Sell Me This Podcast

The managed services industry is changing faster than most operators realize — and the leaders who will thrive in the next five years are already thinking differently about how they build teams, serve clients, and adapt to what's coming.

Keith Daser opens Season 2 in conversation with Shawn Freeman, an operator who has spent years starting, scaling, and leading organizations in the managed services space. Shawn shares what he's learned from building teams in a changing industry and where the MSP model is heading as client expectations and technology shift simultaneously beneath operators' feet.

Topics covered:

• How the MSP model is evolving in response to new client expectations
• What strong leadership looks like in today's managed services landscape
• How forward-thinking MSPs are adapting to AI, automation, and shifting service delivery
• What Shawn has learned from years of building and scaling technology organizations
• Lessons for leaders growing managed services businesses in a competitive market
• What the next generation of MSP operators needs to get right

Find Shawn on LinkedIn: https://www.linkedin.com/in/shawnfreeman-/

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If you believe you deserve more from your technology partnerships, connect with the team at:
https://www.deliverdigital.ca/?utm_source=videodescription&utm_id=youtube

Sell Me This Podcast is brought to you by the team at Deliver Digital, a Calgary-based consulting organization that guides progressive companies through the selection, implementation, and governance of key technology partnerships. Their work is transforming the technology solution and software provider landscape by helping organizations reduce costs and duplication, enhance vendor alignment, and establish sustainable operating models that empower digital progress.

This episode of the Sell Me This Podcast was filmed in the Social Launch Labs studio. SLL delivers top-tier storytelling and technical excellence. A special thanks to the entire team for their dedication to crafting compelling content that engages, connects, and inspires.

Find the team at Social Launch Labs at:
www.sociallaunchlabs.com

Support the show

Sell Me This Podcast is brought to you by the team at Deliver Digital, a Calgary-based consulting organization that guides progressive companies through the selection, implementation, and governance of key technology partnerships. Their work is transforming the technology solution and software provider landscape by helping organizations reduce costs and duplication, enhance vendor alignment, and establish sustainable operating models that empower digital progress. 

If you believe you deserve more from your technology partnerships – connect with the team at:
www.deliverdigital.ca

This episode of Sell Me This Podcast was expertly edited, filmed, and produced by Laila Hobbs and Bretten Roissl of Social Launch Labs, who deliver top-tier storytelling and technical excellence. A special thanks to the entire team for their dedication to crafting compelling content that engages, connects, and inspires. 

Find the team at Social Launch Labs at:
www.sociallaunchlabs.com

Calgary is one of Canada's most underrated tech ecosystems — and Ian Macdonald at KPMG has been one of its most consistent champions. In this Season 1 finale, he makes the case for why imagination and curiosity are the most undervalued business skills of the current moment.

Keith Daser talks with Ian Macdonald, Business and Innovation Leader at KPMG Canada, about the intersection of innovation, risk, and what it takes to build lasting business relationships in a fast-changing market. Ian shares why KPMG's commitment to the startup ecosystem doesn't lead with a sales agenda, what Calgary's emergence as a serious tech hub looks like from the inside, and why the technology isn't the hard part anymore.

Topics covered:

• Why imagination and curiosity are systematically undervalued in business leadership
• How KPMG approaches the startup ecosystem without leading with a pitch
• Why Calgary is positioning itself as a genuine Canadian tech hub
• The relationship between risk tolerance and meaningful innovation
• What large enterprises can actually do to fuel startup growth
• Why being curious rather than judgmental is a better business strategy than any framework

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If you believe you deserve more from your technology partnerships – connect with the team at:
https://www.deliverdigital.ca/?utm_source=videodescription&utm_id=youtube

Sell Me This Podcast is brought to you by the team at Deliver Digital, a Calgary-based consulting organization that guides progressive companies through the selection, implementation, and governance of key technology partnerships. Their work is transforming the technology solution and software provider landscape by helping organizations reduce costs and duplication, enhance vendor alignment, and establish sustainable operating models that empower digital progress.

This episode of the Sell Me This Podcast was expertly edited, filmed, and produced by Laila Hobbs and Bretten Roissl of Social Launch Labs, who deliver top-tier storytelling and technical excellence. A special thanks to the entire team for their dedication to crafting compelling content that engages, connects, and inspires.

