---
title: "Building Wealth & Preparing Your Business for Sale | Dan Pascone with Chris Poff | Podcast #06"
description: "Successful small business owners often don't realize how fragile their success is until it's time to exit. Dan and entrepreneur Chris Poff of Wizard Brain Trust dig into how Gen X and Boomer owners can build real, transferable wealth by treating their company as an asset—not just a paycheck."
url: "https://yourtailoredwealth.com/podcasts/chris-poff"
lang: "en"
published: "2025-03-14T00:00:00+00:00"
modified: "2026-10-12T14:48:30+00:00"
author: "Dan Pascone"
---

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



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## TL;DR

**Chris Poff says many small business owners don't see how much their success depends on the foundation behind the numbers until they're ready to exit, and that how a company looks financially and operationally can make a big difference in what an owner can get when they cash out.** In this episode, Chris, founder of Wizard Brain Trust, shares how he helps Gen X and Boomer owners think through funding, systems, exit and succession.

We cover his education-first approach, the 3 reasons he says businesses fail, why funding takes a plan, how small businesses can compete with mega-corporations in an AI-driven market, and the lesson that shaped him: you can't do it all yourself. A lightning round closes it out. Chris's views are his own, and this is general education, not legal, tax or business advice.

## Who Is Chris Poff?

Chris Poff is the founder and creator of Wizard Brain Trust, an advisory group for small business owners. He has a background in real estate, entrepreneurship and small business development. He grew up in Ohio and describes himself as a diehard Buckeye with a drive for success from an early age. He started reading success books in the third grade, started his first business at 17 and fell into serial entrepreneurship: starting, buying and selling businesses.

He wasn't born into money. His father was a salesman. Wizard Brain Trust grew out of his real estate company, because he kept running into small businesses that either wanted to start up or wanted to create more wealth. He found a formula that worked, and he built the group around it.

## Educate First

Chris describes Wizard Brain Trust as an advisory group where the first thing they do is educate. Many people launch into selling right away. His team starts by asking about the challenge: what's going on, what the owner would like to see done differently, what kind of lifestyle they want and whether they're living it. Then they educate on what's next for that person.

We run our own business on a similar idea, which is why this conversation clicked.

## Who He Works With

Chris isn't limited to one group, but he does a lot of work with Gen X and Boomer entrepreneurs. Many are facing questions like: I'm getting older, so do I cash out, build an exit strategy, or pass the business to my kids?

He told us that before you get there, there's a big difference between how your company looks financially and how much you can get if you want to cash out. There's also the question of putting systems in place so a business can pass to the next generation without the second generation blowing it. We cover that side in [Legacy Is Built, Not Inherited.](https://yourtailoredwealth.com/2025/06/09/legacy-is-built-not-inherited/) On top of that, he pointed to IT and AI challenges that are driving all business owners crazy right now.

## It Starts With an Assessment

Chris said it always starts with the same thing: an assessment, or what he calls a roadmap, to see where you are on the road to wealth or lifestyle. It goes beyond sending over the P&Ls. He asks whether you're happy with your lifestyle and where you want to be, and he looks at the systems behind the P&Ls.

He listed 3 reasons businesses fail: a faulty business plan, inadequate funding, or a faulty or inadequate management team. So the first thing he looks at is whether the owner built a rock-solid foundation, or whether there are chinks in the armor to shore up. Even if an owner says their problem is AI and tech integration, he still starts with the same assessment, because there may be a bigger problem with funding, capitalization or systems.

The work is custom-tailored to the owner's budget. He pointed out that a business doing $150,000 a year gross is a different animal from one doing $5 million that wants to scale.

## Funding Takes a Plan

Funding came up as a big one. Chris said many owners haven't tapped into the ways to get funded and don't know the first step, which is having a plan based on where you are right now. He described an owner going after a line of credit: before applying, they shore up everything in the business so it looks good to lenders. In his view, the difference between the owner who wants money and the one who gets it is a solid foundation and a funding plan in place before anyone applies.

The options depend on the business. At $150,000 gross, he said an owner's only choice may be the bank they already have a relationship with, or something like hard money lending or credit card stacking. It's different for each person.

## Running a Business vs. Running It Out of Your Back Pocket

Chris said many small businesses start out of the owner's back pocket. He used the example of a good plumber who learned the trade, gets tired of making a wage and starts a business. Friends and family become the first customers, revenue reaches $50,000, $80,000 or $100,000 a year, but there's no business plan and no look at the management team.

