Serial Entrepreneurship: Navigating the Risks and Rewards - podcast episode cover

Serial Entrepreneurship: Navigating the Risks and Rewards

May 25, 202439 minEp. 23
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Episode description

Guest:

Jeremy Lessaris
Serial Entrepreneur | Founder & CEO, Payment Brokers

Host:

Melissa Aarskaug

Executive Connect | Website
YouTube: @ExecutiveConnect

Episode Overview:

In this episode of Executive Connect, host Melissa Aarskaug speaks with Jeremy Lessaris, a seasoned serial entrepreneur who has built and sold eight companies across different industries. Jeremy dives into the realities of entrepreneurship—from the wins to the wipeouts—offering candid insights into the evolution of payments tech, the growing influence of AI, and the art of scaling a business sustainably. Whether you're in the early stages or planning your next exit, this episode offers practical guidance on staying ahead without burning out.

Timestamps:

00:00 – Introduction
05:30 – The Evolution of Payments Technology
09:03 – Impact of AI and Machine Learning
19:33 – Strategies for Scaling Businesses
20:36 – Mentorship and Networking
27:35 – Balancing Work and Personal Life

Connect With Us:

Podcast Website: https://www.executiveconnectpodcast.com
YouTube: https://www.youtube.com/@ExecutiveConnect

Social:

LinkedIn: https://www.linkedin.com/in/melissa-aarskaug/
TikTok: https://www.tiktok.com/@melissa_aarskaug
X: https://x.com/melissaaarskaug

Transcript

Intro / Opening

I challenge every small business owner. If they take credit cards, they should take their statement out. They should take the total of fees and divide it by their revenue and find out what percent they're paying. And if they're paying above 2.3, 2.29, 2.2, they need to really look into it because I have seen companies that are paying 6%. There is absolutely no need for that. [MUSIC] Welcome to the Executive Connect podcast, a show for the new generation of leaders.

Join Melissa R. Skog as she speaks to a wide variety of guests that bring new insights into leadership, prosperity, and personal growth. While knowing has all the answers, by building a community of open-minded and engaged leaders, we hope to give you the tools you need to help you find your own path to success. [MUSIC] Welcome to the Executive Connect podcast. I'm excited to have Jeremy with SARS here with us today. Jeremy, let's jump right in.

Can you give us an overview of your journey into Fintech, SAS, and leading eight successful exits? >> Absolutely. Well, first of all, great to hang out with you today. My background is really, really simple. I'm a serial entrepreneur, built and sold some companies along the way, had a good career in marketing communications, was a vice president of a big company. Husband and really now, I'm just on a journey to start to have some balance.

So it's really more about the balance and less about the work. Still operating companies, still building things. I'm love ideating new things, not a great operator, so I like to build them, get them to go point and hand them off to those who are really good at operating. And that's been my journey. My journey has been a lot of from one business to another and extremely diverse markets, filling in the blinks as I saw them.

So if you look at my first company, it was really, I had moved out on my own, I had no furniture, and I wanted to get into the furniture business because I could buy furniture cheap because I found a wholesaler. So from that all the way into FinTech, all of those little companies that I built and sold were really filling in the gaps where I found ideas or things that I could help myself in my business with. It started with e-commerce, and so I was starting to learn how to develop and build tech.

And I did it kind of bootstrapped, so I stayed on that path until I had my career. And then as I got into having a career and building side hustle businesses, I was able to accelerate to financing myself until I started really getting into bigger companies where I did raise a little bit of capital for a couple of them, but not a ton. But it all successful for me in terms of learning what worked for me until I learned that I wasn't a great operator.

I think I have what I call squirrel moments where I'm like, "Oh, look at this, I want to go do this." And then I find another gap, like somebody should do that. No one's ever done this before. I'm looking, there's no solution, so maybe I can fill the gap.

So it's been a journey of doing those things, and as I learned who I am and where I fit and where I'm most successful, I was able to continue down that path to build better, faster, stronger, and more in alignment with how I wanted my life to be. So now it's more about balance, and I've been trying to build things that really improve my life. But take over my life. It was, you know, early on it was more about building things to survive. I came from that kind of survivalist mentality.

I moved out at a really young age and having done that and kind of had some hardships early on, that was really just about money. Like I built things for profit-sake. And then as I grew up and started making better choices and decisions about how I was building things, it was more thoughtful about how is it going to be? How is it going to impact me? How is it going to impact my day to day? What does my work life look like?

