The Realities of Entrepreneurship with Mike & Kass Lazerow

[00:00:07] So in 2006, I was starting this company up called Stockpicker and this random guy calls me out of the blue and says I want to be This is a great idea

[00:00:16] I just sold golf.com and now I'm figuring out what to do and I want to be CEO of your company And so we meet for breakfast and he describes the breakfast meeting But he gave me all these ideas and they were great ideas

[00:00:28] So I stole all of them and they worked really well and I built up Stockpicker and sold it but then this guy and his wife They started their own company both Mike and Kass, their geniuses they eventually sold that company for 800 million dollars and

[00:00:45] We've been friends all along even though I rejected him for and stole all his ideas he probably did much better than if he had joined Stockpicker and They decided to come on the podcast and not only do we tell some some stories but

[00:01:01] They share some of their many secrets of entrepreneurship. So here's Michael and Kass Lazaro Two extraordinary entrepreneurs and friends. Here they are This isn't your average business podcast and he's not your average host. This is the James Altucher show

[00:01:24] So tell me what are you guys doing? What's going on? What's it? There's been like a big change now You're all active in social media. You're you're talking buddy power

[00:01:41] It's you're on to us. Oh, it's good to see you first of all. Yes. Good to see you guys It's a way too long shame on us ever since Your story we didn't want to be seen with you in New York City. I know We always loved you

[00:01:59] But yeah, we're jumping back into social, you know our kids are older now James. So Last one's 17. We got one more year. Yeah And so look first off I am always Loyal to anyone who's made me money you guys let me into your round buddy media

[00:02:24] 2007 was the round was it August 2007? Yeah, and Exactly, I was really grateful and a small I mean you sold the company The round was like a three and a half million dollar evaluation or something like that give or take and you sold for like 800 million give or take

[00:02:41] so so it was an incredible deal you guys are incredible entrepreneurs and Are you are you doing a book now? Like I know the book I know whatever you're doing is not coming out till next year

[00:02:54] But I wanted to get you on the podcast as quickly as possible anyway Cass you want to start with that sure so yeah, we wrote a book. It's called shoveling shit a love story and It's kind of our love letter to entrepreneurs and ourselves

[00:03:11] We decided to write this James because we've just been seeing the same things over and over again to all the people That ask us how to do a startup? What should we do how do we figure things out?

[00:03:23] What about pivoting models you name it and we've kept all this information and finally we were like Let's just put it out there and try to help as many people as we can. This is great because So many times I've used you guys as examples look

[00:03:38] I've even written chapters in books about you guys Before we knew if buddy media was gonna succeed or not like like I just Was a given for me that I was gonna succeed right in the middle of the great

[00:03:50] Recession because you were so good at pivoting at at handling the worst moments I mean you survived through kind of the worst period in our lifetimes in American economic history You I don't want to say you flourish that during that time, but you survived and did well and

[00:04:07] I remember one time I was meeting with a guy at Benchmark and he wanted to meet you guys and so I Sent them over figuring oh benchmark. You're gonna be having and you even call me like and he said look

[00:04:20] We don't need any more venture capital. Don't give people our phone number like you were just so solid You weren't like floored by anybody always very and and look I'll describe how like so so Mike and I met and then cast later

[00:04:37] I met you but Mike and I met because when I started a company stock picker calm kind of a my space for finance Is what I was calling it at the time

[00:04:47] Mike reached out to me and coldly cold called or cold emailed me and said you wanted to meet and you wanted to be CEO Stockpicker there's a little for our buddy media. You were you were just finishing out your

[00:04:57] You had sold golf calm and you're just finishing out your one year. You had to stay with AOL Yeah, no, it was I remember the first time I saw Stockpicker I said this is brilliant. I love this

[00:05:09] I got to meet the person who started this and I have a habit of cold Emailing and cold calling people I still do so when I love something I have to meet who's doing it and so I reached out you ignored me for a while

[00:05:23] Finally, you got back to me we met I can order you for a while You did that's okay. I emailed again and we met for breakfast I'll never forget this breakfast you ordered a milkshake and french fries

[00:05:37] What I thought was amazing. I remember at the red at the red flame diner on 44th and 6 flame and We had a great conversation. I provided some advice not great advice you went on to sell it But we hit it off

[00:05:54] We always loved each other you were very supportive during buddy media buddy media was not up into the right at all times it was a lot of hard work took a lot of toll out of our family and

[00:06:07] We eventually got over the goal line and we appreciate all the help But it was a crazy time so we started during the great financial crisis And if you would have told me that Bear Stearns would not have outlasted buddy media

[00:06:19] I would have bet all the money in the bank and we had Bear Stearns Lehman brothers The world was falling apart, but we had zero revenue when we started

[00:06:28] So there's only so low we could go we just started building and luckily Facebook grew and the rest is history and and Just to set the stage so And and also I'm very curious how it was working together

[00:06:41] Like it's difficult often for married couples to work as well as you guys have together But to set this age Facebook was more or less just starting. I want to say

[00:06:53] Facebook was getting into the public awareness just about a year or so earlier than buddy media started and At the time it was sort of reminding me of Like a kind of organized internet where every everybody could have a home page

[00:07:07] And it would look kind of the same and you'd had games on it and you had, you know all your friends It was like this amazing Archaeological dig of our lives like I oh here's my elementary school friends. Here's my high school

[00:07:19] Here's my college friends. Here's my first job friends and Just like when the internet was getting big in the 90s Companies needed agencies to make their internet presence You guys were gonna make like games and and other things for companies to use

[00:07:36] As part of their Facebook presence that was the initial kind of it was sort of like a zinga It was like I think this was like the initial model you switched models a couple times

[00:07:45] Yeah, I mean mark pink is was one of our investors and we love the game space We built a few games you are our number one player of our word game if you get the name of it

