bad idea. And it's not necessarily that it was a bad idea, but timing matters. if you're gonna bake a cake. There's a recipe that you're following. There are steps that you have to follow and you have to do things in order. You can't, put it in the oven and then decide I'm gonna add the ingredients later on. So their process matters. And I think the same thing is true in business. If you're gonna grow a company, that the process matters in the order of operations makes a difference. So I think that's one of the things that I've learned along the way is doing things in the right order. And, how did the company get to 10 or beyond? I think it really starts with the problem that you solve and being very clear about what that problem is. Making sure it's a problem big enough to warrant a solution, is there are lots of, lots of great things out there and people solve problems that nobody really cares about except for, I mean, maybe they do a little bit. Is it a problem that needs to be solved? Is it something that someone would pay for? Is it a nice to have or is it a real need? Like people really need this and are willing to pay lots and lots of money to solve that problem. So I think that's a really good place to start, in looking for what product market fit is, with the problem that you solve.

Sean Weisbrot: You haven't raised a single dollar from outside investors before for any of these businesses? Am I right?

Jeff Mains: I funded companies in lots of different ways. Bootstrapped is by far my favorite and that the last couple have been that way and, and, will be going forward. just because it really gives you ultimate freedom. And so I've done it the other way where I've had investors, I've done debt financing, I've done a number of different ways, of, of company funding, but really being the. The master of my own destiny is, is something that is important and, and building a company not to make a quarterly number or to make an investor happy, but really being able to make the choice and have the freedom to make the choice, that's right for the company and for the employees. And for the clients long term. And so for me, that's just kind of a, a core value and, and a, a line in the sand that I drew that I'm not gonna take outside financing. If I lose that kind of control,

Sean Weisbrot: I think that's smart. I've talked to many people that have the same philosophy as you and, and I like that philosophy quite a lot. So basically what I, to go back to the question I was thinking of before, I've heard investors say, or I've heard other founders say, if you want to make a hundred million dollars, you gotta solve a billion dollar problem. Something like this. If you wanna make $10 billion, you gotta solve a hundred billion dollar problem. Right. Do you think there's any merit to that, especially on a bootstrap to profit model where your goal isn't to become a multi-billion dollar company, but something that you're happy doing 10 million a year with?

Jeff Mains: I do. I think the level of problem that you solve has to be big enough. I. To, to warrant people wanting to pay for it. And so whether it's bootstrapped and, and you can bootstrap, there have been companies that have been bootstrapped to a hundred million or, multi-billion dollars. There's lots of different ways to fund companies rather than just taking outside investment. So it's certainly possible to do that. So it's not that you can't build a hundred million dollar company or a billion dollar company. The biggest company I built was 137 million and, and again, that was with an SBA loan. That was not with any outside investment, so it can be done for sure.

Sean Weisbrot: You said that process is important. Is there a specific process that is repeatable across businesses, no matter what industry they're in? In order to scale to $10 million a year,

Jeff Mains: There is, and there's no magic formula, I can tell you that. But I think that you do this enough times and you start seeing patterns. And one of the patterns that I recognized pretty early on was, letting go and hiring good people to take on areas where my expertise was weak. And it's, honestly, that's a lot of areas, but it's understanding what those are. There are things that I'm really, really good at and there are a lot of things that I'm not very good at, at all. And there are things that I can do, but they don't bring me joy. I am not great at 'em. but I can get 'em done. And so that's, it's really difficult as an entrepreneur 'cause it's really easy for us to think that we're fantastic at everything and we can do everything. And even those things that we can do. It's sometimes really hard to let go of those and let somebody else who is their genius, take that and run with it. So I think that's one of the, the first lessons that, that I learned and, and moved from one company to another was delegation and really hiring a team that has that expertise that compliments, they have strengths where I'm weak and maybe they have weaknesses where I'm strong, but together we really form a powerhouse combination. When you can build a leadership team. An executive team like that, you really become unstoppable as a business, but it's difficult to do as a founder.

Sean Weisbrot: How long did it take for you to iron out in your mind what it is that you're good at and what you're not good at, so that you could hire for those positions?

Jeff Mains: I, I don't know that I've completely ironed that out 'cause there are a lot of things that I think I'm good at and then I meet somebody who is fantastic at and I go, well, you know. I'm not that great. So it's, it's really easy to think that we're, we're really good at things in isolation. if, if you're on a team, like say a sports team, if you're on a sportsteam of 10 people, it's not really hard to be a superstar. But then let's say you go up to a team, now you've got a hundred people. You think about, like, peewee league to, to junior high, to high school, to college to pro. And then, the more you go up in those ranks and the more you're around people that have big, big talent, you kinda realize, maybe I'm not as talented as I thought I was in that area. So I think it's a constant struggle. We don't always see our blind spots. It's why they're blind spots. It's why we need other people. And so, I still think that I'm on that journey of learning, what I don't know. And, even areas I think that I'm strong in, continuing to develop in, in areas. So, I certainly don't have all this figured out, even now. And I hope that I never do. I hope 50 years from now I look back and go, wow. What I was doing back then was completely Mickey Mouse stuff. And so, it's just, there's so much more to learn, but being around that talent level, the more the talent level goes up, the, the more, I see places that I can hand off and people do really, really well in things that I thought were pretty good at the time.

