“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 strategy actually looks like

This is not about criticizing internal IT staff, freelancers, or trusted technicians.It is about understanding the difference between:
having support…
and having structure.

📊 Sources:

• Uptime Institute – IT outage and human error reporting
https://uptimeinstitute.com/
• CompTIA – IT workforce specialization trends
https://www.comptia.org/

📍 Series: Stack & Startup: Al FrescoThis channel focuses on business systems, operational thinking, technology strategy, and the real-world decisions behind sustainable growth.

🔔 Subscribe for weekly business and technology insight:
https://www.spreaker.com/podcast/stack-and-startup-baltimore--6877039

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

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 “right to repair” actually means
• Why businesses are more dependent on technology than ever
• The hidden costs of restricted repair access
• How downtime, cost, and flexibility are impacted
• Common misconceptions about repair access
• What businesses should consider when choosing systems📍 Series: Stack & Startup: Al FrescoThis channel focuses on real-world business insight and the systems behind growth, decision-making, and long-term performance.🔔 Subscribe for weekly insights and founder-focused content: https://www.youtube.com/@StackStartupBaltimore


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

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 impact on growth, efficiency, and risk
• How to identify outdated systems in your own business
• Practical steps to improve without overhauling everything

📊 Sources:
• McKinsey – Workplace productivity and inefficiency
https://www.mckinsey.com/
• CISA – Known exploited vulnerabilities
https://www.cisa.gov/

📍 Series: Stack & Startup: Al FrescoThis channel focuses on real-world business insight and the systems behind growth, decision-making, and long-term performance.
🔔 Subscribe for weekly insights and founder-focused content:
https://www.youtube.com/@StackStartupBaltimore

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

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, and building systems that can actually hold up under pressure.

In this episode:
• What failure looks like in materials science
• Why assumptions lead to bad diagnosis
• The cost of misreading a failure
• How testing systems create trust
• Why calibration matters
• Strange real-world lab stories
• What business owners can learn from scientific analysis
• Flexible materials, thermoelectrics, and future technology

Guest:
Priyanshu Banerjee LinkedIn: https://www.linkedin.com/in/p99/
Materials Scientist / Project Manager
Anderson Materials Evaluation

Learn more about Anderson Materials Evaluation:
https://www.andersonmaterials.com/
Mechanical testing services:
https://www.andersonmaterials.com/mechanical-testing/
Analytical testing services:
https://www.andersonmaterials.com/techniques/
Materials and chemical analysis:
https://www.andersonmaterials.com/analytical/

Subscribe for more conversations with business owners, builders, technologists, and experts shaping Baltimore, Maryland, and beyond.

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

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 your advantage.

💡 In this video:
• Why millennials are not a “young” generation anymore
• How economic instability shaped millennial founders
• The structural advantages of tech fluency
• Why millennial businesses show strong survival rates
• The role of purpose, diversity, and adaptability

📊 Sources & Data:
• Kauffman Foundation – Entrepreneurship data https://www.kauffman.org/
• U.S. Census / BLS – Workforce and generational data https://www.bls.gov/
• Federal Reserve – Household debt data https://www.federalreserve.gov/
• Flexera – IT and business efficiency data https://www.flexera.com/

📍 Series: Stack & Startup: Al Fresco This channel is focused on real business insight and the stories behind Baltimore and Maryland entrepreneurs.
🔔 Subscribe for weekly insights and founder conversations: https://www.youtube.com/@StackStartupBaltimore

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

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:
• Why IT problems often go unnoticed
• Mistake #1: Reactive IT environments
• Mistake #2: No clear IT strategy
• Mistake #3: Underinvesting in security
• How these issues impact growth and operations
• Practical steps to start fixing them
📊 Key Stats Mentioned:
• 20–30% revenue lost to inefficiencies (IDC)
• $5,600 per minute of downtime (Gartner)
• Up to 30% software waste (Flexera)
• 43% of cyberattacks target small businesses (Verizon)
• $4.45M average breach cost (IBM)

📍 Series: Stack & Startup: Al Fresco
Real business insight—one topic at a time.

