Ep 598: Scaling 8 and 9 Figure Businesses with Mike and Kass Lazerow
Rory: [00:00:00] A lot of personal brands have a bit of a fantasy about what it means to be an entrepreneur and run your own business, and you know that AJ and I have a heart for quote unquote real entrepreneurs. People who have been on the front lines, had their hands in the dirt, the people who have built real companies that have provided real jobs, serve real customers, and battled all of those headaches in between.
And a lot of the biggest personal brands in the world don’t really build large teams and ~large, ~large organizations. And so anytime we get a chance to talk to entrepreneurs who have created businesses with real, genuine enterprise value, who have had massive exits, that is somebody we ~re ~respect and admire and we want to get ahold of, and we want to introduce them to you because you might not be as familiar with them because they don’t have as big of personal brands, but financially and.
From an impact perspective, these people make a, ~a bigger, ~you know, as big if not much bigger impact [00:01:00] than the biggest personal brands in the world. And that’s what we have an opportunity to do today. You are about to meet Mike and Cass lro, who I love and adore for many reasons. We’ve got mutual friends.
I met them through will Gera, a really good friend of mine a client of Brand Builders Group, someone I’m a huge fan of. He spoke so highly of them. They’re also husband and wife, which is very rare to operate at the level that they operate at ~and ~and the companies they’ve been a part of, which is something that AJ and I have always done.
We have been business partners before we ever fell in love, and so anytime we get a chance to meet a successful married couple who’s crushing it in business, we’re paying attention, but. Let me give you a little bit of their pair pedigree here, and then I’ll introduce you to them. So they are serial entrepreneurs and they have been involved with massive companies.
So first golf.com was one of their most famous claims to fame that they had a $25 million exit as part of that business. Then they were a part of starting Buddy Media, [00:02:00] which they sold to Salesforce for. Get this. $745 million, 745 million. Dollars. They have also been advisors and angel investors to companies like Scopely, which had a $5 billion exit in 2022.
They’ve been advisors to companies like Liquid Death, which I’m a huge fan of. And they have a new book that has come, just came out it’s called Shoveling Bleep. We’ll say shoveling stuff. But a Love story. About the entrepreneur’s messy path to success. And so we’re going to hear a little bit about their messy path to success and the advice that they have for entrepreneurs and dreamers and mission-driven messengers just like you, from people who have actually done it.
They’ve been on the front lines, they’ve had their hands in the dirt, and they have shoveled some stuff. So Mike and Cass, welcome to the show, friends.
Kass: Thanks for [00:03:00] having us.
Mike: Thank you so
Kass: much.
Rory: So I would love to hear about golf.com ’cause that was like your first really big exit, right? That was your first sort of like materially successful entrepreneurial venture.
What I wanna know is what was your mindset when you started the company? What did you think it meant to be an entrepreneur? ~Her ~and then like, what was the reality that you discovered and then where were you at the end of that first one and how did you kind of ~get the, ~create the exit and like achieve that sort of first race?
’cause I look at all the things you’ve done, but that feels like it was sort of like your first race. So I’d just love to hear that story from, from each of you.
Kass: So for me, Rory, that definitely was like my first independent race. I had started an interactive arm of a agency before, but this was really my attempt at running something.
[00:04:00] And I started it with another co-founder who we had three in, in addition to Mike here. And it was a jump. To basically have independence. And for me, I wanted to build companies that had better culture, ~that had, ~where everyone owned a piece of the pie, that we were all in this together and that we actually aligned all of our interests.
So. I did that jump. It was the height of the internet, right? This was 1998 and 99. It was incredible. Obviously I thought I could take advantage of that amazing window of time not knowing the crash was coming in 2000. And you know, you start shoveling and what happens? You get punched in the face.
You know, an entrepreneur is really got. Probably 10 failures a day, these little mini micro failures. And then they’ll have one win. And it’s kind of like golf. It keeps you in the game. You have one good shot and you [00:05:00] just keep going. Right? So that was really it for us. And we got a big punch in the face and, really, ~we, we, ~we sold the company originally to chip shot.com in December of 1999. And they were going public, they were Sequoia backed, and then the call came in March of 2000 that Sequoia backed out and the crash was there and they were going bankrupt, and they were pulling us into bankruptcy as well.