And some of that came from my wife more recently in the last, you know, seven years of just understanding where the balance needs to be in terms of having work and life. And because of that now I'm building enterprises around how my lifestyle should be and what I can do to impact versus profit. So it's really, that's been my journey from, from kind of hardship to now more impact and how I can impact others.

And so my more recent ventures, not necessarily focused on passion where I think everyone tries to drive towards that. I was more driven towards how can I impact others? Because now I'm in a position to do that. And how can I do that in a way that doesn't destroy my life and make it a 18 hour day, seven days a week, you know, stuck behind a desk? So that's really been my journey. I identify with what she said, squirrel moments. The goal is in the squirrel moments I find.

So I first nugget of our podcast here, scrolling is okay. Scrolling is okay. And you know, kind of what you were talking about a bit, Fintech, Technology, SAS. It has changed a lot with AI and new ways of doing business.

The Evolution of Payments Technology

How do you think technology is changing the payments landscape? Wow, that's a big one. I think payments have become awesome. Like, you know, how it used to be to make a payment to secure your money to, you know, transact overseas. Like all of that has become seamless. I can walk into a store and almost walk out with the product without ever having even talk to anyone. So I think the payments landscape has made us, made buying things so much easier. And that's great for the company side.

It's also great for the consumer side where I've seen kind of a really bad light in payments has been how sticky it has become and how predatory that landscape has become on the small to medium size company. So I actually started a company in this space and over the last couple of years, which is just looking at the cost of payments. And we actually utilize, I'm going to say machine learning.

It's not AI, but we use a machine learning tool to look at the cost for trying to make transactions for credit card processing. And we utilize that data to identify how much profit is being, you know, taken from these companies. And we found in a study that we put together, $50 billion a year in just the US. And I would say 80% of that burden falls on small to medium companies. The companies that can't afford to spend it have the heaviest burden.

So we built a tool to effectively identify and utilize that data to negotiate with their existing vendors so they don't have to make changes to their operational systems or POS systems or terminals or by new equipment or set up new accounts. It's such a headache and it's so impactful to the company. But we found ways to put money back to their bottom line without them making any changes.

So that's been a big focus for me because I see how heavy handed some of these processors can be the guys who need it the most, right? The small pizza place, your dry cleaner, the place you get a massage, I mean all of these little businesses, they're carrying sometimes 5 or 6% to just transact money. And it's almost predatory. I mean, I hate to say that because I'm sure there's going to be a season to assist at some point.

But I would tell you that it has been part of my new journey to help small to medium-sized companies because it impacted me so heavily early on. In my furniture company, when I was really young, I owned a company called furniturestock.com, chargebacks made a huge impact on me, almost put me out of business before I sold the company. As I started growing up into more tech-focused organizations, it was always determined as high risk. So I always paid a high risk fee.

So it was like really difficult early on for me. Now that payments are secure and seamless and it makes it very effortless to go through a checkout process like you can go online and buy anything in two seconds now. It's great. That used to be like a seven-page step-by-step thing. There's value to that. There's value in security, there's value in the technology. But I also see that they're over-valuing that technology. And if you're a big company, you have a lot of leverage.

So the big companies don't pay what the little companies pay. The little companies pay way more. And in some cases, I've seen six, seven, even eight, nine, ten percent, just a transacted credit card. It's just not right.

Impact of AI and Machine Learning

So it's been a new journey for me to focus on that company I started called Payment Brokers, which is purely that. We use AI and ML to negotiate rates and fees using data. So it's a fun product. It's also putting money back to people's bottom lines. I hate to even call it a sale. It's the easiest thing I've ever done to help a company. So that's been my journey with that. I think in general, AI is such a unique thing.

I'm actually in the midst of writing an article about where I think AI is going to go and how it's going to impact handcrafted, hand-processed, human interference things. Because I think there's going to be a much bigger effort and more value placed on things that are done by hand. And not everything AI. So I think the craft business may really see a really unique boost because of this. And so I'm really focused on that.

I love handmade the stories, the humanality of a company and not necessarily like, yeah, our CEOs of robot and all of this is done by machine and all this is pre-programmed. And we've been following you around using AI. And I know everything you're going to do before you do it and predictive ordering and like, I don't know if I like that world. I think I much rather like actually talk to people and shake hands and actually interact with humans.

