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Ep 10 - From Paperboy to Payroll Prince: Meet Rob Basso, the Consummate Entrepreneur

Episode Description

Welcome to the Crazy Wealthy Podcast! Jonathan interviews Rob Basso, a seasoned entrepreneur and business coach who shares his journey from humble beginnings to building and selling multiple successful businesses. Rob's journey is truly inspiring. We dive deep into his experiences founding Long Island Advantage Payroll and his subsequent business ventures. Rob opens up about the challenges he faced, including a difficult split with a business partner, and how he overcame them. For all you entrepreneurs out there, Rob shares invaluable insights from his book "The Everyday Entrepreneur" and discusses his current work as a business coach. Whether you're just starting out or looking to take your business to the next level, this episode is packed with wisdom you won't want to miss. Tune in!

 

IN THIS EPISODE:

  • (00:00) Introduction
  • (01:50) Rob Basso recounts his early life and the entrepreneurial lessons learned
  • (05:21) The creative job-seeking strategy that launched Rob's career in the payroll industry
  • (08:19) Rob discusses his book "The Everyday Entrepreneur" 
  • (09:30) The "Triple Threat" of Entrepreneurship
  • (13:07) Post-exit challenges: Navigating the emotional impact of sudden wealth
  • (26:40) Overcoming partnership disputes and preparing for a successful business exit
  • (35:50) Rob's current role as a business coach and consultant
  • (40:37) Recap of the episode with Jon and Amy
  • Early experiences, such as having a paper route, can instill valuable entrepreneurial skills like responsibility and customer service.
  • Entrepreneurial success often requires a combination of ambition, confidence, and conviction, coupled with years of persistent effort.
  • The emotional challenges of post-exit wealth can be significant. Having a solid financial plan and advisor is crucial for navigating this transition.
  • Business partnerships can present unique challenges. Clear communication and aligned expectations are essential for long-term success.
  • Personal branding, particularly on platforms like LinkedIn, is increasingly important for CEOs and can significantly impact company value.

Disclaimer: [00:00:00] The following podcast by Fusion Family Wealth, LLC Fusion is intended for general information purposes only. No portion of the podcast serves as the receipt of or is a substitute for personalized investment advice from Fusion or any other investment professional of your choosing. Please see additional important disclosure at the end of this podcast.

A copy of Fusion's current written disclosure brochure discussing our advisory [00:00:15] services and fees is available upon request or at www.fusionfamilywealth.com.

Voiceover: Welcome to The Crazy Wealthy Podcast with your host, Jonathan Blau. Whether you're just starting out or are [00:00:30] an experienced investor, join Jonathan as he seeks to illuminate and demystify the complexities of making consistently rational financial decisions. Under conditions of uncertainty, he'll chat with professionals from the advice world, [00:00:45] entrepreneurs, executives.

And more to share fresh perspectives on making sound decisions that maximize your wealth. And now here's your host.[00:01:00] 

Jonathan Blau: Okay, good morning and welcome to another episode of The Crazy Wealthy Podcast. I'm excited actually today to have my friend and um, a mentor to many in the business world of entrepreneurship. [00:01:15] Rob Baso. Uh, Rob, welcome to the show. Thanks for having me, Jonathan, and what took so long, uh, you know what, there, there were just, um, there were too many options and I wanted to make sure that by the time you came on, I had [00:01:30] some sort of following because you're just too good to waste on, on the, uh, on the show when we only have two or three followers, which is my wife, my wife, and my two daughters.

So now that we've got. My mother-in-law on, I figured now, now we [00:01:45] can Appropriate. 

Rob Basso: Well, I'm glad to be here. Thanks for having me on, Jonathan. 

Jonathan Blau: Thank you, Rob. So, so I, you, you and I like my, uh, guest two podcasts ago, Cheryl Penny, [00:02:00] have some things in common that, um, that are interesting as it relates to, uh, the narratives about how we grew up and, and the narratives that people would normally associate.

With people like us who succeeded as [00:02:15] entrepreneurs and, and became, uh, be, became successful. In their own right. In other words, we didn't grow up with, with a lot on the table to begin with. So I always love those stories because I relate to them selfishly, but I think the audience [00:02:30] does too. So I'd love to start by, by sharing, um, your story.

You founded, uh, long Island Advantage Payroll. You, you, you made it very successful competing, I guess with the likes of a DP successfully, and, and then brought it all [00:02:45] the way to, uh, to a, um, monetization event. Now, uh, your post monetization, I guess, for the last five years or so. Um, and, and living, living life.

Uh, well, so I'd like to kind of take the audience from the, [00:03:00] from your, your relatively humble beginnings. Uh, how, how you got to where you got, uh, and, um, and I guess why don't we start with the, with the story that we recently, you and I recounted about, uh, about, um. Start with how you grew up and [00:03:15] then take it to the, uh, working in the deli story.

Rob Basso: Well, I'll, I'll give you the short version, uh, the, the short version is, yeah, I, I grew up actually outside of Philadelphia and South Jersey and. My parents got divorced when I was very young, and, and, and what I'm finding is that's a [00:03:30] common story a lot with successful entrepreneurs and you know, looking back over those years, I think it's, you know, an early life that you, you had to be resilient and figure out how to do things.

On your own. I had a, you know, single mom [00:03:45] with three, you know, teenage boys at one point. And you know, I had to figure out things for myself and if I wanted something, I had to go get it. I mean, I remember when they allowed kids to actually have a paper route. I would have a morning route [00:04:00] before school, and I knew all my friends were sleeping and I'd be up.

