the focus isn't on me, the focus is on the entrepreneurs or building communities or helping and that's

just such a

much better place

to be. You get punched in the face enough times you learn how to dodge, that's how I feel as an entrepreneur,

isn't it? Is it Mike Tyson, the one that says, you know, everybody has a plan until they get punched in

the face. Yeah, thank you to a vast for supporting business envy with a vast one. That's a vast one. You can confidently take control of your online world by helping you stay safe from viruses, phishing attacks, ransomware, hacking attempts and cybercrimes learn more about a vast one at a vast dot com. That's a V A S T dot com. The illuminati are real, That's a great way to get the right away, let's just start it off right away. Get people excited, people are like what? This is not what I bargained for. If you're just chiming in, if you're just perusing and business NV with something that you wanted to click on and listen to.

I am Greg Grunberg, I've been an actor for oh my gosh, it seems like 100 years. Um and I met a guy years ago Ben, you interviewed me, Let's just let's just talk very the elevator version of how this whole thing started. I was the editor, the co editor and editor at large of Mashable, the big tech news website and this was in the beginning of my career and I think your pr team was like, you know this actor Greg who you may have seen in Heroes has a new app called Yowza and you want to interview him is like hell yeah, I want to interview him. It was a mobile coupon app that I created with two other brilliant guys and we were in the phase of just trying to acquire people to download it, trying to get companies to list their coupons and it was it was the the app was stupid simple. I wanted to just make we decided that you know you hit a button, it geo locates where you are. You can build that fence as far or as close to you as possible and it brings up all the coupons around you,

you click on the coupon, barcode comes up, you scan at the register, you're on your way. It wasn't as simple back then as it would be today but we were so fortunate to be on your show. But in that conversation I remember in the bay Yeah we started coming up with like another idea in the middle of our interview and so after the interview was done we stayed on to talk about like the concept we started talking about, we just talk about it. Well was it zoom that we were on first of all on there was no back then it was it was use it was you stream. I remember it was you stream. We all screamed ice cream, that's what it was you stream which was just that that lets you know how long ago this was. But I remember you had a really interesting office, I was at home but you, you had a few things in back of you and one thing was blinking and because that thing was blinking, I was like, oh what is that?

I remember I got it from one of those like geek websites and it was like, it like had the lightning bolts and things going around. Yeah, yeah, yeah, yeah, so we had no, it was, it was based on your voice, it would react, it would react. And we started coming up with an idea of what if we could do some of those same kinds of things in a mobile app, which we'll talk about in a future episode, like but that spark, we decided right then and there, I mean here's two guys that don't know each other,

I was loving what you were doing, you were at the forefront of what you were doing and I thought, wait a minute, this is a really smart guy and and this, this just goes to the entrepreneurial spirit of taking a chance, don't worry about where and who you meet at that given time. If two people just have this sort of lightning moment and go wait a minute and you both get it, don't you agree, like it's all about taking the reins driving that train and there were two guys in the front of the train, You and I were both so excited about it, We're gonna be, we're gonna ask this kind of question to our guests about that lucky moment because it was like that like I had the thing in my frame for you to see and frankly like that like we got connected to do the interview but as a result of that now we have a decade old plus friendship and now we've started this show and and many other business ideas in particular because we want to succeed with whatever thing we do next. And we've been talking about different startup ideas and every time, every time I ask you about an idea, do you think this is a good one? How do I best do this?

Can we do this together? I always try and rope you into these business ideas you call me on, you know, whatever. We, we just, we always lean on each other which is awesome and my friendship is worth more than anything, any company that we would create, but I have to say um what I love about this opportunity now is we were like, look, we're having these conversations already. You always reference the most incredible entrepreneurs and finance people and business people that you know, let's bring them on the show, let's talk the conversations we've been having for years. We now have in this podcast, business envy.

Every time you talk I'm envious of your success, their success, you're envious of the friends that I have like yeah, I want to learn more about you, your business like Hollywood. Like there's some super successful people who've built huge both like personal and business empires. There's so much that you and I and the audience, we all have to learn from all of these people and that's what we're trying to do here. This is business um time for our guest um you mentioned this person's name to me, tell everybody about this guest, Greg, I've got someone really special for us. What's so special about this guy? He is the man who made me, who I am, he is my mentor.

He taught me everything I know on entrepreneurship and more than anything. He is just a good guy, a good human. He, I worked on a facebook app company with him, I worked at a web health company with him. He is also one of the most successful venture capitalists in Chicago and founded and was the ceo of one of the most important tech companies in the early days and I'll let him talk about it and he just came out with a book specifically for founders on how to sell their companies because he has so much experience with that and so he's been on book tour and I'm really glad that we were able to snag him because he's been very popular recently as a result. Well clearly he's not in Hollywood. If he's a good guy, I can't wait to

meet him.

Mark your face just got really uncomfortably big. Um You have a face. Okay so let's start now because I want to just comment on your face. You have a face that I want to be in business with. I want to trust. I know you're just a ruthless tyrant. You're a business guy that just takes advantage of everybody you meet. No but you really have a wonderful face. I hope your kids and everybody in your life looks that way.