So I think there's going to be a bigger value placed on things that are done manually. And more from a luxury branded perspective, that's going to change everything. I don't know that I want an AI designed house. Everything was built and machined by AI and everything is AI. So I feel like that's going to be a little bit of a resurgence of kind of a second renaissance of craft. Yeah, absolutely.

As you were talking about how easy it is to use payments, I kept thinking about when I'm writing trains in Europe, how easy it is to use my Apple Pay to scan in and Bob and Bob have to go up to the machine and buy a ticket and put a credit card in and enter my pin and that whole process is gone. It's seamless now to get on a train and off a train and I laugh because as a woman, I used to be one of those big bag women that carried all my cards and all my things and all, you know, a giant wallet.

I don't have a wallet anymore, right? I don't have to use a wallet anymore. So it makes lugging around cards and things so much easier to like human should transact and do businesses. So I do love the ease of that at times I'm a little concerned cyber from a cyber security and security perspective.

You know, I do have some concerns on how they're used now, but I think it is so much easier now and to use, you know, Apple Pay and other methods of payment and people want to take out money from an ATM now, they could charge anywhere from $2 to, you know, like you said, it's $6,9% to get $20. So if you need $20, they're charging you $9, you know, these businesses, some of them are keeping some of that money if they're larger organizations, right?

And others are giving it back to other organizations. So I do see that from my side and in my industry as well. But I mean, you see it every day. I mean, you go to a restaurant now and there's a 3% service fee and you're like, what's that? Well, if you pay cash, we don't charge you the 3%. Okay. So I want my rewards, I want my miles, I want all my stuff, right? I'm just going to pay it.

So we have immediately hyperinflated the market because everybody said, well, I think it's like 3% that we're being charged. So we're just going to pass it on to our, pass it on to the consumer, which you're going to do anyway, right? Whether it's baked into the price or whether it's, you know, on a fee, it's going to happen. And so everybody targeted Visa and Mastercard and American Expressor, like these are the bad guys. So they went after them.

And there's a bunch of legislation that they're really attempting to pass right now. There was a recent settlement for billions of dollars in potential fees that they're going to reduce. And then a week later, they raised the pricing. So I mean, it's unfortunate that we're targeting them when the problem isn't really Visa Mastercard. It's the technology company that layers over the top.

It's the processor and then the reseller who sold the processing and the reseller of the rese-- I mean, there's so many layers of people now touching the customer. There's transaction and the transaction fees have gotten out of hand. And there are even companies who know they're doing it. And I have, you know, emails from them saying, we don't care. We're, it's, we're a sticky solution. It's like, that's not really free market choice.

And I get it, you know, if you provide a tremendous value and there are companies that do, you know, there's a really well-known service industry software that everybody uses. And they, they partnered with a processor and they're like, you have to use our processing. You cannot use a third party. And they just charge whatever they want. And because their software is so good and it's kind of an industry standard, they know they can get away with it. So they can charge 3%, 4%.

No one's paying attention to it because it's the cost of doing business. But it's like hyper inflating the market immediately. And so now Visa Mastercard came back and said, you know what, we're going to, not only help you do this, we're going to help you push that right before they fought it. They were like, we don't agree with you charging customers this fee to what's called cash discounting. And so if you pay cash, then they're going to lose business, right? So they didn't like that idea.

But they do like the idea of, hey, why don't we just charge your customer directly the 4% here and lies the major problem. And there's no controls like they can just charge whatever they want. And there's really the merchants like, why have to take credit cards? So I feel like there's going to be a big shake up at some point. I'm targeting this $50 billion reduction. And again, that's mostly on small to medium business.

But in the interim, people just need to be more aware and like, take out your statement and your credit card processing statement and look at it. That's a first, you know, pass. The second piece is like, the more this gets technologically integrated, the harder it's going to be down plug from it. Like you just said, it's so easy to just tap. What a great way to get impulse buys. Like I've done it and went, oh man, did I just do that? Right? It's so easy to pay now. And there's no more cash.

I mean, and it costs money to get cash out. Like what you were just saying, there's a game around ATMs. Like, hey, we're going to charge you a flat $6. So what would you do? Take out more cash. Well, we're going to cap. You can only take out a hundred bucks. So like no matter what, they're getting 6%. Right? It's crazy. So it's bad, but it's also like, okay, there is a convenience part of this. Even banks now like to deposit cash, they charge you.