At the crack of dawn, you know, throwing the Philadelphia Inquire, you know, at people's doors, um, barely made any money doing that. But, you know, I think even in those early days, you [00:04:15] know, things like that taught me, you know, how to be responsible, you know, as simple as it might've seen to, to, to wrap some newspapers.

Most people were not doing it. And, um, I know that if I wanted something and. [00:04:30] I wasn't gonna get it from my parents. Not, not because they didn't want to, because they couldn't, uh, it was literally that simple, you know, you fast forward. I, I went to college. I was a history education major. I was gonna be a social studies teacher, Jonathan.

I could picture, you [00:04:45] know, having the little patches on my shoulder, you know, I'm I, my elbows and being like, I'm gonna go to this classroom. I'm gonna change these kids' minds. Eh, it didn't work out that way. I mean, I, I did my student teaching. And I really liked it, but there was some deep reflection at that [00:05:00] young age, and I was like, could I see myself showing up to this room, this, this, you know, four corners in this little room for 30 years?

And I think the answer was no. And I sought out on my own to figure out what I [00:05:15] wanted to do. And I was working in a deli in an office building and I wrapped my resume in all of the sandwiches that I made that week. And I could still picture them, like pushing the mustard aside, being like, what is [00:05:30] this?

And I saw people picking the paper up and it was cut in half and they're like, I have no idea what to make of this. But the cool thing is I got four or five job interviews. And I got a job. Um, uh, I got a job working in a home healthcare organization, [00:05:45] and two weeks before that job was supposed to start, the woman came down and I was still had my apron on making her sandwiches.

And she said, Rob, we had budget cuts. I, I, I can't afford to hire you. Oh. Totally dejected. [00:06:00] I said no to all those other people because I accepted a job, so there was no option. I was back in the deli again and the woman came back to me two weeks later and says, my husband owns a payroll company. Do you wanna interview Jonathan?

[00:06:15] I don't even know what a payroll company was. I got paid cash outta the guy's register. And I'm like, I don't care. I need a job. And that's how I got started in my career. 

Jonathan Blau: Yeah, it's pretty, it's a pretty amazing story by the way. I just wanna, you know, you, you and I were talking earlier today about, [00:06:30] uh, you having connection to Bayside Queens, which as you know, is where I grew up.

Yeah. But the funny part of your newspaper story is, is similar. I was, uh, the same way my, my dad when I was 13, passed away when I was 11. He was paralyzed. And [00:06:45] so, and my mom was kind of just absentee, so I like you. It was sink or swim. So you said it interesting you said, you know, I, I had, I had to, if I wanted it, I had to do it, but, but you didn't, you, you, you were lucky.

We either did it or we sank you. We both were able to [00:07:00] figure out a way to swim. 'cause we were forced to make that choice. And luckily we made the right choice. But I delivered newspapers. It was Newsday instead of what you delivered in Philadelphia. Oh, that means you 

Rob Basso: slept in, in the morning. 'cause that was in the afternoon I think, wasn't it?

Was that afternoon or? I, 

Jonathan Blau: you know, [00:07:15] I'm not, I'm not, I'm not evading the question. I just don't remember. But, but I, what I do remember is I had my cousins that was donated to me, his Schwinn. Five speed blue bike with, with tassels coming [00:07:30] outta the, uh, out of the handle of bars and the banana seat. I used to take that bike.

I put a, I put a, um, a basket on the front, and I loaded it up with my papers, and then sometimes it wasn't enough room. So I would, I would like figure out a way to split the, [00:07:45] the route into two, so I go back to get the other half of the papers. And then, and then luckily I was in better shape those days so I could go back and forth all day long.

It didn't bother me. Well, I did 

Rob Basso: the same thing. I, I had the basket on the front and one of those sling bags. Filled with newspapers, [00:08:00] right? That that's right. I mean, they, I think that's the only thing that Philadelphia Inquirer gave you was, here you are a paperboy, you get a paper bag. By the way, this wasn't like the fifties, you know, I grew up in the eighties, so it's like, this wasn't that long ago.

And people think, oh, you [00:08:15] delivered, they're thinking of the old news boys standing on the, the corner with the little cap. That's not quite right. 

Jonathan Blau: No. That, that's, no, we, we were, we weren't that generation. So, so one of the things I wanna talk about to, to. Jump off of, uh, how, how you got into the [00:08:30] payroll business.

I just want to take one step back and talk about your book, the Everyday Entrepreneur, and the, the, uh, what you call, call applying the triple thread a am ambition, confidence, and conviction, and you and [00:08:45] I succeeded. Long before you, obviously, before you wrote that book, right? So we didn't know about the triple threat yet.

We succeeded. So I'd like you to take us through why you think you succeeded without having the knowledge you're able to impart today as [00:09:00] a business coach and someone who, who, who wrote, who wrote the book on this. And, and, um, what kind of lesson that that could teach people beyond what you write in the book?

Giving people a foundation now that you and I didn't have, 

Rob Basso: so obviously the book was [00:09:15] written after years of reflection, of figuring out, you know, how did I do this? You know, and, and, and, and why did I do it? And, and, and what motivated me to do it. And when I, when I really look back at, I, at the times that, you know, I spent, you [00:09:30] know, struggling while I was building the businesses and, and, and moving along.

I just used the word motivation and like most people, I didn't always have motivation. You know, motivation, you know, gives people that, you know, false sense of [00:09:45] security. What I really had was determination. I had determination and I had sticktuitiveness, and I think that most people that try things. Try things for a certain period of time, and nowadays it's like, if it's not done in [00:10:00] six months, oh my gosh, you know, uh, I give up, I move on to the next thing.