Oh,
Kass: so talk about, you know, ~if, ~if anybody’s out there and they really think like, oh my God, being an entrepreneur is like so glamorous. You can do whatever you want. You know, you pick what you wanna do and everyone else can do it for you, not the case. Not the case.
Rory: What’s the reality, Mike? ~Like what, what, what?~
Like, ’cause especially with, you know, today that is what people see. It’s like, oh, there’s private jets and helicopters and fancy cars. And like, look at me. I’m on TV and I’m on big stages and I’m on the cover of a magazine, and it’s like, woo-hoo, be an [00:06:00] entrepreneur. Leave the nine to five. ~What, what’s the, ~what’s the real story, Mike?
Mike: Yeah, I think the real story is that there’s virtue and hard work and ~you know, I tell. ~You know, every young person that I speak to that we’re a 30 year overnight success story. So I started my first company at Northwestern University called University Wire and then did golf.com with Cass, and we’ve done eight companies together.
And so our biggest and what we’re known for is Buddy Media, but we learned more from the failure of golf.com initially and buying it back, and then scaling that. Than we did really at Buddy Media and even after Buddy Media working for Mark Benioff. I learned more about how big companies operate and at the end of the day, if you do.
The same thing over and over again. That’s working every day, every week, every quarter, every year. And just keep at it. You could build something big over time and Instagram and all the [00:07:00] social networks celebrate the instant win, the overnight success story, but those are very rare. Just look at your business, right?
No one knows kind of building businesses and building brands better than you and. What you’ve accomplished over many years, you probably couldn’t imagine what you do any given day. There’s only so much.
Rory: Yeah. It’s interesting to hear you say that because you know, AJ and I started our first company right outta college 2006, making cold calls out of the yellow pages, and we grew that to 5,000 clients, 200 people.
It was an eight figure business. And then we sold the company in 2018. But in, ~in, you know, ~reality, we lost the company AJ was fired by the investors. So we ended up bringing on investors and we had other partners, and then she was fired and then I resigned. And so we had a built-in equity structure and so we were able to have an exit as part of that.
But like, it was not [00:08:00] the like glamorous, oh my gosh, like ~right ~private islands and never work again and cover a magazine, but. We learned so much. Brand builders group. You know, we started in 2018. We are doing more in revenue in half the time with no debt, no investors, no partners, no audience. And it’s like, I don’t wanna say it’s easy.
It’s not at all easy. It’s nowhere close to easy. But like we learned everything in that first rodeo that it’s like. It’s a more straight path. Right, and it’s been a faster path. It sounds like you guys had something similar with Buddy Media.
Kass: Yeah, I would say so. I think, you know, we had. ~You know, ~a small win under our belt, right?
And people knew us for exiting, and I think that really helps. And Mike had done such a great job at relationship building. So you know, we started to get known in the New York [00:09:00] space as. ~You know, ~really good entrepreneurs who, like Mike said, put our head down, ~right. ~We didn’t complain about things and we actually executed what we were gonna say.
So, raising money, when it came to Buddy Media, you know, let Mike, ~you know, ~talk about this was easy. Like, ~you know, ~Mike, how long did it take you to raise the first couple million in?
Mike: Yeah, so I say it took me a week to raise it, but really a lifetime, right? Because. You know, if you are just cold calling investors, it’s very difficult.
It’s very difficult to just send an email and saying, Hey, invest in me. I’m great. Right? But if you invest in networking and building relationships and giving right, like you do Rory every day, then what you get in return is so much bigger. And so when I called our first investor, Howard Linson, who’s one of the epic.
Angel investors who funded Robinhood, the first money into Robinhood and e [00:10:00] Toro and all these great companies, I had already helped him sell another company. We built a relationship and it’s those relationships that you have to look at over a very long arc and not be transactional. So if you’re transactional, if it’s just, you know, what can you do for me today?
You’re just gonna burn through relationships. If you invest in genuine relationships, you know, that’s where it’s at. And any entrepreneur who’s not networking with investors is leaving a lot on the table.
Mm.
Rory: Yeah. ~I, ~I love, you know. One of the reasons I love talking to real entrepreneurs is because, you know when people hear like, oh, brand builders group’s, a personal brand strategy firm, like their mind goes to oh, social media and like books and speaking and TikTok and YouTube and podcasts and like one of the very first things we have to tell people is we say, look, a personal brand is none of those [00:11:00] things.
