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Serial Entrepreneurship Navigating the Risks and RewardsSerial Entrepreneurship Navigating the Risks and Rewards

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Show Notes


Welcome to the latest episode of the Executive Connect Podcast. Host Melissa Aarskaug spoke with Jeremy Lessaris, a seasoned entrepreneur with a diverse background in building and selling businesses across various industries. Jeremy shared the highs and lows of his journey, insights into the payments landscape, the impact of technology, and offered valuable tips for scaling and exiting businesses. Learn about the challenges and opportunities in today’s entrepreneurial landscape and get practical advice on growing your business.

Key Takeaways:

00:00 – Introduction

05:30 – The Evolution of Payments Technology

  • The payments landscape has become increasingly seamless, allowing for quick and easy transactions.
  • Despite the convenience, small to medium-sized businesses often bear the brunt of high transaction fees, which can be predatory.
  • Machine learning can help small businesses negotiate better transaction rates.
  • The convenience of modern payment systems often hides the high costs for smaller companies.

09:03 – Impact of AI and Machine Learning

  • AI and machine learning are transforming various industries, including payments and customer interactions.
  • There’s a growing value in handcrafted, human-interaction-focused businesses as a counterbalance to AI-dominated services.
  • AI’s influence will likely increase, but human-centered crafts and services will see a resurgence.
  • The blend of technology and human touch can create unique opportunities for businesses.

19:33 – Strategies for Scaling Businesses

  • Focus on sales and revenue as the primary drivers for scaling.
  • Bootstrapping can lead to more disciplined and careful financial management.
  • Building a strong sales foundation is crucial before addressing other aspects of the business.
  • Bootstrapping helps entrepreneurs prioritize profitability and sustainability.

20: 36 – Mentorship and Networking

  • Having mentors and a strong network is invaluable for entrepreneurial success.
  • Mentors can provide guidance, support, and valuable insights that are crucial for growth.
  • Seek out mentors who can offer practical advice and support based on their experiences.
  • Building a network of supportive individuals can significantly impact your business journey.

27:35 – Balancing Work and Personal Life

  • Striving for a balance between work and personal life is essential for long-term success and well-being.
  • Entrepreneurs should build businesses that align with their desired lifestyle rather than compromising their personal lives.
  • Consider how business decisions impact your day-to-day life and overall happiness.
  • Aim for business models that support a healthy work-life balance to avoid burnout.
  • By focusing on these key takeaways, listeners can gain a deeper understanding of the current entrepreneurial landscape, the importance of technological integration, and practical strategies for achieving business growth and personal fulfillment.

Guest Bio:

Jeremy is a serial entrepreneur, investor, and former global marketing & communications executive. Over the past two decades Jeremy has founded and led eight of his companies to successful exits. Jeremy is currently the Founder & CEO of Payment Brokers, a fintech company, focused on AI-enabled cost reductions.

Personal LinkedIn – www.linkedin.com/in/jlessaris

About Melissa Aarskaug:

I’m an energetic executive with 15+ years of experience steering companies to new heights of growth and scale. An engineer at heart (I started my career as an engineering manager on one of the world’s largest concrete bridges), I’ve become a trusted leader and business builder in the technology and cybersecurity space.


Jeremy Lessaris 00:00
I challenge every small business owner. If they take credit cards, they should take their statement out. They should take the total fees and divide it by their revenue and find out what percent they’re paying. And if they’re paying above, you know, 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.

Narrator 00:31
Welcome to the Executive Connect Podcast, a show for the new generation of leaders. Join Melissa Aarskaug as she speaks to a wide variety of guests that bring new insights into leadership, prosperity, and personal growth. While no one 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.

Melissa Aarskaug 01:01
Welcome to the Executive Connect Podcast. I’m excited to have Jeremy Lessaris 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?

Jeremy Lessaris 01:17
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 the 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. And still operating companies still building things, love ideating new things, not a great operator. So I like to build them get them to a point and kind of 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 blanks 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 are really filling in the gaps where I found, you know, ideas or things that I could help myself and 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, you know, accelerate the 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, you know, 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. I’m 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, 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, not take over mine was, you know, early on was 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 impact me? How is it going to impact my day to day at what is 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 an 18 hour day? A seven days a week, you know, stuck behind a desk. So that’s really been my journey.

