← The Futur with Chris Do
The Futur with Chris Do
336 - Risk, Failure & Growth: The Truth About Entrepreneurship - With Michael & Kass Lazerow
01:22:24
Loading summary
Transcript184 lines
- [00:00]
Cass Lazzaro
Entrepreneurs who learn to love to shovel are unstoppable, period. Those entrepreneurs out there that can sit in their fear because nobody knows what they're doing. It's a steep learning curve. But if you can sit in the fear, not try to dismiss it, but still operate in it, those are the entrepreneurs that understand what shoveling really means. And then those are the entrepreneurs that are unstoppable. Foreign.
- [00:39]
Chris Do
The way I start off my show is I. I have you all introduce yourself. And this is an interesting one because it's. It's. I think I can count on one hand the times in which I've had more than one person on. On the pod. Somebody introduce yourself and then tell us your collective stories, your individual stories, and I'll just pick it up from there.
- [00:56]
Mike Lazzaro
Yeah. So thanks for having us. Long time f fan and really excited to be here. I'm Mike Lazzaro. This is my wife of 25 years and business partner and mother of three kids and three dogs, Cass Lazaro. We started our first company when we were dating, as all people who are madly in love and newly in love do. And that company was golf.com we're both entrepreneurs. We built our businesses, you know, really starting at Cass in high school, me in college and connected over entrepreneurship and went on to start companies like Golf.com and Buddy Media, which sold to Salesforce for $745 million, which at the time was a lot of money. That seems to be a series A for this, for the world we live in today. And I'm more of the creative and sales and product and cast does everything for our life and our businesses.
- [01:51]
Cass Lazzaro
That's good, Mike. Good intro.
- [01:52]
Mike Lazzaro
Thank you. I appreciate the compliment. A rare compliment.
- [01:57]
Chris Do
Cassidy, do you miss something?
- [01:59]
Cass Lazzaro
No, I think you did it right. Like, Mike is definitely the visionary. He literally in all of our companies and when we invest in companies can help monetize anything. Think of the different models. And I usually help out with all operations, marketing, hiring, my favorite thing to do, firing, and everything in between.
- [02:20]
Chris Do
Is that said with sarcasm or are you being serious?
- [02:22]
Cass Lazzaro
No, I really do like firing. I think it's just such a task of efficiency. So the best operators out there will hire fast, but fire faster.
- [02:33]
Mike Lazzaro
But she does it with kindness, which is, you know, I think I've learned a lot from Cass and oftentimes getting fired could be an awful experience that ruins you, or it could be the best advice you've ever gotten and put you on a path of self awareness and figuring out your mishigas or where your best Fit is and cast is really good at, like, firing people and making them feel great and giving them feedback that really, I think I've seen it over and over again, changes their lives.
- [03:05]
Cass Lazzaro
My philosophy is that you spend so much time and care trying to recruit somebody for a company that you have to spend the same amount of time when you actually let them go. It's only fair and to do the right thing. This is an opportunity where someone can learn and change the trajectory of their career if they choose to listen, but you have to give them the information.
- [03:29]
Chris Do
Wow, that's a very interesting philosophy. There's so many things I want to get into in terms of, like, how you stay married and happy working together, because that's a challenge. You both have accomplished things that our audience can only dream of. And you're looking at that perspective. You have such an interesting, unique approach to firing that I have to get into. As one who struggles with it myself, and I know many of our listeners do this, and from my own history, I've been reluctant to hire people because I just didn't want to fire people. And that was an artificial constraint placed on myself. And once I learned how to deal with it, it made my life a lot easier. Of course, I can grow.
- [04:04]
Cass Lazzaro
Entrepreneurs who learn to love to shovel are unstoppable, period. Those entrepreneurs out there that can sit in their fear because nobody knows what they're doing, it's a steep learning curve. But if you can sit in the fear, not try to dismiss it, but still operate in it, those are the entrepreneurs that understand what shoveling really means. And then those are the entrepreneurs that are unstoppable.
- [04:29]
Chris Do
I think in the last couple of years, entrepreneurship has been made sexy, and somebody described it as trendy. I think Gary Vee was talking about, like, entrepreneurship is trending now. And I turned to my young staff and asked him, is it trending? I mean, I've been an entrepreneur all my life. Like, I didn't even understand that concept. And he goes, yeah, everybody wants to be in business for themselves. And if we look from the outside, especially amplified through the lens of social media, it does look sexy and fun. People posing in front of their expensive cars and the boats and the lifestyle and apartments and the boyfriends, the girlfriends, the party life. And then they forget to talk about all the stuff that no one sees. I think you. I don't swear you refer to as the s. The stuff we gotta do, right? And you're saying, like, let's get real with this. And there are sacrifices that need to be Made. And a lot of our audience are really, they're really freelancers who pretend to be entrepreneurs. And I said, stop pretending, let's be real entrepreneurs. You need to scale, you need a team, you need to learn how to delegate. And it takes a lot of work and there's a lot of sacrifice. So why don't we start off with this. What are maybe the top couple of myths that you can think about that people who are in that space do not understand anything about entrepreneurship? Whoever wants to take that, I'll start.
- [05:43]
Cass Lazzaro
I'll say that I run across this a lot with entrepreneurs who come and ask us questions, that there's this glorification that you're going to have all the time in the world, that you're literally never going to miss an event. You're never going to miss an event with your kids. Like you're going to go on vacations. You can take as much vacation time. The truth is that, that being an entrepreneur is a bunch of sacrifices. And I have a philosophy that you only can do one thing well at a time. And because of that, if you really do want to start a company and run it and do it well, you are going to sacrifice friendships, you're going to sacrifice being with family, you're going to maybe not miss things with kids, like big events like a play at the school that you can have on a calendar, but you're going to miss all the little between moments and those friendships that are family, friends, those are all like, you're just not going to get that. So I'd like to demystify that with saying that you got to be prepared and swallow this imbalanced life and be ready to have some sacrifices.
- [06:48]
Mike Lazzaro
I think you mentioned kind of one of the most toxic things to entrepreneurs, which is social media, because it's all about external validation. And it's ironic because this will probably go on social media and we helped invent the social marketing space at Buddy Media. But you have to realize that person who you mentioned in front of the Lamborghini is probably living in their parents basement and they've never built anything. And Gary V. Who you mentioned is a really interesting case because he came to us when he was 34 years old and he said, listen, I've worked for my dad's liquor store, never made more than 100 grand a year. Which living in New York City and New Jersey is, you know, after taxes, it's not a lot. I don't have money for an office. Can we use your only conference room to launch Vaynermedia and, yeah, you can't say no to Gary. He's very convincing. So I said yes right away. And I said, cass, can you talk to Gary? He wants to use our conference room. And I already told him he could. But what I saw is the hustle, real hustle, focused, strategic hustle of, like, getting customers on board, hiring people to fulfill the work. Many of your audience members are in the creative industry and could get more work, but they'd also have to get more people, right? They have to scale. That's what you're talking about with entrepreneurship. And I think if you tap into real entrepreneurs like Gary, like Mark Cuban, like others who put out content, it will help educate you. But most importantly, you have to stop worrying about what people think. If you go into this worried about perception, you are just going to be riddled with fear. That's going to cause uncertainty. Uncertainty is going to cause doubt, and you're not going to be able to get out of this hurricane of fud. And so tap into why you're different. What are the benefits you bring to the world? What do you do better than anyone else? And exploit those for the benefit of others? And that's really what business. That's what you've done. I mean, Chris, look at what you've done. You've tapped into your true kind of gifts of creativity and communication, and you've just exploited them to help people.
- [09:05]
Chris Do
I'm going to ask this question on behalf of all the partners who have to suffer with partners who do things, and then the other person has to deal with it. I'm mostly channeling my wife here. What I heard Mike say was, hey, there's this guy named Gary. Let's just let him use this thing. And then I saw a reaction from you, Cass, I need you to explain the reaction, because I don't think I'm a mind reader, but I saw something. Please expand on that.
- [09:27]
Cass Lazzaro
So we were in an office right on Columbus Circle, so 60th and Broadway. And we had, I don't know, maybe 20 desks and three offices and then a conference room, which was just basically a glorified bigger room that didn't have a partition in it. And for Mike to tell me that he'd already said yes to Gary. And then literally as we're talking, he's like, you know, I need you to get behind this. And Gary's brother AJ is like, has boxes of stuff that he's walking past me, like, hey, Cass. And, like, moving in. I was like, what the f. Did you just do so again, Gary came up to me, and he was so appreciative and genuine and thankful. It did put us in a bind. I mean, they got to, like, a number of people in that office smushed in there, and it actually became a fire code hazard. But I think that was an interesting moment for Mike and me. I was not happy about that. But in retrospect, it was fun to be in an environment where you had really focused people. And our employees could also see another group of people who had their heads down and were leading by example.
