I Took a Hike

Rob Basso - The Exit Plan

March 12, 2024 Darren Mass/ Rob Basso Season 3 Episode 9
Rob Basso - The Exit Plan
I Took a Hike
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I Took a Hike
Rob Basso - The Exit Plan
Mar 12, 2024 Season 3 Episode 9
Darren Mass/ Rob Basso

When history major turned business titan Rob Basso wrapped his resume in a sandwich to score job interviews, little did he know it was just the appetizer for an extraordinary entrepreneurial feast. Journey with us as Rob recounts his flavorful tales of launching ventures, the emotional weight of selling them, and the fulfilling yet challenging dance of work-life balance. His candid anecdotes serve up a hearty meal for thought on how unconventional strategies and a dash of creativity can be the secret sauce to a successful life and career.

Embark on a rollercoaster ride through the high stakes of business deals with an entrepreneur who has navigated both the adrenaline rush of signing deals and the bittersweet moments that follow. Rob opens the vault to his experiences with selling companies and the introspective aftermath, sharing the personal impacts and the insights on strategic negotiations. Meanwhile, we take the scenic route around topics like private jet ownership, the perception of wealth, and grounding oneself in the face of luxury's lure.

Lastly, Rob's narrative isn't confined to boardrooms—it strides into the nuances of raising a family amidst affluence and the evolving dynamics of entrepreneurship across generations. We travel through the emotional landscapes of an entrepreneur's life post-exit, the pertinence of work-life harmony, and the empowering leap from corporate chains to the freedom of entrepreneurship. It's a dialogue that stretches beyond the horizon of business, offering panoramic views of the human experiences that shape our individual and collective journeys.

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Show Notes Transcript Chapter Markers

When history major turned business titan Rob Basso wrapped his resume in a sandwich to score job interviews, little did he know it was just the appetizer for an extraordinary entrepreneurial feast. Journey with us as Rob recounts his flavorful tales of launching ventures, the emotional weight of selling them, and the fulfilling yet challenging dance of work-life balance. His candid anecdotes serve up a hearty meal for thought on how unconventional strategies and a dash of creativity can be the secret sauce to a successful life and career.

Embark on a rollercoaster ride through the high stakes of business deals with an entrepreneur who has navigated both the adrenaline rush of signing deals and the bittersweet moments that follow. Rob opens the vault to his experiences with selling companies and the introspective aftermath, sharing the personal impacts and the insights on strategic negotiations. Meanwhile, we take the scenic route around topics like private jet ownership, the perception of wealth, and grounding oneself in the face of luxury's lure.

Lastly, Rob's narrative isn't confined to boardrooms—it strides into the nuances of raising a family amidst affluence and the evolving dynamics of entrepreneurship across generations. We travel through the emotional landscapes of an entrepreneur's life post-exit, the pertinence of work-life harmony, and the empowering leap from corporate chains to the freedom of entrepreneurship. It's a dialogue that stretches beyond the horizon of business, offering panoramic views of the human experiences that shape our individual and collective journeys.

Support the Show.

Contribute to the granola bar fund :)

Follow The Journey on Instagram
Tiktok?

Submit Feedback
Apply to be a guest
Become a Sponsor



Speaker 1:

Alright, rob Basso, are you okay with being recorded on a podcast? Absolutely, oh shit, there goes that liability. This is, I Took a Hike. I'm your host, darren Mass, founder of Business Therapy Group and Parktime Wilderness Philosopher. Here we step out of the boardrooms and home offices and into the great outdoors where the hustle of entrepreneurship meets the rustle of nature. In this episode, we take the energetic path alongside an entrepreneurial achiever with Rob Basso. Our topics include the hustle of a true go-getter, the creative CV strategies for that first real-world job, the emotional highs and lows after multiple successful exits, plane ownership and the value of a purposeful life. We are filled with energy, descending alongside a vibrant, successful leader, and I Took a Hike with Rob Basso.

Speaker 1:

This episode is sponsored by DeFi Supplements. Are you feeling stuck in a rut? Do you need more energy for the trail, stuck behind the screen all day and lacking focus? Well, you need to recalibrate my friends, and get your energy back for the summit. It is a premium brain health supplement, doctor, formulated to help with energy, focus, mood and longevity. Visit defiyourmindcom and use code Hike for 20% off and you will defi your expectations. Alright. So, rob Basso who are you?

Speaker 2:

That is a good question, and why do you start with the difficult ones?

Speaker 1:

Well, because if they were easy, then this wouldn't be fun.

Speaker 2:

Well, first off, I'm a dad. I've got two kids my son, nick 23, and my daughter, skyler's 20. They both live down in Tampa and they're loving life. My son's working on his professional career. My daughter took a little break from school and figuring her world out, and I'm just excited to know that they're doing well and trying to be happy, productive citizens of this world.

Speaker 1:

That's good. It's hard to be a dad, right.

Speaker 2:

It's harder than I thought it would be. To be quite honest with you, you always have the best intentions, you have kids and at the end of the day, you get some of it right, you get a lot of it wrong and most of the time they survive pretty well. As far as professionally, it's just a very interesting story, just like probably a lot of the entrepreneurs. I was a history education major. I went to Hofstra University and everybody's like you were a history major and you ended up running businesses and building them and selling them. I'm like, yeah, and they wonder, well, what was your training? How did you do that? And at the end of the day, I learned how to communicate. I learned how to get my point across, and this is synced, clear fashion and that's what I found is mostly what runs good businesses is that great communication with your clients and your staff.

Speaker 1:

That's right. And do you finish up all your stories by saying the rest is all history?

Speaker 2:

No, did I say that?

Speaker 1:

No, it would be true, you could have that one. All right. So you were a history major, and I think this is pretty true for most people out there. They don't end up working in the major that they studied. I think I might be the only person going to school for telecom and then going to telecom, but here I am interviewing you on a trail.

Speaker 2:

But that is the beauty of this world that we live in, and there is no set path. Listen, if you were choosing to be an accountant or an attorney or a doctor, a lot of times those folks continue down that path. But I could have just as many friends who became lawyers and never practiced a day in their life and just use the skills that they learned in law school and they used it in their next career.

Speaker 1:

All right, so you did not go into history. Where did you go? I did not.

Speaker 2:

I did not know what I wanted to do and I was working in a deli in an office building because I needed to pay rent. My dad was good enough to pay for my college, but when college was over, that was it. I basically got a couple months and I was completely cut off and I looked back and I was not even mad at that. I knew that that was the way it was supposed to be. So I was struggling, living with probably five friends in a really shitty house somewhere in Long Island in a bad neighborhood and working in this deli. And it was in an office building. So people kept coming down. I said you know, all these people go to work every day. What do they do? So I wrapped my resume in all of the sandwiches yeah, you did it.

Speaker 1:

I can still picture it.

Speaker 2:

Yes, I did, no you did it and I didn't know what I was doing. I said I could literally picture them pushing the mustard aside. No, you did it, I did.

Speaker 2:

Wait. You printed out your resume and wrapped it in the sandwiches along with the rest of their meal and I must have got four or five different job interviews. That could be the most ingenious. Maybe if your listeners hear this, they'll start doing it and they'll get jobs out of college. All right, I'm flabbergasted. That's ingenious.