Melissa Aarskaug 05:06
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. How do you think technology is changing the payments landscape?

Jeremy Lessaris 05:37
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 sized company. So I’ve 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 gonna say machine learning, it’s not AI, but we use a machine learning tool to look at the cost for 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 dollars 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 buy 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 processes 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 these little businesses, they’re carrying, sometimes five or 6%, to just transact money. And it’s, it’s almost predatory. I mean, I hate to say that, because I’m sure I’m sure there’s going to be a cease and desist at some point. But I would, 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 higher risk fee, you know, so it was like really difficult early on for me. And now that payments are secure and seamless. And it makes it very effortless, effortless to go through a checkout process. Like you can go online and buy anything in two seconds. Now, that’s great. That used to be like a seven page, you know, 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 10%, just to transact a credit card. It’s just not right. 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 it’s a fun product. It’s also putting money back to people’s bottom lines easiest, 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 hand crafted 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 it. You know, handmade the stories, the Humanality of a company and not necessarily like, yeah are CEO’s of robot and you know, 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. I don’t know if I I don’t know if I like that world, I think I much rather like actually talk to people and shake hands and, you know, actually interact with humans. So I think there’s going to be a bigger value placed on things that are done manually, and, 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 in machine by AI and everything is AI. So so I feel like that’s going to be a little bit of a resurgence of kind of a second renaissance of craft.

Melissa Aarskaug 10:52
Yeah, absolutely. I mean, as you were talking about how easy it is to use payments, I kept thinking about, you know, when I’m riding trains in Europe, how easy it is to use my you know, Apple Pay to scan in, I have to go up to the you know, machine and buy a ticket and put a credit card in and enter my you know, 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 and carried all my cards and all my things and all in 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 you mentioned transact and do businesses. So I, I do love the ease of that, at times, I’m a little concerned cyber from a cybersecurity 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, you know, people want to take out money from an ATM. Now, they could charge anywhere from $2 to, you know, like you said, 6 to 9% to get $14 out. 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 other organizations. So I do see that from my side and my industry as well.

Jeremy Lessaris 12:22
But I mean, you see it, 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 gonna pay it. So we have immediately hyper inflated 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 her, 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, American Express, they’re like, these are the bad guys. So they went after him. They’re like, there’s a bunch of legislation that they’re really attempting to pass right now. There was a recent settlement for billions of dollars and potential, you know, fees that they’re going to reduce. And then a week later, they raise the pricing. So I mean, it’s, it’s, it’s unfortunate that we’re targeting them when the problem isn’t really Visa Master Card, 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 reseller, I mean, there’s so many layers of people now touching this 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 that it’s we’re a sticky solution. It’s like, that’s not really free market choice. And I get it, you know, a few provide tremendous value. And there are companies that do, you know, there’s a really well known service industry software that everybody uses. And they partnered with the 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 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 Master Card, came back and said, You know what, we’re gonna not only help you do this, we’re gonna 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%. Herein lies the major problem and there’s no controls like they, 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. Like, take out your statement and your credit card processing statement and look at it. That’s it. That’s the first pass. The second piece is like, the more this gets technologically integrated, the harder it’s going to be to unplug 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 went, Oh, man, did I just it’s so easy to pay now. And there’s no more cash. I mean, it costs money to get cash out, like what you were just saying, there’s a game around ATMs. Like, hey, we’re gonna charge you a flat $6. So what would you do take out more cash? Well, we’re gonna cap, you can only take out 100 bucks. So like, no matter what they’re getting 6%? Money. It’s crazy. So it’s bad. But it’s also like, okay, there is a convenience part of this. And 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 gotta get Brinks. They gotta come pick up all their cash, they got it, it costs money to move that money, their 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 leapfrog technology. I know, everybody, you know, pushed a lot of eggs in the baskets for cryptocurrencies, which I am 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, Master Card. I mean, they’re posting record numbers, absolute record profits. So I don’t think that’s going to change anytime soon. And I’ll be honest, I like my 2%, two and a half percent cashback. I like my rewards, like I like going on trips for the spend that I normally have. No, I wouldn’t give that up. So it’s, it’s a hard unplug, that’s for sure.

