578 Jim Fitzgerald

[00:00:00]

Founder Bottleneck Teaser

Jeffrey Feldberg: What if the biggest thing standing between you and your next level of your business is not your ambition, your intelligence, or even your work ethic?

What if it's the very way you built the business in the first place?

Jim Fitzgerald grew up in a housing project in Boston, in a world where entrepreneurship was hardly part of the conversation. Yet, while still in high school, he found himself running half the operations of a medical supply business. That early experience planted an idea that would shape the next three decades of his life: business is learnable. Jim went on to build Terradel from a one-man operation into a national direct mail and digital marketing company, servicing more than 25,000 small business customers and generating 30 million in revenue before he sold it.

Along the way, years spent inside CEO roundtables showed Jim something surprising. Even highly successful founders repeatedly [00:01:00] struggle with the same things: broken systems, bad hires, unclear priorities, and businesses that depend far too heavily on the founder. Today, through Fitzgerald Growth Partners, Jim helps founders identify the real constraint holding their businesses back and build companies that can grow without the owner carrying everything.

He's the author of The Million Dollar Hurdle, a USA Today bestselling book that reached number one in five Amazon categories and distills nearly four decades of business-building experience into a framework for moving beyond effort, chaos, and chance.

Jim Fitzgerald has spent decades learning what actually separates a hardworking founder from a scalable business, and some of those lessons challenge almost everything entrepreneurs are taught to believe 

Sponsor Deep Wealth Mastery

Jeffrey Feldberg: And before we start the episode, a quick word from our sponsor, Deep Wealth and the Deep Wealth Mastery Program. Here's [00:02:00] Sanjay, a graduate of Deep Wealth Mastery, and he says, the investment I made in the Deep Wealth Mastery Program, it's a rounding error compared to the value created today and the future value I'll receive.

Or how about William, who says, and I love this, A company that's attractive to sell is also a great one to own. The Deep Wealth Mastery Program gives me the best of both worlds. 

Now speaking of growth and adding value, check out what Leon says. He says that the Deep Wealth Mastery Program changed how and who we hire. We've now begun to hire talent today that we never would have hired if it weren't for the program. The talent we're hiring today is helping both increase our growth and profits and our future enterprise value. 

Man, I love that kind of feedback because it's that kind of feedback that's what gets me out of bed every day.

Deep Wealth Mastery System, it's the only system based on a nine figure deal. That was my deal. And as you know, I said, no to a seven figure offer, created a system that we now call Deep Wealth Mastery, and that's what helped myself and my business partners all welcome from a different [00:03:00] buyer, a different offer, a nine figure deal.

So if you're interested in growing your profits, preparing for a future liquidity event, whether that's two years away or 22 years away, and if you want to optimize your post exit life, Deep Wealth Mastery is for you. Please email success at deepwealth. com. Again, that's success, S U C C E S S at deepwealth. com. We'll send you all the information about Deep Wealth Mastery, otherwise known as the Scale for Ultimate Sales System. 

That's where you want to be. You want to be with other successful business owners, entrepreneurs, and founders, just like you, who are looking to create market disruptions. Whether you're a startup, whether you've been in business for three or four decades, whether you're manufacturing, whether you're high tech, SaaS, low tech, whatever the case may Come in and network with other business owners, with other businesses, just like you, because they all want to lock in their financial freedom and enjoy both success and fulfillment.

Again, that's the 90 day Deep Wealth Mastery program. It has your name on it. All you need to do is take the next step. Please send [00:04:00] an email to success at deepwealth. com. 

Podcast Welcome And Guest Intro

Jeffrey Feldberg: Deep Wealth Nation, welcome to another episode of the Deep Wealth Podcast. Well, Deep Wealth Nation, let me ask you this, because you know I love my rhetorical questions. For all you founders out there, when you look at here to there, how are you doing? You feel good about that, or are you waking up, oh, no, same blank, different day?

Lots of questions. How do we get from here to there? I have a very special guest in that house of deep wealth. Not only a post-exit entrepreneur, he's a thought leader, an author, someone who is really making a difference for founders, business owners, and entrepreneurs. I'm gonna put a plug in right there.

Jim, welcome to the Deep Wealth Podcast. An absolute pleasure to have you with us. There's always a story behind the story, and I know in preparing for today, wow, you've got quite the story. So what's your story, Jim? What got you from where you were to where you are today?

Jim Origin Story

Jim Fitzgerald: Well, first of all, thanks for having me, Jeffrey. I'm uh, kind of pumped about this episode. the entire topic in which you focus on is near and dear to me. I have to go way back. So, high [00:05:00] school I was fortunate enough to get one of those part-time jobs that made a difference, and I worked for an entrepreneur.

I grew up in a housing project in Boston. And I think aspirationally w- what a lot of my friends were looking forward to was, maybe landing a job at City Hall or the post office. But I was fortunate enough to work with a guy who he was tough but brilliant and ran a medical supply business.

And over four years I learned an awful lot about him, but I think the biggest takeaway was Owning and operating a business, once you get past the concerns that I think everyone has about the financial side of getting it off the ground

Isn't terribly difficult if you look at it with the right perspective.

But you have to be given the opportunity to get that perspective. And if I dig a little bit deeper I think if you look at a lot of folks, a lot of your listeners, there [00:06:00] was probably something in their past, whether it was a family member, a family business a colleague friend, somebody who had taken a leap.

And I think getting exposed to that had a big part of kind of where I am today. So rather than being intimidated after that experience, I was encouraged. So it didn't happen right away, but I did start not too long after that a small business working out of a spare bedroom, and had some success with that, made a living.