He said even businesses up in the million-dollar range often haven't made the shift. They're still trading hours for dollars and aren't actually running a business. If an owner wants to pass the business to their kids, he'd say get the accountant involved and look at the whole structure. His analogy: your business is another baby, and you have to feed it first so it has the foundation to grow.

The question he asks owners is simple: do you want to run a business, or keep growing something you run out of your back pocket?

## Building the Right Team

We asked about partners. Chris said he's constantly searching for professionals across legal, accounting, financial planning, virtual assistants and tech, and he wants at least 2 of each on his team. He's not looking for people who just send details. He wants A-players he trusts to take care of anyone he sends their way, because it comes back on him.

Dan said that matches how we work: we like to be the quarterback of a family's financial situation and bring in other specialists as needed. If you're weighing what to look for in a planner, we share our thinking in our [guide to finding a financial planner.](https://yourtailoredwealth.com/2025/03/07/finding-a-financial-planner-who-saves-and-makes-you-more-than-they-cost/)

## Where He Sees Small Business Going

Chris called this a catastrophic perfect storm for small business, and he was clear that it's his personal opinion. He pointed to a landscape of mega-corporations on one side and small companies struggling to survive on the other. His example: AI might cost a small business $5,000 to $30,000 to embrace, while a mega-corp might throw $1 million or $5 million at it. He believes tech combined with AI is changing the world more drastically than the industrial revolution.

For owners who are hiding their heads in the sand, especially Gen X and Boomer owners, his question is where they are, because maybe they just want to cash out. In that case, his approach is to get the business to its highest valuation. For owners who want to grow, the challenge is how to compete with the tools and budget they have against companies with multi-million-dollar budgets.

Dan noted another side of this. A recent guest buys blue-collar small businesses, and one opportunity is that many Baby Boomer owners want to sell and retire, while a buyer can digitize a business with a strong brand and cash flow. Chris agreed it's an exciting time, but a challenging one if you don't embrace the changes quickly. If you're considering a sale, the U.S. Small Business Administration has a guide to [closing or selling your business.](https://www.sba.gov/business-guide/manage-your-business/close-or-sell-your-business)

## The Lesson: You Can't Do It All Yourself

Chris said one of his biggest challenges started around age 30 and continues: he can't do it all himself. At 30, he said, he was arrogant and thought he knew everything. Every decade, he realizes how much he doesn't know. Even at the peak, when he was making a lot of money, the lesson was the same.

He described a partner, a crusty old British accountant, who balanced him out. Chris was the one out meeting people and generating creative ideas, and the accountant was in the back with the numbers. He said you're not an island, and you have to ask for help. When owners say they'll learn the next step on the internet, his response is that AI can't teach you the next step the way someone who has been there can.

## Lightning Round Highlights

*   **Coffee or tea, cats or dogs:** Coffee and dogs.
*   **Tech he can't live without:** An autoresponder and CRM.
*   **Favorite quote:** “The two most important days of your life are the day that you were born and the day you figure out why.” He attributed it to Samuel Clemens.
*   **Favorite book:** Think and Grow Rich by Napoleon Hill, with Rich Dad Poor Dad among the others he named. He said books are part of your toolkit.
*   **Personal hack:** Be thankful for whatever is in front of you, good, bad or ugly, because you'll learn from it. He also said it isn't a failure until you don't get back up.
*   **Bucket list item already checked off:** At 20 he set a goal to have his own human performance facility by 30. Just before his 30th birthday he assembled a team and asked for help, and he said he raised the money within 90 days and opened a facility in Cincinnati that tested athletes and executives.
*   **Milestone he's working toward:** Becoming a billionaire, which he said isn't about focusing on money.
*   **Advice to his younger self:** Ask for help. Humble yourself.

## What Most People Miss

Many owners think of the sale as the event. Chris's point is that the sale price is a result of what you built before it. Systems, funding, a management team and a business plan are the foundation, and he says to shore it up before you go to a lender or a buyer.

The other thing is the owner's own role. A business that depends on the owner trading hours for dollars looks different from one that runs on systems and a team. Asking for help early, from an accountant, an advisor and the right experts, is a theme he returned to more than once.

## Example (Hypothetical): What a Stronger Foundation Could Mean at a Sale

Assume a business earns $400,000 a year in profit. These multiples are assumed, and real multiples vary widely by business and buyer.