Melissa Aarskaug 16:58
Yeah, and I think it’s, 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, you’re somewhere to, you know, Amazon things to where there’s so much happening regularly and a month for people that are buying things? And that’s partially why visa is, you know, 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, you know, for shipping. They don’t want to wait, they want it today now, and that is the world we live in, they want to be, you know, they want to have their products they want to, you know, be the perfect way they want it now today. No, they don’t want to work out immediate gratification or gratification.

Jeremy Lessaris 17:46
Yeah, when you push a button, you know, there’s a comedian that talks about, you know, your order a pen, and it’s that you’re like, I just want to ship one pen, you know, like, Prime now shows up today. You’re like, that’s amazing.

Melissa Aarskaug 17:58
Right? People need convenience, right this time.

Jeremy Lessaris 18:01
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 that 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.

Melissa Aarskaug 18:20
That’s a good 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 out there, you may not have purchased, or you may be went out to dinner, and the bill is 50 bucks, but it’s 150 bucks on your statement. So call the restaurant get it reversed. It’s an error. I wanted to make it a little bit.

Jeremy Lessaris 18:43
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, you know 2.3, 2.29, 2.2 they need to really look into it. Because I have seen companies that are paying 6% There’s absolutely no need for that. I mean, that’s it’s crazy that they have silent partnerships anyway, I didn’t mean to interrupt.

Melissa Aarskaug 19:17
No, no, definitely. That’s a really good point. I’m glad you. I’m glad you brought it up. I want to ask a question. I know eight successful exits is a really big deal. And I think that is a true testament to you as a leader, as a visionary. You know, one of the questions I want to you know, get your perspective on is how you how did you grow and scale these businesses? Do you have any tips, strategies that you can share with our listeners on how you were able to do that?

Jeremy Lessaris 19:44
So, I always pause when we talk about eight exits to clarify what eight exits looks like. Because everyone goes wow, that’s so glamorous. And you did all these, you know, sold 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 failing, hemorrhaging money, had no idea how 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, 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. 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 I there’s no way I could have done half of the things I did without the mentors, I had my former bosses for 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 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 I have, our logo has to be perfect. And our, 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 focused on sales. And I’ll fix everything else, you know, it was like jumping off the cliff. And we’ll build a plane 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 down this path. And it 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 startup, 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 I 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 like there’s not a 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 I need to do so they end up hurting the the the monies that needed to be reinvested in these startups don’t get back there. Because I hate starting to make money. Great, I’ll start taking 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, like 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 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 people recognize when you’re hungry to to grow, right? They 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.

Melissa Aarskaug 24:47
Yeah, I love to hear that as a sale as a revenue driver sales professional, I would absolutely agree there’s always going to be flashy things, spend money on a brand new office and you know, you know fancy pens and all these But I think I absolutely agree with what you said, you said is focusing on the revenue driving sales. And then the other thing, just to touch on that I loved you said is focusing on what matters, right? There’s so many polls 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 loved 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 been? Like, maybe the question is talking about your entrepreneurer, going from a W two employee to an entrepreneurer, and what’s driving that for you?

Jeremy Lessaris 25:52
So my father started at really young, and he was a serial entrepreneur. So growing up, I watched him build carwash, I watched him build, Detail Shop and all these like 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, multilevel marketing. I was literally a baby going to MLM meetings. My parents were like, really, they got indoctrinated really early, like Amway global reach, 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 detail 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 it, but they’re like building blocks, but their lifestyles. 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 1000’s of dollars that year, that over a summer. And to me, it was like my first taste of entrepreneurer. And being an entrepreneurer. And from that point forward, it was on. So like, I took that money invested in arcade game, which I thought everybody’s gonna put coins in it. So I’ll still own the arcade, but I’ll have this other income. No kids put any money in except me. And it was a failure. So I got my first taste of success and failure, like back to back in one summer. From that point forward, it was just a journey of what I thought I wanted to be. 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 gonna be this multimillion 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 recognize 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 our lives in England, and was a customer of mine who like took a liking to me because I was 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 gonna get a great job, people are gonna 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. There was no nights or weekends. It was just burned through idea after idea after idea. And I loved it. It was addicting 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 a it was a drug. It was my hobby. I was intrigued. I only wanted to talk about business all the time. My friends are kind of like they’re into 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 stuff. I care less. Like what does 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. So that was the pivotal moment of what did you just do? My health was failing, my teeth were bad. Like, my eyes were shut, my hands hurt from being on a computer. My back was art, like, 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. It 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, Alright, let’s celebrate. And then it was like, I haven’t seen you in like two years. I 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.

