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From Startup to Success: Lessons from Entrepreneur and Investor Jeff Amerine on Building Venture Ecosystems (#387)
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Nov. 18, 2024

From Startup to Success: Lessons from Entrepreneur and Investor Jeff Amerine on Building Venture Ecosystems (#387)

From Startup to Success: Lessons from Entrepreneur and Investor Jeff Amerine on Building Venture Ecosystems (#387)

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Exclusive Insights from This Week's Episodes

“Enjoy the journey.” - Jeff Amerine

In this episode, Jeff Amerine, a recognized leader in venture ecosystems and entrepreneurship. Jeff provides insights into the challenges and successes of building ventures in unexpected places, focusing on small business and startup ecosystems. 

05:53 Jeff Amerine's Background and Journey

18:54 Defining Success in Entrepreneurship

21:54 Challenges and Common Pitfalls for Startups

33:09 The Importance of Culture in Business Success

45:41 The Impact of AI on Business

Essential Resources to Maximize Your Business Exit

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Transcript

387 Jeff Amerine

Jeffrey Feldberg: [00:00:00] Today's guest is a powerhouse in the world of venture ecosystems and entrepreneurship. Jeff Amerine is a nationally recognized thought leader who has played a pivotal role in creating lasting venture ecosystems across the country. He's also the co author of the Amazon bestselling book, Creating Startup Junkies: Building Sustainable Venture Ecosystems In Unexpected Places. 

Jeff's experience speaks for itself. He's held senior leadership positions in nine startups and major Fortune 500 companies, including American Freightways and FedEx Freight. With over 90 venture investments under his belt, Jeff's impact on the entrepreneurship landscape is profound.

Currently Jeff is leading the charge at Startup Junkie Consulting and co leading Innovation Junkie and Cadrone Capital Partners. He's also made significant contributions to academia, serving as an Associate Vice Provost for Research and Economic Development and as the Director of Technology Ventures at the University of Arkansas before transitioning to focus fully on Startup Junkie Consulting in 2015. [00:01:00]

Despite his busy schedule, Jeff remains an adjunct professor of entrepreneurship at the Sam M. Walton College of Business at the University of Arkansas, a graduate of the United States Naval Academy, and a former Air Force officer.

Jeff holds a Master of Science in Operations Management from the University of Arkansas. Jeff is not only an expert in his field, but also a mentor, educator, and entrepreneur who's left an indelible mark on the business world. So buckle up for an insightful conversation packed with wisdom, experience, and practical strategies for building sustainable businesses. 

And before we start this episode, a quick word from our sponsor, Deep Wealth and the 90 Day Deep Wealth Mastery Program. Here's Jane, a graduate who says, and I quote, the Deep Wealth Mastery Program prevented me from making what would have been one of the biggest mistakes of my career. I almost signed on the dotted line with an unsolicited offer that I now realized would have shortchanged my hard work and my future had I accepted that offer. Deep Wealth Mastery has tilted the playing field to my [00:02:00] advantage.

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Welcome to the Deep Wealth Podcast. Well, Deep Wealth Nation, we have a fellow entrepreneur in the house. This is [00:05:00] going to be a lot of fun because our guest, as you heard in the official introduction, hasn't just been involved in building companies all the way through to some of the largest companies in the world to now being behind the scenes when it comes to funding companies, exiting companies, everything else in between.

I'm going to put a plug in right there. Jeff, welcome to the Deep Wealth Podcast. Firstly, Congratulations to your parents. I love the name they selected for you. Probably the best name in the world. Always terrific. And even spelled the right way. It's perfect to speak to another Jeff in your case, Jeffrey in my case, but welcome.

So happy to have you here.

Jeff Amerine: Yeah, Jeffrey, thank you for having me on. And you're right. We had good parents. They, good first name, right?

Jeffrey Feldberg: And before we get going, I firstly want to thank you for the service that you gave to the country back in the day, doing what you do, allowed us to do what we do, and thank you so much for that. And you're now giving so much back to really everyone, to not just locally, but really across the board. But let me ask you this, you have a really interesting story, and there's always a story behind the story.

So Jeff, what's [00:06:00] your story? What got you from where you were to where you are today?

Jeff Amerine: Yeah it's, kind of a long and winding road, honestly. I mean, the family business for me was the military. I grew up as a military dependent. And my dad was a command pilot over 10, 000 hours flying everything that had multi engines in the Air Force inventory. And that's kind of what I grew up with and all my brothers and sisters And in fact, we learned more about the family genealogy is all the way back to before the Revolutionary War. We were serving even in the Continental Army during the Revolutionary War. So that's what I grew up with. It was the environment. That had little to do with entrepreneurship and had a lot to do with this is what I'm going to end up doing, this is what I've grown up with.

Give you an idea. Six different elementary schools. This was during the Vietnam War days. My dad was being reassigned a number of different times to junior highs. And then finally he retired to the sort of rural area in North Central Arkansas and life kind of changed. And I went to junior high and high [00:07:00] school in a small kind of rural place.

So you imagine sort of cosmopolitan kid who lived all over the world and all over the country. And then I'm deposited in this town of 7, 000 people that was a little bit like Mayberry, for those of you that would remember that, reference. then when I graduated high school, I was off to the Naval Academy, kind of following in my dad's footsteps.

He'd been an Air Force officer. got an appointment to the Academy and quite honestly, in 1980, I never thought That I'd be back. I thought that, life was going to take me on a 30 year career of being in the military. Well, it turns out the Cold War ended in 1990. I actually took my commission in the Air Force, like my dad did.