But decided at that point I had a couple of kids landed a job with a publicly traded business and paid my dues but learned quite a bit. 

Building And Exiting Taradel

Jim Fitzgerald: Got involved in yet another opportunity, started my second business. Did pretty good there. Had a successful, small but successful exit to a private equity group that was doing a roll-up.

Fast-forward again, I worked with another company that was doing something very [00:07:00] entrepreneurial for that business, and they wanted me to run it. That worked out great for about two years, but they could never really leave their core business in the right place. So every time my, let's say, entrepreneurial startup had any kind of momentum the core business stole it.

So finally one day I walked into the CEO's office and said, "You guys aren't really doing anything with this." I'm gonna move on. So we had a I think an amicable split, and that's when I started Taradel which is the business I spent 20 years building. And had a successful exit from there in late 2024.

But the experiences I had at Taradel encompassed both the opportunity to sell going through a process with an investment bank in two different occasions not selling the first time and successfully selling the second time. But the other highlight there was we created a, direct marketing platform for SMBs, for small businesses, and [00:08:00] over the 20 years we worked with over 25,000 of them.

And when you work with that number of businesses whose resources are precious and few you get a real solid understanding of what's required to make them move and grow. But also on a human level you really get to appreciate just how difficult this is because you, bring your own experience, but when you're involved with that on a daily basis, it has real impact on you as a human.

So That's how I get to where I am. And most recently I co-founded PaySile with a partner, and that's a business that manages... Total departure from marketing, but that's a business that manages it's a software application that helps with payments and reconciliation.

So, and that's where I am today. And finally my real passion is coaching and working with small businesses trying to get them over what I wrote a book about, which is called "The Million Dollar Hurdle." And many [00:09:00] businesses struggle with getting not only to that first million, but maybe to that, whatever that level is, it might be 5 or 10 million, where suddenly they've got a repeatable business model and something that has real value when they go to sell.

Jeffrey Feldberg: so many questions, so little time. But let me ask you this because it is a Deep Wealth Podcast after all, and of course, we do focus on the founders who, "Hey, I just want to grow my business. I want to grow the profits, no plans to sell." And then the others who, "Yeah, I want to grow my profits.

I do want to have some kind of an exit or get an investor in." If we could cherry-pick, Jim, where you are today and looking back at the different exits that you did have, is there lessons learned? Is there any one lesson learned that you can share with Deep Wealth Nation of either, "I would've done more of that or less of this," as you look back at the exit?

Exit Lessons Culture And Decisions

Jim Fitzgerald: Yeah. Couple things. I think maybe the most important one is culture. 

Jim Fitzgerald: And you know, I joke with whenever I speak [00:10:00] with business owners I say, when we talk about culture I say, "First of all, don't worry, you have one. Whether you like it or not is something else." And, I remember years ago, having a need to bring some people in 'cause we were growing, and, just hiring for skill versus culture fit and I paid a price.

And I remember going to the office and I wasn't terribly happy about the experience I had when I got there. And I was fortunate enough to hire a woman 16 years ago who had a really good handle on culture and, and how to build it. And one of her statements that I never forgot was, you know, when, when you go to work every day, very often you're spending more time with the people you work with than you are with your own family.

And that, that kind of hit me between the eyes. So we were much more judicious and careful and strategic about hiring going forward. And by the time I sold Taradel I think we had 40 full-time employees, and I'd be happy [00:11:00] going out and having a beer with any one of them. sounds like I'm focusing on the personal level, but what really happens is the chemistry and the productivity when you have the right culture and the right environment, people that really believe in your values and your vision it's a force multiplier, and incredibly powerful.

So that's one thing. And the second thing which I share with everybody who asks is the older I got, the longer I was in business the more decisive I got. And you've, you have a lot of experience in your lifetime. whatever it is you're doing that you decided to follow, what you're passionate with with your business, trust yourself.

you've got a ton of experience, you know what you're doing, you're the subject matter expert. When it comes time to make a decision, do it. And it's not always gonna be, but here's the takeaway. Whenever you make a decision, you have a data point

And you know going forward that, okay, that didn't work out so now I can decide to do something else.

Call it [00:12:00] AB split testing, call it whatever you want, but if you don't make that decision, you're just gonna flounder. And I just encourage every- because I see it all the time there's that old saying, you know, "If you've made a decision not to make a decision, you still made a decision."

It's just that you didn't learn anything from it, those are my two big offers of, whatever wisdom I've collected over the years 

Jeffrey Feldberg: Absolutely terrific, and it's interesting just before we'll talk about what you're doing now and the book and your team, when you go to culture, it's interesting that you pick that. And I know for us here at Deep Wealth, in the Deep Wealth Mastery program, the 9-step roadmap, Step 2: X-Factors, every business has something that is unique.

And when it comes to an X-Factor, it's what they're unique in, what makes them special. Most businesses are maybe three to five X-Factors. Some of them are so special we call them the hidden Rembrandts in the attic. You may not even realize that you have it, but this is what helps you keep customers, get new [00:13:00] customers, and add tremendous value.

Culture is one of the flagship X-Factors. All the money in the world that the competition has, they cannot buy... If it's a great culture, they can't buy it and replicate it on their own. It's like a fingerprint. So it's interesting that you mention that. And Deep Wealth Nation, how's your culture? What's it like?

Is it toxic? Is it rich? Is it thriving? Something that I'm sure we're gonna talk more of. 