Melissa Aarskaug 31:17
I think that’s key is is and I want to zone in on some of the things you said. And you know, I laughed that she said, the lemonade stand in the MLM one of my first mentors was a diamond at Amway, and I used to be them at a and I would listen to his pitches and his meetings, and he was a partner at a firm and he was like, Melissa, you gotta 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 use this word a lot when I speak in, you know, either talking about tech or a 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 build a business to to find a spouse to raise good kids, stepping back and analyzing where you are, am I living? My best life? Is this in line with my values? I building a business, but my health is suffering, I have no friends. So I think you know, one key point is in to the listeners, a lot of you guys are executives, leaders, leading big teams doing big things, but how’s your personal life? How’s 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 and your journey professionally and personally. So switching a little bit? You know, I think backs again, eight exits. When is the right time 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 negotiate the sale? And maybe maybe what have you learned from selling?

Jeremy Lessaris 33:02
There’s no right time. There’s no, there’s no formula for this that I have. I mean, 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 think 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. They’re like, I’m gonna build this thing up, and it’s gonna 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 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 Fs To 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’s 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 bind 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 evaluation. Yeah, I’d agree I 99% of the time, it’s just about, listen, I, 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 then take taxes out? Where you left is? Are you sure you’re ready to exit? Is this is where you want to be? Do you want to put an operator in place like 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 make sense to do. For me, it was like, I got a couple of them, I had no choice. I was approached by an investor. That gave me a great offer. I wasn’t, 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. That 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’s fast with a lot of heartache.

Melissa Aarskaug 36:39
It’s very true. Very true. couple last things before we close want to be mindful of time. Just maybe some final two final questions in area maybe that you’re bullish on as far as technology. And then any advice, just your final thoughts on what you’ve argued 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?

Jeremy Lessaris 37:05
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, like what that could put this one out of business. And this could change this and like, 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 it 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 wish and my advice.

Melissa Aarskaug 38:29
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 you share. And that’s all for the Executive Connect Podcast.

Narrator 38:46
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 And don’t forget to subscribe so you can catch every new episode. Until next time.

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Bryan Hancock Headshot — Founder of Integrity Development

Bryan Hancock

Founder of Integrity Development

Integrity Development

Executive Biography

Bryan Hancock has been managing real estate investments—and overseeing development and construction projects—for nearly two decades. He has deep roots in Austin, Texas, and comprehensive knowledge of the opportunities and challenges in this fast-growing market.

Through his development and syndication companies, which he built from the ground up, Bryan has developed 50+ urban infill projects and managed $25M in real estate sales with approximately 35% return on investment at the project level. He also co-founded two private equity funds.

Bryan brings in-depth industry awareness, sharp business acumen, and extensive in-the-trenches experience to his work as co-founder and principal of Integrity Development. He partners with a team of professionals and industry experts (many have been involved in Austin real estate for 40+ years) to identify value-added and opportunistic investments that protect capital and reduce risk for lenders—while delivering outsized returns for investors.

Earlier, Bryan founded and directed Inner 10 Development, a residential development firm focused on Austin’s top zip codes and surrounding communities, and H2i, LLC, a real estate syndication company. He steered these organizations for 17+ years, overseeing the acquisition, buildout, and sale of single-family and multifamily properties, including a 350-unit urban infill joint-venture project.

Bryan was successful in delivering strong returns while minimizing risk for bankers and investors by taking a targeted, data-driven approach to opportunity analysis, due diligence, and strategic decision-making. He zeroed in on potential risks and developed proactive mitigation strategies to protect and grow investments.

Concurrent with his work at Inner 10 Development and H2i, Bryan established Gentry Lending Group, a private-equity debt fund. He also served on the board of Bullseye Capital Real Property Opportunity Fund. These experiences provided Bryan with a grasp of both investor and banker viewpoints, including an understanding of risk and liability on the lending side. This aspect of his background continues to shape his real estate decisions to this day.