I don't know. How do you how do you respond to that?

My face is excellent. Thank you so much. Beautiful cream. You definitely moisturize. That's for sure.

So definitely moisturize. So it's funny you should say that because yesterday I was teaching a class at northwestern at Kellogg to 25 leaders from 25 different African countries and at the end of the class one of the somebody came up to me and said you are the kindest most um like you just have to exude kindness. Sounds like that's two days in a row. Is it really? You

know what kind of that is I mean? And I've and I'm not patting myself on the back but I've heard that the characters you play very similar to who you are, whatever it is. That's got to be one of the best compliment someone could possibly

give. You. Don't you think. Yeah of

course. Yeah. To be clear everyone, this is the first time Greg and Mark have ever met each other. Mark and I have known each other for, oh well over a decade as market. When I'll let Mark, you have to introduce yourself. We call it the origin story, we want to hear your origin story, but to give some quick context, Mark is my mentor, you know, Mark and his business partner Troy Hynek off, taught me entrepreneurship and my first job out of college was working for Mark and so he's had an incredible career that I can't even go enlist. So I'll let him go and do that teaching someone entrepreneurship when someone says, what do you do you say? I'm an entrepreneur? I just, it is such a bullshit term, I look at it and I go,

what does that mean? It's

so vast. I I understand it now from my experience, but don't you, you know, it's like, is that specific? Like, I'm gonna teach you how to be an entrepreneur. It's it's a very, you know what I'm saying? It's it's a tough,

yeah, it's really tough. You're absolutely right because it's such a broad topic, but but there are skills like empathy, right? Their skills in terms of listening, learning, listening to your customers, learning about your partners uh problem solving integrity. Talking about values, We don't talk enough about values and integrity in business, which I think is really important um a sense of humor, having fun. There's lots, it's a huge canvas and there's actually a lot of life skills that we can be that we can talk about in that canvas.

That's so true by the way, from my world, I'm an actor. I've been an actor forever. And um, you look at the director and there are specific skills, technical skills, you need to know how am I gonna get the shot. But it all comes down to your people skills if you cannot communicate to your crew or to the other actor and get the emotion you want from them and by the way, be a

sniper, be, you

know, economic with your words, if you go on and on, I'm sure it's the same in business. And I found that in business, in my limited experience, if you're going on and on and on and people just get lost. But then there's also being too specific and, and just, you know, um, I get in this mode where I'm in and you might have this, you get home and you, you have to switch off, you have to be in family mode, you can't be in. So this is what I want and get, you gotta be, it's, it's a whole different way of acting and there's a balance I think between the two, don't you?

Oh of course, of course. But you know, it's at the end of the day, I have a framework that I use sort of how I manage my life. And and it's um joyful innovation. So what I really care about is not only innovation, but it should be fun. Like it is difficult and hard as life is and it is right. Um, but it should be fun and building communities. I think it's like it's really important where our brother's keeper that building communities is a really important aspect and of how I incorporate in my life and teaching empathy and and listening skills and I do that through I do that through helping all the work I do helping entrepreneurs and investing entrepreneurs and my teaching at Northwestern and other places and all the non profit work I do and sitting on boards and, and I think the nonprofit part of the world is really an important aspect of giving back. And so yeah, it's a blend.

Do you have a lot of this stuff in your new book? Is this, do you touch on that? We gotta go into your background because there's a lot to cover here. Yeah. So let's do that. How did you guys meet you tell the story?

Well, how do we meet? I think we met through Troy. Didn't we

meet through Troy through your business partner Troy, Hynek off, who ran texas Chicago and co founded Math Venture partners with you.

Right. Well, and also I was his lead investor and chairman of the board of Sure payroll. His first one of his companies, that's how Troy and I met. So Ben, I think you were a student of Troyes and Troy and I were starting were doing were messing around on facebook first, right when the first opened up and you were still a student and we got to you as an intern and you were helping us launch a couple of facebook apps. And then when you graduated, I brought you into a company

I was running. That's awesome. Yeah, there's, there's just a side, there's facebook app was called Friend Quilts and you could like upload photos and create mosaics in the early facebook app days and for people using it and it was cool. But as I have learned over time, you gotta be careful when platforms changed the rules. Now, the way I look at your face and I trust you, how did you trust that face? Ben's face? I would be extremely weary of, Well,

you know, this is where the age differential. Like I became a father figure in a sense. And you know, we worked together and I got to know Ben and Ben is, is just such an incredible human being. And and so to give you Ben, you've asked me a couple of times, so my origin story is I'm a tech guy. I I started one of the very first computer retail stores in the country with my father back in 1981

and

it's called computers, et cetera. It was a retail store and we built it up and turned very successful and I became good friends with the Apple guys and I got a job offer to go to Apple. So I was the worldwide introduction manager for the Apple to see a long time ago and I had a chance to work with steve jobs back in the day and I have some great steve jobs stories maybe for

another time. And

I came back to Chicago because I had just gotten married and we were this year, a couple months from now, we're celebrating our 40th wedding anniversary.

Congratulations. I'm at 30 years, 40 years. You're the Joey chestnut of marriage,

just throw another hot dog down.

Congratulations, that's fantastic.

