Jeremy Cunningham

Should you bring on a business partner, or just collaborate?Thomas Ladegaard is a San Diego business attorney with 22 years of experience in transactional law and business litigation. He sets up companies, writes contracts, registers trademarks, serves as general counsel, and represents clients when business relationships fall apart.In this episode, Tom explains:- Why a business divorce can be as messy and expensive as a marital one- The three things a real partner must bring: capital, technical know-how, or relationships- Why rewarding a great employee with equity can backfire, and what to offer instead- What he wishes AI would stop doing, and why lawyers must verify every citation- Why you sometimes need to slow down to speed upFour questions in eight minutes and eight seconds, because 808 looks like BOB.Thomas Ladegaard: https://ladegaardlaw.com/

Should business owners fear AI, or put it to work?Bill Dickherber, President of Onsite Computer Consulting Services Inc., runs a managed IT and cybersecurity provider serving clients across Missouri, Illinois, and beyond. With AI data centers being built across the St. Louis area, Bill shares why he tells clients to focus on what AI can do for them, not to them.In this episode:- Reframing the AI fear conversation for business owners- How attackers use AI to get around security, and why diligence still matters- Why dental practices are among the quiet AI adopters- Why AI output still needs a human in control- The data center debate, and why resistance tends to fadeFour questions in eight minutes and eight seconds, because 808 looks like Bob.Learn more: https://www.occsi.com/

Why do smart firms keep wasting money on technology that never sticks?Brian Murray is the owner and "top tinkerer" of Agile Networks, an IT firm that has served architecture firms exclusively for 20 years. In this episode, Brian explains technology whiplash, the cycle of switching tools until the team is split across systems and too fatigued to adopt the one that would actually work. His fix: plan it, map it, and pilot before rolling anything out.Brian also shares why a career in tech taught him that trust matters more than technology, how he went from mechanical engineering to social work to Harvard's Graduate School of Design, and why he thinks of AI as your most earnest intern. Plus, he introduces Barkitecture, where architects design and auction dog houses for animal rescues.Four questions. Eight minutes and eight seconds. Because 808 looks like Bob.Guest website: https://agilenet.works/

Why do so many MSPs struggle to turn great technical work into profit?Tim Coach, Chief Evangelist of Community and Channels at Cynomi, joins Bob Clark on the 808 Podcast. With 30 years in IT, from engineer to running and rebuilding MSPs, Tim now helps MSPs, MSSPs, and IT service providers grow through process and efficiency.In this episode:- The number one mistake MSPs make: speaking tech jargon instead of business language- Real examples of industry lingo that builds instant credibility- Why customization is the death of revenue, and how standardization lets you scale- The AI "pick a number" experiment, and why humans still need oversight- How Cynomi helps make the CISO role more efficient with security managed to a baselineFour questions. Eight minutes and eight seconds. Because 808 looks like Bob.Learn more: https://cynomi.com/Connect with Tim: https://www.linkedin.com/in/tim-coach/

Is digital lead generation getting harder, or is it just getting crowded?Nicole Bielanski, Growth Coach at Iceberg Cyber, helps MSPs generate leads for managed services. In this episode, she breaks down human to human lead generation: identifying ideal clients from your existing book of business, mapping them within a few miles of your office, and walking in with donuts and a simple cyber score that only requires the company's domain.We also cover why somebody has to like you before a relationship starts, a prompting trick for getting AI to understand your vision, and why a short podcast can be one of the best networking tools around.Four questions. Eight minutes and eight seconds. Because 808 looks like BOB.Learn more about Iceberg Cyber: https://icebergcyber.com/

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 todayThe 808 AI Podcast: four questions, eight minutes and eight seconds, because 808 looks like Bob.Connect with Joseph on LinkedIn: Joseph Davis, MicrosoftMicrosoft 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/