This channel is dedicated to real-world business insight and the stories behind Baltimore and Maryland entrepreneurs.
🔔 Subscribe for weekly insights and founder stories: https://www.youtube.com/@StackStartupBaltimore

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

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, or questioning yourself—this is for you.

This channel is dedicated to real business insight and the stories behind Baltimore and Maryland entrepreneurs.

🔔 Subscribe for weekly insights and founder stories: [INSERT CHANNEL LINK]

💡 In this video:
• What imposter syndrome actually is
• Why it shows up when starting a business
• How self-doubt impacts decision making
• How to move forward despite uncertainty

📍 Series: Stack & Startup: Al Fresco Real business insight—one topic at a time.

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

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 Baltimore and Maryland businesses—highlighting the people, decisions, and moments that shape them.

🔔 Subscribe for more insights, founder stories, and weekly business breakdowns: https://www.youtube.com/@StackStartupBaltimore/videos

New episodes every Friday at 12:00 PM Eastern.

► Don't like commercials? Become a patron for ad-free content & more: www.patreon.com/stackandstartup
► Podcast versions of the show may be found at: https://www.spreaker.com/podcast/stack-and-startup-baltimore--6877039

Need help with your business technology? I work with Maryland businesses to improve security, reliability, and scalability of their IT systems.
👉 Book a free 15-minute assessment: https://calendly.com/jason-sherwood-sd-tech/15-minute-meeting

💡 In this video, we cover:

• Why downturns create opportunity
• The advantage of starting lean
• How competition shifts during uncertainty
• Long-term positioning vs short-term fear

📍 Series: Stack & Startup: Al Fresco A weekly series focused on real, practical insights for building and growing businesses—one topic at a time. 


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

🌿 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 marketing assets, this episode gives you a clear, practical framework to start using today.

🎯 What You’ll Learn:

• What the “Podcast Method” actually is
• How to use conversations to build business relationships
• Why podcasting is a powerful B2B growth tool
• Turning content into long-term marketing assets
• How to position yourself as a trusted authority in your space

🚀 Perfect For:

Entrepreneurs, MSP owners, consultants, and professionals looking to grow their brand, expand their network, and create consistent opportunities without relying on traditional outbound marketing.

🌿 About Stack & Startup Al Fresco
A solo series by Jason Sherwood focused on breaking down key business, technology, and growth concepts — filmed outside, unscripted in feel, but intentional in value.

👍 If this gave you a new perspective, make sure to like, comment, and subscribe for more episodes.

💬 Drop a comment: Would you start a podcast as part of your marketing strategy?

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

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 workflow, this video offers real-world guidance and actionable takeaways.

🌟 What You’ll Learn: 
• Key stages of project planning and execution
• Effective prioritization and task management
• Tools and techniques for managing risk and change
• Tips for leading teams and delivering results on time

🎯 Who Is This For?
Beginners, aspiring project managers, business leaders, and anyone interested in improving efficiency and outcomes in their work or personal projects!

👍 Like, Comment & Subscribe if you found this session valuable — and hit the bell 🔔 so you never miss future insights!
#ProjectManagement #Leadership #businessskillstraining 00:00 - Introduction to Project Management Challenges 01:15 - The Critical Role of Communication 03:38 - Experience vs. Certification in Project Management 06:03 - Coordination and Early Planning 09:41 - Challenges in Older and Historic Buildings 13:52 - Benefits of Raised Floor Systems 15:17 - Logistics and Supply Chain Management 18:42 - Technology, Automation, and Future-Proofing 24:36 - Aesthetics, Craftsmanship, and Modern Design 32:41 - Infrastructure for Technology: Cabling and Wireless 38:43 - Evolution of Building Technology and Automation 45:01 - Privacy and Ethics in Smart Technology 49:23 - The Character and History of Baltimore 57:01 - Maryland's Diverse Identity and History 01:06:03 - Restoration, History, and Moving Forward 01:12:52 - Closing Thoughts on Maryland's Potential

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