Yeah, thanks. Yeah, my wife has put up with me for 40 years but my wife didn't like California and she said if you want to stay married to me I'm gonna be in Chicago because she came from a large jewish family in Chicago, you know, it's like she, all her friends and family were there and I went, okay. So I came back to Chicago because family comes first and I became an entrepreneur and I started four different companies. The first one did, okay. We built the second product ever for Windows one dot. Oh and I built that up and sold it and took in venture capital before there was any venture capital industry. This was 1987. And then my second company was um an educational software company that failed miserably. And one of the things that we don't talk about a lot in these kinds of conversations is failure. Uh, and that's, you know, I have a lot of scar tissue. I've made a ton of

mistakes. Don't you think that that's true of any successful entrepreneur though? I really believe that it's, you, you have to be willing to fail and learn from your mistakes and move on.

Yeah, that's absolutely right. And you know, I have an insane tolerance for risk. And I talked, I talked to entrepreneurs all the time and talk about co founders. Like my wife, she had the same, her dad had the same job for his entire life. She if if if if I had the same job for my whole life, she would have been thrilled. I put her through misery. You know, just the, it was very hard for her because me, I love risk, I love starting something new.

I'm gonna, I'm an innovation junkie. But but you know, not all, not everybody has the same level of risk conference. And that second company failed and started a third company, which I got very lucky and it did, it did very well and we became Softbank's second acquisition in the United States, which gave me the freedom and the flexibility to become to start a venture capital fund. So in the dot com days I started my own venture fund with a couple of partners and that did great fun one was a lot of fun. We had some companies go public fun too. We closed in january of 2000 right before the dot com crash. That wasn't so much fun. And, and I'm proud to say that 13 years later we were in the top quartile of venture funds of that vintage, which meant nothing other than we got our lps their money back.

Just say I like calling venture funds like a vintage, like a wine, like It's like a nine, it's a 2000 vintage venture fund to it.

It was,

it was the best of the bad year.

And then then I went back and became an entrepreneur and I started, I helped co found healthcare educational software company. She did great and ended up being a very big success. And then I took a job when I was 50 years old. I became the chief innovation officer of red box. Red box, the movie. Of course,

Yes. So wait, where was red box in? Uh, because you literally look 30. So when you say 50, I don't know how long ago that was. So when

I'm 64,

no way.

Are you kidding

me? I mean people that are listening to this and not looking at that face, I can't honestly, what do you do? What is, what is, what do you, is it ranch dressing that you lubricate yourself? What is going on? Thank you all for tuning into skin. Oh my god sorry to be such a fan of your face. But my god maybe we should have dinner

But you know so my joke is it's okay so it's nice now. I know I know I look much younger than my age but when it really mattered, when I was in high school I looked like

I was 10 years old

that I couldn't get a girl to look at me if my life

depended on i with all your success I bet you still have a fake I. D I let me ask you where

was like

that's what I'm saying. But let me ask you where was red box because like my view of red box, I look at red box and I go okay outside of 7 11 there was this red box and you would get the video and you return it it's sort of and now red boxes from what I understand just

massive.

Oh it's

gone. No no it you know over the court it was massive at its height. So I was part of the early days of red box and I left in 13 I left beginning of 13 so almost 10 years ago and um in its day over one third of all U. S. Households rented a movie from Redbox. Oh wait wait wait I have a great alright I have a great trivia question this this is a great trivia question for you which is between 2005 and 2015 if you think of every single movie ever made in that time period, what was the number one best rented movie? Remember one third of all U. S. Households? So we're talking about 80 million rentals a month. What was the number one best rented movie in red box in that time period?

I my immediate instinct is to go to something that families would rent like a deep

throat. That's a good that's a

good right. It is a good instinct. Okay so um wow. Is it is it an was it a was it a contemporary title or was it something that animated animated some some old

and you know like I'll cut to the chase. Okay. You want to know America if you want to understand why we are, where we are today.

A great title,

paul blart Mulk,

that's incredible,

paul blart mall cop was the number one best rented movie. Think of every black buster of Oscar winner Disney. Right. Star Wars. Right,

incredible. I'm sorry you're not my god. And number two was Ernest goes to camp, that's what we're talking. That's crazy. Now wasn't red box going to start doing the sort of netflix model of creating their own content? And have they done that? Did you do that back then or did you see the cliff and said I'm getting out of here.

Well you

know it's a Big boys

game, right? And it takes a lot of money. And so the challenge for a red box. Uh and this is really interesting from a business perspective if red box was bought by a company called coin star and The coin star board of directors, very old school slow growth, you know, red box went from like from 100 million to 300 million to a billion to two billion. You know, red box was just going through the roof but coin star was growing 5% a year and the board of directors a coin star, it became clear, you know we're talking 9 4010 that streaming was eventually gonna win, right? The world was going digital. It hasn't quite happened yet but it was heading in that direction and in order to compete, he was gonna require billions of dollars. And the red box board of directors made the strategic decision.

It's like look we could either go spend, you know go raise and spend billions of dollars and try to compete or we can milk it. We could just, you know sort of take a step back and that's what they did. They they decided strategically that they it was a big boys game and that they were these machines were incredibly profitable and they just melt, they melt it for a decade.

