No Broke Months For Salespeople - How to Spot Untapped Markets Before Anyone Else: Jeremy Delk’s Playbook Part 1

Episode Date: May 20, 2025

Dan Rochon sits down with serial entrepreneur and venture capitalist Jeremy Delk to reveal how to identify business opportunities hiding in plain sight. From losing $2 million in four days to building multi-exit companies, Jeremy shares raw lessons about pattern recognition, authenticity, and why most people never make their ideas real. This episode is your backstage pass to understanding how investors really think and how you can get in the room.What you’ll learn on this episodeUntapped markets aren’t always new sometimes they’re old industries approached differently.Most people fail not because of bad ideas, but because of a lack of belief and clarity.Business success starts with solving people’s problems, not chasing trends.Pattern recognition is learned from losses, not textbooks.Transparency in leadership attracts capital and people masking your weaknesses repels both.Markets reward disruption especially when others say “that’s how it’s always been done.”Real growth starts when you stop pretending to be perfect and start owning your gaps.At the heart of this conversation is a simple truth: real business success comes from clearly communicating value and solving real problems. If you're working to sharpen that clarity in your own business, Dan’s upcoming book Teach to Sell offers a practical framework to help you attract clients and opportunities by leading with what you know.👉 Preorder now: https://www.nobrokemonths.com/teach-to-sell-preorderResources mentioned in this episodeWithout a Plan by Jeremy Delk: A memoir revealing the raw truth of entrepreneurship, risk, and reward.JeremyDelk.com: Jeremy’s official site with contact info, media, and investment updates.Jeremy Delk’s LinkedIn: Where to connect and follow Jeremy’s current ventures.About Jeremy DelkJeremy Delk, Founder & CEO of Delk Enterprises, is a serial entrepreneur renowned for disrupting industries, with ventures spanning biotech, healthcare, consumer brands, technology, building materials, and real estate development. Beginning his career as one of Fidelity Investments' youngest brokers, Jeremy transitioned into entrepreneurship, establishing Delk Enterprises in 2001. Under his leadership, the company has achieved hundreds of millions in revenue and created hundreds of high-paying American jobs.Join us as Jeremy shares insights on embracing failure, identifying market disruptions, and building successful ventures across diverse industries.  To find out more about Dan Rochon and the CPI Community, you can check these links:Website: No Broke MonthsPodcast: No Broke Months for Salespeople PodcastInstagram: @donrochonxFacebook: Dan RochonLinkedIn: Dan RochonTeach to Sell Preorder: Teach to Sell: Why Top Performers Never Sell – And What They Do Instead

And then that's where you're looking for niches to be able to kind of go through and serve and deliver in a different way. It doesn't always work, but you know, you're usually onto something when you kind of go like, whenever you hear that. Keep fucking digging. Cause that's when you're on something. Because if an industry, it just happens and it just happens over time. And I've seen it within every industry.

You become accustomed with these old standardized processes and it doesn't change until someone disrupts it. Welcome to the No-Broke Months for Salespeople podcast, the ultimate destination for salespeople, businesspeople and entrepreneurs. As you immerse yourself in this show, you'll discover the secrets to unlocking consistent and predictable income. We reveal the new way to persuade human behavior

by mastering the art of the teach to sell method. Get ready to transform your approach and achieve unparalleled success. Today, I am joined with Jeremy Delk. And Jeremy and I are gonna be talking about how to spot untapped markets before anybody else spots them. And Jeremy is, he's a money guy, an investor and a serial entrepreneur.

He has done a lot of different work, you know, a lot of different businesses from real estate development to, you know, venture, you know, capital venture and healthcare, consumer brands, technology, and just a whole bunch of different things. And he's joining me today from Lexington, Kentucky. Jeremy, welcome. How are you? Good, Dan. Thanks for having me. You're welcome. All right. So tell us, Jeremy, before we get started, who are you and how long have you been that person? I know you've been that person since you've been a baby, but who are you and And how long have you been that person?

