Stack And Startup Baltimore

Jason Sherwood
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  • Entrepreneurship
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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.

  1. Oct 17

    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 map can put millions of dollars at risk. In this episode of Stack & Startup Baltimore, Jason Sherwood sits down with Vivek Rao, Co-Founder and CTO of SiteSearcher AI, to talk about what happens when software and AI are applied to a process traditionally driven by research, local knowledge, and professional judgment. Vivek comes from a technology background rather than commercial real estate, which created an interesting founder challenge: how do you build software for experts when you are still learning the industry yourself? We get into: - Building software for an industry you didn't originally come from - Why technical founders need subject-matter experts - Learning enough of the domain to make good product decisions - The difficulty of finding commercial sites - Why maps and fragmented data consume so much time - How SiteSearcher approaches site-selection research - Where automation and AI can actually help - Why human judgment still matters - The importance of testing software against real expert workflows - Keeping people in the loop when automation becomes powerful - Building and operating an AI startup - What Vivek would automate next - The reality of becoming a founder after years as an engineer The interesting question isn't simply whether AI can produce an answer faster. It's: Can you trust how it got there? And even when the technology can surface a promising answer, there are still decisions where a professional needs to make the final call. Connect with Vivek Rao and SiteSearcher AI: SiteSearcher AI: https://www.sitesearcher.ai/ LinkedIn: https://www.linkedin.com/in/vivek-rao-7b075a1a/ Subscribe to Stack & Startup Baltimore for conversations with founders, operators, creators, and business leaders about what it actually takes to build something. Stack & Startup is a Baltimore-based business podcast focused on real conversations about building, running, and growing companies in Maryland. If you’re serious about improving how your business operates—from technology to decision-making—follow the show for practical, experience-driven insights. Watch and connect: YouTube: https://www.youtube.com/@StackStartupBaltimore LinkedIn: https://www.linkedin.com/in/jason-m-sherwood/ Need help with your business technology? 👉 Book a free 15-minute assessment: https://calendly.com/jason-sherwood-sd-tech/15-minute-meeting

  2. Oct 3

    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 a combination of all three. And where AI runs matters. In this episode of Stack & Startup: Al Fresco, I break down cloud AI, local AI, and why I believe the future for many businesses will ultimately be a hybrid of different systems doing different jobs. We look at: Why cloud AI is so powerful and accessible The privacy, control, cost, and vendor tradeoffs that come with it Where local and private AI can make sense Why more control also means more responsibility What I've learned while building my own local AI system Why hybrid AI may be the practical future How AI architecture becomes a governance decision What small businesses should actually be thinking about today This isn't an argument that every small business needs an AI server sitting in the office. In fact, most don't. It's about recognizing that different data, workloads, and risks may call for different tools. Businesses should be asking: What data is involved? What decision is being supported? What happens if the output is wrong? And where should that work actually happen? Because the future isn't cloud versus local. It's knowing what belongs where. This episode is part of the monthly Stack & Startup: Al Fresco AI Mini-Series, where we look at artificial intelligence through the lens of business operations, decision-making, and practical use. If you enjoy conversations about business, technology, AI, and growth, subscribe to Stack & Startup for more. Stack & Startup is a Baltimore-based business podcast focused on real conversations about building, running, and growing companies in Maryland. If you’re serious about improving how your business operates—from technology to decision-making—follow the show for practical, experience-driven insights. Watch and connect: YouTube: https://www.youtube.com/@StackStartupBaltimore LinkedIn: https://www.linkedin.com/in/jason-m-sherwood/ Need help with your business technology? 👉 Book a free 15-minute assessment: https://calendly.com/jason-sherwood-sd-tech/15-minute-meeting