Sean Weisbrot: I don't want to say that I've figured it out either, but from the few companies that I've worked on, I've gotten a pretty good sense of what I'm good at and what I'm not good at. And I learned with my tech company what I was really not good at. but I had no choice but to learn how to do it, which was ui, ux design, road mapping for products, and these kinds of things. documentation for feature specifications. Wow. I learned a crap ton doing that. I thought I was good and then I started to have a team and they're like, no, this is absolutely horrific. You need to do it over again. And then I would, I would do it again. I would get a little bit better at it. And then eventually my CO was like, please, for the love of God, let me hire a product manager. I was like, okay, fine, fine. And then I saw what she was doing and I was like, oh, okay, I get it now. I think what I'm best at is coming up with revenue streams, ideas. Then going out and talking to people, finding out from them what they like, what they don't like, what they want, and how to get them to pay for it basically. and I think that makes me like, pretty well-suited for being a CEO. It's like, I love to network, I love to talk with people and I love to get in their heads and learn from them. and so I thought with my tech company I'd be involved heavily in the marketing and the sales and the customer service and the product, but. As I alluded to my COO was like, yeah, but you can't do that stuff. It's like, you think you're good at it and you might be actually quite good at it, but like you've gotta find one thing and you've gotta focus on that thing and you've gotta let everyone else do the rest. And even though we weren't at a point where we could have people doing all of those positions, I, I like to think I learned quite a lot. And so now I try to focus a lot more on the sales, pipeline and. And the lead gen and, the networking, finding the potential customers, talking to them and, and this kind of stuff. So, but I'm still excited because I know there's a lot more to learn. So I'm curious from your side, what do you think you're best at and that you like to do, and what is it that you do? Know that you're good at it, but you don't like to do it.

Jeff Mains: I think sales and relationships, those are two things that I've been very good at over the years and being able to build relationships, and I think that's, that's what makes sales fun. That's what makes sales effective, is building relationships, is not, not about having conversations with somebody just because you want something, but being genuinely interested in, in who they are and what they're doing and, and how, how we can solve a problem for them or make their life better in some way. So I think that's part of it. I'd also say, team leadership, casting vision, just being able to, to inspire people, motivate people. Sometimes it's almost scary. How much loyalty there is in the company. And so it's, it's, it's a tremendous gift and so I have to be very careful with that gift. I mean, that, that's the way I look at it, is because they're giving me that gift of trust. And so it's, it's being very careful with that gift and making sure that I'm leading them in that direction. If they want to over commit or they want to, loyalty is, I, I think, sometimes can be a scary thing where they're just completely committed and sold out to the, the company or to the, the purpose or, or to our clients. And, and I think that's incredibly admirable. So it's really important for me to make sure that I'm leading them well and leading them in the right direction.

Sean Weisbrot: That's where you get these kinds of guys, like Steve Jobs, who create these cults of personality. Where you have this incredible loyalty, even when sometimes it's maybe not really deserved because of the way they treat people.

Jeff Mains: Dunno, he personally never had the opportunity to meet him. But, there are definitely some stories out there. both, both good and bad about, leadership style.

Sean Weisbrot: What's something that you've had to change about yourself through the process of starting all of these companies?

Jeff Mains: A big one is just becoming more outgoing. I mean, a lot of people think I'm an extrovert and, and I'm really not at all. Which is, is funny because from the outside you're like, well, you do all this stuff and I'm really an introvert who does extroverted things and, and I really enjoy that. But I get recharged by withdrawing, be, alone time, quiet, that's put me in a party and I'm like, not, not to. The, the greatest environment, I'd rather be home doing nothing. I don't know that I ever do nothing, but it's one of those things that people would be really surprised at. And, particularly how does that square with sales, how can you possibly be good at sales and be an introvert? And I think it's curiosity, it's relationships, it's spending time with people, but not necessarily, big groups being the dancing bear. Although that's, what I end up doing sometimes

Sean Weisbrot: I feel we're very similar in that regard because like I may spend a few hours a day talking to different people, whether it's for business or family, friends, whatever. I'm like, I spend hours a day talking to people, and the only way that I have the energy to do that is if I also spend a few hours a day just by myself going for walks. meditating at the gym with, music on, or a podcast just like by myself. I think we have to, or else we'll burn out from just giving away too much of ourselves.

Jeff Mains: It's important to have that to, to really know yourself and have that time to recharge, to re rebuild, regenerate.

Sean Weisbrot: How do you come up with an idea for another business?

