From Refugee Kid to Startup Founder: The Shane Neman Story

Welcome back to Mork Unfiltered, where we strip away the polished bios to get to the raw truth of building a business. Today we dive into the Hollywood-esque story of Shane Neman. From a refugee kid sleeping at the foot of his parents’ bed to a studious pre-med track, Shane’s life took a sharp turn after a Sunday afternoon chat.

He dropped out of med school, survived the dot-com crash, and found himself in the back offices of gritty NYC nightclubs at 4:00 AM. It was in that chaos that he accidentally invented a pioneering SMS marketing platform. We discuss his "masterclass in BS" to land clients, his high-stakes legal battle with T-Mobile, and why your life partner is your most critical business decision. This is an honest look at surviving the entrepreneurial marathon.

Chapters

00:00: From Med School to the Dot-Com Bust
05:15: Growing up in a One-Bedroom with Refugee Parents
14:30: The Sunday Afternoon Decision to Quit Medicine
25:40: Learning Business in a Nightclub at 4:00 AM
31:10: The "Masterclass in BS": Faking it Until You Make It
42:15: Accidentally Inventing the Future of Text Marketing
46:50: David vs. Goliath: Taking on T-Mobile in Court
53:30: Selling the Empire and Shifting Identities
59:15: Why Pedigree Doesn't Matter to a Millionaire Investor
01:08:30: Lightning Round: Superpowers and Dinner with Elon

#Entrepreneurship #StartupLife #SaaS #BusinessStories #SuccessMindset #VentureCapital #MorkUnfiltered

Transcript

SPEAKER_00 0:00

If I actually knew what I had to go through in a 10-year period, I don't know if in retrospect I would have actually done it.

SPEAKER_02 0:07

How much did that drive you and how did it make you feel, man?

SPEAKER_00 0:10

We did a startup and someone was dumb enough to give 22-year-olds millions of dollars to do a startup.

SPEAKER_02 0:17

And you go from, I guess, being worth a significant amount of money on paper to everything falling apart. You just can't cut corners no matter how much you want to. What's the number one thing that kills startups? Welcome back to Mork Unfiltered, folks. I got a question for you. What if everything that you knew about business, you actually learned in a nightclub at 2 o'clock in the morning when everything that could possibly go wrong is going wrong? Today's guest dropped out of med school, went broke in the dot-com crash, then built two, not one, but two SS companies from scratch, which he then sold. And along the way, he accidentally invented one of the US's first SMS marketing platforms, got sued multiple times, and nearly lost everything more than once. Today he runs his own family office, has backed over and invested in over 50 companies, including some notable unicorns like Figure AI and Sandbox AQ. He wrote a book chronicling all these crazy stories called Nightlife Lessons, which has been honestly one of the most crazy and honest accounts on entrepreneurship that I've actually ever had the pleasure of reading. So this is Work Unfiltered, and this, folks, is the story of Shane Neiman. Shane, welcome to the show, man.

SPEAKER_00 1:31

Well, Patrick, thanks uh for having me and being so generous. And um and thank you for that introduction. That was awesome.

unknown 1:39

Thanks.

SPEAKER_02 1:40

You're more than welcome. You're more than welcome. So listen, you know, before we kind of jump into some of the crazy stories and we're we're we'll get to plenty of those, but I I want to kind of go back to, you know, your your childhood as a kid, because you know, one of the things I found, you know, interviewing successful people is that so much of the way they operate and and the way they kind of like function is is you know is rooted in their childhood experience. So tell us a little bit more about you know, what kind of kid were you and and what influenced you and and you know, what were you really wired for when you were kid?

SPEAKER_00 2:11

Um, you know, so I I grew up in New York. Um my family, my my my parents came from Iran in the late 70s. They were um, you know, they were refugees that came with nothing, kind of classic immigrant story. So I uh I watched them rebuild their lives. Um, you know, they came, they were, my father was an architect, my mother was, you know, a stay-at-home mom, but also a teacher, and they had a very good middle class life. Um, and then, you know, they got uprooted and had to start all over. I mean, I was born in the United States, so I was very lucky in that respect. But um, you know, we we we lived in a very small one-bedroom apartment uh in in Queens for, I don't know, a good part of the first 10 years of my life. Um, and you know, slept at the foot of my parents' bed, kind of thing, saw them, you know, rebuild, um, try different things, fail at certain things, uh, and then finally get on their feet to kind of um, you know, they they built their own business. Um my father couldn't become another architect because he'd have to go back to school, which wouldn't make sense for him. He he went into clothing where he could use his design skills. And eventually they they built a clothing line. And um, you know, I watched them basically build these things in front of me. And I had a front row seat to it. My I was an only child, so I got to see it like really, really uh out close. And so um, you know, my parents would work till like three in the morning and they had like a kind of workshop in the in the basement, and I would fall asleep down there watching them work and do whatever it takes. Um, they had the hustle, you know, yeah that you talk about where you know they're they're really working because they um they wanted a better life and they they had a crazy work ethic. That taught me, you know, tenacity. It taught me that to that will to do the things that I don't want to do. Yeah. Because ha half the battle is, you know, doing stuff that you maybe don't love to do, but you have to do to get ahead or get to your goal. So, you know, that that that was a big influence on my life, a huge influence on my life.

SPEAKER_02 4:38

That's interesting because you know, so many people who go through a tough time like that, you know, particularly I've I've interviewed a bunch of very successful immigrants, uh entrepreneurs and CEOs on this show. And, you know, it is so tough as a kid growing up like that, like sleeping on the floor at the feet of your parents' bed. I mean, how did that make you feel as a child growing up, you know, and especially in New York, where there's a lot of, you know, there's a lot of affluent people, there are a lot of successful people. You know, as a kid, you're kind of constantly in this psychological game at school of comparing yourself to what other kids have. How much did that drive you and how did it make you feel?

SPEAKER_00 5:13

You know, for me, it was never about uh comparing myself. I mean, maybe I was just innately like that. I think some people are like that. I still am not like that. I'm not really comparing myself to even even when I ran my businesses, I didn't focus too much on my competition. Right. I just was focused on what I could do to improve my situation, which which again was was something that uh, you know, in particular I learned from my mother uh because uh when I was 13, my my my father passed. Um, you know, unfortunately, he died, he died young. He he he he had cancer. And um, my mom had to start all over again, again, because she didn't, you know, have the design skills to run that business. And so she had to figure out something else to do and be a single mom. And she was also perpetually ill herself. Uh, she had a lot of health problems. But despite all that, she never really complained. Um, she just picked up the pieces and, you know, never was like, why me? Look at this person. They have this and they have a perfect life. She was just like, okay, this is the situation. I'm gonna make the best of it. And, you know, her work ethic was incredible. And that that really kind of um it changed my vantage point into thinking that anything is possible and um that you should, you know, just do. You know, a lot of, you know, my my my mom, you know, was able to do these crazy things. She ended up becoming a big real estate entrepreneur, ended up buying a lot of real estate over the next couple of decades, becoming very successful despite she had four kidney transplants. I can't get a few. Oh my god. Yeah, she was actually one of the first kids in in the entire world to get a kidney transplant uh when she was very young. And so, um, and she got that in America. And and you know, she she thrived despite that. So uh that that that's I think for me, I never had the chip on my shoulder being like, you know, I want to be like Johnny next door who has that house or that that that that parent that can do it. It was more like, how do I focus on myself to improve my situation? That's always how I kind of thought.