Yeah. Yeah it's interesting because you could you could see the progression from blockbuster two red box to netflix. Netflix and Redbox we're having at the same time, right? But but netflix, you were sending it in, you would have to mail it in this, it's just to watch this industry and to see and to think where it's going now. I mean, I never thought that I would have and I'm jumping ahead, but in the streaming world to have so many subscriptions to so many things. Last night I bought, I bought stars, I was like, I don't need stars, there's nothing on Starz. And my wife was like,

I really want to see this show. And so you were doing like, like the shows were like, see we're like, you're doing shows for like NBC and things and now it's like HBO max and netflix and app. Yeah, I mean, it's a great time for me being a face that people recognize and say I want to put this guy, there's so many opportunities for actors, you know, it's just it's all over the place. There's so many streamers, so many creative channels, but it's just it's just it's the Wild West, you know, and uh and I think people are paying for libraries and the and the potential future show, obviously it's it's the same,

you know, but there's a challenge and and this is a difference between search and curation, there's something I call the tyranny of choice. What's great for you is there's an explosion of content and that's wonderful for as an actor. I mean, that's incredible. But from the end user's perspective, we, you know, people don't want, here's the interesting thing about red box versus netflix versus black buster. Remember black buster, you walked into a black buster store and there was row after row after row of movies and you thought to yourself, ah this is awesome. I get choice. I get every movie ever made. But it turns out that over 90% of the rentals at Blockbuster,

We're from the 30 day wall with new releases that even though people thought they wanted um choice, what they really want was the new releases. And even then what they really wanted, they didn't want every new release if you like sci fi or you like westerns or you like romance. Like you like a genre or if you like a particular actor, right? You want. There's actually a fairly narrow window. You just said, your wife goes, I want this show, I want this actor, right? And so where we the choices almost is too much. And what's really interesting is there needs to we need to go back my perception is that the trusted editorial voice that curates that knows who you are, knows who you like,

who can recommend because, you know, Ben, you talked about NBC, I heard you say NBC, you know, when I was a kid, there was three choices, there was abc. NBC Cbs.

It Me

too, right? And they were they curated they, they were the editorial voice like you like, okay, they picked for us now, you know, I could do without Gilligan's Island.

I mean, I have no idea what that is, but that's, but isn't that what, that's what amazon does? People that like this like this, you know, it's that, it's that, that algorithm thing. But um, but I agree with you, I walk into 31 flavors and I'm overwhelmed. I mean, I, I want, you know, I want the best of the best, tell me what's great right now and let me try it and let me,

let me taste it. Yeah. Anyway, so I don't know how we got off of that, but to finish off. So after red box, I started a new venture capital fund and that's what I do today is I'd like to say, I make entrepreneurs dreams come true. I

love it. I have, I have a question about failure because you brought it up and I think it's just fascinating. What hard and fast rules do you have now with all your experience when you're backing a company, when you're working with a company, a startup, at what point do you say? We are kicking a dead horse. It is not working. I mean, I know it's different for every company, but is there something where you go, look if we're not profitable in three years guys, there's something wrong here.

Yeah. You know, it does vary by company and it varies by founder. Um, you know, I call it the elephant in the room, which is the hard conversation, you know, let's really be honest with one another. Oftentimes that as companies start to run out of cash and run out of money and there's a new round of funding, there's that, that moment of truth where the investors are looking at each other and the founder in the eye and going,

yeah,

you know, I, this puppy

might be done right or do we pivot? Is there a better use for our technology or whatever? It is interesting being on the other side of different kinds of moments like that. I've had to be in that moment where like looking at like we're not getting anywhere. We don't want to like waste more people's like money, like we wanna, like this is not going to go and work. We could try to pivot, it won't work versus other times you're like, we're making real money, like we have to make this survive at all costs and it's a hard decision depending on what stage you're at, what place you're at. You know, the stakeholders. Yeah, everybody at the table is, is in a,

in a different position to have a different opinion on that because there, this is my only, I have nothing else, this is it. And I, this was from a seed of an idea and a passion, passion is what kept me going, I'm fine if you don't want to invest, I'll find more money somewhere else. It blinds you to the fact that the company just isn't working well.

I'll tell you an interesting story about that. So I have a saying which is all entrepreneurs have to be tenacious as hell. Like we just have to knock down walls. We have to be persistent but persistence without empathy is kind of like a mental illness like like just doing the same thing over and over again and expecting different results. Right? So one of my last company was a health care company and we did do the short version. We did patient education tied to risk management. So we we imagine the process of informed consent, informed consent is you're going into the hospital for a surgical procedure, your drips in your arm, a nurse shoves a form in your face and says sign and all it is is a waiver of liability. It's supposed to inform you and it's supposed to be a waiver of liability and it doesn't neither like it's loyally gobbledygook. Nobody lawyers don't even understand it and if you want to see what you're gonna do. So we were game developers and we decided to take game methodology and create a user experience that was loving and friendly and fun and apply it to educating patients about what they're about to go through and explain to them all the risks and document that. And so patients are better educated comply better with instructions and can't say, I didn't know no one ever told me. And we thought that our customer was a doctor and we went to try to sell one doctor at a time like shoot me,

want to try to sell one doctor at a time and we were almost at death's door and we're not too smart. And all of a sudden we realized, oh, it's like two years in when there's a malpractice lawsuit, it's actually the insurance company that pays for it. Oh so we went to the malpractice insurance company. They loved it. They went to other doctors, they said this is great. We want you to use it and we believe in it so much that we're gonna give you a discount off your medical malpractice insurance premiums equal to the cost of the software. And we went, yeah,

it's incredible.