Find the team at Social Launch Labs at:
www.sociallaunchlabs.com

Support the show

Sell Me This Podcast is brought to you by the team at Deliver Digital, a Calgary-based consulting organization that guides progressive companies through the selection, implementation, and governance of key technology partnerships. Their work is transforming the technology solution and software provider landscape by helping organizations reduce costs and duplication, enhance vendor alignment, and establish sustainable operating models that empower digital progress. 

If you believe you deserve more from your technology partnerships – connect with the team at:
www.deliverdigital.ca

This episode of Sell Me This Podcast was expertly edited, filmed, and produced by Laila Hobbs and Bretten Roissl of Social Launch Labs, who deliver top-tier storytelling and technical excellence. A special thanks to the entire team for their dedication to crafting compelling content that engages, connects, and inspires. 

Find the team at Social Launch Labs at:
www.sociallaunchlabs.com

Leading one of North America's largest technology channel programs takes more than process expertise. It takes the ability to see the whole partner ecosystem and build programs that genuinely work for everyone inside it.

Keith Daser talks with Cassie Jeppson, Director of Channel Programs and Operations Strategy at Lenovo, about how enterprise technology companies build and manage partner channels at scale. Cassie's path from hobby-farming in Tennessee to leading a major North American channel team is as unconventional as her perspective on what makes channel programs succeed — and what makes them fail.

Topics covered:

• What enterprise channel programs look like at Lenovo's scale
• How to build partner programs that create mutual value rather than just vendor incentives
• The evolution of channel strategy in response to direct sales and digital distribution
• What technology resellers and solution providers should know about working with OEM vendors
• Lessons from an unconventional path to enterprise channel leadership
• What agility actually means inside a large, complex organization

-----------------------------------------------------------------------------------------------------------------------------
If you believe you deserve more from your technology partnerships – connect with the team at:
https://www.deliverdigital.ca/?utm_source=videodescription&utm_id=youtube

Sell Me This Podcast is brought to you by the team at Deliver Digital, a Calgary-based consulting organization that guides progressive companies through the selection, implementation, and governance of key technology partnerships. Their work is transforming the technology solution and software provider landscape by helping organizations reduce costs and duplication, enhance vendor alignment, and establish sustainable operating models that empower digital progress.

This episode of the Sell Me This Podcast was expertly edited, filmed, and produced by Laila Hobbs and Bretten Roissl of Social Launch Labs, who deliver top-tier storytelling and technical excellence. A special thanks to the entire team for their dedication to crafting compelling content that engages, connects, and inspires.

Find the team at Social Launch Labs at:
www.sociallaunchlabs.com

Support the show

Sell Me This Podcast is brought to you by the team at Deliver Digital, a Calgary-based consulting organization that guides progressive companies through the selection, implementation, and governance of key technology partnerships. Their work is transforming the technology solution and software provider landscape by helping organizations reduce costs and duplication, enhance vendor alignment, and establish sustainable operating models that empower digital progress. 

If you believe you deserve more from your technology partnerships – connect with the team at:
www.deliverdigital.ca

This episode of Sell Me This Podcast was expertly edited, filmed, and produced by Laila Hobbs and Bretten Roissl of Social Launch Labs, who deliver top-tier storytelling and technical excellence. A special thanks to the entire team for their dedication to crafting compelling content that engages, connects, and inspires. 

Find the team at Social Launch Labs at:
www.sociallaunchlabs.com

Scaling a managed services company past $7 million in revenue teaches you things no course or coach can. Tim Thomson learned those lessons on the way up — and now passes them on to operators who are still climbing.

Keith Daser talks with Tim Thomson, former MSP founder, business coach, and creator of Cyber Trends, about what it actually takes to build and scale a managed services company from the inside. Tim shares the pivotal decisions, costly mistakes, and hard-won insights from his years growing a fast-moving MSP — and why he now dedicates his work to helping other operators avoid the same pitfalls.