Speaker 2:

Well, I didn't know it at the time. I was desperate to be quite frank with you and I said how am I going to meet these people? And you know, I had the dirty white apron on for making their lunches and I got a bunch of interviews there and I almost had a pick of which jobs I want in marketing or sales. So this one awesome woman she gave me this job and two weeks before I was supposed to start she came down and I saw the look on her face and I knew before she said a word we had budget cuts, I can't hire you. So even at that young age I think I knew it was very difficult to go back to the other few that I got offers. By the way, your choice number two, it's just so.

Speaker 2:

I didn't Okay, what was the role it was in the marketing department. It was like a junior associate, low level beginner rep in their marketing department.

Speaker 1:

So you were a history major working at a deli in an office building Wrapping your as the kids say CV. We've gone backwards it's now a CV In ham sandwiches. That's an interesting role.

Speaker 2:

Well, it gets more interesting, though, because I didn't remember I didn't take the job because she, she couldn't offer to me because I had budget cuts. So three weeks go by, I took another part time job, but she called me out of the blue and said my husband owns and operates a payroll and human resources company. Now, to be quite frank, I didn't even know what that was because I'd always been paid in cash Really didn't know from taxes at that particular moment Sorry if the IRS is listening at that point in my career, my life, it wasn't a thing.

Speaker 2:

And then I said, okay, I'll interview with them. And then I interviewed with them and that's how I got started in the industry that I spent 25 years in. And what industry was this? I was in the payroll business. So I owned a payroll company called Advantage Payroll Services for 20 years and we did payroll and HR. You've probably heard of companies like Paychecks and ADP. We were direct competitors of these huge multi-billion dollar giants in the New York region. And how?

Speaker 1:

many clients did you have Almost 4,000.

Speaker 2:

Wow.

Speaker 1:

How did you get your clients?

Speaker 2:

Mostly by doing. What we're doing now is having conversations and part of the challenge when you're a small guy going up against the big dogs especially when you're talking about online marketing or Google AdWords or things like that they were buying up all the really and making it almost unaffordable for the little guy to do any kind of pay-per-click back in the day. So we had to do it the old-fashioned way and go and make relationships. So what we did was we made relationships with CPAs, accountants and financial advisors and became indispensable to them by connecting other types of business to the things that we did and when they used us, we act as the hub of their entire business process and we became invaluable and we were very good at it, fortunately, and I hired really good people to do things that I sucked at.

Speaker 1:

So many important themes here, so one you essentially became a connector, a relationship builder between CPAs and I'm sure there were some back-and-forth referral relationships.

Speaker 2:

There was the best of what we could. But you know the funny thing about that is they always wanted it to be that way the CPAs and the attorneys Because I did so much business with other CPAs and attorneys it was very difficult for us to do that. So what we tried to do with, we tried to lead with the fact that we're just going to make you look good. Yes, our price is a little better, but I never sold on price, I sold on value. Yes, which I'm sure in your world was sometimes challenging, because Telcom is a very competitive industry and it was a lot price-driven, if I remember correctly.

Speaker 1:

Yes, you're right, but we would sell on value, because when everyone else is selling on price, there's always someone willing to be cheaper and cheaper. If you're not cheap enough, then eventually quality suffers. So I learned at an early age to always sell quality over quantity and always sell quality over pricing, because as a small company, if you're solely focused on being the cheapest, you're not going to have enough margin to grow. You won't grow your processes, you won't be able to hire the right people. We're the best people that you can afford, the best equipment, the best this or that, and therefore that will hurt you a lot.

Speaker 2:

We did little things, darren. Like, yeah, we had client numbers because we had so many clients, but generally when they called we went by their company name. They really knew who they were speaking with and at the end of the day there was some end decision maker they could get ahold of me. Now, when you get that many clients, I could not speak to every client, even if I wanted to, but the ones that were significant enough that there was a big enough issue, I never worried about getting on the phone, and I think that's a big challenge. Nowadays, people hide behind their email and their texts and think that that's sufficient.

Speaker 1:

Believe it or not, it's okay. Now it's about instant messaging.

Speaker 2:

The answer has been 37 seconds. It does make it more challenging for, I think, the younger generation, because people's expectations are different.

Speaker 1:

And look at this view Wow.

Speaker 2:

And we did that in like 25 minutes. Wow, this must be the highest point in New Jersey. New Jersey's flat is aboard. No, there's a high one. We're not done yet. Yeah, we're not done yet.

Speaker 1:

And there is a place called High Point. I believe it's 2800 feet elevation, which is the highest point. Wow, this is perfect. Northern New Jersey, and I have hiked it before. This episode is proudly brought to you by Brand Built, a dynamic social media networking community designed to elevate your success and stuck in a brand loop. Your brand matters more than ever before and falling behind is not an option. Join our dynamic community for expert social media guidance, valuable lessons, education, weekly spotlights, monthly speakers and a robust brand building network. Explore more at MyBrandBuiltcom and join me in the chat for a thriving journey to success. Tell me what it was like when you had your first signed contract in the payroll business. How did that feel like?

Speaker 2:

I remember it pretty clearly too. And here's the thing In my mind I knew that I was going to get 30 more that quarter and I just knew it. I just really felt that. And it might sound like crazy talk, but the truth is I signed that first one, and now it's different. So when I signed that first one, I was like when am I getting my next? It wasn't, oh my god. Amazing job, rob. You started this business. You've never met these people before. They signed this contract and they let you in their bank account Like who would do that?

Speaker 1:

There was no celebratory.

Speaker 2:

No, I was 22 years old and it's like no, what's next? How am I going to pay the bills? So now I have to say, after many years, I do celebrate the small wins and probably by the time I was in my mid to late 30s, I started celebrating a little more, because otherwise, if you're on that constant drive, you never feel satisfied with your life or what you have or where you've been. And it did take me a while, but I don't even want to say that I'm there yet, darren, but I'm getting there. Listen, when I started figuring out what I wanted to do after, I sold my businesses so the first big one I sold was an 18. And I built another one quickly. The first one I sold to a public company. The second one, I also sold to a public company. And then I was like what am I going to do with myself? And I had all these things. I'll do this, I'll do that. The truth is, I didn't know what I wanted to do.

Speaker 2:

How old were you? It was 2018. I'm 51 now. So Congratulations, yeah, thank you. You don't look a day over 51.

Speaker 1:

That's so sweet. So how old were you when you sold the first company? 48. 48. Was it a good exit?

Speaker 2:

It was life altering. Life altering, you know. Yeah, don't have to work ever again if I don't choose to, and could do what I want when I want. I've also determined that everybody's number is different, so others would say, oh, that was a really good exit, but jeez, I need triple that. And here's my answer to that Good for you, and I don't care what you want or need. I know what my life needs to be, so I'm very happy with what it was.

Speaker 1:

All right. So first exit was great. It was to a public company Very creative. That's a great question. Can you say the company or not?

Speaker 2:

Yeah, it's a company called Paychex.

Speaker 1:

Oh yeah, I heard of them.

Speaker 2:

I licensed a piece of software that helped me run the business. They bought that software in 2012.

Speaker 1:

Is that how they discovered you?

Speaker 2:

Well, no, not quite. It was like getting hit and hit with the brick, because we assumed that was the beginning of the end, because they would either be pilfering it, raising our prices, pushing us out of business, because they wanted the market, and most of that actually did transpire.

Speaker 1:

You and I just to pause in for a second. You and I think very much alike, because the company I sold my telecoms to, windstream, bought up all of my competitors, who were also my vendors, and I thought the same way, which is why we had to sell the company before it's time. I knew that they would figure out a way to gouge or pilfer.