[00:07:55] I know and by the way by the way in our in our next breakfast at the red flame I was telling you like I said I remember saying you oh Mike. I have this secret to winning

[00:08:05] This game I forget now what you called it wordy or something like that word something and you were like do you cheat? I'm like no why would why would I cheat you're so good at it

[00:08:15] The leaderboard was like James and then everyone else a million points below James You know we realized early on we weren't good at building games We knew mark and the team at Zynga. They were awesome. They were aggressive. They're doing things that we would never do

[00:08:30] We were in New York We started talking to brands trying to sell them on games and custom apps and we had a virtual currency called ace bucks

[00:08:37] We're like shitty ideas before we landed on what we did and brands just kept saying how can you like we hate your things? We do not want to do what you're trying to sell us But help us with Facebook and it was a time that Facebook was loved

[00:08:54] Facebook was like social media was it was like a I love people were like this is gonna change the world if we connect everyone on one Platform it's all gonna turn out well. Well fast forward

[00:09:04] It's you know, they've ruined democracy and the mental health of our kids, but We didn't know that we just started helping beer companies and soda companies and others doing what they did

[00:09:14] And eventually we had eight out of the top ten global brands. So so so that's just it though is like you were trying to be this consumer online game company located on Facebook and

[00:09:26] When that wasn't taking off and the Great Recession was hitting you you made the excellent decision to pivot to an Agency model which is profitable and so okay, you approach Pepsi and say look will

[00:09:39] For X number of dollars will figure out your Facebook presence which is gonna be really important and that's what you did for a while That was your first pivot That's right. We we were we were building custom Facebook pages for the top brands and

[00:09:54] As you know, it's very hard to scale when you're doing anything custom, right? Yeah You can't you're basically eating what you kill and it just wasn't working and I think you had to do it for that time though

[00:10:07] Yes, we had we had to make the relationships with all of the different brands so that they knew we were competent, right? And I think it was 2010 Mike wasn't it then when we decided to pivot to a SaaS company. Yeah early 2010. Yeah

[00:10:23] and and what was amazing is we you know, we had no You know, there's no tech that let us do what we ended up doing early on It wasn't until Facebook launched their API is their platform where we actually could

[00:10:38] Programmatically do what our software let us do to start it was just how can we be a part of this world-changing technology? Eventually the answer because we were open to it presented itself when we ran with it

[00:10:51] I feel like so many companies they come up with a model and they like They can't get that business model out of their head like they have to do that or burn up in flames in the process and

[00:11:04] And and what always impressed me is that okay? You started off doing these games Didn't take off the way Zynga for instance took off Okay, let's take an agency model which you can always fall back on the profitability of your

[00:11:17] Contracts, but they're but like you said Cass. It's not scalable And then you kind of took what you were the recurring programs you were making for every company and man and sort of made them

[00:11:30] Like you said software as a service like a menu. I could I could I'm a company I can have a menu item now or a menu of things I can do with my Facebook page

[00:11:38] Right and the tools we built allowed them to reach their you know consumers their clients their customers online and if you think about these big brands they have Thousands of employees in different parts of the world, right?

[00:11:52] So how are you going to give them the tools they need to create the messaging to their actual consumers in different languages? Right with different permissioning and so Mike had this idea because we were already helping them to pivot to this model

[00:12:08] And we became what what brands needed which was the Facebook power tools That was our big campaign if you remember seeing that I Don't but I do remember seeing your your billboards in airports. Yeah airport. I landed is like, oh are you

[00:12:23] Are you buddies yet or something like that? Every brand needs a buddy. That was our timeline. Yeah. Yeah, that was a big play When I went we definitely did not have this money

[00:12:35] And we went to the board and I asked them for a million dollars more than I think what our current budget was was about 200 grand to do to bring back billboard ads like real print ads in the airports

[00:12:49] Between Thanksgiving and the end of January because I thought if I could you know, we had what do we have? 150 different competitors at that time Mike even more

[00:12:59] Funded exactly so how are you gonna break through the noise and I thought well no one's been doing this for a long time Let's do it and it worked. It was amazing

[00:13:09] How did how did you though like other than the like how did you be a product differentiate from the competitors? Who would be the main competitors that I would know of So they're small companies. I mean, we were the largest company

[00:13:23] We exited for close to a billion and then you had company called vitru and wildfire but you also had small companies that are still around like Sprout social and sprinkler and Hootsuite and Because it was you know, it's like AI

[00:13:37] You had every investor trying to get into these deals just throwing money at anything Yeah mentioned Facebook and Twitter and YouTube and social media and so We were able to fund the business and we're able to fund most importantly what you said earlier the pivots

[00:13:54] We just knew in our gut that the first I think three business models weren't gonna work And when I said we I mean Cass I come up with awful ideas and she shoots them down and When you shot an idea down that you argue I

[00:14:10] I pretty much told him this is the worst idea you've had and I thought acebox was pretty bad You have to remember that James the Facebook platform opened up on May 24th 2007 I know this because we gave or I gave birth to our third child

[00:14:26] And I was being wheeled in after a c-section and Mike's on his phone And I'm thinking he's like telling all of our family and he goes I know what we're gonna do next

[00:14:35] And I'm like you mean after the hospital and he's like no Facebook just opened up their platform I was like oh my god, so we've always had a relationship where we say things totally brutally honest and We run with it and we trust each other

[00:14:51] I think and I mean you've had a couple ideas remember that ticketing idea and I just shot that down I'm like we're not putting any resources behind this. What was the ticketing idea? Well, we've had

[00:15:03] I'm probably talk about the ticketing idea which I don't even remember it was so bad You know, I want to get the outfit in the room. It's it's not always easy So it's not all like wine and roses working with your spouse

