Building Wealth & Preparing Your Business for Sale | Dan Pascone with Chris Poff | Podcast #06

Posted on May 9, 2025 by Dan Pascone

Answer Box: TL;DR

Successful small business owners often don’t realize how fragile their “success” is until it’s time to exit. In this episode, Dan and longtime entrepreneur Chris Poff (founder of Wizard Brain Trust) dig into how Gen X and Boomer business owners can build real, transferable wealth by treating their company as an asset, not just a paycheck. Chris walks through his assessment-driven approach to preparing a business for sale, the three core reasons companies fail, why most owners are still “running it out of their back pocket,” and how to shore up foundations, funding, and management so you can scale, sell, or successfully pass the business on. They also explore the “perfect storm” facing small businesses—AI, tech, and mega-corps—and why asking for help and building a true “dream team” is now a non-negotiable.

Key Takeaways

Who Chris works with: His sweet spot is Gen X and Boomer business owners who’ve built something meaningful but are now facing aging, exit, succession, or “what’s next?” questions.
Two big exit paths: Most of his clients either want to sell the business for maximum value or pass it on to children without having the second generation blow the wealth.
Wizard Brain Trust model: It’s an advisory and education-first group. They start with: What’s your challenge? What lifestyle do you want? Are you living it now? From there, they educate instead of pitching products.
Always start with an assessment: Before talking AI, tech, or “growth,” Chris runs a full roadmap/assessment of the business: finances, systems, management, and the owner’s goals and lifestyle.
Three big failure drivers: In Chris’s view, businesses usually fail due to:
- Faulty business plan
- Inadequate funding
- Faulty or inadequate management team
He builds his assessments and plans around fixing those.
Foundation first: Before chasing funding or AI tools, he asks: Is your foundation rock solid? Are there “chinks in the armor” in planning, systems, or team that will scare lenders or buyers?
Custom to scale: A business doing $150k in revenue needs a very different plan than one doing $5M+. Chris tailors advice and funding options to current scale and budget.
Funding as a key challenge: Every growth stage requires capital—and most owners don’t know the funding options or how to present themselves to banks and lenders.
Get “funding ready” before asking: Owners who actually get the money have:
- Clean financials and systems
- A clear funding plan
- A credible story about how capital will be used
Only then does Chris send them to banks, lines of credit, or alternative funding (e.g., hard money, credit card stacking).
Back-pocket businesses: Many small businesses (even up to ~$1M+ revenue) started by talented tradespeople—like a great plumber—never formalize a real business plan, capitalization, or management structure. They’re just trading hours for dollars.
Your business is a baby: Chris tells owners to treat their business like a separate “baby” you must feed first. If every dollar goes to toys (cars, second homes), the business can’t grow into a real, salable asset.
Why great referral partners matter: Chris maintains at least two trusted pros in each role (PE, legal, accounting, finance, tech, VAs). He only refers to “A-players” because it reflects directly on him and on the client’s outcome.
Perfect storm for small business: He believes we’re in a “catastrophic perfect storm” for small business: mega-corps + AI + expensive tech stacks vs. small operators with limited capital.
AI & tech as a dividing line: “Embracing AI and tech” might cost a small business $5K–$30K, while mega-corps can drop millions. Competing now means smarter, not just harder, with tools you can actually afford.
Digitizing legacy businesses: There’s a major opportunity for buyers to purchase solid, blue-collar Boomer businesses (good brand/cash flow) and then digitize and modernize them.
Chris’s biggest personal lesson: He learned (starting around age 30) that “you can’t do it all yourself.” Arrogance is expensive; humility and asking for help are critical.
Value of complementary partners: He describes partnering with a “crusty old British accountant” who balanced his visionary, people-focused style with strict numbers and controls.
Productivity & mindset – quantum leaping: Chris is big on “quantum leaping/manifesting”—aligning your lifestyle, gratitude, and actions with the future you want so opportunities show up faster.
2 a.m. ideas: He jokes that he’s routinely woken up at 2:00 a.m. with floods of ideas and solutions—what he sees as Spirit/God/the cosmos pushing him to act.
Bucket-list win: At age 20 he wrote that by 30 he’d raise money for a Human Performance Institute. At 29, he realized he hadn’t started, assembled a team, asked for help, and within 90 days had almost $2M raised from a single investor and opened the facility.
Next milestone: He’s already “done” the millionaire thing; the next ambition is building to billionaire status—not as a money obsession, but as proof of what’s possible with the right team, goal, and plan.
Advice to younger self: “Ask for help. Humble yourself.” Many business owners are too proud or stubborn to get the guidance they need.

