Nobody holds a meeting and decides to become AI reliant. It happens quietly, over a few months, until the work does not get done at the old speed without it. This episode is about that line: what "AI first" actually means, what happens if the price of crossing it changes, and why the thing that decides your bill is probably not the pricing page.

In this episode, you'll learn:

• What "AI first" means, and why nobody on our team would say it, or recommend it
• The question that separates reliance from real risk
• Lisa's case that prices go up, and Jeff's case that they go down
• When a local model on your own hardware starts to pay for itself
• What clients are actually asking for, which is not what the internet says

Links:

Book a chat: tideslot.com/team/tech-log/tech-log-chat
Port & Starboard: portstbd.com

Sponsor:

This episode is brought to you by Fathom Coffee. fathomcoffee.com. 

On this episode, Jeff & Lisa were drinking out 10,000 Roast - Costa Rica Tarrazú San Diego Jaguar Honey and Alexandra was drinking our classic BCB Espresso w/ a homemade blueberry & honey syrup cortado.

Most small businesses are using AI. Almost none of them have written down what that means. The Small Business House Committee put numbers on it this month: 58% of small businesses use generative AI, closer to 70% if you work anywhere near technology, and nearly none of them have anything on paper. This episode is about what actually belongs on that page, and what to do in the months before the page exists.

• Why no policy is an operational gap, not a paperwork gap
• Lisa's five rules, including the one that has nothing to do with data
• What to put in place while your policy sits in legal review
• Why a one page policy on the wall does not change behavior
• How to build a team that tells you when something went wrong

Links & Resources Mentioned:

Book a chat: tideslot.com/team/tech-log/tech-log-chat

Port & Starboard: portstbd.com

Download our AI Policy One Pager here!

Fueled By Coffee

We don't just talk tech; we roast, brew, and drink coffee 24/7. This episode was fueled by Fathom Coffee. Get your fix at fathomcoffee.com.

The Tech Log | Are Companies Leaving Salesforce?

Build v. Buy. Are businesses finally pushing back against the high cost of their enterprise CRMs? This episode dives into the growing pressure in the CRM space, how companies often underutilize their expensive platforms, and the emerging role of AI-accelerated development in creating custom solutions. We explore critical considerations like compliance, security, and long-term maintenance when choosing the right CRM strategy for your unique business needs.

• Many businesses are grappling with the high costs of enterprise CRMs like Salesforce and HubSpot, questioning if they truly leverage the full extent of their paid features.
• The rise of AI-accelerated development is making custom CRM solutions more accessible, but experts warn about security risks and the need for robust planning beyond simple prototypes.
• Making the right CRM choice involves a deep dive into your specific business processes, future growth projections, compliance requirements, and the long-term costs of both licensing and maintenance.

Links & Resources Mentioned

Book a Chat: https://tideslot.com/team/tech-log/tech-log-chat

Learn more about Port & Starboard: https://portstbd.com/

Fueled by Coffee

We don't just talk tech; we roast, brew, and drink coffee 24/7. This episode was fueled by Fathom Coffee. Get your fix at: fathomcoffee.com

Follow Tech Log: Subscribe to stay ahead of the curve as we navigate the rapidly evolving landscape of AI, data, and business technology.

The Tech Log | Agent or Code - what is the right solution?

Is the allure of AI agents leading us into a costly trap, or are we simply discovering a powerful new tool for unpredictable challenges?

The recent surge in AI agent adoption sparks a debate: when should you choose an agent over traditional code? While AI offers speed and accessibility, we explore the "agent trap" where predictable tasks are over-engineered with expensive, token-wasting AI loops. Lisa discusses the benefits of agents for handling exceptions and experimental workflows, contrasting this with code's reliability for deterministic, repetitive processes. The conversation also touches on the cost of maintenance, the need for business context, and the critical role of human ingenuity in a technology-first world.

• AI agents excel at handling exceptions, ambiguous situations, and experimental workflows where predictability isn't guaranteed.
• Traditional code remains the most efficient and cost-effective solution for deterministic, repetitive tasks and predictable outcomes.
• Business owners should prioritize identifying specific problems to solve and choose the "right tool for the job" rather than blindly adopting the latest AI trends.

Links & Resources Mentioned

• Book a Chat: https://tideslot.com/team/tech-log/tech-log-chat
• Learn more about Port & Starboard: https://portstbd.com/
• Follow Rollins.io

Fueled by Coffee

We don't just talk tech; we roast, brew, and drink coffee 24/7. This episode was fueled by Fathom Coffee. Get your fix at: fathomcoffee.com

Follow Tech Log: Subscribe to stay ahead of the curve as we navigate the rapidly evolving landscape of AI, data, and business technology.