There is another unique aspect to Bryan’s career—a corporate history that differentiates him from other investors and developers in this field. Bryan has built organizations, controlled multimillion-dollar projects, and supported billion-dollar programs for some of the world’s largest companies: Lockheed Martin, Microsoft, Dell, CACI, and Charles Schwab. He managed teams and vendors in the US, China, France, and India, and often balanced up to 10 projects at a time. He was trusted with a Top Secret Security Clearance from the United States government.

A business-savvy leader and lifelong learner, Bryan holds an MBA in Finance and Entrepreneurship from Texas Christian University and a Bachelor of Science in Electrical Engineering from the University of Texas at Austin.

Bryan founded the Wealth Investment Network, co-founded RealStarter (a crowdfunding platform for real estate investors), and was a member of the Urban Land Institute and Central Texas Angel Network. He has been a guest speaker at 20+ national events, including conferences and meetups through the Information Management Network (IMN), SXSW, Rice University, Bay Area Real Estate Summit, Soho Loft Conference, Texas Entrepreneur Network, and many others.

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Melissa Aarskaug Headshot — Founder of Executive Connect

Melissa Aarskaug

Founder of Executive Connect

Senior Executive, Board Member & Advisor

Vice President of Business Development
Bulletproof, a GLI company

Executive Biography

Melissa Aarskaug is a global executive and business leader at the forefront of the technology/cybersecurity industry. She shapes strategy, leads teams, and partners with Fortune 500 companies and other enterprise clients to protect their organizations from risk and noncompliance—while improving operations and accelerating growth.

For 15+ years, Melissa has taken the reins to propel organizations to the next level of performance. By combining business acumen and revenue optimization with the sharp mind of an engineer, she uncovers and seizes opportunities for profitable growth in the US and around the world.

Melissa has established a distinguished career with Gaming Laboratories International (GLI), where she is a key member of the senior executive team. Throughout her tenure, she has assembled teams, developed new markets, and influenced P&L impact, ultimately positioning GLI as the #1 provider of testing, certification, and cybersecurity services to the global gaming and lottery space.

After achieving this feat—a big win for GLI and game-changer for clients worldwide—Melissa steered both GLI and Bulletproof (acquired by GLI in 2016) into untapped verticals: finance, government, healthcare, higher education, hospitality, and retail. An enthusiastic, knowledgeable growth driver who cultivates partnerships and rallies teams, she led GLI/Bulletproof to dominate these markets as well.

Before joining GLI, Melissa shaped and executed strategy as Vice President of Business Operations for LV Investments, where she built and optimized a portfolio of commercial and industrial properties. Earlier, in a very different role as Project Engineering Manager for Fisher Industries, she directed and mobilized a team of 550 employees and contractors to develop the world’s largest concrete bridge. Previously, she headed a major engineering project for Pacific Mechanical Corporation.

A curious, lifelong learner, Melissa holds dual Bachelor of Science degrees in Civil and Environmental Engineering with minors including Business and Mathematics. She is a Karrass Master Negotiator and C4 Executive Coach who actively pursues ongoing education and inspiration as a member of Chief, Austin Technology Council, Austin Women in Technology, and Toastmasters International. In addition to her own personal and professional development, Melissa is committed to helping other people thrive both inside and outside of the workplace. She actively mentors and empowers team members at GLI/Bulletproof, and is an executive leader and coach for Global Gaming Women. She founded Young Nonprofit Professionals Network (YNPN) Austin and is a current or past board member of many organizations, including Emerging Leaders in Gaming, Ballet Austin, Texas School for the Blind & Visually Impaired, the Society of Women Engineers, and the American Society of Civil Engineers. She has been a Junior League volunteer in Austin, Las Vegas, and Reno for 15+ years.

Throughout her career, Melissa has inspired individuals, teams, and entire organizations to think differently about innovation, cybersecurity, leadership, and business development. She was honored as one of the “Emerging Leaders in Gaming: 40 Under 40” and she continues to share her ideas and expertise through publications, podcasts, webinars, and presentations.

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This is the Executive Connect

A show for the new generation of leaders. Join us as we discover unconventional leadership strategies not traditionally associated with executive roles. Our guests include upper-level C-Suite executives charting new ways to grow their organizations, successful entrepreneurs changing the way the world does business, and experts and thought leaders from fields outside of Corporate America that can bring new insights into leadership, prosperity, and personal growth – all while connecting on a human level. No one has all the answers – but 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.