*   **Before cleanup:** A buyer sees thin documentation and an owner-dependent business and values it at 3x profit: $400,000 × 3 = $1,200,000.
*   **After shoring up the foundation:** With cleaner books, documented systems and a team in place, a buyer values it at 3.5x: $400,000 × 3.5 = $1,400,000.
*   **The difference:** $200,000.

This is an illustration of why preparation matters, not a prediction. It isn't a valuation, and it isn't a claim about what any business would sell for. A valuation professional, your CPA and your attorney can give you real numbers. Taxes and transaction costs also reduce what you keep, so the amount you net is what drives your plan.

## How This Fits Our Approach at Tailored Wealth

We're not business brokers or valuation professionals, and we don't evaluate or recommend Chris's firm or any advisory group. What we do is connect a business owner's exit to the rest of their plan. We use Life-Driven Planning, our 6-phase process (Cash Flow, Retirement & Hybrid Retirement, Risk, Expense & Goal, Tax and Legacy), to look at the whole picture. Hybrid Retirement is a phased approach where full-time work gives way to flexible, optional work rather than an abrupt stop.

For an owner thinking about selling or passing the business on, the Tax and Legacy phases matter early, because the decisions around structure and timing come well before the closing date. To see what a plan covers end to end, watch [What a Real Financial Plan Includes.](https://yourtailoredwealth.com/videos/what-a-real-financial-plan-includes-and-why-starting-now-compounds-your-advantage/)

## Who This Is For

This episode is for small business owners, especially Gen X and Boomer owners, who are starting to think about an exit, a sale or passing the business to their kids. It's also for executives and owners in their 40s and 50s with complex income who want their business, taxes and retirement timeline to work together.

## Frequently Asked Questions

### 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 his website and ways to reach him at the end of the episode, and Dan said the contact details would be in the show notes on the video.

### What should a business owner do before putting a company up for sale?

Chris's starting point is an assessment of where the business stands: the business plan, funding, management team and the systems behind the financials. He said there's a big difference between how a company looks financially and how much an owner can get if they cash out. A valuation professional, your CPA and your attorney can give you real numbers for your situation. This is general education from the guest's perspective, not legal, tax or valuation advice.

### What does it mean to run a business instead of running it out of your back pocket?

Chris described owners who started out of their back pocket without a business plan or a look at the management team, and who are still trading hours for dollars even at the million-dollar range. His question is whether the owner wants to run a business or keep growing something that depends on them. His suggestion is to look at the whole structure and involve an accountant.

### How does selling a business fit into a retirement plan?

For many owners, the business is the largest part of their wealth, so the timing, the after-tax proceeds and what comes next all matter. Some owners don't want an abrupt stop. A Hybrid Retirement, where full-time work gives way to flexible, optional work rather than an abrupt stop, is 1 way to think about it, and we walk through it in [Retire Gradually, Not All at Once (Hybrid Plan Guide](https://yourtailoredwealth.com/videos/retire-gradually-not-all-at-once-hybrid-plan-guide/). If you'd like to see how your business, taxes and retirement timeline fit together, you can [book a Free Wealth Strategy Call.](https://yourtailoredwealth.com/book-a-call)

## Talk Through Your Own Plan

If you own a business and want to see how a sale or transition would fit into your retirement, tax and estate picture, we're happy to talk it through. It's a low-pressure conversation about your situation. [Book a Free Wealth Strategy Call.](https://yourtailoredwealth.com/book-a-call)

_Disclosure_

_The information provided is for educational and informational purposes only and does not constitute investment advice and it should not be relied on as such. It should not be considered a solicitation to buy or an offer to sell a security. It does not take into account any investor's particular investment objectives, strategies, tax status or investment horizon._

_No investment strategy or risk management technique can guarantee returns or eliminate risk in any market environment.  
  
All investments include a risk of loss that clients should be prepared to bear. The principal risks of Tailored Wealth’s strategies are disclosed in the publicly available Form ADV Part 2A._

_The views expressed in this commentary are subject to change based on market and other conditions. These documents may contain certain statements that may be deemed forward looking statements. Please note that any such statements are not guarantees of any future performance and actual results or developments may differ materially from those projected. Any projections, market outlooks, or estimates are based upon certain assumptions and should not be construed as indicative of actual events that will occur._

_Tailored Wealth and its advisors do not provide legal, accounting, or tax advice. Consult your attorney or tax professional.  
  
_