Key Moments

00:02 – Sponsor intro. Tailored Wealth is introduced as helping business leaders live their version of a rich life.
00:02–00:34 – Show framing. Dan positions the podcast as a way to cut financial noise and help leaders make smart, confident money decisions.
00:34–00:59 – Meet the guest. Dan introduces Chris Poff, founder of Wizard Brain Trust, with a background in real estate, entrepreneurship, and small business development.
00:59–01:33 – Dan’s excitement. Dan previews that they’ll touch on both personal finances and entrepreneurship—two topics he’s passionate about.
01:33–02:34 – Chris’s 90-second origin story. Born in Ohio, diehard Buckeye, reading success books in 3rd grade, first business at 17, serial entrepreneur, and not born into money—dad was a salesman.
02:15–02:34 – Real estate & Wizard Brain Trust. His advisory business grew as an offshoot of his real estate company after repeatedly running into small business owners needing help starting or building wealth.
02:34–03:08 – Wizard Brain Trust philosophy. It’s an advisory group that leads with education, not selling—asking about challenges, lifestyle goals, and then teaching what’s next.
03:08–03:39 – Ideal client profile. Chris mainly serves Gen Xers and Boomers who are now thinking about exit, cash-out, or succession to kids.
03:39–03:58 – Exit realities. He notes the huge difference between how a business “looks” now vs. what buyers will pay—and the need to optimize valuation or build systems for a second generation.
03:58–04:25 – Tech & AI challenges. On top of exit planning, owners are stressed about IT and AI integration, which affects everyone, not just older generations.
04:25–05:22 – How he engages owners planning to sell. Step one is always an assessment/roadmap—not just P&Ls, but lifestyle satisfaction, systems, and operations behind the numbers.
05:22–05:51 – Three reasons businesses fail. Chris lays out his triad: faulty business plan, inadequate funding, or inadequate/faulty management team.
05:51–06:35 – Don’t chase the wrong problem. Even when owners think “AI/tech” is the main issue, he still runs the broad assessment—often discovering deeper issues like capitalization.
06:35–07:03 – Tailored to scale and budget. He contrasts the needs of a $150K gross business with a $5M business—same principles, very different budgets and tactics.
07:03–08:04 – Funding as a growth gate. Funding is a recurring challenge; owners often don’t understand that they need a plan and a solid foundation to be “worthy” of capital.
07:44–08:28 – Getting bank/credit-ready. Chris describes prepping a client for a line of credit by shoring up the business first so it looks strong to lenders.
08:04–08:28 – Different funding solutions by size. For a $150K gross business, options might be:
- Bank with an existing relationship
- Hard money lending
- Credit card stacking, etc.
08:51–09:47 – Back-pocket entrepreneurs. Chris explains how many small businesses (e.g., a skilled plumber) bootstrap, rely on friends/family, and hit six figures without ever creating a real business plan or structure.
09:47–10:19 – Trading hours vs. owning a business. Many are still just trading time for money, not building a system that can be sold or passed on.
10:02–10:19 – The “business is a baby” metaphor. He tells owners their business is another baby—you have to feed it first so it can grow; spending everything on lifestyle prevents real growth.
10:39–11:24 – Chris’s partner ecosystem. He keeps at least two pros in each key category: PE, legal, accounting, financial advisors, tech, VAs, etc., constantly hunting for A-players.
11:24–12:07 – Only A-players on the team. Chris refuses to “play referral musical chairs”—if he sends a client to someone, he wants to know they’ll be taken care of because it reflects on him.
12:07–12:33 – Dan’s “quarterback” analogy. Dan relates, describing how his firm acts as a financial quarterback coordinating other professionals, and the importance of vetting those partners.
12:33–13:17 – Where small business is headed. Chris calls the current environment a “catastrophic perfect storm” for small business: mega-corps vs. small operators in a hyper-tech, AI-driven world.
13:17–14:14 – David vs. Goliath in AI spend. He compares a small business needing $5K–$30K to embrace AI/tech vs. mega-corps dropping millions—a massive disparity in tools and reach.
14:14–14:40 – AI + tech as bigger than the industrial revolution. In his view, the combined impact of AI and tech may be more drastic than the industrial revolution for how we live and work.
14:40–15:24 – Sometimes “cash out” is the right move. For some Xers/Boomers who don’t want to fight tech wars, his advice is: get your valuation up and exit well.
15:24–16:24 – Opportunity in Boomer exits. Dan brings up another guest who buys blue-collar businesses from retiring Boomers and modernizes them—a big opportunity for the next generation.
16:24–17:17 – Personal challenge: you can’t do it all. Chris shares his recurring life lesson: starting at age 30, he realized he needed help and couldn’t keep trying to do everything alone.
17:17–17:37 – Complementary partners. He describes his past partner, a “crusty old British accountant,” who balanced Chris’s visionary, people-oriented strengths with hard numbers and controls.
17:37–18:09 – The myth of DIY everything. When small business owners say, “I’ll just learn it on the internet,” Chris calls that out as unrealistic for serious growth and complex next steps.
18:09–18:24 – Lightning round intro. Dan transitions into the fast-paced lightning round.
18:38–18:54 – Coffee or tea? Cats or dogs? Chris picks coffee and dogs.
18:54–19:16 – Favorite tech tool. Beyond computer/phone, he says he can’t live without an autoresponder/CRM.
19:16–19:38 – Favorite quote. Chris cites a quote often attributed to Mark Twain/Samuel Clemens: “The two most important days in your life are the day you were born and the day you find out why.”
19:38–20:11 – Favorite business/finance book. He points to classics like Think and Grow Rich (Napoleon Hill) and Rich Dad, Poor Dad, noting that newer “quantum leaping” ideas are often rebrands of these fundamentals.
20:11–21:19 – Productivity hack: quantum leaping & gratitude. Chris talks about aligning your life, gratitude, and goals (what some now call “quantum leaping”), and how that fuels productivity and faster progress.
21:19–21:37 – 2 a.m. wakeups. He describes being awakened at 2:00 a.m. with ideas and challenges to solve and believes that’s Spirit/God/cosmos pushing him to move.
21:37–22:17 – Bucket-list achievement: Human Performance Institute. At 20 he wrote a goal to build a high-tech Human Performance Institute by age 30. At 29 he realized he was behind, assembled a team, and within 90 days raised nearly $2M, opening the facility in Cincinnati.
22:17–23:16 – Early “t-shirt” moments. He views that experience as an early “been there, done that” moment that proved quantum leaping and the power of asking for help.
23:16–23:54 – Next financial milestone. He’s now aiming for billionaire status, not out of greed but to demonstrate what’s possible with the right team and mindset.
23:54–24:11 – Advice to younger self. Chris would tell younger Chris: “Ask for help. Humble yourself.”
24:11–24:51 – How to connect with Chris. He shares his website buildingbusinesswu.com and notes he’s reachable by text/phone/email; Dan promises to put details in the show notes.
24:51–25:07 – Dan’s close. Dan thanks Chris, wraps the episode, and reminds listeners that the show is about learning to improve your wealth and your life.

