284 Bryan Clifton

Jeffrey Feldberg: [00:00:00] Welcome to the Deep Wealth Podcast where you learn how to extract your business and personal Deep Wealth. 

I'm your host Jeffrey Feldberg. 

This podcast is brought to you by Deep Wealth and the 90-day Deep Wealth Experience. 

When it comes to your business deep wealth, your exit or liquidity event is the most important financial decision of your life. 

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Bryan Clifton helps founders, families, and next generation leaders align their vision for success with the life they want to live and the legacy they want to leave. By focusing at the intersection of business and psychology, Bryan equips entrepreneurs, families, and organizations with the tools needed to better navigate uncertainty. 

Growing up in a family business that ultimately collapsed. Bryan deeply understands the [00:02:00] challenges that impact the family and the business. He believes that pursuit of entrepreneurial activities can be a blessing to a family, but it can also lead to its undoing. All of the work he does is motivated by his life goal to see more happy and healthy families. 

Bryan holds degrees from Pepperdine University and Harding University. He has been named 40 under 40 by Oklahoma Magazine, Edmund Young Professional of the Year and Innovator Of The Year by the Journal Record. He serves as trustee for the Oklahoma City National Memorial and Museum. 

In pursuit of education, humanitarian and religious interests, Bryan spent time in over 45 countries, including extended tours in Greece, Haiti, Guatemala, Hong Kong, and the Philippines. He's been married to his wife, Mariah for seven years and has two daughters, Millie and Reese. He lives in Edmond, Oklahoma. 

Welcome to the Deep Wealth Podcast, and we have a fellow entrepreneur, business owner, founder market disruptor with us. I am so excited for [00:03:00] this episode. But I'm gonna pause it all there with one question before I formally introduce our guests. So all you business owners, founders, entrepreneurs out there that you're in a family business, or maybe you're a startup and you don't realize it yet, but it will become a next generation family business.

How are things going? Because I know when it comes to family business, you're in a league of your own. But some of these family businesses literally transform the world, and we're gonna be talking about that, how to do it the better way, and to have strategies that you haven't perhaps heard about or you think aren't even possible.

So we'll put a plug on it right there. No more spoiler alerts. Bryan, welcome to the Deep Wealth. Podcast, an absolute pleasure to have you with us. And I'm curious, Bryan, there's always a story behind the story. What's your story? What got you to where you are today?

Bryan Clifton: Well, Jeffrey, thanks for having me. I'm thrilled to be on the podcast. I have felt like I have been in business literally my entire life. So I grew up in a family business and if you've ever seen the fake teeth that make you look like a hillbilly that was my family's company. So we sold toy and novelty items.

Our kind of [00:04:00] unofficial tagline for years was, if it's in good taste, we don't carry it. 

So a lot of remote control fart machines and bullet hole stickers on cars just gag gift items that every kid. Thought was hilarious. 

My mom did not find those as funny most of the time. But we spent a lot of time, or in the early days of that business at state fairs and Christmas shows and things like that back in the mid nineties 

late nineties, early two thousands.

And so I've grown up. In business, literally my entire life. And I always thought that it was normal to be a fifth grader and working on inventory and then doing reconciliations on financials and making sure all the cash lined up, and then reordering that product from whatever appropriate distributor it was.

And I legitimately thought that was a normal childhood. And so everything that I shared today gives you a little bit of background of why I am the way I am, because my childhood was odd. But it helped shape a lot of the ways in which I think and how I view business and entrepreneurship today.

Jeffrey Feldberg: I love that. I love how just growing up that really sculpted you. [00:05:00] You thought that was the norm, as is really the case with so many successful entrepreneurs, but from fake teeth to fart machines. Here we are today, Bryan. What a story. What a bad. Ground, and I'm sure we can go down all kinds of rabbit holes on that, but let me ask you this, for the benefit of our listeners who, as I mentioned earlier, my little preamble there who are either in a family business, multi-generational, maybe they're the next generation, maybe they're the next generation that's actually coming up, their transition hasn't happened, or perhaps they're in startup mode and they don't know yet that it will be next generation.

We'll plant some seeds with 'em today. Bryan, what's going on out there? That you're tackling this incredibly complex and painful problem, and you're so unique out there, you're making a huge difference. What should we know

Bryan Clifton: Yeah, so for most businesses, whenever you get started, you don't have a guarantee that it's going to be a family 

business. And so what I always tell people is do not make the assumption that your business today is going to stay in the family. Family, but the decisions you make today may be closing that door.

And so I always like to look at it from a standpoint of some businesses need to [00:06:00] have a natural expiration date or a natural closing. They're not meant to be 70 year old businesses. Some of 'em might be really good for 10 years. 

That's what that business needs to do. 

And so if you want to create a family business, one, you have to look at, am I in an industry that could actually have sustaining power?

And just because the answer to that may be no, does not mean you're in a bad 

industry. It just might mean that this industry is on its way out, or there is a certain window of time where it's very applicable, or the size you would've to grow that company to is pretty drastic in order to be able to compete longer term in that horizon.

But the way that you structure your business, especially how you interact with capital early on 

in the days of a business. Open and close those doors of could this be a family business? So we haven't even got into the family dynamics, the family skill level, but just the fundamental, legal, tactical basics of how your business is structured, how you brought in investors or maybe didn't that.

All of those kind of ingredients make up the recipe of if a business could even [00:07:00] possibly pass down to a future generation down the road.