- [10:35]
Chris Do
Is there anything else you want to expand on that in terms of the feeling and how you process that? Because this is what I do to my wife all the time and to my entire team. I got this idea, let's go do this thing. And then they literally then have to go and clean up the crap afterwards. And I'm sure it's frustrating.
- [10:49]
Cass Lazzaro
It is frustrating. I mean, Mike and I, we're very different, but we're aligned on many different things. One thing we're not aligned on is when he can start talking and pitching ideas to me, and that's in the morning. So he wakes up, fired up to go and has, like, an idea, like, coming out of the shower, and then, like, opens up and goes, I have another idea. I have another idea. So, yeah, it's frustrating. I'm the one. He throws things over the fence, and I've got to, like, just like your wife, I've got to execute it. I've got to operationalize it. I got to figure it out. But it's also how we get our best ideas. Because if he throws me something that I cannot figure out how we can scale, it's a great filter for him and the things that get by the filter, or let's just say he goes around the filter, he goes around me. Those have not worked out so great.
- [11:42]
Chris Do
My God, I probably can spend all our conversation on this one thing. But I'm not going to be super selfish here. Mike, I want to ask you this question. You meet this guy. He seems like he's got a lot of energy. I think you're more of an instinctual person. Maybe I'm projecting here. What is it that you see about this young Gary Vaynerchuk who's like, we have limited office space, but why don't we share what limited resources we have with a random person? I think. Right?
- [12:05]
Mike Lazzaro
Yeah. No, I didn't know him very well. What was interesting about Gary at the time is he had a small following from his wine library. Show how he was creating content was unlike anyone out there. It was raw, it was him, he was eating dirt, he was animated. And he built this business, which I knew about. I don't drink, but I knew about the store wine Library. From about $4 million of sales to 70 million off the back of content. We launched Buddy Media to help marketers market in a whole new way, to connect with customers in a whole new way. So this is the advent of Facebook. We were part of some of the first campaigns that launched on Facebook and we just thought that content was the currency of culture. And when Gary showed up, I really liked him. I was fascinated by this creature who I'd never met. I'd never met a creature like Gary Vaynerchuk.
- [13:04]
Cass Lazzaro
He is a creature.
- [13:05]
Mike Lazzaro
And I was actually reminded we had dinner at his apartment this week and we were talking about some of the early days. He goes, I can't believe that you gave me that conference room. And then right away he says, oh yeah, I could believe it. I could sell anything, right?
- [13:18]
Cass Lazzaro
Well, it's true.
- [13:19]
Mike Lazzaro
So it's basically my whole life is listening to my gut. And I wouldn't recommend it to everyone, but I do stuff that I think should exist in the world. Or, you know, liquid death is a great example. Like first time Peter Pham at Science talked to me about it, I just went down a rabbit hole. I met the founder, Mike Cesario, and on the spot I said, I'm in. This is pre launch an idea on a napkin. And I just thought that a wellness product marketed really well using content that made people laugh was like, would find a place in the world. Now did I think it would be as big as it's gotten? Of course not. You never do. And so where I get in trouble is when I don't listen to my gut. And I just happened the other day where I'm like, ah, I knew this, shouldn't have done this. I should have just listened to my gut. Literally. I've never said, don't listen to your gut again, or I shouldn't have listened to my gut. It's always, I should have listened. Right? And so I think that's what that story is about is like, you have moments in your life, if you make the right decision, it spirals in a new direction. If not, whatever. Life goes on. And I'm not afraid to do stuff that other people think is crazy, including my wife.
- [14:42]
Cass Lazzaro
There's another point to that though, which is another myth for entrepreneurs, is that they think that the first idea they have is going to be the one that actually makes them big, right? So they think that they'll never have to pivot, they'll never have to change anything, and that whatever they came up with the first time, to the investors, to their company, to their employees, to their parents and their significant other, is the thing that's going to work. And we argue 95, 98% of the time that's not true. You're going to have to pivot and you're going to have to let go of your ego around that original idea and really that original story that you pitched and got so good at pitching and eat your pride and say, wait, this isn't working. Here's how I know it's not working. And we're going to change it by going over here and those entrepreneurs that can can basically say, okay, I accept that whatever this idea is is not going to be my last iteration. Those are the ones who succeed.
- [15:48]
Chris Do
Since you just mentioned this, Cas, I think you two are kind of like the embodiment of, like, how creativity should exist. And when I speak to mostly creative people, the problem is in the creation process. They're judging at the same time. And you have in two human bodies where Mike throws ideas out over the fence, as you say, and you just have to worry it's going to work. He just has the freedom to play, to run naked with scissors and crayons and whatever he wants to do. And then you get to say, like, oh, of the ideas that you came up with, these are things I can see as doing. And then you can judge. And so what we want to do is just put some space between those two. If it's just you. The second thing you said just right now was, and I just want to draw that to everyone's attention is you have to have faith that you have more than one good idea. People are stuck because it's like, I think it was mostly because they're scared. Like, I got this one idea. I don't know if something else will come. And maybe for some, that is literally what happens. But what I'm hearing from you is you have to have faith to say, like, you know what? This ain't it. This ain't it. I know you spent the last five years trying to build this thing. It's not it. You have to pivot. You have to find a new thing. And to know that back there inside your brain, another idea will come if you allow it to step out, right?
- [16:59]
Cass Lazzaro
If you let go of that ego, that pride, and that autopilot like, this is the idea, and this is what I pitched everybody on, and this is what I'm known for. Maybe even becomes part of your identity. If you can let go of that, then you can actually get out of your own way and start really looking at the factors that you can judge against, which actually, this is how you created your whole pitch. Like, you can go back to your projections and say, oh, well, of course this isn't working because we have no clients or because we didn't hit this milestone. And you can be objective and actually make some changes for the good before you run out of money.
- [17:39]
Chris Do
But what do you say to people who are like, but it hurts. If my idea fails, my business fails, I'm a failure.
- [17:46]
Cass Lazzaro
It does hurt. There's no way around that. There's nothing that I can say to make people say, like, when this idea didn't work and I didn't listen to my gut and I didn't cut half my staff to stay alive, and now I'm out of business, I feel like a failure. Well, this too will pass. Okay, so out of failure comes some of the greatest ideas, some of the greatest strength that you can have if you choose to listen to it and look at it objectively.
- [18:15]
Chris Do
A habit that my team sometimes get caught up in, which is they fall in love with the input and they're not really looking at the output. So we spent five years building this, and we're doing everything we can. I've sacrificed so much. But the results are, we're losing customers, not getting traction. We're not hitting our numbers. How do we get past that attachment to. Well, we're doing what we're supposed to be doing and not looking at the result.
- [18:40]
Mike Lazzaro
I think that a lot of it is because we've spent a lot of time studying that, and a lot of it's leadership. And we write about this in the book the Death and the Pivot, where we compare pivoting a company to kind of leading a skydiving exercise where you don't quite know if the parachute on your back is going to open, you don't know how far you are away from the ground. You have very little information, and you basically have to get people to jump. Not without fear, because it's scary. And if you say, oh, don't be scared, say, well, that's an emotion that I'm feeling. I can't not feel that way. You have to get your organization to move despite the fear inside that fear. And Buddy Media, we pivoted three times to get to our business model. Cas approved these ideas, but we had something called Ace Bucks, which was literally the worst idea I've probably ever had.
- [19:36]
Cass Lazzaro
Which was, I did not approve that. I want to make sure we're clear on that.
- [19:39]
Mike Lazzaro
You didn't veto it. Let's just say that, like, revisionist history here. Like, come on.
- [19:44]
Cass Lazzaro
I just had our third child. Wait a second third child? You came up with this idea while I had just given birth, literally after the C section.
- [19:53]
Mike Lazzaro
Sometimes you got to, like, just, you know, you got to suck it up stuff when people are down and out.
- [19:58]
Cass Lazzaro
When the iron's hot, he's like, she's down and out. Let's do it.
- [20:03]
Chris Do
And you're weak right now.
- [20:04]
Mike Lazzaro
But we kind of, like, we looked at the results, which was like, oh, no one wanted this, like, a Spock stuff. And eventually we talked to enough customers that they said, you know, Sonny, we don't really love what you're doing, but we need help on Facebook and Twitter and the other early social networks. And that's where our first our Facebook page management system product came, and then our whole social media management system came from. And your job as a leader is to pull off the band aid, set the course, make sure that everyone has what they need, and. And oftentimes lay people off and reorganize the business. And you can't expect your people, who basically are getting a salary, not all of them are risk takers like you. You can't expect them to get there on the own. You have to lead, and leaders lead, and leaders win, and they continue to play even if they're down in the second half and need to come back.