Speaker 2:

So I was in the same boat, but here's maybe a modest difference. I was ready anyway, so the stars aligned where I was ready. I had done it for a long time. I wanted to do other things and I knew that was coming, and the multiples in that industry were either at an all-time high or close to an all-time high. So I knew that if it wasn't now, I could be in a struggling situation three years, and I didn't want to do that. So we negotiated the deal, which was an incredibly challenging situation, because these public companies don't do things the way you and I might do them, as you probably well know negotiating with Windstream, and unfortunately, they all say stuff to your face in the boardroom. By the way, that's cactus.

Speaker 1:

Oh wow, that's prickly pear cactus Really Up here yeah.

Speaker 2:

How is that possible? I don't know. Are you sure that's what that is? That definitely is. I think it actually is. I don't know.

Speaker 1:

I'm not touching it, but Listen, I don't know why, I'm just shocked. How is there prickly pear cactus up here? Oh, that looks pretty cool. The cold of New York and New Jersey.

Speaker 2:

It looks a little Sorry.

Speaker 1:

ADHD moment. There we go, let's get back Squirrel, squirrel. It's funny. That was the joke in my office, me too.

Speaker 2:

You and every successful entrepreneur that I know Squirrel.

Speaker 2:

So you know they said things and then the negotiation right to your face and then they'd come back the next day and be like I never said that. Yeah, you know, basically you know that was their tactic to negotiate, but at the end of the day I ended up negotiating a deal for myself and a bunch of other people that licensed this particular piece of software and we all exited around 100 million bucks Wow and Wait, that was your exit. No, no, I wish it was. Mine was a very significantly healthy share, because I was the biggest, you know, licensor. Wait a second, guys, Hold on, Look at the city. Oh yeah, that is an amazing view. I've never seen that before.

Speaker 1:

Someone else at a squirrel moment? Wow, wow.

Speaker 2:

Yeah, all right. So you know they made it difficult, but at the end the deal closed and it was an all-cast deal, no holdback, no provision for losses. No holdback, they just wrote a check for a wired rate of money.

Speaker 1:

I should say, and for those not in the know, the holdback period is the amount or percentage of the sale, usually between 10 and 20%, that the buyer will hold back in the event that the seller has some sort of catastrophic loss in customers revenue Something was not coming to fruition that was promised or earned, or negligence in reporting et cetera. Yep, typically, the holdback is gone. It never goes, or rarely, if ever, goes to the seller. To the seller, yeah.

Speaker 2:

Well, that was my second deal. The second deal didn't go at quite as planned but, you know, at the end of the day, these, you know these, these other individuals trusted me to help negotiate the deal, you know, with Paychecks. And it's not just because I was the largest licensor of this particular piece of software. I just think that they, they trusted me and they knew that I had strong capabilities and I had their help. I didn't do it all on my own. I was the, the person in charge and the final say. But at the end we all had to agree on the number and I had to do some internal selling to get them, some folks, to agree.

Speaker 1:

So you were the consummate salesperson, and that is also the making of a very successful, hustle-minded Long Islander.

Speaker 2:

Yeah, yeah, I guess you're probably right, and I have friends that are operationally-minded, that also have successful businesses, but then they hire great sales. Yes, you know. So they figured out a way around that.

Speaker 1:

There's one really it's very challenging and I don't want to say it's impossible, but it's very challenging to be both the operations-minded person and the sales-minded person.

Speaker 2:

I was okay at the operations Like left brain, right brain, yeah, I mean, like I said, I think I ran a really good operation. But my vice president of operations was my old boss at the first payroll company I worked at and she came with me which was mind-boggling, like she left this good, cushy job to go with a 22-year-old kid Like I still can't believe this day. She worked for me the entire time I had the business. Of course she saw something, I guess.

Speaker 1:

Of course I still can't believe it, but she did. I mean, I think everyone hiking along with us can hear it. You have this swag about you, this hustle, this grit, and if we all collectively think back to our greatest bosses, our greatest managers or leaders, they all have had that. They've all embodied that quality Someone who could talk the talk. Now, if you pair that with doing the right thing, right For your people, and caring about them and nurturing them and not being a jackass in business, then people will follow you. Because what?

Speaker 2:

are they doing?

Speaker 1:

They're aligning their success with yours.

Speaker 2:

Do you have this feeling too? Sometimes, though, I don't want to use the word imposter syndrome about myself, but sometimes I still feel like do I still have it? Yes, can I still do this? And why are people listening to me?

Speaker 1:

Well, welcome to the episode of. I took a hike where it's every single one where I say why are people listening to me?

Speaker 2:

Yeah, but yet they do. And you get up every day still wondering that. But I honestly think if we felt another way, we'd have this horrible arrogance about ourselves. Yeah, they keep you in check, but, by the way, people do. I know plenty of people that probably nobody should be listening to, because I think their advice is stupid and they're stupid and they just have this supreme confidence and it's like I don't even know where that comes from, because you suck, you won't see me on the private jet with my champagne with a bunch of girls and you're like you're not going to see that on my social media. First off, I don't do that, but secondarily, it's just. I just think it's disturbing. But people do it and people follow it because they want to be like that for whatever reason. And then they realize when they get there it's like that's not what it's really, like you know what I mean.

Speaker 1:

I agree with you. I've never wanted to own a plane. I've wanted to be on a plane. Oh, I did. I had a jet for a few years.

Speaker 2:

That's actually the truth, but I didn't have champagne and girls and all kinds of nonsense. Having your own private plane is pretty fucking awesome. It was a little expensive in the.

Speaker 1:

Everett event. Well, what kind of plane was it? It was a Lear 55. That's a real jet. Oh, it was a real jet.

Speaker 2:

No, no, it was a real jet and I flew my friends all over the place and we all had an amazing time. But you didn't see that on my social media. I'm telling you that here, but the reality is you want to know about me, so I'm telling you about my life, but that's a piece of private life for the most part. And my friends would go on vacation. I'd get everybody there and they'd put the bill for everything else. It was not a fair financial trade off, but it's what they could do and it was awesome. We had the best time. We went to go see one of my friends worked for one of the owners of the Milwaukee Bucks. I flew everybody out to a Bucks game. We got a tour of the whole stadium. We got to meet the players, the president of the club. Yeah, we could have done that on a commercial plane, but it's a shitload of funer flying in your own.

Speaker 1:

So I leased it out. But I leased it out though. So I think many people do that. They buy it, they expense it on a business and then they lease it out for a profit center.

Speaker 2:

Plus the tax situation 100% of it was depreciable year one. So whatever you paid for it, if your income was big that year you paid half.

Speaker 1:

Oh really, yeah, oh yeah, oh, that's pretty nice, yeah, so we made a wrong turn. The trail is actually over there, so here we come down.

Speaker 2:

We could probably make it up that way. It's up to you guys Up this way, right.

Speaker 1:

So what is it like owning a private jet?

Speaker 2:

You know, it's just like you see on TV. Here's the man. I was literally talking to my friends yesterday. He's like man. I need to find more friends that have private jets, I was like yeah, well, I'm sure you do.

Speaker 1:

Well, I understand the importance Now. I worked for a company where the CEO did the same thing, had a private jet on the company, leased it out on this person, Right Yay. But that was the downfall of the company because the people then saw it as an arrogant move.

