The Cutover: Stories Of When The Switch Flipped copertina

The Cutover: Stories Of When The Switch Flipped

The Cutover: Stories Of When The Switch Flipped

Di: Lawrence Spector
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What happens when the system you knew stops working, and there’s no rollback?


The Cutover: Stories of When the Switch Flipped is a podcast about the defining moments that change the direction of our lives, careers, and businesses.


Hosted by Lawrence Spector, an engineering leader with 25 years of experience building and leading teams across industries including finance, defense, telecom, medical devices, gaming, cybersecurity, and AI, The Cutover takes an engineering concept and applies it to something much more personal.


In technology, a cutover is the moment a new system goes live. Months of preparation lead to one point of no return. Life has cutovers too, but unlike at work, there’s usually no rehearsal, rollback plan, or war room waiting when they happen.


Each week, Lawrence shares a story from his own journey or sits down with founders, engineers, leaders, and builders to examine one real moment when something changed. The decision they almost didn’t make. The diagnosis they didn’t expect. The failure that forced a new direction. The opportunity that opened one door while closing another.


These aren’t highlight reels. They’re stories about what someone believed before, what actually happened, what became clear afterward, and what they would do differently now.


Because sometimes the most important part of the story isn’t where you ended up.


It’s the moment the switch flipped.

© 2026 The Cutover: Stories Of When The Switch Flipped
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  • Experiences in Shipping AI without Compromising Security and Design | EP5
    Nov 3 2026

    What happens when an AI agent completes its task but quietly leaves your system exposed to security risks?

    In this episode, we explore firsthand experiences with shipping AI agents while protecting security and design principles. From an HTTPS deployment that left HTTP open to an agent reading a restricted secrets file, we learn how seemingly successful tasks can create serious risks. The episode also covers the challenges of managing multiple AI agents, unexpected network connections, and code changes that silently remove important features. Through real examples from personal projects, we discover why written rules aren't enough to keep AI systems secure. We also break down the difference between reducing risks and removing dangerous capabilities altogether, offering practical lessons on limiting agent access, protecting credentials, and building safer AI workflows without giving up speed.

    Episode highlights:
    (0:52) Introduction: Why AI agents need limited access and stronger security
    (1:19) The HTTPS deployment that exposed a hidden security risk
    (2:01) Understanding how AI agents operate with credentials and permissions
    (2:36) How AI agents create sub-agents beyond your direct control
    (3:20) The performance and security trade-offs of local vs. remote AI models
    (3:44) When successful AI deployments quietly create security problems
    (4:41) The secrets file incident: When an AI agent breaks its own rules
    (5:50) How an AI agent accidentally erased a feature during a merge
    (6:49) Hidden network dependencies discovered through failed deployments
    (7:37) Why successful AI tasks can be more dangerous than obvious failures
    (8:03) Two approaches to AI security: Removing capabilities vs. reducing risks
    (8:18) Protecting credentials, restricting network access, and limiting agent permissions
    (9:17) Why AI reviewers and automated checks aren't foolproof
    (10:06) The difference between reducing security risks and eliminating them
    (10:28) Why giving AI agents the least access possible matters
    (11:06) The first security step: Find out what your AI agents can actually access
    (11:23) Closing thoughts and a preview of next week's episode

    If you enjoyed this episode, follow the podcast, leave a review, and share it with someone who might find it helpful. Want to stay connected or learn more? Find me through the links and contact information below.

    Youtube: @LawrenceSpector, @the-cutover
    Facebook: https://www.facebook.com/lawrence.spector/, https://www.facebook.com/people/The-Cutover-with-Lawrence-Spector/61594426252229/
    Instagram: @lawrence.spector
    LinkedIn: https://www.linkedin.com/in/lawrencespector/
    Twitter/X: @SpectorLS
    Bluesky: @lawrencespector.bsky.social, @thecutover.bsky.social

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    12 min
  • The Wrong Mile High Club? The Story of My Highest Blood Sugar | EP4
    Oct 27 2026

    What would you do if your blood sugar shot past 330 while you were trapped on a plane at 30,000 feet?

