What’s it like to build a billion-dollar business with your spouse, and live to tell the story? In this special episode in front of a live audience, David Politis sits down with Kass and Mike Lazerow, Co-Founders of Buddy Media and authors of Shoveling $H!T: A Love Story About an Entrepreneur’s Messy Path to Success.
They open up about building cult-like culture, radical transparency, co-founder dynamics, fundraising strategies, pivots, parenting, and everything in between. With humor and honesty, the Lazerows share the unvarnished truth of what it takes to build something meaningful and survive the chaos along the way.
Takeaways:
Building a Cult-like Culture with Intentionality: Kass shares how she focused on creating a high-trust, high-engagement company culture through rituals, transparency, shared values, and even handwritten birthday cards. The foundation was purpose-driven work, and a lot of cupcakes.
Radical Focus as a Leadership Imperative: Mike emphasizes the importance of choosing just 3–5 core priorities each quarter and communicating them relentlessly. He admits that his natural state is distraction, and that focus, both personal and organizational, is what drives growth.
Fundraising Is a Relationship Business: Mike describes how he built trust with investors over time by sending updates, even to people who said no, and treating everyone with respect, from analysts to GPs. He reframes fundraising as offering a great opportunity, not asking for a favor.
The Power (and Pain) of Pivoting: The Lazerows recount the early missteps at Buddy Media, from virtual currency to raffles, before landing on a scalable SaaS product. They stress the importance of cutting old lines of business fast and committing fully to what’s next.
Marriage and Co-Founding: They describe co-founding as an intense version of marriage: with shared values, relentless communication, and radical honesty. Kass encourages couples to embrace their lanes and support each other’s growth, both professionally and personally.
Startups and Parenting Don’t Balance, But They Can Work: Kass shares how they intentionally deprioritized social commitments and accepted imperfection at home to build their company. She encourages other founder-parents to aim for 80%, not perfection, and to give themselves grace.
Quote of the Show:
"Being a founder, there’s no worse way to spend your day. And it’s awesome, right?" - Mike Lazerow
Links:
Kass’ LinkedIn: https://www.linkedin.com/in/kasslazerow/
Mike’s LinkedIn: https://www.linkedin.com/in/lazerow/
Get Their Book: https://shovelingshit.com/
Ways to Tune In:
Substack:
Spotify:
Apple Podcasts:
Transistor: https://podcast.notanotherceo.com/
#NotAnotherCEO #BusinessSuccess #Shoveling$H!T
Chapters:
00:00 Intro
00:46 Podcast Journey and Growth
01:41 Acknowledging Sponsors and Supporters
03:56 Introducing Cass and Mike Lazaro
05:33 Building Buddy Media: Key Strategies and Insights
08:19 Challenges and Successes in Leadership
14:09 The Importance of Transparency
15:19 Husband-Wife Co-Founders: A Unique Dynamic
20:09 Fundraising and Building Relationships
27:46 Marketing and Branding Strategies
34:09 Thought Leadership and Public Speaking
36:36 Navigating Business Pivots
38:25 The Birth of Buddy Media
40:31 Challenges and Successes of Custom Apps
45:20 Balancing Family and Business
48:50 Advice for Aspiring Entrepreneurs
54:58 Building a Positive Company Culture
01:02:21 Q&A with the Audience
01:11:11 Outro
Transcript
Mike: [00:00:00] Time is such a great thing and if you don't do the right things and you're just wasting time, you don't get that benefit of compounding the time and growth.
David: Awesome. Uh, thank you all for coming. This is amazing. Um when, when I started the podcast a year ago, I did not expect to be doing this. Um, at that point I was in Noah's room in the corner when he left for school, set up a bunch of boxes. Um, and, and now we're doing this, it's almost [00:01:00] 50 episodes, tens of thousands of followers across all the different platforms.
Um, so it's amazing to be here. This is the first of many. Events that we're gonna be doing. We've got a dinner coming up, we've got a poker night coming up. Um, so this is really the beginning of not another CEO in a much bigger way. Um than honestly I ever imagined really, since Nick and I started working on this together a couple months ago.
We've really picked up the speed. We're going much bigger in terms of what we're, what we're doing with the, with the company, with the brand. Um, and today's a big day to be able to be here and with all of you, um, and, and, uh, be able to interview Kass and Mike, who I've looked up to for a long time.
This is, um, this is a big deal. So, um, with that, I want to say thank you to the sponsors. We wouldn't be able to do this without sponsors. Um, first to CIBC, Ben Shepherd. Um, I met Ben last year. There's Ben. Um,
so I, I met Ben last year, um, and he [00:02:00] told me. You know, anything you want to do related to founders in New York, we want to support you. Um, and he actually took me down to this space and said, this is like, you can have this space whenever you want for any event. Um, and now six months later, nine months later, we're making that happen, which is amazing.
Um, we have Gunderson, uh, Ryan is here, I think, uh, or he was here, but, um, Ryan from Gunderson. Um Gunderson Detmer was our law firm at BetterCloud and they really helped us take the business really from the early days all the way through to the acquisition. And they were much more than lawyers for us.
They were really. Partners and advisors through the whole process. And, um, they've really been instrumental, actually have been pushing us to do a lot more with not another CEO and, and supporting us. Um, which is, which is great. And then Workbench. Workbench, if you don't know Workbench, John and Jess are here from Workbench.
Um, and
[00:03:00] John and Jess, they started workbench almost the same time. About the same time we started BetterCloud and really there was no enterprise tech in New York and they really put the flag down and said, we're gonna build the first seed fund. Dedicated to enterprise tech in New York, and now it's many years later.
Fourth fund was just announced. Um, amazing. You know, I work with them. I'm, I'm CEO and residence there. I'm at their office every week and it's just an amazing, amazing culture. So, um, thank you for, for the support from them. And then, um I need, I do need to say thank you to the boys. No. And Sammy, um,
when we started promoting this event and I said let me show you what we're doing on LinkedIn. And I showed them the LinkedIn post and, and they said to me, we can do better actually than, than what you're doing. And they did a Canva, they created a Canva video in like an hour. I posted it.
So far it's been the best, uh, performing thing that I did for this, for this event. So, um, so anyway, without [00:04:00] further ado, um, I want to introduce Kass and Mike. Um, again, this is, this is a big deal for me. I'm really excited. Um, everyone got a chance to you have your hands on the book. Uh, honestly, when I was reading this, the other, uh, I read it cover to cover in a day, and I literally thought to myself, I emailed them, I said, I feel like this book, like I may have written some of this.
Like, and so this, this is really, um, exciting. So I, I made sure to write this down so I didn't get anything wrong. Um, today's guests are a true power couple in the world of an entrepreneurship and technology. They founded several companies together, including uwire golf.com, and most notably, buddy Media.
Buddy Media was the world's leading social media marketing platform. They launched it in 2007 and sold it to Salesforce for 745 million in 2012. Buddy Media was one of the original, original New York Tech success stories, one that really put New York, B2B Tech on the [00:05:00] map. They've also become prolific investors backing companies like Liquid Death, Scopely, and Braze, among many others.
Most recently, they published a deeply personal and honest book about their journey called Shoveling Shit, A love story about Entrepreneurs messy path to success. So with that, please welcome entrepreneurs, authors, investors, husband and wife, Kass and Mike Lazaro.
Okay. Alright. We're gonna get started with, with the first question I ask every guest, what is the one thing you did at Buddy Media, big or small, that had the biggest impact? And you do again, if you're, if you start another company, if the future, okay. We'll start with you.