It’s much bigger. It’s the digitization of your reputation.
Kass: That’s right. It’s your
Rory: reputation. And Cass, when you say we had a reputation for not complaining, putting our nose down, hard work, executing, doing what we say we were gonna do, that’s what it takes. ~And, and, ~and part of the reason I have so much respect for entrepreneurs is ’cause you can fake a following.
Like you can fake an online following. Yeah. There’s lots of ways to fake an online following. You cannot fake a freaking $700 million business, right? Like you can’t fake a workplace culture where you attract great people. You can’t fake those things. ~And I, I kind of wish we lived, not kind of, I, ~I wish we lived in a world more where like real entrepreneurs got more attention.
But ironically they get less attention because they’ve got their head down building companies and shoveling stuff and like doing the deal every day. ~They’re not. That ~they’re not out there like celebrating themselves and promoting themselves. ’cause they’re like [00:12:00] solving problems behind the scenes. Right.
Kass: And with us when we were doing it. You know, I made Mike ~the, ~the Ford facing person of our, ~you know, ~founding group. And it was ~this ~all in trying to create his brand, his ~his like ~being synonymous with Buddy Media. ~That ~it was thought leadership, it was trust that we were going to solve your issues when it came to managing your social media because we built this incredible and leading social media marketing platform.
So it was interesting because yeah, we didn’t have any time to be like, Hey, look at us, we’re good entrepreneurs. It was more like, what could we do for the company that would actually serve the purpose of the company, the investors, and especially the employees.
Rory: Mm-hmm. I love that. ~I, ~I wanna talk to you about that because.
You know, that is very obvious, right? What you guys have built on the business side now though. So you’ve got ~your new book, your, ~your new book, shoveling [00:13:00] stuff as I’ll say it for the family friendly part of the show, but it’s called Shoveling Stuff again. A love story about the entrepreneur’s Messy path to success.
And so now you’re doing, you know, you’ve had a few exits, you’re, you’re more investors and now you’re getting opportunity to do it. I wanna ask you about the tension between building a personal brand. And building a company that has enterprise value because we seem to live at this unique intersection at Brand Builders Group, where we have a lot of people who have some real, like built some personal brands.
Like they have got large followings. ~Some of which, ~several of which are, ~we, ~we should say they’re, they’re Twitter rich, but their dollar broke. Like they’ve got these huge followings, a lot of pe, they inspire a lot of people. They got a big audience, but they. They haven’t figured out how to make much money and they’re trying to like become a real entrepreneur.
And then we have a whole bunch of these other people who have been really successful entrepreneurs who have made real money, learned real lessons, but nobody knows who they are. They have [00:14:00] no social following, they don’t get invited to speak anywhere. They have very little like media about themselves and.
We’re trying to help each side understand the other, because there’s advantages ~and ~and disadvantages of each side, and I wanted to just kind of like have you riff a little bit on. What are the advantages and disadvantages of a company having strong personal brand? You know, like cash, you said you, you guys really pushed Mike forward.
How is that a liability? How is it an asset? How do you manage it when you go to sell? And then like, how are you thinking about personal branding now, now that you’re sort of like, you know, in some ways a little bit behind the chapter of building companies?
Mike: So I’ll start with basically saying, you know, the best way to approach this is to be yourself.
You know, every time we’ve tried to be someone else, we realize that someone else has taken and it doesn’t work. And so the content we put into the world is very similar to the [00:15:00] advice we give to our a hundred plus entrepreneurs that we’ve invested in. ~And it’s. ~A lot of our cheat codes that we use to grow the business.
And so we feel good about it because the first 50 years was all about like heads down, earning reputation, money, all this stuff. And when we woke up we basically said, Hey, let’s like figure out how to scale impact. So the philanthropy side of what we’re doing, you know, helping more entrepreneurs, which isn’t philanthropy, but you know, we live in the greatest country.
And one of the reasons is because we have free markets and the ability to start businesses and fail and not have that be an albatross around our neck for the rest of our lives. And that’s a blessing that I think we overlook many days. And so when we look at. Building a business, it’s how do you use the leadership?