So even if you're a business and you're like, I'll take a bunch of cash, don't forget you got to get brings. They got to come pick up all that cash. They got it cost money to move that money. They're security involved in it. You can have an employee take it and not show up to the bank. I mean, so there's all these like weird oddities with this. And I feel like at some point, there's going to be some leap frog technology.

I know everybody pushed a lot of eggs in the baskets for cryptocurrencies, which I'm not an advocate for at all. But I would say there's going to be some point where this just is not going to work. And I feel like the consumer is going to drive that, the merchants are going to drive that. Meanwhile, like Visa, MasterCarder, they're posting record numbers, absolute record profits. So I don't think that's going to change anytime soon. Now, I like my 2%, 2.5% cash back. I like my rewards.

I like going on trips for the spend that I normally have anyway. I wouldn't give that up. So it's a hard unplug. That's for sure. Yeah. And I think that's the other thing you made another good point is, are people actually looking at their statements? Are they looking at so convenient now to take the money out when you're somewhere to Amazon things? There's so much happening regularly in a month for people that are buying things.

And that's partially why Visa is posting some of the profits, right? People want things now today and they're willing to pay for it. They don't want to wait for shipping. They don't want to wait. They want it today now. And that is the world we live in. They want to have their products. They want to be the perfect way. They want it now today. No, they don't want to work out. Immediate gratification. Immediate gratification, that's dope. Yeah. Yeah, you push a button.

There's a comedian that talks about, you order a pen and you're like, I just want to ship one pen. You know, prime now it shows up today. You're like, that's amazing. Right. You're a little excessive. A little excessive? Yeah. A little excessive, but the convenience you pay for it. And it's unfortunate. I don't think businesses even look at their statements. Even the consumers aren't doing it, businesses aren't doing it either, they just chalk it up to the cost of doing business.

But then you ask why all of these small and medium-sized companies fail. They're just not paying attention. They're just thinking about it. That's a good point. And that's one another good takeaway for the listeners. Check your statements and look at what you're actually spending money on because I think you'll be shocked as we all are. There's things on there you may not have purchased or you maybe went out to dinner and the bill is $50, but it's $150 bucks on your statement.

So call the restaurant, get it reversed, it's an error. I want to put it a little bit. Here's a tip, I'll just give you this. I think it's an important one. So you're talking about your credit card statements. And for small business, I challenge every small business owner. If they take credit cards, they should take their statement out. They should take the total of fees and divide it by their revenue and find out what percent they're paying.

And if they're paying above 2.3, 2.29, 2.2, they need to really look into it. Because I have seen companies that are paying 6%, there is absolutely no need for that. I mean, it's crazy that they have silent partnerships. Anyway, it didn't mean to interrupt. No, no, no, definitely. That's a really good point. I'm glad you run it up. I want to ask a question. I know 8 successful exits is a really big deal. And I think that is a true testament to you as a leader, as a visionary.

Strategies for Scaling Businesses

One of the questions I want to get your perspective on is how do you grow? When scale these businesses, do you have any tips, strategies that you can share with our listeners on how you are able to do that? So I always pause when we talk about 8 exits to clarify what 8 exits looks like. Because everyone goes, wow, that's so glamorous. And you did all these, you know, so all these huge companies. First of all, that's not the case. Some of them were out of necessity.

Some of them were absolutely on its last leg. Having hemorrhaging money had no idea how it was going to prop it up and I was fortunate enough to learn the M&A side of exiting and was able to find operators that took over and took the home. So there have been some really great exits. So I'm not discounting the good ones, but there are some bad ones too. Ones that I'm not super proud of. And then I've had some micro exits. Things where I'm like, I built it.

I don't know what to do with it or how to operate it. And other companies saw much bigger value in it and took it way further than me. For the ones that I built and scaled, I had amazing mentors.

Mentorship and Networking

So I would say if I would had to start over and do it all over again and I didn't have those, that would be the first thing I would invest in. Would be some kind of mentorship, some kind of advisory, some kind of outside influence help because there was no way I could have done half of the things I did without the mentors I had.

My former bosses in my career, working at a very large manufacturing group, the CEO of that company was absolutely pivotal in my success and a lot of the things I did from a growth side. I had another mentor who was extremely balanced and had a balanced life and was mentoring me not to be an idiot along the way. And you know, fiscal responsibility, which apparently I just, I didn't get the memo early on.