Kass: I am gonna say, I created a cult-like culture.
So the first four letters of culture is cult and we need to do it in a positive way. And so I [00:06:00] made intentional choices and every single touch point with employees along the way was important. And the glue that kept it together were not, it was radical transparency. It was bonding events. I know everyone's gonna say it's hard with remote like workforce.
It's not, you just have to make the effort and then figuring out a cause that's bigger than yourself. So we had Cycle for Survival and that really brought a lot of unity to us.
David: When you were hiring the first set of people at Buddy Media, what were you looking for in that first?
Kass: U utility players. So the first five to eight players that you have on the team are gonna be utility.
They have to do multiple things at once. And when you figure out your first, like, let's just call it first product market fit, I don't really think I. I think it's like an oxymoron. There is no, like, first it's gonna be like the last product market fit. You then start to hire people with specialties. But the first 10 probably have to wear a lot of [00:07:00] different hats and you're gonna be moving them around quite a bit.
David: And when you were interviewing, like how many people did you I've, I've interviewed a bunch of CEOs who've said I interviewed the first 400 people we hired all by myself. And you know, I was involved in every interview process. Did you do that in the No, I think
Kass: that's an absolute bottleneck.
I think it's like totally the wrong way to do it. I think your job is to fi find someone that can mimic the, the morals and values and mission of what you want, and then delegate that. And their job is to find someone that's almost like a better fit than they are, a better fit in terms of skillset. Hmm.
And we were able to do that. I think we had one year, we grew about 120 employees, uh, in like seven months. It was crazy. And our head of recruiting was Pam Schloss and she hit it outta the park. It was, it was incredible.
David: Did you, did you, do you think that was based on having the values defined and very clear?
Definitely. You
Kass: [00:08:00] have to have your, what you stand for, what's important that mission values, all of it has to be repeated constantly. You can't just say it once and then say it like in the onboarding day, you have to say it over and over and over again, as well as what your goals are. You're you have to focus too.
David: Hmm. Mike, how, how about you? What's that one thing you would do? Again,
Mike: I just think it's all about focus and companies that really hyperfocus don't try to do everything. And we're in an exciting time of ai and you could do this and that and this and that, but what are you trying to do as a company?
And then what are the first three to five things that you need to do to accomplish that? So we always said focus, but then we worked with about, we've made about a hundred investments. We could never really define what that means, right? Focus. Okay. Okay, I'll focus. But what it means is really [00:09:00] define your future state.
What do you want to be? Right? So Mark Benioff launched Salesforce, number one CRM, and then, okay, if that's what we want to be, what do we need to do to get there? And that's how you wake up in the morning and you basically know what to do, right? A lot of founders, I don't know, you know everyone here, but a lot of founders wake up and there's overwhelmed because there's a lot of like shit to shovel, right?
A lot of stuff going on. And I always liked having one piece of paper. That had everything I was focused on.
Kass: So, and there's a lot of distractions.
Mike: It was product, sales, customer success, whatever it was at that time. And you could push it forward. And pretty much most of the time for me, focus was sales.
Like and selling not only to new logos, new customers, but a big part of our growth. So we in three years we won from zero to 50 million of a RR. Big part of our [00:10:00] growth, of our growth was upselling, right? So get that customer, and it was a land and expand business. A little different than some businesses today, but that business was like, okay, we have Unilever, but they have another a hundred brands, let's go.
Right.
David: And when you were doing that, I mean, I think one of the challenges for founders in general, I will speak for myself in this, is that you want to do so much, right? And you see all the opportunity that's in front of you. How do you focus? Like how do you, how do you temper that even for your, your own ambitions?
Mike: It's hard. It's hard for me. I'm not very focused by my natural state is unfocused. I'm more creative than cast. She's much more of the operator cast thinks in spreadsheets. I think in kind of screenplays, um her love language is spreadsheets. Um, and for those of us who have, let's say, a more distracted mind, you need something to hold onto that reminds you [00:11:00] otherwise, you're down rabbit holes and it's some of those rabbit holes we're okay.
It let us get to the future faster. But organizations, the problem is, as a leader, if you're not focused and you can't explain to your team what are your three most important things, your team isn't focused. And if your team's not focused, you're just paddling in different directions and spinning around.
Right? And it gets even more important as you have a bigger staff. 'cause you're just burning cash, right? Like. You're trying to go from a startup to a company, so losing money to profitable, and if you're not focused while you're losing money, you're just shooting yourself in the foot
David: in a very tactical way.
How, how often would you define those three priorities?
Mike: So we did it every quarter, even though we had kind of an annual budget. And the reason why we did it every quarter is because there's a, a, we're growing so fast. We had new employees and [00:12:00] new team members. We had a quarterly meeting, which we treated like a board meeting.
We presented to our team as if they were the board financials and all. So we basically, Hey, we trust you. We want you to be empowered with information. We firmly believe that surprises are much harder to digest than bad news. We didn't have much bad, a ton of bad news, but we lost customers. We lost the competition.
We headquarters that weren't great and we would basically say, Hey, and the key, as a leader, you have to say get the elephant in the room. This isn't working. Take responsibility and have a plan to fix it. And so we did that pretty much every, and the other thing is we realized that our roadmap had to change often because we're so sales focused.
So it was a software company and you know, we'd, typical discussion was the head of sales, we need this for this customer. If we don't get it, [00:13:00] don't forget we're not gonna land it what
Kass: you do. You would walk,
Mike: I'm not gonna talk about that. Um, and then the product team would be like, okay, you need that, but I have this other a hundred things.
And then you're. And then I would, so I grew as a leader, um, really with Kass's help, but I was getting in the way 'cause I'd walk, like I love engineers, always have, always will like builders or, um I just love and I would walk into like the engineering pit to be and just shoot the shit, right? And I'd be like, oh yeah, that'd be so cool.
And then you
Kass: see this face right here. So happy. Well, I didn't know.
Mike: I didn't know, as a founder as a CEO, you don't know your impact all the time. And so we didn't just have a conversation. I'd be like, yeah, that would be cool. And before you knew it, like that engineer had changed the roadmap, which then pisses off my head of technology who then comes into my office like, what the fuck?
Right? Like, and so we just constantly had to align everyone [00:14:00] because we now we're growing fast. We quickly had offices in London and Singapore and all these places and we've never done this before.
David: Mm-hmm. One of the things, I know Cas, we've talked, you, you've really talked about transparency a lot.
Yeah. And, and Mike just mentioned it. Was it hard for you to be transparent? Me, you not, not you. I, have you ever met her? I was like, I mean, but from day one you were like, we're gonna say good, bad, ugly. Yeah. I mean,
Kass: I don't hide, I don't hide things very well. Like I zero poker face, so. I if big investors came into our office, there's a good chance people knew that we were probably raising money.
And so when they would come out, they'd be like, oh my God, like, what's happening? And I'm like, oh, we're, we're talking to investors just like we always do. And they're like, why is everything okay? I am like, everything's great. We're just gonna constantly and talk to investors because you're always raising money.
And I had no problems just telling them the truth because Mike said it like, transparency is glue [00:15:00] right? And nobody cares about, well, I should say it this way. When you have bad news and you have pivots and failures, which you're gonna have, you want people to stick around and not jump ship. And they do that if you constantly tell them the truth and you're not hiding anything from them.
David: Hmm. One of the things obviously that's unique here is your husband, wife co-founders. Um, can you talk about that? Decision and that journey to, to, to do that. Sure. And um,
Kass: so I don't think it's probably the best idea that you start a company when you're dating. Like, I don't, I don't think like anyone's going there saying like, oh, this is like great.