Episode Summary

In this episode of Making Sense of Your Money, Dan sits down with serial entrepreneur and advisor Chris Poff, founder of Wizard Brain Trust, to explore how business owners—especially Gen Xers and Boomers—can turn the company they’ve built into lasting, transferable wealth.

Chris’s entrepreneurial streak started early: he was reading success books in third grade and launched his first business at 17. He wasn’t born into wealth (his dad was a salesman), but over decades of starting, buying, and selling companies, he developed a pattern for what makes small businesses succeed or fail. Out of his real estate work, he kept meeting owners who wanted to start a business or unlock more wealth from the one they already had, which led him to create Wizard Brain Trust.

The Brain Trust is built on a simple but often-missed philosophy: educate first; sell later (if at all). Rather than pushing services, Chris begins every engagement with a detailed assessment—or “roadmap”—of where the owner and business actually are today. He asks about lifestyle satisfaction, long-term goals, key challenges, and then digs into the financials and systems behind them. In his experience, businesses tend to fail for three primary reasons: a faulty business plan, inadequate funding, or a weak management team. That triad becomes the lens through which he evaluates whether a company is ready to grow, sell, or be passed on.

Many of his clients are Gen X or Boomer owners facing the realities of aging and exit. Some want to cash out and sell, ideally at the highest valuation possible. Others dream of passing the business to their children without watching the second generation squander the wealth. In both cases, Chris emphasizes the same first step: build a rock-solid foundation. Clean numbers, robust systems, and a credible team are essential for either a strong sale price or a smooth succession.

Funding is a recurring theme. Chris notes that most owners only think about funding when they need it, but lenders and investors reward preparedness. Before approaching banks for a line of credit or exploring alternative financing, he works with clients to shore up their P&Ls, fix operational gaps, and craft a clear funding plan. Only then do they decide whether the right next steps are traditional banking relationships, hard money, credit card stacking, or something else—scaled appropriately for a $150K business vs. a $5M one.

At a deeper level, Chris calls out a common small-business trap: many operators are still running their business out of their back pocket. A talented plumber, for example, may quit a job, tap friends and family, and quickly get to six figures—but without a business plan, capitalization strategy, or team structure, they’re just trading hours for dollars. For owners dreaming of selling or retiring, that’s not enough. He urges them to view the business as a separate “baby” they must feed and grow before feeding lifestyle—otherwise, there’s nothing of substance to transfer or sell.

The conversation zooms out to the macro landscape. Chris believes we’re in a “catastrophic perfect storm” for small business: mega-corporations with huge budgets, rapid advances in AI and technology, and a widening gap between what big companies can spend on tools versus what small firms can afford. Embracing AI and tech might mean a $5,000–$30,000 investment for a small business, versus millions for a mega-corp. That disparity makes it harder but not impossible for small operators to compete; it just demands more strategic planning and focused use of limited resources.

Interestingly, that same environment creates opportunities. Dan mentions a prior guest who buys blue-collar Boomer businesses with strong brands and cash flow and then digitizes them. Chris agrees: for owners who don’t want to fight the tech war, a well-planned exit at a strong valuation may be the smartest move. For buyers, modernizing these legacy businesses can be a powerful wealth strategy.

On a personal level, Chris shares a major life lesson: starting around age 30, he realized how dangerous it is to believe you can do everything yourself. Overconfidence and DIY stubbornness are common among entrepreneurs, but they become liabilities as complexity grows. He talks about the value of partnering with complementary experts—like the “crusty old British accountant” who kept his big ideas grounded in financial reality—and urges owners to humble themselves and ask for help.

The lightning round reveals more about Chris’s mindset. He credits classic books like Think and Grow Rich and Rich Dad, Poor Dad for shaping his thinking, and he’s fascinated by what some now call “quantum leaping”—aligning your beliefs, gratitude, and daily actions to rapidly move toward your ideal lifestyle. He describes being routinely awakened at 2:00 a.m. with insights and challenges to solve, viewing that as a spiritual nudge to take action. One of his favorite achievements came at age 30, when he finally pursued a goal he’d written a decade earlier: building a high-tech Human Performance Institute. With only months to spare before his self-imposed deadline, he assembled a team, raised nearly $2M from a single investor in about 90 days, and opened the facility—an early proof to himself of what clear intention plus execution can do.

