For two out of three business owners, selling the company will be the largest financial transaction of their lives. Yet most have never had it valued, and many don't know where to begin. In this episode, Wendy Brookhouse and Kelsey MacAulay dig into the number 66, why business value belongs right alongside revenue and profit as a metric worth tracking, and the practical first steps owners can take, often years ahead of a sale, to understand what their business is worth and build it into something worth transitioning.

In This Episode

• Why business value deserves a seat next to revenue and profit as a number to track every year
• What the "66%" and "less than 40%" figures reveal about how few owners actually know their number
• How to get a baseline read on your business's worth when a sale is still 5 to 10 years out
• Which levers can lift both your profit and your multiple, and why that combination changes the sale price so dramatically
• Who belongs on your exit team, and why a transaction specialist is not the same as your generalist lawyer
• Why waiting until you're tired weakens both your energy and your bargaining position

Featured Quote

About the Hosts

Wendy Brookhouse is the founder and chief strategist at Black Star Wealth and a Certified Financial Planner with over 20 years of independent advisory experience. She works with entrepreneurs and business owners to build financial clarity, business value, and wealth that lasts.

Kelsey MacAulay is the Chief Operating Officer and Chief Relationship Officer at Black Star Wealth, and a Certified Exit Planning Advisor. He works with business owners on the operational and strategic side of building a business worth transitioning.

Resources & Links

• CEPA (Certified Exit Planning Advisor): the credential Kelsey points to when choosing an advisor who specializes in transitions
• Baseline business valuation: an informal valuation to establish a starting number, referenced in the episode as a service Black Star Wealth offers
• Canadian Federation of Independent Business (CFIB): succession research cited in the episode (roughly 76% of owners planning to transition within 10 years, and 9% with a written plan)

Connect With Black Star Wealth

• Website: blackstarwealth.com
• LinkedIn: Wendy Brookhouse | Kelsey MacAulay
• Podcast: The Number, available on all major platforms

If knowing your number feels overdue, visit blackstarwealth.com to learn whether a baseline valuation is a fit for where you're at.

The Canada Pension Plan comes off almost every paycheque, but most business owners never stop to ask how it works or what it means for them. In this episode, Wendy Brookhouse and Kelsey MacAulay use the average CPP payment of $925.35 a month as a way in. They explain how contributions work, why the choice between paying yourself salary or dividends has gotten closer than it used to be, when it might make sense to take CPP early or wait, and how your pay structure shows up when you eventually sell your business.

In This Episode

• Understand what CPP is and how the 5.95% contribution works, including why the self-employed pay both halves at 11.9%
• See why the tax gap between paying yourself salary and paying yourself dividends has narrowed, and what that means for your pension and for getting financing
• Weigh the tradeoffs of taking CPP early, which reduces your benefit each month before 65, against waiting, which increases it each month up to 70, and learn where the crossover point lands
• Recognize how your pay structure looks during a sale, when buyers normalize salary and add dividends back into profit
• Find out how to check what you are actually eligible to collect through Service Canada

Most business owners have run a few prompts through ChatGPT and assumed that counts as using AI. Susan Diaz, CEO and founder of Northlight AI and author of Swan Dive Backwards, joins Wendy and Kelsey to make the case for going deeper. The conversation covers why AI literacy matters more than access, how to treat AI as delegation instead of magic, and why documenting how your business actually runs is both the starting point for AI and a quiet driver of business value.

In This Episode

• Understand the difference between AI access and AI literacy, and why a license alone doesn't move the needle
• Reframe AI as delegation, so a weak result points you back to a weak brief rather than a broken tool
• See why writing down how your business works builds intellectual property and makes the business more valuable and sellable
• Use the 10/80/10 approach, where you set the thinking, let AI carry the middle, and keep the final polish
• Pick one tool and get better at it instead of chasing every new headline and feature
• Ask the harder questions about jobs, security, and adoption that leadership tends to skip

Featured Quote

About the Hosts

Wendy Brookhouse is the founder and chief strategist at Black Star Wealth and a Certified Financial Planner with over 20 years of independent advisory experience. She works with entrepreneurs and business owners to build financial clarity, business value, and wealth that lasts.

Kelsey MacAulay is the Chief Operating Officer and Chief Relationship Officer at Black Star Wealth, and a Certified Exit Planning Advisor. He works with business owners on the operational and strategic side of building a business worth transitioning.

About Our Guest

Susan Diaz is the CEO and founder of Northlight AI and the author of the self-published book Swan Dive Backwards. She works largely with small businesses on practical AI adoption and hosts a long-running podcast with more than 275 episodes. She wrote her book by recording 25 episodes over 30 days, 13 of them with guests, and using AI to help structure and cross-reference the material.