- [21:01]
Cass Lazzaro
It reminds me of another myth, because you talked about this myth theme, that the best leaders are totally transparent. And I know you've heard that before, and it's like buzzword of a century, but it's about always telling your employees and your team the good, the bad, and the ugly. It's making your employees no different than your board or your investors and telling them, we hit these numbers, or we're having a tough time over here. We were so transparent that during our three pivots, we didn't lose anyone. And if you can do that, if you can lead with a huge amount of transparency, even talking, like, we shared financials, like, how were we doing? Did we hit numbers? Then people don't leave because they're so loyal, because you're telling them the truth. And Mike always says this. People are okay with bad news. They're just not okay with surprises. So You've got to get rid of this myth that you can't tell employees the bad stuff. You can, and you have to.
- [22:09]
Chris Do
That reminds me of something that my business coach told me many years ago. Absent an explanation, people create their own narrative. So in good times and bad times. So everybody assumes you're making money. And then when you have to cut people back, they're like, wait, why'd you get rid of xyz? We're doing great. Or they see, like, oh, we just signed an ex client, and. And they don't understand only a certain percentage that is profitable, if it's profitable at all. So we as leaders, as managers, as visionaries, need to bring our team in and to let go of this idea that we have to hold all the information because the team is going to be irresponsible with that information. Right. Transparent leadership. I'm a big fan of. Okay, I got to ask you this question here, because there's this idea that you said about trusting your gut and not listening to your gut, but you didn't give us the example, Mike. When did you not listen to your gut? And how did it turn out?
- [23:01]
Mike Lazzaro
I mean, I'll tell you one story that I really haven't talked about because it's painful. I mean, to me, it's. You know, it's one of my biggest failures, which is I was a little lost after we sold Buddy Media, and I spent four years at Salesforce, which I wasn't lost. I was great. Salesforce, an incredible company, incredible customers. I was doing some of the best work of my life. But then I was just tired. I have a artificial heart valve and some health issues. I just told Mark Benioff that I just have to focus on my health. I was 40 pounds more. Cass and I were fighting. I didn't know my kids. I was just looking forward. And I was like, man, this is not how I want to go. Right? God forbid anything happened. It's just not a life worth living. Because for entrepreneurs, it's not about money. Like, we started off just. You don't start off on the Internet in 1994 because of the money. There's 13 million people on the Internet, right? We just are creative. We like doing stuff. And so I got a painting studio. I paint. It's a hobby. I'm not very good at it, I realized. And then I was hanging out with an artist friend who was giving me advice on painting. And a big artist, I mean, sells stuff for, you know, sold pieces for a million dollars more. And he had a good Idea for technology. And I started a business with him and it's called Shape Matrix and it's still around. Very sweet guy. Jonathan Kramer is the artist and I help raise money. We raised $12 million. It's a new visual language based on the eight basic shapes that populate the world. 3D shapes. And there's applications for cryptography and security and tag and track. But in my gut, I was like, man, he's an artist. Sweet guy. Never done a business. I don't have cast. Who's going to operate this? But I was just not in a great place personally. I'm just like, this is my passion. I'm going to do it because it's creative, it's art, it's business, it's cool.
- [25:03]
Cass Lazzaro
And also, you had talked to me about it.
- [25:05]
Mike Lazzaro
Yeah. And Cas is like, I don't know. But, you know, I support you because she was burned out in her own right. Right. Because she.
- [25:13]
Cass Lazzaro
I just said that the picking of this partnership didn't seem to be a perfect fit. Right. Like, you want co founders to have the same kind of vision. Let's call it that.
- [25:27]
Mike Lazzaro
And so I'm still on the board of the business. I had to, like, I just couldn't. Co founders relationships are very hard and we couldn't work together, you know, which is why I'll never do anything with anyone other than Cass. And if I do, please punch me in the face, someone and stop me.
- [25:42]
Cass Lazzaro
It's okay. I have a little shock machine on you.
- [25:46]
Mike Lazzaro
And so that was like. It was so obvious in my gut that I shouldn't do it, but I was so filled with kind of identity crisis, really hubris. I think it was more of like, you know, oh, I can make this happen. Right. I've sold this. Because when you make all this money, people treat you like you're smart. And it's like, I'm the same old schmuck that I went to journalism school and I've always been. And it's just been a really painful experience which has resulted in. We've lost money. Investors haven't seen a return. I mean, it's still kind of around, but if anyone is interested in a visual language to help secure the supply chain or cryptography, please give me a call. I'm not. But it's, you know, I'm an eternal optimist and I don't give up. The other thing is, like, we have a hundred investments we've done, and when we put in money, when we commit to being part of the team, we Never give up, no matter how good, how bad. Like, we're in it. And it's been like that one gut decision that was so obvious. My gut saying, don't do it, don't do it, don't do it. I basically. I mean, the thing is. And what I've realized is, like, your gut is usually right, and then you spend two weeks talking yourself out of your gut. It's like this internal, like, well, like, my gut's not thinking about this or that or, like, you know, I don't think that's going to be an issue. And like, at this point, I'm like, that first reaction that I have, write it down. And that's the truth.
- [27:19]
Chris Do
You weren't in a good place, mentally, maybe burnt out. And then you have this hubris of, like, I can make anything great. And there's this super great artists that you're collaborating with. Maybe you admire this person for their.
- [27:29]
Mike Lazzaro
Work and, like, who's a great friend, like, right, this is gonna work.
- [27:32]
Chris Do
Of course it's gonna work. And you raise all this money and you do it. And Cass is like, I don't know about this one. And your gut's like, I don't know either, Mike. But you're like, no, no, shh. I just want to make sure we're talking about the same thing here. So oftentimes we refer to it as the gut. I think, if I remember correctly, Simon Sinek's whole thing, it's like the limbic brain, the decision center, the emotional part that makes all of our decisions. I think that's what we refer to as the gut. And it's the neocortex, the logic part, that then talks our limbic brain out of it to say, you know what? Screw you. You know what you're talking about, and we're going to do other thing instead. Now, sometimes I think we mix those two up where we think it's our gut telling us we can do this and forget about the worries and the logic part, but it's the opposite. Have you been able to figure out when you know which is the gut or the limbic versus the neocortex or whatever?
- [28:22]
Mike Lazzaro
We love this topic, and it's both magic and art and science. And I've been able to tune into a feeling, and I've talked to a lot of people about this, and I know that feeling because it's a subconscious processing of data. It's not just a gut. If you're running a business, you have to make a big decision. You have years worth of data and results and conversations and third party data. And it's just like in there, right? And you have to let that process play out and result in a feeling. And that is the feeling that I've tapped into, which I call my gut. I'm not as smart as you, and I'm definitely not as smart as Simon Sinek, who I met very early on. And I was always like, man, this guy's going places. But what you say resonates because it's a very kind of like our brains and the computer systems that we have in our bodies are. They're just amazing. And they're doing the hard work to result in one output that I now, through a lot of trial and error, can recognize.
- [29:32]
Chris Do
I'm going to get to Cass, but there's this line I think of, I can't remember exactly, and it's like Benedict Cumberbatch's run on Sherlock. And he was saying something to Watson. I just have to listen to my instinct. And Watson turns to him like, wait, instinct? He goes, no, it's just your brain working faster than your logical brain can comprehend. And that's what you're speaking about, Mike. We have all this experience in this data and it processes so fast that we just call it gut or a feeling, but it's actually super logical too. And there's something that's beautiful about your brain, that you're a dreamer. And dreamers, visionaries are also romantics. Everything works in your brain, your brain and your mind. Whereas Cass, I think you're a lot more like my wife. You're like the realist. My foot's on the ground. Some of your crazy hair brain ideas just don't work. How does your gut serve you?
- [30:21]
Cass Lazzaro
I was thinking about this when Mike was answering his question. So I've always looked at pathways. How do we move pieces up a chessboard, knowing we're going to make sacrifices down the line, right? So we're going to lose a couple pawns, we might lose our rook. Like, we've got to do some things that push the board forward, even if they're not perfect decisions. And I've always loved, you know, what do they teach you in, like, Economics 101? You've got to make imperfect decisions with imperfect data. And the people that can lead in that kind of uncertainty are great. But for me, when I think about it, if something I can't see a path, what looks like to me in my brain is I can't see a path that can move enough of our pieces forward Then it keeps me up at night and I keep trying to say it won't settle. I always tell Mike, like, okay, I think I'm settled on that. That feels right because I'm not trying to go find a different way to solve it. So for me, when my brain quiets down, I know that my gut, whatever you want to call it, is okay. And I think it's a different way of seeing things than Mike. And I think mine is very hardcore and very tactical and sharp, if you will. Because I'm kind of saying, like, okay, he's got this idea, this is what he wants me to do with it. And then I'll go like, it's like a board on the, in my head, like on my super screen of my brain looking at all the different things that that could be impacted. And if this is worth it, I.
