
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...


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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Contact path
Verified email
Booking probability
40%
Guest openness
Selective
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Signup to Generate a PitchThe 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.
Recent episodes include "Can You Trust AI With a Million-Dollar Decision? | Vivek Rao" (17 October 2026, 54 minutes), "Cloud AI vs. Local AI: Where Should Your Business Data Live?" (3 October 2026, 18 minutes), and "What Real Estate Investing Actually Takes | Brooke Gibson" (26 September 2026, 74 minutes).
Stack And Startup Baltimore publishes roughly weekly, with episodes averaging 41 minutes across 35 episodes.
Booking probability for Stack And Startup Baltimore is 40%, and the host is rated Selective on guests. Stack And Startup Baltimore requires a Pod Score of 80 or higher. Stack And Startup Baltimore's contact route on record: verified email.
The strongest fits for Stack And Startup Baltimore are Business & Management Consulting. Stack And Startup Baltimore has a business audience.
Stack And Startup Baltimore is a business podcast with 35 episodes published.
Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

Episode #16
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...

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...

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...

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...

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...

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 &...

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...

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...

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...
Recent guests on Stack And Startup Baltimore. Study who booked and why before you pitch.
Phase 23
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