SPEAKER_02 7:32

Okay. I mean, you know, having a situation like that where you grow up single child, your parents are struggling, then your father passes and your mother has to start all over again. Walk me back to that moment. I mean, that week that that happened. How did you process that as a teenager? What what went through your head?

SPEAKER_00 7:50

I was very lucky. You know, I had a I had a large family that kind of supported us. Uh, but obviously, you know, losing your father is not easy. I was worried, obviously. Um, but you know, my and I was obviously very sad that I lost my father. I was, you know, he was he was ill for a little while. So I kind of like knew what was gonna happen. Um and you know, I think for me, um just seeing my mom being strong about it got got me through it. She she, you know, she wasn't apathetic to it, obviously. She was very sad and everything like that, but she wasn't like falling apart. And she, you know, she quickly kind of pivoted and you know, was like, okay, what do we need to do now? And and she went into like problem solving mode, right? When when even though everything looked like it was impossible for me basically.

SPEAKER_02 8:49

Yeah, she had to be strong, right?

SPEAKER_00 8:51

So yeah, she had to be strong. I was only like 12 or 13 at that time. And so um, you know, I was I was old enough to really understand what was going on. So um she really paved the way for the way that I think about the world, right?

SPEAKER_02 9:08

Yeah. And so you decide to, you know, you graduate high school, you decide to go to computer science, you know, Barry Goldwater Scholar, Phi Beta Kappa. I mean, that's some serious firepower, right? You you you were smart and and hardworking and a really good student. You end up going to med school. Um walk me through the thinking there. Why, why med school, right? Because you you ended up going down a completely different path afterwards. And and kind of what were you after when you made that decision?

SPEAKER_00 9:36

Um You know, obviously, because of the situation that I had with my with my father and my mother being per perpetually ill, to me, being a doctor was the most noble thing I could possibly do. Let alone, you know, coming from an immigrant family, everybody wants you to be a doctor or a lawyer, or you know, so true. That's so true.

SPEAKER_02 9:54

So, like, you know, that that that that was.

SPEAKER_00 9:56

Or engineer.

SPEAKER_02 9:57

Or engineer. It's like doctor, lawyer, or engineer, right? Yeah.

SPEAKER_00 10:00

Yeah, absolutely. I mean, I think that was um for me, um, what happened was I wasn't a particularly good student in high school, to tell you the truth. Um, I was um, you know, I kind of like did well enough to get by with like high B's and low A's and without working hard. And then, you know, when I got to college, um, you know, I took my first chemistry test to tell you the truth. And then I I got I got a failing grade, which literally punched me in the mouth, right? Because I was like, okay, like how's you know, it really like bruised my ego because I was not used to that in high school. And um, and I didn't I went to a pretty good high school. It wasn't like, you know, I went to easy high school. But um anyway, I realized that I I can't do the same thing that I was doing. Right. And um, and and so that that like really kind of had a very, it was like a pivotal switch moment for me where I realized that I can't I really if I want to get good grades and I want to get into medical school, I and then and back then, you know, it was still like people still want to go to medical school and doctors were doctors are still making a lot of money and stuff like that. So um anyway, I uh I I I started working really hard. And that that was that was the kind of driver for me and and and and I and that and I took that work ethic through the entirety of of college and then it served me very well when I did my first startup when I dropped out of medical school. Obvious, I applied early to early admission to NYU. I always kind of thought I wanted to be a surgeon. Right. And then um, but but I did computer science really because uh when you're pre-med, it's not a it's not a major, it's just like a track that you have to do. And then um I was thinking to myself, what if I don't get into medical school? I need a fallback, right? And so that that was my fallback. And I actually ended up working like the last two years of college as a programmer on the side, making some really good money, um, at least for a student, you know, and I got a little taste of what it looks like to to um to make money. And then um, so I did go, I ended up going to to medical school uh at NYU and uh because I got into the early, early admissions program after college. And my roommate was a Goldman at the time. Okay. And uh he was a really smart guy too. I knew him from high school, actually. And he, you know, halfway through my first year, he would watch me study all the time, and he was going out having a great time all the time. He was still working hard, right? Uh but but you know, living a total like we couldn't have been living polar opposite lives being roommates. Right. And um he he's like, What are you doing, man? Like, we can start a dot-com. This is like 1998 or 1999. There was money swishing all over the place. The stock market was going bananas. Yep. Uh and they, you know, it was like free money, basically, at the time. He's like, you know how to program, I know how to raise capital, I have an idea. Let's let's do this. Um, he happened to hit me on a Sunday when I was studying, and you know, he he had already been out the whole night and just woke up in the afternoon. And I'm like, what the hell am I doing? Like, uh you know, he's right. You know, I I can I can always come back to this, but this kind of uh opportunity is a once-in-a-lifetime thing. Right. And so I had I had a little bit of money saved up from what I had been doing in the last couple of years in college. And him and I, he quit his job and I quit med school and we did a startup, and someone was dumb enough to give 22-year-olds uh you know, now they call it smart, by the way. Back then it was pretty dumb, but uh, you know, millions of dollars to do a startup. We we really the next two and a half years, we built an awesome startup. We were way ahead of our time. We created, we did uh we were basically like Microsoft 365 through a web portal using Citrix because there were no web-based apps at that time. Everything was like everything was Windows-based. We had we built in the cloud, we had an app store, we I don't know, we did all these things that we didn't have words for, right? Right, we didn't even know how to explain it. Right. We we explained it as like utilizing computing, like you pay for your computing, like you pay for your utility. Right. And and people were still buying Microsoft licenses then. It was a totally different situation. And so um we we were just we built awesome software that no one ended up using because we were too early.

SPEAKER_02 14:52

Right. So walk walk me through that moment, right? So you guys build this company, um, the stock market's going through the roof, then all of a sudden in 2000, just everything goes to hell, right? And and you go from, I guess, being worth a significant amount of money on paper to everything falling apart. What what would what take us back through those moments? What went through your mind? How did you process that when you went through that? What was that like? It sucked.