[00:15:17] However, when it works, it's great. You have a shared mission. You have a shared purpose You don't get home and you're like hey, how was your day? Right, like you are working on a lot of stuff together

[00:15:30] Not only the company but we had three kids and three dogs and you know, it's what we call the imbalanced life in the book and so We've always fought well when we disagree that's been respectful

[00:15:43] It's been here's why and after basically cast being right like five six times a row early on in our career I Basically just said, you know, she's my You know, she's gonna keep us out of trouble. So just listen to her. She's the operator She's a realist and

[00:16:01] She's done that she showed us the way and when I've gotten in Trouble business-wise is when you know, I'm not working with her or when I make decisions. I don't work with it Don't talk to her

[00:16:16] Take a quick break if you like this episode, I really really appreciate it would mean so much to me Please share it with your friends and subscribe to the podcast Email me at alcatra gmail.com and tell me why you subscribed. Thanks. I

[00:16:30] Don't really know when you've gotten into trouble business-wise when was the time when you've gotten into trouble business-wise So we've done about a hundred investments personally So not all of them as you can imagine have worked out most of the ones that didn't work out were

[00:16:55] Things that I was passionate about that made no sense like why I launched What will need to I don't want to like shame entrepreneurs, but you know a lot of them and we're doing stuff in this space

[00:17:06] my biggest failure is you know to date I launched a company with an artist friend called shape matrix, which is still around and you know, we clearly weren't

[00:17:18] kind of two people who should have started the business together it was based on invention that he came up with and Cast didn't say no But from the beginning castes like you really want to start a company with an artist

[00:17:29] He created a new visual language based on the eight basic shapes and I was fascinated by it I wanted to commercialize it and so he raised 13 million we

[00:17:39] Spent the I spent three or four years doing it and like many startups that didn't work out if I had really tuned into what cast was talking about That's something that I Probably wouldn't have jumped into I think I think what he's what you're referring to is

[00:17:56] You can't overlap when you have co-founders, right? And one of the things that Mike and I do very well And I think that's the only time we really argue or if I think an idea isn't the greatest

[00:18:09] And he still wants to do it is I'm in my operations lane And he's in his kind of visionary sales lane and when we stay in those lanes It's amazing because there's zero overlap. We count on each other

[00:18:22] There's no follow-through or follow-up like hey, did you do this? Did you not we're just humming? It's it's great On the one hand though Both sides are important right you need to be able to try lots of things to find

[00:18:37] What works like and a lot of things that will seem to you. Hey, this is worth trying Probably not worth trying but it's good that you don't know that because Some things that seem to everybody like not worth trying might eventually work

[00:18:52] Agreed you need to have both you actually need to have someone who is a visionary and can Think about really creative ideas and and can pivot when needed But if we don't have those ideas, there's nothing I can execute on the operation side

[00:19:08] So he has he's the kind of person that wakes up in the morning And will pop his head out of the shower and be like I have an idea like at least 20 times a day

[00:19:17] He says to me I have an idea and so you need that every entrepreneur needs to either be that person or have that person And then you need to have the person that's actually operating and executing and figuring out if an idea can scale

[00:19:32] And so do you ever get sick of it though? You say like yo slow down Mike. We got it just Get one dollar of revenues Ever yeah ever I'm I'm the first person to tell him focus. You've got to focus

[00:19:46] I mean listen when you have a lot of ideas And you have really talked about this James right you write down ten ideas a day You yeah kind of have made ideas of practice instead of just writing them down which I do I

[00:19:59] Think out loud and I think Cass has come to realize that that's me processing Where it gets serious is I say okay? I want to do it and it's just like whoa whoa whoa

[00:20:09] Like can I can I tell him about the time so we were at the very end? She didn't wait for her mission I'm gonna do it so right before I think it was 2005 the end of 2005 before we sold golf comm

[00:20:27] We had a house and we worked down in this really small room So we had both of our computers back-to-back in this little like tiny office and it's like a dungeon and

[00:20:38] All of a sudden I get this doorbell ring and so I go up the stairs and there's like three pallets of Felt like green felt and I'm like I don't I don't think this is ours and

[00:20:52] The guy's like nope. Nope here. It's Lazaro, and I'm like, huh? Alright Mike. I'll let you tell the rest of it So I launched a business without talking to Cass was called free felt calm

[00:21:05] There's at a time when online poker was new and it was a lead gen business I would send you free felt in exchange for all of your information and then I would sell that information to the online poker sites

[00:21:17] And this is this free. What am I gonna do with free felt if I play also poker So if you play online nothing, but at the time home games were taking off And so you know a lot of people I don't want to ruin my dining room table

[00:21:31] I need a plea a piece of felt so it was a thing doesn't sound like a thing right now It was a thing because you had like world poker tour starting everyone at home was starting to play poker

[00:21:41] Let's just say it wasn't a great business idea and I should have saved the five thousand dollars I spent on 13 tons of felt But it shows kind of how I've grown as a human being and a business person over the years

[00:21:56] Were you afraid to tell like you said oh, I didn't I forgot to tell were you? Yes, I've really evolved in my ability to communicate Both my ideas and my feelings at the time I'm like if I could just do this and hide the felt somewhere unfortunately

[00:22:11] It was a room of felt so I didn't know where I was gonna hide this felt Cass is the operator as you could see so the idea that I had like 13 tons of felt that I had to hide in a tiny house That never crossed my mind

[00:22:24] But like all of us we've gotten wiser over time and I think that's You know the beauty the beauty being an entrepreneur is not just the we've always had ideas But it's putting in just ridiculous amount of work

[00:22:38] whether it's on the sales side on the hiring side and You know, I just assumed I'd be able to mark it Well enough to clear all that felt. I also didn't know who was gonna like put it into boxes and shit it out