Not Revenue Structure Problem

Jeffrey Feldberg: Let me ask you this, because very early on when I was thinking about s- talking today and doing some of the background, and in fact, it- it's right on the website, one of the first pages that I saw, it says, "It's not a revenue problem, it's a structure problem."

And for most founders, they're confusing activity with progress. "Yeah, we don't have enough revenue, but it's this or a side," and it's actually a red herring, a- as the saying goes. what do you want Deep Wealth Nation to know of, well, yeah, this is [00:14:00] why it's not a revenue problem, this is a structure problem.

And not to make the question already more complicated than what it is, is it the good old Pareto's law, the 80/20 principle, that, yeah, Jeffrey, when it comes to a structure problem, 20% of these specific items over here are creating maybe 80%, maybe it's 90/10, 95/5 of the so-called issues, otherwise known as opportunities.

What are some of the patterns when it comes to structure that you see that you'd want Deep Wealth Nation to know about?

Jim Fitzgerald: Yeah, e- excellent point. Is it... I think you read the book. So I specifically talk about the Pareto Principle in it, and I think that's a very valuable way of looking at the world in general, particularly in business. 

Founder As Bottleneck Framework

Jim Fitzgerald: What I see very often is, I I hear things like, "I don't have enough time."

things don't flow the way I'd like to." And when you drill down, very often it's the founder that's the bottleneck. And, And we all go through this. It's your [00:15:00] baby, you built it from scratch, and back when you started you had to do a lot of those things.

But if you break those things into buckets, and let's keep it real simple. You've got $10 an hour work, $100 an hour work, $1,000 an hour work, $10,000 an hour work. You wanna get, y- you wanna get your, founder brain on the far right of that conversation. You don't wanna be doing $10 an hour work.

You don't wanna be the bottleneck when there's a customer service issue. Somebody should be able to address that. There's nothing wrong with getting to a point where it gets elevated, and maybe you have to step in occasionally, but don't be the bottleneck. that's something we talk about. But getting to structure yeah, these again are force multipliers. If you have a system in place that you can leave and the business runs, that is incredibly powerful and has a dramatic impact on your valuation, which I'm sure we're gonna talk about more. But [00:16:00] if you're a founder and you're heavily involved in the day-to-day, your business value is going to be reflected negatively as a result of that.

Now, if you can confidently say, " I can go to Italy for a month, and I come back and the business is just as well as it did the month before," now we're getting somewhere. So invest in the things that you need to do. And one of the things we did in the book The Million Dollar Hurdle, was what are those things?

Scorecard And 80 20 Focus

Jim Fitzgerald: And very often business books can be a bit tedious because you pick it up and it's like, "Okay, some of the stuff seems redundant to me. Some of the stuff I'm aware of. When am I gonna get to the point where I see real value?" So as somebody who's read God knows how many business books, we put very early on in the book a scorecard, just 25 questions that are broken into five different areas.

Things like credibility, things like what's your revenue flow, culture. And we help the reader [00:17:00] identify where the biggest holes are. Where is that 80/20? Where is the 20% of the things that are causing 80% of the problems? And once you do that, then we direct you within the book- To go to the appropriate chapter so you're not wasting any time.

Because some folks could have a terrific culture, and it's not an issue. Some people present like they're Proctor & Gamble even though they're a small business because they've paid attention to their brand and how the world perceives them. But many others have not.

And these are the areas where we wanna help them focus their energy because, time is the most precious commodity of them all. So they're not wasting time and they're going right to it, r- right to the things that are gonna make the most profound impact

Jeffrey Feldberg: My goodness, so much there. And by the way, Deep Wealth Nation, go to the show notes. Everything is there, including the link. Pick up the book, The Million Dollar Hurl: How Small Businesses Can Leap to a Seven-Figure Revenue and Beyond. And you know, Jim, I love how you structured the book. You have 16 different principles across four different parts of how you put [00:18:00] it all together, and it's interesting, it's sequenced, it makes a whole lot of sense.

And I love one of the questions that you asked earlier, Deep Wealth Nation, does your business run without you? This is one of our favorite questions when someone comes into the Deep Wealth community. "Hey Jeffrey, does your business run without you? Please, yes or no." No stories in between. And Jim, we rarely get a yes or no.

Usually, "Well, but..." Or, "Let me tell you this." Or, "Well, kind of," which really means no, it doesn't. Even the business owners that have a leadership team, if they're honest about it or we speak to the team, yeah, no, everything's gotta go through the founder and the owner. 

Enterprise Value Even If Holding

Jeffrey Feldberg: And so Jim, I want you and I now to speak specifically to the founder who at least right now is thinking, "No interest in selling the business.

I'm gonna do this forever. I'm young, I have a lot of runway, or I'll have the next generation come along and they'll just pick it up." How that, on the one hand... I think that's part of the equation, because my equation has always been [00:19:00] run the business like you will keep it forever on the one hand, then on the other hand, as though you're gonna sell it tomorrow because it creates a healthy tension.

But for the founder who's thinking never wanna sell it, you and I are talking about enterprise value, two words that are very fancy, which essentially means what's the business worth? So if an investor were to come in to invest in the company or a buyer were to come in to pick up all the company, this is what they would pay for that.

Even for the founder who says, "No interest in that, not even in my world right now," why is that something that is of high interest for them if they wanna have a business that's gonna be in business, and what they may unintentionally be doing to lower that value? What would you say to that founder?