From university commencement stages to dinner party conversations, AI is sparking a spectrum of reactions, from awe to outright fear.

AI is everywhere, but is everyone on board? This episode dives into the mixed public reactions to artificial intelligence, from outright boos at commencement speeches to the quiet anxieties of professionals outside the tech bubble. We explore how AI is being 'forced upon' workers without clear direction, prompting frustration and fear. Is this disruption comparable to the internet, or is AI fundamentally different, targeting 'brain work' and changing at an unprecedented pace? The team grapples with creative grief, the nuances of AI optimism, and whether it's possible to be enthusiastic about AI while acknowledging what's being lost.

*   Many outside the tech world harbor fear, frustration, or indifference towards AI, especially when its adoption is mandated without clear direction.
*   Unlike past technological shifts, AI is targeting "brain work" and is advancing at an unprecedented pace, making comparisons to the internet or Industrial Revolution feel incomplete.
*   While some creatives express grief over the perceived devaluation of their craft by AI, others are finding innovative ways to leverage it as an empowering tool.

Links & Resources Mentioned

Book a Chat: https://tideslot.com/team/tech-log/tech-log-chat

Learn more about Port & Starboard: https://portstbd.com/

Fueled by Coffee

We don't just talk tech; we roast, brew, and drink coffee 24/7. This episode was fueled by Fathom Coffee. Get your fix at: fathomcoffee.com

Follow Tech Log: Subscribe to stay ahead of the curve as we navigate the rapidly evolving landscape of AI, data, and business technology.

This week Lisa and Alexandra discuss the intersection of personal taste and the future of technology.

There is a common conversation happening in many circles now, a conversation about taste's critical role in technology. We explore how personal preference, critical judgment, and instinct drive innovation, especially in an AI-dominated world. Is AI refining our taste or diluting it? We delve into the importance of human discernment, the elegance of well-designed tech solutions, and whether we're losing our willingness to aggressively break rules in design.

• How is taste defined beyond dictionaries, specifically in the context of technology solutions and AI development?
• The tension between a designer's "gut feeling" and AI's data-driven, regenerative processes in creating truly innovative products.
• Does AI's output leads to a dilution of unique design or if humans retain the responsibility to foster discernment and originality in technology.

Links & Resources Mentioned

Book a Chat: https://tideslot.com/team/tech-log/tech-log-chat

Learn more about Port & Starboard: https://portstbd.com/

Fueled by Coffee

We don't just talk tech; we roast, brew, and drink coffee 24/7. This episode was fueled by Fathom Coffee. Get your fix at: fathomcoffee.com

Follow Tech Log

Subscribe to stay ahead of the curve as we navigate the rapidly evolving landscape of AI, data, and business technology.

Spoiler alert: Statistically, your next tech project has a 70% chance of running aground—but before you go blaming the software, let's look at the humans steering the ship.

In Episode #6, Alexandra sits down with Brittany Browning and Lisa DeNoia to discuss why technology implementations routinely disintegrate halfway through the timeline. They look past the software glitches to expose the real culprits: communication breakdowns, rushed requirements, and the fatigue of the "messy middle." Tune in to find out how to salvage a drifting project before it completely drains your budget and your sanity.

• The Requirements Trap: Why rushing through the sign-off phase just to "get it built" ensures your data metrics will be completely useless months down the road.
• The Stealth Value of Shadowing: Why watching an end-user click 20 times to complete a basic task reveals the operational pain points that corporate leadership completely misses.
• Stripping It Back to Basics: How using simple, black-and-white wireframes forces teams to bridge the massive gap between what they said and what they actually meant.
• The 4-Slide Rescue Deck: A logical, no-nonsense framework to confidently raise the red flag to stakeholders when a project timeline begins to warp.

• Book a Chat: https://tideslot.com/team/tech-log/tech-log-chat
• Learn more about Port & Starboard: https://portstbd.com/

We don't just talk tech; we roast, brew, and drink coffee 24/7. This episode was fueled by Fathom Coffee. Get your fix at: fathomcoffee.com

Follow Tech Log: Subscribe to stay ahead of the curve as we navigate the rapidly evolving landscape of AI, data, and business technology.

If you think spinning up a prototype in fifteen minutes flat means smooth sailing ahead, you might want to check for structural leaks before your entire data model sinks into the ocean.

