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

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In this episode, we break down the core idea behind our entire process… The One Number.

What is it?

It’s not a budget.

It’s not a restriction.

It’s a spending plan built around your real life.

We talk about:

• Why “budget” feels restrictive and “spending plan” feels empowering
• How unconscious spending quietly derails financial goal
• Why tracking 12 accounts is exhausting and unnecessary
• How automating fixed expenses creates clarity
• The psychology of weekly resets
• Why the number resets every seven days
• The difference between intentional spending and impulse spending
• How The One Number reduces stress and anxiety
• Why it works for both over spenders and under spenders
• How every $100 per week equals $5,200 per year
• Understanding tradeoffs and making confident choices

This episode is about clarity.

Instead of tracking categories, apps, and mental math… you focus on one number per week for discretionary spending.

Groceries. Eating out. Entertainment. Clothes. Retail therapy. All of it lives inside that number.

Everything else is automated.

The result?

Less stress.
More confidence.
Real freedom.

You’ll also hear how The One Number becomes a permission slip for people who are afraid to spend, and a boundary for people who struggle to rein it in.

It’s not about saying no.

It’s about saying yes on purpose.

And yes… we even talk about the free bread that somehow cost $35.

Next episode, we move to The Number 10 and introduce a special guest.

If this episode clicked for you, share it with someone who needs less financial chaos and more clarity.

See you next time.

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.

Twenty years.

That’s the number that launches The Number.

The milestone number 20 marks Wendy’s twentieth year in the financial industry. What began as business consulting evolved into an independent financial planning practice grounded in curiosity, education, and doing what is right—not what is easy.

In this first episode, Wendy Brookhouse and Kelsey MacAulay introduce the podcast and the concept behind it: beginning every conversation with a number and uncovering the story that sits behind it.

Wendy and Kelsey discuss what has changed over the past two decades, from pandemic‑driven digital acceleration to the rise of AI and faster approval processes. They also explore what has stayed constant: every client brings their own story, fears, aspirations, and definition of success.

With fewer than 17 percent of independent financial advisors being female, Wendy reflects on the importance of empathy and emotional intelligence in modern financial planning—skills that she believes will matter even more in the years ahead.

They also outline the three core planning pathways at Black Star Wealth:

• The One Number Solution
• Retirement Planning
• Total Wealth Blueprint for Business Owners

You’ll hear why the firm is shifting toward fixed‑fee models to offer greater transparency and clarity for clients.

This episode sets the tone for what The Number is all about: clarity, empowerment, and real conversations about the numbers that shape your life.

Join The Freedom Files
Tired of money advice that feels complicated or out of touch?
Discover Freedom Files from Black Star Wealth — a bi-weekly dose of smart financial insights and real stories about building a life on your own terms.
Because freedom isn’t someday — it’s something you design.
Subscribe now at blackstarwealth.com/freedomfiles

This episode takes a turn.
Wendy’s not in the host chair.
I slide in to interview her and Kelsey as we wrap up 2025 and look straight into 2026.

We cover what surprised them about business owners this year, where owners are getting stuck, why so many people are tired, and why resilience and action suddenly matter more than ever.

We dig into the myths that refuse to die, the habits that make a business sellable, and the blind spots that can wipe out value overnight.

We also talk about life after the sale.
The identity stuff.
The what now moment.

If you’re planning to sell in five years or you’re nowhere near ready but want the option, this one will get you thinking.

Join The Freedom Files
Tired of money advice that feels complicated or out of touch?
Discover Freedom Files from Black Star Wealth — a bi-weekly dose of smart financial insights and real stories about building a life on your own terms.
Because freedom isn’t someday — it’s something you design.
Subscribe now at blackstarwealth.com/freedomfiles

AI is showing up everywhere in business.

And a lot of owners are turning it on without realizing what they just gave access to.

In this episode, Wendy sits down with Darryl Cresswell, CEO and founder of myDWARE, to talk about why cybersecurity has to come before any AI rollout.

They dig into real world examples entrepreneurs can actually relate to.

AI agents running under owner level access.

Sensitive data leaking through email, CRM systems, and shadow AI tools.

And why flashy automation without guardrails can quietly destroy trust, value, and deal readiness.

Darryl breaks down the difference between AI bots, AI agents, and agentic AI in plain language.

They talk about shadow AI, third party tools, and how employees accidentally create risk.

And why buyers and auditors are now paying close attention to cybersecurity when valuing a business.

If you are experimenting with AI, thinking about automation, or planning to sell your business one day, this conversation will change how you think about “just turning it on.”

Cybersecurity first.
AI second.
Always.

I invited Graham Barlow onto The Real Bottom Line because his founder journey is one of the wildest I’ve ever heard. He started out as a teenager selling virtual game items on eBay, scaled that “hobby” into almost six figures a month, and eventually went on to build and exit multiple companies.

In our conversation, Graham and I dig into

• How he and a group of friends used bots to farm virtual currency long before in-app purchases were normal
  
• Why cash flow, projections, and financial discipline matter far more than top-line revenue
  
• The painful lessons he learned building a game studio and raising money

• How ego and “I’m the only one who can do this right” thinking quietly caps your business

• Why community and the rooms you put yourself in can dramatically change your sense of what’s possible

• The two strategic gaps he sees in most businesses right now… outbound sales and how teams use AI

We also talk about Founder Link, the community he never planned to build, and why so many founders desperately need a place where they can ask real questions, drop the armour, and get guidance from people who’ve already walked the path.

If you’ve ever hit a ceiling, questioned your next move, or wondered what it actually takes to build something someone would buy, you’ll get a lot from this conversation.

Join The Freedom Files
Tired of money advice that feels complicated or out of touch?
Discover Freedom Files from Black Star Wealth — a bi-weekly dose of smart financial insights and real stories about building a life on your own terms.
Because freedom isn’t someday — it’s something you design.
Subscribe now at blackstarwealth.com/freedomfiles

FinTech leader Carrie Forbes, CEO of Rockstar Advisory, joins Wendy to unpack the shift from startup energy to running energy, the corporate habits worth keeping, and how to make AI projects succeed with tiny, low risk wins. Human skills remain the moat... and that’s the optimistic bottom line.

Join The Freedom Files
Tired of money advice that feels complicated or out of touch?
Discover Freedom Files from Black Star Wealth — a bi-weekly dose of smart financial insights and real stories about building a life on your own terms.
Because freedom isn’t someday — it’s something you design.
Subscribe now at blackstarwealth.com/freedomfiles