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What does cybersecurity look like when the stakes are patient lives, not just data? Joseph Davis is the Chief Security Advisor at Microsoft for health and life sciences. He has over 30 years in IT and cybersecurity and advises healthcare CISOs and hospital boards. He describes his job as translation: turning the global threat landscape into decisions a health system can act on. In this episode, Joseph covers: - Securing critical medical devices that can never be taken offline - Network segmentation and designing the blast radius before an incident - Why health systems should measure continuity, not just prevention - Using personal devices as a pre-planned, out-of-band communication channel - Identity compromise and AI-driven attacks on legacy systems - The autonomous AI analyst he wishes existed today The 808 AI Podcast: four questions, eight minutes and eight seconds, because 808 looks like Bob. Connect with Joseph on LinkedIn: Joseph Davis, Microsoft Microsoft Security Blog: https://www.microsoft.com/en-us/security/blog/

Is your business chasing new customers when the real growth is sitting in your current client list? In this episode of the 808 Podcast, Bob Clark talks with Justin Esgar, owner of Virtual Computers, an Apple Authorized Consultant and Apple-focused MSP based in New York with offices across the United States. Justin also runs the ACES conference for Apple IT business owners, now heading into its 13th year and opening to PC providers. Justin breaks down the mistake he sees IT companies make again and again, why working your existing customers beats paying for marketing, and how AI is creating a huge opportunity for IT providers to help clients make more money. He also shares why he believes Macs are safer by design, recommends three future guests, and explains why he wants AI to run his business, but only if it does it his way. Four questions. Eight minutes and eight seconds. Because 808 looks like BOB. Learn more: https://www.virtualcomputers.com/

What are people not thinking about when it comes to data privacy? In this episode of the 808 Podcast, Bob Clark talks with Jeremy Cunningham, an IT professional with 30 years of experience spanning software development, security management, data governance, and SaaS management. Jeremy explains how much data people give away without knowing it, including websites that record deleted form entries and social platforms that track when you pause on content. He makes the case for going online with intention and purpose, and shares Linkwarden, an open source tool for syncing bookmarks under your own control. Jeremy also recommends a future guest, Andrea Goulet, who connects software engineering and psychology to help people improve how they interact. And he shares what he wishes AI could do better: spend less time making people double-check its work. Four questions in eight minutes and eight seconds, because 808 looks like Bob.

What does a Beatles producer’s ear teach you about running a business in the age of AI? Mark Berry is Chairman of AMG Corp and AMG Visuals, a Toronto-based music, film, and television company with an extensive publishing catalog. AMG places music in film, television, video games, ad campaigns, movie trailers, and Spotify playlists, distributes through Universal Music, and supplies the music you hear in retail stores worldwide. Mark began his career at 18 at AIR Studios, owned by Sir George Martin, working sessions like the Live and Let Die soundtrack. In this episode, he shares the lesson he learned watching Sir George catch phase cancellation by ear in a full orchestra, and how that same trained ear guides how AMG uses AI today. Through AttackTrax, AMG produces AI orchestral scores for film, reducing the cost of live orchestras while gaining the ability to make changes instantly. Mark also previews Sweat It Out, an upcoming documentary on the late 60s and early 70s Australian pub rock scene featuring early AC/DC, Jimmy Barnes, INXS, and Midnight Oil. The 808 Podcast: four questions in eight minutes and eight seconds, because 808 looks like Bob. Mark Berry: https://theamgcorp.com/AMG Visuals: https://amg-visuals.com/

Why do so many talented experts stay invisible online? EJ Bowen, serial entrepreneur, helps business owners, consultants, and fractional executives become visible and win business on LinkedIn. In this episode of the 808 Podcast, he explains why most LinkedIn profiles read like digital resumes, why roughly 80% of the platform’s content is noise, and how taking a clear stance helps experts stand out and spark real engagement. EJ also shares a referral for a future guest, describes his dream AI employee, and closes by asking how the 808 Podcast got him to say yes, which turns into a sharp lesson on value-first outreach. Four questions. Eight minutes and eight seconds. Because 808 looks like BOB. Learn more: https://omnilegion.com/