  3. Sep 26

    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 Capital, to talk about what actually happens behind the numbers. Brooke brings more than two decades of experience across real estate brokerage, investing, ownership, and private lending. That means she has seen deals from multiple sides of the table — and has learned what separates an opportunity that looks good from one that can actually survive reality. We get into: • How private capital helps investors acquire and renovate properties • The role real estate investors can play in Baltimore neighborhood redevelopment • Why financial literacy matters • What television gets wrong about flipping houses • What separates serious borrowers from “tire kickers” • Why knowing your numbers matters more than getting excited about a property • The importance of liquidity, preparation and having a Plan B • The work and relationships behind successful real estate businesses • Technology and systems inside a private lending business • How education and preparation help investors manage risk One of Brooke's simplest lessons may also be one of the most important: If the numbers work, do the deal. If the numbers don't work, don't do the deal. And an ideal borrower isn't simply enthusiastic about a property. Brooke describes someone who has done the homework and has another plan if Plan A doesn't work. Connect with Brooke Gibson and Gibson Private Capital: Website: GibsonPrivateCapital.com Brooke also invites people to reach out with questions about real estate, private/hard-money lending and money. Subscribe to Stack & Startup for conversations with founders, operators, creators and business leaders about the realities of building something. Stack & Startup is a Baltimore-based business podcast focused on real conversations about building, running, and growing companies in Maryland. If you’re serious about improving how your business operates—from technology to decision-making—follow the show for practical, experience-driven insights. Watch and connect: YouTube: https://www.youtube.com/@StackStartupBaltimore LinkedIn: https://www.linkedin.com/in/jason-m-sherwood/ Need help with your business technology? 👉 Book a free 15-minute assessment: https://calendly.com/jason-sherwood-sd-tech/15-minute-meeting

  4. Sep 20

    “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 problem comes when nobody goes back. The spreadsheet created as a quick fix becomes business-critical. The shared login becomes standard procedure. The manual workaround becomes the official process. Eventually, nobody remembers why it was temporary in the first place. In this episode of Stack & Startup: Al Fresco, I look at how temporary solutions quietly become permanent systems — and why “good enough” can create hidden costs, dependencies, and operational debt over time. We cover: Why perfectly reasonable workarounds stick around How small operational friction compounds Why “it still works” isn't always a good enough reason to keep something How temporary systems create hidden dependencies The difference between flexibility and operational debt Why growing businesses eventually outgrow old solutions How to decide whether to keep, improve, document, or replace a workaround The goal isn't perfection or replacing everything overnight. It's making sure temporary solutions remain intentional decisions instead of permanent decisions made by accident. So ask yourself: What temporary solution in your business has been temporary for way too long? If you enjoy conversations about business, technology, operations, and growth, subscribe to Stack & Startup for more. Stack & Startup is a Baltimore-based business podcast focused on real conversations about building, running, and growing companies in Maryland. If you’re serious about improving how your business operates—from technology to decision-making—follow the show for practical, experience-driven insights. Watch and connect: YouTube: https://www.youtube.com/@StackStartupBaltimore LinkedIn: https://www.linkedin.com/in/jason-m-sherwood/ Need help with your business technology? 👉 Book a free 15-minute assessment: https://calendly.com/jason-sherwood-sd-tech/15-minute-meeting

  5. Sep 13

    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 dependencies. If the business can't function when one of them suddenly disappears, that isn't just an inconvenience. It's a business risk. In this Al Fresco, I talk about looking beyond whether something works today and asking a harder question: what happens when it doesn't? The goal isn't to eliminate every possible point of failure. That's probably impossible. It's to understand which failures could seriously disrupt the business and make reasonable plans before you're forced to improvise. Because "it's working fine" and "we're prepared for it to fail" are two very different things. Stack & Startup explores technology, entrepreneurship, business operations, and the lessons that come from actually building a business. Presented by SD Tech Maryland Strategic technology solutions for small and growing businesses. Stack & Startup is a Baltimore-based business podcast focused on real conversations about building, running, and growing companies in Maryland. If you’re serious about improving how your business operates—from technology to decision-making—follow the show for practical, experience-driven insights. Watch and connect: YouTube: https://www.youtube.com/@StackStartupBaltimore LinkedIn: https://www.linkedin.com/in/jason-m-sherwood/ Need help with your business technology? 👉 Book a free 15-minute assessment: https://calendly.com/jason-sherwood-sd-tech/15-minute-meeting