- [31:53]
Chris Do
Want to go down that path a little bit more with you because my wife, who's also my partner in business and life, and the mother of our children, we see things a little bit differently. And I'd love to get your perspective on this, Cas. So I'm okay with risk. I'm very risk tolerant and she's very risk avoidant. So when there's an opportunity. An opportunity, we'll put that in air quotes because they're not opportunities. Half of the time I'm totally wrong. I don't know what the next move is, but my gut says this is going to work out. So I'll do business or I'll go to meetings and I'll do things with people that I'm like, it may not work out. Whereas my wife needs to see what the next five steps are on that chessboard because she can't see the play. She goes, why are we wasting our time now? More often than not, I would say like 80% of the times I'm right about this kind of stuff. I'll put myself in a risky quote unquote way, but then they pan out to be this other opportunity I could not have seen. So from your perspective, how do you process that where I don't know what the next moves are and do I allow ourselves, our company, Mike or myself to go forward not knowing, or do I shut it down?
- [32:57]
Cass Lazzaro
Maybe this might be where your wife and I are different. I'm a risk taker. I think that in order to succeed with anything, you have to be a risk taker and be okay with whatever the consequences are. Because if you bet on yourself, you can pivot into something else, good or bad, whatever that may be so with things that Mike comes up with, like Ace Bucks or tickets. He had this one idea with tickets, which was just wanted to make me vomit.
- [33:24]
Mike Lazzaro
Free felt. Freefelt.com Don't.
- [33:26]
Cass Lazzaro
Don't even say that one yet. I'll tell them that one in a second, but made me want to vomit. In our company, I'm willing to not know how to execute as long as I can still see a path forward with the team members around me. It's when there's like, how does this work with the team? Like, this doesn't. Like, I can't see the workflow. I can see this getting to be a big bottleneck. This can't scale. And nothing makes me more itchy or upset or grumpy than not being able to scale something in an efficient way. I can stand in a line at a movie theater and I want to go up to them and be like, you know, if you just put the rails over here, it's just going to go a lot faster. So that's how I process it. But it's not about risk for me. I never look at it with a lens of risk. I look at it as, how can we move forward and not disrupt the board?
- [34:23]
Chris Do
And it's a very rare thing that you possess. And probably why Mike's like, I can't do this with anybody else except for with Cas, because a lot of people ask the how question, but it's not the same how question. Like, he has a big idea, and most people are like, well, how's that going to happen? So we're kind of caught in the tyranny of the how. We get caught up in the weeds, and you're just like, no, we like this idea. How do we make that successful? Not how do we deal with all the details, Right? So it's very different. Your mind is activating something.
- [34:51]
Cass Lazzaro
Yeah, it's activating this. Like, go forward. Just move forward. And I think I'm able to say, okay, these are the three markers, if you will, if they happen, we got to shut this down and pivot. So to me, it's about. I guess if you really kind of boil it down, it's about data, right? So I'm willing to take any idea and I'll figure out how to move it forward. But if we're going to measure ourself against scale, efficiency, making money, you name it, that's great. Give me those data points because that just helps me with my equation. Now I will tell you a story that you will laugh at. So we had just had our second child, Cole, and we had him on April 4, 2004. So 040404, which is kind of a lucky day. And we were limping along with golf.com because the ad space was coming around, and we had been living through the dot com crash. And one day, I have two small kids. We work in the basement in this tiny room. The doorbell rings, and this guy with this huge truck says, hi, ma'am, We've got your felt. And I say, pardon me. And I have the baby on me. And he's like, we have your felt. And I said, I'm so sorry. You must be in the wrong place. They're like, no, no, no. Michael Lazzaro. And I'm like, yeah. And he's like, we have your felt. And I'm like, why do you keep saying felt? Like, what does felt stand for? And he's like, felt, felt poker, Felt, felt for tables. And I said, well, how much felt do you have? And I walk to the truck, and there's like, four pallets of felt. So I go, hold on a second. Slam the door, Go back down. I go, mike, what the f did you just do? He's like, oh, well, I might have started a company called Freefelt.com a couple months ago. And I was like, what? He's like, yeah, I ordered all the felt. Poker's really big, and we're just going to start sending the felt out?
- [36:53]
Mike Lazzaro
No, there was a business behind it. It wasn't just sending it out. It was a lead gen system for online poker sites.
- [37:01]
Chris Do
Wait, wait, Mike, I need to hear the rest of the story, and then you can tell your side of it.
- [37:05]
Cass Lazzaro
Honestly, there was no connection on what made sense and why in my home, there was going to be four pallets of felt. And then ready. The big question, who was going to be sending the felt? Who? All right, Mike, you can now say it.
- [37:23]
Mike Lazzaro
It was a mistake. I was young, so I'm not going to.
- [37:27]
Chris Do
You can say that now. You can say that now.
- [37:29]
Mike Lazzaro
Hindsight, the idea was simple, which is like, this is the beginning of online poker sites are getting paying out a thousand dollars per funded account. So, hey, you're playing in an online poker game or a home poker game. Here's like, free felt. Just pay shipping and handling. I'd break even off that, but I'd be able to get people to raise their hand and say, I play poker. And then get them onto poker stars and all these sites. Now, let's just say at the time when I was only 30 years old. Not even 30. No, I was about 30. I wasn't great at what's called communication and asking cast questions that I didn't really know the answer to or you.
- [38:11]
Cass Lazzaro
Didn'T want to hear the answer?
- [38:12]
Mike Lazzaro
Yeah. So, like, I wouldn't ask her if I knew. No, I kind of knew you'd hate the idea.
- [38:16]
Chris Do
So I resemble that statement. I'm going to say.
- [38:18]
Mike Lazzaro
So I'm like, if I ask her about this business, she's going to say, no, I'm not going to be able to do it. And like a giant man baby, I just went and did it. Now I've grown through therapy, through like just my self awareness journey to realize it's better to have the tough conversations. So a lot of my conversations with Cass go like this. Are you seated?
- [38:39]
Cass Lazzaro
Are you sitting?
- [38:40]
Mike Lazzaro
You're going to like nothing about what I'm about to say. All I ask is that you listen to it without interrupting. And then I will say, Fish is playing the sphere in Las Vegas. I know. I just got back from Fish Mexico. I would like to go and celebrate my birthday with my guy friends. It would mean a lot to me. And she says yes or no, and if it's no, I won't do it. But most times she's like, yeah, I get it. In the past, I would, let's just say, not be as direct. And I think this is good for business and not just personal relationships. I try to like maneuver her or not be upfront or lies of omission or pitch it. And so it's much better, I've learned really in business but also in life to just say, just ask for what you want and acknowledge that the other person may have experiences and experience it in a way that's not great for them and sit with their feelings as well. And you know you're not gonna get everything you want. But that's been a big part of our relationship because there's not only we work together, we have kids together, we're always together. But I like doing stuff that she doesn't like doing. And so there's a me in addition to the we. And that's really healthy in any relationship, especially a co founder relationship where you need to blow off the stink. It's a really hard relationship, no matter if you're married like our two couples or not.
- [40:11]
Rich Cardona
It's time for a quick break, but we'll be right back.
- [40:23]
Chris Do
Enjoying the conversation you're listening to right now. You're going to love what we have for you inside the Future Pro membership. From live group calls with myself and vetted guest Experts to over 600 hours of pro exclusive trainings and monthly, monthly networking, you'll have everything you need to fast track your growth. Check it out@future.com Pro.
- [40:45]
Rich Cardona
And Rebecc, welcome back to our conversation.
- [40:50]
Chris Do
Well, first of all, it sounds like you've done some therapy and it's working because the words you say sound a lot like what a therapist told you to say and you're a good student.
- [41:01]
Mike Lazzaro
Yeah, no, I've like worked on that because I was not self aware. I was an idiot like most guys.
- [41:05]
Chris Do
Now I'm going to ask this question and it's self incriminating and it might lead to all kinds of trouble here. When you say as a man, baby, there's something that you want to do and you know it's not going to hit. Well, first of all, I want to point out I notice a pattern every time. Cass, you're pregnant, about to deliver a child. He's doing all kinds of crazy stuff. He's like, you're not available. I'm going to do stuff.
- [41:27]
Mike Lazzaro
I never knew that, but I actually had thought about that. As we're talking, I'm like, maybe I shouldn't have done this.
- [41:32]
Chris Do
I can see that now. There's a pattern.
- [41:34]
Cass Lazzaro
It's a pattern. Yeah.
