How This Entrepreneur Turned a Modern Calligraphy Skill Into a Booming Side Business

How This Entrepreneur Turned a Modern Calligraphy Skill Into a Booming Side Business

How This Entrepreneur Turned a Modern Calligraphy Skill Into a Booming Side Business

Lori Shen is the founder of Letter On!, a modern calligraphy and design business specializing in Hawaiian designs. Letter On! sells a variety of products from greeting cards to prints to rubber stamps. The company also offers custom design services for items such as welcome signs, place cards, envelopes, and chalkboard signs. Shen attributes her entrepreneurial spirit to her family. “I’m a product of two small business owners. My parents started an orchid nursery in Waimanalo, Hawaii, the year before I was born and still run it today,” she said. “I grew up watching them navigate the ups and downs of operating a small business, but I never fully appreciated all the challenges they faced until now.”

From Fun Hobby to Lucrative Side Hustle

I worked in public relations for about 15 years. Two years ago, I became a mom for the first time. I took a modern calligraphy workshop on a whim. At the time, it was something I kept up in my personal time. I just did it for fun. The more I did it, the better I got. I started designing things and giving them away as gifts. I got a lot of feedback from friends that I might want to think about opening my own shop.

I launched Letter On! as an outlet for myself. I was looking for a way to earn a little extra cash to help cover the cost of household expenses. Diapers add up! It is a side hustle, but it is also a way for me to express myself and connect with others. I had no idea what kind of reception it would receive, so it’s been so rewarding to see it resonate with so many people.

Managing Business Finances

I have bootstrapped the business entirely. To open an Etsy store, the cost is minimal. I don’t carry a lot of inventory at any given time to keep costs down. At first, I made everything to order, so I didn’t have to invest in a lot of materials up front.

I use my personal credit card for business expenses at this point. I have an Amazon rewards card and I order a lot of my supplies on Amazon. I have a budget and I stick to it. I’ve also downloaded apps like Harvest to keep tabs on cash flow.

Business Challenges and Rewards

One of my biggest challenges has been digitizing my work. I learned calligraphy with a paintbrush and ink, but it didn’t take long before orders for wedding signs came pouring in – I opened my shop just in time for wedding season. So, before I knew it, I needed to operate digitally to respond to what clients wanted and to speed up my workflow. So, I had to teach myself digital imaging apps. I remember my first project took me so many long nights. I watched countless YouTube videos to teach myself how to digitize my intricate calligraphy.

The biggest reward for me is definitely the feedback I get from customers. It’s great to connect with others and to see my designs resonate with people. I recently got a review on Etsy from a woman who bought my “I Lava You” card. It is a special phrase she shares with her husband. She surprised him with the card and he loved it. Stories like that fill my heart!

Business Lessons Learned

I’m a first-time entrepreneur. I’ve always worked for other people, whether at large billion-dollar companies or startups. Being an entrepreneur has really rounded out my business skill set. I’m learning all aspects of running a business.

For example, I have learned so much about shipping. Shipping was a completely foreign world to me. Initially, I wasn’t extending the full cost of shipping on small items to my customers. Obviously, I couldn’t sustain that for very long. But, then I sought out other sellers to understand their shipping operation. I got smart. I started selling card packs so that customers could get more for the same shipping cost and I learned how to package smarter. In my parents’ orchid business, they had many challenges streamlining their shipping process out of Hawaii. So, our conversations have become a lot more meaningful as I connect with them on a whole new level!

Something smart I did at the beginning was to hone in on my brand. When I first started my shop, I listed all the designs I had made. But, I soon found that my top sellers were the ones designed with my Hawaiian twist on them. That’s what makes my products unique and unlike things you can find in other stores. It wasn’t long before I cut out the rest to focus on my Hawaiian line.

Advice for New Entrepreneurs

Give yourself the space to learn and grow. It’s so easy to get caught up in the day to day, so I try to carve out at least an hour a week to work on myself. I either try to pick up a new skill – I still watch YouTube tutorials! – or make a new connection. I’ve met a lot of fellow makers on Etsy and Instagram. The connections have been priceless, leading to new business opportunities.

What’s Next for Letter On!

“She Lives Aloha Every Day” was the first print I designed. I design for people who live this intention and I look forward to continuing to connect with people who aspire to this lifestyle.

This article was originally written on August 2, 2017 and updated on February 1, 2021.

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