The Entrepreneurial Mindset and Tips for Overcoming Business Challenges With Corey Kupfer

Corey Kupfer is the Founder of DealQuest and Principal at Kupfer & Associates, PLLC. He is a deal-driven growth strategist, negotiator, dealmaker, speaker, and attorney-turned-entrepreneur. He founded DealQuest to provide courses, retreats, masterminds, and other valuable content designed to support entrepreneurs, high-level executives, and business leaders in achieving their vision and goals through deal-driven growth.

Corey’s journey into entrepreneurship started at the age of 15. Over the years, he has represented, trained, and mentored thousands of companies and entrepreneurs to achieve leaps in their business growth. He is the author of Authentic Negotiating, host of the DealQuest Podcast, and a member of the Entrepreneurs’ Organization, New York Chapter.

In this episode of the Smart Business Revolution Podcast, John Corcoran is joined by Corey Kupfer, the Founder of DealQuest, to talk about the entrepreneurial mindset. They also discuss the difference between starting a business in 1992 and 2015, the challenges entrepreneurial lawyers face, and tips for negotiating with creditors.

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Here’s a Glimpse of What You’ll Hear:

  • [01:42] Corey Kupfer’s experience running a flyer delivery business as a teenager
  • [06:50] What inspired Corey to go to law school?
  • [09:53] The difference between starting a business in 1992 and 2015
  • [15:08] The lessons Corey learned from two failed business partnerships
  • [18:53] Corey talks about the challenges he faced building his business and how he overcame them
  • [26:10] How to negotiate with creditors
  • [29:37] Why Corey started a virtual business in 2015
  • [33:41] Why many lawyers find entrepreneurship challenging
  • [39:46] How the Entrepreneurs Organization (EO) has impacted Corey’s business
  • [42:22] The peers who’ve had a significant impact on Corey’s life

Resources Mentioned In This Episode

Sponsor: Rise25

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Rise25 Cofounders, Dr. Jeremy Weisz and John Corcoran, have been podcasting and advising about podcasting since 2008.

Episode Transcript

Chad Franzen 0:02

Welcome to the Smart Business Revolution Podcast where we feature top entrepreneurs, business leaders and thought leaders and ask them how they built key relationships to get where they are today. Now, let’s get started with the show.

John Corcoran 0:19

Alright, welcome everyone. John Corcoran here, I am the host of this show and if you are new to this program, go check out some of our past interviews. We’ve got all kinds of interesting interviews in the archives with smart CEOs, founders and entrepreneurs of companies ranging from we had quick and a few weeks ago we got Netflix, we got Kinkos, YPO, EO, Activision Blizzard, and many more. And I’m also the Co-founder of Rise25, where we help connect b2b business owners so their ideal prospects. And my guest here today is Corey Kupfer. He is a deal-driven growth strategist, negotiator, dealmaker, speaker, and like me and attorney entrepreneur, we got to stick together US Attorney entrepreneurs aren’t many of us. He’s also founder of DealQuest, and the host of the weekly DealQuest Podcast, and author of Authentic Negotiating. He’s been an entrepreneur from the age of 15. And I’m going to ask him all about his entrepreneurial endeavors when he was a teenager because I know, I was not organized enough to be making money when I was 15 years old. He’s also a passionate advocate and leader in the entrepreneurial world that evolved in EO, Entrepreneurs’ Organization, which I’m involved in as well, and a renowned strategist on deal driven growth strategies. 

And of course, this episode’s brought to you by my company, Rise25, where we help b2b businesses get clients, referrals, and strategic partnerships with done-for-you podcasts and content marketing. Go to our website at to learn more about it. All right, Corey, pleasure to have you here today. You know, we connected through the entrepreneurial world, and we were chatting beforehand, about at 15 years old, you are savvy enough to go drop in on businesses, and to have a little side hustle, where you convince them that you would go around passing out flyers, which was pre internet days. So you know, people were doing that sort of thing. Some of it still today. But it was, it was definitely a thing back then. But what I love that, which I think is most impactful is that you hired your friends to do the deliveries, which so often, it takes a long time, maybe a lifetime to realize that you don’t have to be the one who’s doing the actual deliveries, you can even get the client. So did you realize that at a young age, or is that something that kind of came after a few years of doing it?

