We’re excited to introduce you to the always interesting and insightful Kelsey Settle. We hope you’ll enjoy our conversation with Kelsey below.

Alright, Kelsey thanks for taking the time to share your stories and insights with us today. Often outsiders look at a successful business and think it became a success overnight. Even media and especially movies love to gloss over nitty, gritty details that went into that middle phase of your business – after you started but before you got to where you are today. In our experience, overnight success is usually the result of years of hard work laying the foundation for success, but unfortunately, it’s exactly this part of the story that most of the media ignores. Can you talk to us about your scaling up story – what are some of the nitty, gritty details folks should know about?

You know, people love to say, “Oh, Green Roost is such a success, you’re so lucky!” But the truth is, there were a lot of long nights and trial-and-error moments before it really took off. When I became the owner of Green Roost in 2011, I was just a 20-something girl with a passion for bringing purposeful products to my community. But it wasn’t until I started curating things with a deeper meaning – like sustainable brands and items that give back – that things really started to click.

Scaling up wasn’t some magical, linear process. It was more like a rollercoaster that sometimes felt like a dumpster fire. I think back to a pivotal moment during the charm bracelet craze – remember “those” bracelets? My store was overflowing with them. It was great while it lasted, but when that trend ended, I was left staring at shelves full of inventory that no longer aligned with the Green Roost vibe. That was a tough (and expensive) lesson in staying true to my brand, no matter what’s trending. It forced me to realign my focus on things that really matter to me and my customers – community, sustainability, and purpose. That shift? Total game-changer.

Another big part of my growth was realizing that scaling a business isn’t just about selling more stuff – it’s about growing as an entrepreneur. After years of learning the ropes of retail in a small town, I hired a business coach and joined my first mastermind. This decision changed my whole outlook on business. I knew I wanted to help other shop owners experience this same success. That’s how Retail Rituals came to life. I’ve seen firsthand the magic of owning a small-town business, but it’s also a hustle, and I wanted to create a space where other retailers could get the support and guidance they need to thrive.

So, scaling up has been a mix of messy moments and magical breakthroughs. Growing Green Roost while launching Retail Rituals has been a wild ride, full of lessons I didn’t even know I needed. And honestly? I wouldn’t change a single bit of it. It’s been the best, most unpredictable journey – and I’m still figuring it out as I go.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

I became the owner of Green Roost back in 2011, but my journey in the retail world actually started long before that, when I took my first job in a boutique at age 16. I’ve spent over two decades in retail, learning the ins and outs of the industry from the ground up. From small town retail, big box giants, to working the roads as a sales rep and now ownership, I’ve worn all the hats.

I took over Green Roost in 2011, with the goal of making it more than just a boutique – I wanted it to be a place where every purchase had a purpose. Over the years, we’ve curated products that are sustainable, give back, and most importantly, make our customers feel confident and seen.

But my journey didn’t stop at running a retail shop. I’ve always had a soft spot for other small-town entrepreneurs who are building their dreams from scratch. That’s how Retail Rituals came to life. After years of figuring out how to navigate the ups and downs of retail, I felt a calling to help others on their business journeys. Retail Rituals is a coaching business focused on empowering small-town retailers to thrive, especially when it comes to big moments like the fourth quarter. My coaching isn’t cookie-cutter; it’s about digging into the unique challenges of each business and helping owners find their magic – whether it’s maximizing holiday sales, attracting ideal customers, or navigating those tricky growth periods.

Over the years, I’ve learned how important it is to pivot and adapt without losing sight of your core values. I’ve taken those lessons and woven them into both my businesses – at Green Roost, we’ve built a reputation for being thoughtful and impact-driven. And at Retail Rituals, I use my retail experience to help fellow shop owners avoid common pitfalls and succeed in ways that feel authentic to them.

What I’m most proud of is the community I’ve built around both businesses. Green Roost has become more than a boutique; it’s a space where customers feel welcomed, appreciated, and part of something bigger. We don’t just sell products – we offer goods with a story, a purpose, and a positive impact on the world. And with Retail Rituals, I’m just beginning to coach other shop owners through their toughest times, helping them find strategies that actually work for them and their customers. There’s nothing quite like seeing someone turn their small-town shop into a powerhouse of impact.

What sets me apart is the connection I have with people. I’m not just focused on retail as a business – I’m focused on it as a way to build relationships. Whether you’re a customer walking through Green Roost or a client at Retail Rituals, I want people to feel like you’re being heard, supported, and empowered.

Let’s talk about resilience next – do you have a story you can share with us?

Resilience is one of those words that sounds nice on paper, but it gets real when you’re in the thick of a challenge. For me, one of those defining moments came in the form of a lot of charm bracelets – from a brand that shall not be named. When I first started carrying the brand, it was a dream come true. They were flying off the shelves, customers couldn’t get enough, and Green Roost was buzzing with energy. But then the trend began to fade, and I found myself sitting on an overwhelming amount of inventory that no one was buying anymore.

I jokingly call it my “charm bracelet PTSD” now, but at the time, it was no joke. I had so much invested in this one brand, and when the bottom dropped out, it felt like I was being buried in unsold product. It was a tough moment that tested my ability to pivot and adapt. I had to get creative, think outside the box, and most importantly, learn a valuable lesson: never rely too heavily on one trend.

That experience shaped how I approach my business today. It taught me to stay grounded in my core values of offering products that are purposeful, sustainable, and timeless, instead of chasing trends. Green Roost emerged stronger because of that lesson – we’ve become a place where customers know they’re getting something with meaning, not just what’s “hot” at the moment.

So, while I laugh about my charm bracelet days now, they were a turning point in my journey. It was a hard lesson, but it pushed me to be more resilient and thoughtful about how I grow my business.

Have you ever had to pivot?

When the COVID-19 shutdown hit, like so many small businesses, Green Roost was thrown into complete uncertainty. Suddenly, the foot traffic that had been the lifeblood of our store came to a screeching halt, and I remember thinking, “How are we going to survive this?” It was one of those true lemons-to-lemonade moments.

With our doors closed, I knew we had to pivot fast. We had always been focused on building relationships in person, but now the challenge was: how do we translate that same connection online? We didn’t have much of an online presence before, but the shutdown forced us to develop a website and get our products in front of customers who were now shopping from their couches.

It was a crash course in e-commerce, but it ended up being one of the best things to happen to Green Roost. We quickly learned how to engage with our community in a whole new way – through social media, email newsletters, and video content. What started as a scramble to stay afloat ended up opening new doors for us. We began to reach customers not just in our small town, but all across the country.

That pivot didn’t just help us survive the shutdown – it set the stage for long-term growth. Now, we have a thriving online presence that complements our in-store experience. Looking back, that difficult moment pushed us to innovate in ways we hadn’t before, and it’s made Green Roost stronger and more connected than ever.

Contact Info:

• Website: shopgreenroost.com or retailrituals.com
• Instagram: @greenroost or @retailrituals
• Facebook: https://www.facebook.com/greenroost
• Youtube: https://www.youtube.com/@greenroost

Image Credits

Jessica Stallings