Enhancing AI Literacy for IT Professionals: An Interview with Leslie Dewey
SMB Community Podcast by James Kernan
Release Date: 10/27/2025
New Years: 2026 Strategy/Planning
SMB Community Podcast by James Kernan
Overview: In this episode of the SMB Community Podcast, hosts Amy and James discuss the importance of timely year-end planning for IT professionals, suggesting October as the ideal start time for preparation. They cover effective strategies for developing annual goals, emphasizing the need for a personalized approach and tactical objectives. The hosts also examine the recent cloud outages from AWS and Azure, stressing the importance of diversifying cloud services. They touch on the growing presence of AI in technology and its implications for MSPs. Additionally, they explore the upcoming 50th...
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How To Finish The Year Strong
SMB Community Podcast by James Kernan
Overview: In this episode of the SMB Community Podcast, hosts Amy and James discuss strategies for IT professionals to finish the year on top, including sales tips, inventory reduction, and tax advantages through IRS Tax Code Section 179. They also delve into the feasibility and future of humanoid household robots, debating their practicality and cost. Additionally, they touch on industry news such as the rising dominance of AMD processors, recent Microsoft 365 outages, and the importance of outcome-based funding over traditional MDF. The episode wraps up with details on an AI class and an...
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Enhancing AI Literacy for IT Professionals: An Interview with Leslie Dewey
SMB Community Podcast by James Kernan
Overview: In this episode of the SMB Community Podcast, hosted by James Kernan, special guest Leslie Dewey, CEO of Sweetwater Street, shares her expertise on artificial intelligence (AI). Leslie discusses her background in media and security, which led her to a passion for AI. She provides insights into AI literacy, automation benefits, and practical tips for business owners to integrate AI into their operations. The conversation also covers the importance of AI training, the challenges of data security, and ways to leverage AI as a competitive advantage. Leslie emphasizes the need for...
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Exploring Cyber Risk Management: An Interview with Kevin Schmidt
SMB Community Podcast by James Kernan
Overview: In this episode of the SMB Community Podcast, James Kernan interviews Kevin Schmidt from Coalition. They discuss the importance of cybersecurity and cyber risk management, focusing on Coalition's comprehensive approach that integrates cyber insurance with cybersecurity solutions. Kevin highlights the unique aspects of Coalition’s services, which include active insurance and real-time risk assessments. He explains how their platform helps service providers discuss cybersecurity as a business risk, emphasizing the financial impact of cyber incidents on SMBs. Kevin also outlines...
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Optimizing Monthly Cashflows for MSPs
SMB Community Podcast by James Kernan
Overview: In this episode of the SMB Community Podcast, hosts James and Amy discuss weekend highlights and then dive into crucial advice for improving monthly cash flow for Managed Service Providers (MSPs). They emphasize the importance of collecting payments upfront, managing monthly subscription income, and understanding monthly burn rates. They also cover consumer insights, including the rise of 'silver startups' among older generations and increasing tech budgets for cloud, cybersecurity, and AI. Finally, industry updates include the appointment of a new VP of Global Channel Sales at...
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Maximizing AI: Leverage and Monetization
SMB Community Podcast by James Kernan
Overview: In this episode of the SMB Community Podcast, hosts Amy and James discuss the monetization of AI for MSPs, leveraging existing skills and tools such as Microsoft Copilot and ChatGPT. They encourage MSPs to differentiate themselves by adopting AI technologies and utilizing available marketing funds. The hosts address the potential lapse of the CISA Act, the importance of upgrading to Windows 11, and California’s new AI legislation. They also highlight changing buyer demographics and emphasize the need for modern engagement strategies. Additionally, the show covers recent news,...
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Results for MSPs: An Interview with Sam Saab and Bob Lewis
SMB Community Podcast by James Kernan
Overview: Exploring Results Software with CEO Sam Saab and CRO Bob Lewis In this episode of the SMB Community Podcast, host James Kernan interviews Sam Saab, CEO and Founder, and Bob Lewis, Chief Revenue Officer of Results Software. The discussion covers the origins of the company, the features and functionalities of their software, and their focus on servicing various industry verticals such as construction, field services, and professional services. They elaborate on the company's a la carte licensing model, their channel partner program, and provide insights into the types of clients who...
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Purchasing Local Competition: Is It Worth It?
SMB Community Podcast by James Kernan
Overview: In this episode of the SMB Community Podcast, hosts James and Amy are back to discuss a wide range of topics relevant to the MSP community. The episode begins with professional insights, starting with advice on purchasing a local competitor MSP and moving on to broader industry trends. They discuss the impact of major companies restructuring for AI, changes in H-1B visa regulations affecting tech workers, and Microsoft's new return-to-office policy. The episode wraps up with discussions on upcoming economic indicators and opportunities for MSPs to thrive despite broader economic...
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Microsoft Partner Program Changes & Updates
SMB Community Podcast by James Kernan
Overview: In this episode of the SMB Community Podcast, hosts Amy and James discuss a variety of tech topics relevant to IT professionals. They start by sharing personal anecdotes about their preferences for coffee and tea before diving into recent changes in the Microsoft Partner Program, emphasizing the importance of meeting revenue requirements. The conversation then shifts to Oracle's headquarters' growth, AI investments, and its significant role in database management. They also highlight leadership changes aimed at making Kase AI-focused. The discussion covers Apple's recent product...
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Navigating Pricing Models
SMB Community Podcast by James Kernan
Overview: In this episode of the SMB Community Podcast, hosts Amy and James discuss various topics relevant to the IT professional community. A significant segment is dedicated to addressing the ongoing debate of per seat versus per device pricing models in Managed Service Providers (MSP), emphasizing the evolving nature of MSP pricing strategies. The hosts further explore the economy's impact on MSPs, highlighting opportunities for growth and hiring during downturns. They also delve into the underestimated risks and potential of AI technology in business, covering recent research on AI...
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In this episode of the SMB Community Podcast, hosted by James Kernan, special guest Leslie Dewey, CEO of Sweetwater Street, shares her expertise on artificial intelligence (AI). Leslie discusses her background in media and security, which led her to a passion for AI. She provides insights into AI literacy, automation benefits, and practical tips for business owners to integrate AI into their operations. The conversation also covers the importance of AI training, the challenges of data security, and ways to leverage AI as a competitive advantage. Leslie emphasizes the need for responsible AI use and offers guidance on navigating the rapidly evolving AI landscape.
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Chapter Markers:
00:00 Introduction to the SMB Community Podcast
00:43 Meet Leslie Dewey: AI Guru and CEO of Sweetwater Street
01:13 Leslie's Journey into AI and Security
01:57 Sweetwater Street's Mission and AI Literacy
04:09 AI in Business: Benefits and Applications
05:57 Tips and Tricks for Using AI Tools
09:03 Deep Research and Competitive Analysis with AI
11:22 Monetizing AI and Data Security Challenges
15:46 Conclusion and Contact Information
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New Book Release:
I'm proud to announce the release of my new book, The Anthology of Cybersecurity Experts! This collection brings together 15 of the nation's top minds in cybersecurity, sharing real-world solutions to combat today's most pressing threats.
Whether you're an MSP, IT leader, or simply passionate about protecting your data, this book is packed with expert advice to help you stay secure and ahead of the curve.
Available now on Amazon!
https://a.co/d/f2NKASI
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Sponsor Memo:
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