Two Sides of the Table

Two Sides of the Table
  • 5.0 (1)
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A podcast designed for MSPs and IT business owners looking to scale, solve challenges, and stay ahead.

  1. 4h ago

    Season 3 Episode 5 – The Expert Season Halfway Recap with Kayla and Pete

    Kayla and Pete pause halfway through Season 3 to reflect on everything covered so far in the Expert Series.   From navigating insolvency and restructuring with Bryn Hardwood, to ISO certifications and AI governance with Jason Maricchiolo, cyber insurance with Tim Stephenson from SherpaTech, and the people and culture conversation with Carla Canning, this episode brings it all together.   They share the key takeaways from each guest, what surprised them, and what they are personally applying to their own businesses, before providing a preview of the four expert guests still to come in the back half of the season.

    21 min

  2. Apr 27

    Season 3 Episode 4 – Leadership, Culture and Performance in MSPs with Carla Canning

    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.

    42 min

  3. Mar 30

    Season 3 Episode 3 - How ISO & AI Governance Are Changing MSPs with Jason Maricchiolo

    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.

    44 min

  4. Mar 9

    Season 3 Episode 2 – Cash Flow, Insolvency and Restructuring in Tech with Bryn Hardwood

    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.

    42 min

  5. Feb 4

    Season 3 Episode 1 - Navigating Cyber Insurance with Tim Stephenson from SherpaTech

    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.

    41 min

  6. Jan 21

    Season 2 Episode 9 — AI and Exit Strategy with Geoff Hughes

    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.

    40 min

  7. Jan 4

    Season 2 Episode 8 - Going All In on AI with Lucas Meadowcroft

    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.

    43 min

  8. 12/01/2025

    Season 2 episode 7 - Brendan Gibson on Leadership, Vulnerability and Building Trust in MSPs

    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.

    44 min
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About

A podcast designed for MSPs and IT business owners looking to scale, solve challenges, and stay ahead.

Information

  • Creator
    Two Sides of the Table
  • Years Active
    2025 - 2026
  • Episodes
    26
  • Rating
    Clean
  • Copyright
    © Copyright 2025 All rights reserved.
  • Show Website
    Two Sides of the Table

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