SPEAKER_00 15:18

I mean, I don't know what to tell you. Um I but you know, I was like really kind of my my my my roommate and we had another partner or two that that came in and they were like kind of like holding on. And and I saw the writing on the wall, and I'm like, guys, what are you doing? Like this is over, right? Like, you know, the the the we're not getting any more money. I had actually, it was like e-trade had just started like a year before. I started an e-trade account with a little bit of my money and had like amassed like this crazy amount of money in my e-trade account that literally went down below where I had put the money in. And I thought I was like a billion millionaire, billionaire. I might as well have thought I was a billionaire at that time. We were living in New York City, we were going out every night, you know, working all day. Sure. I was I I really did think that I was yeah, and then um, you know, I I think some people have a like a much better ability to see reality as it is, right? And some people don't. They they they think that they can do stuff to alter reality, which obviously um startup founders need to know as well, but you need to know how realistic it is that you're gonna be able to do that. Um and I was like, I saw the writing on the world, so I kind of left earlier than everyone else did, and I said, look, you guys want to stay, that's cool. I'm just I'm gonna I'm gonna step out. And I didn't really know what I was gonna do, but I just knew that that wasn't gonna work out.

SPEAKER_02 16:53

Um You talk a lot, you talk a lot in the book about self-doubt, right? And and and some of your challenges facing that. How how did that chapter impact your level of self-doubt or self-confidence, if at all? What what was the impact on you on that?

SPEAKER_00 17:08

Well, it was actually even worse because um I tried to get a programming job, which I couldn't get because basically every other startup was going out of business too. Um and so that backup plan wasn't working for me, if you think about it. Um So then I'm like, oh, maybe I'll just go back to medical school. But like I didn't want to do that because once you get a taste of real life and you know, the excitement of actually not having to work four years before you can actually do something. Yeah, yeah, you know, or study for four years or five years, or in in in in many cases you have to go through residency, which might be multiple years after that. So um, you know, I begrudgingly was like, okay, maybe I'll go back to medical school, but you know, that that's like a you know, I have to wait to matriculation the next year. Um I was embarrassed, honestly, to be uh so I didn't really tell very many people. I didn't tell my friends, I didn't tell even my mom uh in the I was like kind of trying to figure it out, you know, trying to just see if I could get a job. I I I was trying to save money. I moved in with my girlfriend at the time, so she was at a in a in a in a dorm. And so um that was uh that was a hard time for me because uh I just the solution wasn't so clear. I had to really go through the search for that.

SPEAKER_02 18:38

How did you get through that? I mean, you know, different people, like one of the things we talk about a lot in the show, and you know, I do a lot of keynote speaking and I talk about this all the time. It different people and successful entrepreneurs have just this crazy amount of resilience, right? And they're they're just able to get back up and get back up and get back up. And you know, most normal human beings can't do that, right? They can't find the strength to keep getting back up and eventually they go back to you know any old job or they or they you know figure out some something that does not involve you know the crazy amount of risk of being an entrepreneur. For you, what was this thing that allowed you to you know get back up, but not only get back up, but then you you started Junebug, right? What where did that strength come from?

SPEAKER_00 19:21

So, I mean, obviously it came from what I said to you before, you know, seeing my parents do it. And you know, they were in dire straits many times. Right. Um and and you know, they were able to kind of through their own sheer will and their hard work, you know, get through it. Um and you know, I I was lucky because I had a really good education. And so even, you know, I actually think that prepping for med school, even though I didn't end up going to medical school, really changed the way that I think and analyze things. Right. Um and so that that may have inadvertently really helped me. Okay. Because it made it made me very analytical, it made me think stepwise, it made me um confident in myself that I can solve problems. Um, because you know, even just getting into medical school is very hard, right? And it in and of itself. There's a lot of hard work, a lot of, you know, I was in um, you know, organic chemistry is no joke. Let's just put it that way. Yeah, not easy. Yeah, so so if I could do that, I could probably do things that are a lot less hard. Uh so I I it it it built my self-confidence over time. And and what even though I failed at the company, and the company failed, we successfully did a lot of things that made me learn. You know, like I learned how to first start a business, run a business, what it's like to do that, what it's like to have employees, what it's like to manage um groups of programmers, which is what I was I was a CTO. Right. And so, you know, and what it's like to hire people and all these other things. So it wasn't uh a big waste. Anyway, I just kept my eyes and ears open. I just kept, you know, putting one foot in front of the other, not to be cliche. I was I was going multiple paths. So I was I was talking to recruiters, I was applying to jobs, I was, you know, reapplying to medical school, I was um, you know, maybe looking for another startup idea at the same time.

SPEAKER_02 21:35

Right. So it sounds like it sounds like you had a couple of different things, just for the for the sake of the audience, right? Because again, you know what we're trying to do on this podcast is also teach people, you know, what are the those kind of pillars, what are the the support mechanisms that can get you through really hard times. And from when I'm listening to you talk, there's a couple of things that are emerging there. One is your ability to just do very hard things, right? So you talked about organic chemistry, like I don't even I won't even go. There because I like had a horrible time just with basic chemistry. So so you know, when you when you one of the things that you see in neuroscience is when people do hard things, even when they don't succeed, it seems like it just builds your confidence and it literally rewires your brain to be able to face harder things along the way, knowing that you've done these crazy things in the past, right?

SPEAKER_00 22:20

So it doesn't seem so bad in Retro.

SPEAKER_02 22:22

Exactly. Exactly. So that's one thing. And then um the other thing that you you seem to have learned at an early age as well, which which again I've I've seen this pattern with many successful entrepreneurs, actually with all of them, is your ability to kind of like reframe your failure as a learning, right? And take that and be like, okay, all this shit didn't work, but like, like you said, I learned how to manage people, I learned how to write code in a different way. We learned how to build systems, you know. So so it sounds like there was something there as well. Is is is that accurate?

SPEAKER_00 22:51

Yeah, absolutely. I mean, it was definitely a stepping stone. I don't think I could have successfully done my next startup independently, by the way, right? Without without those other partners, if I hadn't had that confidence to to have learned all those things that I did, and just it was a cinch the next time to start it, let's just say, right? Right. Um it wasn't a cinch, like it wasn't it like after I started it, it wasn't a cinch. But um, you know, just just like being like, oh yeah, I know how to do that. I'll form an LLC, I know this lawyer, I know this accountant, I know, you know, like I know how to hire people, you know, like all these other things that kind of um you know the that that you built the muscle to do, basically.

SPEAKER_02 23:37

So many people, like I always say, like a lot of people say, well, the thing that stops people from starting, right? Where it's like whether it's starting a new venture or or like moving countries or starting a new relationship, like so many of the things that I see is that fear is the thing that stops a lot of people, right? People are just scared, especially like you know, you know, you've been in a big corporate job for 10 or 15 years, all of a sudden they're like entrepreneurship, oh my God, and who's gonna, you know, how am I gonna pay for you know health insurance? And and what if I don't have a salary every day, right? So it's like fear stops a lot of people, but it sounds like from what you're saying, that it's like you didn't ever you never had an issue with the fear. It was more kind of like how do you build the muscle to keep going when things get really tough, right? It's like seeing it through to the end. So that brings us to June bug, right? So you land in the nightlife world, right? Uh most people most people would have like seen like parties and and cool venues, but you saw clearly something else. What what did you see in the nightlife world?