Well. I didn't prescribe to that. You know, I took, you know, a lot of years getting good at my craft and my craft might not have been payroll service. My craft might have been, [00:10:15] you know, connecting with other individuals and, and, and gaining their trust and having them buy products and services from me, regardless of what those products or services was.

But the whole concept of that triple threat, you know, um, really came about because [00:10:30] those are the three adjectives that really. Any successful entrepreneur needs when growing a business, because you're gonna come across significant failures. You're gonna have these really low lows, you're gonna have these really high highs.

And [00:10:45] how do you come off those highs? You know when, when, when you have a drop to the bottom in a month or two, or even a year? Not every year I was in business, was the most spectacular year ever. I've had problems with partners, with vendors, with clients. [00:11:00] And you have to be able to get up every morning and say, why am I doing this?

What's the purpose behind this? And what's it all for? And for me at the time, you know, it was not just for my family, but it was [00:11:15] for, you know, financial success and hopefully to have freedom, um, from having to do anything that I, that, that I wanted to do. And I figured out how to do that. Nowadays with some of the.com folks would, you know, that seems like they're instant [00:11:30] millionaires and they're 22 years old.

Let's be realistic. Those are very, very, very few. The rest of us had to figure out over multiple decades how to build something successful. And when it was time to exit Jonathan, [00:11:45] I was nervous. You know, I was nervous, you know, making a boatload of money and not going and having something to get up to in the morning was daunting as, and my friends are like, what are you talking about?

You go play golf. You, you take up pickleball, you figure something [00:12:00] out. And that really wasn't me. So I struggled a bit after I monetized my businesses. 

Jonathan Blau: But by the way, let's, let's, let's, let's. Let's run with that a little bit because that's relevant to a lot of the audience members I think, that are listening.

Um, [00:12:15] one of the things that I've learned, uh, as a behavioral specialist is no matter how much money, uh, anybody, uh, receives from a monetization event, they're all based. With the same, uh, emotional, um, [00:12:30] roadblock. And that is for the first time in their life, they might have all this money, but it's also the first time in their life that they're relying on an intangible to, to provide them with their, with their sustenance, with their, with their standard of living money.

And that's very scary. [00:12:45] So if someone can have 50 million, 20 million, a hundred million, and they're still nervous because of what I just described. So if you can relate how, how that may have impacted, uh, what you were feeling when you, when you got your [00:13:00] money and you said, Hey, uh, I, I, I have it, but what?

But, but how did, did you, did you sense that same, that same roadblock? 

Rob Basso: Well, I had two exits in, in, in two and a half years. My big company was in 20 and barely two years later, I [00:13:15] built another one and sold that. To its separate public company. So I had some history with the bigger one, but at the in-between time there was almost like it didn't happen for 18 months or so because I was still busy building another [00:13:30] business.

I went right outta one right into another, which was probably a mistake mentally, but it gave me something to focus on. But you know, if you look at the two events, because they were closely. Aligned really close enough together to say it was a similar or the same [00:13:45] event afterwards, there wasn't this big sigh of relief like, oh my gosh, now I can do X or now I can do this.

Um, it was more. I dare I say it was, it was a depression almost. And, and people that [00:14:00] haven't experienced it might not get it and they might think, oh my gosh, you got, you have all this cash and you know, and you don't have to get up in the morning. You can do this sometimes when you have choices, it, it creates anxiety, you know?

[00:14:15] And that anxiety of having all these choices, literally the world is your oyster type of choices. It. You know it. It doesn't make it any easier. And I know some of your listeners like, ah, that's ridiculous. I would retire. I would do this. Let me tell you when [00:14:30] and if it happens to you, and I hope it does, you'll probably feel the same exact way I did.

Where you're a little lost. 

Jonathan Blau: Yeah, they will. By the way, it's the same kind of thing that you see. We default. Because of all the choices to [00:14:45] no choice sometimes. So for example, the the, um, when people go into their 401k plans as a new employer and they have. All these choices. Too many choices, you know, 50 things.

Mm-hmm. Uh, what they do is they [00:15:00] end up putting it all into money market because they just, you know, and that's what happens in life when we're faced with all these choices. I'm just, you know, I'm just gonna sleep all day. 'cause I don't wanna, I don't wanna do any of these. I don't want to, I don't want to pick.

Now one of the things that, um, that, [00:15:15] that I always take pride in is when I have someone like you who decided to reach out, uh, post. Monetization and, and you need to figure out who's gonna help you so that you can feel secure with, with your, with your investments and your, your what, what you need to [00:15:30] do to, to, to, to sustain.

Uh, what I always say, to make sure you don't run out of dollars before you run out of heartbeats. That's the main goal of everything we try out. But, but the, the fact that, um, you know, you and I got, got to know each other a little bit and [00:15:45] I feel like one of the things I try to do for all the people we help.

Is not to sell them on the idea that we're gonna find these great investments, uh, Rob, and you know, you're gonna make more than the s and p uh, every year and you're gonna be great. 'cause that has nothing to do with anything. Um, [00:16:00] and, and what it all has to do with in helping people is making sure that they can, one, stay with the plan that's gonna, uh, giving them the highest probability of not running out of dollars before heartbeats.

But my second, and [00:16:15] I think equally important goal, at least in my practice, is, is doing that for them with as few sleepless nights as possible. And the only way to do that, and, and I, you know, I'd I you to comment on it, 'cause now you've been working with us for a few years, um, is, [00:16:30] is have we succeeded at least with you, uh, in, in that second goal?

Because that's important to me. Getting you there to me is easy, but getting you there comfortably is what I think we try to do that, uh. That, that helps our clients in a way that they're not getting [00:16:45] at the Merrill Lynches and the, and the, and the Goldman Sachses of the world. 