Topics covered:

• What Tim learned scaling his MSP from startup to $7M+ in annual revenue
• The inflection points where most MSPs stall — and how to push through them
• Why culture and leadership become the bottleneck as an MSP grows
• How Cyber Trends approaches cybersecurity education for SMBs
• The mindset shift required to move from operator to owner
• What the future of managed services looks like for independent operators

-----------------------------------------------------------------------------------------------------------------------------
If you believe you deserve more from your technology partnerships – connect with the team at:
https://www.deliverdigital.ca/?utm_source=videodescription&utm_id=youtube

Sell Me This Podcast is brought to you by the team at Deliver Digital, a Calgary-based consulting organization that guides progressive companies through the selection, implementation, and governance of key technology partnerships. Their work is transforming the technology solution and software provider landscape by helping organizations reduce costs and duplication, enhance vendor alignment, and establish sustainable operating models that empower digital progress.

This episode of the Sell Me This Podcast was expertly edited, filmed, and produced by Laila Hobbs and Bretten Roissl of Social Launch Labs, who deliver top-tier storytelling and technical excellence. A special thanks to the entire team for their dedication to crafting compelling content that engages, connects, and inspires.

Find the team at Social Launch Labs at:
www.sociallaunchlabs.com

Support the show

Sell Me This Podcast is brought to you by the team at Deliver Digital, a Calgary-based consulting organization that guides progressive companies through the selection, implementation, and governance of key technology partnerships. Their work is transforming the technology solution and software provider landscape by helping organizations reduce costs and duplication, enhance vendor alignment, and establish sustainable operating models that empower digital progress. 

If you believe you deserve more from your technology partnerships – connect with the team at:
www.deliverdigital.ca

This episode of Sell Me This Podcast was expertly edited, filmed, and produced by Laila Hobbs and Bretten Roissl of Social Launch Labs, who deliver top-tier storytelling and technical excellence. A special thanks to the entire team for their dedication to crafting compelling content that engages, connects, and inspires. 

Find the team at Social Launch Labs at:
www.sociallaunchlabs.com

Decades of experience in IT outsourcing and enterprise analytics will teach you how organizations use data. Building Ethicrithm taught Matthew Nielsen something harder: what they should do with it — and why the ethical dimension of AI is the most underestimated business risk right now.

Keith Daser talks with Matthew Nielsen, founder and CEO of Ethicrithm and former CEO of Fishbone Analytics, about the arc of his career from IT outsourcing to analytics to building a company focused on ethical AI and responsible digital transformation. Matthew brings a rare long-view perspective on enterprise technology decisions and why frustration with how the industry operates became the fuel for how he built both companies.

Topics covered:

• What enterprise analytics actually looks like inside large organizations
• How IT outsourcing has evolved and what companies still get wrong about it
• Why the ethical dimensions of AI are being systematically underestimated
• What responsible digital transformation means in practice
• How Ethicrithm approaches AI governance for enterprise clients
• How turning frustration into fuel shapes better business outcomes

-----------------------------------------------------------------------------------------------------------------------------
If you believe you deserve more from your technology partnerships – connect with the team at:
https://www.deliverdigital.ca/?utm_source=videodescription&utm_id=youtube

Sell Me This Podcast is brought to you by the team at Deliver Digital, a Calgary-based consulting organization that guides progressive companies through the selection, implementation, and governance of key technology partnerships. Their work is transforming the technology solution and software provider landscape by helping organizations reduce costs and duplication, enhance vendor alignment, and establish sustainable operating models that empower digital progress.

This episode of the Sell Me This Podcast was expertly edited, filmed, and produced by Laila Hobbs and Bretten Roissl of Social Launch Labs, who deliver top-tier storytelling and technical excellence. A special thanks to the entire team for their dedication to crafting compelling content that engages, connects, and inspires.

Find the team at Social Launch Labs at:
www.sociallaunchlabs.com

Support the show

Sell Me This Podcast is brought to you by the team at Deliver Digital, a Calgary-based consulting organization that guides progressive companies through the selection, implementation, and governance of key technology partnerships. Their work is transforming the technology solution and software provider landscape by helping organizations reduce costs and duplication, enhance vendor alignment, and establish sustainable operating models that empower digital progress. 