SPEAKER_00 24:34

So um the story is like how it really started is my girlfriend was working at a few nightclubs on the side just to make extra cash. And I would go and pick her up at like, I don't know, whatever, two in the morning or four in the morning, whatever it was. And um, you know, so she'd get home safe. And I'd go into these, like basically like these like dungeon, you know, offices in the back of the in the back of the bar and a nightclub, and everything was like pen and paper and passed backwards. It made no sense, right? And and and it wasn't just like one place that was like this, everybody operated the same way. And um, and then you know, I noticed that also they were giving out like flyers that basically everybody threw on the floor, and and I'm like, you know, there has to be, and there wasn't like a centralized place to know where where to go or what to do. And so, you know, I just I was like, you know, we need this this can be solved. Let me go. I actually went back to her dorm room, not my own dorm room, and I uh, you know, I started coding it. And I'm like, you know, let me let me see if I can kind of find a solution to this. And then obviously she had an in. So like, you know, the first couple of customers that I got and I showed it to them, I it was it was very easy because like, you know, I just went there and, you know, I just showed it to them. And they um and they were, they were, they were it's actually really funny that uh they're really early adopters. Um a lot of the people who are in the nightlife business, they're willing to do a lot of things that I I would say that most uh traditional business owners won't do because they're willing to take chances and do do. I mean, they they opened a club for uh for God's sake. They're willing to take chances. Yeah, you have to be entrepreneurial.

SPEAKER_02 26:22

Yeah, yeah, for sure.

SPEAKER_00 26:23

Yeah, yeah, you're willing to take chances. And then, you know, that's how it started. It started small. I remember getting like my first three thousand dollar check, right? Where someone signed. And like I thought I like I think the jackpot, right? Like, yeah, listen, I had made a lot more than three thousand dollars, but the feeling of someone finding value in what I had just made and giving me a three thousand dollar check to start to use the serve service was it was all I needed. That's amazing, yeah. To then go for the go for gold on it.

SPEAKER_02 27:00

What walk us, walk us back to that first client that you got? Because I think you mentioned in this in the book that you have something in the book about having to like, I don't know, create or or or or fabricate like a richer story of the company just to be credible with this. And and I think you referred to it like a master, a masterclass in BS or something. Walk us back through that moment. How did how did you actually do that? And how did you actually get that sale?

SPEAKER_00 27:23

So it was actually uh, you know, at one point we realized that um, you know, we we we could do it in an event because we had amassed uh so so we didn't just actually have the software infrastructure, we realized how much money they were making off events, and we're like, let's do our own first event. And this was early on that we figured out, and we were like, let's do it on Halloween. Okay. And we went to, there was a, I don't know, this was the most beautiful place at Queensborough Bridge. There was a on the Manhattan side, there was a restaurant called Gus Guastavino's, Gostavino's, it was a Terrence Conren um place. They they had spent, I don't know, like $10 million making this place. It was beautiful. It had vaulted ceilings. It was like um, and and this place was uh was beautiful, it was huge. And we're like, this this looks like the perfect place to do a Halloween party because it was vaulted and all these other things.

SPEAKER_02 28:14

You got the whole gothic thing going on, yeah.

SPEAKER_00 28:15

Yeah, yeah. And so uh, you know, I made some bullshit letterhead, you know, like and put like, you know, a Fifth Avenue address, which I got from, you know, they they had these like P.O. boxes or mail services that you could like share get a Fifth Avenue address on it, and um, you know, had my cell phone number, but my cell phone number was a two-on-two number, so it looked, it looked really professional at that time. Right. And um, and you know, made this whole proposal and um, you know, went in there and just kind of like acted like I should be doing this. And we had a lot of experience doing this, and you know, just bluffed my way into getting the contract. And um, you know, they were like, we want to put it, you we want you to put a deposit down. And like I gave them, I gave them a credit card that if they actually ran, yeah, they would have bounced. Yeah, but like I figured like maybe they won't run it, you know. And so, so I just gave them a credit card and they took a photocopy of it, but thankfully they didn't run it. Right. And um, you know, we got our first thing and we got our first event, and we ended up doing really well on that, and then on that.

SPEAKER_02 29:31

So it sounds like you really embraced the age-old philosophy of fake it till you make it. How how how important is that for entrepreneurs to be able to pull off that kind of bravado and and believe that they're something bigger than they are? When in reality, they have nothing but a slide deck, or in your case, you know, this this drawing with a fancy letter head and the P.O. box. How how essential is that for entrepreneurs to be able to think and act that way?

SPEAKER_00 29:57

Um, I think it's it's crucial. I mean, they have to be able to um imagine the world as they want it to be and and and and will it to become like that. Um and um, you know, unless you're delusional, you're not gonna start another, you're not gonna like if I and I this what I'm saying is being said by many other entrepreneurs, and you, you know, I I hear it on other podcasts too, because like obviously my situation isn't unique, right? Right. Um, you know, if I actually knew what I had to go through in a 10-year period, I don't know if in retrospect I would have actually done it. Yeah, right. Um, I had to be a little bit delusional of how easy it's gonna be and you know uh how things are gonna work out and how much work I'm gonna have to do and all these other things to be able to you you almost have to be a little bit naive, right?

SPEAKER_02 30:54

Um what else do you have to do to stay on the path? Because obviously you said, yeah, it's a 10-year journey. And when you look back on all the crazy things that happened, you know, you don't know if you would have done it. I'm walk us through a little bit the psychology of what it takes to stay grounded and keep going.

SPEAKER_00 31:10

You know, honestly, I think that the the the best analogy is and is is is and and I'm understanding it now that I am one is parenting, right?

SPEAKER_02 31:20

Interesting.

SPEAKER_00 31:21

You can't, you can't, like no matter how tough it gets with your kids, you can't just let it go, right? You have to, you have a responsibility and you have your responsibility to do the best and you want to do the best. And you know, if you kind of think of your business that way, um you'll go to the ends of the earth to make sure that it survives and it thrives and it does all these other things. I mean, it's the best analogy that I can think of, really. If if you truly believe that this thing is your is your child or your baby or is is it is a piece of you, right? Then you will um you'll treat it that way.

SPEAKER_02 31:58

It's interesting that you say that. And I and I agree with you, right? I mean, but but it does beg the question, and you see this now as an investor, right? You've invested in over 50 companies, you know, some some notable successes. Why do so many startups fail, man? I mean, like obviously there are many different reasons, but but but what's like the main reason why you see a company that has like all the talent, that has the tech, that has the the smart guys or girls running it? What's the number one thing that kills startups?

SPEAKER_00 32:23

I think that, well, for with me, it was obviously a great idea, just too early. And timing is very, very, very, very important.

SPEAKER_01 32:32

Yeah.

SPEAKER_00 32:33

I think that um a lot of startups, especially ones that get a lot of VC money, um, they lose their sort sense of urgency.

SPEAKER_02 32:42

Interesting.

