Avoiding ai failures by using AI First Principles

Most teams are rushing to bolt AI onto existing workflows, but that often just scales the dysfunction faster. In this episode of WP Product Talk, we explore AI first principles with Anthony Franco, Executive Director and Founder of FirstStrategy.ai, and why operationalizing AI starts with rethinking the systems behind your business. Join hosts Matt Cromwell and Zack Katz on March 11, 2026 at Noon Eastern as they unpack practical ways WordPress product owners can rethink processes, eliminate bureaucracy, and design smarter operations before layering in AI. https://www.aifirstprinciples.org https://www.wisermethod.com/books

For years, SEO was the default marketing playbook for WordPress plugin and product businesses. Build content, rank on Google, get traffic. It worked - until it didn't. AI is changing how people search for information, and organic traffic that took years to build is starting to erode. If your marketing strategy is mostly built on SEO, that's a real problem. And doing more of the same isn't the answer. So what do you do instead? Ben Pines - who was the first marketer at Elementor and helped build it into one of the most recognized brands in WordPress - has been working on exactly this question. His answer: founder-led marketing. The kind of brand-building that's rooted in your own story, perspective, and expertise. The kind AI can't replicate. In this episode, hosts Katie Keith and Ian Misner chat with Ben about what it actually means to shift from SEO-driven marketing to a founder-led approach - and what that looks like for real WordPress product businesses with small teams and limited time. They'll dive into: Why SEO is getting harder and what's actually driving the decline What founder-led marketing is and worth pursuing in an AI world How to show up consistently without it taking over your life Where to start if you've never built a personal brand before

In this episode of WP Product Talk, Ben Sibley, co-founder of Independent Analytics, joins Matt and Ian for an honest, tactical conversation about what it really takes to run and grow a profitable WordPress product business with just two people. Ben shares why he intentionally rejected the “grow at all costs” startup mindset and instead built a lean, lifestyle-oriented company focused on creative fulfillment, sustainable growth, and strong margins. Rather than chasing headcount as a marker of success, he and his co-founder have designed their business around constraints—time constraints, cost constraints, and deliberate tradeoffs. The result? Four years without hiring, full-time product development, and a system that scales without turning into a support-heavy “debt machine.” You’ll hear how they: Divide responsibilities so product development stays the top priority Use customer feedback boards and real-world support data to prioritize features Treat support as a growth lever, not just a cost center Scale support with documentation, AI, FAQs, and proactive product improvements Optimize their WordPress.org plugin page to drive sustainable organic growth Convert free users to paid customers through in-product upgrades and conversion optimization Approach marketing with restraint—investing in brand building, YouTube partnerships, and coaching instead of spraying money at ads Ben also pulls back the curtain on growth realities in 2026: the decline of traditional SEO, AI-driven search changes, the stability (and strategy) of the WordPress.org repository, and why brand building and reputation now matter more than ever. Instead of chasing every new channel, he focuses on strengthening core assets—product experience, checkout flow, onboarding, and long-term trust. The conversation dives deep into practical founder tensions too: When do you hire versus staying scrappy? How do you avoid building a bloated organization that moves slower over time? What’s the risk of keeping all institutional knowledge in two founders’ heads? How do you balance growth marketing with product improvements? If you’re a WordPress product creator trying to bootstrap your WordPress business, build a lean startup, or simply avoid turning your SaaS into a high-burn support machine, this episode is packed with grounded, experience-backed insights you can apply immediately. Whether you’re at 10 downloads a day or 100,000 active installs, this conversation will challenge how you define success—and help you build a business that works for your life, not the other way around.

AI is everywhere right now, but most conversations stop at content, marketing, or features. This episode goes behind the scenes. Michael Eisenwasser, Co-Founder of Rapyd Cloud, joins Katie Keith and Matt Cromwell for a show-and-tell style conversation about how each of them is using AI behind the scenes in their own businesses. The focus is on real operational use, building and replacing internal systems, automating testing, improving confidence when making changes, and reducing day-to-day friction for small teams. All three share concrete examples, trade-offs, and lessons learned, including where AI has helped and where it has not been worth the effort. We dig into: Where AI genuinely saves time in internal operations, and where it does not Replacing generic tools with custom internal systems built using AI • Using AI for automated testing and infrastructure confidence Why internal tooling is the most overlooked AI opportunity for product companies What this means for small teams who do not have dedicated ops or infra staff If you are building a WordPress product, SaaS, or any tech business and feel buried under internal processes, this episode shows how AI can help you run leaner without adding chaos.