I know you've been that person since you've been a baby, but who are you? And like, how did you become that person? I've had a few iterations, I think. I'm a small town kid from from Bardstown, Kentucky. So it's known as a bourbon capital of the world. So if you've ever had any Jim Beam or Maker's Mark, it's Willett, you know, it's probably from someone I know or went to school with, but it's a small town, like 30 something thousand people,

bigger now, but kind of growing up there, I always had this yearning desire to kind of want to do more, see more and be more. So it actually led me to a short, but pretty successful career on Wall Street in Boston, then in New York. And then about 24 years ago, I went on my own and started Delk Enterprises.

And it's a venture capital firm, early stage startup stuff. You mentioned a couple of different industries that were very much industry agnostic. We write checks in different sectors. The last 10 or 12 years has been predominantly in healthcare. So we've had a lot of exits, taking companies public and private,

tubing 500 companies, which we're really proud of. And now I kind of spend most of my time doing these podcasts, kind of giving back a little bit. I'm an overnight success. It only took me 25 years, right? So trying to share that message. We wrote a book a few years ago that did really, really well. And it kind of just tells the good, bad, and the ugly

of entrepreneurship, right? And it's a lonely place sometimes. So if I can save someone the heartache and all their hair falling out like mine, then God bless them, right? We're good. You and I are too late. We're too late.

We're too late. So you're now how damn it, hopefully one of the listeners can- I didn't read your book, damn it. What's the name of the book you were just mentioning? So the book's called Without a Plan, a memoir of unbound action and failing my way to success. So.

Yeah, overnight success, 25 years in the making. Exactly. So tell me, how did you get into, so you worked on Wall Street for a little bit and then you started your own thing. Was it Wall Street just to go see the world get out of Kentucky and and no no I mean it so backing up a step my dad died when I was young seven and I

think that was like the part that one of the first things that you know definitely fucked me slash shaped me and I think used as a as a massive amount of strength today but I like 30 grand that I was gonna get, an inheritance when I was like 18, right? So it was not a lot of money, but it's a lot from a small town kid. And it was like- For 18, that's a tremendous,

yeah, it's like a fortune, right? Yeah, yeah, so it was in Disney and Disney and in the mutual fund. And my mom actually at 17, I started reading. I knew I wanted to go to New York, I had no idea how to get there. And I was going, my mom, I had to go to college and went to school in Providence, but I took that 30 grand.

My mom let me kind of start trading it. So I was self-taught and I grew that 30,000 into $2 million in a couple of years as a college freshman, which was pretty cool. What was less cool is, you know, late nineties, if anyone remembers that time, early 2000s, the Fonkner was on fire until it wasn't. So that 2000 kind of crash, I was levered up on margin,

which I don't know if anyone knows what margin is, but you can use your equity value to buy more stock on loan. But when it goes up, you make a lot more. When it goes down, you go down a lot quicker. So I lost 2 million bucks in four days, which wasn't super, super ideal. But, and that was like, that was like the worst thing that ever happened to me,

is bar my dad leaving, bar my dad dying. And retrospectively today, I would say those two things are probably, you know, why I'm who I am today. So I think there's a lot of, you know, a lot to be said about things that happening to you versus for you and like how the perspective that you put on there and get them.

But so that's how I ended up falling into Wall Street is like after I made it, I had a really passion with the market and understood it. And that's what kind of got me there. What made me leave was, I was living in New York city in my early 20s, making, you know, you know, a few hundred grand a year. And the guy beside me, I was driving a BMW X5.

They just came out like, you know, there had never been a, you know, sport utility vehicle, like a luxury car kind of thing. And I got brand new with that. I'm just like living the life. And the guy next to me, he had a Bentley, but we were doing the same shit. He was doing it all be at a different level, 40 years my senior. And I had like everyone, right?

These young dumb kids, right? We all have all these dreams and ideas and I would take them. And I was working for Fidelity Investments, which is obviously a massive house, large institutional equities and stuff. And every idea I came up with, no matter what, at the end, I was just making up shit, right?

