EPISODE · Jun 13, 2025 · 39 MIN
Sell Stories Not Product - Kyle Cole
from Checkin to Checkout · host Justin Aronstein
Most e-commerce stories start with product-market fit. This one started with Frodo. On this episode of Check-In to Check-Out, we talk with Kyle Cole, co-founder of The Hero’s Journal—a journaling brand built on the idea that life gets easier when you start seeing yourself as the main character. What started as a nerdy side project turned into a seven-figure DTC brand powered by story, community, and a refusal to send boring emails. Kyle opens up about: Accidentally going viral during quarantine with a “Quarantine Quest” Scaling fulfillment from garage to 3PL—and the painful (but hilarious) budget mistake he made What every e-commerce leader gets wrong about community building How to forecast without deluding yourself Why the best marketing emails sometimes have no CTA If you’ve ever tried to justify a warehouse lease based on “the traffic you're manifesting” or had your team melt down over a 3PL gone rogue, this one’s for you. It’s funny, vulnerable, and weirdly practical. And yes, we talk about iOS 14. Perfect for: Directors of E-Commerce, DTC operators, brand builders who think “community” isn’t just a Slack channel Listen in and remember: you are the hero. Just maybe... also the operations oracle. Chapters (00:00:00) - E-Commerce: The Hero's Journey(00:01:40) - Kyle on the Podcast(00:02:11) - What's Your Day to Day at Hero's Journey?(00:02:42) - Have You Had A Good Week?(00:03:32) - What's Your Best Strengths and Weaknesses?(00:08:17) - The Story of The Book(00:09:09) - Startups as a Way to Get Out of Debt(00:12:41) - Do You Wish You Had Done This Lesson?(00:17:13) - How To Grow an E-Commerce Business(00:21:45) - Being Flexible in an E-commerce Business(00:22:56) - Community as a Force multiplier for E-Commerce(00:29:06) - Building a Community for Your Product(00:31:32) - Send inspirational emails to your fans(00:35:58) - E-Commerce Leadership: The Hero's Journal
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Sell Stories Not Product - Kyle Cole
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