It could be the founder and CEO, it could be other people to communicate that you have a vision for the world in your industry and that your company [00:16:00] is the one that they will wanna work with. You know, people will work with companies that they like the people and they like the vision. You know, most industries have multiple options.
So to think that you are the only option in an industry means that it’s probably not a very big industry. You know, we also have ~beginner’s mind, a ~beginner’s mind. And to be honest, a lot of what we’ve done at Cass and Mike has been new and scary. You know, riddled with fear, right? We’re getting up and doing keynotes together for the first time, I was the one who used to do keynotes.
Now I have to watch timing and am I stepping on her toes? And you know, we wrote a book together. We never really worked together. She did ops, I did sales. And so, you know, we’re newbies. We feel like we are. Interns in this kind of social influence world, we look at what you and many of our friends have done and we kind of [00:17:00] put you on the pedestal.
And maybe one day in 10 years or 15 years, we can say to ourselves that, you know, we committed and we’ve kind of figured it out. Right now. We’re like many people in your audience that we’re just trying to figure it out, but ~what ~the way we’re figuring it out is we’re working harder than. ~E, ~you know, everyone I know in this space.
So we’ve applied the same, you know, philosophy to our personal brand of transparency, hard work, you know, putting in those extra calls as we did for all the businesses. ~I.~
Kass: And it’s about reps, right? Like everyone always thinks there’s shortcuts. When you’re an entrepreneur, there are no shortcuts, right?
It’s about doing the reps. Like if you look at our first posts versus now, right? It’s much improved. Mike, would you say that, that you regret not for us going silent kind of in social media after we sold? Would you regret that?
Mike: I mean, I wish we hadn’t. Because, you know, we helped invent social marketing at Buddy [00:18:00] Media.
We were friends with all of these people who are now influencers from Gary Vaynerchuk to Scott Galloway to, you know, name them, you know, Jimmy and Mr. Beast we’ve been on a call with. So yeah. But hindsight’s 2020. Yeah. After we sold the business, we turned inward. Our kids needed more attention. Hmm. And I think we had a little PTSD from going from zero to 50 million in annual recurring revenue in three years with offices in Singapore and London and all over the place.
So we say all the time that you can have anything and do anything. You just can’t do everything. And so one of the things we didn’t do, I. Was be public with our presence, which I wish we did, but hindsight’s 2020. Here we are.
Rory: Mm-hmm. Yeah, ~you, ~so just to double tap on something you breezed through there really quick.
Zero to [00:19:00] 50 million in recurring revenue in three years. You guys did?
Mike: Yes.
Rory: Yeah. That’s gnarly. And it took a to on us.
Mike: It’s why I weighed 40 pounds more. It’s why Cass and I weren’t connected. It’s why my cardiologist, I have an artificial heart valve, said I’m gonna die if I don’t take care of myself.
Right? So there are trade-offs to this and I don’t regret them, but nothing is free in life.
Rory: Yeah, I want to talk about that. So, specifically I wanna talk about being married in doing it right. AJ and I, we had a mutual friend. She had grown up with him and I met him in college and we started our first company together, and so we started as business partners and then it was a year into the company.
We did the like unforgivable sin. We started dating, we risked the whole company. It was just like, this is such a bad idea. We just could not help it. And we were just madly in love and we’ve been together ever since and it has totally worked out. But [00:20:00] we don’t know any other life other than working together.
And people are always like, how do you pull that off? Like, how do you not kill each other? ~How do you like,~
Kass: right.
Rory: So I would love to hear. About your marriage doing business together. What’s been awesome about it? What’s been hard about it? What advice would you give to people about when to do it, not to do it, why to do it, why not to do it.
Kass: Well, ~I, I can’t, I I’m like you, I, ~I can’t imagine working with anyone else because when you have that rhythm and that synchronicity of trust, right? That implicit trust and you don’t have these overlapping skills, and I am curious if you and AJ have overlapping skills or you’re totally separate. Separate.
~But. Separate. ~Exactly. That’s where like any good co-founding relationship, you don’t overlap, so you just kind of go down your lanes. But it’s like you have the best partner in the world because there’s so much trust, like you’re not gonna drop balls for each other. And I think because we had, we dated a [00:21:00] year and then I started this company and then I got Mike on board with golf.com and then we just kept going.