Fucking fairy, you know, fairies and unicorn, they just, just every fucking idea I had was no kid, no kid, no kid, no kid. And so much, I mean, you hear me speaking, right? I don't sound like I'm from Kentucky. Like I even fucking changed my dialect. Like maybe I just sound like a fucking hillbilly and that's why they don't like my ideas. But for me, and I think a lot of people, you know,

later on I've agreed like corporate America is great for some, but I think it's where you go to fucking die. Like emotionally, that's where you kind of go to die. It turns out I'm a creative. I love, you know, that zero to one thing. Like that's why once I build the Inc. Five, so I kind of bring on management because I don't like that piece of just operating.

That's cool, but I like to be creative and, you know, zig when other people zag and look at these other approaches to business and markets. The best leaders, they don't sell. They teach, they build trust, they change lives. Teach or Sell is going to be published by Post-Sale Press and Simon & Schuster. It's going to show you how to lead with influence, to lead the old way of chasing behind.

Pre-orders are open now. Lock in your copy to visit www.teachyourselfbook.com. That's teachyourselfbook.com. Clay Bodas says you're never going to see again. Your future followers are waiting because people don't want to be sold. They want to be led. It's your time. your followers are waiting because people don't want to be sold. They want to be led. And it's your time.

So I bounced and just said, fuck it. I'm going to leave. And the, the courage to do that, I think was just for making a lot of mistakes because most people, you know, don't, I had a lot of things that were, you know, I had two, two main things that happened. One, I was still young. I had cash. I bought a condo young before I went broke. So I actually made a lot of money, but a lot of money to me at the time.

And I had no kids, no wife, no responsibilities. So like, if it all fucking blew up, I can just go back to Wall Street. Second thing is I ran down like, your SWOT analysis and like look at what, if it works, right, which I think so many people don't think about that question, like what if it does work? Everyone thinks about what if it doesn't work,

but what if it does work? I think that's a very important lens to look at. But on my what if it doesn't work thing, I sketch out and nowhere was there a scenario where I was gonna lose $2 million in four fucking days, get it, right? So I'm like, I've already got through that shit. So what's the worst that could happen?

So that was kind of what gave me the courage to kind of branch out. And I made $7,000 my first year in business. My rent was 6,500 in Chelsea. So it didn't really go far, but I had some savings and yeah, it's been a fucking windy road since then, but I wouldn't trade it for anything. What was your biggest lesson

from losing $2 million in four days? It was more of not like a tactical, like I mean, like there's obviously, it would have been so easy not to lose it just by hedging and other stuff. The, I think the biggest true true life lesson would be twofold. One, be careful of being a victim and things happening, saying, oh, why this happened to me,

and negative, this happened to you or for you. I'm a big believer that things happen for you. And understand that you may not see the lesson for some time, and that's okay. Secondarily, you gotta get understand that you may not see the lesson for some time and that's okay. Secondarily, you got to get the fuck over it, right? Because like that negative feeling like and I didn't it took me four days. I was, you know, waking up to Maria Bartiromo drinking Ackermeyster and fucking until I fucking passed out. Like it wasn't a good time.

But at some point I realized like, well, cool fuck. Oh, like, do you are you are you done? Like and I just like so speed. So I still have feelings. I still like I have all that stuff. But like once you realize that none of that shit's going to fucking get you out of it or be productive, just go through it. So nothing. Don't feel your emotions. Feel them. But just like, cool.

Hurry up on that feeling piece and kind of get back. Get back at it. So let's let's turn into how to spot untapped markets. And through your career, you've invested in different companies, in different sectors, and that type of thing. So walk me through your process of how do you identify something that's worthy to invest in?

What's the pros? What's the cons? What do you look at? Well, the un? You know, what do you look at? So, well, the untapped market thing, let's look at that for a second because it's a bit of a misnomer, right? I think untapped markets don't necessarily have to be like, oh, let's come up and figure out a new market to sell, you know, Pellegrino bottle caps. Like, if you can do that, great. Like, you know, look at what Elon's doing with SpaceX and all that. If you have that big idea, that's great. But where I've made most of my money and successful is just doing things differently. You're a

business coach, you do a lot of stuff, how to do sales and all this different piece. What's the you know, one constant in business B2B, B2C, what's the one constant that is in any business? Well, if you're looking at the constant, it's always gonna be, the first constant is gonna be, do I have business? And then once you have business,

do I have the people and the systems to be able to serve the business? So it's gonna depend on where they are in their business. And then after they've learned that, then am I effectively leading so I can teach other people how to think. So it depends on sort of where you are in the business, but I'd say those are constant for businesses.