Jeffrey Feldberg: So Bryan, you bring up an interesting point, and before we move forward with this, perhaps you can give some insights, some really strategies from the field that work. So family businesses out there, and I know when we work here at Deep Wealth with various businesses, some of them are family businesses, oftentimes the next generation, a common theme that we hear is, I never really had a choice.

It was just assumed I would be running the business, and that's how I was groomed, and that's how I did my education. Those were my expectations, and even if I wanted to do something else, I really had no choice in the matter. That's a whole other topic, but how can the current generation really check their egos at the door and determine, well, is this a business worth passing on to the next generation in the first place?

Bryan Clifton: Yeah, whenever I work with families, one, variable that always has to be on the table 

Is the best decision for this business and for this family to either let it die 

or to sell it. We make an assumption that passing it on is the best option. 

It is [00:08:00] a option. It may not be the best option. 

What I have seen, so I did my master's from Pepperdine, specifically within family business dynamic and family business transition.

And in my thesis, one of the things that became very evident to me is I was interviewing a plethora of different business owners that had a family member successor option. Inside their company was if I want somebody to be my successor son, daughter, son-in-law, fill in the blank. Whoever that person might be.

If they do not have the ability to say no, 

then their yes doesn't mean anything either. 

So if I am passing this business down to my son, because I assume that's what he wants, but he does not feel like he could say, dad, I don't want to run this and dad actually hear that. Then his other answer is irrelevant because he only felt like he had one option choice.

Whenever that happens, all we've done is we have kicked the can down the road of a potential family, split 

a family dysfunction, and typically a business dysfunction. It is not going to be an immediate [00:09:00] response. It's normally about three to seven years down the road, depending upon market conditions, depending upon size.

But when somebody feels like they do not have another choice, but to say, yeah, I guess I'll take it, it is setting up a dynamic that is going to lead to a family dynamic that few people want. But it happens a lot because they think. Well, this is what we have to do. 

This is what it means to be a good member of this family.

This is what it means to respect my father, or I wanna try to impress my father-in-law. So that's what I have to do, 

but it rarely leads to a good, healthy dynamic within the family.

Jeffrey Feldberg: Bryan, as you're talking about that, what's interesting when you think this through, big picture wise, if you were to ask, well, what's the outcome? And the answer usually is we want the next generation to have a lifestyle, a comfort level, something productive, something that they can do. And we'll forget about the means to the ends and how we do that.

And to your point, well maybe the best way to do that is to sell the business. Because it's not really a sustainable business or go through the family split or the fights or all those other kinds of things. So points well taken [00:10:00] there. So once you get beyond that, tell me what really big picture wise, the kinds of dynamics that you're working in.

Because as are listeners heard in the official introduction, you are a traveled person. Over 45 countries you've been to, you have really an incredible insight into world culture, human dynamics, and what's going on out there. So big picture wise is a Britto's law that's going on here, Bryan, where 80% of the issues that you're seeing in family businesses are coming down to call it, give or take 20% of the same root causes.

Bryan Clifton: I mean, in almost every family dynamic there is some sibling some cousin that has gone off the rails in some 

way. They have a drug addiction, they've had failed marriages. They have had inability to kind of find their footing and. Certain aspects within the family will revolve around how do we help take care or how do we help bring that person back in 

to a family dynamic?

I see that issue quite a bit. I also see the fact of if you've watched succession or any of those pieces where you have multiple [00:11:00] siblings that are all trying to vie for the same position, and so there can only be one c e o, and so I feel like if me as the firstborn male am entitled to that, yet my sister is.

Equally or maybe more qualified. How does dad make that decision? 

What does that look like? Most of the time, what I have seen, especially businesses that are run or founded by men, if they are still married to the first wife or the woman who is the mother of the children, normally she wants family continuity

While the dad wants business success.

And those are not exclusive and that is a stereotype. But I normally see that dynamic to where, especially once grandkids are involved, it's how do we keep the people together where they will want to be in a conversation, they'll want to come over for Thanksgiving, they'll want to have the ability to be in each other's lives and those aspects about how we interact as a family.

And you overlay that. With what the business needs. [00:12:00] Those become sources of conflict. And I've got your basic three to five spots. And one of the things that comes up a lot is unresolved issues that have been a recurring narrative since childhood. 

So siblings that have the same fighting patterns, the same frustrations or the same dynamic with a parent that they've had for 20 or 30 years.

And it's just manifesting itself differently at this age 

and at this life stage. But oftentimes whenever I look at that transition, I. From one generation to the next. The spot that so few people think about is just because the business has succeeded up to this point, has no bearing on its ability to continue to succeed moving forward.

And so I spend a lot of my work and my team spends a lot of time working on, okay, so we can navigate the legal, the tax aspects of a generational transfer of all those elements. But what is the fundamental strategy of the business moving forward? And oftentimes it needs a. Fairly robust disruption of itself in order to be relevant for the next decade or the next two decades because the outgoing [00:13:00] generation tended to reduce the risk 

and not want to unnecessarily take odd risk as they are trying to Exit.

But the incoming generation sees, I need this to work for 30 years, 

and so what do we need to do to reinvent and disrupt? And that becomes a tension point because new generation comes in and starts making changes, and outgoing generation can feel like. Oh, so you thought I didn't know what I was doing.

You had to come in and change everything. And so it can be seen as a sign of disrespect 

or it can be seen as a sign of you're trying to come in and take out all this knowledge that I used to have, because oftentimes, especially if you've got a 5,000, 200 person or more company,

If I have a ownership transition, the other senior leaders are normally not far behind in age.

