Stack And Startup Baltimore

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 tempor...

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 i...

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, an...

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.

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...

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 quietly builds over time, why business growth exposes weaknesses in technology and processes, and how recognizing those warning signs early can save countless hours of frustration later.
Growth shouldn't make your business harder to run.
It...

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 vision
• Why persistence matters more than quick wins
• Expanding healthcare access through technology
• Lessons learned from decades of entrepreneurship
• How innovation can improve patient outcomes without losing the human element

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 "just knows how everything works," these hidden dependencies can become expensive overnight.
This episode isn't really about IT.
It's about operations.
It's about leadership.
And it's about asking a simple question before...

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 instead of simply automating routine work.
Rather than replacing people, AI has the potential to help researchers move faster, discover more, and focus on solving some of healthcare's biggest challenges.
In this conversation we discuss:
• Entrepreneurship and bu...

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, cloud services, automation, or operational processes, growth shouldn't mean constant friction. Technology should remove obstacles—not create them.
In this episode:
• Why growing businesses eventually outgrow their original technology
• Common bottlenecks that hold companies back
• Planning infrastructu...

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:
• How AI is changing medical documentation
• Why healthcare technology still needs human review
• The risks and limits of AI in patient communication
• Cybersecurity and HIPAA in real-world medical practices
• Why trust...

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.
In the first episode of a new monthly AI series, Jason Sherwood explores practical AI governance for small and midsize businesses, including acceptable use, data boundaries, verification, accountability, and why banning AI...

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-driven workflows, Phil shares lessons learned from building projects, teams, and businesses through repeatable systems rather than relying on motivation alone.
Topics include:
• Why great ideas often fail
• Execution versus inspiration
• Project management and accoun...

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
• The critical first 24 hours after data loss
• Operational and financial consequences
• Why backups fail when they are never tested
• Recovery planning and business resilience
• Cyber insurance and risk mitigation
• Practical...

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 outperform automation in business.
Andy serves on multiple nonprofit boards throughout the Baltimore region and has built a reputation as one of the area's most respected business connectors. Together we explore networking, leadership...

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 more vulnerable than you realize.
Topics include:
• Tested backups and disaster recovery
• Multi-factor authentication (MFA)
• Patch management and system updates
• Incident response planning
• Visibility into your environment
• The hidden risks many businesses o...

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 about:
• Why many business owners are flying blind
• The relationship between systems and sustainable growth
• Why more revenue can create more stress
• The difference between accounting and finance
• Technology, AI, automation, and modern bus...

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 backups fail
• What happens when recovery is needed and systems cannot be restored
• Ransomware recovery challenges
• Downtime costs and operational disruption
• Why testing matters more than most busines...

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 founders wait too long to involve legal counsel
• Partnership agreements and business risk
• Contracts, documentation, and dispute prevention
• Operational systems that reduce legal exposure
• Scaling a business without creating unnecessary risk
• AI, technolo...

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 hybrid environments so business owners can make smarter technology decisions.
Because the question is not:
"Cloud or Local?"
The real question is:
"What best aligns with the needs of...

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-term impact
We talk about:
• why cheap systems become expensive over time
• the hidden cost of operational friction
• overengineered environments
• reactive vs intentional decision-making
• cybersecurity risks
• and how busin...

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-term impact 

We talk about: 
• why cheap systems become expensive over time 
• the hidden cost of operational friction 
• overengineered environments 
• reactive vs intentional decision-making 
• cybersecurity risks 
• and how businesses can make smarte...

“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 problem is usually not the person.
It is the lack of systems around them.

We talk about:

• single points of failure
• reactive vs proactive IT
• documentation gaps
• burnout
• operational risk
• scalability
• and what a real IT s...

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 Fresco, we break down what right to repair actually means—and why it has real consequences for business operations, downtime, and long-term flexibility.Because when something fails…
you are either in control of the solution—
or you are waiting on someone else.💡 In this video:
• What...

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 performance across your business.

Because the biggest risk is not failure.

It is friction.

💡 In this video:
• What “outdated systems” actually mean
• The hidden costs most businesses do not measure
• Why companies keep systems that no longer serve them
• The long-term imp...

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 Evaluation in Columbia, Maryland.

We talk about failure analysis, material testing, bad assumptions, calibration, diagnostic systems, and what businesses can learn from the way scientists investigate why things break.

This conversation goes beyond materials. It is about decision-making, testing assumptions...

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 founders have in today’s business environment—from adaptability and tech fluency to survival rates and business structure.

If you are building a business right now, this is about understanding the environment you are actually operating in—and how to use it to you...

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 break down three common IT mistakes that cost businesses money—and what you can do to fix them.

If you are running a business or planning to scale, understanding these issues early can save you time, money, and unnecessary stress.

💡 In this video:
•...

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 this episode of Stack & Startup: Al Fresco, we break down what imposter syndrome really is, why it shows up when you are starting something new, and how to move forward even when you feel uncertain.

If you are starting a business, thinking about it, o...

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 long-term success, and what most people get wrong when they wait for “the perfect time.”

If you are thinking about starting a business, questioning your next move, or trying to navigate uncertainty—this is for you.

This channel is dedicated to telling the real stories behind Baltim...

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 long-term success, and what most people get wrong when they wait for “the perfect time.”

If you are thinking about starting a business, questioning your next move, or trying to navigate uncertainty—this is for you.

This channel is dedicated to telling the real stories behind Baltim...

🌿 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 strategic approach to building authority, creating meaningful relationships, and generating real business opportunities through podcasting.

This isn’t about going viral. It’s about building a network, brand, and pipeline the right way.

If you’ve ever wondered how a podcast can become one of your most valuable...

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 Kathleen Sherrill — perfect for students, professionals, and anyone looking to sharpen their planning, execution, and leadership skills! From defining clear goals to managing risks and building high-performing teams, Kathleen breaks down the core frameworks and best practices you need to succeed in any project environment. Whether you’re new to project management or seeking strategies to elevate your wo...