Today, Chris is aiming at his next big financial milestone—moving from millionaire to billionaire status—not out of obsession with money, but as a way to demonstrate what’s possible when you combine a compelling vision, a strong team, and disciplined planning. His advice to his younger self, and to listeners, is simple: ask for help and stay humble. In a world of rapid tech change, intense competition, and complex exit decisions, trying to figure it all out alone is a recipe for frustration, not freedom.

Full Transcript

Announcer: Brought to you by Tailored Wealth, helping business leaders live their version of a rich life.

Announcer: Welcome to another edition of the Making Sense of Your Money podcast, where we cut through the financial noise and help business leaders to make smart, confident money decisions.

Dan: All right, welcome to another episode of the Making Sense of Your Money podcast, where we help you take control of your finances, minimize uncertainty, and maximize wealth potential.

Dan: I’m your host, Dan Pasone. I’m the founder and CEO of Tailored Wealth. And I’m excited to have a special guest with us today.

Dan: I’ve got with me Chris Poff. Chris is the founder and creator of Wizard Brain Trust, which I’m excited to get into and talk a little bit about. But Chris has got some unique expertise both in the real estate industry as well as entrepreneurship and small business development.

Dan: So I think we’re going to get a chance to talk about a few topics, some related to personal finances, some related to entrepreneurship and business, which I’m very passionate about, all of the above.

Dan: So Chris, welcome to the Making Sense of Your Money podcast and we’re pumped to have you today.

Chris: Yeah, it’s great to be here. Good to see you.

Dan: Good, man. So we’ve got a lot to cover. We’re excited to chat with you. I think you’ve got some really interesting expertise, background, and experience that you can share with our audience.

Dan: So, before we get into it, why don’t you just give us a quick 90-second overview of who you are, what your business does, and how you ultimately got into this space.

Chris: Oh my God. Ninety seconds.

Dan: That’s it.

Chris: Well, I was born in Ohio, diehard Buckeye, and from an early age I just had a drive for success.

Chris: I was one of those weird kids—I started reading success books in the third grade.

Dan: Wow.

Chris: And did my first business at 17 and just fell into serial entrepreneurship. I loved starting businesses, learning about success, buying businesses, selling businesses, the whole bit.

Chris: I wasn’t born into money. My dad was a salesman and had a chance to have a business once I graduated from high school, so I got to participate in some of that, too.

Chris: But the business that I created was an offshoot of my real estate company, because I kept running into small businesses either wanting to start up or wanting to create more wealth. And there seemed to be a formula that I found that worked really well, and it’s called the Wizard Brain Trust.

Chris: It’s an advisory group where we educate first. A lot of people come in and start selling first—we don’t do that. We find out, “Hey, what’s the challenge? What’s going on? What would you like to see done differently? What kind of lifestyle do you want to live and are you living that?”

Chris: And then we educate—that’s the first thing we do. A lot of people just launch into selling, but we launch into educating what’s next for that person.

Chris: So that’s as close to 90 seconds as I can go.

Dan: That’s it. Well done, Chris. Well done, my friend. I’m sure there’s a lot more that we’ll unpack for sure, but thanks for the overview.

Dan: So Chris, tell us a little bit about your ideal client and what you ultimately help them to do.

Chris: My ideal client, although I’m not limited to this—I do a lot of work with Gen Xers and Boomers. And the reason for that is number one, I’m 103 years old, so I relate to them.

Chris: Gen Xers and Boomers have a very good history, colorful background—the entrepreneurs I deal with—but they’re dealing with some really interesting challenges right now, which is, “Hey, I’m getting older. I either need to cash out or I need to have an exit strategy of some sort, or a succession strategy. I want to pass it on to my kids.” There are all these issues.

Chris: And then what we find out is, before you get there—like, let’s say you want to sell a company—well, the valuation… and you know, because you and I plan on working on some of these deals together. There’s a huge difference in how your company is looking financially and how you can get the most amount of money if you want to cash out, or how do you get the systems together to pass it on to your kids so that the second generation wealth doesn’t blow it.

Chris: Those are some of the challenges. And there’s also the IT and the AI challenge that drives all of us—not just us Xers and Boomers, but drives everybody—crazy now.

Dan: Yeah. Really, really good stuff. There’s a lot there I could dig into.

Dan: Let’s specifically talk for a second about that client of yours that is looking to or planning for or has aspirations to sell their business, because we deal with a lot of folks in that space and financial planning, as you know, is really critical for folks that are in that position.

Dan: But tell us a little bit about what you do for that individual—that business owner, the business in general, maybe the person as well, because that’s really important—and then what you do to help them achieve their desired outcome.

Chris: Well, it always starts with the same thing: an assessment. Let’s figure out where you’re at right now. I call it a roadmap—let’s see where you are on the road to wealth or lifestyle, whatever you want to call it.

Chris: So we go across the board. We don’t just say, “Hey, send me your P&Ls, let’s look at that.” I ask a lot of questions: Are you happy with your lifestyle? Are you where you want to be?

Chris: We look at the P&Ls, but we also look at the systems behind the P&Ls because the three reasons why businesses fail are: faulty business plan, inadequate funding, or faulty/inadequate management team.

Chris: So we look across the board. Probably the first thing we look at is: Did you build a rock-solid foundation? Are there chinks in the armor? Do we need to shore that up?