SPEAKER_00 32:44

And um, you know, one of the things that kind of made me is like this paranoia, right? That that, you know, so you know, I'm not gonna do it faster. I always wanted to do things faster and faster. Right. And and and uh I've seen that happen with um with too many, too many companies. Um, I've also seen it where um you know the the the founder is um too focused on the wrong thing, like they haven't found the the thing, the lever that is the most important in our business. Right. Um and they keep going down the wrong path of what what they think the lever is. Um and um uh obviously I also think that um to some degree you have to be stubborn, but at some point you also have to be coachable. Right. And um, and and you know, I'm not saying you have to listen to everybody. You have to listen to the right people and you have to understand who the right people are to listen to. Uh but you know, you you have to learn to change and adapt when when is needed. And um, you know, founders have a hard time doing that.

SPEAKER_02 34:01

It's it's a really it's a very interesting point, Shane, because I think you raised something that I think, you know, few people really understand is that fine balance between the stubbornness to keep going, which you need to if you're gonna do, you know, the full marathon, right? Which this is, but then also the realization and the self-awareness that there are times when you just have to pivot. So I think, you know, for the folks out there that are in the middle of this, right? I I was having dinner with a dozen entrepreneurs in Miami last night. They are in the thick of it right now. You know, one of them had raised, I think, 55 million. Um, how do you find the sweet spot between sticking to your vision and knowing when to adapt and who to listen to?

SPEAKER_00 34:41

That's an art. It's not a science. Um, I think it comes down to your decision-making skills. And that's a hard thing to do. Yeah. Um, it's very hard to be a good decision maker. But for me, for example, I even I I I took I talked about this on another podcast recently. But, you know, I took a decision-making course a couple years ago. Interesting. And and um, I thought I was a pretty good decision maker until I took that course. Then you're like, oh shit. Yeah, I'm like, I've been doing this all wrong. Uh you know, I think you have to have a crazy amount of self-awareness and you have to have very little ego. It's very hard to um, it's very hard to to do that, especially when you're young.

SPEAKER_01 35:30

Yeah.

SPEAKER_00 35:30

Uh, you know, uh the younger guys, uh girls, they, you know, they they tend to think that they're always right, and maybe older people don't know what they're talking about. As a practical matter, as a VC now, I don't even bother giving advice because, you know, the reality is if I have to give you advice, I shouldn't be uh really investing in you for the most part. You know, I'm happy to give, you know, small advice here and there or help um make connections and that kind of stuff. Um I think that uh, you know, probably my advice is irrelevant now. You know, I haven't done this in 13 years. Sure. So much has changed. I could be telling you the totally wrong thing anyway. You know, like what was right for me 13 years ago might not be, you know, right anymore. And so um that's that's another thing. Like, you know, you should you should you should realize that and who you're talking to and how much they really know and whether they really are an expert in what they're talking about, right?

SPEAKER_02 36:29

Give your take on this. I mean, and you you you you said something that was very interesting there, right? Is you haven't actually done this in 13 years. And yes, you know, there's some things that definitely change. The technology changes, you know, the consumer mindset maybe changes a little bit, uh, competitive landscape definitely changes. How, what's more valuable to an entrepreneur? And obviously, this is probably context-dependent, but what's more valuable if you're an investor today, you've invested in a company, is it more valuable to try and give advice based on your experience that might be relevant to the entrepreneur? Or is it more valuable to just slow the entrepreneur down by asking them the right questions so that hopefully they can come to the realization on their own?

SPEAKER_00 37:09

Um, obviously it's preferable if they come to the realization that themselves because then they kind of think if it's it's themselves that that did it. So um I I do like that technique a lot more. Um I also don't like offering advice unless I'm asked for it.

SPEAKER_02 37:27

Um why why not?

SPEAKER_00 37:30

Um it was just it was annoying when I was a founder. Like I like, you know, I was always like, dude, if I needed your opinion, I would have asked you, right? You know, that kind of thing. Uh so like I don't want to be the annoying guy that, you know, or investor that that that you know, and I that that that that founder probably has better things to do than read like an essay that I write to them uh or something like that. So um I I tend to be like as hands-off as they want me to be. Um and so that's um that's that's my that's my advice and that's my style.

SPEAKER_02 38:09

Interesting. Let's let's let's let's switch lanes for a second. I want to talk about you know the accidental empire uh in your book, uh easy texting. Yeah. It it seems like it started as an in as kind of like an internal tool, right? As something that you built, you know, because you needed it. And then all of a sudden you get a realization that like, holy shit, there's like actually a business behind uh behind this, right? Yes. Walk us back to that moment. How how did you come to that realization that this could actually be a significant business? Well, and maybe tell people a little bit about, you know, tell people a little bit about easy texting as well for those who don't have time.

SPEAKER_00 38:47

Yeah, so so one of the things that we did at JuneBug is we had a uh you know a marketing stack that we that that that a lot of um that we used and a lot of other uh clients used. Basically, it was like email marketing, right? Kind of like MailChimp, the EC. And um we had our own email list that that the people would send uh promotions through, and then um and then we would use it for ourselves. And as time went on, uh the efficacy of that really, really started to dwindle because of social media, because of um now they were getting 10 emails, maybe a hundred emails. They were getting one from the nightclub, from the DJ, from the promoter, from the grandmother of the promoter. The promoter's girlfriend. Yes, yes, you know, and so we were like not the only game in town in your inbox anymore, which which really kind of so I was trying to figure out a way to kind of cut through the clutter, and this is 2005. Um, and you know, Blackberry, I started I started using a Blackberry and and texting st started to, you know, because you had a keyboard.

SPEAKER_02 39:57

And so I I had a bold, I remember those days. Yeah, I loved my Blackberry. Um it's still the best device I've ever used to text on, to be honest. I still hate typing on my phone now.

SPEAKER_00 40:07

Yes, well, you should use a text of speech, not Siri. There's a bunch of other ones that that are much better. Yeah. Um but anyway, uh, you know, I'm like, wait, how about if we send a text message to people? We have their emails, we have, but but we have more phone numbers than emails because back in the day, people used to have clipboards and they would go around in the bar or nightclub and you know, you put your phone number down. Exactly. I remember those days. They used they used to call you. They used to literally call you and uh and tell you, like, oh, we have DJ so-and-so coming or whatever. Right. And so um, so uh it wasn't as straightforward as I thought it would be because you know it's the telecom systems, it's not the internet, it's something different. Anyway, I I figured out how to how to do that in 2005. This is way before Twilio existed, by the way. Yeah. So um, this is like years before Twilio existed. And and then, you know, we built this internal system and we send out our our our first text message. Look, on our list are other entrepreneurs and other other um other promoters, club owners, like whatever they were, and they get the text message. And my phone starts, it didn't come the it didn't come from the phone number of my phone. It came from what's called a short code. But everyone knew who it what it was because it said like it said June June Bagana. And my phone started to like blow up because they're like, How did you do that? Right? Yeah, and that was the aha light bulb moment. Ah, of course. Like, oh my god. Yeah, I I might have just stumbled onto something that like all these other people want and need. Right. Um, and then and then we quickly started pivoting to kind of separate that out from the company, make it into, you know, initially I had like a pretty janky tool that I just used internally because I was just using it myself, right? Like I didn't need a fancy inter interface or anything. I coded it myself. And then and then I'm like, okay, let's make this into like its own SAS where you can take a credit card and and then you can like upload your own phone numbers and you know, do these other things. So that that was the genesis of easy texting.