So I think in general scaling requires all focus on only growth and I feel like what ends up happening is these small companies get diverted in a billion directions and they don't look at what's the most important thing, which typically is sales, sales cures all things. So long as it's profitable. And I feel like everybody's like, our logo has to be perfect and this has to be right and it's like too much focus on things that don't make impact.

And so scale for me fortunately was all focus on sales and I'll fix everything else, you know, it was like jumping off the cliff and we'll be able to play on the way down. And we did that with sales first and then we were like, let's fix all of the things as we go to this path. And that was successful for some of them, not all of them.

The second was not and this is just for me, so I don't recommend this for everyone, but bootstrapping changes everything when it's your money and you work 40 hours a week to invest in it. The way you invest is very different than if you, your first start up, you go raise a bunch of money because it's not as important to you when it's your own.

So if you start by bootstrapping, everything else gets much, much more clear on what should be focused on first because you're trying to get to profitability. And that's the last piece for me was I was fortunate to not have to bleed my startups because that had an income. I was the king of side hustle. So I had a normal career while I built many of these companies and my career afforded me the opportunity to not have to take blood from a rock.

There's not money there to take and I feel like startups often take, take, take, take, they're like the second money comes in, they're like, I need a new car. So they end up hurting the money, the money is that needed to be reinvested in these startups. Don't get back there because they're like, hey, it's starting to make money. Great. I'll start taking that out.

So those are some things that helped my early stage growth growth beyond that was purely networking, being around the right people, luckily at the right time in some cases and continuing the growth path by focusing on sales, sales, sales, sales. If I could get more sales, I could cure some of the problems along the way and I did it more recently from the bottom up. Now when you have the ability to pause and do things more thoughtful, you grow profit, not revenue.

And so more recently, everything I focus on is how do I grow profit up, not top line down. So when you're like in the bootstrap, I'm just trying to make things work. Everybody starts revenue because it's the only thing you have. When you have a little bit more time and can be patient about growth and you grow profit first, it's a game changer for longevity of the company, stability of the company.

And I think in general growth becomes really easy because people recognize when you're hungry to grow, right? You can smell it from mile away. When you're not, the indifference makes a difference to the client, the customer and everything around you. So when you have that kind of passion and desire to grow things profitably, people can see it. And I feel like it definitely makes an impact long term for the business. Yeah, I love to hear that as a revenue driver, sales professional.

I would absolutely agree. There's always going to be flashy things to spend money on, a bright new office and you know, fancy pens and all these things. But I think I absolutely agree with what you said. You said it's focusing on the revenue driving sales. And then the other thing just to touch on that I love you said is focusing on what matters, right? There's so many pulls of all of our time.

You know, I think it's really focusing on the business and what needs to happen today that's driving the revenue is really key. And then one other thing that I love is you're such an entrepreneur. I love the spirit you have that drives you forward to these businesses because they're all so different.

So can you talk a little bit about like what is that drive for you and how has it, like, maybe the question is, talk to me about your entrepreneur going from W2 employee to an entrepreneur and what's driving that for you? So my father started it really young and he was a serial entrepreneur. So growing up, I watched him build car wash, I watched him build a detailed shop and all these little businesses. And so I just saw it early on. I jokingly, and I wrote an article about this.

It was more about my father from an early age. I was in a stroller at like prepaid legal services, multi-level marketing. I was literally a baby going to MLM meetings. My parents were like, really, they got indoctrinated really, really like, AMOA global. I was a baby. So I think I grew up this like thinking grow rich was a book I heard about when I was like three.

So growing up, I was always around like, hey, we're going to do this or we're going to start this detailed shop or we're going to do this thing. So I saw them do it. And then at six, I started this lemonade stand. I wrote a huge article about this. I love it. Kind of my claim to fame was I started this lemonade stand. My father was like, I wanted these like this, I don't know what you'd call them, but they're like building blocks, but they're life size. So I built a lemonade stand.

My father borrowed me money showed me how to like account for it and I owed him interest. And that lemonade stand netted me thousands of dollars that year, over a summer. And to me, it was like my first taste of entrepreneur and being an entrepreneur and from that point forward, it was on. So like I took that money invested in arcade game, which I thought everybody's going to put coins in it. So I'll still only arcade, but I'll have this other income. No kids put any money in except me.

