Two Sides of the Table

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

  1. 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

  2. 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

  3. 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

  4. 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

  5. 11/17/2025

    Season 2 episode 6 - The Real Future of AI with Braden Voigt

    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.

    42 min

  6. 11/03/2025

    Season 2 Episode 5 - Leading with Purpose at Corp IT with Darren Rath

    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.

    44 min

  7. 10/20/2025

    Season 2 Episode 4 - How David Mitchell is Redefining MSP Leadership at Grassroots IT

    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.

    35 min

  8. 10/06/2025

    Season 2 Episode 3 - Mark Andersen on Trust, Client Value, and the Long Game in IT

    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.

    46 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
    22
  • Rating
    Clean
  • Copyright
    © Copyright 2025 All rights reserved.
  • Show Website
    Two Sides of the Table