Rob Basso: Well, Jonathan, it's a good question, and what I found is having this long-term financial plan was really no different than the plans that I made with my businesses.

We had [00:17:00] marketing plans, we had operation plans, we had growth plans, we had concepts that we wanted to fulfill. And that took steady, consistent effort, you know, for forward motion. And that's what you've really instilled in me that, that it's that it's not [00:17:15] entirely different. Meaning why was I struggling and why do a lot of people struggle with it?

You know, when it's kind of what they've done before, but because it's all new and it seems like you are creating and getting this [00:17:30] income from not doing anything. Literally not doing anything. And while that sounds like a dream, it's weird because to live the life you lived prior, you had to do stuff. You had to otherwise, that, that [00:17:45] financial existence did, did not actually occur.

So to receive renumeration without seeming effort. You have to constantly remind yourself, you worked the last 25 years to get to this point, so there was [00:18:00] solace and understanding that you, you've done this with other clients, you had a plan for me, which was not dissimilar to the plan that I had for myself running my businesses, but I just didn't see the connection right now, after a number of years and.

Plenty of [00:18:15] phone calls from you at the beginning, meaning when the market dipped 25%, I would be like, oh my God, you just see the percentage of your net worth just like disappear, and you're like, Rob. It's a momentary disappearance. And here's our plan. And [00:18:30] you would basically reiterate the things you told me when I first started working with you and your firm.

And by the way, it's not just you, Jonathan, it's your firm. Your firm has the same philosophy, and the people that I communicate with your firm have the same philosophy. Thank you. So for me, [00:18:45] it was that, that mental understanding of what I was going through and how to get through those dips and. Basically, and I think you've noticed even in the last year, I call you less.

Now that doesn't mean I don't love you. It means [00:19:00] I've gotten used to the, oh my gosh. And then all, especially now, everybody thinks they live in a unique time in history and with your newsletters and some of my own reading. Eh, nothing's that unique. You know, there's a [00:19:15] war, there's this, there's famine and effort, whatever it is, there's gonna be these dips, there's gonna be these cycle, but any x amount of period of time.

And as long as I keep holding onto that, I have a lot less stress in my day. I go about my day and do the things that I do [00:19:30] with very little worry that I'm ever gonna run outta money 

Jonathan Blau: and Right. But that's, see that, that's, that's, that's what I. Hope to achieve. Right. And with you, I guess it's been, it goes fast.

I guess. We've been working together almost five years now. Um, but, but that's [00:19:45] what I try to do with everyone is spend a lot of time in the beginning using, um, you know, the, the, the actual examples of what we're going through crisis wise. And saying, this is temporary, this will pass. And you have to stay focused on the plan.

And you do that [00:20:00] enough in the beginning years. And then, like you say, then you can go about your life for the next 20 years. And God forbid something happens to me, hopefully you've been, uh, trained temperamentally that you'll always be able to to do that. And that's really again, but that point 

Rob Basso: right there, if God forbid something happens [00:20:15] to you, which it won't, um, anytime soon anyway, um, you know.

It's just like, you know, getting a second in command in your business, you, you hope that you've imparted to them, mentor taught, mentored them and taught them where if something did happen to me as a leader of [00:20:30] a business or I wanted to work less, that the business would run just as well. And to be quite frank, that's exactly what happened my last five years in business.

Maybe I work. 10, 12, 15 hours a week in the business. I went off on other investments and had free time and did what I [00:20:45] wanted to do because I built the machine and the brain trust within my own organization. While I don't work for you, it's the same concept. You taught me the skills that I needed to have mentally to get myself through situations and not call you four [00:21:00] times a week.

Jonathan Blau: No, you're right. And there is continuity there for sure. So, Rob, um, when you, uh, like I, I, I went to watch you, I guess now it's almost two, two plus years ago, talk, uh, to a group of students at, at Hofstra. Um, [00:21:15] talk to me about some of the work. It was Stonybrook, it was Stony Brook. Uh, Stony Brook, right? It was Stony Brook.

I, I, I was lost. I ended up at Stony Brook. I went to Hofstra initially, but, uh, but what ha te tell me about the work that you do, um, in that space with, with some of the, [00:21:30] um, younger generation. 

Rob Basso: Yeah. Well, I, I think what a lot of universities do really well is they, they, they, they teach the basics. They, they, you know, they teach 'em, especially the business students, they teach them the basics that they need to know.

And they're getting [00:21:45] much better lately in the last handful of years at giving them real world experience of what it's like to really. Start a business to grow a business to exit from that business. And what my talks usually encompass are [00:22:00] is my story arc, the ups and downs in the trials and tribulations that happen to an entrepreneur along the way.

And what I found was it resonates really well with these young people. And I pay attention when I'm giving a talk, you know? I see who's [00:22:15] focused, I see who's on their phone. And you know, the goal as a professional speaker also is to make sure that you have an engaging enough topic and an interesting way to deliver it.

That people are engaged in paying attention. But the, for me, it's exciting [00:22:30] because of the people that wanna talk to me afterwards, and usually I can tell how well interested they are in a topic or discussion by how long the line is to have a conversation with me. And if you've got 60 or 70 kids waiting to talk to you, I.

About [00:22:45] what you just said. Number one, the university probably did a right job of teaching these kids the basics and figuring out, okay, we're bringing these speakers to you for a reason. You should soak up all the information and knowledge. And believe me, I never had all [00:23:00] the answers for these young professionals up and coming.

