Turning a Simple Hobby into a Global Community with Jordan Truster and Jillian Reece

Anika sat down with Jordan Truster and Jillian Reece, the co-founders of Loveleigh Loops, to explore how they turned a shared hobby into a thriving, community-driven education business teaching modern calligraphy to more than 60,000 students worldwide. Despite their backgrounds in engineering and data analysis, Jordan and Jillian leveraged analytical precision to break down artistic skills into approachable, step-by-step frameworks. The conversation covers the power of starting with digital downloads on Etsy, building engaged student communities, scaling intentionally without losing trust, and why analogue hobbies provide a vital, mindful escape in an increasingly automated world.
In This Episode
Turning an accidental wedding hobby into a global online calligraphy education and community business
Why an analytical, step-by-step teaching style makes creative skills approachable for beginners
Scaling from local in-person workshops to digital Etsy downloads and structured online courses
The unique dynamics and mutual support of running a successful business as twin co-founders
Experimenting with platforms like Teachable, Circle, and School to find the right student experience
Cultivating a positive, spam-free community centered around creativity, mindfulness, and slow living
Balancing email marketing cadence with high-value newsletters and strict subscriber preference tags
Embracing analogue hobbies as a powerful, meditative counter-trend to AI and digital fatigue
Shifting creator focus from endless complexity and self-promotion to student success and simplification
Timestamps
00:00 Introduction: Unraveling thriving business stories and welcoming Jordan Truster and Jillian Reece
01:42 The origin story: From childhood art enthusiasts to reconnecting through wedding calligraphy
03:29 The "Letter Logic" breakthrough: How analytical thinking transformed artistic teaching methods
06:04 The evolution of scale: Transitioning from in-person workshops to Etsy digital downloads and online courses
08:45 Co-founding as twins: Leveraging shared minds, complementary strengths, and life transitions
11:33 Platform evolution: Experimenting with Teachable, Circle, and School for online communities
13:26 Cultivating positivity: Building an encouraging, spam-free community of engaged learners
17:10 Writing the book: Collaborating with a publisher to bring calligraphy into physical form
19:07 The analogue renaissance: Using calligraphy as a meditative, mindful escape from AI and digital noise
22:32 The shift to student-centric design: Simplifying courses and focusing on accountability and experience
27:54 Email marketing mastery: Balancing monthly newsletters, valuable resources, and strict segmentation
31:11 Passing the torch: Inspiring the next generation and modeling creativity for young daughters
32:02 Key takeaways: Focusing on student experience and leaning into your natural strengths
34:00 Guiding stars: Favorite mantras on slowing down and building great things through small steps
Key Insights & Takeaways
Insight 1: Leverage Your Unique Backgrounds
Your past professional or academic experiences—even analytical ones like engineering and data science—can bring fresh, structured perspectives to creative industries, making complex skills approachable for others.
Insight 2: Prioritize the Student Experience Over Complexity
Instead of trying to prove your expertise by cramming endless information into a course, focus on simplification, accountability, and making it as easy as possible for students to succeed.
Insight 3: Cultivate Intentional Communities
Building a successful online community relies on fostering genuine connection and shared values rather than allowing spaces to become breeding grounds for cross-promotion and spam.
Insight 4: Embrace the Power of Analogue
In a world dominated by AI, automation, and fast digital communication, hobbies that require slowing down and working with your hands offer essential mental health benefits and ...