It’s been our superpower ~and I, ~and I really do love. ~You know, ~couple entrepreneurs because I feel like ~if they, ~if they’re in their own lanes, it can be the best superpower. The times I think that are difficult I think is just, there’s no end. ~Right. I. ~There’s no end. And yet at the same time I hear all of my friends who are entrepreneurs and they’re only like, let’s just say one of them is an entrepreneur, the spouse or the partners complaining because they’re always doing work.
Like we never complain ~when ~to each other, when ~we’re, ~we’re trying to catch up on work because we know we can relate so much to what we’re doing.
Rory: Mm-hmm. Yeah, that’s a good perspective. ’cause it’s just like when you’re in it together, you understand like, hey, the stakes are high. The ~like ~timelines are tight.
There’s people counting on us, we’re trying to make payroll, we’re trying to satisfy these customers. And like, versus if you don’t know that world, you’re like, why are you working? Like stop working and why
Kass: [00:22:00] aren’t you paying attention to me?
Rory: Uhhuh, right?
Kass: Yeah.
Rory: What are some, do you, have you guys created any sort of like rules or boundaries or like little relationship codes that have ~helped, ~helped you?
Because that’s, you know, ~the, ~the other part is just like, work is life, work is all the time. It’s, you know, you don’t have like different jobs that you’re like filling each other in. It’s like, okay, when we’re filling each other in on what happened this day, it’s like, effectively we’re just talking about work because we both work at the same place.
Mike: Well, I think why we’re so excited about Shoveling Blank, a love story is that the book is unique and it’s not just designed to revolutionize how you work as a leader, as an entrepreneur, but it’s really about how do you optimize a life and how do you build a life in this world, whether you’re an entrepreneur.
A small business owner, ~entrepreneur, right, ~who kind of never has enough resources, never has enough time or a leader trying to do something ~that, you know, ~with a high performing team. And so we’ve pulled back the curtain [00:23:00] on what we think are the real unfiltered cheat codes that have been game changers for us.
So for example, we have date night every Wednesday and Saturday night. There are probably 50 entrepreneurs we work with who now have date night every Wednesday
and
Mike: Saturday night. If you don’t schedule time with people who you wanna build relationships with, they will disintegrate. And so if your marriage is important, you have to prioritize it somehow.
Now, we think two date nights, if you can do it. It makes sense. And what we did is by the time ~we did, we realized [email protected]. ~We had a little money, not a lot, but we had some money, and we just hired a babysitter. We said, listen, every Wednesday, every Saturday, we will pay you whether we use you or not.
Block that time because it’s really important. And when we sold the company, [00:24:00] you know, the people who helped us in that capacity were also given. Bonuses, they helped us achieve what we achieved. And if you wanna kind of feel good, go give a big check to someone who has watched your kids like a life changing check.
Thousands of dollars, right? Because we think that the people who have helped us along the way in the non-business capacity are just as important ~and. ~These cheat codes are meant to basically let you build a life. ’cause at the end of the day, you know, if you’re successful, if you make boatloads of cash, but your life isn’t worth living, why bother?
Mm-hmm.
Mike: If you can’t help people, if you can’t have relationships that are fulfilling, if you can’t spend time with your faith, if you can’t do stuff that makes you human. Why go through the process? [00:25:00]
Rory: Mm-hmm. Yeah. That’s so good. I mean, that’s like, one of the things that inspires us is just going like, I think a big part of the first company in the first ~y you, several years, a ~couple decades of our career, I was so self-centered of like, I wanna achieve this and I want to do this.
~And then there’s a. ~Even though there’s a part of that that I look back and I go, gosh, you were such a self-centered person. There’s a power in achieving that, which is going, it wears off, and you get to a place where you go. The only thing that gives me kicks is when my clients succeed, when our employees succeed, when they make money, when they get the title ’cause and it’s like.
It’s where all my kicks come from, right? It’s like it’s the only thing that’s exciting anymore is like helping somebody else succeed. And so that’s a really beautiful place. You know, I think that people get to, certainly you guys have I want to dive in on some of just a couple cheat codes really quick.
Going back into business. There are [00:26:00] a lot of personal brands. That gets stuck in what we refer to as the swamp. So we refer to the swamp as basically between two to 4 million in annual revenue. And the idea is that like if you’re a really smart person and a really hardworking person and you’re really good at relationships, you can build a little kind of personal brand fiefdom to a two to 4 million in revenue by just basically redlining it.