Chris: That’s step one: let’s identify where we want to start. And a lot of times, somebody will come to me and say, “Well, right now my problem is AI and tech integration.” And we still do the same assessment because they may be looking at that problem, but we’ve got another serious problem with maybe funding or capitalization, or the business isn’t running quite the way it should, or the systems behind it.

Chris: According to what that person’s goal is, then we sort of plug in those missing pieces of the puzzle. And we do it in real time, real budget.

Chris: In other words, if I’m working with a small businessman who is doing $150,000 a year gross, that’s a different animal than the person that’s doing $5 million and wants to scale up from there.

Chris: So we have to start within the budgetary concerns of that particular individual. So it’s all custom-tailored.

Dan: Got it. Yeah. That makes a lot of sense.

Dan: So you mentioned the three things that keep businesses from being successful or ultimately make businesses fail. What are the successful businesses that you’re dealing with—the successful clients that you’re working with—what are the three biggest challenges that they face and what do you typically do to help them overcome those challenges?

Chris: One of them—well, let’s take funding as a big one because every time you go to grow, you have to… If your funding isn’t all in place and if you don’t understand it…

Chris: There are a lot of people that don’t understand the first step in funding, which is you have to have a plan according to where you are right now. So again, the average person hasn’t tapped into those resources of funding and doesn’t know all the different ways to get funded and to apply that to their business. So funding is one of them.

Chris: The ones that are successful that I know, there’s a formula. Let’s just use one guy I’m talking about. He’s going for a line of credit, and before he goes for that line of credit, we have to shore up everything in his business so he looks good to the banks or he looks good to the lenders.

Chris: That’s one of the main steps: the difference between the guy wanting money or the girl wanting money and the guy that gets the money is that they are rock solid. They have a foundation, and they did a funding plan before we ever got to applying to banks and things like that.

Chris: Once you’re rock solid and we have that whole thing put together, then you can go after what you want. And also, there are different levels that I’m going to plug in.

Chris: If somebody’s at $150,000 gross, his only choice may be going to his bank where he has a relationship, or he might have to go to hard money lending or credit card stacking or whatever. It’s different for each person.

Chris: But yeah, the success is: did they listen to an expert like you or like me who has been there and done that to help them be worthy of funding?

Dan: Yeah, makes sense. Makes sense. Good stuff there. And yeah, the funding is certainly a challenge for business owners, there’s no doubt about it.

Dan: Let’s talk a little bit about the industry. Let’s talk a little bit about small business owners in general. Would you say funding is the biggest problem that you see in the overall field, or are there others that are big challenges?

Chris: Well, there’s probably three or four. Really with a small business person—and again, this is sort of sad to say—but a lot of small businesses started up out of their back pocket. They bootstrapped.

Chris: Let’s just use an example of a plumber who’s a really good plumber. He learned the trade from his boss, who he’s been with for five years. And now they’re sick and tired of making a wage; they want to own their own business.

Chris: So they start out and they’ve got a list of friends and family, sphere of influence, and all of a sudden they’re up and running making 50, 80, 100 grand a year, but they’re running that business out of their back pocket. They didn’t do a business plan. They didn’t do any of the steps. They didn’t look at their management team, all that stuff.

Chris: Again, if they didn’t build that rock-solid foundation, the small businesses I run into—even up in the million-dollar range gross—a lot of them didn’t understand the difference between… They’re still trading hours for dollars and they aren’t actually running a business.

Chris: So if they want to pass it on to their kids or something, we have to look at the whole structure of the business and say, “Okay, get the accountant involved,” and say, “Now you’re making money, but it’s all going to your Maserati and your second house and things like that.”

Chris: It’s not a true business. I always tell people: your business is another baby. You just had a baby. You’ve got to feed that baby first, and you’ve got to make sure that baby’s got all the foundation to grow. If you take that food away from the baby, the baby isn’t going to be solid; they’re not going to grow.

Chris: That’s one of the biggest things I see with small business: wrapping their mind around the fact that, “Okay, do I want to run a business or do I want to continue to grow something that I run out of my back pocket?”

Dan: Got it. Got it.

Dan: All right. So that’s some really good insights there, Chris, on your client and what you help them to do.

Dan: Let’s talk a little bit about partners, whether it be referral partners or partners in other aspects for you. What types of individuals or businesses do you partner with, and why would a potential referral partner want to work with you?

Dan: We certainly deal with a lot of folks in different aspects of business who are on and listen to this podcast. So tell us a little bit about that aspect of your business.

Chris: Well, I’m constantly searching—and I’m sure you are too—because I have at least two on my team of all the PEs: legal, accounting, the financial people like yourself, all the background like virtual assistants, the tech people (which keep growing and growing).

Chris: So I always have at least two of everybody. It is almost across the board; if you think of what it takes to run a business, I’m looking for those people.

Chris: But I’m not looking for, “Oh, you want to be on my team? Yeah, just send me your details.” I want somebody that—well, like you and I have talked—if I call you up and I send you a client, I want to know they’re taken care of.

Chris: I’m the old-school guy that I’m not just playing referral, you know, whatever you want to call it—musical chairs or whatever. I’m like, I’ve got this rock-solid team and I’m constantly looking for people that are real A-players or dream-team type players, because it comes back on me and ultimately we’re trying to get somebody to launch to the next level of lifestyle and business.

Chris: So I don’t want any excuses. I want people who are just like me—that if I say I’m going to do something, I do it.