Jeff Mains: It's been different every time. Sometimes it's a problem that I'm having or experiencing, sometimes it's a problem that I see in the marketplace. A company prior to this was really something that, I guess two companies ago, as another SaaS company before this, prior to that, was a mortgage outsourcing company. And so it was really a problem that I saw, that I was experiencing myself. And, it was that loans couldn't be closed fast enough. So started a company specifically for that, partnered up with somebody who was in that space and knew it really well and had, he was in the sales and had big frustrations because he wasn't getting loans closed either, and he wasn't getting paid 'cause they couldn't close him fast enough. And I'm, I was buying properties and I couldn't buy 'em fast enough. I couldn't get deals done. And so I really started the company specifically for that, to solve a problem. I've also, in this example with intelligent contacts, really saw an opportunity in the marketplace. So it wasn't a problem that I was experiencing, but in the prior SaaS company, it was a CRM type product. And so a lot of the partners that we were working with, do some of the pieces that we do today and communications and payments, and nobody was doing it online. Everything was an on-premise solution. And so I saw there's a real opportunity to take that to the next level and, and, and build a SaaS. Around communications, unified communications and payments, and unite those two things together. And originally started doing that, the concept around the CRM, but it made a lot more, a lot more sense instead of just building it to go with that, to exit that company and, and build it independently. So then we could work with any CRM and, and that just kinda led into healthcare. So how can we use the technology that we've got for communication and payments? To help hospitals, health systems, physician practices, labs, fix the billing process that was extremely broken. And so again, it kind of led back to a problem that, was, was very familiar to me with, with family members and, healthcare issues and things like that, and dealing with, a really broken billing system. And so how can we take that and use that to, to fix a problem in the marketplace? So I think it's gonna come full circle.

Sean Weisbrot: After an idea comes to you, what do you do before you decide whether to pursue it or not?

Jeff Mains: Looking at the marketplace, are there competitors? Is there a solution out there that really fits something? Is there something that, what are the alternatives? And kind of looking at that, because I don't want to just be another me too, what can we do? What can I build? What can I do, how can I fit into the marketplace and be different? So I think that's one of the big ones, what is the opportunity? How is it different? How would it be differentiated? Is there something that's pretty close? Is this just, another, another me too solution? and is it really gonna solve a problem? Is it something that is needed in the marketplace? Because I have lots of ideas that, yeah, sometimes I think they're great ideas and you start talking to the target market and you find out that, yeah, it may be a little bit of, may be a little bit painful for them. But it's not something that they're just desperate to solve. And I think that's where entrepreneurs will get tripped up, if they see something, they'll see a problem in the marketplace and it may be a problem, but not all problems are painful. And if it's not a painful problem, nobody's gonna pay to solve it. We deal with problems all the time. There are lots of problems, that, that you have that, I have that, that everybody listening has. And we just live with them because it's, it's not painful. It's really not that big a deal. Maybe it's a minor inconvenience, but we're not gonna pay to solve it. It is just, it is what it is until some solution comes along or, until it becomes painful. And so that happens too. So you have problems that are not a big deal and then it becomes painful. And now I've gotta find a solution. So, is there some sort of a trigger event? Where one of those problems becomes painful enough for somebody to go out and look for a solution, and if so, is that on a wide, wide enough scale to build a business?

Sean Weisbrot: If you're looking to know the secrets of how to go from 1 million to 10 million, I promise you we're getting there soon. So there's just a little bit more that I want to ask that will get us there. Once you've determined that an idea is worth pursuing and turning into a business. On average, how quickly do you get that first dollar of revenue from your experience?

Jeff Mains: I think it's really important to get to that point, to get to revenue really fast, because revenue is what validates the idea. If you're building something for, 1, 2, 3, 5 years, you, you're basically, you're creating a museum for one. But it's, it's because good ideas are a dime a dozen. it's the implementation and the execution of those ideas. Getting somebody to pay for it. Even doing surveys or doing market surveys, and, and asking people, is this a solution that you would pay for? Here's a prototype. Would you buy this? It depends on who you ask. A lot of times you'll get, yeah, I would until you say, okay, sign up, sign here. Well, I really don't want to do that. So I think the revenue is the validation of the idea. And so the sooner you can get to revenue. Even even doing something that's, we actually teach this and that accelerator, how you can build and have clients fund your solution. And so I think that's a really interesting concept, being having your prospects actually pre-buy something that doesn't exist yet because they're gonna get it and you're gonna build it. So, validating and how quickly you can get your revenue, I think is one of the ways that you validate the idea. So the sooner you can do that, maybe it's month one. I wouldn't go more than, than probably six months without seeing that revenue come in the door.

Sean Weisbrot: For your businesses so far, what have you seen the average time to first dollar in?

Jeff Mains: A lot of times it is within the first few months, first two to three months, we, we've got, paying customers and, and they're live, they're, they're using something. Maybe it is an alpha version, a beta version, something that's very early, minimum we hear about minimum viable product and that's cool and all. But, a friend of mine, Jim Kane, came up with an even better term and that's minimum sellable product, so what is it that you can sell and do that very quickly? So is there an absolute minimum feature set that you can deliver in a very short period of time to start generating some revenue? To get that flywheel going and so you can continue to enhance the product.