And at that point, it was an on ramp to industry. So, I spent a Time over the course of the next many years is as a leader in three Fortune 500s, primarily in technology leadership roles in nine different tech startups in multiple different sectors from telecom to software to transportation, et cetera.

and I became a startup junkie in every sense of the word. That was something that wasn't an [00:08:00] expected path. What really triggered me to head that direction was I took a new ventures class in a graduate program that I was in. It kind of opened my eyes to something that I didn't realize I had a predisposition towards.

I loved the clean sheet of canvas and the possibilities of coming up with a venture of your own creation and building a team. And I didn't mind the adrenaline and the risk associated with having to raise money and do all those sorts of things. And so That was kind of the catalytic moment.

It was something I never really realized would be a path, and it ended up being a path that changed kind of the rest of my life. A number of things along the way, I moved back to Arkansas in around 2000 to be closer to my folks. They were elderly and kind of felt called or compelled in some ways because I had three kids, one more on the way at the time, and I needed to be closer to them.

I just felt like I did. And it turns out The year or two after we got back, my mom was diagnosed with Alzheimer's. My dad needed a lot of help kind of dealing with that. And so it was one of those things [00:09:00] that, not to get too spiritual, but I felt like there was an element of divine intervention. And then that set the course for everything that has happened since.

I spent time in one more Silicon Valley based startup. I built the transportation logistics vertical here in Arkansas, which is kind of a logical place to do that if you know anything about the history of what goes on in the area, and then spent seven years at the University of Arkansas running their technology commercialization function and teaching a little bit as an adjunct, which is something I always thought I'd probably do in retirement.

I just did a little bit earlier. And along the way, I got pulled into the startup scene, which I thought I'd kind of graduated from, quite frankly to be part of a program called Innovate Arkansas, which was funded by the state and managed at the time by Winthrop Rockefeller International, one of the NGOs.

That's the Rockefeller family created. And it was all about mentoring and supporting tech based startups. And that's what led to the creation of the Startup Junkie Brand, which is a leading entrepreneurial support organization, Catering [00:10:00] Capital Partners, which is an early stage VC, and everything else that we've done since.

And ultimately, after all those years as an operator, the thing that I was really always supposed to do is what I'm doing right now. And that's where I've been engaged the last 16 years.

Jeffrey Feldberg: What's interesting, and wow, quite the story there. That really is the story behind the story. Every one of those turns could easily, Jeff, easily be an episode. There's a theme here though, before we get up to the whole startup junkie, you're paying it forward. You're giving it back. You're helping. You're educating, whether it's back in the education circles or in the private equity or entrepreneurship.

And so I'm wondering when you look back on your story with what you just shared. Is there one specific defining moment that set you on that path to entrepreneurship or was it an accumulation of things? 

Jeff Amerine: Really was that sort of graduate MBA project where you had to come up with a new venture, and this is far before [00:11:00] Lean Canvas and customer discovery and some of the later techniques. It was more about write a business plan, do some research, try to launch something. That whole experience. Made me think, I'm really not a great large organization person.

I'm always been, I've been accused of being a renegade or a rogue cowboy or whatever else. Just not great in large organizations, because I won't say that I was necessarily always trying to break a regulation or bend the rules, but there were elements of that. And so I think that was kind of the catalytic thing where I said, I felt like I needed to go launch something on my own.

And quite honestly, in those days, if I'm being really candid, I was pretty self absorbed, probably pretty confident. A lot of entrepreneurs are, you feel like you can take on the world and. That analogy or the cliché has been used too often about, you're not afraid to jump off the mountain with the box of parachute parts and the symbol of parachute on the way down.

And I felt like that. I felt like I could go do this stuff. Now, some of that, you [00:12:00] get dealt sort of a rude awakening that you're not always as good as you think you are, and you have a lot to learn, and time on earth brings that wisdom. But along that way of entrepreneurship, realizing how hard it was, particularly in the 90s, you were alone, there weren't really mentoring groups, there wasn't a lot of organized angel capital, VC capital wasn't everywhere in the country, it was mostly In Silicon Valley, that was sort of the compelling moment that made me think there's a better way.

These early stage startups need the support, they need the service, they need the advice, they need the guidance, they need the connections, but they have one thing in common. They're terrible customers because they have no money. So you've got to come up with a model that will work. For them, that speaks to the fact that it's economic empowerment, and it can have huge economic impact, but they can't afford to pay you for that service.

And so that's what, that was kind of the genesis of what became the Startup Junkie Model, and what's used by a number of entrepreneurial support organizations across the country, whereas the services are free, and they're funded by [00:13:00] third parties like federal government, state government, and foundations.

That

Jeffrey Feldberg: It's incredible what you're doing in your book, by the way, Deep Wealth Nation, go to the show notes, click on the link, get the book, Creating Startup Junkies, Building Sustainable Venture Ecosystems in Unexpected Places, And in chapter three, you put it right out there, entrepreneurship in the U. S., fly over states.

And so when you started Startup Junkies, was that part of it in terms of reaching out to those who otherwise likely wouldn't have access?

Jeff Amerine: of it just by virtue of proximity, right? I happen to be in a place that is a classic flyover state that has, even though it has some of the largest corporations in the world like Walmart and J. B. Hunt and Tyson and others, it's often overlooked and it's often burdened with the low expectations. People think there can't be any signs of intelligent life there.

There's probably not much going on. And so you begin to develop a little bit of the chip on your shoulder of, The one advantage that people like Sam Walton and Johnny Bryant Hunt and others had was they did [00:14:00] unexpectedly outsize things into places that had every disadvantage you could imagine. And so with that kind of in mind, we said, look, if these guys could do it with every disadvantage, Why can't others build fantastic, scalable ventures here in a place where you've got the right kind of work ethic and a good DNA towards building good businesses, but low expectations.

