Podcast thumbnail for Are You Ready?

Are You Ready?

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by Kingston Ross Pasnak

9 episodes
Updated Daily
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Podcast Overview

A straight-talking video podcast for business owners, entrepreneurs, and family enterprises navigating big decisions. Hosted by veteran advisor Neil Cockburn of Kingston Ross Pasnak, each episode tackles a critical question: Are you ready for what’s next? From succession and exit planning to tax strategy, governance, and family dynamics, Neil draws on 40+ years of experience helping business owners prepare for the moments that matter most. Because the biggest risks in business aren’t the ones you see coming — they’re the ones you’re not ready for. Connect with Neil and learn more at: https://www.krpgroup.com/our-people/neil-cockburn

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Publishing Since

3/19/2026

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Recent Episodes

Episode thumbnail for Why Estate Planning Cannot Wait

July 3, 2026

Why Estate Planning Cannot Wait

<p>In this episode of Are You Ready?, Neil Cockburn is joined by Megan Harris of Barr LLP to discuss wills, estate planning, estate administration, and the problems that can arise when planning is delayed or incomplete.</p><p>Megan brings perspective from both the planning side and the litigation side, offering practical advice on when to create or update a will, why powers of attorney and personal directives matter, and how proper planning can reduce stress for loved ones during difficult times.</p><p>The conversation also covers probate in Alberta, common misconceptions about cost, the importance of keeping an updated asset list, and how to choose the right executor. Megan emphasizes that estate planning is not just about documents. It is about clarity, communication, and making things easier for the people who will have to act on your behalf.</p><p><strong>About Megan Harris<br></strong>Megan Harris is a lawyer with Barr LLP whose practice includes wills and estates, estate administration, estate litigation, adult guardianship and trusteeship applications, estate planning, litigation and dispute resolution, residential real estate, and foreclosure matters. She has represented clients at all levels of Alberta’s courts, including the Alberta Court of Justice, the Court of King’s Bench of Alberta, and the Alberta Court of Appeal.</p><p>Megan is focused on providing practical, efficient, and clear advice to help clients navigate legal matters with confidence. A graduate of the University of Alberta, she also serves on the executive for the Canadian Bar Association’s Young Lawyers’ Section and volunteers with the Edmonton Community Legal Centre.</p><p><br></p><p><strong>About Neil Cockburn<br></strong>Neil Cockburn is a Chartered Professional Accountant (FCPA), Family Enterprise Advisor (FEA), and Trust and Estate Practitioner (TEP), and the Director of Family Enterprise Advisory Services at Kingston Ross Pasnak LLP. With more than 40 years of experience working alongside business owners and family enterprises, Neil specializes in succession planning, intergenerational wealth transition, and estate strategy. He is known for helping families navigate complex transitions with clarity and confidence—always grounded in one central question: Are you ready for what comes next?</p><p>To learn more and connect with Neil Cockburn of Kingston Ross Pasnak, please visit: <a href="https://www.krpgroup.com/our-people/neil-cockburn">https://www.krpgroup.com/our-people/neil-cockburn</a></p><p>This video podcast series is proudly produced by the team at Road 55 - located in Edmonton, Alberta.<br>For more information, please visit: <a href="http://www.road55.ca/">www.road55.ca</a> </p><p><br></p>

Episode thumbnail for Fractional CFOs: Strategic Leadership for Family Enterprises

June 24, 2026

Fractional CFOs: Strategic Leadership for Family Enterprises

<p>How do you know when your business needs more financial leadership, but not necessarily a full-time CFO?</p><p>In this episode of Are You Ready?, Neil Cockburn sits down with longtime colleague and financial leader Ray Hawrelak to explore the growing role of the fractional CFO. With more than four decades of experience across real estate, public companies, private enterprises, family businesses, and not-for-profit organizations, Ray shares how businesses can access senior financial expertise exactly when they need it.</p><p>Ray reflects on a career that has taken him through economic downturns, corporate restructurings, company sales, public company leadership, and family enterprise transitions. Drawing on those experiences, he explains how the role of a fractional CFO extends far beyond financial reporting. Whether helping with acquisitions, financing, leadership transitions, governance, succession planning, or special projects, the role is often about providing experienced guidance during critical moments in a company's growth.</p><p>The conversation explores common misconceptions about fractional CFOs and why many business owners view them as temporary placeholders rather than strategic advisors. Ray explains that the most effective fractional CFOs stay close enough to the business to understand operations, identify risks, mentor future leaders, and bring valuable external perspective to management decisions.</p><p>For family enterprises, growing companies, and organizations facing increasing complexity, a fractional CFO can provide senior-level financial leadership without the commitment of a full-time executive. As Ray notes throughout the discussion, the goal is not simply oversight. It is helping businesses navigate change, build stronger financial foundations, and make better decisions.</p><p>This episode provides valuable insights for business owners wondering whether their organization is ready for the next level of financial leadership.</p><p><strong>About Ray Hawrelak</strong><br>Ray Hawrelak, FCPA-FCA, is a highly respected financial executive with more than 40 years of experience across public, private, family-owned, and not-for-profit organizations. Throughout his career, he has served in senior financial and operational leadership roles, including more than 20 years with Princeton Developments and executive positions within public companies, private equity-backed organizations, and family enterprises.</p><p>Today, Ray serves as a fractional CFO, director, and trusted advisor to entrepreneurs, family businesses, and private companies, helping organizations navigate acquisitions, divestitures, financing, succession planning, governance, and growth. He is known for his practical leadership, broad business experience, and ability to guide organizations through complex transitions with integrity and collaboration.</p><p><br></p><p><strong>About Neil Cockburn<br></strong>Neil Cockburn is a Chartered Professional Accountant (FCPA), Family Enterprise Advisor (FEA), and Trust and Estate Practitioner (TEP), and the Director of Family Enterprise Advisory Services at Kingston Ross Pasnak LLP. With more than 40 years of experience working alongside business owners and family enterprises, Neil specializes in succession planning, intergenerational wealth transition, and estate strategy. He is known for helping families navigate complex transitions with clarity and confidence—always grounded in one central question: Are you ready for what comes next?</p><p>To learn more and connect with Neil Cockburn of Kingston Ross Pasnak, please visit: <a href="https://www.krpgroup.com/our-people/neil-cockburn">https://www.krpgroup.com/our-people/neil-cockburn</a></p><p>This video podcast series is proudly produced by the team at Road 55 - located in Edmonton, Alberta.<br>For more information, please visit: <a href="http://www.road55.ca/">www.road55.ca</a> </p>