Then you hit this cap to go, you don’t get to 10 million unless you get, you gotta change systems and people and processes. Like you have to become a real entrepreneur to get to like an eight figure business. What are some of the, and you guys have been on that journey before, advise several people on that, you know, that I feel like that’s ~the, ~the hardest jump to me is not starting the business and, and it’s hard to get to a million.
And, and hard even to get to 3 million. But it seems like the place where people really get [00:27:00] stuck is in that swamp because they are working so hard that they’re burning out, but they don’t have enough money to just go hire like a, you know, 10 senior leaders. But they need it, but they can’t afford it. How do you make that jump from the swamp that like two to 4 million?
To the north of 10 million where you do start to kind of get resources to be able to hire people and get stuff done. ’cause you guys have done that leap multiple times.
Mike: Yeah. So the biggest cheat code that I would share is focus and how you focus yourself shouldn’t be that different than how you would focus a business.
And I say yourself, your personal brand. So it starts in our world, we use something called the V two Mom. I’m not, I don’t need to go into the whole thing. It’s in the book. It’s vision, values, methods, obstacles and metrics. And you need a vision for yourself, for your personal brand that is achievable, that is concrete, that [00:28:00] matches the kinda life you want.
And a bad vision isn’t. I want to create a $10 million business around my personal brand. Like that’s a very valid vision. Okay? What are the values you hold? True transparency, growth, beginner’s, mindset, whatever is important to you. And then it comes down to, okay, if I wanna eventually be there, it’s not gonna happen overnight.
Last I checked, you have to do a million in revenue before you get to 10. You gotta do a hundred thousand before you get to a million. But what do you need to do today? To put yourself on that path. And I would encourage everyone to put together a timeline that they think they can do, reach their vision.
Whatever the vision is, is then double the time. ’cause it always takes twice the amount of time and double your budget. ’cause it always takes twice as much money. You don’t know you don, like building ~a housebuilding ~a house.
Rory: It’s like building [00:29:00] a house. ~Like~
Mike: building a house. Totally. And so, you know, that’s the biggest cheat code is BI.
Not only persistent, but be proactive. Don’t react to the incoming. Be proactive about what you wanna do to grow, which is what we’re doing. It’s why we launched Cass and Mike. It’s why we wrote the book, you know, we wanna scale our impact, and we thought that although we’re not measuring it in dollars right now.
We thought in order to start scaling it, getting out there again through content in a book ~was the best, ~was the number one thing we had to focus on.
Kass: I also think that when you’re in a company, and like you said, you’re stuck in the swamp, it comes down to a lot of it is operations. At that point you talked and you said, Rory, ~you know, you, ~you think you need all these managers and ~you, ~you need to hire more people and everything.
~I, ~I would challenge everyone out there to, I know they’re not gonna wanna do this, but like. Put the priority to take a look at all [00:30:00] your processes and where you have efficiencies and trying to look at, okay, wait a second, these 10 people are doing all the same thing. Could we get three of them to do all of it?
Right? And you start to look at and take apart how teams work. And it comes down, and this is what I would do at all the companies, ~it’s, ~it’s about scaling the processes. Because if you can scale those, you save money and you save time. And that’s how we would start to catapult ahead in our revenue, which would then allow us to hire the people.
And then that flywheel starts, right?
Rory: Mm-hmm. Yeah. I love that ~the, the, ~I think a lot of times entrepreneurs think. I just need to hire the person to come solve this problem. Yeah. And in my experience, it’s like if you just hire a person and you have crappy processes, now you have crappy process and an expensive person.
It’s like Exactly.
Kass: You
Rory: have
Kass: ~to, ~you have to, like, who’s gonna fail? ~Fail,~
Rory: who’s not gonna help you? Yeah. It’s like. Your [00:31:00] job is to create the process first and then bring someone in to kind of run the process. But if your processes are a disaster, like yeah, ~you just can’t, ~you just can’t outspend your way to like.
~Nope. ~Fix crappy processes. Exactly.
