Stack And Startup Baltimore

Real estate development can begin with a deceptively simple question: Where? But finding the right commercial site can take months — sometimes years. Parcel information may live in one place. Zoning somewhere else. Infrastructure data somewhere else again. And a decision that looks simple on a map can put millions of dollars at risk. In this episode of Stack & Startup Baltimore, Jason Sherwood...

AI isn't just one thing anymore. For most businesses today, AI means opening a website or an app, typing a prompt, and letting somebody else's infrastructure do the work. But increasingly, AI can live in different places. In the cloud. On local hardware. Inside private business systems. Or across a combination of all three. And where AI runs matters. In this episode of Stack & Startup: Al Fres...

Real estate can look simple from the outside. Buy a property. Renovate it. Sell it or rent it. Move on to the next one. The reality is a lot more complicated. In this episode of Stack & Startup Baltimore, Jason Sherwood sits down with Brooke Gibson, Founder and Principal of Gibson Private Capital, to talk about what actually happens behind the numbers. Brooke brings more than two decades of ex...

One of the most dangerous phrases in business is: “It’s just temporary.” There is nothing inherently wrong with a workaround. Businesses have to move quickly. Problems happen at inconvenient times, customers still need answers, and sometimes the perfect solution simply isn't available. The problem comes when nobody goes back. The spreadsheet created as a quick fix becomes business-critical. The sh...

Your business can look perfectly healthy right up until the moment one overlooked dependency fails.   Technology matters, but business resilience is bigger than technology. People, vendors, processes, accounts, documentation, institutional knowledge, and outside services can all become critical dependencies. If the business can't function when one of them suddenly disappears, that isn't just an in...

A $20 software subscription does not look like a business problem. Neither does a $50 tool somebody needed for a project. Or the platform someone signed up for six months ago and forgot about. But eventually, those decisions start adding up — and not just on the credit card statement. In this episode of Stack & Startup Al Fresco, I talk about subscription creep: the slow accumulation of softwa...

Artificial intelligence is becoming part of nearly every business conversation. The problem is not the technology. The problem is how people choose to use it. In this episode of Al Fresco, I explore why AI should strengthen your judgment instead of replacing it. Whether you're writing emails, creating policies, making strategic decisions, or solving customer problems, AI can accelerate your work—b...

Cancer research is one of the hardest entrepreneurial journeys imaginable. Long development cycles, scientific uncertainty, fundraising, regulatory hurdles, and the hope of improving lives all collide in one mission. In this episode of Stack & Startup, Jason Sherwood sits down with Roman Owens, Co-Founder & CEO of OncoVanta Therapeutics, to discuss what it really takes to build a biotech s...

At some point, every growing business reaches a stage where things that once worked perfectly begin creating friction. It takes longer to find information. Communication becomes more difficult. Processes require more work than they should. The business hasn't become worse—it has simply outgrown the systems that once supported it. In this week's Al Fresco Friday, I discuss how operational friction...

The future of healthcare may not be about making people travel further for care. It may be about bringing more healthcare to the people who need it. In this episode of Stack & Startup, I sit down with Charlie Nahabedian, founder of VK Digital Health, to discuss the decades-long journey that led him to rethinking how healthcare is delivered. We explore: • Building businesses with long-term visi...

Every business owner has said it. "It's working fine." Sometimes that's true. Sometimes it's the warning sign you only recognize after something breaks. In this episode of Stack & Startup Al Fresco, I explore one of the most common mindsets that quietly creates operational risk inside businesses. Whether it's undocumented processes, aging technology, tribal knowledge, or a single employee who...

For years we've heard that artificial intelligence would transform the way we work. But what does that actually look like in the real world? In this episode of Stack & Startup, Jason Sherwood sits down with Dowdy Jackson, PhD, Chief Scientific Officer at Antigenix Therapeutics, to discuss entrepreneurship, innovation, biotechnology, and how AI is being used to accelerate meaningful research in...

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...