Speaker 2:

This was after I sold the company, so there was nobody that I cared about for you. I would not have done it while I owned the company. I would not have.

Speaker 1:

So here's the thing, though, is you have to understand the importance Now. This CEO needed to be in eight different places in one day.

Speaker 2:

Well then, it was a necessary thing.

Speaker 1:

So if you actually break it down, in that sense it makes sense, because we all know the struggles of going to an airport. You're in for a solid two hours plus Listen you drive up. You can't do that if you have to be in three or four different cities in one night.

Speaker 2:

It's just like you see, you drive up, pull your car up, they take your stuff out and you get on the plane and you go and you're never late.

Speaker 1:

It's your plane, they're going to wait for you.

Speaker 2:

It doesn't matter. That's right. But financially, mathematically, it wasn't worth it, unless you are committed to understand that it is going to cost way more than you think it's going to cost. And you have to have that cost appreciation, enjoyment factor.

Speaker 1:

Well, the deal is not to be worth it for you to support flying to all the places.

Speaker 2:

It was for four years and then it wasn't. And I'm like, ok, I had my fun. Does it get old after a while? No, it never gets old, really, I never even hear the thing. I never even been on a private jet before I bought it. So the brokers, like most people, fly private for a while. I'm like is there anything bad about it? He's like well, I guess I see your point, but the point is I don't miss it. It was a phase of my life. I don't need to ever have it again.

Speaker 2:

What did the cost look like? Well, the plane probably was $3 million bucks and it probably cost a million and a half to upkeep every year. Ok, plus staff. Well, I had two pilots, that's inclusive and then I leased it out and made back probably the majority of it. It still cost me probably a quarter of a million a year. So I mean, if you have a decent amount of money, it is not incredibly painful, but if it was your last penny, I highly don't recommend it. No, and listen, at the end of the day, I'm getting my pilot's license right now. I should have it in about three weeks and I'll rent for a while and then I'll buy a share in this little prop plane that I want, and then my goal in three years is to be able to fly this little single engine jet I have my eye on.

Speaker 2:

But that's not about the swankiness, it's about the accomplishment. I hope I never read about you in the news. I hope not either. But starting the business, though, there was a part that I think would might be interesting, because I didn't just get into business. I had some folks that believed in me when I was trying to license this piece of software. In fact, they wanted me to work for them and open up the Long Island office. And I said I don't want to work for you, I want my own business. They're like well, we're not going to do that. You can work for us or there's no deal. So I made the deal, but it was contingent on the fact that they would allow me to buy the license to the software back if I had certain metrics.

Speaker 2:

They never thought I was going to do it, and I did. And then I had to pay $50,000 for the business that I bought back from them, not even a year later. No way, yeah. And they weren't bent about it. They knew they had to stick to it. Wait, wait, wait.

Speaker 1:

So you have a Barstool Sports Dave Portnoy situation here. Probably You're the original Dave Portnoy.

Speaker 2:

Oh, maybe I'm a little older than him. You know the story right. I know parts of it. I don't know the whole story.

Speaker 1:

He sold Barstool Sports for like I don't know what was it, guys, fact, check me. $500, $800 million Good for Dave, something like that, and they basically gave it back to him for free Because they couldn't figure out how to run it. Right, the PEs couldn't figure out how to run it. It was nothing without him, and the only thing he had to do is agree that if he is going to sell it, the PE firm has the first right of refusal to participate in the deal.

Speaker 2:

Oh, he'd be fine with that. What did he care about that? Probably the end of the day.

Speaker 1:

Well, he's now worth between $500 to a billion dollars and he said I'm never selling this again. Yeah, but he gets to live it. This is great.

Speaker 2:

Good for him.

Speaker 1:

You got to free half a billion dollars.

Speaker 2:

I mean, you know, there's just that story alone and just watching Barstool Sports just come to be, it's just mind-boggling, it really is.

Speaker 1:

Political aside, his hustle and grit is admirable. I agree Because, much like you, nobody can stop you.

Speaker 2:

You know. But the thing is, you believe and this is what I think, I think it's this false narrative that it can be you, and I'm not trying to dash people's hopes and dreams. But you know, it's like you said, it's like me being Michael Jordan. It's just, I can have that basketball in my hand all day, every day, and it's never going to happen. It would have never happened for me.

Speaker 1:

Michael Jordan was Michael Jordan because there are certain genetic gifts that make you just better with whatever you have your mindset. That's true.

Speaker 2:

And you know, I saw something on Steph Curry, who's obviously one of the King of Three Pointers, and I think they said he shoots 500 baskets a day, a day.

Speaker 1:

A day. So that is just a constant. You need to constantly be at it and you know there's no other thought about it. But that's also dangerous too, Because how many other Steph Currys have been out there that have had their hopes and dreams smashed because they dedicated solely to one thing?

Speaker 2:

I think I'm more realistic with my kids and you know, the funny thing is, I don't know.

Speaker 2:

I don't remember a time where they had an outward, maybe when they were very little, they would make comments like that.

Speaker 2:

But you know, in general I think I've been a very realistic individual, but I think the hard part that I'm finding with my kids now is they've lived a life that I did not live. Yes, and that's what I said, I can't relate to my kids. My kids are wealthy, yeah Well, and it's a little weird for me, and you know when they have a certain attitude about something or they're very grateful and they're very hardworking. But I just think they're pretty clear now there's no expectation that they're going to get anything other than my support and they need to do it on their own. And my son has found that out in the last few years and he not only is fine with it, he wants it. He wants to be able to show me and himself that he can succeed on his own. And yes, maybe later on, after they're more established and whatever, I will share more of the stuff or the things that we've accumulated as a family, but I don't see how it does them any good right now Talk to me about running a business.

Speaker 1:

What were your biggest challenges?

Speaker 2:

I think one of the biggest challenges was keeping myself in check and knowing when to be the good boss and understanding and have the proper attitude, know when to be really tough and make your point known, and I think that balancing act is really hard, that combination of loving and hugging and supporting to. You know, I don't want to use the word reprimand, but be difficult to the point where someone's not going to make it on your team. They self-select and they leave before they get fired. And that might seem harsh but it's worked for me and I think it's worked for a lot of other entrepreneurs. You have to have the right skin thickness, I think, to work for most entrepreneurs, because we are a little erratic.

Speaker 1:

Well, it's part of the job. You're working on 50 different things at any given time. What was one of the most difficult days running a business?

Speaker 2:

Probably one of the times when it was Superstorms. Stand to stand in the New York area. For those that are listening, from Wyoming we had a big storm here a bunch of years ago and it wasn't quite a hurricane but wreaked havoc in Long Island I think they couldn't?

Speaker 1:

Oh, is it? The insurance companies wanted to list it as a hurricane For some scandalous, nefarious reason for not paying out.

Speaker 2:

All of that happened, all of the above, I'm sure how New York we lost. This was a building I owned and we lost power, I don't know. So there's multiple phases of power lines coming in there and we lost one of the phases coming off the line. So only half the outlets worked, and we didn't know which ones. Myself, everybody, was scurrying around trying to get power to things. Half of our equipment worked. We couldn't plug everything in, and this was before. I had a new modern building that I bought a generator in, and you have these visions of losing all your clients by not being able to do the job. Oh, if you can't run payroll, well, we didn't pay.

Speaker 1:

There's pitchforks coming at you.