Resources & Links

• Swan Dive Backwards by Susan Diaz, available on Amazon (including Amazon Canada)
• Northlight AI, Susan Diaz's company
• The four AI archetypes from the book and its companion quiz: the Diver, the Pathfinder, the Operator, and the Bridge Builder
• The Big Leap and its four zones of incompetence, competence, excellence, and genius, referenced in the conversation

Connect With Black Star Wealth

• Website: blackstarwealth.com
• LinkedIn: Wendy Brookhouse | 1
• Podcast: The Number, available on all major platforms

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The number is 44,000: businesses that closed in a single year, most of them not sold, just shuttered. Manja Horner, leadership strategist and founder of Boost Learning Design, joins Wendy and Kelsey to unpack why so many trades owners are walking away with no successor and no plan for the knowledge they spent decades building. The conversation looks at the hidden costs of skipping training, the brain drain hitting the trades, and what it takes to build a business that actually holds its value.

In This Episode

• Why "figure it out as you go" can quietly cost owners up to 8 percent on every project
• What goes wrong when a strong tradesperson is promoted into management without training
• How to think about training and HR as core business functions rather than overhead
• Why a quarter of the trades workforce is heading for retirement, and what that means for owners
• What a knowledge capture system looks like, and why it matters before key people leave
• How leadership and skills training tie directly to business value and exit readiness

Featured Quote

"Yes, we have the bodies leaving. We haven't talked about the brain drain that's happening." — Manja Horner

About the Hosts

Wendy Brookhouse is the founder and chief strategist at Black Star Wealth and a Certified Financial Planner with over 20 years of independent advisory experience. She works with entrepreneurs and business owners to build financial clarity, business value, and wealth that lasts.

Kelsey MacAulay is the Chief Operating Officer and Chief Relationship Officer at Black Star Wealth, and a Certified Exit Planning Advisor. She works with business owners on the operational and strategic side of building a business worth transitioning.

About Our Guest

Manja Horner is a third-generation tradesperson, leadership strategist, and founder of Boost Learning Design. She helps trades businesses fix the leadership training and accountability breakdowns that drive turnover and crush margins. She is the author of Pass the Torch: A Call to Rescue the Future of Trades.

Resources & Links

• Pass the Torch by Manja Horner: passthetorchbook.com
• Boost Learning Design (Manja's company)

Connect With Black Star Wealth

• Website: blackstarwealth.com
• LinkedIn: Wendy Brookhouse | Kelsey MacAulay
• Podcast: The Number, available on all major platforms

If this episode resonated, follow The Number so you don't miss what's next.

Money is still the number one source of stress for Canadians, and this episode gets into what the data actually shows. Wendy and Kelsey walk through the 2026 FP Canada Financial Stress Index — nine years of tracking financial anxiety across the country — and zero in on one number that tells the real story. People who work with a financial professional are 14 percentage points less likely to lose sleep over money. That gap shows up twice in the survey. This episode explains why, and what it looks like in practice.

In This Episode

• What's driving financial stress for Canadians in 2026 and how it's shifted over the past few years
• How financial anxiety breaks down differently across age groups — from early career to peak earning years
• Why the 14-point gap between people with a planner and those without keeps showing up in the data
• What the shift from "freedom from" to "freedom to" language tells you about where someone is in their financial journey
• Why waiting until you have things figured out before seeing a planner is the wrong approach

Featured Quote

About the Hosts

Wendy Brookhouse is the founder and chief strategist at Black Star Wealth and a Certified Financial Planner with over 20 years of independent advisory experience. She works with entrepreneurs and business owners to build financial clarity, business value, and wealth that lasts.

Kelsey MacAulay is the Chief Operating Officer and Chief Relationship Officer at Black Star Wealth, and a Certified Exit Planning Advisor. He works with business owners on the operational and strategic side of building a business worth transitioning.

Resources & Links

• FP Canada Financial Stress Index (2026) — the survey referenced throughout this episode.

Connect With Black Star Wealth

• Website: blackstarwealth.com
• LinkedIn: Wendy Brookhouse | Kelsey MacAulay
• Podcast: The Number — available on all major platforms

Curious whether Black Star Wealth works with people in your situation? Visit blackstarwealth.com to learn more.

The Number | Episode 004 — Long-Game Thinking

Bryan Clayton built a landscaping company from a single push mower to 150 employees and eight figures in annual revenue — then sold it. Then he started over. In this episode, Bryan shares the number that guided his second act: 10. Not a revenue target or a headcount — a timeframe. He and Wendy talk through what it actually takes to build a business that works, why most "overnight successes" are the result of a decade of quiet grinding, and how a single metric can be the difference between perseverance and delusion.

In This Episode

• Why every discretionary expense in your business costs you five to seven times that amount at the sale — and what to do about it
• How Bryan used one metric (weekly transactions) to stay focused and avoid building on a bad idea for years
• What "default alive" means, and why it's the most important financial position a business owner can hold
• The difference between a pivot that makes sense and one that just lets you avoid hard work
• Why thinking in decades — not quarters — is the mindset shift that changes how you run a business

Featured Quote

About the Hosts

Wendy Brookhouse is the founder and chief strategist at Black Star Wealth and a Certified Financial Planner with over 20 years of independent advisory experience. She works with entrepreneurs and business owners to build financial clarity, business value, and wealth that lasts.

