Former pastor turned founding product marketer, Collin Mayjack, the founding product marketer at Sybill, joins me to unpack the messy middle of reinvention: grieving a life-long calling, rebuilding identity, and finding purpose across multiple “buckets” instead of one all-consuming job. Collin also shares how he broke into PMM, why he prefers scrappy founding roles over big-company “persuasion tours,” and the first-30-days playbook he actually uses (ship something fast, earn trust, then formalize the charter). We also get spicy on transparent pricing, creative ownership, and holding healthy boundaries when startup pace meets family life.

Head of Marketing at Vector, Jess Cook, drops in for a joyful, very Midwestern chat about building a brand people actually like. We trace her arc from writing jokes on McDonald’s Happy Meal boxes to directing video, running the iconic Cottonelle “Roll Poll,” and then leaping into B2B at Fastly. Jess unpacks why brand is the rising tide, how Vector builds in public with founder and team personas, and why marketing to marketers demands real originality. We also talk confidence, leadership, and keeping receipts for tough days. If you’ve felt allergic to “best practices” and crave marketing that’s human, funny, and effective, this one will light you up.

Director of Marketing at Parakeet, AJ Kissh, joins Struggle Huddle to talk about turning CRO instincts into a brand voice people actually want to hang with. We dig into why semantics matter (“say it so a 10th-grader gets it”), how AJ treats websites as a 24/7 ad, and the headline that finally clicked for Parakeet: “We write, test, and send better cold emails.” We also get real about experiment discipline (what to measure, how long to wait), pushing LinkedIn tone without going cringe, and why AI risks creating a “new vanilla.” In the Struggle segment, AJ opens up about imposter syndrome and shipping with conviction even when the data’s not there—yet.

Listen for: practical copy tweaks, channel-by-channel tone, and a simple framework for deciding when to pivot vs. let it run.

In this episode of Struggle Huddle, I sit down with customer researcher (and former therapist) Hannah Shamji to unpack the art and science of truly great interviews. We talk about her winding path from government healthcare to Copyhackers to running her own research practice, and how her therapeutic training completely transformed the way she builds safety, earns trust, and gets people to share what actually matters.

Hannah shares her blueprint for kicking off a call without awkward small talk, why safety beats rapport, and how to “poke around” and check your bias so you uncover deeper insights. We get into rabbit holes, reading energy, and why curiosity (not a perfect script) is the real superpower. We also tackle the tension between AI speed and human rigor in research—and what that means for the future of our work.

Whether you’re a marketer, founder, or just someone who wants to get better at asking questions, this one’s packed with practical takeaways and mindset shifts you can start using immediately.

This week on Struggle Huddle, I talked to the Rob Lennon — founder of Lennon Labs, master of AI prompts, and the guy who accidentally made $10k in a day off a landing page he published on Christmas Eve. (Casual.)

We got into:

• the magic of giving AI examples (not just vibes)

• why your vague little prompts aren't working

• how to actually train your robot assistant (like, for real)

• and the philosophy of feelings, personhood, and whether a Star Trek reference makes AI better at math (spoiler: it does???)

We also talked about audience building, content systems, high-ticket offers, and the feeling of oh no people are paying me real money.

This was one of my favorite conversations yet. Rob’s thoughtful, curious, and so damn good at explaining the weird mystery box that is ChatGPT.

Welcome to Episode One of The Struggle Huddle, where we kick things off with Max DB: content wizard, entrepreneur, website roaster, and all-around delight.

We talk about how Max fell into marketing by accident, became a community manager before it was a real job, and slowly shape-shifted into one of the sharpest SEO and CRO minds on the internet. He claims it’s all because he’s a good writer. I believe him.

In this episode, you'll hear: — The difference between “vibe writing” and actually knowing what you're doing — Why your click-through rate might not matter at all — What to change on your homepage before someone cries — Whether being a little data dweeb is required to succeed in SEO (answer: kinda) — And how marketing is actually just going to the gym, but for your brain

Max also talks about running four businesses at once, working a billion hours a week, and finding peace by outsourcing the stuff he doesn’t want to learn. If you're burnt out, building something, or simply baffled by what CRO even is, this one's a banger.

Struggle Huddle is officially back.