In this episode, Alexandra sits down with Lisa DeNoia and Jeffrey Werby to navigate the turbulent waters between instant AI experimentation and foundational planning. They dive into why the traditional whiteboard design process is being declared "dead" by industry insiders, how to avoid the siren song of polished but ultimately useless prototypes, and the exact moment you need to drop the keyboard and pull out a pen and paper.

• The Intoxication of the 15-Minute Prototype: Why skipping wireframes and PRDs feels like a superpower but might actually be the most expensive shortcut your business takes this year.
• The Curse of Reactive Cognition: How seeing a beautifully rendered AI mockup too early forces your brain to settle for what's in front of you instead of what you actually meant to build.
• Grok, Obsidian, and Leaked Pickleballs: A look into the hosts' personal workflows, including a cautionary tale of how an LLM allegedly handed a million-dollar cucumber idea straight over to Vlasic.
• The Restaurant Analogy for Software Development: Why eating at a hundred restaurants doesn't make you a Michelin-star chef, and why using Instagram doesn't mean you're ready to architect an enterprise CRM.
• Steering Without a Chart: Why you don't always have to wait for a perfect plan in a rapidly shifting AI landscape—and how to develop your own personal style through disciplined play.

• Book a Chat with us.
• Learn more about Port & Starboard
• Industry Reference: Jenny Wen (Head of Design at Claude) on the evolution of the modern design process.

Fueled by Coffee We don't just talk tech; we roast, brew, and drink coffee 24/7. This episode was fueled by Fathom Coffee. Get your fix at: fathomcoffee.com

Follow Tech Log: Subscribe to stay ahead of the curve as we navigate the rapidly evolving landscape of AI, data, and business technology.

The Tech Log | Episode 4: Security in the Age of Vibe Coding

The tools building our products are the same tools being used to attack them. Not glamorous — but necessary.

In episode four, Alexandra Craig sits down with Jeff Werby and Lisa DeNoia of Port & Starboard to break down two recent high-profile security incidents and what they mean for anyone building with AI right now.

In This Episode, You'll Learn:

• What Happened at GitHub & Lovable: A poisoned VS Code extension, 3,800 breached repositories, and $6.6B platform with a very bad couple of months — here's the breakdown.
• Same Problem, Bigger Scale: Why the security threats of today aren't new — they're just faster, wider, and harder to recover from.
• The Abandoned App Problem: Thousands of vibe-coded apps sitting on the internet with corporate data, hospital PII, and stealth startup strategies just... publicly accessible.
• YOLO Is Not a Security Strategy: What happens when well-meaning employees click "allow" on everything without understanding what they're actually granting.
• The Third Wave: Lisa's take on where we are in software development history — and why, like ska music and craft coffee, there's no putting this one back.

Links & Resources Mentioned:

• Book a Chat: Schedule a time with the Tech Log team.
• The Agency: Learn more about Port & Starboard.

Fueled by Caffeine ☕ We don't just talk tech; we roast, brew, and drink coffee 24/7. This episode was fueled by Fathom Coffee. Get your fix at: fathomcoffee.com

Follow Tech Log: Subscribe to stay ahead of the curve as we navigate the rapidly evolving landscape of AI, data, and business technology.

The Tech Log | Episode 3: Vibe Coding Beyond the Vibe

"When everyone can build without effort, the value of building also decreases." Is that true? Alexandra, Jeff, and Lisa dig in.

In episode three, Alexandra Craig sits back down with Jeff Werby and Lisa DeNoia of Port & Starboard to challenge the hype around vibe coding — and make the case for something more intentional: AI accelerated development.

In This Episode, You'll Learn:

• Vibe Coding vs. AI Accelerated Development: Why the distinction matters — and why one of them still requires a serious brain behind the keyboard.
• The Stack: The real tools, frameworks, and practices Jeff is using to build production-ready applications (hint: it's not Lovable).
• The Generism Trap: What Michael Malewicz's viral article gets right about a world full of flat, soulless products — and what the IKEA furniture hackers teach us about craft.
• Bridging the Gap: Practical advice for the founder who's 85% done with a vibe-coded prototype and staring at the finish line.

Links & Resources Mentioned:

• Read the Article: Vibe Coding Is Over by Michal Malewicz.
• Book a Chat: Schedule a time with the Tech Log team.
• The Agency: Learn more about Port & Starboard.

Fueled by Caffeine ☕ We don't just talk tech; we roast, brew, and drink coffee 24/7. This episode was fueled by Fathom Coffee. 👉 Get your fix at: fathomcoffee.com

Follow Tech Log: Subscribe to stay ahead of the curve as we navigate the rapidly evolving landscape of AI, data, and business technology.