Crickets to Cha-Chings Podcast Summary: Episode 202 - "From $50 to Full-Time: Jay’s Print-on-Demand Pivot to Creative Freedom"
Release Date: August 14, 2025
Host: Julie Berninger, Gold City Ventures
Guest: Jay d' Souza, Founder of Jay's Way
Introduction
In Episode 202 of Crickets to Cha-Chings, Julie Berninger welcomes Jay d' Souza from Jay's Way to discuss his transformative journey from a stressful corporate IT role to achieving creative freedom through the print-on-demand (POD) business. This episode delves into Jay's strategies for scaling his Etsy and Amazon shops, the importance of niche targeting, effective use of technology, and the crucial mindset required for entrepreneurial success.
Jay’s Milestone and Transition to Entrepreneurship
Jay begins by celebrating a significant milestone: nearing 125,000 shirts sold on Amazon Merch, averaging 80 sales a day. (00:21) He attributes part of his success to his extensive experience on Etsy, where he also boasts over 124,000 shirt sales.
Quote:
"I'm at 124,022 shirts right now. So, yeah, I'm about to cross that. That's just on Amazon merch alone." (00:21)
Jay shares his turnaround from a 20-year graphic design career and a high-stress IT job at TD Bank. Facing burnout and health issues, he made the pivotal decision to leave his corporate life and pursue entrepreneurial endeavors in print-on-demand.
Quote:
"Stress really is truly a silent killer. So please, if you're feeling like you're any kind of which way, talk to somebody, get sorted because that stuff is no joke." (02:30)
Niche Selection and Design Strategy
A cornerstone of Jay's success lies in targeting specific niches rather than designing for the general public. He emphasizes the importance of understanding and catering to distinct customer segments to drive sales effectively.
Quote:
"If you try to sell something to everybody, you end up selling nothing to anybody." (10:09)
Jay discusses his focus on popular apparel such as T-shirts, while also branching out into hoodies and crewneck sweaters based on design performance. He highlights niches like bridal/bachelorette parties and various hobbyist groups (e.g., fishing, hunting) where niche-specific designs thrive.
Quote:
"Ultimately, it's about the customer that you're selling to. Right. And that kind of, you know, segues into, you know, you're not designing for everybody. You're designing to a specific, ideal customer." (06:10)
Leveraging Technology: Tools and Tech Stack
Jay underscores the significance of utilizing the right tools to streamline operations and enhance productivity. His tech stack includes:
- Erank and Everbee: For Etsy keyword research and trend analysis.
- Insight Factory: For comprehensive trend reports, despite its higher cost.
- ChatGPT: Customized with his own data for authentic responses and deep research.
- Design Software: Primarily Adobe Illustrator, with increasing use of Kittl, Ideogram, and Playground for AI-centric design tasks.
Quote:
"Erank and Everbee, Absolutely. I'll use both. I am a Chrome extension. You know, don't want to curse on here, but yeah, I love Chrome Extensions." (16:00)
Jay explains how these tools help him identify trending designs, calculate profitable margins, and manage listings efficiently, ensuring that his products remain competitive and profitable.
Selling Emotion Through Designs
Jay emphasizes that successful POD products sell emotions rather than just the product itself. Whether it's humor, pride, or a sense of belonging, the emotional resonance of a design drives customer engagement and purchases.
Quote:
"You're selling the emotion that you're selling. You, like, think of any of you out there that are moms, you know, buying stuff for your teenage kids or whatever it is every time you give them..." (24:02)
He illustrates this by explaining how a T-shirt design can evoke laughter or pride, making it a memorable gift that strengthens the emotional connection between the giver and receiver.
Identifying and Capitalizing on Trends: Hidden Gems
Jay shares insights into spotting and leveraging emerging trends within the POD space. He highlights specific trends such as:
- Summerween Crossover Designs: Blending summer themes with Halloween elements to create unique, seasonally versatile products.
- Nutrition Label Parodies: Humorous takes on traditional product labels, incorporating playful elements like QR codes for added engagement.
Quote:
"Summerween is just crossing kind of like summer and Halloween... it's more of like the rudimentary designs, right? The organic kind of hand-drawn doodle aesthetic." (40:18)
Additionally, Jay points out niche opportunities like home staging and Airbnb decor, which present untapped markets with consistent demand for fresh designs.
Mindset and Resilience in Entrepreneurship
A significant portion of the conversation revolves around the mindset required to sustain and grow a POD business. Jay advocates for resilience, long-term vision, and the ability to learn from setbacks.
Quote:
"You get knocked down, you have to get back up... Growth happens outside of that comfort zone." (51:51)
He discusses overcoming negativity bias, the importance of sticking with a niche for at least a year before pivoting, and balancing continuous learning with actionable implementation.
Quote:
"Winners are learning and implementing. Learning and implementing. Learning and implementing." (59:00)
Jay encourages entrepreneurs to view their ventures as businesses rather than hobbies, emphasizing strategic planning, consistent effort, and emotional intelligence.
Conclusion and Final Thoughts
Jay wraps up the episode by reinforcing that while his methods have worked for him—coined as "Jay's Way"—there are myriad paths to success in the POD landscape. He highlights the importance of both creative passion and data-driven strategies in achieving sustainable growth.
Quote:
"It's not about that this didn't work. It's that this didn't work yet." (58:35)
Listeners are encouraged to explore his resources, including his YouTube channel @Jaysway Works and membership community jaysway.org/innercircle, for deeper insights and support.
Key Takeaways
- Target Specific Niches: Focusing on well-defined customer segments leads to better sales and brand loyalty.
- Utilize Effective Tools: Leveraging tools like Erank, Everbee, and ChatGPT can streamline operations and enhance product offerings.
- Sell Emotion, Not Just Products: Designs should resonate emotionally with customers to drive engagement and purchases.
- Stay Resilient and Adaptable: A strong, positive mindset and willingness to adapt are crucial for long-term entrepreneurial success.
- Balance Creativity with Strategy: Combining creative passion with data-driven strategies ensures both product appeal and market relevance.
Stay Connected with Jay’s Way:
- YouTube: @Jaysway Works
- Membership Community: jaysway.org/innercircle
This episode offers a comprehensive roadmap for aspiring and established POD entrepreneurs looking to scale their businesses effectively while maintaining creative freedom and emotional resilience.