Now then guess how many we sold.

Oh no,

maybe like five.

No,

because because what we didn't understand is changing workflow and process in the doctor's office. It's like if the nurse or the office manager goes, I'm not adding one more thing to my day that it ain't gonna happen. Right? So two more years go by. So we just talked about like when do you kill an idea? Two more years go by. We are at death's door and the only, I was able to raise more money because I was a VC and people trusted me and I had the integrity, which was great. But boy, I'm going to sleep at night. And I had raised millions of dollars and I had all these investors. Right. Right. So finally, duh.

We went, we realized that when there's a lawsuit, it's actually the hospital, that's the bigger pocket and it's the malpractice insurance provider for the hospital. We went to the malpractice insurance provider for the hospital. Who's the one who actually pays the millions of dollars in the claim. They went, well, yeah, we love this. They bought it. The insurance company bought it. They forced the hospital to use it. The hospital forced the doctor to use it. The doctor forced the nurse to use it. We had a business,

we knew we had a great product. The product was phenomenal. What we didn't understand. We understood the end user. What we didn't understand was the business of health care. And I had, I learned from this follow the money like who really cares and why do they care and who can force somebody to take an action. And it took us five years

to figure

that out. Right. But once we did, we turned into a big

business. Yeah. It's interesting because doctors, um, a friend of ours, uh, john Bedrosian started this company called National Medical Enterprises Enemy years ago and they manage most of the hospitals around the world. And it's like, wait a minute management. Yeah. Because doctors are like creatives, they don't have a stronger business side. They will not pay and and then you take the people in their office when you said that, I was like, of course it was like I created this mobile coupon app called Yowza to get the 15 year old clerk at the counter to scan a P O P O. S and get going to the POS system. It was like what they grabbed,

somebody had it on their phone. This was back in the day and they would take a coupon that they had laying around and just scan that and I'm like no, I'm not going to get the credit for it. Yeah. This is not going to show up as being the, the app that you turned to speak, but whatever is easier. It doesn't matter. No, don't tell me. So it's interesting that it took even you five years and then finally it clicked. So I mean you had chances to give up during those five years. It sounds like

I should

have even now looking back you say that.

Well, no, it turned into a really like this company sell for a couple $100 million. I mean it turned into a big company, big biggish company. But you know,

it's hard to know the difference between like you should stop, you should give up or do something else. Greg. How do you protect your computer? How do I protect my computer? You mean like do I have a lock on my backpack? What are you talking about? You know, there's two ways you can protect your computer. You could either like encase it in a giant foam bubble, never open it up. Or you could put some security software, like a vast one on it and not have to worry that you're going to be destroyed by phishing attacks or have your files taken away. Okay. So you're talking about protecting the things that are on my computer? That's the only thing that matters, right.

That's true. What's inside my computer? What I have and what I've I've taken from computer to computer to computer over the years is so incredibly valuable to me and I have been attacked a couple of times and I hated it. So what do I do? A vast one. That's the powerful suite that I need to get you added to your computer. It's Mac Pc, whatever it is, you know, it has everything on it has fire, it has a VPN, it has like a scanner to scan through like all your files to like find things. I did like the scanning and not just did it find like, you know potential issues, but it helped me actually save a whole bunch of space and found all these old zip files that were just taking up space. I didn't even need and this is like good maintenance for your computer.

Yeah, I played around with it a little bit and it found a bunch of passwords that were easy to, it was easy to guess and that passwords I've repeated a bunch of times. It's like you forget how easy it is to figure out, you know the complicated nature of your password. It's not that hard but that's just password. So is this for personal use business, use everything, it's for everything. But this is like something that every computer should have on it. And a vast they've been around for 30 years, they have 435 million people using them. They are the experts at this. 435 million people cannot be wrong. These people are protected. You don't want to be outside of that group.

Neither do I. So learn more about a vast one at a vast dot com, A v A S T dot com. I can see in the background strategically placed your book, several of your book which is about the exit and about like you know, ideally getting to acquisition whether it's super huge or not. Super huge. What is what's your book called? So everybody knows it's

called exit right? How to sell your business, how to sell your

stuff. Oh, that's great. That's exactly what we're talking. Well not exactly, but it's I think everyone listening wants to know how the hell to sell their business or a business. I want to know when, let's start with when, because this hockey stick that everybody refers to that hockey stick moment, you're not waiting until you plateau, right? I mean how do you know when is the right time to