    In this episode, I share the frightening flight home from Aruba that changed how I manage LADA diabetes. What started as a relaxing vacation turned into a struggle with rising blood sugar, constant glucose checks, and a dangerous insulin mistake. With limited knowledge of basal and bolus insulin, I made a decision out of panic that led to another problem hours later. I share how this experience pushed me to better understand my treatment, work closely with my healthcare team, and eventually switch to Dexcom and Omnipod. This isn't just a story about diabetes management. It's about learning from mistakes, staying calm under pressure, and understanding why having a plan is always better than guessing.

    Episode highlights:
    (0:00) Introduction: The Wrong Mile High Club
    (1:11) Blood sugar reaches 330 at 30,000 feet
    (1:41) Aruba vacation and early struggles with long-acting insulin
    (2:39) Rising glucose levels, panic, and symptoms during the flight
    (3:56) The insulin mistake that made things worse
    (4:41) The aftermath: A dangerous blood sugar low
    (4:54) Learning the difference between basal and bolus insulin
    (5:23) Switching to Dexcom and Omnipod for better diabetes management
    (5:50) Why understanding your treatment matters more than guessing
    (6:41) Lessons learned: What I'd tell my younger self
    (7:35) Final thoughts on staying prepared and managing diabetes with confidence

    If you enjoyed this episode, follow the podcast, leave a review, and share it with someone who might find it helpful. Want to stay connected or learn more? Find me through the links and contact information below.

    Youtube: @LawrenceSpector, @the-cutover
    Facebook: https://www.facebook.com/lawrence.spector/, https://www.facebook.com/people/The-Cutover-with-Lawrence-Spector/61594426252229/
    Instagram: @lawrence.spector
    LinkedIn: https://www.linkedin.com/in/lawrencespector/
    Twitter/X: @SpectorLS
    Bluesky: @lawrencespector.bsky.social, @thecutover.bsky.social

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    8 min
  • The Business I Quit | EP 3
    Oct 20 2026

    What if your business didn't fail because your idea was bad, but because no one knew it existed?

    In this episode of The Cutover, Lawrence shares how he spent seven months building a C++ learning website, only to attract three paying customers. He believed a great product would sell itself, but with no marketing plan, clear goals, or customer feedback, things didn't go as expected. Looking back, he questions whether he quit before giving his idea a real chance. Now, inspired by his wife and young daughter, he is ready to start again with a new approach. From learning when to quit to putting marketing first, he shares valuable lessons about entrepreneurship, overcoming fear, and choosing progress over perfection. If you've ever walked away from a dream too soon, this episode might change how you think about failure.

    Episode highlights:
    (0:00) The difference between quitting and failing
    (1:11) Building Compucator.com: Seven months of hard work
    (1:54) Why building a great product isn't enough
    (3:20) Three paying customers and the struggle to get noticed
    (3:53) The financial reality behind quitting the business
    (5:03) Lessons learned from a failed startup
    (5:45) How family and fatherhood inspired a fresh start
    (6:37) A new business strategy: Marketing first, perfection second
    (7:36) Setting clear goals and knowing when to quit
    (8:01) Applying startup lessons to leadership and work
    (8:22) The inspiration behind Lawrence’s second chance

    If you enjoyed this episode, follow the podcast, leave a review, and share it with someone who might find it helpful. Want to stay connected or learn more? Find me through the links and contact information below.

    Youtube: @LawrenceSpector, @the-cutover
    Facebook: https://www.facebook.com/lawrence.spector/, https://www.facebook.com/people/The-Cutover-with-Lawrence-Spector/61594426252229/
    Instagram: @lawrence.spector
    LinkedIn: https://www.linkedin.com/in/lawrencespector/
    Twitter/X: @SpectorLS
    Bluesky: @lawrencespector.bsky.social, @thecutover.bsky.social

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    9 min
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