They're normally a five to 10 year age gap, and so you could have an entire changeover or a 70% changeover of a leadership 

team within a three to five year time period, and so it can feel like the company loses its roots if you don't have good. Core [00:14:00] values, principles, understandings, but also realizing that those roots are meant to adapt based upon the market.

And that just because you did that in the eighties doesn't mean that's what you need to do in 2030. How can I use those same principles and values to be able to interact with this market instead of saying, well, that's how we have always done it, so we have to keep doing it that exact same way over and over again.

Jeffrey Feldberg: Bryan, when you're brought in early enough, and I suspect that's probably, unfortunately not the majority of the time, but if you're brought in early enough, how do you head that off at the past that you actually don't have to go through that? What kinds of things or systems, strategies are you putting in place?

Bryan Clifton: Ideally, we would have about a three to five year time horizon 

where a transition is known. Everybody is aware of that. But we may not have a set date yet, but we're working towards it. 

So if we have a three to five year time horizon, we can assess what are the skill sets of the desired recipients of that baton?

What are their current competencies? What do they need to grow in, both for the current operations of the business, but [00:15:00] also where it needs to go? Do we have that amount of runway? Do we have that time? That is an ideal scenario because we can work through a lot of those family dynamics. We can help anticipate potential pain points before they become.

An issue. I also want to have a deep understanding of how does the family deal with conflict. Some families, they yell and scream and they get it all out there. Others, they look very peaceful on the surface, but 

they have a lot of hidden issues under the surface that you've really gotta unpack that are really driving a lot of those actions.

So that three to five year time horizon is ideal. So, Far too often we get brought in a crisis, 

Hey, I want to transition in six months. Or, Hey, I've tried this and it's been a complete mess. Can you help me clean this up? 

Or, business has lost 30% of its value in the last six months because I handed it over to my son-in-law and he wasn't actually competent.

But I don't want to take him out because I'm afraid of how it's going to. Impact my relationship with my daughter and she's got a baby on the way and my like, so you get all of those very real [00:16:00] family scenarios that happen in a crisis. We can be very valuable, we can be very helpful, and not every transition is a family dynamic issue.

Sometimes founder had a heart attack. Or they had an accident, they mentally are incapacitated because of a stroke or something else. That's a different type of scenario than an internal family fight or an internal board feud or anything along those lines. the actions may still be the same.

You have chaos, you have uncertainty, 

you have lack of clarity about what needs to happen. You may have a cashflow issue, but the actions for each of those are very different because we're working from different starting points.

Jeffrey Feldberg: So Bryan, for the listener who is saying, you know, Bryan, I wish I knew you three years ago because that's exactly where I am today, and obviously I didn't know you, and we just went face forward into this chaotic crisis of a situation. What do you do today? So if you're brought into this situation where it's happening in real time, it's failed.

Everyone's at their woods end. What can we do?

Bryan Clifton: I always ask people to [00:17:00] start with, what are you trying to create? Are you trying to create a scenario that has cashflow certainty? Are you trying to create a scenario that has family unity? Are you trying to create a situation that has business opportunity for the future? What is your driving force behind these actions?

Because some people, especially founders, will say for years that they want somebody to take over their business. They have the best of intentions in that, but whenever it actually comes down to it, they don't want to leave. They want to stay. And so I always have to ask a little bit of a question of how are you contributing to the problem that you're complaining about?

So if you are in a situation that you do not like time for some honesty, some self-reflection, how are you contributing to that problem? Are you bringing people in, asking them to lead and then undermining? When they actually try to do that, are you unable to attract the type of talent that you want? Are you making [00:18:00] excuses for people that never should have been in those positions, that they didn't have that last name or that blood in their veins, or they didn't marry in at the right 

time?

And sometimes the best thing you can do for your family is to not put them in charge.

The absolute best thing for them as a family unit and for the company.

Jeffrey Feldberg: Let's talk about that. And all too often it is the case where perhaps mom started it, or mom's father started it, or dad started it, or dad's father started, whatever the case may be. And they have the kids and now you're onto the second generation or the third generation.

The family's getting larger. And you have daughter-in-laws, son-in-laws who are coming onto the scene, and you do have that political pressure and parents wanting to do what they feel is right for the kids. Why I want my son or my daughter to have a good livelihood. So I will put so-and-so into the business who's a non-family member, who's a family member now will buy marriage, where maybe on paper it seems like the right thing to do, but it really isn't.

They don't want to succumb to all those pressures. So how do you deal with that? How do you have [00:19:00] that kind of conversation? Or do you have that conversation? Is this where you bring in someone like yourself? You can fall on the sword and do the work for on behalf of the families to protect the business.

Bryan Clifton: So in those scenarios, there's two sides of it. One, we're making an assumption that the person in that 

position actually wants to be in that 

position. I see just as frequently that a person has been put in that spot because they felt like it was an obligation or a 

duty. They were not actually wanting that spot, but they were asked to do it, and they felt like they had no choice 

but to say yes.

So going back to if my, yes, if I can't say no to my Yes, doesn't mean anything either. There's an element of that. The other part is somebody who is actively campaigning to try to be in that position. 

That is always a red flag.

Anytime that someone is actively campaigning to be in a leadership role, especially if it comes with a substantial amount of money or a lifestyle shift 

for them, that does not mean they're immediately incompetent.