Corey Kupfer 2:22

That was funny, John, I appreciate you having me here. It’s yeah, like I didn’t, I think actively think about it, like then like, Should I do it myself? Or should I whatever, I guess part of it was that the model, you know, the model, the business model, right. And the flyer delivery business, was that the company would hire a an older kid who would drive and then you know, younger kids like me, 1415 years old, whatever it was, who he would, the older kid would drop off, and they would deliver the flyers, and he would drive around and make sure that they were actually delivering them, putting them in the doorways of the fence, or whatever it was, as opposed to throwing them in the garbage down the sewer. Right. So so the model was to have a crew and it just took that to get it out there. So maybe I wasn’t as conscious. But the funny thing is that I am like, I am such a delegator, I had no problem with it most, you know, all of my life, like I didn’t have a tough journey around that. You know, so maybe it was somewhat an eight back then. Because, yeah, I mean, I had, I had a bunch of my friends working for me, and, and, you know, I would I didn’t drive back then. So I did ride around on my bicycle to check up on him.

John Corcoran 3:27

And did you rate were you raised around this? Are your parents entrepreneurs? Do you have it in the family?

Corey Kupfer 3:33

No, this is the strange thing. Like, you know, my parents worked for somebody that their entire life. You know, my dad’s big advice and business and my dad was definitely a mentor. And you know, he became successful in business. But when I was growing up, I grew up in a lower middle class family, we weren’t poor, we had food on the table. And you’re in Brooklyn. You know, we didn’t in Brooklyn, take vacations in Brooklyn. We didn’t take vacations. We didn’t, you know, go out to eat within. You know, it was a big deal. One of my parents when my mother went back to work, and we could afford to go to the Catskill Mountains, you know, for one weekend of the summer. So, you know, my dad was always like, the way you make it is that you become as indispensable as possible to your boss and the company. As they move up, you know, you move up and, and, but always remember, nobody is indispensable. Right. So that was his thing to me, which is great advice. So yeah, I mean, I remember I had one uncle, but But I, but what he would do was sort of strange when I was younger. So it was only like, when, later when I was a teenager, rather than I met, the uncle was an entrepreneur. So I don’t know where it came from. Like, there’s no history other than the fact that I just was naturally

John Corcoran 4:36

a hustler. It looks like you took that lesson about being indispensable to your boss, and you kind of internalized it and applied it to work with clients, maybe.

Corey Kupfer 4:47

Yeah, maybe. And I think, I don’t know, I was always somebody who work. I always wanted money, like, you know, again, I didn’t come from a family where my parents had a lot of money to give me so you know, I was sort of driven to want to be able to You know, whatever I buy my sneakers or whatever it was that I wanted back then. And, you know, and I had done prior to when I was 15, you know, the usual kind of snow shoveling and lawn mowing and whatever. And I, you know, and I guess, I, when I saw this flyer, their delivery business, I saw a bigger opportunity. And I don’t know what had me have the confidence or the hutzpah or the nerve to like, think as a 15 year old kid, I can walk into the local retail store or a candy store or whatever, you know, and say, hey, you know, we can deliver your flyers, but I don’t know, I did. And it worked.

John Corcoran 5:37

And you got to the point where you’re making $300 a week, this is 1976 $300 a week fit $1,200 a month. I mean, that’s like 14 $15,000 a year, which is, you know, in those dollars, and for a kid is just an insane amount of money.