And so that's part of what I think compelled myself and my business partner, Jeff Standrich, along with our team members to write the book, Creating Startup Junkies, back in 2021. We wanted to give that belief. To others that if we could do it in this place, you can do it wherever you are and start where you are and take advantage of the fact that you've got the work ethic.

You don't have to be in the Valley or in New York or Boston. There's no reason why you can't build great businesses right where you are.

And to your point, and I'm sure we'll touch upon this at one point, because you're really off the beaten path, you're not competing with the big names. You're [00:15:00] What you're paying for salaries and getting out to the right talent pool becomes maybe not as easy where you have more people in a larger city, but I would suspect you have some key advantages that you're just not going to get in Silicon Valley or some of the other expected places.

But if you fast forward to today, Jeff, so you started the Startup Junkie and you now look at today, I mean, where's the mission and vision? How's that evolved?

Yeah, I mean, it's still so a good thing would be to kind of. Paint the picture of what happened in Silicon Valley over the course of the last 75 years. So the key point is it was 75 years, right? Major General Draper came back after running the Marshall Plan. He, along with others, said we need a different way of thinking about how to grow scalable ventures and how to bank them.

And that was of the beginning. And you could go back to Fairchild Semiconductor and all the other things that happened out there. But it was a 75 year journey. So a lot of times, Economic developers, municipal leaders, state leaders, they say, well, what's it going to take for us to create Silicon Valley where we are?

First of all, you're not [00:16:00] going to. those people that apply that Silicon moniker to whatever else they're doing, and I won't name names. It's a cheap way of diminishing the brand that you're trying to build and associate with something that's way different and unique and probably can't be replicated.

And so we thought about it. What are the assets? What are the aspirations? What are the market constraints? And what can be built right here? So you look at. Our area, it's things like retail and supply chain and agriculture and defense and how do we build something that's really interesting with the talent we have locally and the talent we can attract in because we do have the advantages of not just a good.

Low cost quality of life. And some of that's gone up with housing, but also the advantages of the natural beauty being less than 10 or 15 minutes from a river where you can fish or kayak in thousands of miles of cycling trails at the Walton family, the founders of Walmart have put in [00:17:00] place and a lot of other cultural amenities.

So there's. Those aspects that become kind of an attractant and also with the fact that when you begin to tell the story of Sam Walton or Johnny Bryant Hunt, the founder of J. B. Hunt, people are inspired by that. It's something where they look at that and they say, anything is possible with a little bit of support and hard work ethic.

This is a good place to build it. And so those are some of the elements that come together. And the one thing I would say too, that's unique to this state, it's a state of 3. 2 million people total, about 600, 000 in the metropolitan service area that we call Northwest Arkansas, which is Bentonville, Rogers, Springdale, Fayetteville, Asylum Springs.

They're all kind of little towns, but the advantage you have is In any given coffee shop corner in Bentonville, you could run into the CEO of Walmart, or an executive vice president, or a senior leader from Procter Gamble, or Unilever, or any of those other large players, and they're accessible. Try to do that in L.

A., not going to happen. There's a zillion [00:18:00] people, and the proximity to really important decision makers and the fact that they're approachable is something that's kind of unique to this area, and it Building enterprise focused tech companies or consumer packaged goods companies really appealing because you can get access to the people you need to be able to make sales and build relationships.

Jeffrey Feldberg: And for many, it really goes back to, at least for me, as I'm hearing you share the story, my own experience, really the ethos of entrepreneurship. Hey, it doesn't matter where you're coming from or where you're at. We're here together. We're here to find a painful problem. We're going to make life better.

And if you do it well enough, if you solve other people's problems and you do it for enough people, you help them get their dreams, eventually you'll have your goals and dreams. And it really creates a win and all really political aspirations aside, regardless of what side you're on.

Entrepreneurship, at least for me, just, it cuts through all of that back to the better days and back to where the North Star was in the right direction. But I'm wondering, when someone comes into the Startup Junkie ecosystem, what would you tell [00:19:00] them in terms of success? How does success, and how would you define success for yourself and the companies and the entrepreneurs that you're helping and mentoring today?

Jeff Amerine: Yeah, it's a good question. part of that, how you define success is a very personal thing. Success can be measured in lots of different ways beyond just, What's in your bank account and sort of the financial outcomes for the venture you're building. I think Guy Kawasaki said it best. He said, a lot of people are thinking about how do they stack up big piles of money or they're in it to make money.

That tends to be not a great motivation on the front end of building a business. He says, find meaning. Finding meaning is important. So starting with a real problem you care about that's going to improve lives. That's kind of a good place to start. And that's part of what we do, what we try to do. And you'll see it in any of our branding.

It's about educating, inspiring, improving the lives of entrepreneurs through giving them the tools they need to be successful. We think economic empowerment in that way is important. And we [00:20:00] also So I guess part of it, to get back to your original question is we encourage people to define success in a very personal way.

It can't really be a pattern match with what someone else thinks. It's gotta be personal to you. And it's also gotta be something where when you wake up on the hard days when you're choking on your toothpaste, 'cause you're wondering how you're gonna make payroll. That answering that why question, well what's our purpose?

Why do we need to exist? We'll keep you motivated because, as you well know, entrepreneurship is a slog. It is it's got a lot of lows and some pretty good highs, but you've got to be resilient and ready for that kind of stuff. How you define success, how you understand your own resilience, the difficult journey, all those things are really important.