Jim Fitzgerald: Yeah. No it's a great question. I go back to my own experience. and by the way, I've been that founder, so, I hear this question loud and clear. when I ran Taradel, we had an opportunity to work with take our application and white label it for [00:20:00] Staples, the retailer.

They have print and copy centers at their locations, and they thought one of the things our platform did was simplify direct mail, for instance. And they loved what we were doing, and they said, "Hey, can you white label this and train our sales team on how to sell it?"

And we said sure. But in the process, their business development team picked up the phone and said, "Hey we're, somewhat interested your business, and we'd like to talk to you further about possibly acquiring it." So when that happened, and that happened out of the blue, I was not expecting that.

So when that happens you can't just say, "Okay." You have to create some kind of mechanism to see what your value is.

And hopefully create an auction, so we had an investment bank and we went through the process. And the reason I'm telling this story is by the time we went through all that, and we were very well trained with the banker.

They did a superlative job. But when the actual letters offers came in they were far below what I [00:21:00] had anticipated. And The good thing, here's the good news. I learned why the biggest hole in our portfolio was we didn't have enough recurring revenue.

That's a very powerful value driver. So I took that amongst some other things. We won't get into the weeds, but I took that big lesson and incorporated that into the business and, seven or eight years later when we went back to market, it had a profound impact on the valuation. So that's my point, is if you're not planning on selling, go through an exercise.

bring in a evaluation expert, somebody that can poke the holes in your business, and I'll tell you why. Y- your business will be more valuable you plan on holding onto it forever for your heirs, or... But I think what's more important is by creating a more valuable business, you're probably gonna create more cash flow.

If you create more cash flow, you're probably gonna get the best thing in the world, which is the opportunity to take some [00:22:00] time and enjoy the fruits of your labor. And I can tell you at my age, that is a very appealing proposition. Probably just not something I thought a heck of a lot about when I was 30 or 40, but the age I'm at now, it's huge.

And you will, trust me, you will get there. God willing, and gonna be happy that you have a business that can sustain itself, that where you've learned some lessons that have had a big impact on profitability, valuation, and a machine that just runs better, so you have the freedom to do some of the things you wanna do

Jeffrey Feldberg: Absolutely. 

Unsolicited Offers And Auctions

Jeffrey Feldberg: And Jim, one of the sayings that we have at Deep Wealth that tie in exactly to what you're sharing, Deep Wealth Nation, for us, one is never a choice, two is a dilemma. It's when you have three or more options or choices, now we're talking. And to what you're saying earlier, there's a reason why buyers, and I have them on the podcast, no deference to them, they're playing their role, they're doing what they're doing.

There's a reason why they [00:23:00] love the unsolicited offer. They're catching the business owner off guard, and they're likely gonna pick up the business at a much lower valuation than, Jim, what you did or what I did. Hey, let's have a process, let's have an auction. It's gonna be more than one buyer. It's like I'm gonna go buy a house.

If I know I'm the only buyer looking at that house, I'm gonna have a lower number. I'm probably gonna have all kinds of conditions versus if I know, hey, there's other buyers here, maybe I'm gonna do no conditions. Maybe I'm gonna come in at a premium. I don't want to lose this house. It's the same thing when you have that.

And in fact, Jim, I... True story to really the point, I've only heard of one instance where the unsolicited offer was the way to go, and it was one of the co-founders of Waze. And he said, "Yeah, one day," this is back in the day, "we had faxes and we got a fax. I thought it was a hoax. It was from Google. 'You have 24 hours.

We want to buy your business for a billion,' with a B, 'dollars.'" And he said, in his words, "I thought about it. Could I do it on my own? Maybe. Or [00:24:00] should I take the offer? Let's not find out. Let me take the offer." And in that instance, probably one of the only times that an unsolicited offer would make sense all the other of...

 they have their fox traps and the buyers are waiting for you. We see all the zeros as founders. It's human nature that we just lose the rational side of things. 

Managing People Without Micromanaging

Jeffrey Feldberg: I want to circle back to the book and so many principles that you're talking about, I want to go back to chapter six, principle six.

You're talking about managing your people. And I know for me, Jim, a- as a founder, I would give myself a failure grade, an F, because I perhaps expected too much or I was too little prepared or I worked them too hard or not enough that I found myself as the weak point for me, if I'm really honest and looking back.

So with what you're doing now, e- even at PayStyle or even the different companies that you're in, when it comes to our people, our team, and we spoke about culture earlier, what would you want [00:25:00] us to know?

Jim Fitzgerald: Yeah, I think my experience over the years has led me to a strategy that's very... I don't want to say it's entirely hands-off, but it's as close to hands-off as you can get. I- I'm a huge believer in hiring the best person for the job, obviously that is a culture fit. There's two boxes there.

But here's the third part: leave them alone bright, aggressive in a good way ambitious people love independence.

And as long as they're moving the puck in the direction you want it to go, leave them alone. And I see it all the time when it doesn't happen that way, and people just naturally get frustrated, and it's usually something like I'm getting mixed messaging.

One minute she wants this, another minute he wants that. I feel like it's schizophrenic versus you come in you shoot the breeze over a cup of coffee every couple of weeks and, catch me up. [00:26:00] What's going on?

And now not every worker likes that. You know, That there are some people that, want maybe a bit more mentoring.

 my philosophy is If you can, get people that are past that point. Get people that are like they're busting out. They're quite frankly the ones that they're probably gonna do the same thing you did. But that's what you want to surround yourself with future founders.

