ABOUT THIS EPISODE
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 flow states.
Insight 5: Protect Your Email List Trust
Maintain long-term audience trust by sending thoughtful, high-value content, providing clear opt-out preferences, and communicating consistently without forcing arbitrary daily cadences.
Insight 6: Lean Into Strengths and Curiosities
Sustainable business growth comes from pursuing projects you genuinely enjoy alongside a trusted partner, rather than chasing every high-ticket trend that doesn't fit your core passion.
Resources & Links Mentioned
- Loveleigh Loops (Official website for calligraphy courses, free resources, and community)
- Lettering for Planners by Jordan Truster and Jillian Reece
Teachable, Circle, and School (Platform tools discussed for courses and communities)
About Jordan Truster and Jillian Reece
Jordan Truster and Jillian Reece are the twin co-founders of Loveleigh Loops, where they have taught modern calligraphy to over 60,000 students worldwide. Combining backgrounds in mechanical engineering and data analysis with a passion for art, they built a thriving digital education platform, active online communities, and co-authored the book Lettering for Planners. Today, they champion the joy of slow, analogue hobbies, helping students find mindfulness and creative confidence through the art of beautiful writing.
Connect with Jordan and Jillian
- Website: https://loveleighloops.com/
- Instagram: https://www.instagram.com/loveleighloops
- Calligraphy Together: https://www.calligraphytogether.com/
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