Sean Weisbrot: So once you have the first dollar in, how do you take it to a million dollars? And from your business's experience, how often does it take to get to a million dollars? annual revenue?

Jeff Mains: It depends on the industry. I've done it as fast as, a few months and, taken as long as a couple of years. So it kind of depends on the industry and, and what you're selling. And the price point, I think, plays a very big role in that. So if you're talking about how do you get to a million dollars in revenue, well, you could sell a million things at a dollar and, and that may be really slow. It could be really fast. You could sell a thousand things at, at $83 a month. you could sell, I have to figure out that. The math, I think that's right. you could sell one thing for a million dollars. So, what is it that your pricing model is? How quickly can you get to a million? Well, if it takes, if you're selling one thing at a million dollars and it takes you six months to sell, to sell one, well now you're there in six months and maybe 12 months. Now you're at two. Where if you're trying to sell a million things at a dollar, it may be a very slow process, or it could be super fast. I mean, is it a pet rock? I don't know. So I think the product makes a difference in your market. And just the speed of the transaction. The speed of, of, the sales cycle. And so how quickly can you get the sales cycle moving forward? What does that look like? And making sure that the dollar amount is, warrants that. So what does it cost you to get a sale? And if it costs you $5 to get that, that sale that you're, you're selling, a million things for a dollar. Then, you know you're gonna be upside down by $4 million by the time you get to a million. So making sure that the economics are correct and that the front end is really, really important.

Sean Weisbrot: There are a number of businesses that, for some reason or another, are able to reach a million dollars in a single year, and a lot of them fall apart after that and they never recover. So assuming our. Mythical company reaches a million dollars in a single year. What should they be thinking about to make sure that even if they don't grow that next year, let, let, let's assume they've, they've done a million dollars by the end of 365 days from the day they start, right? What should they be thinking about in order to make sure that even if they don't grow, they also don't shrink in that second year

Jeff Mains: margin? fundamentals matter. And so building a business that makes money, I think particularly in the SaaS space. and, and kinda business in, in general. Somehow the ideas come along that it's okay to lose money for infinity, at least for a while. And, and we'll make that up because we're gonna get market share. We're gonna do volume, but fundamentals matter. It is building a profitable business model from the beginning. And I think that's one of the reasons that I love Bootstrappers so much. If they do, they have it figured out. And so it's not just trying to buy market share or it is, it's not building a bad business or, you, you're doing it with a whole lot of capital, but you're running in a capital efficient way. You're doing it profitably. You have a model that is sustainable over time. So I think, how do you get it, how do you keep it? At one and get to two or keep it at one and not go backwards, I think is fundamentally building a model that has margin and profit built into it.

Sean Weisbrot: What separates a company from remaining stagnant at that 1,000,001 that can get to the next level? Let's say 2 million.

Jeff Mains: There are really three transition points on the way to 10 million in revenue. One will come sometime between one and 2 million. There's another one, three to five. A lot of companies will get stuck right there at the four to $5 million range. And then another one, kind of seven or eight trying to, to get to 10 and one to two. One of the key things is the team. So growing beyond the founder, a lot of times at a, at a million, the bottleneck is the founder. And, and that, that's not a popular thing to say necessarily, but it's true. But it's about the founder bringing in other people that have the expertise. It's about letting go of things and not holding on so tight. And that's, that's a really hard lesson to learn, particularly early on, first couple of startups and even now, and every time, a company, these are lessons that I know and, and I absolutely know in my heart that this is the right thing to do and let it go. But it doesn't mean that it's easy because I've done all this work. I got to a million and it's my baby. it's taking that, you're handing off something that, is, is a big, big trust, big responsibility to somebody else. And so to see them take off and, and go is fantastic. But it doesn't always work that way. Sometimes you make a mishi, you bring somebody in and they let you down, that makes it that much more difficult, because you've been burned to, to let that go again. I hired a salesperson and they were terrible, and so I can't ever hire salespeople again. I'm the only one that can do that. Well, the company is never gonna scale. If it's being held back by one person. So it's, how do you eliminate those bottlenecks and how do you find the right people and get them in the right places to help carry the load?

Sean Weisbrot: So that's what starts to get a company from one to two. Yes. Yes. Is there a specific example in which you had an issue letting go that caused your business? It took longer to grow because of that? I think that always

Jeff Mains: happens, every, every single time. Like I said, it's hard to do. Even when I know that it's time, it's still hard to let go. And so it is really finding the person, and there've been times where I've hired, I have hired the wrong person, I've hired the wrong person, and, and have lost millions. And that makes it just that much more difficult and painful to try again. But I know that the path to success is finding somebody that really has that genius that can take an area of the business and, and just blow it up.

Sean Weisbrot: What specifically has been your most costly mistake to date? And if you could put a number on that, that would be interesting.