[00:22:51] So it was like the worst idea ever Logistics is not again though. I do want to iterate that you Are great at coming up with ideas like like what when we first met about stock figure I literally you you you spout it out a bunch of ideas

[00:23:05] I literally stole every single one of those ideas and Made stock picker successful because that not 800 million successful but successful for enough And so I appreciate that and I thank you for letting me and

[00:23:20] I knew you'd be fine with me taking all the ideas because when you're an idea machine You're abundant in ideas. The whole key is you don't you don't kind of

[00:23:31] Squirrel away your ideas. Oh, I hope nobody steals this you be you have a mindset of abundance of ideas and that's very important And I've always been attracted to people who love ideas and

[00:23:44] Cass loves ideas as well. It's not that she just you know operates. She's a beginner's mind. She loves to learn But the idea that you can go from zero to one just come up with something and make it happen in the real world

[00:23:57] I've been doing that since college since before I met Cass and so That's the beauty of entrepreneurship. I think fast forward we realize that we don't have to reinvent the world every time and so You know really large markets are really interesting because there are people spending money

[00:24:14] You just as an entrepreneur put yourself in front of a big pile of money I want to ask about golf calm like how did you get that URL? So this is the business before buddy media so it started as golf serve because back in

[00:24:28] 1998 when we started it there were no, you know single word URLs left with the word golf in it and I had this idea that If you're a recreational golfer that meant you didn't go to private courses

[00:24:42] You had to go back to the same exact public course to get your US GA handicap And I just thought that was just crap like not fair And you know, there's all these amazing recreational golfers that don't have the money or the access

[00:24:56] just like Mike and I at the time and I said like we've got to go and start, you know providing us a handicaps and golf was huge and We started at golf serve and then I think it was wasn't in a part of like an ESPN

[00:25:12] And NBC NBC. Okay. Got it. Yeah, so NBC had invested in a company called quacka sports total sport and The company raised a billion dollars one out of business and they had all these like bankruptcy auctions and

[00:25:29] One of the auctions was for golf commas and it was a phone auction you dialed into a courthouse Somewhere and we were willing to bid up to a million dollars for the URL and we bid 289 thousand dollars and

[00:25:46] We got golf calm and we built it for a few years And then wait, how did you get the 289 thousand then to pay for it? So we already had a company so we had golf serve and we'd raised a little money to do golf serve

[00:25:59] And we were operating and I don't know. I forget if we like put some more money in I think we raised a little and had the money to do this because maybe People yeah, we you know because we saw this you know before apps before the mobile phone

[00:26:13] It was all about URLs right like every ad on the TV He said WWW dot Expedia comm or WWW and it was like you would plaster that so that's how people found out about websites

[00:26:26] And so we went after it hard because we thought that these vertical niches of You know focusing on primarily rich people at the time We're gonna do wine and health and fitness and some others never got out of golf

[00:26:40] And then ended up selling that for 25 million dollars to a company that no longer exists called Time Warner Which is crazy in and of itself that golf comm outlasted Time Warner When you sold that like was this the first time you guys had

[00:26:56] Millions as a couple like I know you had a public company beforehand this the student video thing I forget the name of it now But was this your first big hit? It was so that was the first one together I'd made a little money off U wire

[00:27:13] Which we took public as part of student advantage And that's what most importantly that's what got us to New York because golf magazine, which was the buyer owned by Time Warner wanted me to be the general manager of golf comm and

[00:27:29] Without that deal I would have never met you would have never met Howard Linsen would have never met You know Roger Aaron Berg a lot of the people who have been really important to our lives Yeah, and so I

[00:27:42] Mean did you go out and and spend the money like did your lives change when you've heard like the first time you made money And you realize oh, this is a viable thing for me to do. I'm gonna I'm going to be financially free in this life

[00:27:55] Well, you have to understand like and there's a little story to this when we started golf serve within We started September 1998 by December 99 We had sold it to chip shot comm Which was a company that made custom golf clubs out of Silicon Valley

[00:28:12] And it was the most expensive place in the world to actually build golf clubs, but they were registered to go public, right and They pulled that out the following year And so we went into bankruptcy with them and then had to restart the entire company again

[00:28:29] So by the time we had to restart it. We did not own very much of it It's like barely any of it and what we got out of it was enough to buy our first apartment

[00:28:42] All right. Well, that's that's something that's good. That is something. Yeah looking looking back It was a lot for us and we made three million dollars before taxes So you pay the taxes and it's like whatever two million then you show up to New York

[00:28:54] And you're like wait apartments cost what like public, you know private school costs what and so let's just say we didn't feel Rich living in New York City. We were very hungry. We had that taste of success without the

[00:29:08] Type of wind that we got at buddy media and it just made us work harder because when you're working with your spouse You're all in there's no safety net. There's no oh my spouse has another job. That's generating income if it goes mahala your life kind of

[00:29:25] Is impacted in a way that if you don't work with your spouse doesn't happen Well within a year of you guys starting buddy media You know the world entered this great recession

[00:29:36] There wasn't really no matter how much people liked you there was no money available from VCs. I imagine at the time and What was were you worried were you scared? Cass, what do you think? I

[00:29:51] Wasn't I know that's gonna sound kind of arrogant. I was gonna say but I didn't want to I just feel like We had a plan I knew Mike would always be able to pivot us to a model that worked

[00:30:03] And if I could hire the right people and keep them there That was going to work and that was our mission Right because Facebook was still growing recession or not. Yes, exactly Facebook was growing and We raised our seed round. It was hard

[00:30:21] But you know we raised like a million and a half at I forgot the valuation I trust you three million three and a half million dollars. It was a three and a half Yeah, cuz I think it all ended up at about five after

[00:30:31] By the way, I don't think you had a hard time raising money. Yeah, yeah I had to beg to I was surprised I heard that you were putting money in from Howard and