But when I was working at an agency, I was working for the interactive arm of Leo Burnett in Chicago, and Mike was finishing up his, his stint at Uwire that was just acquired and they were going public with student advantage. I would come back and complain about very [00:16:00] big visionary product. I. Ideas, right?
Like, this wasn't working. I don't understand sales. And for, for some reason, they put me as director of business development and marketing and pr, which made no sense to me. The marketing and PR are fine. So I would tell him that, and then he would come back to me with very, our operational questions. So we were each other's kind of confidant in terms of work.
And what it became clear is we had very different lanes. And that's what you want as co-founders. If you're gonna have more than one co-founder, you want very different lanes, and you want that implicit trust and absolute respect in each other's skill sets.
David: Hmm. One, one of the quotes I, I, I wrote this down is one of my favorite one.
It says, it's not that marriage or having a co-founder is inherently bad. Rather the culprit is insufficient. Work done upfront before saying I do and signing the legally binding paperwork. It takes effort, tons of communication and care to make both continue to work, right.
Mike: [00:17:00] Yeah. I mean, it's not that dissimilar.
Like who here has a co-founder in their business? Yeah. Are, and you're married to your co-founder, right? Like you guys talk first thing in the morning, last thing before you go to bed, you're in sync when done. Right? Right. Like you want to kind of over communicate and just the flow of the relationship is similar.
You have this honeymoon phase, right? With a co-founder, you're so excited you haven't done anything. It's like the world is your oyster. You dreaming big, there's passion, right? And then you launch something and it's like, oh shit, that didn't work. Right? And you have to have some tough conversations. You
Kass: get resentful and that's like when you start pointing fingers, that's
Mike: like kids, right?
You have kids and you're like uhoh. Um, and so it's what's key to both is shared values, shared work ethic, and all of these conversations that you should have upfront. Which is basically like, what's your vision? How hard do you wanna work? Is this something that you'll do for 10 years? Are you doing it [00:18:00] exclusively or are you doing it on the side?
And when you don't have those conversations, it ends in a divorce, work, divorce, uh, and we've seen it again and again because it's hard for two co-founders. There's a lot of ego involved, there's identity involved, there's just like personal mishigas involved. It's hard for people to change once they start going, I.
David: It's a, it's a real, I mean, I, the number of co-founders that I see break up.
Live Cam A: Mm-hmm.
David: It's, and, and, and in many cases you say, oh, but you guys decide to start this together. And they're like, yeah. They were like a friend of mine through a friend, and we both had thought it was a good idea, jumped in, signed all the docs.
Like how, how, like when you see the best co-founder relationships, not even just your own, but the ones that you've invested in everything, how much time do people spend? Are we talking about like
Kass: they, they, they've definitely had serious conversations because when I do the due diligence for our investments, I am literally asking one of the co-founders about the other co-founder.
[00:19:00] So I'm kind of dividing and kind of doing like probably good cop, bad cop stuff on them. But it's interesting because I wanna see one, do they know what they don't know? Do they believe that the other co-founder, like get, like, is a big solution to their gap of skillset? And do they respect. What that person says.
Live Cam A: Hmm.
Kass: So if they can answer those three questions, I'm usually super psyched. Like I, we will never get a deal where Mike says, okay, I love this business model, but I don't know about the people. Like he knows that he thinks the people are gonna be good, but he needs me to go deep on them.
Live Cam A: Hmm.
Mike: I like all entrepreneurs, that's how we've done a hundred deals.
Mm-hmm. Um, because we've looked at
Live Cam A: many more Yeah.
Mike: Like thousands.
Live Cam A: Yeah.
Mike: And I just think entrepreneurs are the best. I mean, they're they're optimistic. They great energy country's been built on entrepreneurs and so there's just, it's the national [00:20:00] pastime business. And so I get very excited about ideas and then I throw them over to Kass and she kind of does the real work.
Live Cam A: Hmm.
David: Let me, let me ask about fundraising. 'cause you, raised a good amount of money relatively quickly. and I think Mike, you kind of led a lot of that. Yep. we just published actually on the, substack, the feeding the Baby. Yep. I saw it go out. can you, maybe talk about that process and really more I think that for a lot of first time founders, when they go out to fundraise they, think they're the only ones that have any problems with fundraising.
They say, oh, Dave, I talked to 10 people. They all said no. So I can't raise money. I'm like, well, it's gonna take a lot more than, it's gonna take a lot more than that. that's so cute. 10 people,
Mike: that's a Tuesday.
David: can you talk a little, and, also maybe I wanna talk about that I also, yeah, let's, start there.
Mike: So,
you know, and I even do this today, you're always raising [00:21:00] money. You're always kind of out there networking, talking to people with money. And we do, we have a venture firm, right? That we've raised money. We don't raise money for private ec we buy companies as well. Dina who runs one of our businesses is here.
and I I don't look at it as, I'm asking them for a favor. I look at it as a relationship built over time and our best investor relationships. We provided value or built the relationship years in advance. And I'm thinking of people like Jules Malt, who was an associate at IVP, who then became a partner, then became so rich, he retired.
and they've done incredibly well. Jeff Richards at GGV. and a lot of investors never invested, but I'm still friends with them, right? Like Jeff at Flybridge and, David at Venrock and people who I, we [00:22:00] just became friends 'cause we helped out. And so look at it as relationships.
Look at it as. How can I help you? No matter how much money the investor has, they got issues, right? They have portfolio companies that need help. If you know ai, maybe you can help them think through how AI is gonna impact their firm. If you have tickets to the Knicks, invite one right, that you met at an event.
if you have tickets to the Knicks, you probably don't need to raise money because they're so f*****g expensive. but it's where I see it and what happened. And it's a mentality. It's a founder's mentality that you're not asking for money, you're giving them the greatest opportunity to multiply their money, right?
You've gotta believe in your product so much that every meeting you go into, you have to think that they're crazy not to do it. They still won't do it. Most of them, but you have to believe in it so much. [00:23:00] And if you don't, you have to rethink the business.
Kass: But you're
forgetting one of the biggest things that you did.
Mike: I'm
forgetting a lot. I'm kidding.
Kass: But
he, would write these epic board letters before every board meeting and we were very intentional about board meetings. And he used to say that these board letters were really for him to think through the business. Right. It wasn't like he wanted to have a 10 page letter to the board, but it was his way of organizing information every quarter.
Right. So, or every month when we did it. And he would then strip out. Anything that was confidential. And then he would send it to all the people that we hadn't raised money with yet or hadn't, or said no. And then he would send that out. Just say like, Hey, I just wanna keep in touch and give you an insight into what's happening.
And so those relationships were built. when he's saying he built them over time, that's how he built them. And he would take 'em out to lunch, stop I'm in the city, I'm stopping by, or he's going there to say hi because he's building it so that there's excitement or there's [00:24:00] at least brand awareness of who you are when you're going to raise.
David: And I think part of the benefit of doing that probably also is you're building the credibility. with the investors that they see that you're operate, you're executing. You're, an operator. you, know what to care what the right things to care about are.
Mike: Yeah. And it's like no one's a known quantity until you are so now. It's relatively easy to raise money after you return all this capital to investors, right? But I'm really talking about when we were, I'm from the suburbs of dc. I knew no investors went to Northwestern Journalism School, met no investors.
So all these people we met over the years and we got very lucky through our networking golf.com we sold and then bought back, but we needed to get it funded. And so we hit the road and happened to meet a lawyer who loved to play golf, [00:25:00] who set up a lunch with his friends at a country club called Medina, which I'd never heard of.