And we also try to Be very Socratic in the way we do triage with clients initially to whereas we don't say this is our system and we've been doing this for 35 years and these are all these successes. It's really more of trying to find out, found [00:21:00] out what their motives are, who they, what problem they think they're solving and then rather than providing them the answer, illuminating a path.

That only they can travel because it's their path. Now, along the way, we'll give them some advice and guidance, but it's never, this is the only way it's more of, look. These are the questions you ought to be asking at this point. These are some tools to find out more about the true demand for the problem that you're trying to solve, et cetera.

Jeffrey Feldberg: Spoken like a true mentor and visionary of, hey, I'm not going to tell you this is the way. Think about it. Here's some questions. So why don't we start at the beginning and then we'll flash forward right towards the end. When you're either working with a company that's now brand new, it's day one, they're working with you.

Or you've even said no to some companies that want to become part of the family, but it just doesn't make sense. Some people call it Pareto's Law, the 80 20 rule. Are you seeing the same 20 percent of the issues that are creating 80 percent of the challenges [00:22:00] that these companies face that's going to either put them out of business or hold them back from a market disruption or from really enjoying large growth?

Jeff Amerine: Yeah, the Pareto Principle definitely applies. we tend to not turn people away. I mean, some might have described us as the Ellis Island for startups and small businesses. We'll take all comers. What separates those that continue to go forward from those that not is we introduce them to the rigor that's required to actually build something.

And then typically they'll self select out. They don't want to go out and talk to a hundred people and do customer discovery, or they don't want to complete a lean canvas, or they're not coachable, they don't want to take feedback, all that kind of stuff, and so they tend to select, once they get the homework, they will self select out, but in terms of the issues we see, the typical sorts of things, people Rather than doing market validation and asking good, open ended questions, they come with a confirmation bias because they've asked all their friends and family, and they've gotten this sort of reinforcement that it's a great idea, even though, particularly in the [00:23:00] South.

They won't, people won't give you a straight answer because they don't want to hurt your feelings. So you've got to listen for that encoded, well, bless your heart. And if you don't know what that means, that your idea really stinks then you're diluting yourself. And so we try to encourage them to be consultant to their own ideas and to really look for those demand indicators that are out there.

The other thing where we see a lot of, failings or difficulties are founder issues or talent issues, not having the right people on the team, not having them in the right seats. Not having the right incentives. Those are kind of common issues that are a problem. Not having if they're trying to build a technology platform, a technical co founder, a senior architect, thinking they can outsource that, which is impossible to raise money if you've got third party tech in a tech based business, in our judgment.

We certainly see that sort of thing. The one thing somebody, a mentor told me 35 years ago, maybe more in one of my early ventures, he said, Jeff, if you can't get the small things right, no one will have any confidence that you can get [00:24:00] the big things right. So that lack of a focus on attention to detail, you start to see trends where founders can't show up on time, or they're not responsive, or as an example, on investment side, they can't get a data room together, they don't respond well to answers, or they progressively disclose can you see this?

These are all the ten steps of what you need to do to be aware who you are in terms of being able to make money. It's all about the recommendations you're making. You've got to make money. You got to be looking very hard for this. I encourage you to do everything to go through one of these steps of what you want to do, no matter how much it's taking you, no matter how much it's costing you.

But work with your investors. Your investors are looking at you, they're looking at you, and they're asking, hey, what about you? Not telling CSI something. They're going to find out. You may as well tell them. mean, that's kind of a grab bag of things, but those give you some pretty good examples of the stuff we often see.

Jeffrey Feldberg: And Jeff, as you're walking through that, I'm really in my mind going through a number of different things. One of the things that's coming to the surface And it seems to be really a dividing kind of question. There's really two [00:25:00] camps to this. One camp says anybody can be an entrepreneur. Another camp says, well, hey, not so quick.

You've either got it, you're born with it, or you're not. Not everyone can be an entrepreneur and it's just your God given gift. And if you don't have it, that's okay. You have other gifts. Find those and leverage that with your experience. You know, You're approaching four decades of now doing this. And even before that, I mean, you've just been doing so much of this, so much exposure to different kinds of people.

Where is it at for you? Are we born with entrepreneurship within us? Can we learn that if we're not? That's

Jeff Amerine: It's a classic question of nature versus nurture. And again, I say, there are people that have a strong predisposition, maybe an inclination, maybe the way they were raised. Maybe they grew up in entrepreneurial families, maybe it's second nature to, to have a high risk tolerance or the ability to handle a high degree of chaos and ambiguity, which I think is what it takes to be a good entrepreneur.

But I'm also a believer that it can definitely be learned and taught. I think it's a skill like [00:26:00] anything else. It's really a mindset. See a problem, solve a problem. I think entrepreneurialism is something that can exist in big companies. It can exist in nonprofits. And it's really about having a strong dissatisfaction for the status quo and being willing to challenge things and try new things and not afraid of failure.

The small incremental failures, those are feedback. Those are opportunities to learn and to iterate. So I think it can be educated. I think there are people that have a stronger predisposition for it just because they can handle. A little bit of chaos, a little bit of ambiguity, and they're not afraid.

Some of it being back when I was in the military, we used to talk about how far could you push yourself into the pain cave? And it was that element of, not taking counsel of your own fears. So I think that people that maybe have a high degree of tolerance for that might do better, but entrepreneurs are not sort of.

Complete unqualified risk takers. They're really good at identifying risk and coming up with [00:27:00] mitigations if they're successful at it. I think it can be learned, and I've taught it, for 15 years, but I think it's helpful if you do have some predisposition and that high tolerance for ambiguity.

Jeffrey Feldberg: so interesting. Looking back on my own journey, I put myself under the microscope. I was a train wreck that was waiting to happen when I first began. But Jeff, having said that, because I just had a passion for it, those mistakes which I learned from, a diamond doesn't just show up, it takes really time and pressure.

