A Tech Entrepreneur Talks AI Threats, World-Class Customer Experience, and ROI - with Orion Stewart

What does it really take to build a business where customer service isn’t just a buzzword, but the heartbeat of everything you do? In this episode, Sean O’Hara sits down with Orion Stewart, co-founder of MSP Shift, to unpack his entrepreneurial journey and the lessons he’s learned along the way. From knowing when it’s the right time to bring in IT support, to why outsourcing often makes more sense than hiring in-house, Orion shares honest, practical advice for business owners who want to scale the smart way. They also dive into the challenges every modern business faces—like the growing wave of AI-driven cybersecurity threats—and how to stay one step ahead. Whether you’re just starting out or looking to tighten up your IT and customer experience, this conversation is packed with real-world insights and tips you can put into practice right now. KEY TAKEAWAYS Customer Service as a Core Focus: Emphasizing that customer service should be the primary focus of any business, not just an add-on. Building strong relationships with customers is essential for long-term success. Importance of IT Support for Small Businesses: Many small businesses face challenges as they grow, particularly in IT. Outsourcing IT services can provide better ROI compared to hiring in-house staff, especially for companies that are scaling rapidly. Cybersecurity Threats: Small businesses are increasingly vulnerable to cybersecurity threats, with a significant rise in attacks reported. It's crucial for businesses to invest in proper IT support to safeguard against these risks. AI's Dual Role: While AI can enhance cybersecurity measures by identifying vulnerabilities, it also poses new threats as attackers can use AI to create more sophisticated phishing attacks. Business owners need to be cautious about the data they share with AI models. Building a Strong Team: A successful IT team should balance technical expertise with strong customer service skills. Hiring individuals who can connect with clients and understand their needs is vital for providing effective IT solutions. BEST MOMENTS "Customer service can't just be something that you slap on your website or put on your business card. It has to be the primary focus in whatever industry you're going into." "We are seeing a massive rise on attacks on the small business space. Cisco actually reported a 60% increase on the SMB space" "If you are using AI models within your business, make sure you're paying for a business license and whatever AI model that you're using isn't going to use your data for future learning models." "The scary part is if an AI bot is now beating some of the top security engineers in finding these bugs and vulnerabilities, if it's in the right hands, then that's amazing. The scary part is if it gets into the wrong hands." HOST BIO Meet Your Host: Sean O’Hara, MBA – Entrepreneur, Sales Strategist, and Relentless Business Optimist. With over 20 years in the entrepreneurial trenches—guiding scrappy startups and Fortune 1000 giants alike—Sean brings a rare mix of strategic insight and real-world experience to every conversation. Known for his sharp sales acumen and down-to-earth style, he doesn’t just talk business—he lives it. Sean’s superpower? Asking the right questions, then stepping back to let the wisdom flow. His curiosity-driven interview style unlocks actionable insights, powerful stories, and the kind of truth today’s entrepreneurs actually need. If you’re serious about building a business that lasts, Sean’s the guide you’ll want in your corner. This Podcast has been brought to you by Disruptive Media. https://disruptivemedia.co.uk/