Jeffrey Feldberg: It's a tough question I'll throw out there. There really isn't one answer fits all for everyone. It's always situational. And again, I'll use two fancy words. On the one hand, we have delegation. "Okay, I'm gonna delegate Jeffrey or Jim. Hey, you're a rock star, Jim. Go do what you do best. I'm not gonna micromanage, and off you go."

And then you have abdication, and again, another fancy word. "Okay, Jim, here you go. This is the goal. Let's check in this time next year and see how you're doing." So you

have the micromanaging 

Jim Fitzgerald: thanks for calling that out. that's a very important point. And I'll tell you what I did. I had a COO that would wear a lot of [00:27:00] the hats I did not wanna wear.

And I think I was in my element when me and whoever was on the other side of the table was talking when we were both interested in the discussion versus, it's time for your annual review."

That was not my cup of tea. Or what are we going to do about this new policy?" And I would lean on my COO and say, "That's, whatever you think makes the most sense." Now, that took time and an incredible amount of trust over the years. But it's really important that you point that out. I don't think I abdicated as much as I had somebody I had delegated to take care of that level of detail to make sure we were checking the boxes, that people found growth opportunities within the business. That if they required training or they wanted additional education, that we made that available to them.

and coaching there were enough executives that we had some talented people that could share that with them. I was more interested in what they were working on [00:28:00] and how that was impacting the total strategy. And again, maybe my instance, I was fortunate enough to get the right people for that environment.

But then again it all comes down to the culture. Some people want an awful lot of attention and they thrive in that environment. And then you've got other people... I worked with a lot of engineers. And I think anybody out there that does, I think this might resonate. The independence with engineers I think is somewhat critical.

Jeffrey Feldberg: So being the smart founder, it's, okay, Sally wants this, Jim wants that, and I'm going to cater to what they want, not what I want necessarily, but what they want in terms of what works for them with their personality style and recognizing that. I hear that a lot, and it's some great advice. 

Founder As The Hurdle

Jeffrey Feldberg: and then again, circling back, you call it the million-dollar hurdle.

Let's look at the hurdle, because quite openly it could be a million dollars, it could be a billion dollars, it could be $3 million or, or 10. Who knows what it is in terms of the number? It almost doesn't [00:29:00] really matter. I'm wondering, as we go along the different revenue numbers, and again, fill in the blank, the hurdle is often coming back to the founder.

And so I would love your thoughts on does the hurdle ever really disappear? I mean, Truly, if the founder is the hurdle in so many ways, does it ever go away or that's always there, and what do I do as a founder to manage that?

Jim Fitzgerald: I think every founder listening i- we've all got the same disease, let's face it. That, that is a it's the journey is the reward, there is no end.

there are goals and numbers and budgets and things, and I think th- those are all important parts of building any business.

But I think a- as, as long as you're, looking from a sales perspective on the chart up and to the right, and expecting that and doing the things you need to do to make sure that continues to happen, I don't know what the number is. I mean, ask, Musk. I don't think he knows.

 it never [00:30:00] stops. But again, I think what attracted me about that particular title and that number is, you know, there's 35 million businesses the, in the US, and a fraction of a fraction get to a million dollars. I just think that was just a nice line to draw that I think a lot of people could associate with.

But I'm glad you called it out because I don't think the book is for somebody trying to get from 750 to 1.1. I think the book is for anybody trying to get to that next level. For somebody who's gone through a few of them. And I wish I could define a way to get founders to stop thinking, about billion whatever it is.

if the day that happens I think we'll all suffer. But I think a lot of people just need a hand up to get, you know, the enough acceleration and momentum to get to that next goal that they're trying to achieve. And to me, it all comes down to, are you scalable?

Jeffrey Feldberg: Yeah. 

Jim Fitzgerald: that's, maybe a, a good way to wrap that particular discussion up.

New Levels New Blind Spots

Jeffrey Feldberg: What I love though with what you're [00:31:00] doing and how you approach this in Deep Wealth Nation, I want you to think about this for a moment. Again, you can fill in the blank. A million dollars, a billion dollars, anything else in between. As a founder, it's the next level of business, whatever number happens to be associated with it will bring on with it, not bad, not good, not putting labels on it, just new levels of challenges that are likely going to expose blind spots in the founder that weren't relevant before.

So as a founder, if you're over the $10 million mark, just to pick a number, and it could be any number. Well, when you get to the next level, 30 million, 50 million, 100 million, there's gonna be new challenges there that you haven't had to deal with before that the hurdle, otherwise known as the founder, will reappear.

It's always been there under the surface, but it's like peeling back the layers of an onion, as the saying goes. And as we go up that revenue ladder or the profit ladder, there's different hurdles. [00:32:00] And really the question is, Deep Wealth Nation, are you the emperor with no clothes? Do you have yes people around you who are gonna help you identify it and call it out?

Or are you checking your ego at the door and you have some tools, like what Jim has done with The Million Dollar Hurdle and a great culture and a great team, "Hey, Jeffrey, past few times, you never come across this before, but this has become a challenge for us, and let's figure this out, all of us, because I, think as a company we're failing, so what can we do about that?"

Jim, would love your thoughts on that.

Jim Fitzgerald: Yeah, agreed. 

Fundamentals Mini MBA

Jim Fitzgerald: I think there's, Going back to something I said earlier about decisiveness, you know, trust what you know. But I think some of the smartest people I've ever met are the ones, the first ones to admit what they don't know. And that's where if you have a framework, if somebody describes to you here are the foundational pieces you need to scale a business." And let's say finance isn't your strong suit. You know how to [00:33:00] read a P&L, but you really know what a balance sheet is? I bet there's a lot of people listening right now that are nodding their head, Well, that's probably something you might wanna bone up on. And try to get ahead of it because as you grow, all of these things are going to... whether the hole is in delegation, whether the hole is in your understanding of finance doesn't make a difference.