But it gives me a lot of concerns that I wanna do due diligence about. To be able to understand why are they so [00:20:00] interested in this position. 

So one thing that I've discovered is some people are driven out of a desire or a pursuit of prestige, 

the feeling of being important. 

So if I am ceo, if I'm president, if I'm in charge, I feel better about myself.

And I also like the perks that come along with it. I'm externally viewed by customers, by vendors, by other people in the community. As you are in charge, you're making big decisions. Other people are driven by, I want to actually create a team. I want to create an environment that people want to be a part of.

I want to work with people who are trying to create a better solution for us all. I am more interested in the motivating factors behind A C E O choice or a board member 

choice than I am about the actual choice itself.

Jeffrey Feldberg: Okay.

Bryan Clifton: Because what that person is driven by or is directed by, it will create a subculture within the company and the company will start to shift its actions to help reward or to help supplement that desire of that individual or a few key [00:21:00] people that are there.

Because if the drive is on prestige, we will do everything we can to make sure we keep this front up. will never show that we have any weakness. We will never look at anything else because we want to portray this image of we have everything together. We're a high-end firm, we're fill in the blank, whatever that might be.

And you may actually miss out on market shifts or opportunities because you feel like, well, that's beneath us. Or that's not something that I would want to do whenever that makes actually the best strategy for the business. So there's never a perfect fit 

for any leadership spot. There's always deficiencies.

There's always pros and cons that you can go and nitpick around. But I want to know, can a person in this role be able to deal with curve balls? Can they deal with ambiguity? Can they deal with uncertainty? Because being in a leadership position, especially in a family business, 

what you are saying is you are asking for more uncertainty, not less.

That's what the role requires. That's what it functions as because it's not just uncertainty about market, it's uncertainty about family dynamics, [00:22:00] because whatever that person's role is within the family, it has a different connotation whenever you may be the person who could fire certain family members from their livelihoods.

And what we haven't gotten into yet, The way that companies are structured legally. Is this managed by a trust? Is this managed by a board? Does the board have the ability to hire and fire the c E O? Does the trust give certain language or protections? Cause I've worked with clients where the trust says these family members are required to be employed by this company indefinitely.

Well, that's a very different context. If I, as a CEO, cannot. Fire or remove or transition somebody because the way that their trust is set up, it is a legal requirement, 

uh, For I, those are all different scenarios that I've ran across, and there is no one size fits all. And so I wanna understand how are these decisions made, because I can play almost any game, but I need to understand what the rules are, 

what are the rules, what are the context, and then who has certain advantages or [00:23:00] certain disadvantages because of how those rules have been structured or set in place.

Jeffrey Feldberg: What's interesting, Bryan, in that first scenario where it's all about prestige or ego or vanity, whatever you want to call it, fill in the blank, it really sounds like it's a situation. It's that old fable of the emperor with no clothes. That's what the organization ultimately becomes. And they're playing up to that because let's face it, the employees in the company, they're worried about their jobs.

I have to meet the rent or the mortgage, I have to put food on the table. And okay, this person wants prestige. If that's what it's about, that's what I'll give them. That's my job security. I'll go ahead and do that. So in those kinds of scenarios, Bryan, is there ever a situation where you're advising a family?

Listen, why not just cut a check to so-and-so? if you want a livelihood, if you want a lifestyle for someone, if the business can afford it, just cut a check and have professional management come in and just call it a day. And this way, Your sons, your daughters, your family. Your grandchildren, great-grandchildren.

They'll have that livelihood and they can figure out what they wanna do with their lives. Is that ever an option?

Bryan Clifton: Happens about two to three times a year with clients I work with. 

The absolute best thing for the [00:24:00] family is to not be working 

together and to have that separation because if the business truly is kind of the goose that's laying the golden egg, 

we don't wanna mess that up. And it is cheaper for the family and the business to pay an eternal 

severance or an annuity to that individual and to have them not involved, than to have them mess up everything else for hundreds, thousands of employees that may be connected to that.

Jeffrey Feldberg: And then Bryan on the flip side. So that takes care of perhaps not in the most humble of ways, but that takes care of the situation. Well, I want a lifestyle for my child or my grandchild or a family member, and this way we can do it without affecting the business. The one caveat being, obviously as long as the business is in a position to continue to write the check, things are good.

The flip side, someone who does have the right intention. Yeah. I want to take this to the next level. I want to build a team. I want to create a legacy for the company for the better, all the right reasons, but as terrific as a person, as he or she may be. They either don't have the experience, they don't have the skillset, they don't have the aptitude.

[00:25:00] How do you handle that kind of situation?

Bryan Clifton: So it depends on if they have a skillset that can be developed, 

or if they're aspiring for something that no matter how much they work is never going to be part of their competency or skillset. So you split it up and kind of do those two spots. If this is somebody that is just, they're green and they need some experience and some veteran assistance around 

them.

Let's figure a way to be able to do that on a set timeframe. So here's milestones, here's objectives. We need to see this progression this direction to be able to move up to this spot or within this context. 

And so that's where I go back to if I have three to five years with a family, to be able to work through.

Those scenarios are very common. We've got Johnny over here who's 26 and he just finished his MBA and he is really bright. He just doesn't have the real world experience that we would like. For this, can we help be able to get it? Because we want him to be the one in charge of this by the time he is 35, fill in the blank, whatever, number, 

age year, whatever that might be.

That is a different connotation than somebody who has [00:26:00] great desires, but that's just not who they are. 