I had my viewpoints and, and the way that, that it worked for me, it doesn't mean that's the way it'll work for them. Things are changing and constantly changing, and I mean [00:23:15] that in the workplace with the advent of ai, just all of the things that were different than when we came up. I mean, Jonathan, I mean, I remember when we went to college, there was no P, there was no computers, there was no internet.

Terrific. A Commodore or a [00:23:30] word processor, but the internet didn't come about till the end of my college career. I didn't even have a cell phone. Till a year and a half after I graduated. The young professionals now have a ton more to navigate and I'll contest, it's probably a little harder for them now than it was [00:23:45] for us because it's not just about their own steam and ambitions.

It's about being able to juggle the significantly changing environment that we have right now. 

Jonathan Blau: A hundred percent. And you know, it's funny, I remember in college, Rob, I had, uh, I had word star, which was a little s [00:24:00] floppy disc that I put into the computer. And I was, I was, at the time, I was an intern at Lehman Brothers in 1988, and Smith Corona was doing a secondary offering.

They were issuing more stock to raise some money for those who were listening, dunno what a secondary offering might be. [00:24:15] And I was in the morning meeting as an intern, I was allowed to go to these morning meetings. So they were, they, they, they, they were presenting this, this, this, uh. The word processor a as this, you know, the, the improved version of it.

And this is gonna be great, and we're raising money when invest and I, you know, [00:24:30] no one ask questions if 30 or 40, uh, what they call stockbrokers those days in the room. And I, this little peon intern, I had a question. It was a real question. I wasn't trying to be a wise guy. I said, I'm in college right now.

I couldn't afford one of these. I think it was $350 at the time. One of your [00:24:45] word process, and I'm sure there's a lot of students, most of 'em probably similarly situated, where they can't just plop 350 on a word, but I can take a floppy dis called word perfect and put it into the computer that I, that I'm, uh, presenting within the library without any charge.

Yep. [00:25:00] Why am I not gonna do that? What, how, how are you gonna overcome that? They didn't really have a good answer, and ultimately they went outta business. So I think I was onto something. But the other thing is when you talk about, um, what the kids have today, we had cobol, if you remember, that was like a, a, that was [00:25:15] the business.

Um, I. Um, it still exists, 

Rob Basso: believe 

Jonathan Blau: it or not. 

Rob Basso: There are still legacy seen 

Jonathan Blau: companies that run on cobalt. Yep. It's so funny. So I learned that stuff, but you know, I guess the main point of bringing that up is you and I live through all of that as these [00:25:30] kids will live through what they're gonna live through technological change and advancement.

Except I think for them it's gonna be much more rapid, right. Uh, than, than it was for us. But you have to be able to operate. Successfully in the face of all of these changes. And I think it [00:25:45] comes down to what you say, you have to be ambitious. You have to persevere and, and you have to have all of those tools always working.

Mm-hmm. And the other stuff just comes and goes. Right. But if you don't have the, if you have the basics, I think it'll always succeed. But if [00:26:00] you don't have the basics and you have only the technology and the advancement, you won't succeed. It's just always been that way. I think it's always gonna be that way.

I'd like to finish off by. Um, asking you to, if, if, if you can, uh, come up with something, uh, that, that comes to mind [00:26:15] for these two things. One is what, what might be from memory, one of the most challenging, uh, experiences you had in business where you thought maybe it could even become an existential threat to your business and how you overcame it and what lessons you learned from [00:26:30] it about dealing with.

Threats like that. And, and then on the flip side, one, one of the biggest turning points positive in business and what that taught you. 

Rob Basso: Well, one of the biggest existential threats, uh, was, was actually it wasn't [00:26:45] existential. It was, it was real. Um, it was a disagreement with my business partner and, and to give some background on that, um, I didn't have a, a ton of money to start a business when I was 22 and a half years old.

Um, when I left the prior payroll company, I was [00:27:00] working because I was underpaid and underappreciated. Um, and I literally went back to one of the people I had sold payroll services and we just, we, we we're friendly and hit it off, and I didn't know a ton of business people knocked on his [00:27:15] door. He let me in.

I showed him a simple Excel spreadsheet and said, uh, would you like to be my business partner? And practically, instantly he said yes. And within a week we were signing our partnership agreement on the back of his BMW in Bayside Queens. [00:27:30] And we had a good run for a lot of years. Until we didn't. And what happened was, uh, I was the workhorse and we all knew the deal at the beginning.

He was gonna put in some money and some mentorship, and it was a [00:27:45] loan. Didn't give me the money. It wasn't really an investment. We each invested $10,000 into the business, um, as starting capital. And the rest he loaned us, which was only $70,000. Now it doesn't sound like a lot. I didn't have it and I really couldn't [00:28:00] function without the funds to be able to start the business.

So on my steam and his mentorship in the first few years, we, we did very, very well. Um, but then eventually, which happens a lot when there's money at stake, he took advantage. I. Um, he [00:28:15] took advantage that, 

Jonathan Blau: no pun intended. 

Rob Basso: Yeah, yeah, though, 'cause the name of my company was Advantage Payroll. That is, uh, good works out.

He took advantage and treated me like the goose that laid the golden egg. And when we were contemplating other partnerships and other things we wanted to do, [00:28:30] um, we were gonna create this other entity. And I said, okay, you know, this was many years into the relationship. I said, okay, we'll each put up equal amount.

And I said, well, what are you gonna do for the company? And he goes, nothing. You are gonna do all the work. Just like that. And [00:28:45] my attorney and even his attorney said, what the blank are you talking about? You know? And he's like, no, I'm not gonna do any work. He goes, in fact, um, you know, you should put up more of the money and I should put up little, but still get [00:29:00] 50%.