Same thing with entrepreneurs, at least in my experience, and here in our ecosystem at Deep Wealth, as we have from startups to very well endangered companies that are going through, they've been in business for decades, they go through it, they learn, they really learn from that. Completely agree with what you're saying.

But let me ask you this, we started at the beginning of, okay, a company shows up and they don't really have the right habits, or they don't have necessarily that experience that can be the North Star. Let's fast forward now. If I could put you on the spot, is there a success story that you might be able to share that really shows, hey, here's what happens at Startup [00:28:00] Junkie when you come here, versus one of our success stories.

Here's where they went through the hero's journey, and here's what they achieved. Anything that you can share for the Deep Wealth Nation?

Jeff Amerine: Yeah, I mean, there's probably several that would be interesting, but good example would be couple of guys who had been mid level software development firm, and that software development firm had a really nice exit, they sold to a large multinational, and were a They were fairly highly valued at the time based on having some major accounts around the Walmart universe.

These guys had been, one was the lead architect, the other was sort of business development type. They thought there was a better way. They didn't actually actively participate in the equity didn't have options when that exit occurred, even though they were mid level or senior level guys. And so they built a business that was also an agency started from the very beginning with a very high focus on a strong culture. And a good commitment to participation of the employees in whatever upside would come along. And so [00:29:00] they didn't do kind of what I would call classic stock options. It was more a phantom stock. But when that company had a recapitalization after about six years, these guys started out working out of the Bentonville library.

Building the business. They didn't raise very much money in the beginning. They kind of built the business based on the backs of getting customer contracts. They grew it to where the recapitalization from a private equity firm, it was it was probably a 70 million dollar recapitalization. And as part of that, the employees were able to take an exit, as were some of the early advisors, and he created 13 new millionaires through that process.

And that's, I don't mind saying that company was called Rev Unit. You could look it up. And then it also shows that there's a time and a season for everything. The market changed afterwards and ultimately that business kind of went the other direction after the recapitalization. But on the way up, it was run exceptionally well under the leadership that built it.

And it highlights a couple of things. One is [00:30:00] culture, as I think it was Drucker said, we'll eat strategy for breakfast. And I really think culture, a strong culture and talent are part of any good strategy more than being a replacement for it. But that's one good example of they've just two guys ended up having a hundred and some employees.

A nice recapitalization. And even though ultimately it wasn't a long term success beyond that recapitalization where a bunch of people took the money off the table, it was an example of what's possible in a services business. Another one we saw, and This particular one was called AptoG, run by a guy named Justin George.

It was a company that grew out of a concept he had at a startup weekend that we participated in. he had a strong predilection towards business development and sales, a natural sales guy. But I can remember when he first pitched this particular business, which was focused on a school districts, I thought, I can't think of a worse vertical to sell into.

They have no budget. [00:31:00] They're going to be difficult. They're going to be very needy. I mean, terrible. I mean, maybe transportation is worse, but I don't know. School districts seem really tough. But all he managed to do was raise a number of venture capital rounds. Five Elms was his lead for the Series A. We were a syndicate on that.

Five Elms is based in Kansas City. And they ended up having a nice nine digit exit for that business. And he dominates, still today, that business dominates. The school district marketing went from zero to 3, 500 school districts, and platform itself was essentially consolidated communications for the school administrators, so that they need to talk to coaches or staff or faculty or students.

They had one consolidated way to do it, and the thing that was so unique about it was, he built the best place to work, this one happened to be based in Little Rock, in that entire area. Everybody wanted to work there, and it wasn't because it was all fun and games, or they had ping pong tables, it was because of what they got to do, [00:32:00] and the culture.

It was a culture that was very much focused on winning, and a good example. In their sales meetings, they were extremely responsive to customer needs and demands. They never used PowerPoint presentations or other slideware. They had a sales process that was completely unique and differentiated. And Justin was a guy that said, if you want to be successful and have outsized success, You've got to figure out how to differentiate every aspect of your business, not just the product offering.

You have to think differently. And he did an amazing job. And we were with him from a startup junkie standpoint, from a fund standpoint, from the very beginning, all the way through to exit. And it was remarkable. I mean, we can't take a whole lot of credit for that other than, we were there as a sounding board, as a coach, as a connector, but it's just an example of the importance of good leadership and talent.

And if you build the right culture, you'll attract the right people.

Jeffrey Feldberg: Love the story, Jeff, particularly with education, which is near and dear to me, with my startup that went on eventually to the exit, [00:33:00] Embanet. In education, I could relate to everything that you're saying and all the naysayers, but it goes back to that vision and that passion and you just find a way where others say there is no way.

What's interesting in those two examples, those many case studies that you shared with us, it brings me back to the book, actually. You talk about the four pillars of ecosystem building, talent, culture, community engagement, and capital. Let me focus in on chapter five of the book, Culture, because for us at Deep Wealth, Culture as well, in our nine step roadmap, step two X Factors, a foundational X Factor, it's your culture.

Money can buy a lot of things. The competition cannot, with the money, replicate or copy your culture. It's like our fingerprint. It's just so unique to us. So in your experience, both the good and perhaps the not so good, can you talk to us about culture and the role that it ultimately plays in a successful company?

Jeff Amerine: the culture is huge. I mean, the number one asset of every business is the talent. so there's, [00:34:00] culture can be a marketing eyewash that gets put on placards or on banners or on websites, but that's not really it. it's how people internalize how they feel about what they're doing.