[00:30:40] Like why didn't you why did Mike know how it goes like once it tips like once it tips and you get momentum Then it's like super easy, right? Yeah, but you know, it didn't seem like a slam dunk as kind of young entrepreneurs

[00:30:53] Working together so a lot of people don't at the time didn't like husband and wife teams You know Howard Linsen was very important He committed and then you know made a bunch of introductions that made it happen

[00:31:05] But the valuation really reflected how hot the deal was right like hot deals don't get done at three point five million pre But we just wanted the money to go because we wanted to be fast. We wanted to just build

[00:31:19] The good news our later stage rounds were done in the hundreds of millions So I think it all evened out and we owned enough of it to be very happy at the end But it was a scary time in the world

[00:31:30] And we thought it was the perfect time to build something because less competition Facebook was still growing and if we just focused on our customers, which we eventually found we would be okay And that's what happened. I know Mike at some point you dealt with a

[00:32:02] Cancer fear like when what when was this in the timeline? So my issue has always been my heart So I have an artificial heart valve almost died twice congestive heart failure as a kid

[00:32:16] In between my sophomore and junior year of college. I had a new aortic valve put in so a fake valve I still have the valve I think I'm one of the longest living people with this valve because most people get it when they're 70 or 80

[00:32:29] I've had it since I was 19 and just turned 50 This year. Now cast did you think that was sexy? He had this I already fell in there at 19 big time That was exactly what I was like, I was looking for that definitely

[00:32:45] And so an only reason that's relevant is after that happened. I went from being kind of a stress ball and really You know worried about everything to like love and life. I'm like what's the worst thing that can happen?

[00:32:58] I didn't die, right? Like let's go like this is fun. I'm in that. I'm an overtime and So that fearlessness I think really helped me as I move forward through not only buddy media but you know to this day in terms of how I operate which is

[00:33:14] Yeah, you only live once I shouldn't be alive. Let's Let's do some awesome stuff while we're here And so what were some of the things like so you wrote this book shoveling shit

[00:33:24] What what is some what are some of the shit that is shoveled and how do you? You know by the way, it's interesting, you know, we were I Think you were mentioning age earlier It turns out the average age for successful entrepreneurs is somewhere in the mid 50s

[00:33:42] and you know some professions like mathematicians the average age for a brilliant mathematician is like 25 for the mathematicians greatest work but for historians or Writers the average age is 69 actually and this is from at a podcast guest Arthur Brooks

[00:33:58] Who who writes about this type of thing? He's he's he's very into transitions in life stuff Yeah, he's a Harvard professor. Jay. What was the name of his book from? success to success or From strength to strength very smart guy and but but yeah wisdom

[00:34:17] The wisdom of entrepreneurs people always talk about like the young brilliant entrepreneur But it's really the wisdom of entrepreneurship that drives success Definitely I also I think Mike and I feel like there's a lot of glorification around being an entrepreneur and

[00:34:33] What we've tried to to write about in the book is You have to have this like always on shoveling shit mindset that you're you're constantly Going to be shoveling out of some kind of mini catastrophe Some kind of you're gonna be fundraising all the time then something's gonna

[00:34:51] Something good happens something bad is gonna happen. You're in the middle of the storm You're coming out of the storm or you're about to head into a storm You have to have that mindset and those entrepreneurs that can actually

[00:35:03] Grasp that and like it are gonna succeed because that's really what it means to be an entrepreneur in our opinion so being able to basically expect those Shit storms to use the phrase and and not quite enjoy it but learn how to how to how to ride

[00:35:21] Yes, and and have high you know stress and distress tolerance like you have to know that like there's no We meet so many entrepreneurs I'm sure you do too who have great ideas or have an idea and they think this is gonna be the greatest thing ever

[00:35:37] I'm gonna be able to work the hours. I want to work You know I'll make all this money all this kind of stuff all these like Interesting ideas, but when you actually start doing the work. It's not like that

[00:35:48] You won't miss like big events maybe with your kids or your friends, but you are missing all the like in between That's like one of the big messages. You are you this is always on Yeah, and and it never turns off and

[00:36:04] I would say 80% of the time. Maybe this is just me. I would say 80% of the time It doesn't really feel good Like it's no it's really Torturous yeah, I think we wanted to like we've read so many of these books because you know, we read an entrepreneur books

[00:36:25] you'll have our friends have written books and a lot of them glorify it and our series of Just kind of lessons. It's hard to apply We wanted to write the most honest book of the life of an entrepreneur not just the business

[00:36:39] But the imbalanced life the sacrifices the misery and really what we came out of it saying is that There's nothing we'd rather do. It's both miserable And awesome, and that's why it's shoveling shit a love story. It's our love story

[00:36:57] With each other, but it's also our love story of entrepreneurs Why we've invested in a hundred entrepreneurs? Why we're so Excited to give advice even when we didn't have money like when we met and at the end of the day

[00:37:11] There's like, you know a world where people don't have purpose and passion Entrepreneurs have that like they show up to work. They're like wait what like what just happened Like who just quit like what client just left us like we got sued by who?