- [41:35]
Chris Do
But anyways, getting back to the question here. Okay, so I have this theory, Mike, let's just pretend cast is not right here and my wife can't hear this episode. I'm just going to say it as a man. I don't feel like I'm signing up for like a parent. I'm signing up with a partner and I should be able to make decisions on my own without having to get it approved. As I respect the wishes of my partner. She can do whatever she wants. She don't need to approve get anything approved by me. She's like, I want to go out with the girls. I'm going to spend three days in a desert. I'm like, cool you do you like Kevin Hart? You do you? I'm good. Now there's this whole thing about like just my own identity and self worth. Like why am I asking for permission to do things that I don't have to ask permission to do? So you're like, I want to start this crazy business that with felt or I want to go to fish and do another concert. And the way I would have handled this in the past and hopefully I'm better today is I bought the tickets already. I already told My friends, I can go. I'm delaying having the conversation with my partner, Cas. And I'm trying to figure out how to bring it up to her, which negates her ability to give input, which is robbing her of her power and maybe her worth in the relationship. But this is the crap that men do. I'd love for you to speak to that, if that sounds remotely true to how you feel. And then I want Cass to just rain fire on us.
- [42:58]
Mike Lazzaro
No. So what you described was like me for basically the first 10 years of our relationship.
- [43:05]
Chris Do
Fifteen, give or take.
- [43:08]
Mike Lazzaro
No, Maybe more. Maybe more. But what I realized is that it's okay to want to do stuff and to just do it, but when you have a partner who you respect and love and want to care for, horror. Some of the actions actually impact her negatively. So it's not just that you're going to do things. It's. She's working as hard as I am. We're both trying to parent, but she's doing probably 90% of it, and I'm doing 10 because I don't know where the dentist is. I have no idea how to get them dressed. I don't know what vaccines are, like, all that stuff. And so when I disappear for five days, like I will next week, going to Mexico for fish. Mexico, it means she has to do everything with the kids. And so all of a sudden, my needs have spilled toxic waste onto her mental wellness, let's just say that. And so you do that enough if you value a relationship and it's worth working on. You have the hard discussions. And if she really. She has not said no to many things, but if she really does not want it to happen because it is tough for her, for whatever reason, I respect that and I don't continue to sell it anymore.
- [44:32]
Cass Lazzaro
I think the only time I've said no was we were giving birth to Cole. We were in the doctor's office, and we had just moved. I was 36 weeks pregnant and flu, probably really stupid to move. And we were moving all of our furniture into this new house and everything. And I had to meet a new ob. And the OB says, okay, well, we should plan a C section since you've had a first C section. I was like, well, I really don't want to do that, but okay. And he throws out a date. And Mike goes, I'm kind of going to SNL that weekend. And I shot him a look like, are you fucking kidding me? Like, what? And that was the old mic. So I love everything that you both said, I actually was thinking when you were talking that, like, Chris, like, you've done so much work because you are identifying exactly what Mike and I have identified for so long. And it's that mental load. So I always talk about it as a partner and wife that there is and a mom, that there's a mental load. And us moms tend to take. Not always, but tend to take on the big mental load of details and operations of everything in the family. They might even take on financials, right? Finances in the company, social plans, which I never do, thank God, and stuff at schools, which not my forte either, but I do it. And so I think Mike was right that just acknowledging that there will be a higher mental load on you because I'm going to do my own stuff is the first step. Now, Mike says the same thing. You go do whatever you want. Go do whatever you want. And I think us moms, us wives, will then get everything ready perfectly for when we leave. And the reason is we don't want you to have that mental load on you. We want it to be less disruptive. You guys are kind of thinking, I don't care if it's disruptive. You're not literally saying, I don't care. It's just that you're not thinking about it that way.
- [46:36]
Chris Do
I think there's a lot of truth in this conversation. It turned out to be like couples therapy, some self healing. It's a little bit different, but it's.
- [46:43]
Mike Lazzaro
Not that different than, I mean, the reason why I'm talking about it. I normally wouldn't in this, you know, a. I would with you. I mean, you're creative, you're an empathetic guy. Like, I know kind of what you believe, but it's the same stuff in business. You are who you are. And so, like, if you have either either a partnership or a co founder, have the tough conversations, acknowledge that your actions may cause more stress, pain, get it out there. Because if you have a partnership, it's not like, I'll cover you this time. I know you got me. We're here for each other. If this is important to you, I got it. And on the home front, I have a small kind of N equals probably, I don't know, 20. But like, it's harder for moms to turn it off. It's harder for Cass and her friends to just disappear. Let's just say it's not hard for me. And once I'm gone, I'm gone. And I am in a different head space.
- [47:43]
Cass Lazzaro
We call him Chris. I actually have a name for him. It's called Vacation Mike.
- [47:46]
Mike Lazzaro
And I need it. It's a part of who I am. It's part of the creative process. You know, I do a lot of music festivals, and I have a whole crew that we talk about business and innovation at the festivals.
- [47:58]
Cass Lazzaro
But, Mike, don't you also think it's how you operated as an entrepreneur and a leader and a founder, too? Like, one of the things we've always seen with entrepreneurs is they can get burned out very quickly. They can struggle with mental health because it's lonely, quote, unquote, at the top. So you definitely have to figure out how you each individually fill your cup. And hopefully you've picked a partner just like the four of us have that compliment your skills. So there's no overlap, which means there's no paralysis of decisions. There's no micromanaging of each other, and you can actually trust each other implicitly and say what you mean and mean what you say and get things done.
- [48:41]
Chris Do
I'm going to say this. Maybe half of myself and maybe Mike and all the other men out there. I think men can be fairly irresponsible and carefree. It's probably why some men leave their partners and their children behind and why it's much harder for a woman to do that. And there's something about that I don't fully understand or pretend to. And then women are left with the burden of taking care of things that we don't look at because we just don't care enough. And I don't know why there's this need to make sure all the boxes are checked and everybody's got what they need, because oftentimes I find things always work out. But maybe that's just through my irresponsible lens.
- [49:18]
Cass Lazzaro
It's the same thing when the kids are like, oh, my God, the holidays are so amazing. I'm like, I'm Santa Claus. Right?
- [49:26]
Chris Do
Wait, wait. If you have children, this is the part where you don't send the children off while you listen to this part.
- [49:32]
Cass Lazzaro
But, like, you know, when they got older, they would kind of do this. Even my daughter would look. Look around and be like. And I'm like, no, no, no. Right over here. Like, I'm the one. This is just amazing.
- [49:43]
Mike Lazzaro
And they're. I mean, okay, the crazy things that they're Jewish. They didn't even know Santa Claus was.
- [49:50]
Chris Do
Okay, I'm gonna say this part, and maybe there's some vengeance in here for all the women who are dealing with this nonsense. I Recently traveled with my boys. It's just a boys trip. We went to Japan. I was gone for almost a month. They didn't stay for the whole trip. And every once in a while, I check in with my wife, and she's like, how's it going? She stayed home. She needed her own meditation break, right? And I'm like, it's fine. They're really responsible. They're doing stuff, and we just go with the wind. Today we go here, tomorrow we go somewhere else. And I have no idea what the plan is, and I don't even care. And I said, they're not complaining about anything at all, and we're just getting stuff done. Not everything has worked out, but that's okay by me, too. We'll go to a restaurant, sold out or can't get in another one didn't work. We figure it out. And she goes, you know what? I guess that's just the mom's role to receive all the complaints.
- [50:38]
Cass Lazzaro
Well, that's the other part.
- [50:40]
Chris Do
You know, when she plans everything, oh, we don't like this. And the hotel is too far, and why is this train here? And it's like, nonstop. And I said to her, honey, kind of like, you open yourself up to hear the complaints. Because when they complain to me, I'm like, who planned this? We will adapt. We'll improvise, and we'll overcome. We in the spirit of the moment. And we might be cold, we might be hungry. And we were both of those, but we survived.
- [51:05]
Cass Lazzaro
I love it. I love that. How old are your kids during this trip?
- [51:09]
Chris Do
This is just a couple of weeks ago. They're 21 and 18.
- [51:13]
Cass Lazzaro
I love it. We are the receptacle of every complaint. All moms are, because it's a safe place to project your uncomfortableness, your insecurities, your complaints. You name it, it just all comes out. It's the famous, you know, when are we going to get there? Or when's the food going to come? Why are you looking at me? I always say, look at your dad. There's another adult here. You can ask him those questions, too.
- [51:38]
Chris Do
Well, there's this thing where my wife actually polls them for their opinion about where to eat. And she's constantly, like, in the matrix of her mind. This person likes this, this person like that. And it's like it makes my head explode. I just say, we're eating here, naturally. Nobody has a choice. And if you want to go buy your own food, go. I'm happy. I'll just eat by myself.
- [51:56]
Cass Lazzaro
We changed that very Quickly because of just operational. I actually remember the day that I walked out after Salesforce bought us and I was not let go. But like, I didn't have to work there for my earn out anymore. I remember coming back home and saying to Mike, I'm done cooking. I'm done going to the grocery store. I don't care if we ever go do anything. I'm not doing it anymore. You can do it. You can do it now. Because I've done it for the last, I don't know, 10 years with all of us, 15 with both of us. And he looked at me a little confused and then it's like, okay. And now Mike's an incredible chef. He's great. He's incredible. Which is amazing.