That's not their wiring and no amount of support skillset is going to get them to that level. Those situations are probably the hardest ones that I deal with. 

Because there are times whenever you see the limitations of somebody's capabilities, and just because I may see that does not mean I'm a hundred percent right.

There have been people that I have thought that about that have surprised me on the positive side and on the negative side. But if we feel like that is a true limitation, how can we find the best fit for that individual and how can they be a contributor as part of a team instead of maybe being the one who is leading everything in that team?

Once again, we go back to the size of company. Some companies are so large, you can create many kind of fiefdoms divisions territories within it to where somebody might be good at leading a subset, but they're never gonna be good at leading the entirety 

of it. And so how do we find the best way for this to work?

Not only for the family but also the other people? Cuz every business, that's a family business, you're gonna have non-family [00:27:00] members working in it.

How do we find a way that's appropriate and right for them? Because I feel just as much of a responsibility to help take care of them and their families and their hard work as I do the core family or the core families who are put together.

Jeffrey Feldberg: Got it. Okay. And so in that kind of scenario, and actually in all the scenarios as I'm thinking through this, Bryan, and you can tell me if I'm on base or off base, these are at the best of times prickly conversations. These are not easy conversations. So I'm thinking of a listener out there who's saying, okay, Bryan, you sound pretty good, but you know, should I write the check to have someone like Bryan come in for the company?

I would think one of the biggest reasons, if you wanna keep your family intact, if you don't wanna be on the firing squad from some family members, that someone like yourself, you're the insulator. You're the outside party. You don't have to deal with those family dynamics at Thanksgiving or Christmas or whatever the family occasion may be.

You can be the bearer of bad news. Not the family or the family member. How much does that play into this equation?

Bryan Clifton: there's a [00:28:00] part of that. Every now and then I will get somebody who. A year into an engagement, we'll say, you know, we brought you in as an insurance policy. 

We brought you in so that we'd have somebody to be able to deflect two in case things did not go well. 

And my perspective on that is like, that's fine.

I like the reason why you brought me in is not as important to 

me as are you willing to actually har have the hard conversations necessary in order to move this along? So that's a very early qualifying question that I will ask of potential clients is I am never going to cause you unnecessary pain.

That is not my desire. I don't get joy outta causing unnecessary pain. But if we go through this, there will be hard conversations. There will be things that will be frustrating. There will be times where you are mad at me or you're mad at other people because we are bringing up topics that need to be discussed in order for it to have the framework necessary for this to be able to move forward.

If you're unwilling to do that work, bringing me in is not going to help. Because I can't force you to go there. I can create every scenario, every situation where it would be in your best interest to move [00:29:00] forward on that conversation, but I cannot force you into that 

and force everybody else. So I work a lot with families at the early stages of how do we create the trust and our dynamic so that, my desire is to help you collectively work together.

And I'm also always trying to work myself out of a job. 

If a family needs me 10 years after the fact, that is not a good setup. I want them to be able to have the competencies, them to be able to have the structures to be able to work together and not need a third party to come in. Now, there may be certain situations, there's certain issues that come up where I might need to be brought back in, but my desire is not to be working with a family for 20 years.

That's 

not a ideal scenario. It's how do I get you to where you're self-sufficient, 

To be able to do that.

Jeffrey Feldberg: It sounds like you're a lot like us here at Deep. Wealth. Our goal is effectively to fire ourselves, teach the fisher person how to fish. That they can do it on their own. And for the listeners out there who are either starting a business that may become a family business, or they're in a family business, perhaps you can shed some insight on this because I know oftentimes when I'm speaking with a family [00:30:00] business, there's almost a baked in assumption they've drunk the Kool-Aid that yes, this business is going to last forever and hopefully six, seven generations down the road, the business will still be around not taking into account that as you go from one generation to the next generation.

Exponentially, it's growing in terms of family members. So as an example, first generation, perhaps there were a family of the two parents and maybe two kids or three kids. Well, each of those kids, they have kids, and you see where this goes very quickly, mathematically, it almost becomes unsustainable unless it become a titan of business and they have thousands of employees and you can incorporate that.

How do you deal with that kind of scenario in terms of mindset when you're working with the family?

Bryan Clifton: Within family businesses, we do have this, I would call it a myth or a misconception that family businesses are meant to last for long periods of time. 

Most companies. Family, business or non-family businesses are not gonna make it past a 20, maybe [00:31:00] 25 year 

mark. Merger, acquisition closure, bankruptcy, something.

If you have a business that lasts 50 years, you are in the single digits of success rate by that metric. Just because a business lasts for a long period of time does not mean it was successful.

It may have been limping along and barely breaking even, 

For a number of years and it should have died years before.

So if our metric is we want to keep the business open at all costs, 

that metric can cause you to make unnecessary sacrifices and other things in order to be able to have that metric. Be successful, keeping a business alive to be able to pass down to future generations. I understand the sentiment and the desire, and if that truly is important to you, I'd love to be able to help make that happen.

But I am more interested in how do you pass down the values, the perspective, and the skillset, because sometimes the best thing for a family business is to inspire entrepreneurship in the next generation. For them to go start something rather than to [00:32:00] step in as managers of the existing enterprise or the existing.

Core piece. And so that's a spot where I want to understand from the grandparents, from the parents, what does success look like for you as it relates to your kids, your grandkids, and how they explore their ideas, their curiosities, because sometimes you can use the core family enterprise as a great launching pad for other endeavors that are in a similar vein in a, a vertical integration element.