Jeff Mains: I actually brought somebody in, in an area of the business, particularly in, in this company, in payments, that, I really had no experience in that and was looking for somebody that did. And, they were supposed to be experts. Just the way that the system works. I mean, they did really well for the, the revenue side, temporarily. And, it went up and up and things looked like they were going really, really well. And, and then things kind of fell apart, fairly suddenly. And, so there was some, some fraud and some other things going on, but we ended up, upside down 5 million. So, you think starting at zero is hard. Now try restarting at minus five and now you've gotta build back up, past that and then, do it all over again. So that's a, it's a costly mistake in hiring the wrong people. And there were definitely signs there, beforehand, but, it's hard to admit it's a mistake. So, as a leader, I think that's something that we've gotta be good at is, admitting our mistakes and, and cutting our losses earlier. So that's another thing that's really difficult, when we make a mistake, admit it, cut the loss, and make the right choice. But sometimes we wanna hold onto those wrong choices for a long time because it just feels good. We don't wanna say it was a bad choice. Even though you know anybody from the outside looking at it, we go, that was really dumb.

Sean Weisbrot: Yeah, I've made those kinds of mistakes before. Never worth 5 million. Thankfully, but, still painful nonetheless. So let's say we've gotten our company to 2 million. We've started to think about team, process, economic economics per unit. What do we need to then change to go from two to a, let's say four,

Jeff Mains: two to four? The team is gonna start growing. So one of the first things that's gonna be strained is process. And so getting, getting knowledge transferred over to new team members. And so having a structured process, getting knowledge out of people's heads and into documentation, into a formal process. And, it's one of those things that I think is really difficult a lot of times as founders, because we want the culture to be fun. We want it to be free. We don't want all those constraints of the corporate world, right. And so, you think well, that's not gonna be any fun. We're gonna take the life out of the company, but it's actually the opposite. You're really giving life to the company and allowing it to breathe and allowing new, new people to come in. You think about a body and cell division, so you have two cells and now, or you have one cell in it that splits into two and two into four and, and and goes on. And I think growing a company is very similar to that, but you want that DNA to be passed on within the organization so that you keep the structured processes, you keep the things that are made. Make you successfuland take that to the next generation. But it doesn't stop there. Once processes are in place, that's the starting point. It's not the ending point. You think, Hey, I, I just created these processes. Now why are we going and revisiting them? But as the company continues to grow, those will expand. As you bring in new talent, you bring in people who, who know more, that have more expertise, they're able to take that to the next iteration, the next iteration, the next iteration. I think that's a really important thing to keep. You don't wanna be stagnant. We do want those processes in place. You want a way to do things. You have your way, but it's not something that is your way forever. It'ssomething that does change over time.

Sean Weisbrot: So at that size, revenue, would, if you were hiring someone, would you expect all of the processes and documentation for that position? To be mapped out and ready for them to walk into, or would you expect it not to be great and hope that they kind of like to fix it in the beginning of their job, like their time working with you?

Jeff Mains: I don't think they, they all have to be, completely mapped out, but one of the worst things you can do is hire somebody into a, a new position that doesn't even exist yet. Kind of throw 'em into it and say, welcome. Go figure it out. That happens all the time. I've done it probably way too many times and for everybody. I've done that too. I apologize. Here we go. Public apology, no. Having, making sure that, that somebody is doing that role because somebody is, is doing some sort of function in that role, it may not be great. Having some sort of documentation, some sort of, here's how we do it today. And, giving them the expectation, giving them the freedom to make it better. But I think it is important, at least having some sort of a framework that they can walk into, some context instead of just, Hey, here's a new role. Nobody's ever done this before. I hope you figure it out. That's a recipe for disaster.

Sean Weisbrot: Yeah, I think I've pissed off a number of my employees. It was never my goal. But as I said, when I first started out, I didn't know anything about tech. And so, like my first hire was the lead engineer who was responsible for the architecting of the infrastructure of the backend. And he was like, okay, well make me some wire frames and tell me what everything does. I didn't know what I was doing, so we wasted months because I created this massive thing that I thought was amazing, and he was like, this is trash. Do it again. I was like, I just spent like three months making this for you. He's like, it's trash. Do it again.

Jeff Mains: Yeah, that's where collaboration is certainly helpful.

Sean Weisbrot: Well, the thing is, it was my vision and he didn't understand what I wanted to build until I gave him more information. So it was completely on me. There was literally just me and him. There was nobody else. So he was like, I can build anything you want as long as I know what it is that you want, and if you don't know how to tell me what you want, I can't build it for you. And I was like, you make a lot of sense, but I've never done this before, so I need you to teach me how to do it so I can do it for you. And, and so it took like five or six months before we finally had something that we could work with. And even then when we went to go hire the product manager, everything was still a freaking mess because the documentation didn't match the designs sometimes, right? So we would say, oh, here's a feature, here's what the feature does. But if you look at the designs, maybe the color was different from what it said it should be, or maybe, it didn't do things exactly, or it was coded in a way that the specifications and the coding didn't line up. So what you actually experienced based on what it said it should do, wasn't right. major, major problems that took a very long time to fix. And unfortunately, the QA manager and the product manager had to work with the who, the guy who became the CTO, as well as the developers and the testers to fix all of it. I mean, we spent probably six months at least just going through every screen and every feature, making sure that. The documentation aligned with what was coded and what was designed and made them all mesh together. It took forever and she was basically thrown into it, and I tried so hard to make it as good as possible for her when she arrived, but wow, I am never gonna let that happen again. There's some good lessons I hope. I hope and if I do let it happen again, hopefully there's more money to be able to pay someone more money to deal with the BS that they have to deal with. You were saying that there's something that prevents people from going from four to five. What is that?