- [52:41]
Mike Lazzaro
I do it for selfish reasons.
- [52:43]
Cass Lazzaro
It's like, well, you like it?
- [52:45]
Mike Lazzaro
I mean, it's 45 minutes out of the day where I can put on my music, listen to podcasts, tune out the world and not be judged.
- [52:55]
Cass Lazzaro
And it's creative because I'm going to.
- [52:56]
Mike Lazzaro
Provide an epic meal that I want.
- [52:59]
Cass Lazzaro
To eat with 30 pans. Sorry, I had to say that.
- [53:02]
Mike Lazzaro
Yeah, I make a mess. I do make a mess. But like, I'm not doing it in service of others. I'm doing it because I love doing, doing it. And I think if you're doing things for other people that you hate doing, don't do them. That's not giving. Right. And I like controlling the food because Cass is Italian and she could eat piles of pasta and never gain weight. I have one bite of pasta and I have love handles for 13 years. And so controlling the food let me eat the way I wanted to eat. But my daughter doesn't eat meat, so I kind of still make it work. I'm not a. You're shoving hot dogs down her throat, saying it's either this or nothing. But I think partnership in life, in business, how you treat people, and it's not even how you treat people, it's how do you make people feel. People aren't going to remember what you did for them or what you did, but they're saying, yeah, that person made me feel blank. Right.
- [54:04]
Cass Lazzaro
Seen or listened to? Comforted.
- [54:07]
Mike Lazzaro
Yeah, you know, comforted, fired up, excited. And I think that's a lot of what the time I spend with people is basically like, where are they and how can I get them to a better place just by leaving them with something. And when you work with entrepreneurs, we have a hundred investments, private investments. We own, we own some companies and we give a lot of therapy and it's basically, if they leave us dejected, we have totally failed in our job as a partner.
- [54:41]
Chris Do
Okay, I want to get to the book, but before I do, I want to share a little something I've learned in therapy. Whether you identify as male, female, however you identify, if you're the person as the designated caretaker because it's a role you volunteered for or one that you were forced into, there's something I've learned, and my wife is still learning. And whenever somebody says something, blah, blah, in the household, ask yourself, was a request made of me? So when somebody says, I'm hungry, well, no one was talking to me, then you don't need to respond. And then if it's a mom, I'm hungry, was that a request? No, just a statement, a feeling. So, mom, I'm hungry. Can you make some food? Then the next question you ask yourself is, is this something I can do? So if they're like, mom, I want to go to the moon. Can you help me build a rocket ship? Then you say, no. And then lastly, if you can do it and a request was being made of you, then you ask yourself, how do I want to respond? Because the default answer isn't yes. And we have to slow down the springing to action. I see this happen all the time. I look at her and I raise my hand like, what are you doing? What are you doing? I mouthed it to her because somebody's like, oh, I'm so hungry. She's like, I'll go make food right now. I'm like, babe, that's not your problem right now. And this is in real life and as it is in work, because somebody has purchased something, and now all of a sudden, you have to deal with inventory, and then you have to deal with fulfillment. Gas felt.
- [56:10]
Cass Lazzaro
It's enablement in a way, right? Yes.
- [56:13]
Chris Do
Yes, it is. And we have to protect ourselves.
- [56:16]
Cass Lazzaro
Yes. We also have to think about. If you think about being in a company, I mean, it's funny you say all this, because I always thought that I could take everything I learned by being a leader in a company and bring it back home. But I still can't figure out a way to put my kids on a pip and have them want to improve. But at the same time, what you have to look at, which is very similar, I think, is how do you want them to act and what are you contributing to make them ask those questions? I'm hungry. That's like saying, I want to be 5 foot 10. Those are just statements. And what do you want to Teach them in your response. That's the hard part. That's why parenting, I think, is much harder than anything else that anyone ever does. Parenting is way harder than work because it's a constant teaching with no leverage of firing.
- [57:08]
Chris Do
Well, I put into the. My children, when they're much younger, the possible threat of firing when they didn't know better. Like, would you really leave us here? I'm like, test me, test me. We'll see.
- [57:20]
Cass Lazzaro
Of course.
- [57:21]
Chris Do
Right? Of course. They never call the bluff. Thank God, because I don't know what I do. And only as adults can we talk about, what would you have done? And then I told them the real strategy. But, you know, here's the thing we can learn. If you want to raise great, independent, autonomous children who have the values and the ethic that you want, then you need to raise them a certain way. And if you want employees with the exact same mindset, you have to handle in a similar way. And you're. And something I've learned too. You learn things about parenting and relationships. Well, what is a work relationship? Is a relationship exactly.
- [57:51]
Cass Lazzaro
It is. It's another family.
- [57:53]
Chris Do
Yes. And what you don't want to do is you don't want to infantilize your children. You don't want to infantilize your partners, your co founders, and your employees. Same problem. Like trying to do everything for them.
- [58:04]
Cass Lazzaro
You want to empower, and it creates competency. Competency, which is a big thing.
- [58:10]
Chris Do
Okay, I want to get to the book. I know we don't have a ton of time. I'm excited for you guys. The book launches, I think, in June. It's called. I can't even say because I don't swear, but I know.
- [58:19]
Mike Lazzaro
Shoveling shit. A love story.
- [58:23]
Chris Do
Thank you, Mike, for doing that.
- [58:24]
Mike Lazzaro
Chris is a much. Has a much cleaner kind of language than me. We do.
- [58:29]
Cass Lazzaro
It's about the entrepreneur's messy path to success. So we love it. We hope that entrepreneurs want to pick it up because we have, like 50 plus cheat codes in there. 30 years of our lives and lessons that we've learned and really just trying to give back to everybody so that they can get a head start when they decide to become an entrepreneur.
- [58:50]
Chris Do
Okay, now, there are parallels here, right? It's a love story, your own love story and how you're able to make this work. And it's obvious here, there's give and take, push and pull, but there's also the love story about, like, loving your business, doing the hard work. There's a lot in there that you. If you are not made for it and you can't learn to love it. You're going to going to ultimately not be as successful as you want. In worst case scenario, you fail. So I get that part. And you mentioned cheat codes, so let's just do this. With the time remaining, why don't we just go left and right, left and right until we are, like, tired. Give us one of the cheat codes, let's go to Mike, and then we'll bounce over to Castle and just go back and forth. Okay, what is one cheat code, Mike?
- [59:27]
Mike Lazzaro
I mean, number one is to me is don't run out of money. Three things that a founder has to do is not run out of cash, not run out of cash, not run out of cash. And we talk about the greatest ways to fund the business, not venture businesses. This isn't built for tech entrepreneurs. It's built for the 5 million people who start businesses every year. Most of them look like restaurants and literally laundromats and service companies. And the number one way to really bootstrap your business is customers. And we focus a lot on that. So that's like number one cheat code for all entrepreneurs is how we got very good at funding businesses, both through customers, and then obviously at Buddy Media, we had to build stuff before we sold it, so we'd end up raising a hundred million dollars.
- [60:15]
Chris Do
Wonderful. Okay, over to you, Cas.
- [60:18]
Cass Lazzaro
Focus, focus, focus. So zero to one, you're starting a company. You know what you want. You've pitched your idea to friends, family, investors, whomever, and you create that financial projection, what it's going to take, what it's going to look like in terms of expenses and revenue. So your job in that first year is to constantly, and this is what we see entrepreneurs not doing, but constantly look back at that financial projection so that, that becomes your focus. That's how you measure yourself against what you told everyone that was gonna happen. That was good. That was a good outcome in the first year. What you tell investors, what you tell friend and family, what you tell seed money, whatever it is, focus on that. Use that as your bible to look at every day.
- [61:09]
Chris Do
Back over to you, Mike.