Something along those lines. But it does not have to be directly tied to what that core legacy business may be.

Jeffrey Feldberg: So Bryan, let's talk about that because really, I love what I'm hearing you say, in essence, you're turning that family business, which sometimes when you think of a family business, yeah, they're kind of behind the times. They're old, they're stuck in how things it used to be, and you're turning it into an incubator.

We're family members. They can leverage the resources from the family business, go off and start their own businesses and see where that goes. Because I know what you and the team do, and we're talking about this [00:33:00] offline, you're really breaking the mold of people's beliefs out there of what a family business is and what family businesses should and shouldn't do.

So what are you guys doing out there? Where are you going? What are you seeing where most family businesses are saying, oh yeah, I can't do it. Not possible, or never even thought of that. What would that look like?

Bryan Clifton: So most of the time what I see is the whoever the founder or the current c e o president of a family business is, they are judging the next generation based on the criteria that they used. To become successful. 

And so they will look at it and say, well, I was able to do this because I worked hard in 1975 and I was able to build it to this, 

and I'm frustrated that you aren't working the same 

way in order to create this, or it's not the same type of dynamic whenever it is.

Different generations, different capital structures, different. Everything is a difference in that. And so the families that are able, especially the larger the family, 

the larger the family, the more you have to think about that core business as kind of an incubator, [00:34:00] because otherwise the business just functionally has to be fairly large to be able to create the employment opportunities with the skillsets, with the specialization for all of those family members to still be involved at some point.

Or you start taking a family member who is C 

position and put them into a role whenever you could have had an A plus player in that, but because they didn't have the right last name, they got bumped for 

this. And you start allowing mediocrity to exist because you're trying to maintain a belief that family working here is a high priority or is a high driver for this institution.

Jeffrey Feldberg: So Bryan, you can tell me if I am on base or off base with this because as we've been talking through this, what I'm hearing you say loud and clear, I really love your approach and it's more on what I would call mindset. You and your team, you have the ability through mindset to train the existing generation who's running the business.

Hey, don't assume anything. Let's take a look at what you have. Where's the business today? Who the family members are, [00:35:00] maybe some family members. You can act like an Inc. Incubator because they're really entrepreneurial. You don't wanna hold them back and tie them into the family business, and you can encourage them to create a market disruption in an entirely different area on their own and go do their own things.

Or maybe you now have the mindset, well, I know politically, or it's the right thing to do. Supposedly I should put my daughter-in-law, my son-in-law, in the business. But you know what? Let's just cut a check and we'll have a professional management team or a mindset of, Hey, you know what?

So and so still young, but wow, they have a lot of potential. This is exactly the kind of leadership that this company needs in the next decade or so. Let's begin to mentor that person. They have the aptitude, they have the background, the skillset and all those kinds of things. How am I doing with that? Is that more or less.

How you can come in and really make a difference.

Bryan Clifton: Yeah, it's definitely one way to come in and what I've actually done a few times is I have bought businesses from clients that had poor successor options where they may have had some of those pieces in place, so, But there was a void in top level leadership, or there was an issue that [00:36:00] made it to where staying entirely within the family was not in the best interest of that 

family.

So that was never part of my strategy or my team strategy. But we've now done that successfully three times to be able to come in and buy businesses from clients or to partner with them 

in the continued progress and succession of it. And it's been some of the most fun I've had working with clients because you're able to pull the.

Actual strengths of the individuals behind a shared vision and a shared perspective, especially whenever you have an industry that has a lot of a lot of institutional knowledge or a deep learning curve to be able to understand how that industry functions or that geographical area functions.

And so that's one of the parts that I really enjoy, is how can we find ways to be able to partner not just on most people look at scenarios and they feel like they have option A or option B. 

Whenever I work with clients, we've got 25 different

We've got a lot of different spots. Now, 15 of these may immediately be off the table because they just don't make sense.

But I want to lay out all of those options. And obviously the more family members, the more variables, the greater those [00:37:00] options become. But how can we find unique and creative ways to meet that end objective and not just feel like we have a hammer? So everything looks like a nail, but how do we find the solution that's best for the family, for the business, and.

Looking at bringing in external equity, selling the business, bringing in external management, developing internal management. All of those things need to be on the table for consideration so that we can make the best choice, because we actually considered all the options, not because we only looked at two, because we felt like those were the only two available.

Jeffrey Feldberg: And Bryan, when you're brought into a particular family business, as we like to say here at Deep Wealth, particularly with our nine-step roadmap, and you're thinking at one point having liquidity event, we always ask that rhetorical question, how can you master something you've never done before? And the answer is, well, of course you can't.

And if you try to, well, you're putting everything at risk, your financial freedom, your future, the business, all those other things. What's really nice, someone like yourself, you are across the country, really around the world in [00:38:00] different situations. That gives you the edge and you're seeing all kinds of different things and because that why perspective, you may see something that other people simply don't and you have that broad experience.

Bryan Clifton: Well, and it's so fun. I mean, we operate in Mexico, we operate in multiple other countries. And what I have noticed is a solution that I may offer to somebody in Ohio, for example, 

is not a. Good solution even for the same dynamics in another country because of the cultural norms 

or because of the legal limitations or because of different spots that are there.

And what I always tell people, especially whenever they're looking at a transition event, is think about the first time you bought a car. 

For the first time you bought a house. 

You didn't know what you didn't know. 

You probably got better with each successive purchase. Because you learn things from your previous interactions.

