Ep 10 - From Paperboy to Payroll Prince: Meet Rob Basso, the Consummate Entrepreneur
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
KEY TAKEAWAYS:
- 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.
RESOURCE LINKS
Fusion Family Wealth - Website
GUEST BIOGRAPHY:
Rob Basso is a seasoned entrepreneur, published business book author, and national business media commentator. As an entrepreneur, he successfully built and sold two Inc. 500 payroll/human capital management companies to large public companies and has been part of many multi-million-dollar deals. Additionally, he co-founded Empire National Bank, which was subsequently sold to Flushing National Bank. He is a Certified Entrepreneur and Executive Coach and has a thriving consulting practice that builds personal brands for entrepreneurs through the power of LinkedIn.
Please click below for important disclosure information. https://www.fusionfamilywealth.com/disclosures
ABOUT THE HOST: Jonathan is the President and CEO of Fusion Family Wealth, founded in 2013 to focus on behavioral finance and guide clients toward rational financial decisions. A sought-after speaker in wealth management, Jonathan previously held senior roles in tax and estate planning at Arthur Andersen. He has a BS in Finance, an MS in Taxation, and an MBA in Accounting. Based in Long Island, Jonathan is active in the local business community, supports causes like the Middle Market Alliance and Sunrise Day Camp, and enjoys boating with his family.
Transcript
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.
're just starting out or are [:And more to share fresh perspectives on making sound decisions that maximize your wealth. And now here's your host.[00:01:00]
s world of entrepreneurship. [: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.
podcasts ago, Cheryl Penny, [: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.
and, and then brought it all [: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.
what I'm finding is that's a [: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.
ven in those early days, you [: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 [: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?
ome healthcare organization, [: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?
[: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.
. He was paralyzed. And [: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, [: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
ags. Filled with newspapers, [: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.
h, how, how you got into the [: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.
u're able to impart today as [:Giving people a foundation now that you and I didn't have,
o: so obviously the book was [: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.
e. My craft might have been, [: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 [: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.
t was time to exit Jonathan, [: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, [: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?
nd barely two years later, I [: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.
almost. And, and people that [:[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.
ecause of all the choices to [: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.
f the things that, um, that, [: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.
ing to do with anything. Um, [: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?
way that they're not getting [: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 [: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.
to this point, so there was [: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.
sophy. Thank you. So for me, [: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 do the things that I do [: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.
ars now. Um, but, but that's [: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
God forbid something happens [: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.
had free time and did what I [: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.
pace with, with some of the, [: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 [: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.
t the, for me, it's exciting [: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.
stantly changing, and I mean [: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.
d star, which was a little s [: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.
when invest and I, you know, [: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. [:Um, I. Um, it still exists,
Rob Basso: believe
Jonathan Blau: it or not.
Rob Basso: There are still legacy seen
through all of that as these [: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.
it'll always succeed. But if [: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.
was, was actually it wasn't [: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.
f his BMW in Bayside Queens. [: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.
he took advantage. I. Um, he [: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.
ther things we wanted to do, [: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%.
w, in your career, you know, [: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
Vaso hope that Glad so do I. [: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.
ostly 'cause he's much older [: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.
he split and, yeah. Survived [: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.
ess very successfully in two [: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?
of my career. So when I was [: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.
ed David McAllister and. For [: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.
l of this, and by the way, I [: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, [: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.
nk they can relate that same [: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.
ou didn't look at your, your [: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.
share, uh, with people what [:Okay, great. Relating to how you help people.
nt, founder. Owner coaching. [: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.
ce where businesses hire me, [: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.
nd of had this epiphany, but [: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.
l tool. If you are not using [: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.
do. We help them come alive [: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.
lf. He became a pilot and he [:Pretty sure you
st difficult thing I've ever [:Jonathan Blau: and I, and again, I take comfort in the fact that you have a plane with a parachute.
[: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?
: Well, we'll be fair to the [: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
t's the pool guy. That's the [: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 [: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 [:Jonathan Blau: I grew up, it was Jonathan r Bl, and I changed it years ago to Jonathan h bl,
ing about that deli sandwich [:If you told them that story, they would look at you like you had nine heads.
most, most stories that you [: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?
is, he is what I thought he [: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.
ll around good guy. And, um. [:Amy Blau: sometimes he enjoys life a little too much 'cause he scares me with that airplane.
ood thing about his, um, his [: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.
dience, I do know Rob pretty [:I do know that he's also very inter mentoring the next generation and yeah, he's mentor the next
eally does. He loves to give [: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
u: what would, what, what is [: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.
able to succeed with it. In [: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.
m gonna, I'm gonna. Tough it [: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.
mmer, and we'll speak to you [:Jonathan Blau: All right, until next time, Jen.
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