Yeah, for sure. But even simpler than that, like if it's a B2B, say how we fulfill diagnostics out for stuff, we have direct to consumer brands, like there's always, no matter what, enterprise level, B2B, whatever, people are still doing business with people. And I think they, people, we forget that so fucking that's number one.

Number two, I don't necessarily care. I'm aware of what's kind of going on within the market. If I'm going into this real estate sector or this, you know, Pellegrino, but let's pick up Pellegrino. I'm going into the sparkling water business. I will, I'm okay into the sparkling water business. I'm okay with being aware of what else is going on in the market, but I don't care. I do not care about competition.

I try to find like, there's going to be a consumer, maybe it's Jeremy Dell, maybe it's Dan that wants to buy this. Why do they want to buy it? What is it? And really just kind of ripping apart and understanding that, that, that core component. And then that's where you're looking for niches, to be able to kind of go through and serve and deliver in a different way. It doesn't always work, right? But kind of going into there, but you know, you're usually onto something when you kind of go, Hey,

I'm going to go into this and well, you can't really do that kid because this is how it's always been done. Like whenever you hear that you're keep fucking digging. Cause that's when you're on something. Because if an industry, it just happens and it just happens over time. And I've seen it within every industry. You become accustomed with these old standardized processes. Like, Hey, that's just how it's always been done. It's a good old boys club. And it doesn't change until someone disrupts it. Travis Kalanick in fucking medallion taxi cabs in New York city. Like that's always what it was. A taxi cab medallion was $300,000 to be able to drive.

You know, it's always that way. But what if there was another? So that's really the kind of point. When you look at untapped markets, I think the markets are usually there and mature, especially if they're a big or a large cam, like a total addressable market. That's the business you want to be in.

And it can be a smaller niche within a regional area or your local area, what have you. But not always looking at what everyone else is doing. You're just going to copy and that's, you're going to be left behind. Cause if you're doing that, the people that are innovating have already iterated and just haven't released their next iteration.

Does that make sense? What if the secret, the top performance is not selling, their next iteration. Does that make sense? leadership and success. Because it's not about pushing harder, it's about teaching people how to think so they choose you. Teach to Sell is being published by Post Hill Press and distributed worldwide by Simon & Schuster in February 2026. We're in pre-sale now. When you grab your copy early, you'll not only be the first in line, but you'll also unlock exclusive swag you're not going to see anywhere else. So visit www.teachtosellbook.com. That's teachtosellbook.com. Pre-order your copy today. Start leading the way the top 1% do.

Teach to Sell isn't just a book. It's a shift that will build your business and your life. You think it does. You think spotting opportunities more instinct or pattern recognition or just pure hustle? What do you think? So I think at first it was hustle, right? Cause I had to look at recognition today. I think it is more, it probably is more pattern recognition because you can just kind of go

through the pieces. Like this, like I just try to cut through as many layers as possible and focus, you know, so obsessively on the customer and the customer experience. Like that, that's, that's the most forward thing. Like I'm opening up a restaurant for my wife. Like they let them do like it's all that level of like, that's true hospitality, but enterprise, you know, multimillion dollar, you know, software license deals. It's still two people like there's going to be you selling it and someone on the other side buying it, right. A contract on behalf of a bigger conglomerate, but that's it. And then have you solved that problem?

And then have you given them enough, you know, you know, confidence and, you know, reassurance and feeling, do they feel like, Hey, Dan, Jeremy is going to be able to deliver for me. So I think it's, it's now adapted into pattern recognition. So that's the first part of your question. The other piece, like, what do I invest in? Like for, if you guys, you know, cause sometimes people get really nervous raising money and kind of, okay, what do I do?

