Have you ever daydreamed of starting your own business? Most of us have. I know I have.

But all you do is daydream because you’re afraid you’re too young, or it’s too late, or you’re too busy with your family or you just have too many other things going on.

We can all make a long list of excuses about why we aren’t chasing our dreams and starting our own small business. But those excuses aren’t helping us.

Kelly’s story will motivate you to start taking action and start saying yes to opportunities.

Meet Kelly Gregory. She’s a mom to two boys, Jack and Jesse, a wife to a fellow business owner, David, and she also owns two businesses herself.

Kelly not only owns a popular local drive-thru coffee stand, Sip, but she’s also the fashionable owner of her own custom jacket business, Branded Belle.

We can all be inspired and have a lot to learn from this Oregon cowgirl who’s out here showing up for her family and her community, providing a supportive workplace for her employees, and saying yes to opportunities even when they scare her.

Read More: 49 Quotes to Inspire and Motivate You to Build Confidence

Originally from the country in Oregon, Kelly found herself attending George Fox University in Newberg, OR.

While studying at George Fox, Kelly became a barista for a local drive-thru coffee stand. A coffee stand that she would one day own.

She worked at Sip for over three years before moving out to St. Paul after graduation to help open another coffee shop in the small town.

She fell in love with the community and decided to stay in St. Paul but that didn’t stop her from hitting up the drive-thru of the coffee stand where she first got her start in Newberg.

One visit to Sip would catapult a new chapter in her life.

Randomly one day Kelly was driving through the coffee stand in Newberg and the owner happened to be working.

The owner plainly asked Kelly if she was ready to buy the business.

Kelly was only in her mid-twenties and a new mom to a 1-year-old baby boy.

She said yes anyways.

Two weeks later she was the owner of Sip.

“Now it’s going to be 15 years since I’ve owned it this upcoming fall,” Kelly explained with a smile. “It’s changed a lot since the beginning. It’s grown a lot and it’s been a really fun business.”

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Kelly has not only grown the coffee stand since taking the business over, but she’s also created a supportive work environment for her employees, several of whom have stayed with her for several years.

Kelly hires many young adults who attend the same university she once attended.

“One of my main goals was to create a place where my employees can grow. They’re not going to stay forever but they need a place to grow and a safe place. I’ve seen employees start really young, really inexperienced, really timid. And they leave very confident and just ready to explore. That’s what I want for Sip.”

But there have been a few employees who’ve decided to make Sip their home.

“There are some that stay and that’s amazing. But I never expect that. It’s really cool to see people grow there. I’ve actually even had several girls leave and then come back.”

Having dependable, amazing employees has been a huge help for Kelly. Being a mom, she can’t always be at Sip as often as she liked to be.

One of the struggles of owning Sip has been the transitional periods in her life like when her youngest son was born.

Being more limited on time with her youngest son, Kelly found it difficult to keep up on things happening at Sip. She sometimes felt discouraged since her coffee stand is a place she genuinely loves being.

Luckily, she has a manager and a great staff who keep Sip running day to day.

They’ve also helped her during the ups and downs of the business like when Covid hit in 2020.

As a drive-thru coffee stand, Sip was allowed to stay open, and the local community flocked to it.

“People really wanted to get out and there was nowhere to go.”

Long lines started to form during Covid, and even 5 years later the lines haven’t decreased.

Sip remains a treasured place in the Newberg community, even without Kelly heavily marketing it on social media.

One of the things she’s learned since owning Sip, is that social media wasn’t necessary for the coffee stand. The locals know about it and are going to come either way.

With only so many hours in the day, she let the social media for Sip go knowing it wasn’t vital to its success.

“You have to assess your business and ask yourself does this serve my business?”

While social media isn’t necessary for her first business, it is important for her second one.

Read More: Quick Easy Wins are a Simple Way to Boost Your Confidence to Help You Achieve Your Goals

Kelly’s creativity doesn’t stop at coffee drinks. She also started her own custom jacket business, Branded Belle, a few years.

