This Side Hustle Spotlight Q&A features Krista LeRay, the 34-year-old founder of needlepoint store Penny Linn. She lives with her husband and two children in Westport, Connecticut. Responses have been edited for length and clarity.
Image Credit: Courtesy of Penny Linn. Krista LeRay.
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What was your day job or primary occupation when you started your side hustle?
Before starting Penny Linn, a new-age needlepoint store offering hand-painted canvases, accessories and more, I was a full-time influencer running my blog, Covering The Bases. I started the blog in 2013, but I only took it full-time about a year before starting Penny Linn. While managing the blog, I had a corporate career at Major League Baseball, where I worked on the social media team for over five years.
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When did you start your side hustle, and where did you find the inspiration for it?
I initially learned to stitch from my grandma, who inspired the name of the business, and then I really got into it in college at the University of Kentucky. I picked it back up again in 2018 when I started stitching custom belts for my dad and husband, and a ring bearer pillow for my wedding in 2019. Little did I know that this would be the perfect hobby to fall back in love with as the pandemic approached.
As I got back into stitching, I quickly stitched through my stash of canvases and was disappointed with both the in-person and online needlepoint shopping experiences. It felt antiquated; there weren’t many sites with a good user experience, a handful of the shops made you call to order, and the designs felt very mature. I found myself wishing there were more fun and better accessories and canvases, so I started making them after my search came up short.
Image Credit: Courtesy of Penny Linn
What were some of the first steps you took to get your side hustle off the ground? How much money/investment did it take to launch?
When I started painting my own canvases, I wasn’t even in the mindset of starting a business; it was still just a hobby for me. I probably spent under $100 buying a blank canvas on Etsy and paint at Michaels, and painted the infamous Ralph’s Coffee cup for myself. When I shared it on my Instagram, I had an overwhelming number of followers ask to buy one, so I knew my followers were also interested in needlepoint.
As I began searching for cuter accessories for myself, I found that many custom items had a 100-item minimum. At the time, I had a business bank account for my blog, so I used that money to order the inventory and knew that I could at least sell 90 of them to my followers who also needlepointed. After making a few canvases and seeing the demand, I realized I had enough ideas to launch a larger collection online. So I bought the smallest Shopify package, started sourcing needleminders and project bags, and recruited my friends and family to help paint canvases.
All in all, I spent about $5,000 on the initial inventory for our accessories and an additional $2,000 on shipping materials, canvas tape, etc., but none of this accounted for my time painting the canvases one by one, which was the biggest investment.
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If you could go back in your business journey and change one process or approach, what would it be, and how do you wish you’d done it differently?
Looking back on how I built my business, it’s a catch-22; if I had known what I know today, I might have done it differently. However, having my hands in every aspect of the business has brought me a great deal of knowledge and appreciation that continues to shape the business.
In the beginning, I hand-painted nearly every canvas, which took many, many hours, but it kept costs low since my labor was essentially free and gave me control over my inventory. If I had known that people outsourced painting, it would have saved me so much time and energy, but doing it myself taught me the value of a hand-painted canvas.
Similarly, I wish I had hired people at the beginning to take more off my plate, but by doing it all, I learned valuable lessons and knew how I wanted every aspect of the business to run. I don’t think Penny Linn would be such a thoughtful and impactful brand today if I hadn’t had my fingers on every aspect of the business in the beginning.
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When it comes to this specific business, what is something you’ve found particularly challenging and/or surprising that people who get into this type of work should be prepared for, but likely aren’t?
The reason Penny Linn has been so successful as a business, and also in reviving the cultural love for needlepoint, is that we brought much-needed innovation to the industry. I never expected the amount of pushback from vendors and industry vets I received. Across the board, people pushed back on our ideas and how we ran our business.
Today, we have found partners who believe in our growth and are building with us. When we launched our acrylic line in 2022, there was so much chatter online that it wasn’t innovative or unique, but today we hold a patent for the design, and it’s one of our bestselling lines. We also take a slightly smaller wholesale margin than the industry standard because I believe in making needlepoint accessible. Our wholesale partners were initially adamant that it wouldn’t be successful, but it has proven otherwise. I developed a thick skin while blogging and learned to shut out the noise, which has followed me into Penny Linn as we continue to shake up the industry.