If you believe you deserve more from your technology partnerships – connect with the team at:
www.deliverdigital.ca

This episode of Sell Me This Podcast was expertly edited, filmed, and produced by Laila Hobbs and Bretten Roissl of Social Launch Labs, who deliver top-tier storytelling and technical excellence. A special thanks to the entire team for their dedication to crafting compelling content that engages, connects, and inspires. 

Find the team at Social Launch Labs at:
www.sociallaunchlabs.com

Cybersecurity is no longer a technology problem — it's a business problem. And selling security solutions to enterprise organizations requires a completely different playbook than traditional tech sales.

Keith Daser talks with Scott Coleman, Enterprise Account Executive at Arctic Wolf, about his path from capital markets to enterprise cybersecurity sales and what he's learned about navigating complex buying decisions in a fast-moving threat landscape. Arctic Wolf is one of North America's leading security operations platforms, and Scott brings a ground-level view of what enterprise buyers actually care about when evaluating security vendors.

Topics covered:

• How Arctic Wolf approaches security operations differently from traditional vendors
• What enterprise buyers actually ask when evaluating cybersecurity platforms
• The sales cycle for complex security solutions — and how to navigate it
• Lessons from capital markets applied directly to enterprise tech sales
• Why mid-market companies are increasingly the most targeted cybersecurity segment
• How managed detection and response is changing how businesses approach risk

-----------------------------------------------------------------------------------------------------------------------------
If you believe you deserve more from your technology partnerships, connect with the team at:
https://www.deliverdigital.ca/?utm_source=videodescription&utm_id=youtube

Sell Me This Podcast is brought to you by the team at Deliver Digital, a Calgary-based consulting organization that guides progressive companies through the selection, implementation, and governance of key technology partnerships. Their work is transforming the technology solution and software provider landscape by helping organizations reduce costs and duplication, enhance vendor alignment, and establish sustainable operating models that empower digital progress.

This episode of the Sell Me This Podcast was expertly edited, filmed, and produced by Laila Hobbs and Bretten Roissl of Social Launch Labs, who deliver top-tier storytelling and technical excellence. A special thanks to the entire team for their dedication to crafting compelling content that engages, connects, and inspires.

Find the team at Social Launch Labs at:
www.sociallaunchlabs.com

Support the show

Sell Me This Podcast is brought to you by the team at Deliver Digital, a Calgary-based consulting organization that guides progressive companies through the selection, implementation, and governance of key technology partnerships. Their work is transforming the technology solution and software provider landscape by helping organizations reduce costs and duplication, enhance vendor alignment, and establish sustainable operating models that empower digital progress. 

If you believe you deserve more from your technology partnerships – connect with the team at:
www.deliverdigital.ca

This episode of Sell Me This Podcast was expertly edited, filmed, and produced by Laila Hobbs and Bretten Roissl of Social Launch Labs, who deliver top-tier storytelling and technical excellence. A special thanks to the entire team for their dedication to crafting compelling content that engages, connects, and inspires. 

Find the team at Social Launch Labs at:
www.sociallaunchlabs.com

Plug and Play is one of the world's most active seed-stage investors and startup accelerators — and its Alberta program is quietly becoming one of the most important forces in Canada's emerging tech landscape. Lindsay Smylie runs it.

Keith Daser talks with Lindsay Smylie, Director at Plug and Play Alberta, about what it looks like to invest in and accelerate early-stage technology companies in Canada. Lindsay brings a genuinely distinctive perspective — from corporate energy to craft distilling to startup acceleration — and shares what makes Alberta tech founders different, and what the ecosystem still needs to reach its potential.

Topics covered:

• What Plug and Play does globally and what the Alberta program specifically focuses on
• How seed-stage investors evaluate early-stage tech companies
• What makes Alberta a compelling and underrated place to build a tech company
• The role of corporate partnerships in startup acceleration
• What Canadian founders need to understand about raising capital
• How the energy sector transition is creating new startup opportunities in Alberta

-----------------------------------------------------------------------------------------------------------------------------
If you believe you deserve more from your technology partnerships, connect with the team at:
https://www.deliverdigital.ca/?utm_source=videodescription&utm_id=youtube

Sell Me This Podcast is brought to you by the team at Deliver Digital, a Calgary-based consulting organization that guides progressive companies through the selection, implementation, and governance of key technology partnerships. Their work is transforming the technology solution and software provider landscape by helping organizations reduce costs and duplication, enhance vendor alignment, and establish sustainable operating models that empower digital progress.