You're going to get to whatever the next level is. you're going to need to understand, you know, think of it as an mini MBA. All those things, not just from a textbook standpoint, but the practical use of what those things mean and how you apply them in business. And there's no better way to learn than, baptism under fire.

So if you're prepared gonna be happy you took the time to do it. And we're starting again with basics, but I can't predict what's going to happen to a founder who, who's going to get to $100 million. I've, not built a $100 million business. I know there's gonna be challenges.

But I think you're gonna have a very difficult time [00:34:00] getting even close to that if you don't have the fundamentals done.

PaySile Origin Story

Jeffrey Feldberg: And as we talk about that, Jim, let's now merge all the different worlds because you're not in a silo. You have had different exits, and you're an author, and you're helping other founders out there, but you're also doing PaySile. And to bring all those together, so for starters, why don't you share with Deep Wealth Nation, let's give PaySile a plug.

So what is PaySile? Why would I wanna know about that? And if I'm doing some kind of payment processing, which I am, most businesses

Jim Fitzgerald: Sure, sure

Jeffrey Feldberg: Why you guys? And then the follow-up that I'll just throw out there to, to get to is when you tell us about PaySile, what's going on with it, what have you done with PaySile in terms of how it operates, the strategies, what it does, that's been influenced by what we've been talking about in The Million Dollar Hurdle with your exits, with your founder journey?

Jim Fitzgerald: I think I've got a good story that'll dovetail nicely. So when I owned Taradel we were paying somewhere in the neighborhood of [00:35:00] $750,000 a year in credit card fees. And I just assumed that was the cost of doing business. We were an e-commerce business, and if we wanted somebody to pay us with a credit card, there was a cost associated with that.

The acquiring company, w- private equity-backed acquiring company was very much aware of that, and in their defense, smartly realized that's something that wasn't necessarily fixed. So they had developed a way of communicating with their customers on the benefits of using ACH versus credit card, which is a fraction of the credit card fees, and giving them the option to do that or pay the fee. And there was this, let's say, significant post-sale significant transfer of those costs went back into the coffers of the buyer. And here's why this is important, and I'll get to PaySile in just a second, I promise. But here's why this is important. This is one more reason when you're looking at the value of your business, think of [00:36:00] $750,000 times the multiple that we could have been putting in our pocket or in the EBITDA line, right?

And suddenly it's a significant number, okay? that's one tidbit, but now let's kinda transition that over to PaySile. 

Reconciliation And AI Edge

Jim Fitzgerald: PaySile, we've created a payment platform payment processing. We do credit cards and ACH and all that stuff, and there's... that's red ocean. There's a bunch of people in that business.

the way we've separated ourselves is the pain that happens after the payment, which is the reconciliation. So we've built through a machine learning model and incorporating AI we've built a way to automate most of the reconciliation that humans are doing now, and it is a laborious task and takes forever.

It delays close and is just something that if you ask... Depending on the business, some businesses are very simple, but if there's any complications involved, if you've got multiple line items on an invoice I guarantee you, [00:37:00] you probably have reconciliation issues. so we take that pain away, and also provide things like cost recovery programs and partner fees and things where suddenly now that burden isn't necessarily on the business.

We can pass some of it back to the buyer and also give the buyer an option to do it at no transaction cost by utilizing things like ACH. So we've kind of wrapped a bow around that and created a platform that makes it easy for businesses. In certain verticals- it's very powerful. Things like property management trades, HVAC.

And then we also have come up with ways to expedite how the money gets into your account. there's a lot of things going on there, but that's... Our, our biggest differentiator is the ability to reconcile automatically quickly and cleanly so there's very little human intervention to get these things resolved

Jeffrey Feldberg: And if we're open and honest about that, $750,000 a year in your particular case, I mean, that is not [00:38:00] a rounding error. That is just not a

Jim Fitzgerald: It's real money.

Jeffrey Feldberg: That, that is real money. And forget the enterprise value of a company. Over 10 years, if my math is correct, that's, $8 million a year 

Jim Fitzgerald: that could have been exactly right. that's not just the multiplier that I missed, that's the money that we could have been taking out of the business all 

Jeffrey Feldberg: That's right. Yeah 

Jim Fitzgerald: And let's go back a little bit earlier in the discussion when I talked about focus on the things you don't know.

There's a perfect example. I really wasn't aware. I didn't think the customer base would tolerate it, so I really never pursued it. And suddenly I think a lot of your listeners and probably... I think they're nodding their head saying you see it everywhere now. It's hard to make a purchase without having the opportunity to pay for the credit card fee.

as businesses, I think most of us have successfully shifted that back to the buyer. that's just a single incident, but I think speaks to what we were talking about earlier, is there's so much to know, and as you [00:39:00] grow, these things take on a life of their own and sometimes can be very significant, and you're just unaware

Jeffrey Feldberg: Yeah. And so we fast-forward to today with everything that you've seen and done and the various exits that you've been involved with, with Paycell. What would be my takeaway with Paycell of what you and the team are doing?

Jim Fitzgerald: Yeah. 

Embedded Finance Upside

Jim Fitzgerald: So we started the business about a year ago. We're onboarding our first clients here in the next 90 days. And that's an exciting time. we have people that have, you know, nodded their head in the right direction and decided to move forward with us. And we think that Our platform is set up to take advantage of something else that's going on in verticalizing payments, and the hot term right now is embedded finance.