[00:37:28] Like you show up and it's just like shit hits the fan and you just have to deal with it and at the end of the day It's awesome and the people who do it and who get to the other side Start to love it in this

[00:37:44] Masochistic way they start to love because it's not like it's not that people are smarter who are entrepreneurs It's not that entrepreneurs are any more strategic like go to any business school go to any company. They're really smart

[00:37:59] Strategic people it's the people who are willing to put in the work or make the sacrifice Who are willing to basically not see friends piss people off by doing what they do And so as we kind of thought about our life and wrote down these 30 years of stories

[00:38:15] It came down to man this sucks And it's awesome. I mean I Think probably you have a higher tolerance for it than than me like I just For instance, I remember having this web agency at one point and then just you get those calls on like Friday afternoon

[00:38:34] from the client that is Most on the edge and he says listen you need to call me Talk to you soon, but it's Friday afternoon. You call and they've already left for the weekend So now you have all weekend where you're like assuming you're gonna lose this client

[00:38:49] And and you're gonna have to fire people and and then by the way, then you don't lose the client But it's just weekend after weekend or day after day. There's there's some there's always something happening

[00:39:00] To worry about and and in every business I've ever done or been involved in It's just a lot of a lot of worry like you ever wish Sometimes I look outside. I wish I was a professional birdwatcher Then my job is to take a notebook. Oh, there's a

[00:39:21] Yellow-tailed whatever it is and like you just write down the names of birds and Life's good. Well, we tried that like I left so After we sold to Salesforce I Went to Mark Benioff and I said one of us has to get back home

[00:39:40] You know our kids were struggling. They hadn't seen us in 13 years or whatever it was We just needed to focus like you know in your gut that wow your family's falling apart So obviously like those either me or Cass Cass volunteered so she

[00:39:55] Got laid off, which was good like Mark treated really well paid her all over stock Like he was total mensch, which we forever will appreciate sure Then I busted my butt for four years and then I was like fat and unhappy and not connected

[00:40:08] Like I wanted to be with Cass and the family traveling the world So I left Salesforce and I said I'm just I'm not gonna do anything Now I don't really I got I'm a painter on the side and so I got an art studio

[00:40:25] Actually, I got I got you the art Yeah, I don't know how to get anything I haven't logged into party by the way But like it's hard to get at least of anything in New York City. It is that was really really hard

[00:40:39] Yeah, and it was right by you know one of the places you used to live at where it's it was at 78th Street Oh, yeah, I was in 78th. I lived at the Abford on 7th and Broadway and after a year. I was like I'm miserable

[00:40:53] I fucking suck at art. So it's a hobby like hobbies are things you'd love but suck at And I'm like I built businesses. That's what I do And so we went back into investing and now we're kind of full-on on the investing side and

[00:41:07] You know buying companies and who knows maybe one day will start a company Well investing companies in and of itself is start is starting a company. It's a company to yeah That that helps manage and operate multiple companies that you have small stakes in that's right

[00:41:23] And then there's a lot of decision-making and so on and we went after that hard I mean we you know at our venture firm velvety ventures We've got 400 million of assets under management. We've done our own investing And although we do love investing and will continue to invest

[00:41:42] What really separated us is our love of being an entrepreneur? And what are some of the other pieces of advice you you conveyed to some of your entrepreneurs or to the readers of this book?

[00:41:53] And I know you don't want to give away the when's the book coming out actually March of 25 So don't worry. You'll be back again in March when it comes out like well We'll go in depth into the into the book or like what's one or two things?

[00:42:06] Well, I think we've touched a little bit on it about the imbalanced life and you know Mike says like picking your co-founder is like picking your spouse, right? You're basically work married to this person So you better get it right because it's awfully hard to divorce

[00:42:22] Yes someone that you've picked as your work partner, right your other founder. We've talked about pivoting I mean, I think that's a huge chapter in the book that goes over You know

[00:42:32] How do you know when you need to and I think like you've said these entrepreneurs and people get so Full of pride and I think that's why they're not pivoting when they want to or when they should

[00:42:44] Because they're holding on to an idea. It's ego-based. It's fear-based. We go into that quite a bit we also talk about Marketing and perception is reality and how you can do this in a very effective and efficient way when you are a startup

[00:43:00] and teams I mean teams are like a couple chapters of our of our book because It's the most important thing like the thing that differentiated us were our people, right? It's not just a business model. It's just a mike's idea or how i'm executing it

[00:43:16] It's the wonderful people that we were able to hire and field in the right position I call it money balling, but it's it's really you get a lot of velocity And good things happen when you put the right people in the right spot I think that's really true

[00:43:32] And I think a lot of people don't know how to recognize who the good people are Like people are such good salespeople That they can convince others. Hey, i'm you i'm your ideal employee. I'm your ideal partner I think it's really hard to find The right team

[00:43:47] Yeah, I mean it wasn't easy and I remember Right in the beginning when we started in 2007 and 2008 It was hard to find any engineer and at that point We just started buying these small engineers who had apps

[00:44:00] So we buy their apps and then kind of inherit them. That was one way we did it But when we think back about Jeff ragavan for instance, how did he find you mike? Did he facebook message you? I reached everyone

[00:44:14] I knew say I need a really great salesperson and someone in the northwestern development office northwestern University is like fundraising team somehow is connected to Jeff and then we that's how we met

[00:44:25] Yeah, I mean you you meet these people and if I tell you like he's the greatest salesperson I've ever met so strategic Probably the number one relationship person I've ever met and How do you sell?

[00:44:37] How did he sell your services like because there wasn't like a a guy in charge of facebook for Pepsi cola at that time like who did he call? So the way you know Jeff and kind of our whole team sold was

[00:44:52] You know cast in the marketing team would soften the field by like we did tons of marketing tons of dinner events tons of just events And we basically had a vision and the vision was that the world is moving from ads

[00:45:10] To streams and this was back in you know, oh 708 So it was before everyone was just like on instagram and all these apps just looking at the stream And we said you have to adapt and birds of a feather flock together and

[00:45:25] We offered off the shelf everything they needed To succeed with first facebook the other thing that we did very strategically is peter Teal who's on the facebook board was one of our investors We got very close with the entire facebook team the sales team and the go-to-market team

[00:45:44] and so In order to spend money with facebook they had to get up and running on software that helped them manage it And so we became the number one Provider and they started just sending clients. We I mean it grew fast now