This episode of the Sell Me This Podcast was expertly edited, filmed, and produced by Laila Hobbs and Bretten Roissl of Social Launch Labs, who deliver top-tier storytelling and technical excellence. A special thanks to the entire team for their dedication to crafting compelling content that engages, connects, and inspires.

Find the team at Social Launch Labs at:
www.sociallaunchlabs.com

Support the show

Sell Me This Podcast is brought to you by the team at Deliver Digital, a Calgary-based consulting organization that guides progressive companies through the selection, implementation, and governance of key technology partnerships. Their work is transforming the technology solution and software provider landscape by helping organizations reduce costs and duplication, enhance vendor alignment, and establish sustainable operating models that empower digital progress. 

If you believe you deserve more from your technology partnerships – connect with the team at:
www.deliverdigital.ca

This episode of Sell Me This Podcast was expertly edited, filmed, and produced by Laila Hobbs and Bretten Roissl of Social Launch Labs, who deliver top-tier storytelling and technical excellence. A special thanks to the entire team for their dedication to crafting compelling content that engages, connects, and inspires. 

Find the team at Social Launch Labs at:
www.sociallaunchlabs.com

Growing a managed services business is technically complex — but the hardest problems are almost always operational, not technical. Todd Kane has spent years helping MSP founders work through both.

Keith Daser talks with Todd Kane, founder of Evolved Management Consulting and a recognized voice in MSP leadership, about the real-world challenges technical founders face when scaling managed services businesses. Todd draws from deep operational experience to explore what separates MSPs that scale from those that stall.

Topics covered:

• The most common operational failures MSP founders hit at each growth stage
• How to build systems and processes that don't depend on the owner
• The difference between technical excellence and operational maturity
• Hiring strategies for MSPs trying to scale their teams
• When to bring in outside expertise vs. build internally
• What MSP consolidation and acquisition activity means for independent operators

-----------------------------------------------------------------------------------------------------------------------------
If you believe you deserve more from your technology partnerships – connect with the team at:
https://www.deliverdigital.ca/?utm_source=videodescription&utm_id=youtube

Sell Me This Podcast is brought to you by the team at Deliver Digital, a Calgary-based consulting organization that guides progressive companies through the selection, implementation, and governance of key technology partnerships. Their work is transforming the technology solution and software provider landscape by helping organizations reduce costs and duplication, enhance vendor alignment, and establish sustainable operating models that empower digital progress.

This episode of the Sell Me This Podcast was expertly edited, filmed, and produced by Laila Hobbs and Bretten Roissl of Social Launch Labs, who deliver top-tier storytelling and technical excellence. A special thanks to the entire team for their dedication to crafting compelling content that engages, connects, and inspires.

Find the team at Social Launch Labs at:
www.sociallaunchlabs.com

Support the show

Sell Me This Podcast is brought to you by the team at Deliver Digital, a Calgary-based consulting organization that guides progressive companies through the selection, implementation, and governance of key technology partnerships. Their work is transforming the technology solution and software provider landscape by helping organizations reduce costs and duplication, enhance vendor alignment, and establish sustainable operating models that empower digital progress. 

If you believe you deserve more from your technology partnerships – connect with the team at:
www.deliverdigital.ca

This episode of Sell Me This Podcast was expertly edited, filmed, and produced by Laila Hobbs and Bretten Roissl of Social Launch Labs, who deliver top-tier storytelling and technical excellence. A special thanks to the entire team for their dedication to crafting compelling content that engages, connects, and inspires. 

Find the team at Social Launch Labs at:
www.sociallaunchlabs.com

Most businesses think managed service providers are just IT support. The right MSP relationship is something far more strategic — and choosing the wrong one costs more than the contract.

Keith Daser talks with Dustin Cassar, a managed services veteran with over two decades in the industry, about what MSPs really are, how their value has evolved since the early 2000s, and what businesses need to look for when selecting a technology partner. The conversation covers everything from the most common misconceptions about managed services to a real-world $500,000 business email compromise that proper security awareness could have prevented.