Speaker 2:

Tens of thousands, 100,000 people not getting paid when they probably needed the most because of this storm. And we did it and we got through it. But, conversely, one of my proudest days was 9-11, when they closed all the bridges and we drove all the payrolls for our city clients to the edge of the bridges to pick up their actual checks. Believe it or not, most people still like a live check, depending on the industry they're in. They don't like direct deposit whatever.

Speaker 1:

But you know you did it, but you had a duty to do that I think we did.

Speaker 1:

No, that's one of those where failure isn't an option. You have a duty to do that. So I suffered through Hurricane Sandy or sorry, not Hurricane, whatever we're calling it. I faced that Hundreds of my clients were out of business. They were out of service. What means out of business? At that moment I could relate to that. That was one of the toughest moments. I remember getting on my bike. I lived on the Upper West Side. I got on my bike, dodge trees and debris, got downtown to Wall Street where our office was Went to work Right, and you probably didn't think twice about it either.

Speaker 1:

No, not even a thought. It's the hero, it's the fight or flight, it's the engage when called to action. No is not an option, you just do it, but in a way that became one of the best times of my career and my understanding of what a real CEO should demonstrate. Yep.

Speaker 2:

And your staff watched it. They might not have said anything, but they knew what was happening.

Speaker 1:

No, they said it Because when you have to reflect on those moments, when the dust settles, you have to say, wow, that was rough. That was tough. Nobody gave an excuse. We were all hands on deck. I'm proud of everyone and same thing it's a bit of advice for anyone who works for a company which is everyone Tell your CEO they're doing a good job when they deserve it, because everyone needs a pat on the back.

Speaker 2:

I guess, to follow up your first question, the hardest emotional day was the day after I sold the first business in 2018. Why is that? Because it was this culmination of my entire career and it was over in an instant and the money didn't make me feel any better. You would think it would, and everybody assumes it would. At that moment it didn't. I was quite depressed for a while. It's like wow, ok, I got some numbers and some zeros behind it Digital zeros.

Speaker 1:

Yeah.

Speaker 2:

But that's even a whole other thing. It's like it's not a thing you could touch or feel, it's just whatever.

Speaker 1:

But for me it was very difficult. The intangible that you were told is your life's purpose.

Speaker 2:

Yeah, which I think after, and some of your listeners might not be at that point yet and hopefully they will be after listening to your stage advice, but the truth is I like what you did there, buddy, you like that.

Speaker 1:

That was cute.

Speaker 2:

But you don't know until you're actually in that situation and everybody says, oh, that's bullshit, the money you should be happy, and it's not. If you really think about the human condition, that's not what it is. So that was really a hard day and my wife was like why are you upset? Well, I'm not going to get to see the people that I work with for 20 years on a daily basis ever again. So I was losing that community in a heartbeat and I thought it was really difficult.

Speaker 1:

Did you feel like you betrayed your employees?

Speaker 2:

Yeah, in a way I thought about that quite a bit, but mostly that was weeks or months afterwards and I had private conversations with folks Because the day that I made the announcement was a day that the transaction took place.

Speaker 1:

There was just the way it gets done. There's the gear in the headlights. What do you mean by that? How could you do this to?

Speaker 2:

me. I might assure everybody they're going to have a job. They're like we don't believe you, we don't believe the new people, and it's like people were crying. It was very difficult. Did you come through?

Speaker 1:

with your promise of everyone being employed.

Speaker 2:

Every single one of them not only got employed, some of them made more money.

Speaker 1:

My man audible high five. Yeah, let me tell you, oh, that was a good one, that was a good one, that was, that was healthy it was very important to me, but there was no way I could know for sure that the buyer would actually do it.

Speaker 2:

The only thing I had going for me was that we had such a low attrition rate of clients. Why would they get rid of these people?

Speaker 1:

And you know what they didn't. There are the whys right. Synergization of lots of things increases profitability and a buyer, strategically, could want the most profitability.

Speaker 2:

Some of them got better money because these big public companies have these paydans and scales. They might have been paid well for my world, but then all of a sudden they get this $10,000 increase and they were fairly modest paid people, Tina, who had worked for me for 20 years like Rob, this is the best thing that ever happened. I'm going to miss you, but you know I just got a huge raise and I was like oh, good for you, and we still talk to this day.

Speaker 1:

Yeah, so that's amazing. So you and I are very alike, right? Does that happen a lot on your?

Speaker 2:

show, or does that not happen as often as you would think? Which part that people that you invite on the show are alike, or sometimes they're wildly different?

Speaker 1:

There's something alike about successful achievers, right? It's a mindset, it's that health, mind body connection. It's the doing the right thing for the right people. I wouldn't invite you on a show called I took a hike if I didn't want to spend time learning from you, right? And the people who I like are not the ones flashing the diamond rings, they're the ones that actually give a shit about their people, because that's how I built my career.

Speaker 2:

I left my diamond rings in the car just so you didn't see them.

Speaker 1:

Oh, that's good, just so you know, you did come to a waypoint. Your car might not be there. It's my wife's car. She'll be pissed. That's cool, not my problem. See you. By the way, I got jokes, I can tell. I can tell I'm also a punchy kid from Long Island. So let's get back, because this is a subject you are really meandering, aren't we?

Speaker 1:

It's ADHD and whatever. I got a joke about the drum side I triedomen to. Let's get back to how we relate. The show is all about depression, a massive depression. After exit, depression be unspoken. So talk to me about that. What did that road feel like?

Speaker 2:

You know, I think originally I felt like I shouldn't feel like this. I felt that I was almost mad at myself for not being elated and not realizing that this could be possible, even though people told me it could be possible. So I think I felt a little angry with myself, like this is stupid, Rob, why do you feel this way? And then, after weeks and months of really trying to unpack the last 25 years of my life, it made it a heck of a lot easier. But I understood why. I was upset and it's kind of what we briefly touched on earlier that my world had just completely got blown up and the things that I thought, my entire identity was wrapped up in my business world and even my family, I don't want to say took a backseat, because that's not true.

Speaker 2:

It was different and I didn't see myself as that. I was this entrepreneur, business, people that people looked up to, and then, without that business, what was I? And even multiple years later, I still miss it. I still miss that game. I hustle in a very different way now and I'm being OK with it, but it's very hard to put into words, even though at the beginning of the show I said I could be clear and succinct and get my point across. This is really hard because it's really deep seated in your brain about who you are and what you think is important in this world. And that's what I spent the last few years doing trying to figure out what is really important to me and what am I going to do with the next decade of my life that's going to make me feel important to the world and fulfilled for myself not even for other people for myself, what would you say the number one, the biggest trait that you must embody as an entrepreneur that is poised for success.

Speaker 2:

I would say, the ability to do what seemed like benign things over and over again, so the easier. Put your stick to it in this year. Just your undying labor of love to do things that most other people disdain, to get where you want to go and have that ability to do the repetitious work like a bodybuilder or a weightlifter would, to get up every day and do those reps. Because I look back at my career and I probably was not good at a lot of things, but I just literally kept cranking it out consistently on a daily basis, year after year, even when I didn't want to do it. And I think if you don't have that trait, it is very difficult to be successful in nearly anything, would you agree?

Speaker 1:

entrepreneurial traits. Business acumen is wildly universal, oh, absolutely.

