Two Sides of the Table

Carla Canning, founder of Connect Lead Achieve, joins Kayla and Pete to unpack the people challenges that come with growing a business. With a background in HR, Carla shares a practical perspective on building high-performing teams, exploring why employees leave, the gap between intention and action, and the challenges of managing performance and leadership.

Jason Maricchiolo, founder of ISO 365, joins Kayla and Pete to unpack what ISO compliance really means for MSPs and IT providers. From ISO 27001 and quality standards to AI governance and cyber insurance, this episode explores how businesses can use compliance to build trust, improve processes, and stand out in a crowded market.

Bryn Hardwood, a restructuring specialist at Carbon Corporate Restructuring with a background in accounting and advisory, joins Kayla and Pete to discuss what really happens when cash flow pressure escalates inside a tech business. From navigating ATO debt to understanding director responsibilities, this episode unpacks the practical options available to business owners and why acting early can make all the difference.

Season 3 of Two Sides of the Table kicks off with Tim Stephenson, CEO of SherpaTech. In this episode, we unpack the realities of cyber insurance—what it covers, what it does not, and how MSPs and IT businesses can better manage risk in a changing landscape.  

Geoff Hughes joins Peter and Kayla for the final episode of Season 2 to share insights from his journey building and exiting a successful MSP and what he is seeing now as the founder of Linkro. They explore how AI is reshaping the way MSPs operate, the real challenges behind business transformation, and why governance and compliance are often the biggest barriers to growth.

Lucas Meadowcroft, CEO of Crofti, joins Kayla and Peter to share his journey from running an MSP to building an AI automation business. This episode dives into what it takes to commercialise AI, why the traditional MSP model is shifting, and how to move from reactive support to strategic consulting.  

Brendan Gibson, CEO of Aspired, joins the table to talk about transparency, trust and the changing role of the MSP. From how to have better customer conversations to what the MSP of the future might look like, this episode is packed with insights for service providers navigating change.

Kayla and Peter are joined by Braden Voigt, CEO of Lynkz, to talk all things AI, innovation and partnerships. Braden shares how Lynkz is driving real ROI with AI, why so many projects fail, and what it takes to promote true innovation in tech.

Darren Rath, founder of Corp IT, joins us to talk about building a security-first IT business, navigating rapid growth, and leading with values. From choosing the right clients to creating a culture of trust, this episode covers what it takes to grow a sustainable MSP.

David Mitchell joins us on the podcast to share how he stepped into the CEO role at Grassroots IT, why co-leadership works, and what it takes to evolve beyond the traditional MSP model. We also talk AI, burnout, hybrid work, and why getting out of the weeds is easier said than done.

Mark Andersen, founder of Andersen IT, joins Two Sides of the Table to talk about building trust with clients, growing through professional services, and challenging the traditional MSP sales model.

In this episode of Two Sides of the Table, guest Paul Mangano unpacks what it means to lead an MSP in a market shaped by rising customer expectations, evolving technology and AI.

In this episode, we’re joined by Ashley Knowles to talk about what it takes to grow an MSP in today’s environment. From building partnerships to getting in front of your ideal customer, we explore what is working and what to leave behind.

Kayla and Peter explore how MSPs can stay competitive by embracing new technologies, adapting to shifting customer expectations, and avoiding burnout. From AI tools to business mindset, this episode is all about building long-term resilience.

In this episode, Kayla and Peter unpack what financial health really means for MSPs. From managing margins and customer concentration to tracking the right metrics and paying yourself properly, they share practical strategies to improve profitability and build long-term stability.

Kayla and Peter share what sustainable growth really looks like for MSPs. From financial planning to team structure and timing, this episode covers the key decisions that help you scale with confidence and avoid common pitfalls.

In this episode, Kayla and Peter share how MSPs can build stronger vendor partnerships to unlock bigger opportunities, improve deal flow, and support long-term growth. From account mapping to choosing the right vendors, they break down what it takes to get real value from your partner ecosystem.

In this episode, Kayla and Peter break down what it takes to prepare for and execute a successful M&A deal in the IT space. From knowing when you're ready to sell, to understanding due diligence, and working with advisors, they share real experiences and practical advice for business owners considering the next step.

Kayla and Peter share how MSPs can streamline operations by using the right tools, mapping processes, and applying automation where it matters most.

Kayla and Peter unpack how MSPs can price services effectively and communicate value with confidence. Learn what works, what to avoid, and how to align pricing with the outcomes your clients care about.

Discover how MSP and IT leaders can create high-performing teams through clear communication, trust, and a culture that supports growth and accountability.

In this episode, we explore what actually works when it comes to MSP marketing. Learn how to define your value, build the right audience, and measure meaningful results.

From common pitfalls in IT sales to structuring a repeatable sales process and mastering discovery calls—we’re breaking down exactly what it takes to build a sales process that works.

In this episode Kayla and Peter dive into some of the biggest challenges facing TSP's today and how to solve them. 

In this episode, we introduce Kayla and Peter, exploring their backgrounds, how they built their businesses, and what led them into the IT industry. This episode sets the stage for Two Sides of the Table, giving listeners a glimpse into the perspectives and conversations to come.