- [61:10]
Mike Lazzaro
I'd take it even further back, which is how do you know when to greenlight a company or a product at a company? And we give our framework, it's called the Go Gauge, and there's six questions you need to answer before you launch it. And it starts with, what is the product, why is it different? Who is going to buy it, and how many of them, which is the market size, it's not just like, you know, the golf industry is a hundred billion dollar market, but if you don't own a golf course, you're not getting $80 billion worth. Right. So we focus on like who are the and how many of them are. Because then you have to really drill into the addressable market and then how are you going to market it? Great products exist that never saw the light of day. Chris, that's like your superpower. How do you get stuff out into the world? And a lot of entrepreneurs underestimate that. I'm going to build it and they will come. Is not a strategy, that's a movie. How are you going to distribute it? So a lot of companies, this is the fifth think about all this stuff, but they don't think about the logistics. How are they going to get it to the customer, whether it's online or do they have to ship it? Is it a channel strategy? In that is the sales strategy and go to market. And the last which I would say is the least important to start if it's a big market. So if it's a really big market, this last one and it's basically the idiot's guide to the financials. So do the financials make sense on a napkin? Does it pass the smell test? And when I say financials, it's I'm going to sell the product for ten bucks. It's going to cost me two bucks to make, it's going to cost me another two to ship it. I think I can get customers for two bucks. So that means there's $2 left over for everything to pay for. Like the general administrative can I fund all that? And I see so many entrepreneurs creating complicated financial projections for businesses that they're so fucking clueless how it's going to work. Like literally they're like, haven't talked to a customer, have no idea if the pricing makes sense. But they have like, you know, the Harvard mba. And so that alone as an entrepreneur is worth the money. Because save yourself the pain. I've had at Shape Matrix. I did not do it for Shape Matrix. And it's been seven years of misery.
- [63:49]
Chris Do
All right, let me just quickly recap the six questions you want to ask yourself about whether or not you should greenlight a product or project initiative in your company. Is what's the product? Why is it different? Who buys it? How do you market it? What's your marketing strategy? How do you distribute it? And in terms of financials, keep it simple, stupid, don't overcomplicate it. Understand your numbers, right?
- [64:11]
Cass Lazzaro
That's exactly it.
- [64:13]
Chris Do
Wonderful. Cas, the last hack here. Give us the biggest, juiciest one. Drop it on us, please.
- [64:19]
Cass Lazzaro
All right, I'm going to talk about marketing. So we haven't really touched on that. And when you're a startup, you probably don't have any dollars to market. So what we did, and obviously this last company was a big one. We were starting a new category, social media marketing. Right. And social media management. But it's not like, yeah, we started the company, we got a little funding right away, but it's not like I could say, like, hey, give me $500,000 and like, that's going to be my budget. So what do you do? So you got to think about depending on your product or service, where are your customers and wherever they are. In our case at that time, they were at conferences. So conferences are a pretty cheap way for the most part. Some are $1,500 a ticket and stuff. But that's how we spent our money, our marketing dollars in the very beginning. So we went there and then I would negotiate two, first three for tickets and stuff like that. I'd pitch Mike with this incredible PR guy that was helping us pitch him for a thought leadership panel conference, which was great because as you've seen here, Mike has a lot of insight about a lot of things. So now I've got Mike, two other salespeople going to a conference. I've got Mike on stage. Now think about what's the cheapest thing I can do to brand our company in that way with all the extra customers that are walking around us at this conference, it's always around food and beverages. I will tell that to anybody until I die. So one time in a huge conference for Golf.com, we didn't know, like this was at the PGA show of America. I think that was what it was called, the Golf show of America. We had, there was like 10,000 booths. I got old fashioned popcorn machines that smell like popcorn for like six miles. And I just. We had a crappy booth that wasn't very pretty or anything, but we had our sales team lined up and everyone gets hungry. So they would just come over because they smelled the food. Number two, what we did once, we have Mike talking at a conference doing thought leadership and a panel, and we own every single coffee cup at the conference. And they're like, well, that could be 10,000 coffee cups. Okay, Best money I've ever spent. Every single time you put your brand on it, it's cheap. They're literally looking at you holding a cup with your brand on it. So what I equate that whole thing to is when you're a startup, punch up with marketing. Punch up, make yourself look bigger. There are a lot of opportunities out there that don't cost a lot of money.
- [66:53]
Chris Do
I want to stay on the conference thing because it's not a usual thing for people in our space to think about go to a conference. We go as attendees, but we don't know how to make a splash. We're not putting ourselves in a position of leadership and where people now chase us versus us chasing them. Right. I love this. Let me ask you a couple of questions here. So, yeah, get your brand everywhere. So you would sponsor the coffee cup. So the event organizer is happy for you to pay for that. Awesome. Best money you ever spent. So your. Your golf.com is all over the cups, right? People walking around, then they smell this delicious buttery popcorn. They come over to the booth. Maybe the bags are branded too. Whatever. Somebody scoops them some popcorn. How do we bring them into the conversation? Because we've been there. We go and grab the popcorn. We just go to the next booth. How do you engage them?
- [67:38]
Cass Lazzaro
That's like sales 101 here. Now we get to the real, you know, secret sauce of what it means to be a good salesperson. Because there's a marketing group that helps you get the lead generation. And now it's up to the sales team. So when you're there. And I'm gonna let Mike answer this. Cause he's obviously, like, the ultimate salesperson, along with our other co founder, Jeff Ragavan. Your job is to hook. You don't give that popcorn out until you have a conversation. Right. You better not give that popcorn out. It's not laying around.
- [68:09]
Chris Do
All right, team, listen. Pay attention to this part.
- [68:11]
Cass Lazzaro
Well, wait. But Mike doesn't always agree. I have a different approach.
- [68:15]
Mike Lazzaro
So I was the one who. I did most of the traveling speaking. I got most of the recognition. Cass did most of the work and made things work. I'm just happy that I got all the recognition. But you have to get People play the long game. No one's heard about your brand. If they're carrying around a coffee cup, they've now heard about your brand. That's step one. Okay, so brand recognition and just, oh, I've heard of them. What do they do? And so we didn't make them have a conversation with them, with us. A lot of people wanted to know because they felt guilty. People Are guilty. Taking things. Taking things without asking and seeming like a total pig. But, like, we love it.
- [68:56]
Chris Do
I'm right there.
- [68:56]
Mike Lazzaro
Yeah. And so what we would do is basically, like, get the coffee cups out there, and then they would see my column and Ad Age. I'd write about, like, how to market in the social world, right? I had a column and then I had a column. And fast. Well, not Fast Inc Magazine, which I'd write about startups. And then I'd show up at. We'd like, pitch speaking engagements. And this is all laying the groundwork, right? So you have to, like, there's no easy way to cold call today. It was easier back then. Lay the groundwork and then figure out how you're going to bring value to anyone you talk to. So popcorn is the best exchange of value. You know my brand now, and you got some delicious hot popcorn, right? And so do stuff that's like. That's cheap, that is impactful, that's not goofy. Right? Like, I was at the CES show, and the stuff that people are passing out at their booth, it's like, why? Like, I don't like giving away candy. I'm like, I'm just giving you poison, right? I don't like giving away tchotchkes that it's like, you know, they're going to throw away right outside. It's just kind of be smart. Like, what would you want? And you have a very creative audience. Everyone has superpowers and ideas. Creatives are much better at marketing their clients oftentimes and themselves. So think to yourself, okay, I'm Chris. If I'm a product or a brand, how would I market myself? You figured out a while ago it's why you have, like, millions of people following you. Right. But most people don't know where to start. And where you start is you just do it. Like, you just start. And so if you want to do your own popcorn at an event. Yeah. We hacked Cesar at 2019 where Peter Pham and I passed out about a thousand liquid deaths. No one had ever heard of the brand. We hadn't launched yet. We had it in our backpack. I kept going back to my room to get it. By the end, people were filling up their cans with regular water because they loved the brand so much. So don't market stuff that you don't believe in, but if you really believe in it, just force people in some way to get exposed to it.
- [71:10]
Chris Do
I still want to get to the sales 101 part where Cass says, this is the critical part. You Got the popcorn. I'm guilty of this. I walk up if I want something. I'm unaware of the booth. I feel guilty. I feel like I owe it to you to listen to three minutes of your pitch. It's this whole reciprocity thing. And I feel like now I've taken and I need to get back. So in the booth itself, I would love to be really practical and pragmatic about this. You got that bag of popcorn? What are you saying to that person? Give us a sample of the structure of it. Maybe not the exact.
- [71:40]
Mike Lazzaro
So we have a takeaway. So we always had materials. Cas is great at either two pager or pamphlets. We had giveaways. Cass didn't mention this, but we always had win, a trip to whatever. And people could enter by scanning or by putting in their business card. We constantly did that. And we had salespeople there. So people who are interested to be like, hey, this is what we do. If you have, like, you know, if you market in multiple languages, multiple countries, we have a system to let you hyper target content on Facebook. Facebook at the time. But then it opened up to others, and people who were dealing with that would say, oh, I gotta do a demo. And yeah, we. We usually in the back had a computer set up, but you could follow up afterward. But sales is not a, you know, one and done. It's like, we look at as building relationships. Like, how did people feel when they left our booth? Like, was it worth their time or was it not? Popcorn helps, but it's if they're going to spend 10 minutes.
- [72:45]
Cass Lazzaro
But the other, other thing, Mike, I think that I saw you and Jeff and all the other sales team doing is the conversation is about, hey, let me tell you about, you know, Buddy Media or Golf.com, it's more like, what are the problems you're facing right now in your company? So you talked about reciprocity, Chris. We usually have taught our salespeople to then turn it around and give back again, give back more. So it's not take, take, take, take. It's not quid pro quo. It's how can we help you?