Jeff Mains: I think it's learning to manage through people, so by the time you get to 5 million, you typically have your executive team and, and it's pretty easy to, to manage direct reports. Then you probably have a second layer depending on the type of company. You may even have a third layer. And so the, the further removed you are from, the, the, the people actually doing the work, the, the more difficult it is to manage and to keep that, that, that corporate DNA to keep that culture intact. And so, I think that one of the big challenges is learning to manage through people, not just manage people directly. And for a lot of founders, they don't have a lot of management experience. A lot of the SaaS founders we workwith come from backgrounds that are development, so they've been technical. They haven't been, maybe they were team leaders. But leading a company is, is a different experience for them. They could be finance people, they could be marketing people, sales, lots of different backgrounds. So it's just a different skill to learn to, to not only manage direct reports, but how do you manage through the team? How do you make sure that that vision translates and gets all the way down? And it gets increasingly harder as the company gets bigger because you get further and further away. So how do you, how do you make sure that everybody is engaged and really catches the vision as you're putting it out there?

Sean Weisbrot: So how do you do that? How do you learn to manage their people?

Jeff Mains: Part of it, I think, is in culture and, and really being very specific, being very intentional about building culture from the beginning. So, I mean, I look at it and the first thing I'll do is I'll hire for fit. before I hire for skill. Skills can be taught. And, even the most skilled person can come in and they probably still only know 50, 60, 70% of what they need to know. But that fit is one of the most important things. So they buy into the mission, the vision, the purpose, the core values of the company. But in order for them to do that, they need to know what they are. And you have to have defined it. And so I think that's something we're really an early step to do in a company. Is to do that. But it doesn't start with a mission or vision. It actually starts the opposite of that. People talk about mission and backing into core values, but it starts the opposite. It starts with your core values and that really leads to your vision and leads to your mission and your purpose. And so it really starts with that. And so you're hiring people that are in alignment with those core values of your organization and that also have the right skills. So putting the right people in the right places. So I think that's the beginning part of it, and then staying close to them. So, doing regular, regular meetings, doing things that are, are group oriented. and the same thing is true even with your clients. The, the, the bigger you get as an organization, it's very easy as a leader to be far removed from that client experience. So I think it's super important to make sure that you stay engaged. with the clients that you stay, very close to them in that process and spend time. And one of the most valuable things you can do as a CEO is spend time with clients to really understand what it is that they're going through so you don't lose touch, because you're building the tech empire building, the next greatest solution. And, it's easy to get into that bubble of doing lots of cool things. Or doing lots of things you think need to be done for the organization and losing touch with that end client

Sean Weisbrot: In terms of hiring for fit, how do you suggest a company does that? And I'll, I'll tell you real fast how I tried to do that. So I would be the first person, or I am the first person that someone would talk to, right? So if we put out a job ad and someone. Actually clicks on the link and, and applies rather than just hitting the apply button on LinkedIn and ignoring our, our instructions. But if they, if they, they actually pay attention and, and pass, I'm the first person that they would have, an email with and I would then invite them to click on the link to schedule a time in my calendar if they said I'm available at this time, instant fail because that's not the instructions. The instructions are, pick a time from my calendar. If they actually do that correctly, they'll get a 30 minute call with me by video, and I'll go over why I built the company, what we're looking for in someone, and just kind of get a fit for who they are. And then if I like them, then I'll pass them on to the hiring manager who will then start performing this. The hard skills test. Now I had a conversation with some and, and there's a little bit more to that as well, from there. But obviously, I think the first part is the most important. And the reason I do that is because I feel like if they pass a skills test, fantastic, but if they don't pass a, but if they pass a skills test and then not the culture test, I've wasted the team's time. If they, if they pass my culture test, but then fail the hard skills test. No harm, no foul. So I feel like my time is less valuable than the team's time, and I'd rather protect them by only introducing them, people that I think are going to fit, but then letting them tell me who actually has the skills to do it. Now, I had a conversation recently with a guy who's running a multimillion dollar business and he said that he does things opposite. He has the team do everything first, and then if they pass all of that, then they get the ability to talk to him and he's the last person they talk to because he sees his time as the most valuable. What do you think? Yeah, I've seen

