Stack And Startup Baltimore

About Stack And Startup Baltimore

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.

Publisher

Jason Sherwood

Category

business · business · technology

Language

en

Explicit

No

First episode

10 Mar 2026

Latest episode

17 Oct 2026

Latest episodes

35 episodes in the feed.

1. 

   17 Oct 2026

   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 (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. 

   3 Oct 2026

   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 (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. 

   26 Sept 2026

   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 (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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Based on episode analysis; this does not confirm that the show is currently accepting guests.