- [73:15]
Mike Lazzaro
Yeah, it's give, give, give.
- [73:17]
Cass Lazzaro
It's give, give, give, and draw them into the conversation. Popcorn got them there. Now we have some stuff to give them. You know, at golf.com, we would like, you know, get Titleists to give us a driver. And everybody was crazy about, you know, new golf club. So they'd sit there and fill out their information, which helped with our lead gen. And Then you can say, because we're giving. What brings you here? What are you facing in your industry right now? What's happening with your company? How could we help?
- [73:43]
Chris Do
Okay, so you're there to solve more problems and give more stuff, and eventually, if there's a fit, you might do a demo or something. That happens.
- [73:49]
Cass Lazzaro
Yeah. They're going to remember you. But you can do all of this by punching up, being creative. I mean, one year at south by Southwest, it was pouring rain and somehow dropped to like, 48, 50 degrees. And we rented. We scrambled and rented golf carts, and we were. A mobile golf cart. Coffee, like, mobile coffee machine. And everyone was freezing, and we just provided the coffee in our coffee cups.
- [74:19]
Mike Lazzaro
Freezing and hungover.
- [74:21]
Cass Lazzaro
Yeah, freezing and hungover. But we were the coffee of.
- [74:24]
Mike Lazzaro
We were powering, and here comes coffee. Jesus. Like, da, da, da, da. You're your savior.
- [74:31]
Chris Do
I love that. Okay, did you call an audible in the moment? It's raining. It got cold. Hey, somebody get the truck. Let's slap on a label. Let's do this.
- [74:39]
Cass Lazzaro
Five or six days before our team did, I was watching. Yeah, we figured the weather, and it wasn't getting any better. It wasn't like it dropped all of a sudden. We would have been all in the same place, but we saw it, and then we thought, oh, my gosh, everything that we were gonna do was gonna be a waste of money. How can we get our branding out there?
- [74:58]
Chris Do
You know what I love about that is that you're not waiting to after the fact to make a decision. You're. You're kind of anticipating it and paying attention to this. And I love the second part that you said, because earlier in our conversation, you said, you know what? Don't fall in love with your first idea. Be ready to pivot and know that that's a loser. So you had a plan going in, and now that plan's not going to work. Most regular folk would just, no, we paid for it. We're pot committed. We're going to go all in on.
- [75:24]
Cass Lazzaro
This and shove it in.
- [75:26]
Chris Do
Yeah, holding two. Seven off suit. We're going to go in, right? That's for Mike. So then you're like, let's switch. Let's switch gears here, right? And we can change it up. And you do that. So you know what? Having heard this part, my team and I, we have some work to do. I mean, we have a lot of work to do, but I'm like, my God, we go to conferences. We're at the booth, and we do nothing. We pull them in we. We teach and we teach, and they go home happy and fed and like, hey, we got zero business out of this. Like, awesome, guys. Freaking awesome. Okay, we got some work to do. I need to end this. But there's one question that's been burning in the back of my brain, and if I don't ask this, I think people are gonna yell at me. And it's a light question. When Gary Vaynerchuk says to you, I'm going to use your conference room, I have to ask this question. What was in it for you? How did he pitch it? What did he say? Like, why would you say yes to this?
- [76:22]
Cass Lazzaro
Nothing. Nothing, Nothing.
- [76:23]
Chris Do
There's nothing in it for you?
- [76:25]
Cass Lazzaro
I mean, maybe.
- [76:26]
Mike Lazzaro
Well, Cass says it's got to be something.
- [76:29]
Cass Lazzaro
Mike had an idea.
- [76:30]
Mike Lazzaro
So I had what I was thinking, and it actually played out this way, is this is one of the world's greatest content creators. He wasn't at the time, he wasn't recognized, but I just thought that what he was doing was brilliant. And he says, I want to do what I did for myself, for companies, basically help them create content and market. Same thing he's doing today. In my head, I was like, we have the software. You're going to be the agency, and if you succeed, you will deploy our software alongside your services. Right? And we talked about that, Gary and I said, listen, I still remember this pitch. We went into the NHL's headquarters together, which was walking distance from the office on 6th Avenue. And when you meet with people at the time with Gary, Gary does all the talking, and he just. He just starts, and you just sit back. And we ended up winning business together from the NHL, which did I do. We gave him the conference room. Zero strings attached. I knew this was going to be one of my great friends in life, long term. I just felt it. We ended up doing a lot of business together. We've since we own Pickleball Team together, we help. We're part of his wine company, Empathy. We are investors in veefriends and own a lot of veefriends tokens. If any of your audience likes the veefriends community. So, like, sometimes you have to give way before you get anything. And this is an example that, like, we gave and what we've gotten in return is so far, lopsided on our side. We've gotten so much more. He wrote the foreword to the book and he said, I'm all in. He's marketing our book for us. He's got 40 million followers. So sometimes do what you think is right or that you want to do, even if you don't know what's going to happen. But serendipity is a good thing. I didn't know Cass was going to say yes at a wedding when a kid who was three years younger at 21 asks her to dance. I was nervous. I'm like sweating. I wasn't good with what they call the girls. And so I just went up to cast and I'm like, hey, you want to dance? With my sweaty hands and me. But like, if I hadn't, I'd be in jail or homeless. Right. Like, who knows what would have happened? And so just do stuff that you want to do or you think is right. And it's just like that's. That's this crazy thing about this awesome thing called life, which is just like you get to do. That's. You may not know why you're doing it, but you do it. And let the cards fall.
- [79:21]
Chris Do
For the record, as our audience is listening to spitting out whatever beverage they had in their mouth, thinking what I'm thinking, Mike, they're just called girls. You're like, they call them girls. It's like they're still girls. They have been from the beginning of time.
- [79:34]
Mike Lazzaro
I went to an all guys high school. I wasn't like, I wasn't popular. And so the fact that Castle is good looking, smart and had a heartbeat, she meant that she was my type, right?
- [79:46]
Chris Do
Yes. Yes. I love this. And for the gen zers, if you're listening, what I think what Mike meant to say, he didn't have the Riz, so. But he did anyway. Took a shot.
- [79:57]
Mike Lazzaro
Yeah. I still don't have the Riz, that's for sure.
- [80:00]
Chris Do
But you know what? You don't need to anymore.
- [80:02]
Mike Lazzaro
Yeah, Cass has the is.
- [80:04]
Chris Do
You're good. You're good. You got a good one and you're making it work. It's been lovely talking to you for a lot of different reasons. I want to mention this. I've been talking to Mike and Cass. Their book, shoveling stuff. A Love Story is coming out in June. Be sure to check it out. I've enjoyed the transparency, just the real realness, your depth of experience. I'm sure it's a fount of knowledge. And so I'm going to recommend everybody. If you've enjoyed this episode, please do look out for the book when it drops. It's a couple months away. Cass and Mike, it's been a real pleasure talking to you. I enjoyed watching you just interact with each other. Just you know, just a human. I'm just watching it and you know, I know you're not in the same room, but it feels like you're in the same room and it's just been really cool. So I appreciate you coming on the podcast, Chris.
- [80:48]
Cass Lazzaro
Thank you so much.
- [80:49]
Mike Lazzaro
Yeah, this has been really special. We appreciate it. And yeah, you're special content creator who really, you know, we feel great coming out of this. I do, at least. So thank you.
- [80:59]
Cass Lazzaro
I do too. Thank you.
- [81:01]
Chris Do
Thanks for sharing so openly. That's all I could ask for. If people want to look up whatever it is you're doing, check out the book, whatever it is. Where should we send them to?
- [81:09]
Mike Lazzaro
Www.cassandmike.com or just the book? Www.shelveling.com.
- [81:20]
Chris Do
Spelled out the way it's spelled.
- [81:21]
Mike Lazzaro
Out or with the exclamation spelled out the way it's. I mean, listen.
- [81:24]
Chris Do
Spelled out the legitimate way.
- [81:25]
Mike Lazzaro
Yeah. Like it's raw entrepreneurship. We weren't gonna like sugarcoat it. Let's just say that.
- [81:36]
Rich Cardona
Thanks for joining us. If you haven't already, subscribe to our show on your favorite podcasting app and get new insightful episodes from us every week. The Future Podcast is hosted by Chris do and produced and edited by Rich Cardona Media. Thank you to Adam Sanborn for our intro music. If you enjoyed this episode, then do us a favor by reviewing and rating our show on Apple Podcasts. It will help us grow the show and make future episodes that much better. If you'd like to support the show and invest in yourself while you're at it, visit thefuture.com and you'll find video courses, digital products, and a bunch of helpful resources about design and the creative of business. Thanks again for listening and we'll see you next time.