Dan: Yeah, well said. I couldn’t agree more.

Dan: That’s a great point. Vetting partners is not an easy thing to do because it takes time, it takes experience, it takes talking to a lot of folks and finding the right people for you and for your clients, right? You want to have a rock-solid team that’s perfectly set up to serve your clients.

Dan: And that ultimately, I’ve always found, helps you to create that comprehensive offering—because whether it’s business development or how to grow or sell my small business, or wealth management (so I’m talking about your business and my business now), folks prefer to work through one source.

Dan: So I like that we’re kind of the quarterback for your financial situation. We’ll get the other players involved as needed and we can spearhead that. So it sounds like you’ve taken a similar approach, which is cool.

Chris: Yes.

Dan: Chris, where do you see small business going in the next five to ten years, and what are you doing to stay on top?

Dan: We probably need three or four hours to talk about that, but I’ll try to be short.

Chris: There is a—this is personal opinion. I’m 103 years old, so I’ve been up and down and seen the wars and all that stuff. I have more than one t-shirt from the been-there-done-that club.

Chris: We are in what I would call a catastrophic perfect storm for small business. What I mean by that is: look at how we’re based. We are a free enterprise, almost unfettered free enterprise system or capitalistic system that is nearing… what do I want to say? It’s nearing the end times in terms of there being mega-corps and then a bunch of small corporations struggling to survive.

Chris: The mega-corps have the huge budgets. With this AI—for a small business person, let’s just say for a small business person—AI could be $5,000 to $30,000 to embrace. Here’s this small business embracing this, and here’s the mega-corp throwing a million or $5 million at it.

Chris: So there’s such a huge disparity in the ability to compete with a good idea or good service or whatever. That whole definition has changed. It’s not that it can’t be done, but it’s much more challenging.

Chris: With tech, my feeling is—and we haven’t talked about this—but my feeling is this, combined with AI, is changing the world probably more drastically than the industrial revolution.

Dan: Yeah.

Chris: So people that are hiding their heads in the sand—especially the Gen Xers and the Boomers—I’m like, “Well, tell me where you’re at, because maybe you just want to cash out. Let’s get your business to its highest valuation, because this is a war.”

Chris: It’s a war, and it’s a war not only between high-tech and low-tech, or old school versus new school, but it’s also the moneyed corporations—the huge mega-corporations—versus when a small business comes to me and says, “I want to grow,” we have to figure out: how do you grow with the tools and the budget you have right now and go up against these guys with multi-million-dollar budgets for marketing or multi-million-dollar budgets for IT?

Chris: So yeah, that’s what I see as a huge challenge.

Dan: Yeah, it’s happening so fast. And to your point, having dollars and expertise gets you so much advantage compared to those that don’t have that.

Dan: So it’s interesting that you have folks that maybe don’t want to play in that game and you’re actually advising, “You know what? Let’s get you ready and prepared to sell.”

Dan: It’s funny, I had a guy named Brandon on our podcast show yesterday, and he invests in and buys more blue-collar small businesses. One of the opportunities that we talked about was that a lot of these Baby Boomer generations are looking to sell their business and retire.

Dan: And there’s such an opportunity for someone to come in and digitize the business and take what’s a really strong brand and maybe strong cash flow, but then expand that through the use of a lot of the tools that you referenced.

Chris: Exactly. Yeah, it’s a very exciting time, but a very challenging time if you don’t embrace the changes quickly.

Dan: For sure. For sure.

Dan: All right, Chris, good stuff there. We’re going to shift gears a little bit and talk a little bit about you now.

Dan: So tell us, if you don’t mind, a challenge that you faced to this point in your life and how maybe that’s helped shape the way that you do business.

Chris: Probably one of the biggest challenges—and it’s been gradual, well, it started at age 30 but it’s continual—is that I can’t do it all myself.

Chris: At 30 I was arrogant. I just thought I knew everything. Every decade you realize how much you don’t know and how much you need to humble yourself and ask for help because you just can’t do it all, especially now with high-tech.

Chris: So that’s been a constant struggle or a constant embracing that and saying, even when I made money, lost money—even when I was at the peak making a lot of money and huge net worth and all that stuff—it was still the same thing. If I got too arrogant, I had to humble myself and say, “You know what, I really don’t know it all and I need to plug in those pieces.”

Chris: One of the partners I had was a crusty old British accountant. He would balance me out because I’m the guy that wants to go out there and meet people and have all these creative ideas and help people grow their business or acquire more real estate.

Chris: He was the guy back there with the numbers, but I needed that. I can’t do it all myself. So that’s been the huge epiphany in my life: you’re not an island and you’ve got to ask for help. Nowadays, if you don’t, I don’t know how…

Chris: Small businesses come to me and say, “Well, I’m going to do it all myself. Okay, well, now that you’ve told me what I need to do, I’ll go learn how to do it on the internet.” No, it’s not going to work. You can do AI all day long, but it’s not going to teach you how to do that next step. The guy that’s been there and done that can do it so much quicker.

Dan: For sure. And there’s so much value in being able to collaborate and learn from that guy that’s been there, done that. Very cool. Very cool.

Dan: All right, Chris, now we’re going to transition into what’s become sort of a famous part of our show, and that’s the lightning round.

Dan: So the lightning round—I never tell the guests about it ahead of time. Anyone that listens to our show knows this is not premeditated.