Corey Kupfer 5:52

Oh, it was ridiculous. I mean, you know, it was so much money. And I did that, you know, the only thing that I looked back on it, I realized it and understand back then was I did that for a couple years, you know, age 17, I went away to college. So you know, I did like, you know, 1516, and then 17, I got away to college, and I just left the business I didn’t what I didn’t understand back then was enterprise value. I didn’t understand that I, I should have been, I could have sold that revenue stream, but I didn’t have that concept back then. So when I went to college, I just, I just left it. And then I did other things in college. You know, I was like the plant Rose was the band distributor out there. And they only dealt with one representative on each side of campus at Stony Brook. So for my last two years, anybody who wanted beer delivered for their parties, on campus and Stony Brook and folks think back, this is the time when 18 was the drinking age in New York, not 21. You know, they had to go through me. So I had all these hustles in college, but I but I left that business behind and in hindsight, left some money on the table.

John Corcoran 6:51

And what inspired you to want to go to law school?

Corey Kupfer 6:54

Yeah, so it’s interesting, despite the fact that I have this entrepreneurial thing going on, right, I did come from a very typical sort of low middle class up with Lee mobile, Jewish, and it’s not exclusive to Jewish, but I happen to come from a Jewish background, family who, you know, put a big emphasis on education. You know, my dad had graduated high school and, and gone into the army. And he only went got a college degree like 14 1214 years later, going at night, when when frankly, he had moved up in a company to a point where it didn’t matter anymore. But he wanted it. You know, my mom was was a homemaker at home until my younger brother was in school, and then she went back to nursing school. So you know, it was that very typical next generation, and now kids are going to do better than we are stress on education. So it was like, I think back and I met other kids since then, who took a year off backpacking in Europe, or was a ski bum or whatever, or, like, I didn’t even that wasn’t even on the menu. For me. I hadn’t gotten on a plane since my entire childhood until I was in law school. So it was just sort of like high school, college. And then yeah, I’m gonna, I was in a special law, politics and Community Affairs Program at Tilden high school in Brooklyn, that got me interested in the law. Now, I do nothing of the law that we did back then we would do like trials and criminal stuff, and when, but it got me interested. You know, we visited jails, we did all this crazy stuff. So I sort of went into college knowing I wanted to go to law school, and, you know, just did the thing, you know, went to law school, got a job, you know, high school, college law school job, that was the sort of route? You know, that was, I don’t know, there was only one thing on the menu for me and my family.

John Corcoran 8:32

Yeah, you know, I’m asked sometimes, if I would do it again, if I would go back to law school. And you know, so much has changed in the law? I usually say, Yeah, I probably would, because going to law school teaches you that you know, how the world works, or rather that you can figure out how it works? What are your thoughts on that? Especially today? You know, given what we know now with the changes in the practice of law?

Corey Kupfer 8:59

Yeah, I mean, a couple of things. I mean, I think, first year of law school does a very good job at honing your critical thinking. abilities. Right. I think that serves people, you know, I know so many people who went to law school or on practicing. And, you know, they’re, they’re entrepreneurs. They’re business executives, and other is they want to stop. And I think those skills really, you know, really, really do help. And frankly, listen, I’ve had I, you know, I had a point in my career when I left big, firm, and medium sized New York City practice where I knew I wanted to be an entrepreneur and open a business. I was just deciding whether it’d be a law firm or something else. Right. Yeah. Yeah. I ended up various reasons. I could tell a story going illegal route, but But yeah, I think especially first year law school because that’s where they hone that, you know, Socratic method and the way of thinking and analyzing stuff and it’s, you know, pretty rigorous in discipline. I think that’s, that’s useful. Yeah.

John Corcoran 9:53

Yeah. And use interesting to your career. You started firms a couple of different times in your career. The first time was 1992. The second time I believe was 2005. Time period. And then again in 2015. What’s the difference between what it was like starting a law firm back then? And today in today’s terms?

Corey Kupfer 10:15

Well, first of all, in 92, I had no clients, right?

John Corcoran 10:20

So, you know, when you right out of school then or a couple of years out of school at that point, I was six years out of school.