Kass: And ~that’s where you’re, ~that’s where the fear comes to, because ~you don’t, you, you know, ~entrepreneurs get stuck and they don’t wanna break anything. ~They think, ~they think there’s a person that’s the savior, as opposed to saying, wait a second, if we wanna get to 10, like Mike says, what do we need to do?
Okay, maybe that’s, I need 50 more clients. Okay, well, how do I have the current team service? 50 more clients? It comes down to the processes, right?
Rory: Mm-hmm. Yeah, I mean the, there’s a, you know, there’s so much culture and like entrepreneur, like just delegate or like, don’t do anything you’re not good at. Just hire someone to take care of that for you.
And it’s like, well, okay, great, but like with what money? Right? And also, like, ~I don’t have, ~I have zero time right now, so like what time do I have to like go hire the person? And there’s a part of me that wants to just go, oh yeah, I just wanna hire a [00:32:00] person and they’ll come and fix it. And that feels empowering at first.
But then it’s like it’s very hard to find good people and train ’em, and they’re usually expensive if they’re good and like all that stuff. And fixing the process seems more difficult, but actually that’s more empowering. It’s like you have control. Yes, right now. ~Go find, ~go fix the process. Document the process, codify it, train it, have it videoed.
And now you can hire someone to come run it and they’ll actually be successful. So it, it, it feels scarier and like it’s more work, but actually it’s the thing that’s in all of our control and it’s empowering to just like get it documented. And I think it’s, you know, ~there’s, when you, ~you seem to have such great superpowers working together of like, you know, Mike’s got this relationship building in the sales and cast.
You’ve got like this operations mastery and it really is. Such a great partnership. So I, I just, I love seeing [00:33:00] you work together and using each other’s strengths and, and, and being a team to do this.
Kass: Thank you.
Mike: I also don’t think it’s unique to like what we’ve experienced as husband and wife, which has been really rewarding and I couldn’t imagine any other way.
You can have similar relationships maybe without the personal intimacy with your co-founder, and I would choose your co-founder as carefully as you would your spouse. Because who you start a business with is often more important, much more important than what the business does to start because you’re constantly evolving the business.
Right. It’s easier to change business models than co-founders.
Yeah.
Mike: And so, you know, when you go into the relationship. Not only do you want different skill sets, so you can get a lot done, right? One plus one equals like 3, 4, 5, but you have to have a shared vision, common [00:34:00] values, effective communication, a growth mindset, right, and equal workload.
And then on top of it, the best entrepreneurs we found have this like self-awareness, like superpower, I would call it. That you know your weaknesses and you’re willing to let other people help you and you know your strengths. And when you have to like show up and kick some backside and so that co-founder relationship, you know, put as much time into it as you do your, like, business thinking.
Mm-hmm.
Rory: Yeah. ~That’s good. Yeah, I, ~I mean, we hear a whole lot of horror stories of partnerships. Not working out right, like business partnerships. ~That’s why~
Mike: companies fail. They either run outta money or internal fighting leads to just lack of focus and that the company eventually improves and
Kass: paralysis.
~Yeah.~
Mm-hmm. [00:35:00]
Rory: Yeah. I love this. Guys, this is so powerful. I mean, it’s just rare to have the perspective of people who have made the climb as many times as you have from many different vantage points as you have. I mean, 50 million in recurring revenue in three years is like, man, ~that is, ~that is naughty.
That’s like, the irony
Mike: ~is ~I went, you know, ~I was, ~I was proud of it. And you know, we start these conversations, we get inbound interest to sell the business and one is, you know, mark Benioff. And so I go to his house in Pacific Heights and, in San Francisco, and it’s actually two houses. One’s his office, like huge townhouses.
And you know, he just worked out and he’s sweating and he’s eating an energy bar and we’re just like jamming on the business. And he goes, you’ve made a huge mistake. I’m like, okay, probably. ~I probably made, ~I probably made 50 huge mistakes, but okay. Like, hit me. He goes, you only have 40 salespeople. You should have 400.
Hmm.
Mike: And so we were here thinking that, okay, we launched the product in [00:36:00] three years, we get to 50 million of a RR, and he is saying, oh, you’re an idiot. Like ~you didn’t high, ~you didn’t scale fast enough. I was like, yeah, you’re right. If we had, but there’s only so many people you could onboard any given time.
You know, it is what it is. We did it well.
Kass: ~That ~that’s why it was a perfect fit though.
