PODCAST · business
Stack And Startup Baltimore
by Jason Sherwood
The Stack & Startup Podcast is a Baltimore-based business podcast focused on entrepreneurship, technology, and the realities of building companies in Maryland. Through interviews and direct commentary, the show features founders and business leaders who are actively shaping the regional economy. Stack & Startup delivers practical, experience-driven insights for business owners navigating growth, operations, and technology in today’s landscape.
Episodes
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Can You Trust AI With a Million-Dollar Decision? | Vivek Rao
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…
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Cloud AI vs. Local AI: Where Should Your Business Data Live?
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…
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What Real Estate Investing Actually Takes | Brooke Gibson
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…
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“It’s Just Temporary” — Until It Becomes Your Business Process
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…
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Your Business Is Only as Strong as Its Weakest Link
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...
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How $20 Software Subscriptions Become a Business Problem
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...
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AI Isn't a Crutch | Better Business Decisions Start With Better Judgment
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,...
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Building a Biotech Startup That Could Change Cancer Treatment | Roman Owens
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,...
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Has Your Business Outgrown Its IT? Signs You're Creating More Friction Than Growth
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…
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The Future of Healthcare Starts With Access | Charlie Nahabedian
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…
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The Most Dangerous Phrase in Business: "It's Working Fine"
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....
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Innovation Needs People, Not Just AI | Dowdy Jackson, PhD
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...
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Al Fresco Prepare your business for growth
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...
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How AI Is Changing Healthcare—Without Replacing Doctors | Dr. Mikel Daniels
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,...
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AI Is Already in Your Business. Are You Governing It?
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...
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Why Great Ideas Fail Without Execution | Phil Parsons
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...
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Could Your Business Survive Losing Everything?
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…
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Why Relationships Still Matter in Business | Andy Kobus
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...
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How to Know If Your Business Is One Cyberattack Away From Shutdown
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...
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Stack and Startup interview Crystal Baze Barney CPA
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,...
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If Your Backups Aren't Tested, They Don't Exist
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…
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Most Legal Problems Start as Business Problems | Shavon Smith
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…
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Cloud vs Local Servers: What Actually Makes Sense in 2026
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…
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What an MSP Actually Does (And Why Businesses Wait Too 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...
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Most Businesses Build the Wrong IT Systems
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...
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Al Fresco My IT guy
“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…
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Why Right to Repair Matters for Every Business
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...
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Stack and Startup - Outdated equipment
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…
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Why Things Fail: A Materials Scientist Explains - Priyanshu Bannerjee
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...
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Stack and Startup Al Fresco Millennial Advantage
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…
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Stack and Startup Al Fresco 3 IT mistakes
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...
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Stack and Startup Al Fresco Imposter syndrome
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...
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Why Starting a Business in a Recession Is Actually Smarter
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...
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Stack and Startup Al Fresco | The Podcast Method for Marketing
🌿 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...
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Stack and Startup s01e01 - Kathleen Sherrill
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…
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ABOUT THIS SHOW
The Stack & Startup Podcast is a Baltimore-based business podcast focused on entrepreneurship, technology, and the realities of building companies in Maryland. Through interviews and direct commentary, the show features founders and business leaders who are actively shaping the regional economy. Stack & Startup delivers practical, experience-driven insights for business owners navigating growth, operations, and technology in today’s landscape.
HOSTED BY
Jason Sherwood
CATEGORIES
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Frequently Asked Questions
How many episodes does Stack And Startup Baltimore have?
Stack And Startup Baltimore currently has 35 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Stack And Startup Baltimore about?
The Stack & Startup Podcast is a Baltimore-based business podcast focused on entrepreneurship, technology, and the realities of building companies in Maryland. Through interviews and direct commentary, the show features founders and business leaders who are actively shaping the regional economy....
How often does Stack And Startup Baltimore release new episodes?
Stack And Startup Baltimore has 35 episodes. Check the episode list to see recent publication dates and frequency.
Where can I listen to Stack And Startup Baltimore?
You can listen to Stack And Startup Baltimore on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Stack And Startup Baltimore?
Stack And Startup Baltimore is created and hosted by Jason Sherwood.
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