Featured Solopreneur: Don't Tell Summer "Hats With a Purpose"

Originally from Oregon, Solopreneur Olivia O’ Connor, never imagined that she’d end up in Australia, starting her own hat company “Don’t Tell Summer,” at the ripe age of 22!

Although being a young entrepreneur isn’t always easy, Olivia is fueled by a greater desire to inspire young people, encourage them to take risks, and help them go after their dreams!


Read on as Olivia explains how she transformed a blog into a brand, the steps it took to create a cause-driven product line, and her best advice for conquering fear and self-doubt!

 >>|| Don't Tell Summer Instagram || >>  << || Don't Tell Summer Website || << 

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What sparked the idea for Don’t Tell Summer?

During my junior year of college, I studied abroad in Australia and had the time of my life. I kept going back and forth between California and Australia during the American summer and even though it was technically “winter” in Sydney, they were some of the best ‘summers’ of my life. I was making friends, being myself and having tons of fun along the way.

When I went back to California for my senior year of college, I felt different. I felt like anything was possible. I was craving a career path that would allow me to do what I loved (regardless of school obligations, or internships, I believe that we should all be able to have fun doing what excites us!).

Pairing that attitude with the right lifestyle—including meeting a group of Aussie surfers who ran their own surf blogs—led to the creation of the DTS brand.

What makes your company one-of-a kind?

The hats are different. They aren’t just a piece of fashion or another accessory; anyone that wears them knows that they have their own vibe— a positive, fun-loving vibe. In addition, a portion of every purchase goes back to a young person with a big dream!

The DTS brand is meant to inspire young people to do what they would love to do now, rather than “waiting out” for some point in the future. This can be anything from going after a big dream, to saying “yes,” to new opportunities, pursuing passions of the heart, or chasing things that completely excite you!

When I first had the idea of creating a “dream fund,” it was something that I knew I wanted to have as a part of the DTS brand. As a young person just starting out, I was told that I shouldn’t just give money away, and that I should find a way to write it off on taxes or loan the money. But after doing all of my research, it seemed like the best idea was to freely give away a portion of sales to deserving, inspired, rad young individuals. 

How do you define “success?” What has that looked like or felt like in your career?

Success is making an impact on others’ lives, as well as my own. When I’m having fun, feeling creative and excited about where I am and where DTS is going—I feel successful.

What drives you to get out of bed every day and continue what you’re doing?

Remembering why I love it in the first place. I love being creative and DTS is the perfect outlet for this.

When I feel like I’m plateauing or that the creative energy isn’t flowing the way it should be, I re-motivate myself by focusing on a young person pursuing their dream.

Tell us what it’s like living and doing business in Australia—compared to the U.S.?

Technically, DTS is still an American brand, and since you can easily sell products online and be located from anywhere— I’ve found that business transactions are pretty similar.

Lifestyle-wise:  it’s very laid back and fun. There is a massive amount of bloggers here, which allows me to connect and collaborate with people in person—which is great! Of course there are many rad people and brands in America that I would love to collaborate with, but I’ll just have to wait for my next visit!

All in all, I think that living in a different country motivated me to pursue my dreams and gave me the confidence to build DTS. When you make such a big move—you’re cut off from what you’ve known your whole life, and you are opened up to new creative possibilities!

What did you study in school? Has it helped you with your business in any way?

I studied Psychology and was always interested in Positive Psychology. In one of my classes, one of the professors had us write about our self constantly. She created an environment where you wouldn’t feel judged for sharing your truth. I think that is where I formed my original “tone” for DTS.

How did you learn about manufacturing? What were the first steps you had to take to get the hats produced?

My mom has been in merchandising my whole life, so I definitely leaned on her to teach me the ropes.

To start, I had to do a lot of research on companies both in Australia and America as well as do research on the structure of the hat, the labels, the textures, the colors and the design.

I went back and forth with a few companies and was about to use one in Australia but then communication was delayed, and I was forced to start over. Finally, I began speaking with a company that I’d found in Oregon (where I’m originally from), and it just felt like it was meant to be!

The last step was designing the hats. I brought out my mom’s paint-color swatches and started mixing and matching colors that I thought went well together—finding lots of inspiration to help me create each color scheme. The next step after that would have been to order a sample of my designs (my manufacturer is thousands of miles away so I had know idea whether or not I’d get what I wanted!) – but I had a feeling it would all work out and I ended up ordering my first hats in bulk.

