エピソード

  • Could Your Business Survive Losing Everything?

    Could Your Business Survive Losing Everything?
    2026/06/26
    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 steps every business owner should understand
    Data loss is not just an IT problem.
    It is a business continuity problem.
    If your business depends on data—and every business does—this episode is for you.

    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
    続きを読む 一部表示
    12 分
  • Why Relationships Still Matter in Business | Andy Kobus

    Why Relationships Still Matter in Business | Andy Kobus
    2026/06/23
    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, emotional intelligence, mental health awareness, community involvement, authenticity, and the long-term value of showing up consistently for people.
    If you are a business owner, entrepreneur, sales professional, or community leader, this conversation offers practical insight into building trust that lasts.
    Topics discussed:
    • Why relationships still outperform automation
    • The difference between networking and trust-building
    • How reputation compounds over time
    • Emotional intelligence in leadership
    • Collaboration versus competition
    • Building stronger business communities
    • Mental health and leadership
    • Authenticity with accountability
    • Why trust remains a competitive advantage
    Connect with Andy Kobus:
    LinkedIn: https://www.linkedin.com
    Subscribe for more conversations with Baltimore business leaders, founders, creators, and entrepreneurs.
    Support the show:
    https://patreon.com/stackandstartup

    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
    続きを読む 一部表示
    1 時間 13 分
  • How to Know If Your Business Is One Cyberattack Away From Shutdown

    How to Know If Your Business Is One Cyberattack Away From Shutdown
    2026/06/19
    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 overlook
    • How to evaluate your cyber resilience
    Cybersecurity is not about eliminating risk.
    It is about reducing exposure and improving recovery when something eventually goes wrong.

    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
    続きを読む 一部表示
    11 分
  • Stack and Startup interview Crystal Baze Barney CPA

    Stack and Startup interview Crystal Baze Barney CPA
    2026/06/16
    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 business operations
    • Why millennials may be uniquely positioned between analog and digital business worlds
    • The biggest mistakes growing businesses make
    Whether you are a founder, entrepreneur, operator, or small business owner, this conversation offers practical insights into building a business that can grow without creating chaos.
    Connect with Crystal Baze Barney:
    Website: https://www.jbamd.com
    Journey Business Accounting
    Stack & Startup Baltimore explores the realities of building businesses, careers, technology, and ideas throughout Baltimore and Maryland.
    Subscribe for conversations with founders, operators, creators, and business leaders.

    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
    続きを読む 一部表示
    1 時間 3 分
  • If Your Backups Aren't Tested, They Don't Exist

    If Your Backups Aren't Tested, They Don't Exist
    2026/06/12
    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 businesses realize
    • Practical steps every organization should take to validate backup systems
    The goal is not simply having backups.
    The goal is knowing they will work when you need them.
    ---
    📊 Sources:
    Veeam Data Protection Report
    https://www.veeam.com
    Datto Global State of the Channel Ransomware Report
    https://www.datto.com
    National Archives & Records Administration (NARA)
    https://www.archives.gov
    ITIC / Statista Downtime Research
    https://www.statista.com
    ---
    Stack & Startup: Al Fresco explores business growth, technology strategy, leadership, and the systems that help organizations scale effectively.
    Subscribe for weekly conversations around business, technology, and growth.

    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
    続きを読む 一部表示
    12 分
  • Most Legal Problems Start as Business Problems | Shavon Smith

    Most Legal Problems Start as Business Problems | Shavon Smith
    2026/06/09
    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, technology, and legal workflows
    • Building a stronger business foundation before problems appear
    Whether you are a founder, entrepreneur, consultant, or small business owner, this conversation offers practical insights into protecting your business before expensive problems arise.
    Connect with Shavon Smith:
    Website:
    https://www.thesjslawfirm.com/
    LinkedIn:
    https://www.linkedin.com/in/shavon-j-smith-1115051/
    Stack & Startup Baltimore explores the people, businesses, technology, and ideas shaping Baltimore and Maryland's business community.

    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
    続きを読む 一部表示
    39 分
  • Cloud vs Local Servers: What Actually Makes Sense in 2026

    Cloud vs Local Servers: What Actually Makes Sense in 2026
    2026/06/05
    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 business?"
    We discuss:
    • Cloud computing advantages and disadvantages
    • Local server advantages and disadvantages
    • Hybrid infrastructure models
    • Security considerations
    • Scalability and cost concerns
    • Performance requirements
    • Business continuity planning
    • How to choose the right infrastructure strategy
    The smartest technology decisions are not based on trends.
    They are based on alignment.
    📍 Stack & Startup: Al Fresco
    Weekly conversations about business growth, leadership, technology, and operational strategy.
    🔔 Subscribe for more business and technology insights.

    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
    続きを読む 一部表示
    14 分
  • What an MSP Actually Does (And Why Businesses Wait Too Long)

    What an MSP Actually Does (And Why Businesses Wait Too Long)
    2026/05/29
    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 smarter technology decisions without overspending
    The goal is not the cheapest system.
    And it is not the most advanced system.
    It is the system that actually fits your business.
    ---
    📊 **Sources:**
    • IDC – Business inefficiency research
    https://www.idc.com/
    • McKinsey – Workplace inefficiency studies
    https://www.mckinsey.com/
    • Verizon DBIR – Cybersecurity and breach reporting
    https://www.verizon.com/business/resources/reports/dbir/
    • CompTIA – IT workforce and support trends
    https://www.comptia.org/
    ---
    📍 **Series: Stack & Startup: Al Fresco**
    This channel focuses on business systems, operational thinking, leadership, and technology strategy for growing businesses.
    🔔 Subscribe for weekly insights around business, systems, and growth:
    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
    続きを読む 一部表示
    14 分