And if it was a failure. So I got my first taste of success and failure like back to back in one summer. And that point for it, it was just a journey of what I thought I wanted to be.

Balancing Work and Personal Life

I was always focused on money. It was a survivalist mentality. I lived in a car. There was a lot of hardship to try to like balance out with let me go make money. I'm going to be this multi million dollar international businessman entrepreneur like that was a vision when I was like six. So from that day forward, I think it was just about that vision. And as I chased it and started to get to those things, I recognized that's not what I really wanted at all.

And it wasn't until I had a mentor who brought some balance. A former business associate, and his name is Eddie Booth, lived in or lives in England. And was a customer of mine who like took a liking to me because I was a really young running a business and he was a customer and he was like, I see an absolute train wreck if I don't step in because I was just trying to make it work. I was propping everything up and I had, you know, living on my own really young, just trying to make ends meet.

And he kind of gave me this different path, which was more thoughtful, more focused on why I'm doing it and not what I was doing. So I took a little bit of that. I didn't take a full dose, if you will. And I started incorporating that into my life and it made big changes really quickly. And so I went from these little tiny, crazy idea entrepreneur things to, I need some stability first and then I'll side hustle my way through it, which was kind of what I was told to do.

I mean, he said, go get a good job. You're going to get a great job. People are going to recognize that you're talented. And I did. I got a really, really great job. And I took all of my side time and money and I would burn 20 hours a day, nine days a week. Like, there was no nights or weekends. It was just burned through idea after idea after idea and I loved it. It was a dicking to a point that like any addiction, it affects your life.

I lost friendships, relationships, you know, other things that like I didn't have a life outside of business. It became like, but it was a drug. It was my hobby. I was in, I only wanted to talk about business all the time. My friends were kind of like they're in a sports and all these other things like didn't care, didn't care at all. It wasn't even on my radar to like the fact that somebody could pull up stats and read somebody's baseball stats, I care less. Like, what is that doing for you?

And I just again focused on survival. It was just about making enough money to do the next thing, the next thing, but then too much is never enough. So you just keep growing and growing and along the way, you sacrifice everything. Literally everything. Health, friends, family, everything was secondary to me being successful. And then you get there and you go, I'm here by myself with nothing. Like I have everything, but I have nothing. Yeah, I, yes.

So that was the pivotal moment of, what did you just do? My health was failing, my teeth were bad, like my eyes were shot, my hands hurt from being on a computer, my back was art. All of the health things, all my friends had gone on about their lives together and built great friendships that I was never a part of and never showed up to anything. I was just focused on work. And so I had gotten there, made a bunch of money and now I'm like, all right, let's celebrate.

And then it was like, I've been seeing you in like two years. What do you mean? So then it became more about thoughtful growth and development of how I can do things better. And again, still focused on success, but just a little bit more balanced. And that, I think that's key is, is, you know, I want to zone in on some of the things you said. And, you know, I, I, I laughed that she said, the lemonade stand and the MLM, one of my first mentors was a diamond and amwin.

I used to be at eight and I would listen to his pitches and his meetings and he was a partner at a firm and he was like, Melissa, you got to listen, you got to learn. And so I thought it was only me that had the lemonade stand. He made me do one summer and, but the other thing that I wanted to touch on is, I used this word a lot when I speak in, you know, either talking about tech or leadership.

I think you nailed it on mindfulness and stepping back out of your own self no matter what your goal is, whether it's to build, you know, to, to build a business, to find a spouse, to raise good kids, stepping back and, and analyzing where you are. Am I living my best life? Is this in line with my values? I'm building a business, but my health is suffering. I have no friends.

So I think, you know, one key point is in, in, in to the listeners, a lot of you guys are executives, leaders, leading big teams doing big things, but how is your personal life? How is your health? Have you been to the doctor? Have you gotten that report card? And so really taking a step back, like you said, is really key in your journey, professionally and personally. So switching a little bit, you know, I think back again, eight exits. When is the right times to sell?

I know I have a lot of friends that have really big, really big businesses and they don't want to walk away or maybe really small businesses, but they've lost the passion for that business. Can you talk a little bit about when's the right time to sell or, and, and negotiate the sell and maybe, maybe what have you learned from selling eight? There's no right time. There's no, there's no formula for this that I have.