But they hosted the US Open right after. And literally in a lunch this, baby Jesus lawyer found our money. I was like, man, right. And that was so like we would've. If that company went under, we were both in, she would've had to go back to the agency world. I guess I would've tried to be a journalist.
I don't know, maybe I would've started something else.
Kass: Maybe sales.
Mike: Maybe sales. But you get really, if you just keep going, your luck will happen. And it's not, you have to be patient it's been 30 years and we're still building and hustling and everything, but every day, every week, every month, you have to do the right things.
And that's really what the book's about. It's about these two things of like, shoveling shit is like miserable. being a founder. There's no worse way to spend your day. And it's awesome, [00:26:00] right? it's like, oh yeah, I'm miserable. Hey, you wanna do anything else? No, I'm doing exactly what I'm supposed to do, right?
Most other things that are miserable, you don't want, like, I don't like sharks. So if I'm in the water with sharks, I don't really want to be there. But for some reason we are able, as entrepreneurs there are a lot here. We fall in love with this suffering.
David: Yeah.
Mike: In, a really weird way.
David: It's true. I think one of the things that you said in the book, you talked about replying to emails.
Mm-hmm. Um, and I think just in general, like when we talk about fundraising, a lot of people give me the advice when we were fundraising that it's like, don't, don't respond to the analyst. Don't re you know, don't respond to the principal, don't respond to the only, re only have them call with the partner only.
And actually, most of our, most, the, the money we raised came through a principal who called or a VP and I responded to every Yeah, same email. Same. Yeah.
Mike: No, I treat everyone. I mean, Jules most Jules is a
David: great, I mean, he's,
Mike: he [00:27:00] came to an event we had in 2008, I think.
David: Yeah.
Mike: Launch event at Hill Country Barbecue here in New York.
Uh, we didn't have a budget, so I asked Gary Vaynerchuk to speak, who had a little social media following. He came to that event and then I started sending him these letters. I'd visit him in on the west coast and he they put in 20 million at a $80 million valuation. Um, two years in. And that was like the key money that led us accelerate.
'cause at the time, software was like expensive to build. Now it's like you go to lovable and it's like, hey, build me a social media management system. Okay. And it's done. Um, but at the time it's like unfortunately things were expensive. Um, and if you want like a players, you're gonna have to overpay for them.
Still.
David: I actually want to take that you said that about building software. Um, it's a good transition 'cause. You could probably vibe code, you know? Yeah. Buddy Media today with like and a better
Kass: version. Yeah, yeah.
David: Like in a weekend. Yeah. [00:28:00] Um, and, but I think that one of the things you did very well and when I would see you speak when early days at Greycroft events and the Hamptons and everything, one of the things that was always amazing is what you did with the brand.
Mm. And I feel like today, in today's world, that actually is what separates, it's not really, did you build the best software? Yeah. 'cause anyone can build it now. It's really what do you do with the brand.
Live Cam A: Yeah.
David: Um, and can you maybe talk, I mean you, there's some really good stories. Yeah. Um, I
Kass: think I. So I was a basketball player, tennis player, and golfer.
Right? That's how I grew up. I actually loved basketball more than anything, but I wasn't as good. And clearly I didn't get the height jeans. Um, but my dad always was like, he taught me so much about marketing, um, even though he was a lawyer. And just this concept of like boxing people out and you can change people's perception and that's what marketing is.
You just change someone's perception about anything. And with Buddy Media, I knew we were in this space. It was crowded. We had almost like 40 competitors when we started in [00:29:00] 2007. Like that's how, like it was a new market like. It was just like took off and had 40 competitors, like really good competitors.
And how was I going to punch up? How was I going to box people out? Right? So one is just change their perception. Make us look like we're bigger. So we didn't have a marketing budget in the first year, but I would get Mike on the stage as a thought leader. And then we'd have I could get like bags for the hotel doors, right?
And that was dollar each. And we would just use our money, whatever we could. And then, um, we'd own all the coffee cups. Right. So we had one event that we would own and own all of it. So we knew everyone was gonna show up for that meal that was being provided. We were gonna own every cup that they were gonna walk around with and Mike was gonna speak.
So that was like a trick that we learned, like, don't spread it thin, go heavy into like one thing. And then by the time we got our traction, especially [00:30:00] with um, being the software, the social media, marketing software, the platform, I convinced the board, and this was just crazy. I convinced the board that as a social media company, that we needed to do print ads, which is just stupid in a lot of ways, but that we had to be different ' cause everyone else was just running paid advertising.
So they were doing paid, owned, earned, whatever they could do to get their, their market share. And I said, okay, let's go and be like, the time. It was like Accenture and IBM and all these other big things and they were at airports. So let's own all the airport apps. I love this
David: story. Yeah.
Kass: And we did it and I said we can't do it for a year.
And this is where they got really mad at me. They're like, okay, so this is for a year, this million dollars. I'm like, no, it's from. Thanksgiving through January and they're like two months. Like, what are you talking about? I'm like, just trust me. Everybody will travel. So we put people in front of anywhere you went, any big hub [00:31:00] where you would connect, you'd go across the country.
They were everywhere. We owned charging stations, which were new for an airport. Mm. We owned when you went down the campaign, the campaign was
Mike: power your connections. Yeah. Which made the charging stations.
Kass: Mm. And then we did, um. The print ads as well. So then we like, um, ad week and add age. So it was just everywhere.
And then it, it was like, almost like overnight. By January we had, there were two things that happened. One, it was like we were bumped up into like so far out the leader that nobody else was there and like everyone was way behind me. And number two, the amount of pride that employees had. It was such a boost of I made the right choice to work here.
David: Hmm. And one of the things I, I love is just the, can we talk about the billboards? Yeah. Um. And like kind of how they, how they kind of lived on
Kass: Well, the best part was, is back then, um, 'cause when, when did the markets change? Was it [00:32:00] 2006 or eight?
Mike: What do you mean markets change? Great financial.
That was a great financial crisis.
Kass: Seven, eight. Yeah. 7 0 8. So nobody was spending, but, but we had, and nobody else was replacing those billboard ads everywhere. So we had them on and they were
Mike: analog. They were analog. They're print, they print, put it up
Kass: print and, and nobody was replacing 'em. So we had half of our market.
So think of like the top 15 airports, probably eight of them. Had them up for over a year, I think. I think
Mike: Seattle is still up. My Seattle is up there like forever. Yeah,
David: it was my favorite
Mike: right here. And these were like as big as this, like in Chicago, you'd go down the escalator to go from like sea to beef.
Anyone knows like United and like you go down that Es and it's like Buddy Media, how are your connections? And like, we're a tiny little company at the time. Um, ca made us look so much. Yeah, but a lot of the stuff wasn't paid it was like everyone can do thought leadership, figure out like what your lane is.
And I found different channels [00:33:00] like Scott Galloway had a company called L two, I don't know if you remember L two.
Live Cam A: Mm-hmm.
Mike: Luxury Marketing Consortium where he would do all these events. They all needed to know about Facebook and Twitter and Instagram and YouTube marketing. And so I'm like, Hey, I'll come in and like every event, it was like shooting fish in the barrel, right?
I'd go out to CES, all the marketers were there and I would go into like their marketing meetings and tell Coca-Cola, here's your company on social, right? This is what social means for your global brand. And every company can do that.
Kass: I mean, we did, you have to figure out where they are. We did a South by Southwest one year, and granted we also owned the stairs, right?