So if you're looking at selling a business or transitioning a business, how do we bring in expertise so that you don't make that same mistake that you may have bought the first time you bought a house for the first time you bought a car? I overpay it. I didn't ask these questions. I didn't, [00:39:00] I got too antsy and I didn't have the objective perspective that I want.

And so that's why I enjoy working with clients of. Selling or transitioning a business may be the largest financial event that you ever have in your life.

How do we make sure that you have the least amount of regret possible? 

And I'm always very honest to say you will have some level of regret. I have never met somebody who has sold a business that five years later says, I did it 100% exactly like I want.

There's always some point, or I wish I had done this or this could have been a little different. Same thing. It's the buyer's remorse. Those psychological pieces are true, but how can we have the least amount of regret? And especially as you have more people sitting around the table, 

how do we have the collective feeling of, I'm glad we did this.

This was a good decision, this is what we needed to do. And again, There is never a perfect time to sell a business. There's never a perfect time to be able to transition, but I use the analogy of a baton. 

[00:40:00] If I am trying to sell a business or pass it on to a future generation, there is a window in which somebody would be willing to hold or grab that baton from me.

If I am unable to make that handoff, that window may expire and there's no guarantee that it will ever come back around. 

And so I've worked with people who have made promises to employees or family members. I'm gonna step away in three years. 

In five years, three years comes, they're still there. Five years, they're still 

there.

After a while, that person, they stop showing up, they leave, they go to a different job. They go start a competitor because they do not believe you whenever you say that they could actually be a successor candidate. And I've had multiple clients that family members have 

left because granddad said, you're gonna take this over.

Eight years later, you're no closer to that than what it is. And it creates odd dynamics. And so if we're gonna look at a transition event, we have to understand there is a window, 

that window will expire, but that window of a successor may not line up with your window of how long you want to work or [00:41:00] how long you want to be in charge.

And so you can have a disconnect of those. So how do we find ways to be able to navigate that process?

Jeffrey Feldberg: And speaking of navigation, just before we go into wrap up mode, I'm wondering as we sit here today recording this conversation. Two significant things have happened and I've been asking these two questions. It's a bit of a theme going on out there with the guests always to hear their perspective. And so, as we sit here right now, thankfully the pandemic is well behind us, but it left its imprint on society.

Things are never the same and they forever changed. Some good, some perhaps not so good will leave the judgment off to the side. Things are just different. And then on top of that, Bryan ai, it's everywhere now. It started, many years ago, decades ago. And then really it seems out of nowhere, it's headlines and every day we're hearing something else.

And massive change is now coming because of ai. So from a family dynamic, a family business side of things, post C O I D, and now with AI upon us, how have things [00:42:00] changed or haven't they changed when we're running a family business?

Bryan Clifton: I have a unique perspective on this. About six years ago, I bought a technology company that was about two weeks away from bankruptcy. 

Now we're about 70 employees and we specialize in AI and machine learning working with large corporations, and I do not have any direct. All been in day-to-day operations.

I have great business partners that are there, but I love my conversations with them about where AI is 

and where it is progressing. Because hearing that from the developers, from the technologist perspective, they are always. Further along in the thought process of what it could do or what it is capable of than what I realized at the time.

And so within family dynamics, family relationships and the interpersonal emotional elements is not going to be replaced by AI 

because humans, we need a way to be able to interact with each other. AI is another tool that can be used for good. Can be used for bad, depending upon the company, the situation, the dynamic that you're in.

I view AI similar to how [00:43:00] people view the internet whenever it was first coming on the screen. It's like, well, I don't really know what this is. How can I use it? Where does it make sense? Ai, there's certain industries that it's deeply involved in right now and has ability to take your cost factor down by magnitudes to be able to make efficiency so much better.

Ai, the ability to put things through that code base or to be able to look at large data sets, to be able to find synergies or to be able to find common threads or to be able to find elements like that. For some industries, that's a legitimate game changer. It could replace positions. It can drastically reduce expenses, and so what I always encourage people with AI experiment.

Like find ways to be able to get comfortable with it. It's not going away, but how can you find a use case or a scenario where you can run an experiment in your company to be able to see, well, could this be helpful here? Is this worth it? Because it's probably gonna be clunky at first. 

I doubt that you're gonna have an AI deployment as a tool within your company and say, well, that just worked fantastic the first time.

It may, [00:44:00] but let's be realistic. So how can we find ways to be able to run experiments and not be scared of 

it, but utilize it Because it may be part of the innovation that we've talked about of where that business needs to go in order to be relevant for the next 10, 20, 30 years.

Jeffrey Feldberg: Some terrific insights on that and we'll have to see where that goes. we're saying here at Deep Wealth, really we feel we're in the golden era of ai. It's just starting right now, so we'll see where all that goes. Bryan, before we go into wrap up mode, I'm wondering are there. Perhaps topics that we didn't cover in our, what seems like a very short time together, although we've covered a lot.

Are there some things that we haven't covered? Is there a message or some insights that you'd like to get out there to the listeners?

Bryan Clifton: One of the biggest ones is just the, where the future of work is going. 

Hybrid work is here to 

stay. It is not going away. If you are in an industry or a business that still requires your employees to come into an office five days a week and you're looking at a generational 

transfer, you've already cut your pool of potential candidates so far down that your possibility of success is near impossible.

Now, I understand there are certain industries [00:45:00] that's required to have them there. 