Kelly never planned on opening this business, but when a friend asked her to make her a custom denim jacket with Pendleton wool, Kelly said yes.

This jacket was just the beginning. The possibilities of using Pendleton wool were endless.

A short time later, Kelly’s mom made custom Pendleton wool Christmas stockings for friends and their newborn baby.

This friend saw the potential in Kelly’s products. When she asked if she could share the stockings with her over 50,000 followers, Kelly said yes.

The orders started flooding in and Branded Belle was born. Her friend posted about the jackets in October and by Christmas Kelly and her mom had made over 300 jackets.

“That’s kind of when things started and it just went crazy from there. After I saw there was a want for it, my business mind started going. I was like ‘yeah let’s do this. This is so fun’.”

Kelly is the idea woman behind the brand and her mom is the seamstress.

Kelly’s mom has been sewing her whole life. So, when Kelly comes up with a new idea, like a reversible cape using denim and Pendleton Wool, her mom is the one to bring those dreams to life.

“She knows all the technical things. But then when she’s stuck on a pattern and I’m like ‘this could be fun’, she’ll be like ‘oh, I never saw it that way.’ So we work really well together.”

It’s been a few years since starting Branded Belle and Kelly has learned a lot in that time.

*If you want to gain more confidence to achieve your goals in just one week, subscribe to my newsletter to receive your FREE copy of the 7-Day Confidence Building Workbook*

For one thing she discovered she doesn’t like running a booth at large events.

She’s brought Branded Belle jackets to several large markets and rodeo events. But it’s difficult to run her booth while watching her husband participate in the rodeo and keeping an eye on her kids.

She hired other girls to run the booths for her, but she noticed the sales were significantly less when she wasn’t present.

“It’s to the point to where if I can’t run it, I don’t even do it. People want to know the business owner and see the face of the brand.”

Running a booth at large events is also a ton of work and they can take a toll on Kelly.

With customers still ordering from her website, and selling out at large events, having to restock all the jackets is a lot to manage.

It’s only Kelly and her mom sewing the jackets. Every human has their limitations on what they can get done in a day.

But she has discovered she loves running small events especially when it’s helping another business owner drum up attention for their business.

Earlier this year Kelly brought her jackets to a local Newberg salon where Kelly was the only vendor.

Kelly got to devote her full attention to the event.

“There wasn’t anything else going on. There wasn’t a rodeo. There weren’t kids. There weren’t other vendors. It was just so easy to focus.”

As much as Kelly loved the event, she was nervous about it.

Read More: 33 Journal Prompts to Increase Your Self-Confidence

“It was kind of a leap for me, confidence wise, because I’d never done an event on my own.”

When she ran a booth at big markets, rodeos, or pop-ups, the other vendors were also advertising and part of the pull for customers to flock in.

“For this, it was just me. So, I had to rethink how am I going to market this? I’m the only person marketing this where normally if you’re in a market with 50 vendors, the other 49 vendors are also marketing.

You know there’s always that feeling, what if no one comes?”

Even with this doubt in the back of her mind, Kelly knew her customers needed this event.

“I didn’t want people to miss it because I knew there was a need for people to try on jackets.”

Kelly bombarded her socials, posting twice a day about the event, hoping none of her customers would miss the opportunity to try on a jacket in person.

The event was a huge success, and the salon was packed with customers!

“I was definitely nervous that no one would come, or I’d forget something. But I had a couple of really good friends help me out. I definitely needed them.”

This event was a completely new experience for Kelly, but she’s grateful she agreed to do it.

“I am a really, I call it mind work, type of person. I like taking on challenges that scare me. I’m not gonna lie that they don’t scare me. But I feel like it gets you closer to the most confident and brave person you can be.”

Kelly passes this message along to her oldest son and her employees at Sip as well.

“I try to tell this to my girls at Sip, because I just think there are so many people held back by all the what-ifs like what are people gonna think. The more that you think those things, the more your insecurity grows. With every little thing that you accomplish and conquer, it just gets you stronger. You have to get past your own thinking.”