Thankfully, the first batch turned out just right!

What would you have told an earlier YOU, when you were first starting out?

Things will take time. Go after what you want—but you don’t need to revolve your world around it.

You can make money doing something else, but make sure you’re happy doing it, because it’s important to have good energy around you!

Make as many fulfilling friendships as you can.

Dream as big as possible. Only YOU can set your own limits. Grab a mentor that’s in the place you want to be, and grow a community around your idea, even if you’re not fully ready and don’t have a finished product.

Who have you turned to for mentorship/guidance throughout your career?

The best thing I did was get a coach. I worked with Debbie Spellman here in Australia, who was monumental in turning DTS from a tumblr into a blog and then into a hat brand.

Sometimes when it’s just you working on your brand it can be hard to step back and think, “OK, where can this actually go? What’s really possible?” Having a coach helped me to be accountable and to go for things that I might not have thought possible. I’ve also taken the “Bright-Eyed & Blog Hearted” course with Rachel from “In Spaces Between.” This was a great system for creating all of the pages on your website and growing a community of other bloggers. It’s nice to be able to turn to other gals to collaborate and bounce ideas off of one another.

How do you handle fear and self-doubt?

I experience fear a lot. Like alotttt.

Talking about my fears with others helps to put them into perspective. If you let fear or self-doubt hang around for too long, it can be hard to quiet it, which is why I like to act on dreams quickly.

 When creating the hats, there wasn’t a lot of time between having the idea, designing the product, and having them manufactured. I knew that if I sat with the idea for too long, I might never create them, and so I had to go after it quickly.

When you’re filling your mind with creativity and things you’re passion about, there’s less room for fear and self-doubt to creep in and take over.

When you’re feeling overworked or frustrated, what techniques do you use to handle your stress?

I go out. I get out of my head and spend time with friends. Being with other people allows me to just BE. If something deeper is on my mind, I will journal, but I’ve found that the energy shifts when you get out of your own head and go have fun!

Tell us about one or more business decisions you’ve made that you are proud of, and have contributed to your success in some way?

Deciding to invest in my brand.

A lot of the money that I earned (in a side job) last year went into growing and creating products for DTS. My parents ended up moving to Sydney, and I decided that after years of living on my own, I would move in with them so that I could continue to grow DTS without the pressure of paying rent.

I’m also proud that I decided to just go after my idea to create a hat line. Once I had the idea, I started designing them two weeks later. This could have easily been one of those times where fear crept in to say, “you have no idea how to design hats, why would anyone buy them? Could this even work?’ Luckily, I didn’t allow the space or time for that sort of negativity to come in, and I just went with my heart.

What are some of the challenges that you face in your business?

It can be hard when you know where you want to be, but you aren’t there yet.

It’s important to enjoy yourself and have fun with where you’re at, knowing that you will get there in time.

If you had 24 extra hours in your week, what would you do with it (personal or professional)?

I would travel more! I would take a trip up the coast or go overseas for a short trip. I think traveling and experiencing new things is a great way to gain more perspective about what you would love to do and to get your creative juices flowing!

What is your vision for your business? Where do you want it to go?

I want to continue to grow a community of young people supporting young people through story telling, mentorship, collaboration and events. I also want to financially contribute to young people’s dreams, and inspire more to follow theirs as well.

In the spirit of our #sheforshe campaign, which women have supported or inspired you the most throughout your career?

My mom—she’s quite the go-getter. I’d also say any of the young women my age who are also going for their dreams.

My friends have also been super supportive.

What would your advice be for young women looking to launch a new venture of their own? 

You have to start somewhere.

Don’t wait for all the pieces to fall into place, or for that time when you think you have enough time or believe you are an expert enough to put what you love out there.

Even if your product isn’t ready, whether it’s clothing, a book, a blog, a workshop—you name it—you can always be building your community. People will connect with your vision and ideas before you have the product ready, so it’s best to set up your blog and social media right away.

If you feel like you’re just getting in your own way, then I suggest you hire a coach. This was extremely important for me going after things that I thought might not be possible, and knowing which directions to move in. 

What advice would you give to young women who worry about their future—or are unsure which career path to choose? 

If you have a dream sitting in your heart, don’t give up.

If you’re unsure which path to take, always choose something that will put you in a happy, creative space. It will be easier to figure out what you want to do from a place of content—rather than a place of havoc.


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