That they came down or came up in that airport, but. It was raining and that's like unheard of right in Austin, like at that time of year. So, and cold. And cold. It was freezing. So we somehow, I don't know how the marketing team and I figured this out. We got golf carts and we had coffee [00:34:00] and we just drove up and down the streets and we were powering your connection, right?
Like your vibe, your everything. And we were keeping people like warm. It was fantastic. Do,
David: do you think on the thought leadership front, were you comfortable like doing that day one? Like was that Not at
Mike: first. Um, because a lot of
David: founders that I talked to are not at first.
Kass: Really?
Mike: Yeah, not
David: at first.
Kass: That's so not true.
You love talking. Why are you
Mike: heckling me? I'm saying like, when we started I got very nervous. I would like sweat. I wouldn't eat beforehand. I remember this like I could, because I'd never done this level public speaking to like, yeah. I remember going, one of the first one was at p and G's. Like marketing event, which they fly all their marketers in.
And it was like a thousand people like, 'cause it's like big company, like they own all Were you wearing
Kass: a suit?
Mike: I was, yeah. Yeah. Um, and it was it's stressful, but like, one of the things we've [00:35:00] learned in the process with the book and reading the book is you have to lead, lean into your pain, right?
As entrepreneurs, it's like the pain you're experiencing. That's a problem you could solve with a business. And what you don't like doing is often what you have to do, right? Because we're all instant gratifications, not soon enough, we all like are addicted to comfort, right? Like the dopamine hit.
And distraction. And distraction. Being able to focus on stuff that's really important but uncomfortable I think is a superpower for entrepreneurs that. You know, I didn't like asking a thousand people to buy the book personally. Right. Last, last weekend, two weekends ago, I basically texted everyone on my phone like, I somehow met you at some point.
I would love You
Kass: did. It was like, it was like seven hours ago. Like, I
Mike: didn't want to do that, but like, you gotta do it. Right? Like, if not now, when? Mm-hmm. Like, [00:36:00] it's our life story. Like I kind of believe in the product. Um, we went into people were very surprised that we set up a table in Central Park that we put out a sign free entrepreneur advice to sell our book.
Right. And people were like, why are you like, was that staged? Were those your kids in the No, we just went in. Because if you're not willing to go into your local park and sell your product, like, like, what's it, why? Like, if you, if you don't believe in your product so much that you will kind of ask for the deal, then you're in the wrong business.
Mm. Yeah.
David: I think one of the things that I actually did not know until I read the book was around the pivots.
Kass: Mm.
David: I, I didn't realize actually that there were any pivots in the business. Um, that's
Kass: great. I did my job.
David: Yeah. Um, can we talk a little bit about that? Because I, I, I went through let's say a, uh, reimagination of what BetterCloud was at at one point and, and, um, I think when you [00:37:00] have a team and you have people, it's hard to do that.
Yeah. Um, and, and people have their livelihood and their careers and everything. Like, can talk a little bit about
Kass: Yeah, I will. I'll let Mike take you through all the amazing ideas he had. And I will say though, that leading a company through a pivot is enormously challenging. And again, I will go back to if you are radically transparent, then they will jump alongside you.
Right. Even though they're afraid. They're afraid that all of a sudden you're turning the ship around or funding didn't happen or. You're going with this client versus this one. So it's, you gotta be very transparent. Let's talk about our first idea. I mean, I'm sorry, your first idea.
Mike: Yeah, so I mean, every company really pivots in some way.
Some are really big if you're trying to do something new, some aren't. Like you launch a pizza place and like you have certain types of pizza that you didn't know were gonna be so popular, some that no one ordered, right? And [00:38:00] so as a leader, there's three things you can do when you get punched in the face or no one shows up, right?
You could keep doing what's not working. That seems silly. You could shut down your business or you could pivot. And Eric Reese, who kind of term coined that term, it's basically like pivot is a, not just an evolution, it's kind of a complete change of what you're doing for Buddy Media. The company got started because Mark Zuckerberg got up on stage on May 24th, 2008, and invited developers to build on top of the Facebook platform.
And why that was important is up to that time, the internet was a one player experience. All of a sudden your friends were there, right? The social graph, this virtual representation of real life relationships, let you build Zynga, play games with friends, it let you build apps that were inherently social.
I thought that was the future of the internet.
Kass: What, what day did you think that
Mike: it was the day she [00:39:00] was, uh, birthing our third kid c Sectionally. Um, and I was in the waiting room on my Blackberry and I was just blown away. And so I didn't know what we were gonna do, but I knew we were gonna do it. She, she got wheeled in with Viv, our daughter's.
About to graduate high school next week, so we'll be empty nesters in the fall. Yay. Um, and um, and I said, well, I got it. I got the next business idea. She says, you're a fucking asshole. Like, I just had the kid. I said, don't worry, we'll figure it out. They're kids here. Oh, sorry. Hi. Um, I mean, it's called shoveling shit.
Like, like you knew that when you broke came. Um, and uh, and basically I didn't have a business model. I had a market that was small but I thought would be bigger. And so we launched with something called Ace Bucks, which was not a good idea. Was
Kass: anyone around for ace bucks? Please say No.
Mike: It was not great.
It [00:40:00] was massive inflation. We have some fans, um. We, massive inflation in the currency and no purpose. And then we did a raffle product, which was, that was
Kass: horrible.
Mike: Basically illegal. It's gambling. Yes. Um,
Kass: horrible.
Mike: Yeah. Um, I
Kass: was not for that one.
Mike: Oh, you didn't detail it for the record? No,
Kass: I, no, I, I did everything I can and you, you just went right over it.
Okay, now
Mike: we're changing history, whatever. No, that's not
Kass: true.
Mike: Um, it's easy to play whatever. Um, just keep operating. Oh, the, and then we went to custom apps, which worked really well. We sold so many of these. It was like the FedEx send a package
Kass: and the Hollywood hair, the Hollywood
Mike: Hair Makeover app where you could put Jennifer Aniston's hair on your head and like send it to your friends.
Hey, should I get this haircut right? The problem with that is we couldn't hire, we're selling a lot of 'em, but we couldn't hire enough developers and we went and always
Kass: wanted something and they always
Mike: wanted to. So we went into a board meeting. We're like, this is service [00:41:00] business. We came up with the software idea, which we productize send.
All of this functionality became SAP widths, social applets, which you could like drag and drop together. And then from that was two years in, so it was two years of pivoting basically. And then the next three years we got to 50 million on the back of that and we went from 20 employees to a lot. I forget how many we had when we sold.
Um, and I love pivots and I love ripping the bandaid off. And I love kind of looking at the data and making decisions. We're talking about books and the problem with the book industry is you don't know, like, I've been doing all this work and Amazon doesn't give you data like, good luck.
Kass: Wait, are we really, are we really going into this?
Good luck
Mike: with like Barnes and Noble, but like, it's kind of frustrating in a business, you should be able to have your dashboard in a real business book. Like books are not really a business tell,
Kass: but tell everybody how [00:42:00] fast you would pivot.
Mike: So the only way I've always believed that the only way to pivot is like radical pivot.
You can't have one foot in the old business and one in the new. So we stopped doing custom apps and Kass had a huge fight.
Kass: No, I, no, I did not have the fight. He had the fight with me.
Mike: Our head of sales, who's one of our best friends, Jeff Raghavan. We officiated his wedding. It was a one fight where, 'cause he was making money, right?
