Stack And Startup Baltimore

Growing a business is exciting—until the technology that helped you get started begins slowing you down. In this episode of Stack & Startup – Al Fresco, Jason Sherwood discusses one of the biggest challenges facing growing businesses: knowing when it's time to move beyond "good enough" technology and begin building systems that support long-term success. Whether it's networking, cybersecurity,...

Healthcare is one of the most human industries in the world, but behind every patient visit is a system most people never see. In this episode of Stack & Startup, Jason Sherwood sits down with Dr. Mikel Daniels of WeTreatFeet Podiatry and The Podiatry Voice to discuss how AI, documentation, cybersecurity, HIPAA, trust, and human care all collide inside a modern medical practice. We discuss: •...

If your business has more than a handful of employees, there is a good chance AI is already being used somewhere inside your organization. Maybe it's helping write emails. Maybe it's summarizing notes. Maybe it's drafting proposals. Maybe it's creating marketing content. The question is no longer whether businesses should use AI. The question is whether businesses are governing it intentionally. I...

Most people do not fail because they lack ideas. They fail because execution is harder than inspiration. In this episode of Stack & Startup, Jason Sherwood sits down with Phil Parsons of KP Homescapes to discuss the systems, discipline, and leadership required to consistently turn ideas into finished results. From engineering and Department of Defense work to construction leadership and AI-dri...

What would actually happen if your business lost all of its data tomorrow? Not just one file. Not just one computer. Everything. In this episode of Stack & Startup: Al Fresco, Jason Sherwood walks through the real-world business impact of catastrophic data loss and why preparation—not panic—is what separates disruption from disaster. Topics include: • What "losing everything" actually means •...

Everybody says relationships matter in business. But most people treat relationships like a tactic. A follow-up email. A LinkedIn connection. A networking event. A stack of business cards. In this episode of Stack & Startup Baltimore, I sit down with Andy Kobus of United Rentals to discuss what actually creates trust, how reputation compounds over time, and why genuine relationships still outp...

Most business owners think a cyberattack is unlikely. Until it happens. In this episode of Stack & Startup: Al Fresco, Jason Sherwood explores a simple but important question: How close is your business to a major disruption? Drawing on industry research, real-world experience, and practical cybersecurity principles, this episode walks through five warning signs that your organization may be m...

Most business owners do not run out of ambition. They run out of visibility. In this episode of Stack & Startup Baltimore, I sit down with Crystal Baze Barney, CPA and founder of Journey Business Accounting, to discuss sustainable growth, financial visibility, modern business systems, leadership, technology, and what really happens when a company grows faster than its infrastructure. We talk a...

Most businesses believe they have backups. Far fewer know whether those backups actually work. In this episode of Stack & Startup: Al Fresco, we discuss one of the most overlooked risks in business technology: untested backups. Because a backup is not about storage. It is about recovery. We cover: • Why successful backup reports can create a false sense of security • The most common reasons ba...

Most business owners think legal problems start in a courtroom. According to attorney Shavon Smith, they usually start much earlier. In this episode of Stack & Startup Baltimore, Jason Sherwood sits down with Shavon J. Smith of The SJS Law Firm to discuss why legal issues often begin as operational issues, contract gaps, documentation failures, and communication breakdowns. We discuss: • Why f...

Cloud vs Local: Which Is Better for Your Business? Everyone seems to have an opinion about cloud computing. Some people say everything belongs in the cloud. Others insist that local servers are still the better option. The truth is more complicated. In this episode of Stack & Startup: Al Fresco, we break down the real advantages and disadvantages of cloud infrastructure, local servers, and hyb...

The cheapest IT setup is easy to find. The smartest one is not. In this episode of *Stack & Startup: Al Fresco*, we break down the difference between cheap IT, overbuilt IT, and intentionally designed systems that actually fit the business they support. Because technology decisions are not just about cost. They are about: • operational friction • scalability • reliability • security • and long...

The cheapest IT setup is easy to find. The smartest one is not. In this episode of *Stack & Startup: Al Fresco*, we break down the difference between cheap IT, overbuilt IT, and intentionally designed systems that actually fit the business they support. Because technology decisions are not just about cost. They are about:  • operational friction  • scalability  • reliability  • security  • and...

“My IT guy has it handled. ”That sounds reassuring. But it is not a strategy. In this episode of Stack & Startup: Al Fresco, we break down the hidden risks of relying on a single person to manage your entire IT operation—and why structure matters more than individual capability. Because the problem is usually not the person. It is the lack of systems around them. We talk about: • single points...

If your business relies on technology—then this affects you. Right to repair is not just about fixing devices. It is about control. Control over your systems. Control over your costs. And control over how quickly your business can recover when something breaks. In this episode of Stack & Startup: Al Fresco, we break down what right to repair actually means—and why it has real consequences for...

Outdated systems do not usually break your business. They slow it down. And over time, that becomes expensive. In this episode of Stack & Startup: Al Fresco, we break down the hidden cost of outdated systems—how small inefficiencies, slow workflows, and disconnected tools quietly reduce performance across your business. Because the biggest risk is not failure. It is friction. 💡 In this video:...

Most failures do not start as big problems. They start small. They get missed. And by the time the damage shows up, the real cause may already be buried. In this episode of Stack & Startup, I sit down with Priyanshu Banerjee, a materials scientist and project manager at Anderson Materials Evaluation in Columbia, Maryland. We talk about failure analysis, material testing, bad assumptions, calib...

For years, the narrative around millennials has been consistent: They are entitled.  They avoid risk. They are not built for business. But when you actually look at the data—that story does not hold. In this episode of Stack & Startup: Al Fresco, we break down the real advantages millennial founders have in today’s business environment—from adaptability and tech fluency to survival rates and b...

Most small businesses are losing money through their IT—just not in obvious ways. It is not major outages or dramatic failures. It is the small, everyday decisions that quietly create inefficiencies, increase risk, and slow down growth over time. In this episode of Stack & Startup: Al Fresco, we break down three common IT mistakes that cost businesses money—and what you can do to fix them. If...

Starting a business comes with a lot of uncertainty—but one of the biggest challenges isn’t external. It’s internal. Imposter syndrome shows up early for a lot of entrepreneurs. That feeling that you are not ready, not qualified, or somehow “faking it” is more common than most people realize.  In this episode of Stack & Startup: Al Fresco, we break down what imposter syndrome really is, why it...

Starting a business during an economic downturn might sound risky, but it may actually be one of the smartest moves you can make. In this episode of Stack & Startup: Al Fresco, we break down why tough economic times create unique opportunities for entrepreneurs, how to position yourself for long-term success, and what most people get wrong when they wait for “the perfect time.” If you are thin...

🌿 Stack & Startup Al Fresco: The Podcast Method for Marketing Welcome to the first Al Fresco edition of Stack & Startup — where we take business conversations outside and dive deep into a single powerful idea. In this episode, Jason Sherwood breaks down The Podcast Method for Marketing — a strategic approach to building authority, creating meaningful relationships, and generating real bus...

Connect With Us On LinkedIn Jason Sherwood - https://www.linkedin.com/in/jason-m-sherwood/ Kathleen Sherrill - https://www.linkedin.com/in/kathleen-sherrill-sp-arch-inc/ 📌 Project Management with Kathleen Sherrill Dive into this practical and insightful session on project management with Kathleen Sherrill — perfect for students, professionals, and anyone looking to sharpen their planning, executi...