Mike: Mm-hmm. Yeah. They had the sales team, which is why ~it. You know, ~it worked out so well.
Rory: Yeah, it’s great. You know what, mark for a cool multiple of 15, we’ll hand it right over to you, buddy, and you can plug it into your machine.
~I mean, mark,~
Mike: listen, like we never got into the business to sell it. We thought we were going public. We’d made some epic hires, CFO and a president to help you know, those public company ready. And we started these businesses just to be independent, like just to not have to sit behind a desk like we never spoke about money starting it.
We were as happy, poor as we were, [00:37:00] kind of as we are rich, we’re a little more comfortable, but we were driven by a fear of failure and just the joy of hard work more than any pot in, I. You know, the potential future, because that’s so unknown.
Mm-hmm.
Rory: Yeah. I love it. ~I I love this guys. ~Where do people go? So obviously again, the book Shoveling stuff, a love story about the entrepreneur’s messy path to success.
Where do you guys want people to go if they want to follow your journey, learn from you, get the book, et cetera?
Kass: Well, they can get the book right on Amazon. I think that’s the easiest way. And I think most people probably already ~shop, ~shop there. But if they wanna learn more about us, they can definitely go to Cass and mike.com and they can learn about what we’ve done, what we do.
They can definitely learn about all of our philanthropy, which we’re really excited about. And yeah, ~they’ll see, ~they’ll see lots of stories.
Rory: Mm-hmm. Yeah. ~It’s, ~it’s great. ~I, I, I, ~I love [00:38:00] the. Appreciation that you have for the work. ~Right. Just the joy of ~just the joy of hard work. I think in the very beginning, Mike, you said there’s, ~you know, there is like ~value in just doing good work.
~Like, I think and it, ~I think if people could fall in love with the idea of just doing good work. ~A, ~a lot of the rest of the entrepreneurial journey ~would, ~would work itself out. And I know that’s just ~like ~the core of the message, right? ~It’s just like, right.~
Kass: It’s like if you can learn to love to shovel, which is the hard work every single day, you’ll be unstoppable.
Mike: Mm-hmm. And it’s also the, you know, it’s not just kind of virtuous. I think, you know, the Bible wants you to be rich. Right. So like if you look at kind of how rich people are treated, whether it’s Abraham or others, you know, who he got wealthy on, like livestock and other stuff. They’re treated great by God, right?
Like, but what comes with [00:39:00] kind of freedom and resources is moral responsibility.
Kass: Yes.
Mike: And you know, it’s why, yeah. We live in an interesting time where there’s been a tremendous amount of money made in the world’s greatest country and we’re underperforming ~and given ~and giving back, right? Like we believe anyone who has been fortunate enough to be born in the time we’re born, educated, start businesses, you know, at a time where in the last 10,000 years, like if you were born a thousand years ago.
We’re not having this conversation. Right. And you have a responsibility. And we’ve always felt that. And ~I don’t think it, ~I think it transcends whatever religion you are. ~I. You know, ~you follow whatever kind of ethics drive your life.
Mm-hmm.
Rory: Yeah. One of my favorite verses is Colossians 3 23, [00:40:00] where it says, you know, do your work not unto earthly masters, but unto the Lord.
And it’s just like, you know, ~if, if, ~if you really did that every day, if you really said, right, my goal today is to create something, make something that would make. Like God or my Lord, proud. Right? It’s just like, think of how much intention and care and focus you would be like, ~I’m, I’m, I’m, I’m, ~I’m making the best thing I know how to make with whatever tools I have available, whether that’s a huge team or no team, a lot of capital, no capital, but it’s just like I’m dedicating my life to building something great, and that also will help other people.
And it’s like you do that long enough, eventually you get paid. Eventually the money shows up. And anyways, you guys are a great proof of that. Thank you for the stories. Thanks for the honesty. Thanks for, for, you know, weathering the storms you’ve done and for investing back into so many people now and giving so many entrepreneurs a [00:41:00] dream to like.
Do the journey. And anyways, it’s, it’s been an honor to meet you guys, get to know you a little bit and I look forward to continue to follow the journey and, and we wish you the best.
Kass: Thank you so much for having us ~r~
Mike: Thank you for the support. ~Really~
Kass: appreciate
Mike: it.