He was about to close. He a sales guy selling all these things. He was about to close
Kass: two and a half million dollars in custom apps. And that's a big, and
Mike: he wanted to do both. And we're like, no. Like, this is the business. Like, cut it off
Kass: and tell 'em no. That was a, it was a drag out
Mike: for salespeople will take the know, the easiest way to make money.
So if you give them options and they could sell this, which is easy versus this, this is hard, you're never selling
Kass: this. But, but tell them, answer the question [00:43:00] about how fast, like you went into a board meeting. I thought you're guiding me
Mike: through these answers. Um, this is like assisted living. Um.
Kass: This is what you have to look forward to.
Mike: Wait, where am I again? Um, and so basically I got up, I did, I think it was a Wall Street Journal. I was doing it. Um, Facebook had an event. They launched some new APIs and in the journal I announced that we have the first ever Facebook page management system to manage your Facebook pages.
This was news to our head of technology. This was news
Kass: to everybody.
Mike: And so the company was like, wait, what? We haven't even talked about this.
Kass: So he announces that Wall Street Journal,
Mike: and I wouldn't recommend this. Why am I talking like, I wouldn't recommend this as a leader leadership thing
Kass: meeting? Like, yes, not a good leadership move, but, and it turned out that how quickly he does things,
Mike: but what it did is it got everyone to focus on, oh, that we have to deliver.
And we sold it before we had it. We kind of it wasn't fake it before we make [00:44:00] it, but we were building it as we were flying this airplane and. Every time a company that we work with hesitates about a pivot, they're wasting time.
Live Cam A: Mm-hmm.
Mike: They're wasting energy. And the, and the money involved is a lot of the people that you post pivot.
You don't the people you have, you don't need all of them. So you have to lay people off. So it's hard. And what's interesting is, I was talking to a founder the other night, founders will not lay someone off because of fear and they don't wanna have a con conversation. It's like $150,000 a year to keep this like slacker on board and they won't even buy lunch for the company.
Right. So the amount of money that entrepreneurs waste is egregious. Like, I look at everything, it's like, oh, how much is this person costing? And is it, and like we never hired salespeople until everyone else was like totally overwhelmed. [00:45:00] And you know, pivots. Like everything are scary, but once you do 'em, they feel great.
Kass: Everybody's happy.
Mike: Like, it's just like you feel lighter and happier and you're not full of like uncertainty and doubt until like you've launched the new thing and that doesn't work and you're like, oh yeah, do it again. So you get tiring.
David: Um, I want to transition a little bit Cas to, um, there's a chapter, I think it's called Imbalanced Life.
Mm. Um, and there was a mention here of you having your third child and in the middle of all this mayhem, um, can you talk a little bit about kind of how you balanced building a company and building a family?
Kass: Well, we didn't, so Mike and I actually had, I think, one uncomfortable conversation. I mean, it wasn't that uncomfortable.
We both, well, we
Mike: should tell them about that part. Mm-hmm. What, I'm sorry. Okay. Well,
Kass: uncomfortable conversation about saying like. All right. If we do this company and we know how big it can, could [00:46:00] potentially get, there's gonna be sacrifices. And that's gonna be the three kids, right? There's, they're not, we're not, I'm not.
And he's not gonna be able to be a hundred percent at home, like, and a hundred percent there for the kids.
Live Cam A: Hmm.
Kass: And so we had this kind of calculation and people are always like, I can't believe you talk about this, but like, we had a calculation and I, I said, look, big kids, big problems. If we can get back when middle school happens, when people are mean, when you know all the big issues that start to happen, that will be better for us.
And so we went all in. And so it didn't mean that I was at zero with my kids. And that's the difference is that I was probably at 80% right in terms of how present I was and how, um, how much I had to offer, which 80%. Now my kids are 23, our kids are 23, 21, and 18, and they don't. They don't see, like we weren't there at all.
They, they have no memory of this, which is kind of awesome, but I, there is no balance. As an [00:47:00] entrepreneur, if you wanna do something, well, whatever that is, you can only do one thing well at a time. That's my, my philosophy and for any of the mom entrepreneurs out there, gotta give yourself some grace because 80% is usually from a mom is like a thousand percent for most people.
David: Hmm. There, there was actually a quote that I pulled that said, um, an entrepreneur's personal life inevitably conflicts with the endless stream of work. There is no off switch, no quiet, quitting, no balance. There's only an effort to manage the imbalance Yeah. As effectively as you can.
Kass: Yeah. You like, we didn't have a lot of friends outside the company.
We didn't when everybody's like at preschool and they're all meeting and having play dates, I was like, oh my God, I have no idea who these people are. Right. That was just not what I was doing. And when people went away on vacations together or had picnics in Central Park, which I never did either, like I had no idea.
There's a, there's a part in the book [00:48:00] where we were in due diligence. It was three months with Salesforce and due diligence. That was super fun, and two of the three kids started a new school and we got there. And it was lower school. And the principal comes out and says like, okay, like this is great. Now you'll see your teacher with a flagpole for your classroom and just take your kid over, introduce yourselves and drop them off.
And I look at him and he's looking at me and he's like, wait, you don't know. And I'm like, you don't know either. Like, we had no idea who the teacher's kids were zero. And so we kind of just like shopped them around, like Lazar rose here, and eventually they pulled us over.
David: Yeah. Um, we're going to, we're gonna, I'm going to the last couple questions, but we're gonna, uh, take questions from the audience, um, in a, in a second.
Um, so, uh, knowing, uh, we'll start with you, Mike. Knowing everything that you know today and all the experience you've had and all the companies that you've [00:49:00] seen and everything, what is the one piece of advice you would go back and give yourself at the very beginning of your career?
Mike: I mean, really good question.
The. I wasted a lot of time and the focus thing is really hard and I think we could have worked faster, better accomplished more early on if we really knew how to focus an organization. Like it's the number one thing, and I don't, I talked about it earlier. It is the difference between survival and not.
It's the difference between being a billion dollar company versus a hundred million dollar company. A lot of companies succeed but they don't even really know why. Right? Like product market fit is this like nebulous thing. When you really focus, a lot of good things happen and the best thing that happens is you actually, by working smarter, you're able to [00:50:00] open up time for other things in your life.
Not a lot, but I somehow have gone fish.
Live Cam A: Yeah.
Mike: Yeah, some have gone to like over 200 fish shows, 2
Kass: 28, but,
Mike: but like you can work smart and it doesn't have to be as miserable as maybe we made it and ask yourself, are you focused on the right things today? Because being successful is doing the right thing every day and turning into a good week, a good month, a good quarter, a good year, and in many cases, like decades, many years.
Yeah. Like if you do the same thing for many years, you will succeed. Like time is such a great thing and if you don't do the right things and you're just wasting time, you don't get that benefit of compounding the time and growth.
David: Yeah, I think, I think that's amazing advice. [00:51:00] That's number one from, yeah, there are
Mike: many others, but that's definitely number one.
Well, and
David: I think, again, as entrepreneurs, as founders, it's hard to focus because of all the shiny objects that we see every day. But I think especially if the team gets bigger, you, your lack of focus just cascades into the rest of the org, like you said before, and then it just derails everything.
Mike: And the other thing which comes close is Kass hired a, uh, executive coach, I don't know if you know Tammy Jersey.
Um, and her first thing is she did a one eight, a 360 review. And she talked to all my direct reports. And like, if you read that now, you'd be like, this is the worst leader I've ever like met. I was distracted, I was distracting, I was getting in the way. I wasn't listening. I was going to meetings and trying just to get my ideas through versus listening right.
