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.