Dan: I’m just going to give you a question. Some of them are going to be quick one-word answers. Some of them will require a little bit more explanation, but I want you to come back with the first thing that pops in your mind.

Dan: All right: coffee or tea?

Chris: Coffee.

Dan: Cats or dogs?

Chris: Dogs.

Dan: What’s one tool—we were talking about technology earlier—what’s one tool or piece of technology, other than your computer or your phone, that you can’t live without? It could be software, could be a product, anything.

Chris: Other than my computer or my phone? Well, you can’t live without, you know, an autoresponder, CRM.

Dan: Got it. Got it. Like it.

Dan: Give us a quote or a phrase about money or success that you really enjoy.

Chris: I could go on all day on this. I think it was Samuel Clemens who said, “The two most important days of your life are the day that you were born and the day you figure out why.”

Dan: Okay. I love that. I love that. Very good. The power of why.

Dan: Do you have a favorite book on finance or business?

Chris: Oh, jeez. Again, we could talk for hours. God, there are so many good ones.

Chris: Finance and business—I would still go back to some of the old classics. Napoleon Hill, Think and Grow Rich.

Dan: Yep. That one’s come up a bunch of times on our show.

Chris: Yeah. And the thing is, you know, now we’re talking quantum leaping. You and I, I think, talked a little bit about quantum jumping, quantum leaping—there are all these new buzzwords out there. There’s nothing new under the sun.

Chris: Napoleon Hill talked about it as manifesting your dreams, or “whatever the mind can believe, it can achieve,” and blah blah blah. So yeah, I start with those, but there are a million after that. Rich Dad, Poor Dad, you know, there are all these books you can read that give you great insight, but again, they’re just part of your toolkit.

Dan: Very cool. Very cool. Love it.

Dan: Do you have a personal productivity or finance hack—like a best practice, a shortcut—that you could share with the group?

Chris: Productivity. Yeah. This relates to quantum leaping.

Chris: One of the most powerful modules I teach is quantum leaping. Call it the new buzzword; it’s manifesting your dreams.

Chris: When you tap into and align yourself—and what I mean by that is not focusing on money, but focusing on your lifestyle and happiness and being congruent with everything you’re doing in your life—and then you become thankful for where you’re at and be thankful that you’re living your life the way you want to, what happens is when you do that, your productivity…

Chris: I’ll give you a good example. I’m awakened by—doesn’t matter what religion you are; you can call it Spirit, the cosmos, God—I usually get awakened at 2:00 a.m. every day.

Dan: Okay.

Chris: And I get all the challenges and stuff. I’m going, “This is a flood of information that comes in,” and I cannot sleep. It will not let me sleep.

Chris: So in terms of productivity: number one, be thankful for whatever’s in front of you—good, bad, or ugly—because you’re going to learn from it and you’re either going to come out of it better or you’re going to be stuck there.

Chris: You know, you get knocked down—it’s not a failure until you don’t get back up.

Dan: Love that. Love that. I’ve witnessed a couple of things you mentioned in my own life, so I can certainly relate.

Dan: What’s one bucket-list item for you that you’ve already accomplished?

Chris: Wow. This happened when I was 30, and I do a story on it or a module.

Chris: At age 20, in my… at Ohio State, all these success books came together and I said, “Okay, so here’s what I’m going to do: I want to become one of the world’s—or the local area’s—leading authorities on health and fitness and exercise phys and sports performance. I’m going to have my own Human Performance Institute, a facility that trains athletes, assesses athletes.”

Chris: You know, you’ve seen on the news where they’re testing an Olympic athlete—well, that’s what I put together. And I did that at age 20. I said, “By age 30, I will have my own; I’ll have raised at least half a million dollars for it.”

Chris: So a few months before my 30th birthday, I looked at all my little “I’m going to do this, I’m going to do that” on my bucket list and I said, “Oh my God, I’m no closer to that.”

Chris: So I put together a team—a sports medicine administrator, a hospital administrator—asked for help, and started going out to raise money. Within 90 days of my 30th birthday, I had the money raised. It was almost $2 million, which in today’s terms is probably $20 million, from a single investor.

Chris: And I did that only because I willed it, only because I quantum leaped. I said, “I can do this,” and I asked for help. And then I did it.

Chris: So that year, my 30th birthday, I opened up the Human Performance Institute up in Cincinnati. It was one of the first privately funded, high-tech, medically based facilities that did testing on athletes and executives.

Dan: Very cool.

Chris: So I don’t have to live some of that stuff later on. I sort of got that t-shirt early.

Dan: Good for you. Good for you. Really cool accomplishment. Great story.

Dan: What’s one financial milestone that you’re still working towards?

Chris: Okay, so… billionaire. Been there and done the millionaire thing, but… and I don’t want to say that—that sounds arrogant, and it also sounds like I’m focused on money. I’m not. But you asked.

Chris: The next step is, okay, anybody can do this if they’re willing to pay the price and embrace what it takes to get to that next level. I don’t believe that stuff about just being born into money. I think that gives you a hell of a leg up, but anybody can do it. You just gotta put the team together and have the goal and the plan.

Dan: I love that.

Dan: If you could give one piece of advice to your younger self, what would it be? I feel like you’ve given us like five of them already today, but let’s pick one.

Chris: Ask for help. Humble yourself.