Jeff Mains: It works both ways. Yeah. The most important piece we spend a lot of time thinking about, like, the customer journey and mapping that out and trying to create that experience. I think the most important thing is making sure that you have that same experience for your team. Or your future potential team and your candidates that you've thought about, what does that journey look like? How do we get them through the process in a way that feels really good to them? That gives us the information that we need to make a decision, but especially in today's environment, that gives them the information they need to make a decision. Is this gonna be a good, a good place for them where they're gonna thrive and do really, really well and, and give them the ability to, to not do that? There was a story, um. I assume it's true, with, I think it was Zappos that, they would do the interview process and actually give people an opportunity, before they hired, we'll give you $1,500 right now to walk away and drop outta this process right now. And, but it saved them a ton because it prevented somebody from, from just job hopping or just, there, there wasn't gonna stick around anyway. That didn't really buy into what they were doing. The culture. Really wanted to be a part of that company, I thought, now that's really interesting to think about, but it's really creating that experience, that allows somebody to, to say, yes, this is a fit for me. This is where I want to be long term. And I really see myself as contributing here. And I, I'm, I'm, I'm all in. And that's really what I think we're looking for. So it doesn't necessarily matter if you start at the top or you start somewhere else down the line. At some point the company gets too big and the CEO can't interview every single person. And so, what does that look like as the company continues to scale? I think it's something that evolves, but I've seen it work well both ways, where, the, the, the top person is one of the first contacts and I've seen it work well, where they are, one of the, the last contacts. And then the company grows to a place where that goes down a level and maybe it's the VP or the department head that becomes that first or last contact.

Sean Weisbrot: Yeah. My thinking was I would probably do that to the first hundred and then after that, like revisit it.

Jeff Mains: It depends on, on how many people you're hiring and how fast as well. So, if you're, if you're growing quickly and you're hiring 20 people a week, well, you may have to interview a hundred people to do that. It becomes unscalable pretty quickly.

Sean Weisbrot: Right. No, I mean, I'm doing a VC funded startup, so there might be like, okay, in the next 18 months we're gonna hire 50 people, a hundred people.

Jeff Mains: That may be feasible, but at some point it's really balancing your time. And is that the most valuable use of your time as a leader and, for some companies, some positions? Absolutely. It would be, for every position in the organization, probably not.

Sean Weisbrot: I just know that of all the people. I'm the one that is able to best express the culture and what we're doing and why. 'cause I, I left other people that were running the hiring process to do that and I just didn't get the same kind of excitement from the people we hired when I left that, when I took myself out of that process. So I felt like it was really important for me to put myself back in it, and I felt like it was a very important part of my job.

Jeff Mains: I've experienced that as well. and when that's happened, it's, it's really been because I have not passed on the DNA well enough to the, the leadership team or to whoever it is that's making those decisions. so much so that they would make the same decision that I would make in that same situation.

Sean Weisbrot: What is the next level before 10 million and how do you get there? From four or five,

Jeff Mains: typically it is a, around, seven, seven to eight is kind of the next, what I call revenue ceiling. It just, companies will get up around that range and then they just kind of hover there and it takes, some big event, to get them over the hump. to get to 10.

Sean Weisbrot: What's an example of a hump?

Jeff Mains: Said this. Yeah. Went back at, one to two. A lot of times it's, it's leadership. So in order to continue growth, a company will rarely outgrow its leader, and, and that includes the, the leadership team as well. And so the, the, the person that you hire, the level of person that you hire to get you from one to two is probably not the same level of person you need to get to seven to 10 or 10 to 20 or or beyond. And so yeah, as a leader continuing to, to grow your skills. Doing the same things, following the same processes, doing just more, doing more of what you have been doing to get from two to five, or maybe even five to seven, is not going to get you to 10. And so it is a fundamental shift, I think, in the leadership, in the mindset and continuing to grow and, and really focus in. So it's a function of where you're spending your time. So you'll spend your time very differently running a $1 million company than you do. seven or $10 million company. but it takes personal growth to do that. It takes growth, as a business. just business acumen. Just a business leadership growth to, to what I call, fill the chair. I. And so, like I said, a company will rarely outgrow its leader. And so what happens is they get stuck at that point. And again, it takes a shift in the person. And that could be a leadership team change. It could be expanding capabilities. And so now the people that you had, this is one of the challenges with giving people like titles. Well over their qualifications is as the company continues to grow, now what do you do? Do you take that person? You say, okay, I know you've been a Chief Revenue officer, but now you're gonna be VP of sales, or, or something else, because we need a real chief revenue officer at this stage to get to, to 20 from where we are here. So that can become some really sticky conversations. And a lot of times, I mean, sometimes it is, replacing somebody that just doesn't have the, the, the scale, they, they can't scale. Two to 10 or to 20, or wherever it is that you want to go next. So I think, those are some, some real interesting things, challenges, as leaders, we have to think about, what is holding back growth to get us from here to that next level? Is it bringing somebody in? Do I need to change how I'm doing things, how I'm leading? Do we need different leadership in a particular area, whether that be sales or marketing or HR or operations. where, where are the constraints?

Sean Weisbrot: How do you make the decision that it's one or the other, whether a person needs the opportunity to grow and, and how do you help them do that? Or we need to replace the person because it's gonna take too long for them to get there.