Episode thumbnail for Hugh Watt: Navigating Risk, Readiness, and Reality in Due Diligence

June 8, 2026

Hugh Watt: Navigating Risk, Readiness, and Reality in Due Diligence

<p>Selling a business is often the largest financial transaction an entrepreneur will ever undertake. Yet many owners underestimate the time, preparation, and scrutiny involved once a deal enters the due diligence phase.</p><p>In this episode of Are You Ready?, Neil Cockburn is joined by Hugh Watt, Chief Operating Officer of Acera Insurance, to explore the realities of due diligence during a business sale or acquisition. Hugh brings firsthand experience from multiple transactions, both on the buying side and the selling side, and shares lessons learned from helping guide companies through successful transitions.</p><p>The conversation covers what business owners should expect once a letter of intent is signed, why due diligence often takes longer than anticipated, and the importance of assembling the right team of advisors. Hugh discusses everything from quality of earnings reviews and financial reporting to confidentiality, management presentations, and the challenges of keeping a business running while simultaneously preparing for a transaction.</p><p>One of the key messages throughout the episode is that preparation creates options. Business owners who invest in strong systems, accurate reporting, and experienced advisors are far better positioned when an opportunity arises. Hugh also shares practical insights about deal fatigue, valuation expectations, legacy considerations, and why successful transactions are about much more than simply reaching a purchase price.</p><p>Whether you're considering a sale in the next year or the next decade, this episode offers a valuable look at one of the most critical phases of any business transition.</p><p><strong>About Hugh Watt</strong><br>Hugh Watt is Chief Operating Officer and Partner at Acera Insurance, where he helps lead operational strategy, partner integration, and growth initiatives across the organization. With more than 20 years of senior leadership experience in insurance, professional services, finance, and operations, Hugh has played a key role in numerous mergers, acquisitions, and business transitions.</p><p>Throughout his career, including leadership roles with Foster Park Brokers, NFP, Nilex, and Acera, he has worked closely with executive teams through acquisitions, ownership changes, post-transaction integration, and strategic growth initiatives. His practical experience on both the buy side and sell side of transactions provides a unique perspective on the challenges and opportunities business owners face when preparing for a sale or acquisition.</p><p>Known for his disciplined, execution-focused leadership style, Hugh is passionate about helping organizations navigate change while maintaining a strong focus on people, culture, and long-term success.</p><p><br></p><p><strong>About Neil Cockburn<br></strong>Neil Cockburn is a Chartered Professional Accountant (FCPA), Family Enterprise Advisor (FEA), and Trust and Estate Practitioner (TEP), and the Director of Family Enterprise Advisory Services at Kingston Ross Pasnak LLP. With more than 40 years of experience working alongside business owners and family enterprises, Neil specializes in succession planning, intergenerational wealth transition, and estate strategy. He is known for helping families navigate complex transitions with clarity and confidence—always grounded in one central question: Are you ready for what comes next?</p><p>To learn more and connect with Neil Cockburn of Kingston Ross Pasnak, please visit: https://www.krpgroup.com/our-people/neil-cockburn</p><p>This video podcast series is proudly produced by the team at Road 55 - located in Edmonton, Alberta.<br>For more information, please visit: www.road55.ca </p>

9 total episodes available

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What is Are You Ready??

A straight-talking video podcast for business owners, entrepreneurs, and family enterprises navigating big decisions. Hosted by veteran advisor Neil Cockburn of Kingston Ross Pasnak, each episode tackles a critical question:

Are you ready for what’s next?

From succession and exit planning to tax strategy, governance, and family dynamics, Neil draws on 40+ years of experience helping business owners prepare for the moments that matter most.

Because the biggest risks in business aren’t the ones you see coming — they’re the ones you’re not ready for.

Connect with Neil and learn more at: https://www.krpgroup.com/our-people/neil-cockburn

How often does this podcast release new episodes?

This podcast updates daily.

Where can I listen to this podcast?

This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.

Does this podcast accept guests?

Yes, this podcast regularly features guests.

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