Image Credit: Courtesy of Penny Linn
Can you recall a specific instance when something went very wrong? How did you fix it?
I vividly remember one of our first bag launches, which did not go as planned. It was a beautiful project bag with leather and PVC that we sold through so quickly! As I was packing them, I tested a few of the zippers and was very disappointed to find that they stuck and were difficult to open, despite the samples working perfectly. I reached out to each customer who had ordered them and let them know that the bags weren’t up to our standards. I offered them a full refund if they wanted to return the bag or a discount if they wanted to keep it.
This became one of my biggest rules in business: When anything goes wrong, I need to take ownership and work to rectify it immediately. Our community was beyond appreciative of how proactive we were, and most ended up keeping the bags. We put the rest of the bags on clearance and now work with our team and vendors to ensure we have quality control measures in place.
How long did it take you to see consistent monthly revenue? How much did the side hustle earn?
In the first six months after we launched, the only consistent revenue was what we generated during launches. Everything would sell out so quickly that we wouldn’t have any inventory left until the next launch. We would often have a day or two without sales in between launches, which wasn’t a sustainable way to run a business. To prevent this, we started producing more inventory and introduced our Penny Linn Collective, allowing us to bring on designers who expanded our offerings. Our designer collective has been fruitful for us over the past five years, and we continue to grow it today.
We started seeing more consistent revenue in year two, doing just over $30,000 per month. The popularity of our launches started to level out, and we could better forecast inventory to keep our income steady. It was such a big deal for us at the time to reach these numbers, but we do that in a day now. Each year has been drastically different in terms of demand, and about every six months, we reach an inflection point where we need to increase quantities even more.
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What does growth and revenue look like now?
It’s been really exciting that Penny Linn has doubled or tripled each year. In 2024, we did $4.4 million in revenue, and we have already surpassed that and are on track to double it in 2025. We are currently averaging $570,000 per month. Whatever I think our ceiling might be, we come in and double it each year. Our growth has been so explosive that I do expect it to start leveling out in the next year or so, but there is still so much opportunity for the business.
My mind is always racing with new ideas for the brand as we expand our product offering, launch new designers under the Penny Linn Collective and bring new accessories to market. Our store opening in Norwalk, Connecticut, earlier this year was a huge milestone for us, and now we are exploring what more stores might look like. I don’t see our growth slowing down anytime soon.
Image Credit: Courtesy of Penny Linn
What do you enjoy most about running this business?
I honestly love what I do so much and find great fulfillment in it. I feel so much pride, excitement and joy thinking about what we’ve created at Penny Linn and the business I’ve built in under five years. It’s nothing I could have ever imagined as my career or what I expected Penny Linn to grow into. We haven’t seen many bumps in the road yet, and keep having success after success, which energizes me to keep going.
I pride myself on the fact that Penny Linn is “by a stitcher for a stitcher,” and there is nothing more satisfying as a needlepointer to want something in my collection and to be able to make it. I’m privileged to have the ability to work with our vendors to create the products of my dreams, and it’s just as exciting to see how much our community loves them.
I also find so much joy in the change we have brought to the industry and how we have been able to bring needlepoint to the forefront for a new generation. It’s crazy to sit back and think that my brand has revived a centuries-old tradition and built it into something that will continue to live on and evolve for generations to come.
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What’s your best business advice?
The first is, “If you don’t ask, the answer is always no.” People are often scared to reach out because they are afraid of rejection, but my motto is always to ask, and if they don’t reply, it’s still not a no. If they don’t respond, it’s not the end of the world, but the opportunity for the answer to be yes is so much greater.
My second is to learn the difference between constructive feedback and criticism. If someone doesn’t like you or your business, they will never have anything nice to say, and it’s not worth listening to. However, if they are a loyal fan and a frequent shopper, and they comment on how a product or process might be improved, it’s worth listening to. It’s easy to get lost in the negative feedback, but the faster you learn what is worth listening to, the better decisions you will make for your business.