What should businesses do before handing their data to AI? Dave Jooste, President of the MSPAA, joins Bob Clark on the 808 Podcast to talk about the state of AI in business. Dave explains why fields like accounting and healthcare need AI governance now, shares his two-step approach of monitoring first and then defining rules, and describes his bigger vision for AI that can coordinate work across many connected systems. In the second half, Dave turns the tables and asks Bob how MSPs can build visibility. Bob explains why a short local podcast is one of the easiest and cheapest networking tools a business can have. Four questions. Eight minutes and eight seconds. Because 808 looks like BOB. Connect with Dave and the MSPAA:Website: https://mspaa.net/

What are business owners still doing on LinkedIn that stopped working years ago? Mike O'Neil, The LinkedIn Rock Star, has spent 20 years helping companies, sales teams, and professionals use LinkedIn to find customers. In this episode of the 808 Podcast, he explains which old LinkedIn habits are wasting your time and what to do instead. In this episode: Why LinkedIn groups are dead for engagement but still valuable for targetingHow to use group membership as a search filter to find people interested in your topicWhy "we're in the same group" and "mutual connection" outreach gets ignoredHow Mike's AI app, LinkedSuite, scores your connections to find decision makersWhy manual, personal engagement beats mass messagingHow Mike met his wife on LinkedInMike's app grew out of a project with 28 Mercedes-Benz outside sales reps. It helps users find the right people and engage with them without breaking LinkedIn's sending rules. Connect with Mike: https://schedulewithmike.com/ The 808 Podcast: four questions in eight minutes and eight seconds, because 808 looks like BOB. Hosted by Bob Clark.

Is your business really too small to be a target, or is that belief what puts you at risk? On this episode of the 808 AI Podcast, Bob Clark talks with Adam Goldstein of ATEC Business Services, a nationwide managed IT service and cybersecurity provider based in New York City that has been in business for twenty years. Adam explains why small businesses that assume nobody wants their data are often the most attractive targets for attackers. He also covers the simplest, least expensive protection available, multi-factor authentication, and why the industry is moving away from SMS codes and tap-to-approve prompts toward methods that make users pay attention. Adam also shares his dream AI employee, one that pushes back on bad ideas and knows when a support ticket needs to be escalated. He finishes with a story about how ATEC grades potential acquisitions for a medical practice management client and how that grade helps set the offer price. Four questions. 8 minutes and 8 seconds. Because 808 looks like Bob. Guest website: https://atecbusiness.com/

Before your business turns on AI, you need to know what it can see. Ed Eisenstein, owner of United Network Associates, a national cybersecurity and managed security services company in Farmingdale, New York, joins Bob Clark to explain how tools like Microsoft Purview and smart data segmentation keep sensitive information from surfacing where it shouldn't. Ed draws on 26 years in cybersecurity and eight years as a county CIO to explain why government faces the steepest climb toward AI readiness. He also describes his dream AI employee: one that challenges his thinking instead of agreeing with him. The 808 Podcast: four questions in eight minutes and eight seconds, because 808 looks like Bob. Learn more: https://unatech.us/

Does your IT company only show up when something breaks? Rick Welch says that's a problem. Rick, Founder and CEO of Spark Technologies, explains why "keeping the computers running" stopped being enough years ago, what proactive IT should include today, and why your provider needs to understand your industry, not just your hardware. He also shares how his team uses AI to work faster without replacing anyone. 🎧 After you listen, tell us: what's one thing you wish your IT provider did better? Leave a review or comment and let us know. Spark Technologies is an IT service and cybersecurity company in Rockland, Massachusetts, serving small and medium-sized businesses.https://sparktechllc.com/ The 808 Podcast: four questions in eight minutes and eight seconds, because 808 looks like Bob.