SPEAKER_02 42:19

And so it it this thing starts to just take off, right? And you're creating like arguably one of the first like early real SaaS companies.

SPEAKER_00 42:27

Um I think I well, not SaaS, but but SMS companies. SaaS had been around uh prior to 2005. But but uh uh you know, like a mail chimp for text messaging did not exist. I at least I couldn't figure out where to find it doing exhaustive Google searches. From my vantage point, we were the only game in town, and honestly, we dominated search and and and and SEM to the point where I was actually scared that people were gonna like compete with us. So this is crazy. I talk about it in the book too. But what I did is I I made like other white labels of our software with different names and then ran campaigns against myself because I I wanted people to think that there's like real competition out there and there isn't just one company. Right. Um, which which worked for a little while, but then you know, after a couple of years, it was like shooting fish in a barrel for a couple years, just really honestly. I if I if I told people like what we were paying per click, I mean we're paying like five cents per click.

SPEAKER_02 43:39

Yeah, I remember you mentioned that in the book. I think it was like four or five cents per click, and everything is going gangbusters until something really bad happened. You do you wanna do you want to share that story with us?

SPEAKER_00 43:51

Well, there were a couple bunch of times where the bad things like we had our servers like totally like die on us and we had to rebuild. Life before AWS. Yeah, yeah. And then we had uh, you know, there were there were like, I don't know, countless moments where I literally wanted to rip my hair out and I thought I was out of business. But um the the the big the mother of all of them was when T-Mobile shut down our number. And um and yeah, and that was uh that was a big, that was a really big scary time for us because I mean think about it. Imagine if someone sold you a phone and they're like, you know, you can um you can call anybody except for people on T-Mobile, and they can't call you either. Like, would you ever buy that phone? You never buy that phone, right? So it was it was essentially that's essentially what was going on, right? Like we had no uh way of texting uh T-Mobile people because they unilaterally decided that they didn't like what we were doing.

SPEAKER_01 44:48

Yeah.

SPEAKER_00 44:49

It had to do with uh just we had a customer that that was a um like it was a medical marijuana dispensary mapping system where they would just basically just tell you where the medical marijuana facilities were.

SPEAKER_02 45:01

Oh, is that was that weed maps by any chance? Yeah, yeah, it was weed maps. Oh my god, small world. I did some work with those guys.

SPEAKER_00 45:08

Yeah, yeah. It was it was like the early days, like 2006, 2007, or whatever, and they just didn't like that content. If you can imagine that like a a carrier cares what content is on the text messages that go to it, wasn't even a problem of like these people didn't opt in and they were sending them spam text messages. That wasn't the issue, which which what it wasn't the issue. The issue was they just didn't approve of that content, if you can imagine. And so um I had my back against the wall, and um it was a David and Goliath kind of situation. Uh, you know, we were still pretty small at that time, but I'm like, at that point, I'm like, I have nothing less to lose. I might as well just spend the rest of the money litigating and figuring out that I had left at that point. And um, you know, tenaciously found the the one guy in telecom who understood what we did because it was so nascent and new. Yeah, you know, hired the best lawyer I could get. It cost me an arm and a leg. I probably couldn't even afford it at that time, that time, you know, um within like a month or so. Uh and then and then, you know, like I worked the PR angle through my contacts and like kind of got this. It was a story because like, you know, just that idea that that that that uh uh someone's shutting you down because of the content, uh especially weed, you know, at that time, yeah. Um or medical marijuana, right? And so uh it started getting like news and like on on the TV and stuff, and then so like they were willing to come to come to the table and like talk to us, and uh and it's finally they settled and shut us back on. Right. Um that was a big victory. Big victory. Not just for me, but everybody in my industry, actually.

SPEAKER_02 46:59

Exactly, exactly. And it it it it's so it's a testament to something that you talked about earlier, Shane, which is the adaptability that you have to be to be an entrepreneur, right? Because, you know, if I remember the book correctly and what you're just talking about now, it's like you you kind of became like a lobbyist, you kind of became like a you know knowledgeable about PR and petitioning the FCC and you know, you had to wear so many hats to make this work, right? And so what did that what did that experience teach you about what it takes to be an entrepreneur?

SPEAKER_00 47:29

Taught me that um that's you know, it taught me, you know, that that that you have to be able to withhold, you know, withstand, sorry, not withhold, with withstand just tremendous amounts of pain, emotional, psychological, um, you know, when when all is lost, you have to find something in you to continue. Because I genuinely really thought at that point I would have to fire everyone and and close shop, and it which really sucked because we were doing so well. Yeah. And and um, you know, I it just taught me also like to to um I oh by the way, the the thing that it really taught me is always put the best people around you. And and and like, especially when it comes to like a lawyer, accountant, those types of things, you cannot cheapen out.

SPEAKER_02 48:24

Yeah, you can't cut corners, yeah.

SPEAKER_00 48:26

You can't cut corners, even in the beginning. Actually, when you cut corners in the beginning, and uh like a lot of entrepreneurs want to do, and you you set yourself up incorrectly, that can cause a lot of issues for you down the road. And I I was a victim of that too, because you know, for other reasons that, you know, it's too too long to go into, you know, you you just can't cut corners no matter how much you want to. Um that's that's also and you have to be willing to put in the work. Like I lived and breathed it, you know, like I would stay up till like four in the morning, you know, trying to figure out ways to to to you know to solve this issue.

SPEAKER_02 49:04

What do you think had to change in you to see these these these ventures through to the end? I mean, what what what kind of belief in yourself had to change to ultimately get easy texting to be a viable business and to you know to eventually you know exit the business?

SPEAKER_00 49:21

I mean, I don't think I think the the belief was I had no other choice. Like like it was just like there was no choice other than to figure it out. Like I I don't I didn't even consider, you know, like I you know, I had the fear of I think maybe the better way of me saying it before was, you know, I was afraid I'd have to shut everything down. And I knew that that was one of the paths of possibility, right? But like I I couldn't make that an option, right? That path was not an option for me. It was it was I was aware of it, but I feared it so much that it was not an option for me, right? So I I think that that's um that's the way you have to kind of think of it. It's like, you know, I I was willing to do whatever it took to not have that option become a reality.

SPEAKER_02 50:13

Fast forward a little bit to your decision to eventually sell the business, right? And and then, you know, you this next chapter on moving on to becoming an investor. One of the things that I have found, you know, with with post-exit founders is, you know, that the hardest thing about making that transition is that you essentially have to shift identities. And and so many entrepreneurs, their identity is tied to the business, right? So the very thing that allows you to keep going and be successful in the face of all this shit that you go through ultimately is the thing that to some extent you have to let go when you decide to sell the company and maybe move on to a new phase in your life. How did you navigate that transition when eventually you decided to become an investor and get and get out of operating and building startups?

