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.

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Because freedom isn’t someday — it’s something you design.
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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.

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Because freedom isn’t someday — it’s something you design.
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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

Wendy talks with Dr. Susan Reid, revisioning specialist, author, and keynote speaker, about designing life after work. They explore identity beyond titles, why meaning matters in retirement, and how a simple “being vision” guides the next chapter. Susan shares research, lived lessons from building and selling businesses, and practical tools like journaling push/pull factors and building a “retirement team” of strong and weak ties.

Show Notes (light timestamps)

• 0:00 — Intro and Susan’s path: scientist → MBA → PhD → entrepreneur
• 3:30 — The Bob Proctor yo-yo story and discovering vision
• 7:55 — Creating a category: ice cider, then maple whisky
• 12:10 — Why a seven-word vision moves people faster than a long plan
• 13:40 — “Life after work” and early-retirement trends
• 17:20 — Hard stop vs glide path and the anxiety dip
• 21:30 — Prep to vision: quiet, journaling, push/pull factors
• 24:30 — Open via nature, people, and the “universe”
• 26:20 — Your Retirement Team: strong ties and weak ties
• 33:00 — Values → being vision (stop obsessing about how)
• 38:36 — The art of becoming + how to reach Susan

Key Takeaways

• Treat retirement as revisioning: move from freedom from to freedom to.
• Start with values and a being vision, then let the how emerge.
• Build a Retirement Team for support and fresh ideas.
• Keep the vision simple enough to remember.
• Prototype the next chapter before you leap.

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

Episode: The Real Bottom Line with Wendy Brookhouse
Guest: Jennifer Williams, Founder of Firefly Insights

In this episode, I sit down with Jennifer Williams, founder and partial owner of Firefly Insights, to unpack one of the most exciting developments for Canadian entrepreneurs — Employee Ownership Trusts (EOTs).

If you’re a business owner starting to think about succession, exit planning, or legacy, this episode will open your eyes to a whole new way to transition your business — one that rewards your team, sustains your community, and can even save you millions in taxes.

We talk about:

• Jennifer’s unique path from nonprofit work to social entrepreneurship and employee ownership
• The tough mindset shift around profit versus mission
• How to find the right scale in your business without burning out
• The new Canadian EOT legislation and what it means for small and mid-sized companies
• Who qualifies, how the trust is structured, and the real financial and cultural benefits

My favorite moment: when Jennifer breaks down how profit can amplify your mission rather than distract from it.

If you’ve ever wondered, “What’s next for my business when I step away?”, this conversation might just change the way you think about exit planning.

Connect with Jennifer: fireflyinsights.ca

Email: jennifer@fireflyinsights.ca

Join The Freedom Files
Tired of money advice that feels complicated or out of touch?
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Because freedom isn’t someday — it’s something you design.
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Guest: Ray Samuels, Growth Advisor and Founder, Cer Capital

Episode in a sentence: Ray shares how “done beats perfect,” why relationships are the real currency, and how a simple idea plus disciplined iteration can create momentum, funding, and valuation growth.

What we cover

• From high-school dances to London Telecom to Direct Energy: Ray’s entrepreneurial through-line
• The 65% rule: ship, listen, iterate
• “Clarity beats complexity,” and getting “pedestrian” with customers to gather real feedback
• G.R.O.W. mindset: Gratitude, Resilience, Optimism, Willpower
• The Equal Tank story: a simple washer-fluid dispenser, environmental impact, and national rollout
• Funding growth: why sales orders are easier to fund than ideas
• Packaging a story investors understand and want to back
• Daily relationship rituals that keep your network alive

Key takeaways

• Ship at 65% and improve with feedback
• Relationships compound if you maintain them intentionally
• Keep the product and the story simple so adoption is easy
• Growth needs cash, data, and proof, not perfection
• Momentum creates new problems, but they are the right problems

Timestamps

• 00:00 Meet Ray and the power of relationships
• 02:30 Early entrepreneurship: dances, driveways, done over perfect
• 07:10 Iteration vs. perfection and the 65% rule
• 08:50 Clarity beats complexity and learning to listen
• 18:20 The G.R.O.W. mindset explained
• 23:20 Equal Tank: simple solution, big impact
• 28:20 When and how to fund growth
• 35:50 Packaging the story for partners and investors
• 36:30 Wrap: relationships and iteration as operating systems

Connect with Ray
LinkedIn: https://www.linkedin.com/in/ray-samuels-a20165/

Like this episode?
Subscribe, leave a review, and share it with a founder who needs a nudge to ship.

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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

In this episode, I'm joined by the incredibly insightful Lissa Daub, founder of Strong Impact Academy. We met online through a couple of mutual groups, and it was a meeting that just felt like kismet. Lissa hails from Edmonton, Alberta, and she’s a force to be reckoned with.

Lissa and I dive into some of the most critical topics for business owners, from the mindset shifts of moving from corporate to entrepreneurship, to the surprising truth about owning a restaurant (it's not always sexy!). We talk about how the pandemic actually opened up new opportunities and simplified things for business owners, and Lissa shares her biggest lesson: you can’t just build it and expect them to come.

The heart of our conversation is all about the end game. As a Certified Exit Planning Advisor, Lissa is passionate about helping entrepreneurs understand that a profitable business isn't always a sellable one. We explore why it's so important to think about the value of your business as a key performance indicator and how to avoid the "owner's trap," where you build a job for yourself instead of a sellable asset. We also talk about The Exit Lab, a workshop that helps business owners intentionally prepare for their future.

In this episode, Lissa and I discuss:

• My favorite Lissa quote: "A profitable business is not always sellable, but a sellable business is always profitable."
• Why entrepreneurs are notorious for chasing shiny objects and how to stop.
• The biggest mistake business owners make around exit planning (and why it could cost you a fortune).
• How to hire strategically so you can focus on the things you love to do.
• The staggering statistic that 75% of business owners regret selling their business a year later and how you can avoid it.

Connect with Lissa:

• LinkedIn: https://www.linkedin.com/in/lissadaub

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