Really strong cultures are such that's what you're going to use to hire people. That's what you'll use to fire people. They're talked about tactically, daily, in staff meetings, the whole bit. And it's not just sort of marketing hoo ha or choreography. It's really what people believe, a strong connection to beliefs.

It's also how you select your customers. Sometimes a culture can define you. We're not going to try to do business with everybody, because if there's not cultural alignment, they're not going to be a good customer, they're not going to get the benefit of working with us. I think it's huge. I think it's really important.

In fact, when we do due diligence on any investments, it's something we look at real carefully. What's the culture like? Sometimes you can tell. A good or bad culture just by the churn rate on employees, ties directly to the brand promise and what their [00:35:00] customers or their partners will say about them.

I think it's, hugely important. Culture is, one of the defining factors of a good strategy and I've not seen long term sustainable winning business that had a bad culture or a suspect culture, frankly.

Jeffrey Feldberg: And you're so right, because right at the beginning you mentioned talent and culture, and I agree, for me, they're really indistinguishable. If you have great talent, no guarantee, but more than likely, your culture reflects that. You'll have a rich and thriving culture. Let me ask you this, though, because for culture, one of the areas, as an entrepreneur, even dealing with my customers, my companies are now in a Deep Wealth ecosystem, our community.

When it comes to culture, some say when people are let go on a regular basis. Not a good thing to have that revolving door. And on the flip side, you can also say, well, if there's no revolving door, if everyone just stays in and the B players and the C players are mixed with the A players, not a good thing either.

Where is that balance? And I show this because for my [00:36:00] companies, there is a revolving door. We're always top grading, if I can use that term. And what was an A player last year, that may only be a B player this year. And let's always put the customer first. We take care of the customer. We take care of the business.

We take care of the team. Everything else will take care of itself, but not everyone agrees with that, so where are you on that in terms of how do we deal with our talent, and when what was good yesterday isn't necessarily the same for today?

Jeff Amerine: think you have to have a clear eyed view of that, right? Gino Wichman from the book Traction has this concept of, do they get it, do they want it, do they have the capacity, the capability to actually do it? I think you have to have the right view on that. And occasionally, you'll find high performers.

That don't have some of those other attributes, and you have to invite them to leave. And if people don't perform well, it can become a level of toxicity. If you tolerate mediocrity or less than stellar performance, things that aren't aligned with some of ours, or do the right thing, go the extra mile, a bias towards action, have fun, if they're not aligning with those, You've [00:37:00] got to invite them to go and you have to do it pretty quickly or else it erodes that shared culture that you have.

So I would describe churn as sometimes involuntary churn is necessary. You need to invite people respectfully and diplomatically to their future elsewhere at times. And that's the way you keep it strong. And I would also say cultures are not static. They should be constantly improved or redefined as you bring new people in.

The culture can be improved. As you go, it's not something where you set it in stone at one point and it's going to be that same way forever in the business.

Jeffrey Feldberg: Yeah, so interesting, and you're right, it's always situational. Speaking for myself, I don't know where you land on this, one of the most difficult things, well, actually the most difficult thing, no matter how long I've been an entrepreneur. It's when there's not a fit, and you have to sit down with that person, and when it came to having people be like, oh, I want to be involved in that just because it's such a big thing, I never got used to that.

But the toughest part for me was some of the team, particularly in a startup, the [00:38:00] talent comes on board, you are slaying those dragons, you're conquering, but the company grows and the marketplace changes, and that initial talent, as good as they were back in the day, Don't necessarily have the skills or there's not the opportunity to have 'em go into different directions.

And ultimately there's not a fit for me that as one of the toughest calls to ever have to make when that comes up.

Jeff Amerine: Super tough. this is where particularly with early employees or founders, you have to ask them to be a little bit reflective and introspective because there's a time in the season for the capabilities you have. As an example, I'll personalize this.

I'm pretty good on the vision, on the creation, on the launch. I'm not a great operator to go from that sort of adrenaline junkie stage to significant scale and growth, and I'm definitely not a crank turner in a large organization later. So if you can, as a founder, as an early employee, if you can put the shareholder hat on and constantly say What should I be doing to increase the shareholder value and the benefits this [00:39:00] company can deliver both to our customers and our team? That can bring some clarity, but as a leader, having to bring people back to that can be exceedingly difficult. I'll give you a good example without necessarily naming names.

I'm on the board of a company that had three original founders. And one of the founders who was the CEO was kind of the glue that held the other two together. And the other two, one was highly scientific, sort of chief scientific officer, the other was kind of a pure, somewhat abrasive sales machine.

When the glue, that original CEO founder passed away, the other two became co CEOs. And the culture began to erode very quickly because they didn't have that sort of Eisenhower like approach. Ability to bring people together that the original CEO had. And so as a board, we had to step in and bring them to the base truth of you guys are significant shareholders in this business, but you need to take a step up to the board and we need to [00:40:00] bring in the operating team and a new CEO that can take this to the next level.

Otherwise this business that's at 40 million in sales today will never be 400 million in sales because you two don't have the capacity to do it. And that was really tough. It was extremely hard, and it's always hard to tell somebody, you were great up to this point, but you're not the right person for the next stage.

Jeffrey Feldberg: So true. And thinking of winning mindset, step five in a nine step roadmap, and for me it was perhaps a little bit easier because I knew Jeff as the company Enette was growing. I said, Hey, I'm not the corporate type. I'm not really the one that has the skillset to take the company to the next level. Could I have done it?

Possibly. Would I have enjoyed it? Certainly not. And so for me, it became quite clear. Okay, this is the time now. Let's bring in professional management. Let's look at bringing in investment partners to help take the company to the next level. it goes back to mindset. We always put the company first.