Darrick Richardson, Managing Partner at GreySolve Consulting, joins the 808 Podcast to talk about identity security for mid-sized companies. GreySolve provides automated, AI-based identity security solutions that bring enterprise-scale protection to mid-market businesses. Darrick explains why mid-sized accounting and legal firms are a favorite target for hackers, why security often gets ignored until something goes badly wrong, and the basic steps any company can take right now: clean onboarding and offboarding, regular access reviews, and multi-factor authentication for everyone, especially leadership. He and Bob also dig into AI voice cloning scams, a real attempt on Bob's grandmother, and simple ways to spot a fake call before it costs you. Four questions. Eight minutes and eight seconds. Because 808 looks like BOB. Learn more about GreySolve Consulting: https://www.greysolve.com/

Bill Campbell, owner of Balancelogic and ITAssurance, joins the 808 Podcast to explain the difference between a managed services provider (MSP) and a managed technology provider (MTP): one handles the day-to-day execution of your IT, the other aligns your technology with where your business is going over the next 12 to 24 months. From there, Bill gets practical about AI. He shares how he uses AI agents for engineering, marketing, and sales, how he builds internal and client web apps, and his two-tool prompt workflow using ChatGPT and Claude. He also walks through his AI board of advisors, built with detailed company context and one key instruction: don't be a yes man. Plus, why AI lets businesses mold their software around how they work, instead of molding their business around the software. Four questions. Eight minutes and eight seconds. Because 808 looks like Bob. Connect with Bill:Website: https://balancelogic.com/Newsletter: Balancelogic Insider, https://balancelogic.com/balancelogic-insider/

Alex Branning builds tools for insurance agents. He is best known for Agent CRM and the Loanne voice AI platform, and he lives and breathes insurance marketing. In this episode of the 808 AI Podcast, Alex answers the question every agent should be asking: how can an insurance agent safely use AI? His warning is blunt. There are people deliberately trying to trick AI voice and text bots into saying something an agency will regret, and an agent who builds their own tool without proper guardrails is setting up a very expensive case. Alex explains what those guardrails look like and why plug-and-play beats DIY. Also in this episode: the ADA lawsuit parallel, what Alex wishes AI could do about client churn, his guest pick for a future 808, and why he says writing a book gave his business more authority than AI ever could. Four questions. Eight minutes and eight seconds. Because 808 looks like BOB. Get Alex's free book: https://Freebook.InsuranceCMO.AI/

On this episode of the 808 Podcast, Bob Clark sits down with Taylor Dondich, founder of FellowHire, for four questions in eight minutes and eight seconds. Taylor breaks down the biggest hidden cost in AI adoption: token consumption. As companies connect more tools to their AI systems and adopt smarter, more capable models, spend quietly climbs, often without anyone noticing until it's a real problem. He shares why observability and fixed-cost vendor pricing matter more than most companies realize, and why compliance and data sovereignty can't be an afterthought when bringing on a new AI vendor. Taylor also talks about FellowHire's approach: AI "fellows" that work alongside human team members rather than replacing them, and why he believes the companies leaning into human-plus-AI collaboration are outperforming the ones that bet on full automation. Learn more about FellowHire at fellowhire.com.

Most companies turn on AI and then find out what it can see. Ed Eisenstein says that order is backwards. Ed is the owner of United Network Associates Inc. in Farmingdale, New York, a national cybersecurity and managed security services company with about a dozen specialist engineers and 26 years in business. He is also an 8 year veteran CIO for a New York county, which gave him a front row seat to the data problem almost nobody talks about before an AI rollout. In 8 minutes and 8 seconds, Ed covers: Why the files sitting on your network are being used to train AI right now, and what indexing actually preventsMicrosoft Purview, and how it flags critical information inside your files before anything gets searchedWhy segmenting accounting, sales, and marketing data is step one, not step fiveThe example that lands hardest: staff seeing the owner's salary, not because anyone went looking, but because the AI indexed itWhy local government holds the worst unstructured data problem in the countryWhat Ed wants from a dream AI employee, and why being agreed with is the part that scares himGuest: Ed Eisenstein, United Network Associates Inc. Website: https://www.unatechnical.com/ The 808 Podcast is four questions in 8 minutes and 8 seconds, because 808 looks like BOB. Host Bob Clark interviews business owners, CEOs, executives, and whoever else he feels like.