And like people who disagree, they weren't disagreeing with me, but the idea, right. I couldn't separate the [00:52:00] two. And so I would've gotten that coach earlier and I would encourage everyone to basically build infrastructure that will like punch your ego in the face and be really like, it's hard. It was hard for Cas.
Can't can't, I don't think it, I don't think Kass, she's delivered some hard news over the years, but that would've been difficult I think. So she like, I
Kass: think he wouldn't have listened to it as well. Yeah.
Mike: So she like manufactured this woman. I guess I would've found her. So I, I would do that. And that was one of the most important gifts I ever got.
'cause I think I became a better listener.
Live Cam A: Mm.
Mike: I became a more empathetic leader and husband. Part of the book is, oh yeah. Part of the book is not just the cheat codes to build a business that transcends kind of. Your wildest dreams in your life, but a life that really transcends any expectations that you had, right?
Because as an entrepreneur, there is no [00:53:00] difference between like your work and your life, like your identities, that you're basically inviting people to watch you fail in public. I mean, once you say, oh yeah, I got this company, it's like, okay, what happened to your company? Oh, we went outta business or ends up in the news, right?
Mm-hmm. And so, um it's a, this is the biggest gift I was given, being able to be independent and do this. And that's where we find like the passion and purpose of our life.
Kass, how about you?
Kass: I would say two things. I would say I was one of those kids that got outta college with an economics major like that did nothing and had no idea what I was supposed to do, right.
And IKI took the advice of my dad. He said, you have strengths. Focus on your strengths and then apply them to as many different jobs until you find one that [00:54:00] makes you move for a little bit further. Mm-hmm. And so I think if I just, I, I, I took it, but I didn't, I didn't, I kept having anxiety about that. And so I, that's why I go around talking to kids all the time, college kids, to, to say like, follow your talent, follow your strengths, and then just try on different jobs.
That's the first thing. And the second thing is kids are gonna be okay, is totally okay to be super passionate and driven as a mom, and they will be okay. Because now I have three kids who are super passionate, hardworking, and driven.
Mike: Maybe they were better 'cause we weren't around
Kass: probably as I think about it, probably that as a feature, not a bug.
David: Alright, we're gonna open up to questions. Um, Nick, you have the mic. Okay. Where do you wanna start? Anyone? Casey?
Live Cam A: Hello. Thank you. Hi. What were your favorite cult [00:55:00] activities? Good question.
Kass: Are you, do you need the cult activities that I would do today or from the past when everybody showed up to an office?
Live Cam A: Yes,
Kass: that passed?
Live Cam A: Yes.
Kass: Okay.
Live Cam A: And present. Okay. I'll give
Kass: you, I'll give you all of them. So I think. You have to, like any activity that has your thought and your ingredients of your mission and values and like your moral compass in it is helpful.
So like we did, um, kickball game and you know, it's kind of an equalizing sport. Probably I'd change it to pickleball now, but, um, most people can kick, I mean, mine didn't go very far, but every quarter we did some kind of equalizing thing. But the big part was we always had a charitable act after. So we made, like when we were 150 people, we made 10,000 sandwiches.
And I didn't just have people come pick 'em up. I made everybody, I had to really push for this 'cause they were worried. It wasn't [00:56:00] sanitized push to walk them over by hand. Right? So making people feel things, right. The what you wanna feel like what that like, think about. In your childhood, what were some of the team environments?
It could be with your family or it could be a group of friends or a club or sorority, fraternity. And were there moments that you felt just, it just was everything was in sync and you loved it. That's how you have to make your cult. That's how you have to put the ingredients in remote world. I would,
Mike: but talk about specifics.
So like we celebrated with cupcakes. Everyone likes cupcakes. Are you
Kass: taking my thunder?
Mike: Yeah. They want like, no, no, no. She filled up an office with balloons. You're talking like literally you'd walk out and it was like balloons everywhere on their, their anniversary. So like
Kass: effort matters from—the small things—the founders effort. Every time there was a birthday, I didn't care. We got up to 370 we wrote handwritten notes. It wasn't somebody else writing them handwritten notes. Happy birthday. Here's a Starbucks gift card, right? [00:57:00] So there was a lot of intention, and I hear so many founders saying, I don't have time for it.
it's not gonna matter. Handwritten touches absolutely matter. So
Mike: Bob the Bobblehead,
Kass: well that's a different story though, but basically like. I, I would hire and fire people within 30 to 45 days. I just knew whether they were gonna be able to pivot to a different role or we hired them in the wrong role, or if they could actually keep up the pace.
So if you made it through a year, I gave you a big present, like something that was uber expensive because you made it, you were a deal maker, right? So we had custom bobbleheads that look like you, and these were just, they're so great. I still have mine, massive badges of honor and, and goofy stuff like that in the remote world where we are, and I tell every portfolio company this, where is your budget as founders and leadership team to travel to see everybody?
If you can't come all in right, twice a year, at least, if not four times a year, you should [00:58:00] be going to the hubs and doing these things. They don't take much, right? I mean, I, these zoom happy hours and the games you're playing that does nothing. Absolutely
Mike: nothing. But part of like part of a cult.
Is like symbols. Mm-hmm. And stories and traditions. And so doing the quarterly meetings, everyone knew they had to be there
Kass: and they couldn't miss 'em.
Mike: Seeing a bobblehead became almost a religious artifact.
Live Cam A: Yeah.
Mike: You know, like cupcakes became like a thing. That's why I also wasn't very healthy at the time 'cause I was eating with clients and not working out.
And also
Kass: we, the other thing is about like the positive cult, and I think founders forget this and almost we sometimes forget it. You have to celebrate the wins. It's really easy to forget to do that and just push to the next goal and be like, awesome, we did it. Let's go. And [00:59:00] you have to stop and celebrate the wins with the team and make it intentional.
And maybe that's free food or maybe that's, I don't know, the spa day for whomever did the thing. And we did spot bonuses a lot. We thought that was really helpful. I also really called people out in big meetings. That's only for people like
Mike: money though.
Kass: Yeah, of course. But like, I called people out a lot in meetings for little things, like, Hey I was over here and I saw this happen.
And that was awesome.
David: you had a question. Yeah. So there's, there's the mic.
Live Cam A: Hey there, Anthony. Um, UCCI. So shoveling shit. How much did, did you debate the title? How long did it take to, to settle on it and were you worried about the. Curse word and Amazon and the whole world pushing against it.
Kass: Well, we had thought first it would be entrepr manure, but it was taken and there was a company in London that was suing. I don't know how they could sue [01:00:00] across, but there were suing companies in the US that was using any alternate word with entrepreneur in it. So it was a really big bummer for me. 'cause I thought that was really good.
And Mike had kind of come up with that a long time ago, at least in the us And then we kept like debating and then we just, like, we couldn't think of anything else. 'cause this is all you do. I mean, it could have been like punched in the face every day, but, but I didn't think that was like
Mike: perfect. But we did debate like
Kass: shit,
Mike: do we want to go there?
Like probably it won't hurt us. Yeah. We won't get the lists because of it.
Kass: And, and we can't get ads bec we can't, we can't run ads
Mike: on Amazon. We're doing podcasts where they're, I don't think, like, I don't even think they're looking at it before they have us on board. Then they're like, oh, shoveling, bleep, bleep.
We're like, but at the end of the day, we, we felt that it was an honor, like we were [01:01:00] honoring entrepreneurs. Not like shining the turd, sugarcoating it. A big part of the book, like one of the lessons is don't shine the turd. Right. And once we figured out the title, we went all in. There's like poo poo on the poo poo on the cover.