What's best for our customers? What's best for the team? We have our team members, their families are [00:41:00] depending on us. Their livelihoods are depending on us. It can't be that they're not. As nice as it is, it just can't be about me or my founders. It's got to be really, we're at the bottom of the list. It's got to be everyone else first, but easier said than done for some when that's going on.

So I couldn't agree more with you. I'm wondering because you wear a lot of different hats. You're a mentor, you're an investor, you're a business owner. I don't believe in the word balance. I prefer to use blending. I think balance, go to Hollywood or go to a fiction book, you're going to find balance. For me anyways, that balance concept hasn't existed, at least in life.

That's why it's more of a blending. But how do you blend that mentor, investor, entrepreneur, what's going on with that personally?

Jeff Amerine: Yeah, it's a really good question. And I always kind of chuckle a little bit when people say work life balance, and there's never any balance. I mean, it's, a bit of an episodic thing where you're sprinting and you're chaotically busy, and then figure out ways to take time to [00:42:00] recharge and whatnot.

think, and maybe this is undiagnosed, ADHD in my case, but if you're a shiny object person at core and you like being exposed to a lot of different things and you have a lot of interest, I think that lends itself towards being able to take on a lot of things. And be involved with a lot of things.

Now, the key with that is you have to have really good people at that next echelon that allows you to kind of pick your spots, dive in where you can dive in and add value. And the train still runs in a smooth, methodical, point A to point B way. And so the only way I've been able to do. What I've been able to do is we've had a structure where we have really good, using again, Gino Wickman vernacular, integrators that are process oriented, that can build in repeatability, and that allows me to do what I love the most, which is helping clients directly doing events, being on podcasts, all that sort of external fun stuff where I'm, I enjoy it and it [00:43:00] gives me energy.

And then the process oriented stuff that is so critical, you gotta have good people to do that. Keep the train on the tracks,

Jeffrey Feldberg: And really, kudos to you for recognizing, hey, that's not really me. Let me do what I do best. I'm going to lose the shackles or the golden handcuffs. I'm going to have other people in it, even if they're not 100 percent as good as you. In my books, if they're 80 percent as good, and sometimes they're 180%.

Better, but at least someone is doing it. It's more scalable. It's more replicable, and you get to focus on what you do best. I'm wondering, Jeff, you have the benefit of being able to look back so you can look forward. And so where you sit today, and this can change later today, it can change tomorrow.

What's the future for Startup Junkie? What's going on there?

Jeff Amerine: Yeah, it's a good question. Something that we, we wrestle with a lot. And again, a little bit cliche, but I kind of believe it. You spend a lot of your life focusing on success. And then you think, as you get to a certain age, What can we do that's really significant, that's going to be kind of a lasting legacy, [00:44:00] that's going to improve lives and whatnot.

And so we made a reasonably good dent in the startup ecosystem within the central U. S. I mean, we're kind of a known quantity, et cetera. We've got a footprint in Seoul, South Korea, but we think at this point is I think, what are the next 20 years look like? I want that impact to be. What can we do to impact more lives to, to spread this sort of startup venture, small business mantra, and how to do it well to more people.

So for me, we're constantly trying to figure out how do we make a bigger impact? Is that through having more digital content that's widely available on a worldwide basis? Is that through geographic expansion? And we're evaluating all that. The one thing we're not going to do, as some other people have done in the Entrepreneurial Support Organization, is just peanut butter the brand over 50 markets instantly, because it tends to dilute what you're doing.

So we're going to be very selective, play to the things that are of interest to us, where we feel like we might have some comparative advantage. Play to our [00:45:00] strengths, but it is going to be about expanding both digitally and somewhat geographically to have a larger impact. At the end of the day, I'd like to look back and say, we deal with 10.000 entrepreneurs a year And they're having this kind of success and we're changing lives and it mattered, that's what I see the next 10 to 20 years looking like.

Jeffrey Feldberg: It's a terrific vision, and again, from the outside looking into what you're doing, but also where we are as a society, as a country. It's those kinds of values, those ethics, again, Data. 01, but for me, that's really where I feel we need to get back to and it's terrific to see that you're out there and promoting that and really making that accessible.

For others, where it may not otherwise be. And let me ask you this, before we go into wrap up mode, this could easily be an episode in and of itself. Artificial intelligence, AI, by the time this episode comes out, it will have changed already and everything will be obsolete and out of date. How does AI, or does AI, impact what you're doing at Startup Junkie and obviously the companies as well in the [00:46:00] ecosystem?

Jeff Amerine: I love that question. I'm glad you asked it because, first of all, for now, six different cohorts, we've run what's called the Fuel AI ML Accelerator. And we were early on in that. In fact, we were so early on, after cohort or two, we said, OK, Maybe we ought to change this to automation because it seems like it's cooling off.

Well, then there was this democratization with open AI and all the chat, GPT related stuff, and it blew up again. And so now my point of view on that is there's going to be two types of companies over the course of the next 10 years. Those that fully embrace the power and figure out how to use it as a force multiplier, and those that go out of business.

I think it's one of those imperatives to figure out how it can be used to make the staff you have more effective, more efficient at doing things that today burn up a lot of time. So we're figuring out how to integrate it in a lot of the we do. Content development research. Intelligence. As an example, one of [00:47:00] our toolkits is focused on the Lean Canvas, Lean Startup Methodology, and Customer Discovery.

Well, we had an associate in another company build an AI based platform that takes some of those mundane tasks And Automate, the tool is called Oxygen, A U X I G E N DOT A I, and it's, so people that are like, I don't know how to come up with these customer discovery questions I'm not sure how to fill out the Lean Canvas.