Dan: Okay. Love that. Love that.

Chris: As a small business owner, a lot of us are arrogant and think we know everything.

Dan: Yeah, for sure. For sure.

Dan: All right. Well done, Chris. That was great. I loved it. I loved it.

Dan: Finally, if our listeners want to connect with you—whether it be to learn about your services or what you do, maybe collaborate, maybe they have referral opportunities or just ultimately work with you—what’s the best way to connect with you?

Chris: I’m old school. I’m on the internet. My website is called buildingbusinesswu.com. I don’t know whether you post that or whatever.

Dan: I’ll put that in the show notes. I absolutely will.

Chris: And you can text or phone me or email me.

Dan: Very cool. We’ll put Chris’s contact information in the show notes.

Dan: Chris, awesome, awesome stuff. Thanks for joining us and sharing your insights today. Really enjoyed the discussion. I know I learned a lot; I’m sure that our audience did too.

Dan: And this has been another episode of the Making Sense of Your Money podcast. We appreciate you all tuning in and learning ways that you can improve your wealth and improve your life. Cheers.

Resources & Citations

Wizard Brain Trust / Building Business Wu: Chris’s advisory platform focused on education-first strategy for small business owners (see buildingbusinesswu.com as mentioned in the episode).
Classic business/finance books:
- Think and Grow Rich by Napoleon Hill
- Rich Dad, Poor Dad by Robert Kiyosaki
Human Performance Institutes: For listeners interested in high-performance training models similar to what Chris built in Cincinnati.
AI & tech for small business: Tools like CRMs, marketing automation, and AI assistants that can be scaled to smaller budgets.
Tailored Wealth: Dan’s firm, focused on helping business owners and professionals integrate business outcomes with personal wealth planning.

FAQs

Who does Chris primarily work with?

Chris focuses mostly on Gen X and Boomer business owners who have built a business and are now asking, “What’s next?”—whether that’s selling for maximum value, scaling, or passing it to their kids. That said, his principles can apply to owners at many stages.

What is Wizard Brain Trust?

Wizard Brain Trust is an education-first advisory group created by Chris. Instead of leading with “what to buy,” they start with an in-depth assessment of your current business and lifestyle and then educate you on the best next steps for your goals, funding, systems, and exit/succession planning.

Why is an assessment so important before selling a business?

Because most owners have blind spots. An assessment reveals:

Whether your business plan, funding, and management team are strong enough.
Where the systems behind your financials are weak.
How attractive (or not) your business will look to buyers, banks, and successors.

Fixing foundational issues can materially increase valuation and reduce deal risk.

What are the most common reasons small businesses struggle or fail?

Chris points to three big ones:

Faulty or nonexistent business plan
Inadequate funding or capitalization
Weak or incomplete management team

Many owners are still “running things out of their back pocket” instead of treating the business as a structured, separate asset.

How can a small business compete with mega-corporations in an AI-driven world?

You can’t outspend them—but you don’t have to. Focus on:

Building a rock-solid, niche-focused foundation
Using right-sized tech and AI tools that actually fit your budget
Creating personalized, high-touch experiences big companies struggle to match
Working with advisors who help you prioritize the few moves that matter most

For some, the smartest option might be preparing for a well-structured exit rather than fighting every tech battle.

Can any business owner become a millionaire or billionaire?

Chris believes that anyone willing to pay the price—in focus, humility, team-building, and consistent work—can dramatically increase their wealth, regardless of where they start. Being born into money helps, but it isn’t a prerequisite. The key is having a clear goal, a realistic plan, and the right people around you.

How can I connect with Chris?

Chris shared that he’s “old school” but online. You can:

Visit his site: buildingbusinesswu.com
Reach out via text, phone, or email (details provided in the podcast show notes)

Disclaimer

This episode and written summary are for educational and informational purposes only. They do not constitute financial, legal, tax, or investment advice and do not create a client relationship with Tailored Wealth, Wizard Brain Trust, or any other entity mentioned.

Business planning, exits, funding decisions, and wealth strategies involve substantial risk and depend heavily on your unique circumstances. Before making any major decision—such as selling your business, taking on debt, implementing new technology, or changing your investment strategy—consult directly with qualified professionals (including financial advisors, CPAs, attorneys, and other relevant specialists) who can evaluate your specific situation and applicable laws.

Next Steps

If you’re a business owner and this episode hit home, consider:

Step 1 – Assess your reality: Write down your:
- Current revenue and profit
- Personal lifestyle goals
- Desired exit/succession timeline
Step 2 – Map your foundation: Ask:
- Do I have a clear, written business plan?
- Is my funding/capitalization appropriate for my growth goals?
- Do I have the right management team in place—or am I still doing everything myself?
Step 3 – Treat your business as an asset: Start “feeding the baby” first: ensure your business has the systems, reserves, and investments it needs before upgrading lifestyle.
Step 4 – Build your advisor bench: Identify at least one (ideally two) trusted professionals in each key area: finance/wealth, accounting/tax, legal, tech/AI, operations, and marketing.
Step 5 – Explore your exit or growth path:
- If you want to grow, map out the funding and systems needed.
- If you want to exit, begin now to clean up financials, shore up processes, and improve valuation.

To connect your business strategy with your personal wealth plan, explore more episodes of Making Sense of Your Money or reach out to Tailored Wealth for a conversation about your unique situation.