SPEAKER_00 51:01

Um so for me, it was um, you know, I had the right offer where they gave me enough capital to like I was like, okay, you know, to make this amount of money, I'd have to work another eight years, right? And is that enough? Right. And so um, you know, I could have probably gotten more. And obviously if I had waited, you know, I sold my company in 2000 I think 13, uh, or it was either the end of 12 or 13, I don't remember. And and um, you know, if I had just waited just like three more years, I I could have gotten a much bigger multiple and all that kind of stuff, but I wouldn't have been um a present father. I would have, uh you know, I would have, I would have had a totally different experience in life. I would have never moved to Miami. There was so there were so many like a chains of events that would have never happened that I'm so grateful for, let's just say. So for me, uh, I didn't know what I was gonna do afterwards, but I knew that I was ready to kind of move to the next chapter of um, and I didn't want to to operate in a new business. Um I didn't know exactly what, you know, it's they say this like all the time, like you're willing to kind of go into something not knowing how it's all gonna come together, but being confident in yourself enough that you can figure it out over time. And so initially I just my my my first goals were to, you know, complete the transition. I stayed on board for a year, helped them, you know, help them get the get the you know get on their feet and turn learn learn the business and everything like that. And then just kind of being a present father and like doing all these things that I missed out on. And then uh and then eventually um, you know, getting the itch again. And and then, you know, because like you could you can only kind of have downtime for a certain amount of time when you're when you're really uh entrepreneur before you kind of like your mind starts racing and you start thinking of new things to do. And um, you know, I I there were a lot a bunch of times where I was like kind of going down that path and I had to pull myself back from from you know, from from going too far down that road uh of maybe starting something new. And then uh eventually I kind of found my mojo in, you know, learning. Once you start learning how to do things that are hard, like you just said, like, and it was very hard for me to learn how to invest. I had to go through multiple um wealth managers until I found one that was willing to teach me and was my style. Um, you know, I learned about real estate, I got my real estate license, even though I never sold a piece of real estate in my life, you know, but but you know, I I just wanted to kind of learn and and and be aware and understand it. And um, you know, you you tend to like things that you start to get good at. And so uh, you know, that's when I kind of like I started building my investment muscle through that, basically.

SPEAKER_02 54:05

Was there was there a particular moment uh towards the end at that Easy Techs where where you just were just like, maybe it's time to move on to a next stage? Was there a particular moment that you can recall where like I really need to make this transition and let this go?

SPEAKER_00 54:21

No. I mean, I think if I wasn't approached, maybe I wouldn't have um, you know, I I may have just kept on going. Um and you know, I I always had it in the back of my head at one point. I I I needed to either replace myself, like get a replacement, which seemed even more of a daunting task than selling. Right. Really, really hard to do that. And um, you know, I I I kind of knew I needed to do that, but this other option, which I never thought about, can't came knocking. And I was like, wait, maybe that's a good solution here, basically.

SPEAKER_02 54:58

And you know, you've said kind of like pedigree doesn't matter that much to you now as an investor when founders pitch you, right? Kind of switching hats a little bit. As an investor, what do you actually look for when when when somebody pitches you an idea, comes to you with a company that they're working on? What what's what's the difference between the people that you get excited about and really want to invest versus the vast majority where you pass?

SPEAKER_00 55:20

Um well, first of all, they have to be able to tell me what they do in just a few sentences. Right. And and and be able to pique my interest in that in that few sentences. Um, you know, obviously if they're pitching me something that's totally out of whack for me, I'm never gonna look at it, right? Like if someone sends me, I don't know, a deal that's not in my wheelhouse, it just makes no sense. Um so so the first thing, first things first is like send me something where it's interesting and and I can understand it in like just a few sentences. And when when that happens, then my next thing is who is this person? And then and then that becomes the most important thing. Um so I you know it it's it's almost like flips. So if if that person can get get get my interest with what they're doing, then then what they what they're doing actually becomes irrelevant. It's it's weird to say it, right?

SPEAKER_02 56:18

Right, right.

SPEAKER_00 56:19

It it becomes more about them, right? Because they they hook they hooked me at that point.

SPEAKER_02 56:24

Right. So you're investing in the person, not so much in the idea.

SPEAKER_00 56:28

Absolutely, absolutely. Um I'm very much like that. Um and and especially when you're doing early stage investing, because uh, you know, like you're not you're you're playing poker without seeing the rest of your hand.

SPEAKER_02 56:44

Yeah, very true. Very true. Are there are there are there flags that you look for, you know, um when investing? What are what are the up what what are the what are the flags that most investors miss that will tell you this isn't the right investment for me?

SPEAKER_00 57:00

There's no foolproof way, right? There are general guidelines, and I've been wrong, you know, like like for example, I was this close to doing a very big investment in Grok. And you know, they had a really big exit recently. And, you know, I went almost down the road all the way, and you know, there's no reason for me to tell you why, but you know, it just didn't I didn't do it, right? And my my guidelines didn't work for me then. There are many times where my guidelines did work for me. Um so no, there's no foolproof way, but I think and and it's like it's like buying stocks, right? Same thing. There's no foolproof system of buying stocks. Uh so I think that um, you know, for me in general, like I said, I want I want a very independent founder who um, you know, it in fact, actually for me, sometimes people don't look at um founders that you know had um, let's say failures uh before. You know, that they're you know post-exited founders that had real meaningful exits, they get much higher valuations because there's this thought that they could do it again, right? And so I think one of the things that's overlooked is that founder that may have failed because COVID crushed his company, or he was too early, or there was these other things that were out of their control, but got back up and did it again, they're almost even better, I think, in some cases. So that's something that I like more.

SPEAKER_02 58:36

Interesting. If you if you had the choice, a founder who has had one or two failures versus somebody who's had one or two successes, which one do you choose?

SPEAKER_00 58:45

It depends on why they failed.

SPEAKER_02 58:47

Okay. Fair point.

SPEAKER_00 58:48

It's uh it's it it really, really Yeah, absolutely. It really, it really is. Um it's more nuanced than that. Of course. And it also depends on why the other guy won.

SPEAKER_02 58:58

Yep. Very true.

SPEAKER_00 58:59

That that guy could have just been on the right place, right time with with the right co-founder, right? And they didn't do much.

SPEAKER_02 59:06

Very true.

SPEAKER_00 59:06

So there's there's a lot of different uh there's a lot of different nuances in this. Uh I think uh, you know, for me, the things that I'm also looking for is like, does the does the founder really truly understand the problem that they're solving? And that's um that the only way you can do that is really uh and I do this, I'm not sure how many other VCs do this, but I actually go and you know, and maybe spend two weeks with them and I go to their office and maybe a week or whatever, I actually like meet their team. I, you know, I get to know them to the degree that they'll allow me to do this. Um, some places they won't allow me to do this, but to the degree that they do, I'll pick up phones or I'll get into a scrum session with their with their developers or whatever it may be, um, to really deeply understand their their company and understand whether or not they really know what they're doing.