sell? Yeah, we call that the local maximum. But but actually before we talk about when's the right time, Let's talk about why you know I'm a believer that you should, the Ceo is a servant leader and in servitude to your customers. Like you have to love your customers, you have to love your employees. You know the job of being a Ceo is there's a greater responsibility than just maximizing wealth for you and your shareholders. And the question is as you're going through the journey of your company, how are you going to continue to grow and meet the needs of your customers and what resources do you need and are you going to be able to do that internally yourself or might there be a better home? And we actually created a framework that we call fair which stands for fit alignment, integration and rationale. And the rationale is like how is one plus one equal 100. Can you explain to your grandmother in really simple language like why these two companies should be together? And if you can create sort of the Jedi mind trick, if you can create,

if you can get this buying company, if you understand the buying company so well that you understand their business, you understand their customers, their their their product line, their holes and you can articulate with the buying company, a rationale that says, look, if we plug our product into your customer base, we're gonna create this right, you know, an example, a great example that everybody knows is facebook and instagram. When Mark Zuckerberg bought Instagram for $1 billion 20, was it then 2012,

maybe 20 so long ago, I was completely inside, I was looking up, I was at the uh the party for that kevin Systrom through for the acquisition, like for the acquisition, it was in Vegas, there's a picture of me on TMZ with Adrian Grenier and someone wearing the dead mouse hat, I just had yesterday was 2012, I

remember that, but when they, when he bought it for a billion dollars, everybody thought, oh my God, Mark Zuckerberg lost it, he's crazy, this is a company with 40 employees and and no profits, no revenue, why would he do that turns out it's pretty damn smart, you know, last year, I think um instagram did like 21 billion in revenue. What people didn't, what people didn't understand was the rationale, which was look facebook wasn't in mobile back in the day, instagram was killing it on mobile instagram was a great way and they were,

their audience was going like this and there was a great way to help facebook move into the mobile market place and when you took that audience that instagram built and you monetized it with the facebook sales engine, then you created a behemoth that's a rationale. And, and so if you, so the fair framework is fit, Is there a cultural fit? You know, can you sit on an airplane for five hours at the end? You know, at the end not want to kill the guy sitting next to you right now. Are the companies have the same type of culture? You know, a great example is um, A. O. L.

Time Warner where terrible cultural fit and it was a disaster. One of the biggest disasters of of murder of M. And A. So culture fit the next is alignment Are all the stakeholders internally, your co founders, your board of directors, your investors, your customers, not only for you on the buying side. Oftentimes there's a champion at a large company. Maybe it's a product manager, maybe it's a head of sales. Is the CFO is the Ceo is the board board of directors of the acquiring company is everybody aligned two together to make this transaction happen. And I've seen so many transactions fall apart because there wasn't alignment,

but there's so many factors that will blind you in that it's exciting. It's, it's also a life raft. It's, it's somebody sending going, look, you're about to sink, we're gonna to save you or you know, do all, I would imagine a lot of it is air not fair like the first a couple of these will align but they don't all aligned but it's okay we're gonna we're gonna work it out later whenever two companies a company acquires another company and you see the statements from both sides. There's so many times when I just go uh it just doesn't feel authentic. It doesn't feel real. They're just saying what they're supposed to say and it's like you can just tell it's not gonna work. You hope it does one will give in one will change to adapt to the other. But you know it's so true what you're saying it's like you know when it all comes together and works its

magic right? But but many transactions fail. And in fact the next part of that is integration and integration Is the ugly step child. That that's the one everybody goes. Yeah. Yeah yeah we'll worry about integration afterwards. But it turns out integration is perhaps one of the most important aspects of this because in Ben's world in my world which is more of a technology world. Many transactions if you don't get 100% of the money up front there's something called earn outs where you get a percentage of the money over time for future performance. Well if there's future performance, if a good chunk of your money comes in the future and there's not a good integration plan. So maybe you don't get the resources you need or you don't get the programmers or it's not integrated into the sales team of the acquiring company or whatever whatever. If there's bad juju if there's bad integration, you know there's real financial implications to that. So so we we we wrote a book and you know it was such a joy. I had so much fun doing

it. Did Mark just call me a bad jew? That's what that's what I just heard and you repeated ju twice which is really offensive. Even from another jew.

Are you feeling

a little self conscious a little bit? I'm not the greatest jew, jewish but you know I

we can talk about,

okay I'm in my proxy from my my for my girlfriend of four years being I have now gotten heads. You don't have to be jewish to listen to this podcast. But I so right now um tell me about the companies that you are most excited about. I mean you must have your hands in a bunch of different pies.

Yeah. No we've made over 100 investments in our venture fund. Yeah. And it's um you know I'm really grateful. I love what I do and I love helping entrepreneurs and it's so much fun. It's not making you know picking the right companies of course but helping those companies grow and scale over time. You know that is just so much fun

at this point though. Do you like hearing you say this? It's like somebody might be listening going Yeah it's easy for him to say now, it's got all this money so successful. Did you still, did you have these same principles when you started and, and if you didn't, would have made you more successful back

then, do you think, Oh yeah, you know, first of all, um I'm a really slow learner. It took me forever, you know, I, I was, I was a nice guy, but I was really focused on myself, I wasn't a particularly good manager, I was really focused on, you know, building, being successful,

achieving whatever I wanted to achieve. And it took me a long time to get to this place and I wouldn't call it enlightenment, but I would call it a place where my, the focus isn't on me, the focus is on the entrepreneurs or building communities or helping and you know, that's just such a much better place to be.

