Crickets to Cha-Chings

202. From $50 to Full-Time: Jay's Print-on-Demand Pivot to Creative Freedom

Crickets to Cha-Chings

Show Notes

Summary In this episode, Julie Berninger interviews Jay De Souza, who shares his journey from a stressful corporate job to becoming a successful print-on-demand entrepreneur. Jay discusses the importance of understanding customer needs, the significance of niche marketing, and the emotional aspect of selling products. He emphasizes the use of technology and tools to enhance business efficiency and the necessity of maintaining a positive mindset for long-term success. The conversation also covers emerging trends in the apparel market and practical tips for aspiring entrepreneurs. Takeaways Jay is about to cross 125,000 shirts sold on Amazon. Stress can manifest physically and is a silent killer. Designing for the customer is crucial for success. Niche marketing is essential for effective selling. Utilizing technology tools can streamline the design process. Selling emotions is key to connecting with customers. Competition in the market validates demand for products. A year of commitment is necessary for business success. Implementing what you learn is as important as learning itself. Quality design is essential; ugly designs won't sell. Chapters 00:00 Introduction and Milestones 01:58 Transitioning from Corporate to Print on Demand 07:34 Understanding Customer Needs 10:23 Niche Marketing Strategies 15:35 The Importance of Emotion in Design 24:34 Tech Stack and Tools for Success 31:05 Navigating the Algorithm: Understanding Customer Confusion 31:54 Targeting Big Niches: The Balance of Competition 33:13 Defining Your Ideal Customer: Niche Down for Success 35:07 The Importance of Keywords: Broad vs. Long Tail 36:50 Shopping Mindset: Understanding the Buyer's Perspective 39:00 Creative Chaos: Organizing Your Design Process 41:11 Emerging Trends: Summerween and Beyond 45:57 Nutrition Label Parodies: A Unique Design Opportunity 48:53 Researching Trends: Finding Your Target Demographic 52:59 Mindset Matters: Resilience in Business 57:44 Setting Realistic Expectations: The Long Game in Business

Watch this episode on YouTube: https://youtu.be/V3yHdicbwXo

Resources Free POD Workshop: https://goldcityventures.com/gifting-gold-podcast Free Digital Product Workshop: https://goldcityventures.com/workshop-pdcst Gold City Ventures Website: https://goldcityventures.com/pdcst Follow Jay on YouTube: https://www.youtube.com/@jayswayworks Check out Jay's Membership: https://go.goldcityventures.com/jays-way

More from Crickets to Cha-Chings

Oct 21, 2026

Discover how to use AI tools to create Etsy digital products, find profitable ideas, and save time without falling for misleading data. Julie Berninger and Sasha Hutchison share practical Etsy seller strategies, from keyword research and market analysis to holiday product ideas that can help your shop stand out. Learn how to create eye-catching mock-up templates and product listings, navigate platform policies, and prepare for the holiday season with Holiday Boot Camp events, templates, and prizes. Plus, discover why validating AI-generated research matters before investing time in a product idea—and how smarter digital marketing can support your Etsy growth.

Oct 14, 2026

Check out Anywhere Digital: https://go.goldcityventures.com/anywhere-digital What if you could automate your Etsy digital product listings instead of creating every one manually? Chris Meats from Anywhere POD and Anywhere Digital reveals how AI is transforming Etsy workflows—helping sellers create product listings, mockups, personalization, and digital downloads faster. See how Canva designs can be turned into multiple Etsy listings, how AI streamlines listing creation, and how built-in upselling and cross-selling can help increase sales. Whether you sell digital products or print on demand, these automation tools could completely change how you run your Etsy shop.

Oct 12, 2026

What if you could list 125 Etsy products in a week without sacrificing quality? Seven-figure Etsy seller Emily shares how she uses AI tools like Claude and ChatGPT to streamline her print-on-demand business and scale her shop more efficiently.

Oct 5, 2026

For the Fall 2026 Launch of E-Printables, Cody & Julie recorded a live workshop called "We've Sold 152,500+ Digital Products — Here's What Actually Works", and they're sharing it in its entirety in today's episode! If you're listening on the day this drops, you still have a chance to get in and claim some bonuses. 👉 Join the E-Printables Course: https://goldcityventures.com/e-printables-course/?utm_source=podcast&utm_medium=description&utm_campaign=sept2026&utm_content=fincon During the workshop, we cover: The products we'd sell now for your first 100 sales The Etsy change that has us testing something new​​​​​​​ Results from our 50 listings in 2 weeks challenge The A.I. shortcuts worth using and what to skip ​​​​​Beginner mistakes and how to avoid them 📚 Learn More 📚 👉 Join the E-Printables Course: https://goldcityventures.com/e-printables-coursehttps://goldcityventures.com/e-printables-course/?utm_source=podcast&utm_medium=description&utm_campaign=sept2026&utm_content=fincon Learn how to create and sell digital products on Etsy. This enrollment opportunity ends Monday, October 5th, at Midnight Eastern! Your course purchase includes a ticket to our Holiday Bootcamp Kickoff on October 6 with Cody and head coach Sasha, featuring a laptop giveaway.

Oct 2, 2026

Cody went to FinCon in Palm Springs to connect with other creators and came home with a fresh perspective on growing an online business. Between sharing the main stage and talking shop over lunch, he heard how successful creators turn their ideas into digital products and build businesses around the right customers. 👉 Join the E-Printables Course: https://goldcityventures.com/e-printables-course/?utm_source=podcast&utm_medium=description&utm_campaign=sept2026&utm_content=fincon In this episode of Crickets to Cha-Chings, Julie gets the stories behind Cody's trip, including a conversation with the team behind Dow Janes that stuck with him. What happens when you take one successful idea further instead of constantly starting over? How can a smaller audience support a big business? And what are creators doing to build more freedom into their lives? Cody shares the conversations that got him thinking, and we connect those lessons to our own experiences selling digital products on Etsy. Plus, we catch up on his first FinCon since publishing Retire by 30 and the connections that keep him coming back each year. Chapters 00:00 Behind the scenes at FinCon with Cody 01:38 How one good idea becomes your next opportunity 07:24 Small audience, big business: The power of the right niche 13:25 Building income that gives you more freedom 18:20 The conversations that happen after the sessions 22:47 Your invitation to Holiday Bootcamp 📚 Learn More 📚 👉 Join the E-Printables Course: https://goldcityventures.com/e-printables-coursehttps://goldcityventures.com/e-printables-course/?utm_source=podcast&utm_medium=description&utm_campaign=sept2026&utm_content=fincon Learn how to create and sell digital products on Etsy. This enrollment opportunity ends Monday, October 5th, at Midnight Eastern! Your course purchase includes a ticket to our Holiday Bootcamp Kickoff on October 6 with Cody and head coach Sasha, featuring a laptop giveaway.

See all episodes →