Manufacturing companies machine shops, other things that are producing physical goods. That's different than if you're doing a knowledge work or something that can be done behind a screen. But if you're using that as a filtering tool to eliminate certain buyers or looking at that as they need to run the business the same way that you've operated it.

You have cut your pool of potential successors so far down that it's gonna make your process that may already be difficult, even more so, and it's probably going to leave you more frustrated than what you need to be.

Jeffrey Feldberg: Interesting. Well, thank you. Thank you for sharing that. And speaking of that, as we look forward, we look back. It's a perfect segue to the wrap up question, and I say this on every episode, but it's so true. I really have the privilege and the honor. To ask this question has become a tradition here. So Bryan, let me set this up for you.

It's a fun question. I'd like you to think about the movie Back to the Future. And in the movie you have that magical DeLorean car that can take you to any point in time. So I want you to imagine now it's tomorrow morning. And Bryan, this is the fun part. You look outside your window. Not only is DeLorean car there, [00:46:00] but the door is open, it's curbside, it's waiting for you to hop on in which you do.

You can now go to any point in your life, Bryan, as a young child, a teenager, whatever point in time that would be. So you do that, you go back in time. Bryan, what are you telling your younger self in terms of life lessons or life wisdom or, Hey Bryan, do this, but don't do that. What would that sound like?

Bryan Clifton: A great question. I would probably go back to. Whenever I'm 13, 14, 15, working deeply in our family business and ideally right before we had to declare bankruptcy, which was whenever I was a freshman in high school. And then I got the privilege, honor, responsibility, whatever you wanna call it, of leading my family's company through bankruptcy, 

Because my dad was not in the country at the time.

And I got to proceed through a lot of that. And in that moment, I felt the weight of the world. my shoulders, like I had to let go about 35 employees, some of which were parents of friends of mine. 

If there's one thing that's worse than getting fired, it's being fired by a 15 year old, 

Whenever you're an adult.

And I think it would go back to that time to be able to help [00:47:00] myself understand. How that experience would shape the way that I view risk 

and the way that I view how businesses operate. But more importantly, how I view people. 

As far, these are not widgets. These are not cogs in a system to be able to produce an output.

They have their own individual desires, demands hopes for their life, and how can I create structures that allow them to be able to do that? Because when you allow that for other people to be able to live their best version of your life you're able to create some amazing things beyond just from a profit standpoint, but from a a lifestyle and a enjoyment to be able to interact with people on a daily basis.

Jeffrey Feldberg: Wow, that is really insightful advice, and not just for your 15 year old, but really for all of us today, whether you're 15 or 150, everything else in between. So. that can take you places. Bryan, I really wanna thank you for your wisdom, your vulnerability, your insights. You really made a difference out there.

And as we say here at Deep Wealth, it's official. This episode is a wrap, and as always, may you [00:48:00] continue to thrive and prosper while you remain healthy and safe. Thank you so much, Bryan.

Bryan Clifton: Thank you very much. I've enjoyed it. 

Sharon S.: The Deep Wealth Experience was definitely a game-changer for me. 

Lyn M.: This course is one of the best investments you will ever make because you will get an ROI of a hundred times that. Anybody who doesn't go through it will lose millions. 

Kam H.: If you don't have time for this program, you'll never have time for a successful liquidity 

Sharon S.: It was the best value of any business course I've ever taken. The money was very well spent.

Lyn M.: Compared to when we first began, today I feel better prepared, but in some respects, may be less prepared, not because of the course, but because the course brought to light so many things that I thought we were on top of that we need to fix. 

Kam H.: I 100% believe there's never a great time for a business owner to allocate extra hours into his or her week or day. So it's an investment that will yield results today. I thought I will [00:49:00] reap the benefit of this program in three to five years down the road. But as soon as I stepped forward into the program, my mind changed immediately. 

Sharon S.: There was so much value in the experience that the time I invested paid back so much for the energy that was expended. 

Lyn M.: The Deep Wealth Experience compared to other programs is the top. What we learned is very practical. Sometimes you learn stuff that it's great to learn, but you never use it. The stuff we learned from Deep Wealth Experience, I believe it's going to benefit us a boatload.

Kam H.: I've done an executive MBA. I've worked for billion-dollar companies before. I've worked for smaller companies before I started my business. I've been running my business successfully now for getting close to a decade. We're on a growth trajectory. Reflecting back on the Deep Wealth, I knew less than 10% what I know now, maybe close to 1% even. 

Sharon S.: Hands down the best program in which I've ever participated. And we've done a lot of different things over the years. We've been in other mastermind groups, gone to [00:50:00] many seminars, workshops, conferences, retreats, read books. This was so different. I haven't had an experience that's anything close to this in all the years that we've been at this.

It's five-star, A-plus.

Kam H.: I would highly recommend it to any super busy business owner out there.

Deep Wealth is an accurate name for it. This program leads to deeper wealth and happier wealth, not just deeper wealth. I don't think there's a dollar value that could be associated with such an experience and knowledge that could be applied today and forever. 

Jeffrey Feldberg: Are you leaving millions on the table? 

Please visit www.deepwealth.com/success to learn more.

 If you're not on my email list, you'll want to be. Sign up at www.deepwealth.com/podcast. And if you enjoyed this episode, if it added value, if you walked away with some new insights and strategies, please leave a [00:51:00] review on your favorite podcast channel. Reviews help us reach new listeners, grow the show. And continue to create content that you'll enjoy and as we wrap up this episode as always please stay healthy and safe.