There's now a tool that will allow them to do that. We're looking at every aspect of what we do and trying to figure out what's a good use case for it, how can we be more efficient. And our clients, we're giving them kind of the same message to say, you got to figure out how to embrace it, and it's not the dot com area where you just say AI this or ML that, it's got to actually be a use case.

that matters, that solves a real problem. And if you're on the buy side, they're only looking at, is this going to increase revenues or decrease costs? So if you don't have a good value justification and ROI story, they're not going to care that it's AI [00:48:00] driven, whatever. But again, we're somewhere on the trough of, the upswing of the trough of disillusionment, probably, but I think it's going to be a game changer across every industry.

Jeffrey Feldberg: And it's fascinating to watch as it's a story that continues to evolve and grow really across society, business, everything, life as we know it. Jeff, let me ask you this. There are so many questions I didn't get to ask. So many directions I would have loved to have gone into are beginning to bump up into time.

Before we go into wrap up mode, if Is there a question that you would have liked me to ask that I didn't or a topic that we haven't covered? Even a message that you'd like to get out to Deep Wealth Nation?

Jeff Amerine: Well, first of all, thanks for that. And I think you covered, you asked some really good questions and you covered a lot of good ground. I would just say the key message for me, this will be a message both to entrepreneurs and people that are thinking about what they can do in their regions, in the flyover areas or other sort of unexpected places, focusing on startups and small business.

is a sustainable approach to long term [00:49:00] economic development. Most of the economic developers think in terms of attracting a plan or smokestacks or whatever, and that's a little bit like trying to buy a winning lottery ticket. You're going to win some, but not very often. Whereas, focusing on small business and startup and building that sustainable ecosystem, even in smaller areas, That's the money ball play.

For those of you that are familiar with that movie, that's the on base percentage. That's the guy that doesn't look like the athlete that's actually going to still be there and is just going to keep getting on base. And so the message is, first, read the book. Great. I mean, creating start up junkies a good read.

But more importantly, don't be discouraged. Figure out how to build something in your area with the talent that you have, and other talent and other capital will come if you do. And it's sustainable. It's the only thing that's really going to be guaranteed to stick if you focus on it.

Jeffrey Feldberg: So true. When you get it right, you can be off the beaten path. The world will beat a path to you when you're world [00:50:00] class in what you're doing and you're hitting it out of the park. Couldn't agree more. Well, let's do this. Let's go into wrap up mode. It's a tradition here on the Deep Wealth Podcast, and it's really, you I say this every episode.

It's so true. It's my privilege. It's an honor where I ask the same question to every guest, and it's a really fun question. Let me set this up for you. When you think of the movie Back to the Future, you have a magical DeLorean car that will take you to any point in time. So imagine now, Jeff, it's tomorrow morning.

You look outside your window. Not only is the DeLorean car there, curbside, door open, waiting for you to hop on in. What you do, you're now going to go back to any point in your life, Jeff, as a young child or a teenager. Whatever point it would be, what would you tell your younger self in terms of life lessons or life wisdom or hey, Jeff, do this, but don't do that.

What would that sound like?

Jeff Amerine: Yeah. I love the time machine question. And actually, we had a guest one time on our podcast, the Startup Junkies podcast, and I asked that and he said, well, let me get this straight. I've got a time machine. You know, Maybe I can, I can do all kinds of amazing things with the time machine because I've got a time machine.

But [00:51:00] It's a valid question and I would say if I could go back and advise my younger self I would probably say enjoy the journey a little bit more particularly in the entrepreneurial ups and downs. I was always focused on getting there, getting to that destination. And there were a lot of times where I missed out on things in my children's lives.

I was pretty self absorbed. I would say enjoy that journey. enjoy the ups and the downs, and realize that the journey is the important part. The destinations are important and all the accolades that come from it, but enjoy the journey. And as I've gotten older, I've gotten much better perspective on that.

I enjoy every day, just, Being able to do what we do. I wish I had enjoyed it a little more when I was younger, but I think some of that you just have to go through that self-absorbed stage to realize that's no kind of way to live.

Jeffrey Feldberg: Yeah, such terrific advice. Enjoy the journey. Jeff, I'm right there with you. I miss, for my first child, a lot of the early years and I can't remember the [00:52:00] meetings that I was at. They obviously weren't important. I do remember what I missed. And Deep Wealth Nation, Jeff is sharing some platinum advice.

Enjoy the journey. Take the time out. It's not likely as urgent or as important like you think it is, and if you fast forward a year, even a month or five years. You'll realize, hey, yeah, that wasn't such a big deal, so that's some terrific advice. Deep Wealth Nation, in the show notes, we have all the links to the book, to the podcast, to the company.

But Jeff, if someone wants to reach out and have a conversation, maybe even explore how they can become part of one of your portfolio companies, or part of the ecosystem, or just hear some of your insights, where is the best place online to reach you?

Jeff Amerine: Oh, yeah. they can hit me up on LinkedIn. linkedIn, look for Jeff Amerine on, on LinkedIn. I'm on there. They can even email me as well. I don't mind that at all. If they want to email me at jeff@startupjunkieconsulting [dot] com, always happy for that. I enjoy the conversations and so feel free, I look forward to it.

Jeffrey Feldberg: Terrific, Deep Wealth Nation. You heard it. Take Jeff up on his offer. He has been there. He's done that from [00:53:00] startup to exit to the corporate world, everything else in between. Investor, thought leader, entrepreneur, author, podcaster, the list goes on and on. Jeff, it's official. Congratulations. It's 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.

Jeff Amerine: Jeffrey, thank you for having me on. It was great. 

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 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 [00:54:00] 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.