And I was like, what? What, what? That was the last, that was the beginning of the last day of our partnership. Because when, when, when, when you get to a certain point. You know, in your career, you know, [00:29:15] you, you, you, you don't need the help that you needed before. And it's not that I was ungrateful, it's just after a non-working partner making over a million dollars a year, never working in the business, and then trying to tell me that at a different stage [00:29:30] in my life that it's gonna be the same deal I made when I was 22 that I should make when I'm 40, right?

Is kind of the definition of insanity. Yeah, so the hardest thing that ever happened was separating from that partner because we had a real relationship. It wasn't [00:29:45] quite father and son, but there was a lot of mutual respect. So, breaking up, it's like a divorce. Uh, I imagine I've never been through a divorce and I, I hope I never do.

Um, me too. The simple fact, because I, because I 

Jonathan Blau: like Mary Beth. Vaso hope that Glad so do I. [00:30:00] 

Rob Basso: It was, it was so mentally taxing because you have all the emotions and finances, you know, connected with this other individual that it was the single hardest thing. Um, and also to realize that that person that you [00:30:15] thought of one way.

Really thought of you as someone who was just a moneymaker for them. And that was really hard. That was very hard to handle. And we didn't talk for many years. And recently we started kind of chatting again, um, but mostly 'cause he's much older [00:30:30] now and I. I'd like to think of myself as a decent human being.

And you know, he, he's not gonna live forever, so I don't wanna say bygones or bygones, but you know, we've, we've, we've had some relationships again. 

Jonathan Blau: And you survived the split, obviously. You survived the split and, yeah. Survived [00:30:45] it and, 

Rob Basso: and did very well with it. Yeah. In fact, in fact, it unencumbered me to do the things that I always wanted to do and how I wanted to do them in the business.

100% on my own. And that's how, by the way, I built another business very successfully in two [00:31:00] years and exited to another public company because I was unencumbered by, uh, a partner that didn't really understand the modern world and what I was trying to do. So that's really the most difficult thing. And what was part two, Jonathan?

Now that I [00:31:15] got off here, oh, part two 

Jonathan Blau: is what, what was one of the key, uh, successful moments that might have even been pivotal? Uh, in, in, in your career? 

Rob Basso: Well, uh, uh, this is an interesting one and it goes back to the beginning, uh, of my career. So when I was [00:31:30] investigating opportunities and what I wanted to do after I left the payroll company that I quit after about a year, I.

Uh, I didn't know that I wanted to stay in the payroll industry, so I investigated lots of options and one of them was licensing a piece of software because building your own software [00:31:45] in this industry is, is very costly, very difficult, and I didn't have the resources to do that and probably nobody would've trusted me at the time to do it.

Um, so I investigated all these different softwares and I met a gentleman named David McAllister and. For [00:32:00] whatever reason, he took a significant shine to me and thought I would be a perfect person to license his software. And I said, you know what? You don't really wanna license the software 'cause it's really a job.

I didn't wanna just work for your company. [00:32:15] He helped me. Convince the CEO of this company to not just work for them, but make a deal. That said, if I did X in a certain period of time, he'd let me buy the whole thing back from him. [00:32:30] Now. I, I, I couldn't believe we were even negotiating such a deal, but I knew that the minute that that leader of that company made that deal that I was gonna get that company back and I was gonna end up buying it.

And the more all of this, and by the way, I [00:32:45] did, and we totally crushed whatever goals he wanted to put. And that's how I got really got started on my own journey and less than 18 months. But the moral of this story is. Someone took a chance on me on those early stages where he didn't really have [00:33:00] a significant vested interest other than helping another person.

Yeah, he made a sale and he made me look good, but he did it because he believed that I could do it, and we just connected. He was probably about, well still is. He's 15 years older [00:33:15] than me and we're still friends today. Without that person, I'm not sure that my story would've gone the way. I think it would've gone well, but it wouldn't have gone well in that industry the way that it went without one person taking a chance on me.

Yeah. 

Jonathan Blau: So, [00:33:30] and that's not unusual, right? That's why I asked the question. Like, you, you look at, um, bill Gates happened to go to the one, uh, high school in the country that had a computer in those days. Right. If he didn't, we wouldn't have Microsoft. I mean, it's just one of those things, right? So, so. There's always that one thing that can change [00:33:45] our whole trajectory in a meaningful way, even if we would've still succeeded, for example.

I wanna, I want to end with two things. One is I want to just, uh, this is a compliment to you because, because, you know, I want, I want to pay it to you. Um, I've really gotten, uh, a lot of pleasure out of [00:34:00] getting to know you, uh, for a lot of reasons, but one of the podcasts I did are the particular challenges that executives and entrepreneurs have as investors.

And one of the challenges, they're overconfident because of the success they achieved as entrepreneurs. They think they can relate that same [00:34:15] skillset that led them to entrepreneurial success, to invest successfully, to perform knee surgery on themselves successfully, whatever it is, they could do everything better if their hand is in it, right.

So that overconfidence bias in investing kills them because it's like a big [00:34:30] magnifying glass over all the human nature biases that destroy the rest of us, except they, they magnify it with the overconfidence and blow up faster and worse with a lot more money. That didn't happen to you because you're humble.

Um, you know, you didn't look at your, your [00:34:45] portfolio as, Hey, I, this thing isn't doing well, let's get rid of it. This international, and let me put it into the, the, the, the, uh, technology piece. Uh, because this, the, the, the, the international is a bad division of my business. And this is good. You were able to, to, to not [00:35:00] go down that path, which is, so you're, you're among, uh, uh, the minority of entrepreneurs that succeeded that I can actually help to be candid because of your humility.