In today's WordPress product landscape, support can make or break your business. But growing queues and a commitment to providing a great experience, your teams are often juggling multiple top priorities. In this episode of WP Product Talk, hosts Ian Misner and Zack Katz are joined by Ben Meredith to explore how AI can multiply your support team's impact without sacrificing the human touch. Drawing on his hands-on experience implementing AI-powered support workflows, Ben shares what "4x your team" actually means in practice. We'll cover: How to use AI in support "the right way" The human-AI hybrid model and where each does the heavy lifting Practical implementation without blowing up your existing workflow This episode is for product builders who are curious about AI in support but skeptical of the hype and want real talk about what works, what fails, and what's worth trying.

WordPress is moving fast on AI, and plugin builders need to keep up. On Jan 21 at 6pm UTC+1, WP Product Talk sits down with Jason Adams, Core AI Team Lead at Automattic, to unpack how plugins WordPress AI efforts are shaping what’s possible right now. Jason joins Zack Katz and Matt Cromwell for a practical conversation on where core AI is headed, how plugin teams can build on it, and what to pay attention to if you want your product to stay relevant as AI lands deeper in WordPress.

Today's users expect speed, clarity, and polish by default. In this episode of WP Product Talk, we dig into Product User Expectations and what WordPress product owners need to stop ignoring if they want to stay relevant. Carl Alexander joins Paul Carter, CEO of BuiltFast, to talk honestly about where products fall short and how teams can raise the bar without burning out. Join Matt Cromwell and Zack Katz live on January 14, 2026 at Noon Eastern Time for a practical conversation about performance, UX, and the real cost of excuses. This one is for builders who want fewer complaints, happier customers, and products that feel modern out of the box.

In this episode of WP Product Talk, hosts Zach Katz and Ian Meisner dive into the potential of MCP (Model Context Protocol) for WooCommerce product builders. Joined by Nik McLaughlin from SkyVerge, the discussion covers how MCP enables apps, tools, and AI models to communicate, its readiness for real-world use, and whether it's worth the investment. This episode explores the technical intricacies of MCP, its potential applications, and how it could revolutionize everything from store management to customer experience. They also tackle the challenges, risks, and the future of MCP in the WordPress ecosystem. Tune in for insights on how this technology could unlock new opportunities for product owners and developers.

Product positioning is one of those things everyone talks about, but very few get right, especially when a product’s value isn’t immediately obvious. In this episode of WP Product Talk, we’re going all in on what product positioning really means and how to make it work in the real world. Nathan Tyler, founder of BlinkMetrics, joins co-hosts Matt Cromwell and Zack Katz to unpack how founders can clarify their message, sharpen their positioning, and help the right customers “get it” faster. Join us live today at Noon ET for a practical, founder-focused conversation.

Join us for Making WordPress Weird: Nick Hamze on Building for Fun in WordPress, as we explore what happens when you stop taking things so seriously and start creating just because it’s fun. Nick Hamze is known for his playful, unconventional approach to building and his relentless push to keep the creative spirit of WordPress alive. From his pro-Wapuu advocacy to his experiments with AI and offbeat product ideas, Nick shows us why weirdness might just be WordPress’s greatest strength. We’re going live Wednesday, December 11 at Noon ET, with co-hosts Ian Misner and Matt Cromwell, who’ll help unpack how curiosity, experimentation, and a bit of chaos can lead to more meaningful work and maybe even better products. Follow Up with Nick Hamze This episode is a follow-up to our earlier conversation with Nick Hamze about building “fun, weird” things in WordPress and the hard truth behind it: shipping is easy now; distribution is not. Since our original episode in December 2025, WordPress quietly shipped a meaningful change: the Featured Plugins tab inside the Add New Plugins screen is no longer basically static. It’s now rotating every two weeks to spotlight newer plugins with fewer than 10,000 installs. In this special WP Product Talk follow-up, Nick joins Matt Cromwell and Ian Misner to unpack how the Featured Plugin experiment came together, what the selection criteria looks like, and why this kind of in-dashboard discovery is one of the highest-leverage changes WordPress can make for small plugin makers. We also dig into: Why the old Featured tab needed a reset The curation guidelines Nick is using (and why they matter) How the first featured plugins saw immediate install spikes (including Ollie Menu Designer) What a “fair” and sustainable discovery system could look like next (filters, categories, better browsing) How the community can participate without turning it into a popularity contest Links & Resources Featured Plugin discussion in WordPress Slack: https://wordpress.slack.com/archives/C0AJB2960NS Matt’s thread showing the Ollie Menu Designer download spike: https://x.com/learnwithmattc/status/2028804166747824311 This article at The Repository covers the conversation as well: https://www.therepository.email/the-wordpress-featured-plugins-tab-is-now-rotating-hidden-gems-every-two-weeks