Kelsey MacAulay is the Chief Operating Officer and Chief Relationship Officer at Black Star Wealth, and a Certified Exit Planning Advisor. He works with business owners on the operational and strategic side of building a business worth transitioning.

About Our Guest

Bryan Clayton is the CEO of GreenPal, a technology platform that connects homeowners with local lawn care providers. Before GreenPal, he built and sold Peachtree, a landscaping company based in Nashville, Tennessee, that grew to 150 employees and 90 trucks before being acquired by a national operator.

Resources & Links

• Built to Sell by John Warrillow — referenced by Bryan as a key resource for founders thinking about exit planning
• The Cashflow Quadrant by Robert Kiyosaki — referenced by Bryan when reflecting on life after his first exit
• 10x Is Easier Than 2x by Dan Sullivan and Dr. Benjamin Hardy — referenced by Wendy in conversation with Bryan

Connect With Black Star Wealth

• Website: blackstarwealth.com
• LinkedIn: Wendy Brookhouse | Kelsey MacAulay
• Podcast: The Number — available on all major platforms

If this episode resonated, follow The Number so you don't miss what's next.

The Number | Episode 3 — The One Number

Most people manage money reactively — checking their bank account after the fact and hoping it adds up. In this episode, Wendy and Kelsey dig into The One Number: Black Star Wealth's system for cutting through the noise of multiple accounts, competing priorities, and unconscious spending. They explain why a spending plan works better than a budget, how automating your fixed costs frees up mental energy, and how a single weekly number can give you both boundaries and permission — depending on what you need.

In This Episode

• Why "spending plan" works better psychologically than "budget" — and how the framing changes your relationship with money
• How The One Number works: automating fixed costs so you only need to track one weekly discretionary figure
• Why the number resets every seven days, and why that matters when life goes sideways
• How to use your weekly number to understand the real trade-off between paying down debt and maintaining your current lifestyle
• Why this system helps both over-spenders and under-spenders — and how it removes the guilt from both sides

Featured Quote

About the Hosts

Wendy Brookhouse is the founder and chief strategist at Black Star Wealth and a Certified Financial Planner with over 20 years of independent advisory experience. She works with entrepreneurs and business owners to build financial clarity, business value, and wealth that lasts.

Kelsey MacAulay is the Chief Operating Officer and Chief Relationship Officer at Black Star Wealth, and a Certified Exit Planning Advisor. He works with business owners on the operational and strategic side of building a business worth transitioning.

Resources & Links

• The One Number — Black Star Wealth's system for simplifying spending and aligning money with your goals. Learn more at blackstarwealth.com

Connect With Black Star Wealth

• Website: blackstarwealth.com
• LinkedIn: Wendy Brookhouse | Kelsey MacAulay
• Podcast: The Number — available on all major platforms

If this episode resonated, follow The Number so you don't miss what's next.

Got it — noted and saved. Kelsey MacAulay, and he. I'll make sure both the skill files and all future content reflect that correctly. Here are the corrected show notes:

From Interested to Committed: What 500 Sessions Teaches

The Number | Episode [#] — Commitment, Habits & Consistency

What does it take to stop being interested in something and actually commit to it? In this episode, Wendy and Kelsey get personal. Kelsey hit 500 gym sessions in under two years — tying for third fastest in his gym — and it changed more than his fitness. They unpack what made the habit stick, why identity matters more than motivation, and how the same thinking applies to the financial and business decisions that business owners keep putting off.

In This Episode

• Why convenience and structure matter more than willpower when building a lasting habit
• How blocking non-negotiable time — in your calendar and in your mindset — removes decision fatigue before it starts
• The difference between being interested in something and actually committing to it, and what it takes to flip that switch
• Why your reason for committing has to be genuinely yours — doing it for someone else rarely works
• How building one consistent habit can create capacity for things that previously felt out of reach
• What it looks like when a goal shifts from external motivation to a core part of how you see yourself

Featured Quote

About the Hosts

Wendy Brookhouse is the founder and chief strategist at Black Star Wealth and a Certified Financial Planner with over 20 years of independent advisory experience. She works with entrepreneurs and business owners to build financial clarity, business value, and wealth that lasts.

Kelsey MacAulay is the Chief Operating Officer and Chief Relationship Officer at Black Star Wealth, and a Certified Exit Planning Advisor. He works with business owners on the operational and strategic side of building a business worth transitioning.

Connect With Black Star Wealth

• Website: blackstarwealth.com
• LinkedIn: Wendy Brookhouse | Kelsey MacAulay
• Podcast: The Number — available on all major platforms

If this episode resonated, follow The Number so you don't miss what's next.