And, and because of the fact that you, you didn't develop that overconfidence, and I think it comes. [00:35:15] In large part because of how you grew up, but it also shows in that you give back to the, to the community, to the, to the younger generation. Mm-hmm. You wrote your book, I didn't think you wrote your book to get richer.

You wrote your book to share, uh, with people what [00:35:30] your knowledge was to help 'em. So let me segue that into talking just close off by talking about. Your business now of helping people as a coach and how that works and how people can, uh, find out more about it, and then anything you'd [00:35:45] like to say in addition to that about the book or anything else.

Okay, great. Relating to how you help people. 

Rob Basso: Well, I've got three areas of my consulting practice now, and one of them is direct, CEO, president, founder. Owner coaching. [00:36:00] And what I, what I discovered is that while I believed I was a good leader and, and, and led a good company, um, there wasn't a lot of formalization of how to get somebody from point A to B2C to their specific goal.[00:36:15] 

It happened, but it didn't happen in a codified way. So what do you do when you have a lack of knowledge? If, if, if you really want to be good at something, you go back and you get educated. So I took six months worth of coursework to learn how. To codify the things that I [00:36:30] kind of already knew how to do, to walk people through a process, a tried and true and proven process to get what they want outta their life and their business.

So that's one piece of it. Another is a direct consulting piece where businesses hire me, [00:36:45] um, to help them, either through challenging times to help them grow or to help them get on, uh, a path. So they're ready to exit their business when that time comes because too many people aren't prepared to sell. I was only [00:37:00] modestly prepared mentally to sell.

Um, and I know that I can bring a lot to the table because of the process that it takes, and also to help people really give them the chance to have the highest, multiple exit possible through some key [00:37:15] things that most entrepreneurs are unaware of until it's too late. Then they get undervalued. And the last piece to me, um, is, is, is also really exciting.

So less than six months ago, you know, I kind of had this epiphany, but [00:37:30] realized, you know, what am I really good at? What, what, what have I done well in my career that can easily be adopted by others to help them be successful? And I think it was the branding of myself, the personal branding that I put [00:37:45] towards letting the world know.

Um, my professional skills, the way that I communicate the importance of certain things in business. So I started a social media company specifically designed for leaders and CEOs and top officials and [00:38:00] organizations of any size that are wildly underserved by LinkedIn, meaning they've never used LinkedIn or they use it, but they post once in a while.

It is such a powerful tool. If you are not using [00:38:15] LinkedIn to build your personal brand, you're being left behind and some people believe CEO LED marketing is silly. The company is supposed to be more important than the CEO. While I believe that's true in the long term, if [00:38:30] you're a smaller, medium sized business owner and you are a leader, you are wildly important to the success of the company.

And why not use your most? Incredible asset. You and your ability to show people why they would wanna work for [00:38:45] your company, why they would wanna hire your company, why you're better than the competition without actually selling. You. Position yourself as an expert in your industry and people will want to know you.

And that's what we do. We help them come alive [00:39:00] through the power of LinkedIn. 

Jonathan Blau: Well, I, I, I say I highly endorse Rob talking to the audience. He, he's. He's a genuine person. There's nothing to me in life that's more valuable than authenticity. He has it, and I feel I have it. It's one of the reasons we connect, [00:39:15] and I think if you need help in any of those areas, you, you, you, you have a wonderful resource and Rob, so reach out to him.

And, uh, and Rob mentioned earlier that, uh, what am I gonna do when I retire? When he was. Selling. Am I gonna play golf? He didn't play golf. He became a pilot and he [00:39:30] flies a plane. So I get a little nervous about that every now and again. Oh, but the good news is his plane has a parachute, so that makes me feel a little more comfortable.

Pretty sure you 

Rob Basso: advised me not to do it. Sorry. That's one thing I didn't listen, uh, on that note, it's, it's the most difficult thing I've ever [00:39:45] done besides running my businesses. But I will tell you, it, it took all my brain power. I needed it. It's been a big help to me to keep my brain really sharp. So, 

Jonathan Blau: and I, and again, I take comfort in the fact that you have a plane with a parachute.

[00:40:00] So that, that's, that's the, that keeps, that keeps me from losing too much sleep at night. When you tell me that you're flying from, uh. From Boca to wherever you you're going back home to these days. Alright, well Rob, thanks again for, for, uh, joining us today. It was [00:40:15] really great to have this conversation and thank, uh, thank you to the audience for tuning in.

You can get us on Crazy wealthy podcast.com. Uh, all of the venues that you get your podcasts on typically, uh, are, are also, uh, gonna be [00:40:30] able to be where you can avail, uh, crazy wealthy. So, till next time, Jonathan Blouse signing off. Stay tuned to hear Amy's calling for the recap of today's episode. 

Amy Blau: Hi honey.

Jonathan Blau: Hello, honey. How are you? 

Amy Blau: Well, we'll be fair to the [00:40:45] audience today and let them know that I'm really looking out my window and I see you swimming in the pool. It's July 4th weekend. I know this will probably hit the air a little later than that, but we're in vacation mode. [00:41:00] 

Jonathan Blau: That's okay. But you're not really being honest because you are looking at the pool, but you're also looking at the ocean.

Amy Blau: Oh, that's true. That's true. And I'm looking at such a handsome guy sitting in the pool. 

Jonathan Blau: Yeah. Well, I don't even know who 

Amy Blau: that is, Peter. That's That's the pool guy. That's the [00:41:15] pool guy. So I heard you had a phone call this morning. 

Jonathan Blau: I had a phone call Yes. With my, my, um, friend Rob Baso. 