[00:46:00] We didn't realize how fast at the time But we grew from zero to 50 million in annual recurring revenue In three years so from launching the product to getting to the 50 million dollar run rate And actually we crossed 5 million in monthly recurring revenue that month That is really fast

[00:46:22] I don't think we've had any companies that we've invested in That did that and we got there because there was a seismic shift in the world That facebook was ushering in it wasn't us. It was every company waking up and saying

[00:46:35] I got to figure this out. How do I figure out? Oh by buddy media And and it wasn't it wasn't a coincidence that that happened I mean there was people don't remember there was excitement around facebook then i mean look it was I think in the summer of

[00:46:51] 2006 I think was microsoft offered facebook a billion dollars And they turned them down And I remember writing at the time in the in the financial times or what a column uh, facebook was smart They're worth at least a hundred billion dollars

[00:47:04] Everybody at cnbc laughed at me because then I went on cnbc to talk about it But of course it became more than much more than a hundred billion dollars a few years On ipo day was a hundred billion dollars but uh

[00:47:16] So so and then what was strategically smart was Getting right away in your round Maybe two of the most important people on the facebook ecosystem at a time peter teal and mark pinkis Yeah, and ron conway who was very close with um You know zuck and everyone

[00:47:35] Out there we we spent a lot. I spent a lot of time on the west coast building relationships I felt like If we're going to build on a platform We really need to be close to that platform because at any given time

[00:47:46] We were one decision away from being out of business They could have just said listen no more apis no more marketing Platforms we are going to do that And that's happened in some other areas if you think of twitter twitter shut off apis

[00:48:02] I remember twitter that affected howards stock twits Yeah, and so these platforms have a way of like being nice until they're not nice Right. Oh, we love you build on top of us until they're really big and then i'm like, oh, thanks

[00:48:16] We'll take over from here. And so I spent a lot of time out there and Yeah, i'm not gonna lie a lot of What we did at buddy media was

[00:48:27] I mean we did a good job, but a lot of it was luck like let's just be kind of completely honest And when I say luck it's timing It's everything went our way At a time when it didn't have to go our way

[00:48:39] And so we were part of something much bigger. We just happened to be there with a bucket Mopping up the money. I don't think it was luck in the 2009 or 2010 time maybe it was I don't even think it was luck in the beginning, but maybe it was good

[00:48:54] In 2007 six whenever you first had this idea it was it was Talented that you recognized this was something that was going to have explosive growth I was so excited the first time I use facebook because

[00:49:07] I would I remember thinking when would I ever call up my first grade best friend And ask him hey, how'd your kid doing a soccer match yesterday? I would never do that

[00:49:17] But now I see these things and everybody in the world can and it was just an amazing feeling Which doesn't anymore for some reason but that's why we're gonna jump in That's what you just said is exactly why I love facebook

[00:49:30] Dudes don't love calling other dudes, but we like keeping in touch right? Yeah I mean This is something else that that I think we talk a lot about in the book Is networking there's and fundraising right there

[00:49:45] You never stop networking because you never know where your next dollar will come from or your next opportunity And mike was so good about that It's grueling. He was traveling all over the country all over the world

[00:49:57] But you as an entrepreneur you can't sit still and just hope okay Like I can pick up the phone and call someone you have to build that relationship And when you do build it then there will be people who are interested and to ours delight and surprise

[00:50:11] Most if not all of the people that invest in us are really good friends of ours now And we're still in close, you know in touch and really close with all of them I mean, I think of karen kline

[00:50:23] And and she's you know one of my favorite investors to invest it on behalf of softbank. Yeah And what what's a good like going to conferences? I always find to be a horrible networking technique for you guys What is a good networking technique? So I love cold calling

[00:50:39] Like you did with me Yeah, I think If you think about most people like they haven't made a ton of money, right? And so all you have is time So instead of watching netflix Pull up your computer

[00:50:54] Find people's email addresses write in through like info at whatever dot com Tell a good story and try Like these doors will not open up for you unless you try to open them up

[00:51:08] And I've always just you know when I was I it was just thought about this haven't written about it or anything When I was like 12, I wrote to the board of a company called sally may student loan marketing association

[00:51:20] I was 12 years old. I said you have no students on your board I would like to serve on your board And they responded they said Thank you very much. We don't accept seventh graders. You know, that would be illegal We can't employ children anywhere in our business

[00:51:39] And they use like a child labor law to say like why it couldn't be on their board of directors and be an officer Really think about it. Like they had a meeting. How do we reject this kid? And so like I just think entrepreneurs

[00:51:53] Have it you know, you're an entrepreneur where you will Not shame yourself into doing things Or out of doing things that are really uncomfortable. Like it's not Like I don't love emailing james altischer about his company

[00:52:09] But I love the company like I was just with a friend of mine who started bonnaroo And outside lands big music festivals, right? And someone asks us how'd you guys meet? And you know rick farman who's at superfly, you know invented the modern music festival

[00:52:25] He goes well, I got this like email from last said that he came to my festival with his two kids And he created a video about How much fun he had even though it was 110 degrees and he was sleeping in a tent and almost killed them

[00:52:37] And I thought it was awesome and we got together and I've been friends of them ever since so People who are listening to this who are not thinking about Who are the people that they'd love to meet because most people are sitting around like

[00:52:53] Board and if they get an email from someone who's like, hey, I really like what you're doing I'd love to just like talk to you and see how I could help out Like a lot of people will respond whether you're mark cuban or whether you're cast lazaro

[00:53:05] But by the way as I realize this through my own career This becomes like a magic power practically the fact that most people don't realize this That like a lot of people reach out incorrectly and I hope in your book

[00:53:17] There's ways of reaching out correctly. A lot of people just say, hey They don't really provide value like you provided value. You told sally may at the age of 12

[00:53:26] This is this is a problem you have from my 12 year old point of view and here's a solution to it And so you you have to do that and iterate over and over before one person responds But that is the way to do it

[00:53:37] You have to provide value like What I mean with an entrepreneur The question I always ask is how can I help if I could make anything happen in the world?