Jeff Mains: It's kind of a matrix. So there are people who can and have the ability. Then there are people who will, and so if they can, and they will, that's somebody that you really invest into and help them get there, if they can, and they won't. there are lots of people with, with potential and, and they just don't want to, they don't want to, to do anymore. They don't really want to grow. They're just happy where they are. And that's somebody that, sad as it is, they're probably not gonna be a fit for the organization going forward. There are people who don't have the ability, but absolutely have the will to do it. I think you can get those, those people training and coaching and, and maybe get them to that point. And then of course, they're the ones that can't do it and, and don't wanna do it. And those shouldn't be part of the organization to start with anyway. So I think there's, there's a couple of different scenarios where there's a path forward and, and one where they're, they're may not be, if somebody's just really comfortable where they are and they don't have a growth mindset and you're a, a high growth company. Then there's a mismatch there, and it's time for them to, to move on and get somebody in there that, that, that will really fit into that, the, the growth mindset and the high growth company, and give that person that's comfortable the ability to go be comfortable somewhere else, because there's probably a rollout there that would be a good fit for 'em.

Sean Weisbrot: How does a founder become self-aware that they're not the right person to continue running the company anymore?

Jeff Mains: Well, like I said earlier, we all have blind spots. And myself as well. And so I think we have advisors, and that could be a board of directors, it could be a CEO peer group. And that's one of the things that we do with Champion Leadership Group is, have a very strong peer aspect to the group, where you have kind of an informal board of advisors, we've got mentors, things like that. And so I think that's part of it. And, and again, is it something that then there's nothing wrong. As the founder was saying, Hey, I grew it this far, and, and I'm done. I don't want to go any further. And so again, is it a can do? Is it a want to? And so sometimes they can and they, they will or they want to, and, and that's something that can be trained. It's something that you get the right, the right coaching, the right support you can get there because you have the will. but there are certainly times where it's like, I, I've built this, this far. I'm tired. I want out. And, and there's nothing wrong with that either. Maybe it's not something that's, that's life giving anymore. It's something that has kind of become, I've, I've been in that place where I've been successfully stuck, built something and now I'm trapped in my own hamster wheel and I don't like this anymore. So it's, it's, what do you want to do as a founder? And so I think some of that is, is really just having honest conversations. the willingness to be honest with yourself. Is this something that I really wanna do and do I have the capability? To, to take it to the next level. and if I don't, how can I get that? How can I develop that in myself? And, and if I don't want to, well then who's the right person to take the reins? Is it hiring somebody from the outside? Is it, is it a sale? Is it an equity partner? Is it somebody from the inside that we can promote that, that may be a really good fit for that? And so that's always having a succession plan, I think is something that every company should do.

Sean Weisbrot: Let's assume you can reach that seven, 8 million per year. What is the last thing? I mean, obviously not last, but like, what's the thing you need to do that'll allow you to get to 10 or, or break beyond 10 million per year?

Jeff Mains: No matter what the revenue is, it's always about sales. And so it is sold and, and there's, early on, a lot of times, particularly in technical companies, it's all about the product. but it's never really about the product. It's about can we sell the product? Do we have something that is gonna be revenue generating? And so I think at that point it is really focusing hard, even more so double down on, on sales, on partnerships, on revenue generation. And then you get to, to 10, I mean, that is really the escape velocity. there's not a lot that will kill a $10 million company. There are certainly things that can, but a mistake that you make at 10, is not gonna be completely detrimental to a company where if you make that same mistake at one, the company's dead. And, and I think every company that gets to 10, I, I, I think entrepreneurs have more lives than a cat. If cats have nine entrepreneurs, I don't know, 10 or 20, but every company that gets to 10 million has almost died 10 times. because the journey is never just up and into the right. It's always, up and down and up and down and up and down, and, and you, you want more of those ups than downs. But it is, it is a challenge. But the things that you can do at 10 million that you can't do below that, it really opens up a lot more opportunities. So if you grow a company to one, the next million is inevitable. And I think the same thing is true. You get the 10 and, the, the next 10. Is inevitable because it, it becomes, you get that, that flywheel going and, and you're, you're continuing to to grow and grow and grow.

Sean Weisbrot: So you've heard it here from one to 10 million. I'm sure there's a lot more he knows about that, that we don't have time to go into detail. maybe there's another episode where we can go more into detail, but unfortunately there's no time left now, but. Is there anything that we haven't talked about that you'd like to add?

Jeff Mains: Sure. If you want some specific growth tips, you want to go deep, grab a copy of my book, Small Fish Big Pond, building a World Class Business that swims circles around competitors, and it's got a lot of interactive content as well to help you grow your scale, your business. And get you from where you are today to the next million, the next five, the next 10, wherever it is that you want to go. So it's not about just hitting a magic number, there's nothing magic about 10. It's about growing a business that supports you, that gets to, that meets your vision, and accomplishes what you wanna accomplish. And maybe that's five, maybe it's one, maybe it's a hundred, but whatever that number is, it's designed to, to help you. To do that and to, to move those roadblocks out of the way and blow through those revenue ceilings.