  6. Aug 23

    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 episode of Stack & Startup Al Fresco, I talk about subscription creep: the slow accumulation of software, SaaS platforms, licenses, accounts, and services that can quietly turn into operational complexity. The problem is bigger than wasted money. Every additional tool can introduce another account to manage, another place where company information lives, another integration, another renewal, and another piece of your technology environment that somebody needs to understand. That does not mean businesses should start canceling every subscription they can find. Cloud software and SaaS tools can create tremendous value. The goal is intentionality. Know what you are paying for. Know who owns it. Know who has access. Know what business value it creates. And know what risk it introduces. Useful tools should earn their place in your stack. If they do, great. If they do not, it might be time to clean up the stack. Stack & Startup Al Fresco explores business, technology, operations, and growth from the perspective of the decisions behind the technology — not just the technology itself. Subscribe for future conversations about building businesses and technology environments more intentionally. Stack & Startup is a Baltimore-based business podcast focused on real conversations about building, running, and growing companies in Maryland. If you’re serious about improving how your business operates—from technology to decision-making—follow the show for practical, experience-driven insights. Watch and connect: YouTube: https://www.youtube.com/@StackStartupBaltimore LinkedIn: https://www.linkedin.com/in/jason-m-sherwood/ Need help with your business technology? 👉 Book a free 15-minute assessment: https://calendly.com/jason-sherwood-sd-tech/15-minute-meeting

  7. Aug 7

    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, creating policies, making strategic decisions, or solving customer problems, AI can accelerate your work—but it cannot replace experience, ethics, accountability, or business judgment. The businesses that succeed with AI won't be the ones using it the most. They'll be the ones using it thoughtfully. AI is a powerful tool. It is not a substitute for thinking. Topics Covered • Why AI should amplify—not replace—your thinking • The danger of outsourcing judgment • Business ethics and responsible AI use • Why experience still matters • How leaders should approach AI adoption • Practical ways to use AI without becoming dependent on it If you enjoyed this discussion, consider subscribing for more conversations on technology, leadership, entrepreneurship, and practical business strategy. New Al Fresco episodes release every Friday. 🌐 SD Tech https://www.sdtechbaltimore.com Stack & Startup is a Baltimore-based business podcast focused on real conversations about building, running, and growing companies in Maryland. If you’re serious about improving how your business operates—from technology to decision-making—follow the show for practical, experience-driven insights. Watch and connect: YouTube: https://www.youtube.com/@StackStartupBaltimore LinkedIn: https://www.linkedin.com/in/jason-m-sherwood/ Need help with your business technology? 👉 Book a free 15-minute assessment: https://calendly.com/jason-sherwood-sd-tech/15-minute-meeting

  8. Aug 7

    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, Co-Founder & CEO of OncoVanta Therapeutics, to discuss what it really takes to build a biotech startup pursuing new treatments for pancreatic cancer and other solid tumors. Rather than focusing only on the science, this conversation explores leadership, entrepreneurship, learning outside your expertise, raising capital, building partnerships, and why some companies exist because the problem is simply too important to ignore. Topics include: • Starting a biotech company without coming from a medical research background • Building partnerships with Howard University and the NIH • Immuno-oncology explained for non-scientists • Why fundraising is a full-time job for biotech founders • The importance of mentorship and lifelong learning • Balancing family, entrepreneurship, and long-term vision • Leadership in highly technical industries • Why great businesses are really systems Whether you are a founder, entrepreneur, scientist, investor, or simply fascinated by how difficult companies are built, this episode offers valuable lessons that extend far beyond biotech. Guest: Roman Owens Co-Founder & CEO OncoVanta Therapeutics 🌐 Website: https://oncovanta.com 💼 LinkedIn: https://www.linkedin.com/in/roman-owens-447b762bb/ 📧 Email: rowens@oncovanta.com Stack & Startup explores the real stories behind building companies—from first ideas to growing organizations. We talk with founders, operators, creators, and business leaders about what actually goes into building something meaningful. 🎙 Available wherever you get your podcasts. Stack & Startup is a Baltimore-based business podcast focused on real conversations about building, running, and growing companies in Maryland. If you’re serious about improving how your business operates—from technology to decision-making—follow the show for practical, experience-driven insights. Watch and connect: YouTube: https://www.youtube.com/@StackStartupBaltimore LinkedIn: https://www.linkedin.com/in/jason-m-sherwood/ Need help with your business technology? 👉 Book a free 15-minute assessment: https://calendly.com/jason-sherwood-sd-tech/15-minute-meeting

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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.

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