Speaker 2:

Yeah, no, I completely agree, and there are a million examples from my life, and I'm sure yours, which back that up. I don't care what the business is, that's how I'm able to do my business coaching. So I went back and I got certified to be a certified business coach and I've got a very nice client base where I'm helping on a weekly basis and I don't know specifically anything about their industries but it's not urgent. I actually went on. A new client said well, you've never worked in this industry, how could you possibly help me? And I love that question. I had an answer but, to be quite frank, I didn't give him this long drawn out answer. It was very brief and I got to the point and said this is why and he hired me. So I believe that someone that's run businesses and been successful or even moderately successful can walk into somebody else's business pretty quickly and assess the challenges, issues and problems they might be having and outside of math and human emotions, facial expressions, businesses.

Speaker 1:

among the most universal languages, p&l is a P&L.

Speaker 2:

That's exactly right.

Speaker 1:

Profit loss, top funnel, bottom funnel, it's all universal. You're right, you might not know specific industry details, but that's where we ask questions, lots of questions on your normal discovery call right, that's right.

Speaker 2:

I still enjoy those. It's still fun.

Speaker 1:

What would you tell somebody who is maybe your son's age says I want to be a business owner one day. I'm an aspiring entrepreneur or CEO.

Speaker 2:

And you know, fortunately I've got a chance to like Stony Brook University in Hofstra. They asked me to speak to the business school, so I've had these opportunities and the fun part is, you know, you get to really listen to what they want to do and most of the time I tell them I said, just be prepared that it's going to be harder than you ever imagined and it's not for everyone.

Speaker 1:

Not forever.

Speaker 2:

And you know they look at me like that's insane. Of course I'm going to do this. I said good for you. I said but it's OK if it turns out not to be, you know, and kind of like we were talking about before. It is not for everybody for a million reasons, which would take a whole other show. But the simple fact is I don't want to dash people's hopes and dreams like you talked about with your daughter. You were being realistic and I think if I was doing my job right for these young budding professionals to tell them what I really feel, not the hopes and dreams story that their parents tell them.

Speaker 1:

Do you think kids these days are soft?

Speaker 2:

That's a loaded question. Do you want me never to be able to hire a 25-year-old?

Speaker 1:

anymore. I've got you about two miles into this trail with 40 minutes to go. So now the good question is coming up. The answer is the short. You eat the spicy hot wing. Just to shut me up for a few minutes.

Speaker 2:

The short answer is I don't know that soft is the right word. Only because I don't want to be derogatory, not because I'm afraid to say it, but because their world is just very different than mine and yours was. And I think it's no different between the millennials and then you know, obviously I'm a Gen X, and then you've got millennials and the Gen Z and all the other. They've grown up in a vastly different world than we did and I think their vision of the world is so different that we don't have a choice but to deal with the fact that they're wired completely different. Trying to make them what we are or what we want to be is not nearly impossible. I think it's impossible, impossible. So to say that they're soft, I would say that they don't have the same realistic vision of how the world works that we probably did at the same age. Do you think that's a good thing?

Speaker 2:

No, I don't necessarily think it's a good thing. I think it's a much harder thing for them to. They're going to get hit in the head a lot harder than we were, even with the reality of life, and I think most of them will change their tune when they realize it's not what they thought it was going to be.

Speaker 1:

I remember this conversation back. I'm a Gen X as well, I think by like very short period time.

Speaker 2:

Oh, I'm dead in there.

Speaker 1:

I was born in May of 80. So I remember hiring my first millennial and then I remember the whole talk was how millennials they don't want to work, they expect to be the vice president from day one, making vice president salary. Blah, blah, blah, yada yada. I didn't buy any of that bullshit, although I did regurgitate some of the sayings just to fit in Right.

Speaker 2:

That's what good entrepreneurs do with chameleon.

Speaker 1:

But I didn't buy it. I enjoyed it. I'm hiring millennials because I liked that mentality, just like you and I. Everything was possible, right, you didn't want to work for authority because you wanted to be the authority. You didn't trust morons, right, and that's kind of what they were saying. But it is interesting how, when you speak to millennials today, some of them refer to themselves as geriatric millennials.

Speaker 2:

That's because they don't want to be associated with the millennials.

Speaker 1:

Yes, because they actually turned out to be of the same cut as we did in Gen X. It just took them a little bit longer to get there, you, don't think the greatest generation complained about Gen Xers, of course they did.

Speaker 2:

This is also just what it is. Listen, I hired a millennial. That was literally just like you said. I did this one project. Well, I want to raise. I'm like you've been here six weeks.

Speaker 1:

You just started doing it.

Speaker 2:

You're lucky to have a pencil and then they quit because probably their parent told them you can't take that. You did that project, which blows my mind. But then my assistant, christine, who was a millennial because the hardest working person, one of the hardest working people I've ever met.

Speaker 2:

So it's dangerous as stereotyping. Well, that goes with anything. That's why, when you asked me that question, I tried to answer it carefully about their softness. Because not because I didn't want to hurt anybody's feelings, but because I didn't want to sound like a typical Gen Xer that just moaned about the younger generation that everybody does. Truth be told, I like hurting people's feelings. Yeah, that's what your kids told me. They were texting me saying my daddy hurts my feelings. No, I'm going to let that sit for a second.

Speaker 1:

Let's give it a brief moment. We lost Apollo. It's a brief moment of support. Okay, apollo Creed.

Speaker 2:

Oh right, oh I'm sorry. You lost me for a hot second. There I'm like yes, Carl Weathers did pass away. I did hear that. Yes, Apollo, my 88. I lost you for a second.

Speaker 1:

I caught up quick. Okay, so I like strategically hurting feelings. I don't thrive on it, but there's some time that you need to tell somebody, strategically you can't do something. Oh, I agree Because that if you are the right person, you will have a fire lit under your butt as vengeance or prove me wrongedness that will propel you to drive forward, just to do the exact opposite. I think that happened with me on multiple occasions.

Speaker 2:

I think that is a great point and a great story, and I was, when you were thinking, hurt somebody's feelings. I didn't know what to expect from your story, but I think I've done that. But I think I've done that and not realized that I wouldn't have told it the same way. You know me. That's just saying being very direct. You didn't do this. Well, if things need to change, blah, blah, blah, you know yeah, I've hurt somebody's feelings, but I never thought of it that way.

Speaker 1:

Well, live in a world today where we have the illusion of feelings is everything. Everyone is inclusive, I'm sorry. Not everyone's a winner. No, that's entirely true, not everyone's a winner, and that's okay, because not every one of you.

Speaker 2:

I'm not a good bowler. You don't want me on your bowling team.

Speaker 1:

Oh man, I was going to play your bowling next.

Speaker 2:

You know so.

Speaker 1:

I'm not good at that, yeah, but you're admitting it. You are understanding your weaknesses. But if I asked you to go bowling, I took a bowl. Would you do it? Of course, there you go. You're willing to try it.

Speaker 2:

I took a bowl. Wait a minute. What are we talking about? Are we still talking about Naked? Rob understands that one. Just don't call the way I bet you, if you called it I took a bowl or I took a bong, you might get triple your listeners.

Speaker 1:

So yeah, or I might get some portafilter business. There's so many facets to this one, but no, it's when it comes to feelings. I think another marker of a really strong leader is someone that is willing to just come out and say or have difficult conversations An employee is not doing the work that they should. Having that conversation right away in private, criticized in private, right, Facing that and not being afraid to hurt feelings but boost that person up at the same time.

