Sell Me This Podcast
Ever wonder how a multi-million dollar tech deal actually gets done? Or why some "game-changing" startups vanish while others become the backbone of your business? Sell Me This Podcast is our attempt to map the wilderness of the modern tech scene. We’re sitting down with the people who live in the gaps between the sales pitches and the reality. It’s an exploration of the Western Canadian tech ecosystem and beyond - featuring the dreamers, builders and connectors who are actually doing the work, brokering the deals, and occasionally breaking things.
Episodes
On this episode of the Sell Me This Podcast, host Keith Daser talks with Nish Sampath, founder of Switch Advisory Group, about the growing role of fractional leadership in modern businesses.
Nish explains the difference between traditional consulting and fractional leadership, and why more companies are embedding experienced operators directly into their executive teams. Rather than advising from the outside, fractional le...
On this episode of the Sell Me This Podcast, host Keith Daser talks with Akshay Gulati, cloud architect and founder of Tech Connect Alberta, about technology, community-building, and servant leadership in action.
Akshay shares how Tech Connect Alberta began as a small grassroots effort during the pandemic and grew into a 15,000-member community focused on helping tech professionals and newcomers navigate the job market. Wh...
On this episode of the Sell Me This Podcast, host Keith Daser talks with Brandy Old and Craig Elias from Alberta Innovates about the real state of entrepreneurship in Canada and what it actually takes to build a viable business.
Brandy and Craig share their work as Technology Development Advisors, supporting founders through business coaching, commercialization guidance, and access to non-dilutive funding. They explain why...
On this episode of the Sell Me This Podcast, host Keith Daser talks with Meghan Donohoe and Alicia Wight, co-founders of Pebble, about rethinking leadership in a world that no longer fits traditional models.
They challenge the idea that leadership is about fixing problems and instead make the case for connection, reflection, and creating space for growth. Meghan and Alicia explain why leadership is non-linear, how the indu...
On this episode of the Sell Me This Podcast, host Keith Daser talks with Philippe Burns, co-founder and host of Tech Thursday, a weekly community networking series for Canada’s tech ecosystem.
Philippe shares his journey from roles at SkipTheDishes and Neo Financial to spinning Tech Thursday out as an independent, for-profit entity that now serves Calgary, Winnipeg, Edmonton, and Ottawa. They discuss his unique "anti-...
On this episode of the Sell Me This Podcast, host Keith Daser talks with Margo Purcell, Co-founder and CEO of InceptionU, about how the tech and labor markets are changing in Calgary and beyond, and what that means for the future of work.
Margo shares why the economy is shifting away from pure technical knowledge toward metaskills like adaptability, critical thinking, and collaboration. She explains why learning how to lea...
On this episode of the Sell Me This Podcast, host Keith Daser talks with Matt Riddel about the human side of sales and the importance of perspective in a performance-driven world.
Matt shares insights from his leadership coaching work on why sales professionals need to reflect on long-term growth, not just their most recent quarter or fiscal results. They explore how tying self-worth too closely to performance can undermin...
On this episode of the Sell Me This Podcast, host Keith Daser talks with Dr. Stella Lee. The conversation explores how organizations can build real AI literacy, why policy matters more than ever, and what it takes to prepare people for a future shaped by intelligent technology.
Dr. Lee breaks down the difference between understanding AI in theory and using it responsibly in practice. She shares insights on how schools, bus...
On this episode of the Sell Me This Podcast, host Keith Daser talks with Denise Baril, founder of The Grant Sherpa. The conversation explores the importance of community, the necessity of struggle, and the value of real human connection in both business and personal growth.
Denise shares stories from her journey supporting organizations through grants and funding opportunities, and explains why challenges often create the ...
On this episode of the Sell Me This Podcast, host Keith Daser talks with Jose Costa and Mark Mandel from MHM for a practical conversation on compliance, ethics, and security for small and medium-sized businesses.
They break down what compliance really means beyond the checklists, how ethics play a role in every security decision, and why the right controls can protect both data and reputation. Jose and Mark also share acti...
On this episode of the Sell Me This Podcast, host Keith Daser talks with Tim Chan, co-founder of Untapped Energy. The conversation explores what it really means to build AI literacy and fluency inside organizations, and why so many teams struggle to move from experimentation to impact.
Tim shares why data remains the foundation of any effective AI strategy, how businesses can bridge the gap between curiosity and capability...
In the first episode of Season 2 of the Sell Me This Podcast, host Keith Daser talks with Shawn Freeman. From starting and scaling organizations to navigating leadership challenges, Shawn shares what he’s learned from years of building teams and driving growth in a changing industry.
They discuss how the MSP model is evolving, what strong leadership looks like in today’s tech landscape, and how forward-thinking companies c...
On the season finale of the Sell Me This Podcast, host Keith Daser talks with Ian Macdonald, Business and Innovation Leader at KPMG Canada. In this wide-ranging conversation, they explore the intersection of innovation, risk, and why Calgary is emerging as one of Canada’s most dynamic tech hubs.
Ian shares why he believes imagination and curiosity are often overlooked in business, and how those traits have shaped his appro...
On this episode of the Sell Me This Podcast, Keith Daser talks with Cassie Jeppson, Director of Channel Programs and Operations Strategy at Lenovo. From hobby-farming in Tennessee to leading one of North America’s largest channel teams, Cassie has a diverse background that informs her dynamic perspective on leadership, technology, and the evolving partner ecosystem.
They dive into her journey across marketing, sales, and e...
On this episode of the Sell Me This Podcast, Keith Daser talks with Tim Thomson, former MSP founder, business coach, and the creator of Cyber Trends. After scaling his managed services company to over $7 million in revenue, Tim learned the kinds of lessons that rarely make it into conference keynotes or LinkedIn posts.
They dig into the real challenges MSPs face as they grow, what separates those that scale from those that...
On this episode of the Sell Me This Podcast, Keith Daser talks with Matthew Nielsen, founder and CEO of Ethicrithm and former CEO of Fishbone Analytics. With decades of experience in IT outsourcing, enterprise analytics, and digital transformation, Matthew shares how turning customer frustrations into solutions helped him build and scale a thriving business.
They explore the key decisions that fueled Fishbone’s growth and ...
On this episode of the Sell Me This Podcast, Keith Daser talks with Scott Coleman, Enterprise Account Executive at Arctic Wolf, a leader in cybersecurity operations. From the intensity of capital markets to the fast-moving world of tech sales, Scott’s path has been anything but typical, and it’s shaped how he builds trust, earns attention, and navigates complex deals.
They dive into the evolving landscape of modern cyberse...
Join us for a conversation with Lindsay Smylie, Director at Plug and Play Alberta, one of the world’s most active seed-stage investors and startup accelerators. With a background that ranges from corporate energy to craft distilling, Lindsay brings a unique lens to entrepreneurship, innovation, and building thriving business ecosystems.
We explore her transition from jumping headfirst into startups to leading efforts that ...
Explore the real-world challenges technical founders face when scaling managed services businesses with Todd Kane, founder of Evolved Management Consulting and a seasoned voice in MSP leadership. Drawing from years of operational expertise, Todd unpacks the critical gaps that often emerge as small, founder-led teams evolve into structured, process-driven organizations.
We dive into the transition from reactive firefighting...
On this episode of the Sell Me This Podcast, host Keith Daser is joined by Dustin Cassar to break down MSPs, what they are, how they are more than just IT, and partner selection.
You can find Dustin at: https://www.linkedin.com/in/dustincassar/
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