This type of thinking has been one the keys to Kelly’s success in both of her businesses.

*If you want to gain more confidence to achieve your goals in just one week, subscribe to my newsletter to receive your FREE copy of the 7-Day Confidence Building Workbook*

Sip and Branded Belle are two completely different businesses, but Kelly has hopes to bring them together more in the future.

She’s already adjusted Sip’s branding to make it more inline with Branded Belle.

Some of her coffee customers don’t know she also does custom jackets and some of her jacket customers aren’t aware that she also owns a coffee stand.

Kelly is only the common denominator in both of her businesses.

By branding herself on social media, she’s able to advertise both businesses and not stress about creating separate content for Sip since it’s not as important to Sip’s success. 

She also hopes to one day open a brick-and-mortar location where she can showcase both businesses.  But her 2 businesses need the right place to call home.

“I’m not in a rush because I want to have a good spot. It’s worth it.”

In the meantime, Kelly is taking steps to bring her 2 businesses closer together and make them more compatible.

When she first bought Sip, she had no idea she’d own day years later start a custom jacket business.

Kelly was only in her mid-20’s when she bought Sip and she was in her 30’s when she started Branded Belle.

“My first business I was very young and very gung ho. But when I started my second one, I was more apprehensive. I think that’s what really grew my confidence and my business skills.

I almost didn’t do it, because I felt like there were a lot of younger people that are coming up with a lot of ideas. How am I going to be able to do this? I’m older, I have kids, I have a lot going on. But it’s just proven me wrong.”

Kelly won an award a couple years ago from Western Life & Style for their 30 over 30 which celebrates women in the western business industry. In 2024 there were over 500 nominations nationwide.

Out of the 500 nominations only 30 were selected and one of those was Kelly!

“I was really surprised at that. It was huge, and very humbling and sweet award that I got. And that just kind of sealed the deal like you’re still able to make moves when you’re older. You’re never too old to start.”

1. Always say yes to new opportunities. Kelly said yes in her mid-20’s to buying her coffee stand, Sip. Kelly said yes when her friend asked if she could post the Pendleton stockings. Kelly said yes to hosting an event where she was the only vendor.

2. Don’t Give Up Even When Things are Difficult. After 15 years of owning Sip Kelly has had a few transitional periods that made having her business more of a struggle. But she never gave up on it or herself. 

3. Even if you’re scared, take on the new challenge. Kelly never let her fear stop her. She was nervous about being the only vendor at an event, but it was a huge success!

4. You’re never too young to start making big moves. Right after graduating college Kelly helped open a coffee shop in St. Paul. While only being in her mid-20’s she became a business owner.

5. Invest in your team. Kelly not only works with her mom in Branded Belle, but she also has great friends and a great crew at Sip who appreciate her as much as she appreciates them.

6. Know when to say no. Kelly realized that social media wasn’t crucial for Sip to succeed so she was okay with setting that down. She also discovered that she doesn’t love running booths at large events, so she’s scaled back on how many she does in a year. You don’t have to do everything. Learn what works for you and what doesn’t.

7. Don’t be in a rush. While Kelly hopes to one day have a brick-and-mortar where she can combine both businesses, she’s not rushing into it. She’s taking her time to find the perfect location that will work for not only her, but also her customers.

8. You’re never too old. Kelly was more apprehensive about starting her second business because of her age. However, that business is the one that has grown her confidence the most, proving it’s never too late to start something new.

Let me know in the comments if Kelly’s story resonated with you! Also make sure you check out her website and order your own bag of coffee beans or an amazing new jacket. I don’t own a Branded Belle jacket yet, but I have tried Sip coffee and it’s delicious! I drank one (okay, two) cups of it while writing this post.

Keep chasing your dreams no matter your age or insecurities. Let Kelly’s story inspire and motivate you to start your own business or chase whatever beautiful dream you have!

If you want to read more inspiring stories on women who have found their direction in life and are pursuing their dreams, check out Katie’s story on starting a blog and moving to a new country!