[00:53:48] What is that one thing? I can't do too much for you or I got a job. I got a family I don't want to like You know piss them off, but like what's one thing that if I did for you would really change your business and

[00:54:01] That question sticks with entrepreneurs years later Like big entrepreneurs like entrepreneurs who like make it You remember how roger erinberg always says it too like he can't stand when Entrepreneurs or anyone says hey, can I pick your brain for a little bit? I know it's the worst

[00:54:19] It's the worst because it just it's offensive like my time isn't worth it and your time is and all that kind of stuff The way mike's gone about it and and taught so many entrepreneurs is the right way

[00:54:31] Like I have some ideas. I'd love to share them with you. I'd love to help You know that kind of mindset is necessary to open doors By the way, my equivalent 12 year old experience if you don't mind me sharing is in 1980

[00:54:45] So I was born in 1968 in 1980. I went to the democratic national convention Which was a new york city because I told them they needed Kids can influence parents So they needed like junior democrats of america and I was happy to run it for them

[00:55:01] And so they invited me to hang out on the floor of the convention with all the other delegates and stuff and and so I I spent the convention there Doors can be opened and it's not

[00:55:13] You know, I look back and I love warm intros and you know take advantage of them if you can get it But you need to open your own doors and I think that's what sales is sales is like

[00:55:26] Getting someone to do something that you want them to do without them knowing That you want them to do it Now let me ask you now. Did you did you write this book together? Yes, we did It was an interesting process you would love this because

[00:55:43] I had all these ideas that I'd written down and you ready for this in a spreadsheet because I think in spreadsheets And I'd written them all down and kind of built the chapters and ideas and each cell was like a different bullet

[00:55:56] And I go okay, mike. Um, I need a little help with this. He's like, I can't write a book in in excel What are you talking about? This has to be an award document. He was mad This is like a two-day discussion

[00:56:10] Well, how did then you break it into stories and and write the book? so we didn't like We didn't You know We had a lot to say but we didn't really know what a book structure was because we read all sorts of stuff

[00:56:28] And we didn't want it to be just You know, and so we like we do everything we asked a lot of people And we had we wrote it but we had help from someone who's written a bunch of books about like how should we think about structure

[00:56:43] Cass is all about structure Once we had structure, which was basically Three or four stories a chapter Three to five lessons per topic like key lessons The writing was really easy and because we have 30 out 30 years of material I wouldn't say it was enjoyable

[00:57:05] But it was we got into a flow that got it done Yeah, because you had the stories. So it was a question of dividing up the stories By chapters and that's something that's very structural. You you can do in a spreadsheet

[00:57:17] The part that gets a little tricky is It's like you have a sign behind you right now. I'm like day trade day trading attention Writing a book is like day trading attention. You have someone's attention

[00:57:27] You know, you know, you have someone's attention at the beginning of a chapter Otherwise they would not have opened that chapter, but then you have to keep that attention

[00:57:33] There's a give and take and it's very important to hold on to it. It's a precious thing someone else's attention And I'm sure by the end of this book you you appreciated the importance of that

[00:57:46] And you know, I went to journalism school. I love stories part of like sales fundraising everything is a story And I didn't want and casted in one the world's greatest textbook about entrepreneurship We wanted a very quick read

[00:58:04] That when people put it down, they're like that was worth it. I learned something. It was funny. It was fun I got to know these two goofballs And so I think that's what it is is it's a fun read that happens to teach you about

[00:58:16] You know money balling and pivots and raising money and picking a partner and how do you green light an idea? And how do you kill an idea and all these things that we've just done over and over and over again

[00:58:28] It's basically the combination of all of the questions we get from entrepreneurs every day told through our stories And our love story I can't wait to to read all these stories. Uh, the book's coming out next march You'll come on again to talk about it. I'm assuming

[00:58:46] And everybody's loved it. Can people pre-order yet? It's probably too early to pre-order Yeah, not yet, but then go to cast and mic.com and sign up for a free chapter and connect with us And we're gonna be having some fun. We'll be doing events

[00:58:59] You know, so definitely sign up. We want to we want to make this interactive We love entrepreneurs So part of this is we want to interact with more entrepreneurs as we You know go through the process of promoting the book

[00:59:11] So everybody should sign up for cast and mic.com And I I just knowing you guys I can guarantee those events are going to be something special and and worthy of attending I will seek to attend And I do want to mention when I did

[00:59:26] Write my article. You said to me mic that I wrote it just to be Shocking and now you probably know having written this book If you write something just to be shocking, it'll never be good

[00:59:38] It won't be good. You have to care about what I did care about what I was writing and And it was important to me now at the time You wrote something that's probably the nicest thing that anyone has ever written

[00:59:51] about us other than like maybe something our parents wrote us and You know at the time I think we were in a place or it's just we were in ptsd But we've taken that with us and there are a few people who really

[01:00:06] Um impacted us in a huge way kind of how you think and how you think differently You know gary veiner chuck who started his his business from our conference room at buddy media Um, who you know, he wrote the forward to the book one of our

[01:00:21] You know great friends and we've seen him build his business. We've seen you write like 15 books since we met and do all your businesses so um, you know part of this book is a love story to you guys for uh saying yes to us and building that relationship

[01:00:40] Well, I always appreciate you guys. I'm looking forward to the book. I'm looking forward to you coming back on I know you're gonna have some amazing stories to tell and Thanks for giving us this this intro now To be continued

[01:00:54] Amazing. Thank you. Thanks for having us. I appreciate it