And then they also have this. And I did too. So don't like, but I'm saying this, don't like think I'm like whatever we I had this when I was younger, like, oh, he's got a venture capital firm or oh, he's very wealthy. And I go, well, he has all the answers, bro. If I had all the answers, I wouldn't got my ass kicked. That's really fucking sad. I was like, I got answers, but it's from fucking on the job training.

So it was too many times, right? Yeah, yeah, yeah. But then so then because they because they put this PE group or this venture capital guy, there's other guy, this angel investor, all of which I am, they go and say, oh, well, this guy is all knowing I need to be like him in order for him to kind of go through. So they come in and like, Dan, here's my business.

We're selling Pellegrino as one thing and I've got a derivative spin-out product which are bottle caps and like, I, here's my business. We're selling Pellegrino as one thing. And I've got a derivative spin-out product, which are bottle caps. And like, I've got it. Cool. Especially on younger investors, right? They know all the answers. There is no risk.

They're not scared of anything. And it's kind of going through. So in that scenario, one or both of these is always true. They're either just lying completely or two, they're not intelligent enough to know what they don't know. Both of them will disqualify them for me to invest in them.

I love to invest in people that have been in cycles and like have like, you know, went bust. I mean, bankruptcy, maybe not, but like went bust or had a failure and kind of going through it because that's where you learn those lessons. That's number one. So being vulnerable and like I curse and I yell but I'm a pretty nice guy and people like me

because I'm just my, I am who I am. Like people love me, people don't love me, but it's fine. Like I'm my authentic self. When you can be that and be vulnerable with someone, A, it builds rapport really quickly, right? I don't want to invest in you and find out you're just a scammer or you're lying to me or whatever. So by you being vulnerable, even if I don't invest in you, like, wow, like you're a standup guy and like, Hey, I'm not a good fit because I'm not a good partner or it's not in my thesis, but Hey, go talk to these guys. I would, I would often do that. More importantly, it cuts through the bullshit of if I can help them or not,

because like now if I'm, you know, if I'm Dan, I'm selling you the, the, the Pellegrino and the, and the Padocap spinoff. If I say, Dan, I can sell Ice to an Eskimo. I can do like, I'm, I'm it. I've got the better value prop. We've got better pricing, better value, everything. I haven't balanced my checkbook in 14 years and I suck at numbers. So many people are scared to say that or I'm so scared. I'm scared of sales and marketing, or I have no idea to do that. Fucking great. Good. Just be transparent about you, about the reality of it. And also because that helps me because now I know like, cool, not only do I have money and like often when I invest, I'm giving cash

but it's shared services, cause I've got finance, I've got marketing, I've got legal, I've got those other things. So, okay, Dan, you're a gun at this cause no one's perfect. I'm not, I don't know. I'm like all these Inc 500 companies, it's not Jeremy Delk, it's 200 other fucking people

that built them with me, right? And that team. So I know what I'm good at and know what I'm not good at. I know what I like to do, what I'm not, what I don't like to do. So if you can go through and like get to that point really quick, like, hey, I've got all these things, but dude, this is what's keeping me up at night. If if we don't have this executioner of that, I'm at a loss. Well, OK, now let's go to battle together.

Maybe I can help you or maybe, you know, I can't help you. I've got a business that can't. Or I've got, you know, go to battle together. Maybe I can help you or maybe, you know, I can't help you. I've got a business that can't, or I've got, you know, another buddy investor can. So that gets to a deal much quicker. It gets to a solution because you don't have to invest and wait six months for them to have a mess up. And like, Hey, I'm really kind of struggling.

So it's a hard concept to get around when you put these on, but I've been in the rooms, man, whether it's, you know, Monaco, Grand Prix weekend, or I mean, I've been the billionaires. I brought the, I know that world. Everyone is just the same, man. They just had different experiences and that's it. Viewers and listeners, thank you for your time. Have the best day of your life.

Be grateful, make good choices, go help somebody and God bless you. Thank you. Cheers. Hey there, NoBrokeMonth's listener. I've got some exciting news. We just had 375,000 downloads for the NoBrokeMonth podcast, and I could not have done it without you. I am beyond grateful for every single listener who tunes in daily, takes action, and shares this journey with me. Now, with you and I, let's take it a step further. If this podcast has helped you,

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