You get, you get punched in the face enough times you learn how to dodge,

that's

how I feel as an entrepreneur just like punch in the face, Punch in the face. I eventually learned how to dodge. Right,

Well, isn't it, is it mike Tyson the one that says, you know, everybody has a plan until they get punched in the face.

Yeah, that's true. At what point is a company ready to come to a venture capitalist like yourself? Like, at what point are you interested in joining,

um, in

investing when people watch shark tank, it's, it's, you know, a lot of times it's like, well you have no sales, what what are you doing here? And they just get but that sounds good. Mr wonderful. Thank you. There's there's there are similar, you know, there are moments when I'm sure you see it and go, don't worry, your sales, sales will come. Here's what you know, it's different right? With every with every company.

It is different. But every investment fund has a different investment thesis. Some invest early middle late, some invest by geography, some invested by industry sector. You know, everybody has a different investment thesis. Our investment thesis. We love companies who know how to sell, who have an unfair advantage in customer acquisition, who have leverage in a sales model. And I learned this. I have a lot of scar tissue. Right? Going back to that story, I told about my medical software company. Um so I have a saying which is the greatest product in the world without customers is a great product,

it's not a business. And and most entrepreneurs are are really good at seeing a problem and solving it and human nature. So human nature is we gravitate towards our strengths and we avoid our weaknesses and most people are not comfortable with sales. Most, you know, most people are good at technology or they're good at finance or they're good at whatever, but most people don't like sales and the reality is so that the answer your question for us, every entrepreneur, every investor is different. But for us they, we like some proof points we liked when there are feedback from the market. But what's really important to us is the methodology. What we like to see is momentum and we like to see that there is a, the that there is a proven ability they understand and every company is different but that they understand customer acquisition and they know how to scale a business. So in L. A. You guys might know a company called Acorns Acorns is a Yeah. So I was an investment there

down in Orange County. Yeah,

Yeah. So I was an early investor in acorns and the reason I invested in Acorns was 2. 2 reasons one. I fell in love with the user interface. I love good design. I love good user experience and many technology companies and technologists, they overbuild. I love simplicity. Most, most software companies overbuild have too many features. Don't pay attention to design. Acorns nailed the user experience

and design. I absolutely agree. 100%. And I'm sorry to cut you off. But I have to say it's also a generational thing. I get it. My boys get it. I have three, you know, 18, and 26. All three of them love it. It's I call it financial insurance. It's it's such a great product. I love acorns. I use it to

my money goes out.

I don't have to think about it. Yeah, it's great.

But the other thing, the other reason I invested in Acorns is they were killer at customer acquisition. They understood they understood, you know, S EO and ECM they understood partnership marketing, like they were just the pros from Dover. Like they were just really good and I could see a methodology. I understood exactly how they were going to grow and scale. And so that was why I became an early

investor. Okay, so hearing you say that I know Ashton kutcher is a big was big in this, in in Acorns. So I look at what I did with my little company, Yowza, I was able to go on these talk shows, the marketing side of it, we didn't have to spend a lot of money to get customer acquisition, I got a million and a half people to download the app. You know, I was free and they were and it was at the beginning of apps and all that stuff and people fell off and whatever, but at the same time it was it was really easy. Do you like the idea of a celebrity being attached if it's Organic, Ashton is very unique because obviously he's just a very good investor, very good entrepreneur. But but I'm saying like if if because it's something that that Ben and I am working on and we're talking about it. I have so many celebrity people that are passionate. It's organic to who they are and they're looking for a business and marrying the two is is a pretty good idea. I think

I think it's a great idea. So I'm a big believer in trust. One of my investment thesis is just I think that we live in a world where there is a deficit of trust. It's really hard to get it, it's really easy to lose it. And so you said the word I think is really important here is authentic. So people can smell when a celebrity doesn't love a product or doesn't believe in a product, right? And so if it's authentic, the great thing about a celebrity is you have an audience so you have you have the

right.

So for that Yeah, as long as it's credible and authentic.

Yeah. I mean my millions of followers are all in a very small region of Korea. They're heroes, fans, big fans, big Star Wars fans but that doesn't matter. They still have phones and they still they still purchase um we have to, we were we have to make this a soup partner at some point because yeah, we're gonna bring you back on for sure because we started this show in part because Greg and I tried to do an idea over a decade ago and it didn't succeed for like various reasons which we'll go through but we're like, we want to do something again, we've got to not fail at it. So what's the one way to learn learn from our network of super smart people who clearly done it and much more successfully than either of us have done it and I know how busy you are, this is so terrific for you to take this time and and come on and you know, I really, really appreciate it man and you have to send me your skin care regiment because that's more important than anything I want. I do want to know before we like start closing out just like what is this skin care regiment or even just like, you know,