Amy Blau: Rob, we, I, I, I give a lot of credit to Rob.

He's [00:41:30] really impressive guy to me. My fun, my favorite story about Rob's, I'm sure he talks about it, was the deli sandwiches. 

Jonathan Blau: Oh yeah. That's a great, great story. Rob is, um. Rob has just got a lot of, uh, [00:41:45] perseverance, self-taught, kind of like me, not that it's anything ever about me when I Right. It's never about you, Doug.

And, and, um, and he's also very humble like me. He's, 

Amy Blau: oh, I, in terms of [00:42:00] humble, there's no one more humble than you. So I can't imagine him being more humble. 

Jonathan Blau: I grew up, it was Jonathan r Bl, and I changed it years ago to Jonathan h bl, 

Amy Blau: John Jonathan, humble bl. The, the funniest thing about that deli sandwich [00:42:15] story is if we told it to any one of our children, or mo, I shouldn't say any, anyone, but most children of this generation.

If you told them that story, they would look at you like you had nine heads. 

Jonathan Blau: Well, there's most, most stories that you [00:42:30] would tell our kids about anything having to do with, uh, creativeness and in and ingenuity as it relates to seeking job opportunities. They look at you like you have five. In fact, just telling them that you sought job opportunities might have a look at you like you have five heads.

It's true, [00:42:45] 

Amy Blau: not all, not this whole generation, but a lot. 

Jonathan Blau: Yeah, I agree. 

Amy Blau: Anyway, so what were the, what were your takeaways from your conversation with Rob? 

Jonathan Blau: You know, he, he's just, um, my, my takeaways is he is, he is what I thought he [00:43:00] always was, you know, just hearing him talk about his stories. I. Really fleshed out what I always thought he was, which is, and I'm not kidding, someone with a lot of humility, a lot of success still, still works as a coach.

You know? Not, not 'cause he has to, but he likes to help [00:43:15] other people. So he's an entrepreneur coach, um, helping businesses and business owners learn to, uh. You know, be better at what they do and feel good about what they do. He's, he does these motivational, um, clips on social media [00:43:30] and, um, and he is an all around, just good guy.

He's married to Mary Beth Baso, who I've gotten to know. And you, you met, I know, last year in Florida, uh, who's really, really nice and really nice. Good, good family man. It's all, all around good guy. And, um. [00:43:45] He continues to, to go through life, like enjoying life, but still challenging himself, which is, well, he 

Amy Blau: sometimes he enjoys life a little too much 'cause he scares me with that airplane.

Jonathan Blau: Yeah. But the one good thing about his, um, his [00:44:00] piloting is that he has an airplane with a parachute. Oh, right. That right. 

Amy Blau: That makes me feel very, very safe. I 

Jonathan Blau: mean, it makes me feel safe for him. I still wouldn't fly it. 

Amy Blau: Right. No. And one, you know, I'm in fairness to the audience, I do know Rob pretty [00:44:15] well, so I'm not speaking without having, you know, having had conversations with him before.

I do know that he's also very inter mentoring the next generation and yeah, he's mentor the next 

Jonathan Blau: generation. Yep. He, he really does. He loves to give [00:44:30] back. Um, we, we talked about his, uh. His presentation a number of years ago at Stony Brook, which I went to, you know, uh, just to watch him speak. And there really was a lineup of, uh, of, of, uh, people in the audience because students to ask him follow up [00:44:45] questions and, and his stories are just very relatable and, um, and it makes you feel like, if I could do it, you could do it.

That's how Rob. Presents himself. Um, and I, I love the fact that he has a connection to Bayside Queens. Uh, he also was a paper boy, like I [00:45:00] was, he delivered the Philadelphia Enquirer, I think, and I, I delivered Newsday. So anyway, it was a fun, and I think, um, enjoyable for the audience who's gonna listen to a podcast and, uh, it's, it, I'm looking forward to having it there in another week or two.

So 

Amy Blau: what would, what, what is [00:45:15] his biggest piece of advice? Because he's been successful and obviously you've been very successful. Having talked to him, what's your, what was his biggest piece of advice? You, to someone? I dunno about his 

Jonathan Blau: biggest, I dunno if I call his biggest piece, but what, what he said that made sense to me that just [00:45:30] is simple but resonates is everyone expects, you know, if they're gonna try something, if it doesn't work in the first month, they're gonna try something else.

He said how it. You know, he spent years, um, perfecting in his mind his craft to be able to succeed with it. In [00:45:45] business, not months, and you have ups and downs every year or every month isn't a good month. You have to accept that that's gonna be the case. Much like I teach my investors to accept that you're gonna have temporary decline, temporary declines, the [00:46:00] declines come.

Um, f frequently, sometimes deeply, but always temporarily. And you have to learn how to live with that and continue to, to, uh, operate effectively. Same thing with business. That's how Rob is. You know, you, you have disappointments. You're not gonna succeed in, in a month or two. It could [00:46:15] take years. Keep going.

And that, that to me is, is what I would say in answer your question. 

Amy Blau: You know, now that you say that, that's kind of like marriage also. It's been 30 years and I'm still waiting. Like I'm, I'm pers I'm gonna be perseverance and I'm gonna, I'm gonna. Tough it [00:46:30] through. I know the good times are coming. 

Jonathan Blau: No marriage to me.

It's like karate. I've just built a resistance, right? So it doesn't, nothing hurts me anymore. 

Amy Blau: And on that note, everyone, I hope you guys had a great fourth and that you're having a great rest of the summer, and we'll speak to you [00:46:45] again. 

Jonathan Blau: All right, until next time, Jen.

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