Speaker 2:

I agree, but you know so, like my daughter.

Speaker 1:

Realistically, you're not going to be the first female MLB. You're not practicing every single day and I don't see you doing everything about baseball, right? So, yes, play baseball. I will support you, I'll throw and I'll pitch to you. Absolutely, we'll put you on the team, absolutely. But when it comes to focusing your life not happening, we're going to find something else.

Speaker 2:

You said something about calling out in private and not in public. I agree, except sometimes in the sales meetings where you couldn't really you couldn't help but there'd be a competition in the room, with your sales team sitting there in your meetings and Competitions. Well, that's calling out, whether you did it or not, or they did it by their own lack of ability or effort. That's the simple reality is that when you're in sales specifically, the numbers don't lie. You could be the nicest person in the world and everybody could love you, and even the referral sources or your clients could love you. You sell two deals and your goals are 10 every month, or whatever it is. You're not going to be employed very long. That's right.

Speaker 1:

Getting warm. Now we are on the final stretch, probably about a half hour or so, going on how we make it Nice.

Speaker 2:

This is a perfect leisurely walk. That's kind of a joke. It wasn't leisurely, no.

Speaker 1:

I was breathing heavy while I was talking.

Speaker 2:

I was doing most of the talking while we were going uphill. I think you planned that yeah don't give away some drinks.

Speaker 1:

Tune in every Tuesday for a new episode of I took a hike, posted by me, darren Mass. So let's jump back into business. You said you had sold a second business. Yeah, was that the business that you acquired back for $50,000?

Speaker 2:

No, no, no, that was the beginning of the career. That was the one that I bought at the beginning, was the one that I sold in 2018, the big one. So while I was negotiating the deal to sell my first business, I had realized what was going on and I wanted some soft landing, so I peeled some of the clients off and moved them to a different operating system in that same industry.

Speaker 2:

Now I know what you're thinking and the rest of your listeners are thinking. Well, why would the buyer of your original business allow you to do that and allow you to continue to stay in business?

Speaker 2:

You must be a clairvoyant because I was thinking that, yeah, this is not my first rodeo. And the truth is, I'd love to say that I was such an amazing negotiator that I negotiated them to say well, this is what it is. You want my business, I got another one that does exactly what I'm doing. Too bad for you, let me do it. It's not quite what happened, but at the end they agreed and they let me stay in business with my other business, directly competing with the one I just sold, and I don't think that happens often, if that's ever, it happens incredibly infrequently.

Speaker 2:

Well, this is what I think happened at the end of the day. I think they realized that at some point they'll buy that one, as long as I couldn't steal those clients back, which I wouldn't do anyway because it's not ethical, you know, all right, you're just pipeline for our acquisitions. That's what I think they never said it, but they let me do it.

Speaker 1:

On the way it's future proofing. You've already done it once You've created the successful venture that they wanted to acquire, and I'm sure they're not idiots, right. They're working in Fortune 500 land on purpose.

Speaker 2:

Right Now there are $3 billion. They might be Fortune 100. I don't know where they're at.

Speaker 1:

Yeah, they're pretty big.

Speaker 2:

But then the second one. So I had some clients and I built that and then I really realized I'm like it was much smaller but still significant enough. And another public company I reached out to. This looks like a great deal and they said we want you to come run our sales department. So I took a job. That's a whole story, but I took the job running this other public company sales department. Did you enjoy?

Speaker 1:

taking a job.

Speaker 2:

Ha, ha, ha ha. Listen my friend said you won't last a month. Here's the thing. I lasted nine months at a sheer will. It didn't work. I left. I'm still under an NDA. I can't talk about my experience there. When I can, I will, but you can only imagine what transpired and why I left. But I have to tell you I have a tremendous amount of new understanding of people that work for corporations and why and how they get in a set situation that I will never, ever do again.

Speaker 1:

That I can completely relate to. It's a different world. But it is also the main reason why most of the business owners are exited within a certain period of consultancy time Because it is very hard to transition from being your boss and doing things your own way. In fact, when I was working for Fortune 500, several executives and board members had said to me on numerous occasions well, it seems like we should be more entrepreneurial. And that was basically like them saying bless your heart, ha ha ha, it's funny.

Speaker 2:

You just said bless your heart, because I was literally talking. Now that I live in the South, that's like a thing you say when you're like yourself. I did not know that. No one's actually said that to me other than this conversation, but I didn't know what that actually meant when somebody said it.

Speaker 1:

Yeah, it's like a very sarcastic. You don't know what you're talking about. Good way to shut you up and sound nice.

Speaker 2:

Well, just in general, people that do what we do, and then it's like a New Yorker high five minus four.

Speaker 2:

They get asked when you take the position or whatever and this is just generic. We're going to let you do this. We're hiring you for your skills, we want you to transform, and then they don't let you do anything that you talked about when they hired you. So it's like that story is played out a million times in the corporate culture, in the corporate world. Fortunately, you and I and hopefully soon to be a lot of your listeners or some of them that are already in our boat don't have to make those decisions to work for these companies that don't really appreciate them.

Speaker 1:

Yeah, I mean. It's a choice. We have lots of choices in this world. Now I'm in the camp. If you follow me on LinkedIn, lots of my posts talk about get out and do something on your own. If you're sitting at your desk staring at your glass trophies, wondering why life is wrong and depressing, then go make a change. More so than ever, we all have the power to start a business. Become a 1099 for the very same company we work for. Do something on your own, create.

Speaker 2:

What do you think about the whole just gig economy in general? Quit your corporate job and have three different jobs. I do this. I'm a carpenter and I also knit for a living and I also consult on acquisitions. Like people do stuff like that. You're OK with that.

Speaker 1:

Yeah, I love it. Well, it's a little different, though. I think the scenario you just posed you're describing someone who has to work to feed their family.

Speaker 2:

Right, I talk about regular, everyday people that want to go out on their own.

Speaker 1:

If you have three different industries and jobs, then you're clearly doing this because of a financial scenario in your life. Well, what do you think about?

Speaker 2:

people that you meet out at events and they give you one card. I sell mortgages, oh, and I also work for the sales organization, oh and I also do this.

Speaker 1:

That bothers me actually, Because how can you be an expert? You're not concentrated.

Speaker 2:

I built my whole career on being an expert in a particular field and that's how I built my reputation. And I find that when you're corrupted and you have multiple things going on and they say they're really awesome at all these things, it just can't be, unless you're a savant. It just can't be. So I don't trust them to do anything if they don't do the one thing really well.

Speaker 1:

So I am with you on that. I love the fact that the message is create something of your own, become a solopreneur. I think you and I will probably agree on this. But we'll see. Having employees is daunting, challenging. It's an emotional ride. Your bad employee's bad day is your bad day. It is the toughest challenge that every employer has to deal with and face. It is hard to motivate people, especially when they're in a funk, and it could be a company killer. It's a risk to have employees. Yes, it is. I think you could de-risk very easily by being a solopreneur.

Speaker 1:

Some of us have the capability of having a conversation with our boss, manager, business owner and saying hey, listen, I want to do this on my own. Are you okay if I leave? Take the risk off of your plate, mr Business Owner, hire me back as a 1099 consultant. I'll give you a similar amount of hours, but now it's under my time. Huh, right, that's a great message for a business owner. You're de-risking Now. Obviously it's not so black and white, right. Right, there's some challenges there. Some business owners want to have that employee, they want to have that control, or feel like they have the control, control, the drug Right. And then others, um, hold on real quick Drow. We're going this way, I guess.

