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Stack And Startup Baltimore

Stack And Startup Baltimore

By: Jason Sherwood
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Summary

 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.2026 Economics Leadership Management & Leadership Marketing Marketing & Sales
Episodes
  • Al Fresco My IT guy

    Al Fresco My IT guy
    May 15 2026
    “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
    Show More Show Less
    13 mins
  • Why Right to Repair Matters for Every Business

    Why Right to Repair Matters for Every Business
    May 9 2026
    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
    Show More Show Less
    14 mins
  • Stack and Startup - Outdated equipment

    Stack and Startup - Outdated equipment
    May 1 2026
    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
    Show More Show Less
    12 mins
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