Topics covered:

• What a managed service provider actually does — and what it doesn't do
• How the MSP model evolved from break-fix IT to strategic trusted advisory
• The most common misconceptions businesses have about managed services
• How to evaluate and select the right MSP for your organization
• What MSP contracts should and shouldn't include
• How AI and cybersecurity are reshaping the managed services industry
• A real-world $500K business email compromise case study and what it teaches

Find Dustin on LinkedIn: https://www.linkedin.com/in/dustincassar/

-----------------------------------------------------------------------------------------------------------------------------
If you believe you deserve more from your technology partnerships – connect with the team at:
https://www.deliverdigital.ca/?utm_source=videodescription&utm_id=youtube

Sell Me This Podcast is brought to you by the team at Deliver Digital, a Calgary-based consulting organization that guides progressive companies through the selection, implementation, and governance of key technology partnerships. Their work is transforming the technology solution and software provider landscape by helping organizations reduce costs and duplication, enhance vendor alignment, and establish sustainable operating models that empower digital progress.

This episode of the Sell Me This Podcast was expertly edited, filmed, and produced by Laila Hobbs and Bretten Roissl of Social Launch Labs, who deliver top-tier storytelling and technical excellence. A special thanks to the entire team for their dedication to crafting compelling content that engages, connects, and inspires.

Find the team at Social Launch Labs at:
www.sociallaunchlabs.com

Support the show

Sell Me This Podcast is brought to you by the team at Deliver Digital, a Calgary-based consulting organization that guides progressive companies through the selection, implementation, and governance of key technology partnerships. Their work is transforming the technology solution and software provider landscape by helping organizations reduce costs and duplication, enhance vendor alignment, and establish sustainable operating models that empower digital progress. 

If you believe you deserve more from your technology partnerships – connect with the team at:
www.deliverdigital.ca

This episode of Sell Me This Podcast was expertly edited, filmed, and produced by Laila Hobbs and Bretten Roissl of Social Launch Labs, who deliver top-tier storytelling and technical excellence. A special thanks to the entire team for their dedication to crafting compelling content that engages, connects, and inspires. 

Find the team at Social Launch Labs at:
www.sociallaunchlabs.com

Bitcoin isn't just a speculative asset — it's a monetary system built on thousands of years of cryptographic history, designed to solve a problem that governments and central banks have made steadily worse. Koleya Karringten makes that case clearly and practically.

Keith Daser talks with Koleya Karringten, blockchain advocate, entrepreneur, and founder of the Canadian Blockchain Consortium, about the real story behind Bitcoin and distributed ledger technology. Koleya spent 17 years in clean tech before finding her way into Bitcoin through the energy and economics intersection — and her pragmatic lens cuts through the noise that dominates most blockchain conversations.

Topics covered:

• What Bitcoin actually is — the monetary case, the cryptographic history, and the scarcity argument
• Why Canada's monetary supply expansion is a more serious issue than most people realize
• How Bitcoin mining can turn Alberta's stranded energy assets into revenue streams
• Real enterprise use cases for blockchain (supply chain, food recall, provenance) vs. the hype
• What the Canadian government's role should be in creating a digital asset framework
• Why the Bitcoin Standard is the best starting point for anyone wanting to understand the space

Find Koleya at: canadablockchain.ca

Support the show

Sell Me This Podcast is brought to you by the team at Deliver Digital, a Calgary-based consulting organization that guides progressive companies through the selection, implementation, and governance of key technology partnerships. Their work is transforming the technology solution and software provider landscape by helping organizations reduce costs and duplication, enhance vendor alignment, and establish sustainable operating models that empower digital progress. 

If you believe you deserve more from your technology partnerships – connect with the team at:
www.deliverdigital.ca

This episode of Sell Me This Podcast was expertly edited, filmed, and produced by Laila Hobbs and Bretten Roissl of Social Launch Labs, who deliver top-tier storytelling and technical excellence. A special thanks to the entire team for their dedication to crafting compelling content that engages, connects, and inspires. 

Find the team at Social Launch Labs at:
www.sociallaunchlabs.com