So if you think of property management, let's say. So sure, you give folks the option to pay their rent, but 20% of the people in the United States [00:40:00] finance their rent every month,

And now there's the option to provide the financing to do that. When was the last time you shopped your renter's insurance?

Well, there's an option to do that. Did you know that for a fee you can have your rent payments sent to the three credit bureaus since it's probably the most significant payment you make every month to build your credit rating and your FICO score? All these things were revealed, and these are isolated incidents, but I'm just showing them to give the audience an idea of what we're talking about.

So all those things we can embed into the payment process. And depending on the arrangement, whether we're working with a SaaS provider or a large entity you know, there's revenue share models, so they get to participate in the upside of that while providing their users, a better experience

Jeffrey Feldberg: Okay. And so Deep Wealth Nation, think about that. Where's your business? Again, as we'll get to the end of the interview, we're not there yet, a little ways to go, but is [00:41:00] there's opportunity there, you, the team, your company, speak with Jim and team of how Paycell might be able to help you. 

Favorite Principle Branding

Jeffrey Feldberg: And so circling back to the million-dollar hurdle, a bit of an unfair question, I'll ask it anyways.

Jim, from the 16 different strategies, principles that you put out there, is there a favorite one? And I say it's unfair because it's like asking a parent, "Hey, which is your favorite child?" And maybe you have an answer. Most parents don't. But does one stand out for you of all the 16? Is there one that's more prevalent for you than the others, one that you prefer?

Jim Fitzgerald: there is. I wanna focus again now on this, the book was designed for smaller businesses. And I think the thing that I enjoy the most and I get the most feedback from is what I call the credibility and branding side. And I encourage the reader to act bigger than they are.

And what does that mean? And the example I give, which is a real example of somebody we had come out to pave the driveway. And one guy, showed up [00:42:00] with a stained T-shirt, smoking a cigarette with some mustard stains. And he looked up and down the driveway and said I don't know, 1,000 bucks."

And, a couple hours later, a guy came up in a truck that had been what's the term where they put the uh, decals across the entire 

truck, fully branded with the polo shirt, with the logo on the polo shirt, and a clipboard, and very politely asked how my day was going, and said, "Would you mind taking a walk with me up and down the driveway?"

And he was like, "$1,400." Well, who do you think we went with?

Jeffrey Feldberg: Interesting. 

Jim Fitzgerald: okay, that's a simple example, but just how incredibly powerful that is and it encompasses a couple of things, a lot of folks don't understand what brand is. But brand is, the feeling somebody has when they're doing business with you.

It's not necessarily your logo, and I think people get lost there. It's how when those two people left, how did I feel about those two companies? They both had a brand, by the way. Just like they both have-- I'm sure they both have a culture, like I said earlier. [00:43:00] But yeah that's powerful, and I think very often ignored.

I think sometimes people say, "Hey, you know, I, paid a good designer. We have a nice logo." I don't know more than that.

Jeffrey Feldberg: yeah, no, interesting, and how you were willing to pay, in this case, a 40% premium just for that peace of mind. You could have gone the cheaper route, but who am I really getting into business with, and what's that experience? So it's interesting. I've never shared this story on the podcast before. You actually brought me back memory lane.

So in my e-learning days with the company Embanet, we were really the golden child of the industry, but I didn't know any better. It was my first company, and for most of our customers, they never realized how large we were. And one day I'll remember a customer said, "Jeffrey, I thought we were your only customer.

I just was speaking to someone, and they said, 'You're a customer.' And then I s-," they were at a trade show. "I was speaking to someone else, they said you're a... My goodness, how many customers do you have? I thought we were the only one." But that's not the story. We worked with schools, and we had [00:44:00] this one particular private college that was across the country, to be nameless, and we'll keep the name for privacy out of the story.

They ended up dropping us as their solution to go with our competitor, who was an, an inferior second choice and more expensive because in their mind, they asked one question. We had taken them from nothing, so from zero e-learning revenue, and the contract was coming up. It was now a multimillion-dollar contract.

And Jim, to your point, in their mind, they said, "Okay, do we go with Jeffrey and Waleuska at Embanet, the mom-and-pop show, or do we go with this corporate entity who is all professionals, and they've got some private equity behind them, and they're all corporate?" And we know how that story went. Similar to yours, it was a hard lesson for me to learn, but an important one.

And after that, everything changed. We became more open, [00:45:00] and it wasn't just our office. We would do press releases now at our world headquarters, and we projected strength, and we projected who we were, and without naming our customers, how big we were. Sometimes even the liberty of maybe going a little bit beyond 

that, 

as you, you often 

Jim Fitzgerald: it's crazy. Yeah. It's as simple as I remember when I started Taradal I did back then DVDs promotions. and it was basically me talking about the business, and I kept saying we and I remember my friends watching it and laughing, saying, "Who's we?"

Jeffrey Feldberg: Exactly. as founders, 

we've we've all been there. Yeah.

Jim Fitzgerald: Yeah. It's important

Jeffrey Feldberg: Yeah, absolutely. 

Trust Your Gut AI

Jeffrey Feldberg: Listen, we're about to go into wrap up mode. Before we do go into wrap up mode, I have one question. It's actually a question within a question. Is there an important question that you and I haven't covered yet? Maybe it's a theme or it's a topic that you wanna share with Deep Wealth Nation, and then from there we'll go into wrap up mode

Jim Fitzgerald: I think we covered a lot. I think if [00:46:00] there's one question that I get, again, and I just want to reinforce something we've already said. It's trust your gut. That's like my favorite thing in the world. Trust your gut and make a decision and get a data point.

