Your Side Gig Can Make You or Break You

Running a product on the side sounds exciting, but it comes with real challenges. Our guest Yuri Gerasymov shares his 8-year journey of building and maintaining a product while working a full-time developer job and raising three kids. He will break down how to find ideas, how to get started, and what it takes to keep momentum without burning out. Whether you're a web developer or agency owner considering building your own product, this episode explores when to outsource, what to keep in-house, and how a side gig can either make you — or break you.

Matt "TK" Taylor, and Matt Kane from Cloudflare join WP Product Talk to discuss EmDash. Is it an opportunity for WordPress products to expand their reach, or a threat to our ecosystem? In this special episode of WP Product Talk recorded live at PressConf in Tempe, Arizona, hosts Matt Cromwell and Zack Katz sit down with Matt "TK" Taylor and Matt Kane from Cloudflare to unpack the buzz around EmDash — a new CMS positioned as a “spiritual successor” to WordPress. The conversation dives into how EmDash came to life, its modern architecture built on Astro, and whether this new platform represents a genuine opportunity for WordPress product creators or a potential threat to the ecosystem. From plugin sandboxing and security improvements to portability, hosting flexibility, and AI-native workflows, the guests share their vision for what a CMS built in 2026 should look like. The discussion also explores the business and community implications: plugin marketplaces, monetization opportunities, governance, and whether EmDash could spark a new “gold rush” for developers. With early community momentum, open-source ambitions, and strong interest from product builders, the panel weighs how EmDash might reshape the future of WordPress — or push it to evolve faster. If you're a WordPress product creator, agency, or developer wondering whether to pay attention to EmDash now or wait and see, this episode breaks down the risks, opportunities, and what to watch next.

Moving from client services to SaaS sounds like a technical challenge—but what if the real hurdle is market fit? In this episode, Matt Schwartz, Founder of Checkview, shares how his biggest lessons weren’t about code, but about deeply understanding customers, shaping a roadmap, and questioning assumptions about where agencies truly find value. As he transitioned from services into product, Matt discovered that deciding what to ship—and just as importantly, what not to—was far more complex than building the product itself. Join co-hosts Zack Katz and Katie Keith on April 1 at Noon Eastern / 6pm CET as they unpack the realities of customer discovery, SaaS vs. plugin positioning, education-driven marketing, and creating meaningful early feedback loops. This conversation is especially relevant for WordPress product founders and agency owners considering the leap into SaaS, offering honest insights into the messy, high-stakes work of finding real market fit before it’s too late.

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

Join us for an upcoming episode of WP Product Talk titled “All about Growth Marketing” with Stuart Brameld, founder of GrowthMethod, on March 18 at 6:00 PM CET. Matt Cromwell and Ian Misner will dig into what growth marketing for software products really looks like when you’re trying to build traction in a competitive market. This conversation is built for WordPress product owners who want clearer ways to attract, convert, and keep customers without wasting time on random tactics. If you want practical ideas for sustainable growth, this is one live episode you won’t want to miss.

Behind every “simple” website is a complex WordPress agency tech stack—often made up of 10 to 30 disconnected tools for hosting, security, backups, reporting, and more. In this episode, Emmanuel Khoury, Co-founder of WPStaq, pulls back the curtain on what’s really happening inside agencies and why fragmented systems lead to higher costs, slower delivery, stressed teams, and unhappy clients. We’ll explore what happens when agencies consolidate their workflows, reduce tool sprawl, and rethink how their WordPress agency tech stack is structured. If you build products for agencies—or run one yourself—this conversation will help you understand where operational friction lives and how unifying tools can reduce support noise, overhead, and churn while improving client outcomes.

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.