one thing we do like to ask is like the lifestyle habits like you know like if there's like something that you do that really helps you be more successful or helps you keep your mind clear or something that you just recommend other people do right? How do you get to sleep? Dude, that's the thing that I can't, I have, if I have lines to learn for the next day and I am also trying to work on an idea with Ben or whatever. It's just too much going on. I mean it's a two part question because I know you're gonna answer it the way you're gonna answer it, but also just how do you sort of keep clear. Yeah,

yeah, no, it's hard that part, I'm not so good at the how do you sleep at night, but the, you know, I think it's really, I stay in shape, I walk a lot, I eat well, you know it's just sort of the typical things. But I think the thing that really helps me the most is kindness is that um we have a saying, so I was the chairman of the board of our local synagogue called Misha Kahn and the saying is bring your whole self to something larger than yourself, meaning if you're gonna be there I'd be there like show up and but you're showing up for something larger than just yourself and I get such joy out of helping entrepreneurs and teaching. And it just it just it just makes me it just makes life so much more rewarding.

I couldn't agree more. It's hard when you put it in, I'm gonna put it into a charity context because um my oldest son is epilepsy, epilepsy is my big cause I've been the national spokesperson. As a matter of fact we rush medical center Chicago is I love it just as much as I love L. A. I just love it. Love love love the people except for you, Mark. I love the people, I love everything about it. But I have to say like um doing something for other people without expecting anything in return. That's that's how I define charity. But business can be the same thing if you if you really can sort of look at it I think and remove the oh wow, we're gonna make 100 million or whatever and just that's gonna come, it's gonna come if you do the right job and if you do the good thing you work with good people but like you just said it's so important and it makes you a better person. It drives you to do more if you're just if you if you're in it for the right reasons I guess that's what I'm trying

to say and you know the other thing is I think in terms of decades not in terms of transactions, what I mean by that is I love building relationships like with Ben that's been I don't know been 15 years. I don't want to think

about how long it's been. I have I'm starting to feel the age.

Well

Dude I know I know you're gonna you got another 150 years don't you worry?

But but you know if you're trying to maximize the moment like if you think of life as a zero sum game like good on you right? But but if you think of life as building long term relationships and friendships over years and decades you know that's that's just where the joy of it comes

in. Yeah I agree. Well this has been a joy to be so you know to spin what you just said but it really has been man thank you so much thank you. Where where can everyone find you and where can everyone find the book.

Well the book is, thank you. Ben. The book is exit. Right. And it's on amazon or any bookstore and I'm on linkedin. So uh M A R K A C H L E R. And I'm always glad to help. So please.

And Mark's cellphone number will be on the podcast. You can just get home address. Absolutely. Thank you for these nuggets and and know that I I know your time is valuable. We're definitely gonna reach out to you again man. You're amazing.

All right, well let's do it. Hey, so last thing I'll leave you with, I was at a charity event and I won the raffle and the raffle was a sports package to bears and cubs and all the all the sports teams in in Chicago white sox. But There was a $500 gift card to Manny's Deli. I

know those guys, they're the greatest.

So so come to Chicago like dude, they were on Yasa,

Manny's was on Yasser before anybody else, which is crazy. Look, I love Chicago so much. I cut the cheesecake at the taste of Chicago.

Who's that's

not Manny's cheesecake is it? It's it's

uh

we're gonna we're gonna have a culinary tour. It requires at least two deep dish pizza because I've been craving that for months. But Manny's doesn't have that. But no, no, no, no, no, we're gonna do several? We're going to do with stops. You know the manny's family. Do you know those people? I

don't know them well

I know them a little bit. Me too. They are great though. They're really good people, we're gonna use that $500. We're gonna come, we've got to do that. I love it. Perfect. Thank you so much Mark

Yeah, anytime

dude, are you, if that is the bar that you have set for the guests that you're gonna be bringing on, I'm gonna be listening to our own podcast, let's put it that way. That was, that was amazing. What a great guy. He made me, who I am, honestly and I feel like that's an incredible way to start our journey to learning how to start something successful and not just to do that, but to help a lot of other people, which is I think one of the big reasons why we're doing this because we could just talk to him alone, but much more valuable if we can all learn together from someone who's been as successful as Mark and we have some incredible people scheduled to come on, it's gonna be a fun time, it's gonna be amazing and he's just such a genuine guy. Do you,

how often do you turn to him for advice all the time. So his mentorship didn't stop at a certain point. You still, it's, it is whenever I needed, you know, sometimes like you're good for a or sometimes you, I needed to talk to him every single week through like hard times, right? Or through a specific project specific project or just any time I'm in Chicago I always will go and get like some kind of tasty food with him. That's the most important thing to me. Um I yeah, manny's deli dude, so good. Um so okay, well hopefully people are going to glean the same information from all of these people through these.

I know I will um and I'm really excited to see where business NV takes us man. It's not just its lifestyle envy, it's it's you know, this guy is built and all the people that you're bringing on, they've built their life, not just their business and they've done it in a balanced way. Um and I'm just going to learn from each one of them. This is just the beginning of a fascinating learning journey for both of us and I cannot wait to see who else we talk to and who comes out of the woodwork as a result of the next episode is unbelievable. Get ready. Business NV hosted and produced by Ben parr and Greg Grunberg. Music and production by me, Nick Marzook,