Mm-hmm. Well, we got kids here. Um, but like, you know, you see the cover and it's like, first we're like, well, do we want it on people's tables while, don't we? No. And I was like, no, this is, now we're like all in, it's gonna be
Kass: epic. You're gonna put this and let's put
Mike: it even like the poo from your hand gets on the cover.
It's like, and then cast. They planned an amazing event at the New York Sake Exchange, which was for those who were there. And you know, we, I see some of our community here. It felt like a Buddy Media event. It was like warm and personable and everyone felt recognized. And um, she had giant covers, like book covers with holes that you had to throw toy plastic poop p through [01:02:00] to get prizes, right?
So once we went there, we went all, yeah,
Kass: every entrepreneur got a gift 'cause we wanted to celebrate them. So goes back to culture, gifts matter.
Live Cam A: So first of all, thank you for that. It all resonates so much. I'm also just started my second start with my spouse, so, woo. It hits, there we go. Uh, a quick question about the hiring and firing fast. Yeah. How do you know to differentiate between a situation when. An employee doesn't perform well, but maybe it's time to coach them, mentor them, versus it's really time to help them.
How, how many employees do you have now? So currently, because we're early stage, it's just us three co-founders.
Kass: Okay.
Live Cam A: Previously, I had around 20
Kass: employees, so it's gonna be in the, in the beginning, like from zero to 25 ish employees, you don't have time to coach, you just don't have time. So you've got one shot, you can move them to another position, or you have to get rid of them.
You [01:03:00] cannot spend your time. That would be like at 500 people interviewing everybody. You do not have time. So you need someone who's gonna hit the ground running, wear multiple hats. If, if they do, if you feel like something's not working you, first of all, a, you probably hired the wrong person to put 'em in the wrong position.
Right. You do not have time to do that. When you have managers, then you have time to actually sit and coach and mentor for a bit. But again, you're, you gotta get to profitability.
Mike: There's also this concept that one of our founder CEOs shared who happened to win seven Super Bowls, um, that the best teammates are ones you don't worry about.
And with 20 employees, you're basically a team, right? Like you're traveling together, you're like tight. And the best teammates in sports, like they're practicing they know the plays, you don't worry about them. Like you, he's a quarterback. And he just [01:04:00] knew that Gronkowski was like gonna be in the right spot.
Other teammates, he was always worried, oh, he's gonna screw up the play. He's not gonna know it. And so like, that's the problem early. You're like, you're in a meeting, hey, I need you to do this. Or he, he or she agrees to do it. And then you come back and it's not done and they're out and you're like,
Kass: Ugh. In the beginning, they're out.
It just
Mike: like takes down the whole organization early. Thank you.
Live Cam A: Hello. Hi. Can't wait to read the book. Sounds really good. I'm, uh, also, uh, working with my wife for 10 years. This is awesome. Love that. This is super proud. And recently we started, uh, I started a, a startup, but I realized after a bad experience with another, uh, co-founder, uh, that my wife is my Venus and, uh, she's probably the best co-founder, but we are, we have concerns because we're raising three kids.
The fourth is [01:05:00] on the way.
Kass: Congrats.
Live Cam A: Thank you. Um, so
Kass: you're concerned about.
Live Cam A: What you don't do, what you absolutely, absolutely don't do when it comes to personal relations in front of other people in the company,
Kass: what you don't do, meaning like, do, are we, are we sharing everything with like how
Live Cam A: you prevent, uh, fighting in front of others?
I mean,
Kass: honestly, like, we don't, we didn't, I mean, look, we, so we all out
Mike: there. I mean, Dina works with us, like we're very aggressive.
Kass: I, I'm, I will say like, I think you're, you think it was
Mike: uncomfortable to start, but it's just how we are. Like,
Kass: I don't, we don't, like, we learned a language of just radical honesty and so we just look, I mean, maybe the kids at work got nervous, but they saw us coming back over and over again.
I, I think you have to be exactly who you are at all times and decrease the space between you and a team. I think that's the only way [01:06:00] to move forward. And you have a unique opportunity to show a superpower of how you both get along and have this amazing family on the side. Right. And you can lead a team through things as well, and you can use those skills and kind of exchange them.
So I wouldn't try to be different personas. I, if you fight, I mean, I would say that's the stupidest idea I've ever heard. And it also gives people, um, the permission to also be honest, which is what you also want. Does that help? Absolutely. Okay.
Mike: And, and I'd love, do you mentor
Kass: couples? Yes, we do. We would, yes.
Mike: What I, what I love about couples working together is there's no option to fail. You're in it together. Yeah. Right. There's no, like someone has a high paying job and this is another one's just trying to make it work. You have a shared life. That you can change your future generations [01:07:00] by like succeeding, right?
By working smart, by creating wealth.
Kass: And you also have the best support system in each other because you know exactly what's happening and you don't have to make excuses about why you didn't show up for X, Y, and Z.
Live Cam A: Hi. Um, I'm known as Coach kj. Um, sorry. No. Um, I have a another couple of questions, so you, you might be onto something. Um, I was just wondering how it, uh, is it difficult to like, navigate, uh, just the personal relationship with the business? Uh, just having somebody that your business partners with?
Kass: Well, Mike had this thing when we started all of our companies together, that we went on date nights, on Wednesdays and Saturdays as soon as we could afford a babysitter, even if we didn't go out.
So it was like time for us and we made it like we didn't miss it. You know, like we've missed a couple times 'cause I think of book events, but we just [01:08:00] didn't miss it. And yes, we talked about work some of the time, but we then also talked about our family and like things we were looking forward to. But the other thing that we did is we had things that we did together that wasn't work.
And so for the people who don't have their spouse as their co-founder, you have things you do together. Well, we did too, and we still do. So we really focus on that, if that helps. Thank you. Yeah.
David: Last one. Last one for Sammy. Sammy,
Live Cam A: what would you consider success? In like a company?
Kass: Really, really good question. Uh, so I think you can define it. For me. I had a very different [01:09:00] look of success than I think Mike, and Mike was really focused on numbers, right? Revenue and profitability. But for me, I was looking at how many people could belly laugh in a day and show up the next day and, and do it again.
So I was tracking like just, were people authentic and could we, could we make fun of ourselves? Could we, could we have a good environment? That was success for me. If I could create a team that could laugh together and show up for each other,
Mike: I think at the end of the day, the best companies. Solve a real problem for their customers.
So you could take everything from Apple, right? They help us communicate to what's your favorite company?
I don't know. Are you a Nintendo [01:10:00] player? You Minecraft, PS five. Yeah. So like life is so, what's that problem, right? Life can get boring. That solves boredom. It's fun,
Kass: it's entertainment. And
Mike: so if you could create something that impacts one person's life in a positive way, there're probably more people like that.
Whether you're a restaurant, right? Like I like pizza, so like there've been a lot of pizza places that have impact my life positively and negatively. Um, and that at the end of the day, businesses have to be. In service to their customers. And if you're not, you're not gonna be around.
Kass: And that's why we pivoted three times is Yeah,
Mike: we changed because we, no one cared what we did like until they
Kass: did, until they did.
Good question.
Mike: And there's no one better than your pops at this, right? Like the cloud space was really [01:11:00] like companies trying to manage all these apps and it wasn't until better cloud that they could actually do it from a centralized area. So that was a real pain point.
David: Thank you, um, cast. Mike. Thank you.
Really? This, this was amazing.
Thank you. Thank you everyone for coming. Alright, we're done. Is that a wrap? Thanks. Thank you. Appreciate it.
[01:12:00]
Share this post