Reinforce that and also know that everyone goes through these phases as they grow their business and develop. And understand what you know and understand what you don't know and catch up on what you don't know. You'll be glad you did. And there's so much available to help you with that now, especially with Claude and ChatGPT and Grok and 

Jeffrey Feldberg: Oh my goodness, AI. absolutely. And we didn't talk about AI, but quickly, thoughts about AI very quickly, high level, what you'd want us to know?

Jim Fitzgerald: I think I don't think you need to become a vibe coder, but I do think it's important to look at AI beyond a glorified search engine and really understand what's going on with it and how it can be leveraged. [00:47:00] And even if you did invest a little bit of time building a, a simple application...

I had a teacher in high school that had a phrase, and he s- something along the lines of, "Knowledge without comprehension is a dangerous thing." And, I'm so old that when I first started using a computer, it was DOS. But when we went to Windows, I knew what clicking on that button was doing behind the scenes.

And I think... And I'm not an engineer, I'm not a developer, but I've worked with a bunch of them, and that kind of comprehension has helped me. So I think really understanding what's going on to the extent you can, it's moving very fast, but understanding AI and what it can do, and spending some time with it every day you won't be disappointed

Jeffrey Feldberg: Absolutely. At least having the confidence, yeah, I may not be a coder, but I do know what's going on. I can have a conversation level. I'm not gonna have the wool pulled over my eyes, or maybe I'll see something that I can put into the business. Great advice. 

Back To The Future Advice

Jeffrey Feldberg: So that said, speaking of advice, we're going into wrap up mode.

It's [00:48:00] our tradition here on The Deep Wealth Podcast where every one of our guests, I have the privilege and the honor to ask the same question. It's a fun question. Let me set this up for you. When you think of the movie Back to the Future, you have that magical DeLorean car that will take you to any point in time.

So Jim, this is the fun part. You look outside your window, it's tomorrow morning. Not only is the DeLorean car curbside, the door is open and it's waiting for you to hop on in, which you do, and you're now gonna go to any point in time. Jim, as a young child, a teenager, whatever point in time it would be, what would you tell your younger self in terms of life lessons or life wisdom or, hey Jim, do this, but don't do that?

What would that sound like?

Jim Fitzgerald: Oh boy, I could spend the afternoon on that. But I think the one... From a business standpoint, the one thing that I learned the painful way, but I'm fortunate I did learn, was we already had a differentiation in our customer base before I sold Taradel. But the one thing we didn't have that we fixed [00:49:00] was recurring revenue.

So if you're looking at your business, do whatever you can to come up with a way to get your, the recency, frequency, and monetary value of your customers to turn over more often, and you won't be disappointed. It's a it's great for you, it's great for your customers, and incredibly great for your valuation

Jeffrey Feldberg: Absolutely love that. You know, You're taking me to step three, future buyer, not necessarily your investor or your buyer, but your customers. We have this ladder, and one is just the pay-as-you-go, then you have the recurring revenue, and then the last one is actually profit sharing, revenue sharing. The tougher the problem, the bigger the problem, the higher up the ladder that you can go with business models.

And so yes, hope is not a business model. Get a really good business model, recurring revenue as a minimum, if not beyond that. Absolutely love that. 

Where To Find Jim

Jeffrey Feldberg: And so for someone in Deep Wealth Nation, they have a question, whether it's about the million-dollar hurdle or beyond that, [00:50:00] or having you and the team help them with their payment, their processing, where would be the best place online to find you?

Jim Fitzgerald: Best place to find me I would say as we've talked about it a good deal today, so from a memory standpoint, I would go to milliondollarhurdle.com

Jeffrey Feldberg: Terrific. MillionDollarRule.com and Deep Wealth Nation, great news. It doesn't get any easier. Go to the show notes. It's all in there for you. So Jim, that said, congratulations. It's official. This is a wrap, and as we love to say here at Deep Wealth, may you continue to thrive and prosper while you remain healthy and safe.

Thank you so much

Jim Fitzgerald: Thank you

Subscribe And Final Thanks

Jeffrey Feldberg: So there you have it, Deep Wealth Nation. 

What did you think? 

So with all that said and as we wrap it up, I have another question for you.

Actually, it's more of a personal favor. 

Did you find this episode helpful? 

Have you found other episodes of the Deep Wealth Podcast empowering and a game changer for your journey? 

And if you said yes, and I really hope you did, I have a small but really meaningful way that you can actually help us out and keep these episodes coming to you.

Are you ready for it? 

The dramatic pause. I'll just wait a [00:51:00] moment. Drumroll, please. Subscribe. Please subscribe to the Deep Wealth podcast on your favorite podcast channel. When you subscribe to the Deep Wealth Podcast, you're saving yourself time. Every episode automatically comes to you, and I want you to know that we meticulously craft Every one of our episodes to have impactful strategies, stories, expert insights that are designed to help you grow your profits, increase the value of your business, and yes, even optimize your post exit life and your life right now, whatever you want that to look like.

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So all that said. Thank you so much for listening. And remember your wealth isn't just about the money in the bank. It's about the depth of your journey and the impact that you're creating. So let's continue this journey together. And from the bottom of my heart, thank you so much for listening to this episode.

And as we love to say here at Deep Wealth, may you continue to thrive and prosper while you remain healthy and safe. 

Thank you so much. 

God bless.