I mean, I, I think I knew when it was time for me, when my passion was gone completely, when the frustration was at a, at a point, and my distraction was so focused on something else already. And I think my number one telltale sign for me was, I had already moved on, but the company was still operating. And it was, by the way, people are going to go through pain. So I hate even telling people if it's not for you move on, like that's not always the case. You have to push through some of the pain.

So don't just jump because it's not what you want to do anymore. I mean, there are definitely valuation points in a business that you should recognize and just know where you're at. Knowing the value of a company is important because at some point, people build things not knowing what the end value is and then when it's time to sell, they, they just spent 10 years building something that's worth two years worth of revenue. And they're like, wait, what?

I thought this would be worth millions of dollars. It's like, it's not. Check the industry, understand what you're building and the valuation of what it's going to be at exit. But most people don't get into a business thinking about the end. So they're like, I'm going to build this thing up and it's going to make millions of dollars and then reality sets in that it's not.

And it's not exactly what they thought it was going to be because not enough people spend time researching upfront about all of those things. They just get into business, which is great. I actually think that's a better way to do it than research. What is it called? Analysis paralysis. You know, so knowing when to exit, I don't think there's a right answer. I think you will know when it's time or put it on the market and see what it's worth and get a general sense if you feel like it's time.

There are ways to do that through brokerage. There are ways to just do it on your own and, you know, kind of FSBO for sale by owner style marketplaces where you can put it out and just get a general sense of what you're dealing with. It's not easy to exit either. This is not something you do in a week. It takes months. There's a lot of transitional time.

You're kind of married to the business even for a period of time after you sell it unless the company is just so far advanced and can integrate better or they buying you to shut you down for some strategic reason. I mean, I think there's different reasons to exit, but most people, it's all about valuation. Yeah, I agree. 99% of the time it's just about, listen, I don't want to make $250,000 a year anymore. I'm done doing this. This thing's worth a couple million dollars.

Is that going to, you know, provide for you and hold you up and take taxes out where you left? Are you sure you're ready to exit? Is this where you want to be? Do you want to put an operator in place? There's other ways to exit a company without selling it. So I think in general, it's just trying to find what's right for the current ownership or operator. And then you put people in place and then you find out, this is actually makes sense to do. For me, it was like, I got a couple of them.

I had no choice. I was approached by an investor. They gave me a great offer. I had not yet recognized that I was a, not a bad operator. I'm just not built to operate companies. I'm a builder. Just like, you know, some people are builders and some people are homeowners. It's the same thing for me. I've identified early on that I'm not a good operator. And so when I found a good operator who was willing to value it at something that was valuable to me, then I was out. It made sense.

It goes with a lot of heartache for those. Very true. Very true. A couple last things before we close into be mindful of time. Just maybe some final two final questions. An area maybe that you're bullish on as far as technology. And then any advice, just your final thoughts on what you, are you bullish on and then any advice for people that are growing businesses in the spaces that you're in and that you want to leave the listeners with?

Bullish. I would say, I mean, look, AI is really a unique tool. And I feel like everybody's putting a lot of chips on the table, but these horses are racing and we don't know who's going to be the winner. So I'm not necessarily saying I'm not bullish, but I'm very cautious about putting any kind of chips on one horse. There's just too many. And things are happening at a almost unrealistic pace. And every day I see some new, you know, Gen AI coming out that I'm like, what is that? What?

That could put this one out of business and this could change this. So I think people have to take a step back a little bit and look at this more holistically as a tool. Use the tools, like get embedded, invest in them, put them in your business. Just don't prop your business up on them yet. They're moving too fast. They're too dynamic and they can shift overnight and drastically put these companies out of business.

So it's a weird position to be in with tech because I don't think we've, I've never seen a tech that's been like this. That wasn't speculative. Crypto a whole different discussion for another time, but I would say, I am really bullish on as a tool and people should leverage every bit of it. It's made me super efficient and a lot of things I do every day. I think people should use that crutch to the best of their ability. Just be careful on building a business around it.

So that's my bullish and my advice. I love it. That's great advice both. Thank you so much for being here, Jeremy. And thank you for sharing your knowledge and your time with the listeners. I know they'll get a lot of great value out of what she shares. And that's all for the executive connect podcast. You've been listening to the executive connect podcast. If you have questions or ideas on how to bring leadership to the next level, email us at executiveconnectpodcast@gmail.com.

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