Speaker 2:

Oh, I will tell you that Others, others would be okay with that because it is de-risking the business, but you do lose that exact scenario happened with me, and it at several times, and one time it worked out swimmingly well and he went off and did his own thing and eventually left completely and started his own direct competitor. But we worked out such a nice arrangement in a financial situation where nobody got hurt. It was good for him and now he's got a very successful business on his own and I felt great about it. We're still buddies now. Another time it didn't work so well, um, but same as employment Right Right.

Speaker 2:

So your employee's shitty day is your shitty day, yeah.

Speaker 1:

But your vendor's shitty day doesn't have to be yours. That's right, that's exactly right. Right, but there is that aspect. That's a pretty straightforward case. And then there's the other case where it's you're just in a dead-end industry. You're not happy, you want to do something else. I think, more so than ever, you can create your own personal brand strategy and turn it into something if you have that desire.

Speaker 2:

I mean, you know, I look back at all the personal branding that I've done and the personal marketing between the you know speaking engagements where I created this little show, back before the internet was even barely doing any of this stuff. It was just called BASALON business and I went out and fixed businesses and now you can't turn on the TV without seeing a business fix at show. Listen, the production quality was okay. It was okay, but I tried, and what I would do is I'd have a lunch called Working Lunch with Rob. I'd show the little seven minute episode, we'd talk about current events and I'd get a hundred people to show up.

Speaker 2:

So I was it had nothing to do with my payroll business Zero. It had to do with the excellence in business.

Speaker 1:

Excellent business.

Speaker 2:

Yeah, I love that and that's what I've tried to build my career around, because I didn't want to get pigeonholed as the guy that owns a payroll company, because what does that even mean? You?

Speaker 1:

know. So yeah, no, I'm with you. It shows more talent from you and it also is a great marketing tool for clients. Right, Absolutely.

Speaker 2:

I interviewed my clients. By the way, you know, they loved the attention that they got. Well, clients today.

Speaker 1:

Let's look at today the gig economy. Right, let's go back to that topic. Today more than ever, your personal brand as a CEO is your stock to closing the deal, to attracting clients. When I was doing marketing for the telecom company, the marketing people would say, darren, no one gives a shit about you or the CEO of a telecom company. They care about what the company will do for the customer, for them. Today, it's almost the opposite. Today, people are buying. If they align with you, they like you. Because the realization is why do I want to make that clown rich?

Speaker 2:

Well, especially with what I'm doing now and how your career has progressed and we're doing some similar things, some different things I would not get a client unless they aligned with me and saw that I had an image that fit their world, that believed that I could do. Even if they've never met me personally, they'll go and look at all the stuff out there, that's, and if it doesn't fit their world, they're not going to hire me.

Speaker 1:

That is exactly correct.

Speaker 2:

So when you tell clients you need to have a better social media presence or you need to have, and they look at you like you're a deer in the headlight. You know it's not about. You know, are they going to click on that one Instagram post and hire you or buy you?

Speaker 1:

That's I'm not talking about Instagram, I'm talking about LinkedIn. Well, LinkedIn is the most important, critical networking tool that has ever existed, and if you're not on it right, you're not going to put it like this. If you were hiring for a salesperson, they were applying for the job and their interview was going very good. You now do a background check because it's worth it. If you found that that individual that just tried to sell you on hiring them had 77 connections and never posted a thing on LinkedIn, wouldn't that not track?

Speaker 2:

100%, and I think what most employers do is they're not supposed to take certain things into account, but they do. I don't care what the law is and what they're supposed to do I mean, who's not going to look at their LinkedIn page and so forth and you know. That's just what people do. You do a particularly good job at it. I have half as many connections and followers that you do on LinkedIn.

Speaker 2:

You don't put in the time, then I don't and I freely admit, and there's a number of reasons why I don't but the reality is just like we talked about earlier. You're getting the play and the connectivity and what you want out of it because you are dedicating the time, energy and effort, and I'm sure there's some days where you just don't feel like doing it and you're doing it.

Speaker 1:

There's a lot of days I don't feel like. So it's interesting, it's like everything else. It's the dopamine rush. You know, I'll have a post, do very well, and it's all day. I'm on there until my wife makes a comment to me and she goes I didn't see you all day. What do you mean? I hung out with you all day. No, you're in the same room. Yes, you weren't with us. You were present, but you weren't present.

Speaker 2:

See, what's a little different, darren, is I am not going to do that this time around and I'm not judging you at all. I just I'm trying to do this differently. I'm putting the effort in that I think I need to do to get the return that I need for what I want. Your needs and wants are probably different than mine, which is typical. That's just people have different needs of want.

Speaker 2:

I want to be as well as promotion, but I want to be as busy as I want to be, but I also don't know that I want to have 30 people working for me again right now. Or you know, I like the pace that I have now and it also allows me to say I want that client. Oh, I don't want that one. Yes, like I'm not.

Speaker 1:

I'm not vibing with them, I'm not doing that. So now you have earned the right to put up that big poster that says I became a business owner to only do the things I wanted to do. Now, that was before, but now yeah.

Speaker 2:

Right now. But I mean, listen, I think there's a. There's a, there's a happy medium for someone who has like, because you're supposed to have a personal brand. I think I know we're talking about entrepreneurs and business owners, but for those that are listening, that work for a company and maybe thinking about going on on their own or never go out on their own, they still need to have a personal brand within their own organization and people forget that. I have friends that work for these big companies. They don't exist in the world yet they have these jobs and they get paid. Well, nobody knows who they are, nobody knows where it's like. I think it's bizarre.

Speaker 1:

Yeah Well, having having come from the industry that has massive layoffs constantly, it's a routine thing. There are so many people that work their lives off. They've been at that company for X amount of years 10 years, 20 years and they don't have that personal brand and they don't have that direction after the layoff. Yep, you've dedicated. You know it's like you know that age old's factory worker. I've been here forever and now there's no factory. What do I do? We are literally on the final stretch.

Speaker 2:

You have made it.

Speaker 1:

We did, we did you went up a mountain, down. We did. This is a cool little bridge. Wow, what a beautiful. Yeah, this is actually glacial, this bridge. Is it really?

Speaker 2:

Yeah this bridge was deposited by a glacier. Let me get one on our camera with me and you.

Speaker 1:

So how would you say your journey has been along this trail.

Speaker 2:

I'm a little out of breath, which is good, so I got some good exercise. Seriously, I enjoy the conversation because you don't get a chance to have this long of a conversation with most people about the things that you care about, about the things rattling around in your brain that either people might want to hear or might not want to hear, but you want to talk about and I, for me, bouncing interesting concepts and off off of people that are like-minded but have their own perspective on things, is probably incredibly valuable to anybody listening to this, whether they agree with me, agree with you, don't agree with either of us, that's, to me, the interesting part, and they can still enjoy the conversation because they're going to get something out of it. Whether they buy into what we're talking about or not is almost irrelevant.

Speaker 1:

So, rob Basso, thank you for taking this journey with me on this episode of I Took a Hike Appreciate you having me down, it was a great afternoon. Another audible high five come on.

Speaker 2:

Good one.

Speaker 1:

Next time on, I Took a Hike. We finally put the Netflix debate to bed. When we journey alongside the last CEO blockbuster, jim Keys.

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