SPEAKER_02 1:00:02

Last question before we we move to our lightning round of questions, which is which is the the wrap-up. Um, with all the experience and all the hindsight that you have as you know a multiple exited founder and a serial investor with with a notable degree of success. And and the book, you know, uh, because obviously the book is always a great way for us to kind of psychoanalyze and give ourselves a lot of therapy on on what we what we did well and not. Uh, what advice would you give your kind of 32, 33-year-old self today if you could?

SPEAKER_00 1:00:36

Oh get that full night's sleep because you're worried, you're worrying about nothing.

SPEAKER_01 1:00:41

Yeah.

SPEAKER_00 1:00:42

You're worrying about all the imaginary shit that's in your head. Um that, you know, the all the different outcomes that you're like trying, and and you know, you always envision the worst out. For me, I was always like, I hope for the best, but always envision the worst. Yep. And and you know, Tim Ferris kind of talks about this a lot. Uh where and I think some people just have this in them, some people learn it, where he has like the fear board where you kind of like live through your fear. Yeah, fear setting. Yeah, and then and then like, you know, like whatever transpires usually is never as bad as what you thought it would be. Yep. And and so like it just doesn't hurt as much when it happens anymore. Or even when it, if it is as bad, it you already kind of live through it. So it doesn't, it doesn't hurt you as bad, right? And so um, you know, I just did that to too much of a detriment to myself, I think. And you know, I I lost a lot of sleep. I probably shaved a few years off my off my off my lifespan because of it. Um just really um, you know, it's hard, it's hard to emotionally regulate yourself when you're dealing with so much so many stressful things at one time.

SPEAKER_02 1:01:57

Yeah, it is. You really have to, I think one of the things that I learned, and and I learned it unfortunately as I was much older, even even you know, one one of my companies went under. I I remember that even no matter how bad things got, I always got a good night's sleep. And people were like, How the hell were you able to do that? And I was like, Well, you know, first A, I need my my six, seven hours, otherwise I just don't function at my best. And I intellectually know that, and I have, you know, as you get older, you have enough self-awareness to know that you you need, you know, gas in the tank. Um, and then B, I think the other thing that I learned through a lot of faith, um, spiritual and otherwise, was just there's just so much stuff that you can't control, you know, and and so you can't worry about it, right? You worry on what you can control, you do what you can on what you can control, and what you can't, you can't. Um, when I work with founders, actually, I use Tim Ferris's fear setting exercise in the work that I do. So I have people go through and I get like, okay, write the fear in a lot of detail, like what exactly you're afraid of. And then the next column is, okay, what are three things that you can do to prevent this from happening? And then the last one is, okay, if the shit hits the fan, what are three things that you can do? And just the exercise of having a founder go through that and write it and intellectualize and process it and then share it with somebody else, which is what I always encourage people to do, is okay, now that you've written it, share it with two or three people that are close to you so that they can play this back to you. Oftentimes people will realize that the fear was overblown and that they have more control over that than they thought. But you have to go through the exercise. We are really our our worst, our own worst enemies at times.

SPEAKER_00 1:03:25

So yeah, absolutely. I I feel like some people just automatically do that. I tend to automatically think the worst and go through the worst scenarios. Exactly. Uh but yeah, yeah. It's uh Well listen, Shane, this is been a great exercise.

SPEAKER_02 1:03:39

It is, it really is. It's very helpful. Um, you know, I I'm conscious of time, so I want to jump to our last three lightning questions. These are three quick questions, three quick answers. You know, we have all the all our guests go through it. Uh they're always kind of quirky. So it's uh I'm curious to see what you what you say. The first lightning round question is if you could have any one superpower, what would it be?

SPEAKER_00 1:04:02

Wow. Um maybe to read thoughts of anyone to meant reading everyone else's thoughts, maybe.

SPEAKER_02 1:04:09

Yeah, no, that that would be a cool one. Second one, second lightning round question. If you could have dinner with anyone in history, alive or dead, who would you choose? Oh, Elon. Okay. Yeah, that's uh that's a I love Elon.

SPEAKER_00 1:04:23

I love him.

SPEAKER_02 1:04:24

Yeah, I know.

SPEAKER_00 1:04:25

It's probably like too cliche. I mean, he's just, you know, he's he's he's he's he's one of a kind.

SPEAKER_02 1:04:31

Yeah, he is, he's absolutely remarkable. Um and last but not least, you know, if you had to give advice to a young person starting their career and looking to have a career that gives them meaning and purpose, what would you tell them?

SPEAKER_00 1:04:45

I think the best skill that you can ever hone is decision making. It is the most important decision, the most important skill more than anything else, is being able to make good, sound decisions consistently. It's actually what makes good VCs and good investors is that it's it's it's but more importantly, um, you know, making good life decisions makes a big difference in your career. Um you know, who you choose as your partner, whether, you know, there's your husband, wife, whatever, your partner, whatever your life partner, um, that's a big, you know, people underestimate that a lot. Um, you know, for me, my wife, integral part of my success, uh, absolutely. And and uh having that kind of support system, um, you know, choosing where you live even, or or you know, these types of things people don't really understand. You know, like where you live, it it makes your luck, right? Like if you want to be in a certain industry, you should be around where that industry is, right? Uh, because it'll just increase your your chances of you know finding. that stuff or finding people that are in in that industry that can help you or that kind of stuff. So just just learning how to make good decisions consistent consistently. If you think about it, no one really no one really teaches you how to do that. We don't teach you in school how to do that, just like they don't teach you how to do your taxes. It gets even deeper than like what constitutes a good decision. Can you even define that? Like these are these are some some things. And that's my advice to that to them is that you know sometimes the most important things are not um you know the things that are so obvious to you. Like going to Goldman or going you know if you want to do a night business or going to Harvard or going to these other things. You know? Yep. Absolutely yeah it's it's it's it's more things that um that that that that that you overlook that that are more important.

SPEAKER_02 1:06:57

Shane thank you so much this has been a great conversation you know I think um you shared a lot of different perspectives you know as as a as an entrepreneur you know uh all the all the stress that you go through all the things that you learned along the way you know your personal history you know before your entrepreneurship route and and the early growing up in in uh in New York and what that was like um you know building building uh June bug building easy texting going through everything that you've done pivoting now to to the the career of investment that you that you have you know I really appreciate your honesty and openness and sharing some of these things with us. Obviously your book is is is a really entertaining read uh which which which I think helps you know because of its degree of honesty uh and and and you know the stories that you go through and the willingness to talk about these things. So you know these are the kind of stories and conversations that we need to have particularly for those people that are you know new entrepreneurs out there building their first company going through tough times you know you you talk about that very openly so um so folks you know if this conversation resonated with you make sure to give it a like drop us some comments as well subscribe to the channel if you haven't already this has been another episode um of Morgue Unfiltered and the story of Shane Neiman. So uh Shane thank you so much for being on the episode today. It's been a pleasure and thank you around man thank you.

SPEAKER_00 1:08:13

Thank you this was super fun. Thank you so much.

SPEAKER_02 1:08:16

Thanks again man