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Pushing The Boundaries Of Personal Change And Growth ‒ Interview With Terresa Zimmerman

As the only female founder of a men's underwear brand, Terresa’s life is a pun-fest. She loves Main Street, has an award-winning book called, Oh, Lords: Life Lessons in Dating Stories, and is the co-founder of innovative, personal development app for businesses, Sayhii. Her and her husband David are bossed around by 2 Aussies, Whizkey & Tequila.

Terresa Zimmerman, Founder of Wood Underwear


As the Only Female Founder of a Men's Underwear Brand, Multi-award Award Winning Author, and Tech Entrepreneur, Terresa Zimmerman, is Pushing the Boundaries of Personal Change and Growth


Being the only female founder in the men’s industry takes some serious balls, just ask Terresa Zimmerman, founder of Wood Underwear, currently celebrating their 10-year anniversary but it doesn’t stop there. Last year, Terresa co-founded an enterprise software company, Sayhii, with an amazing partner who blessed her with the involvement. Sayhii is going to change the world of employee engagement by flipping things on its head and truly making it about the individual employee.


And if that wasn’t something to get Terresa on your radar, her book, Oh, Lords! that she co-authored with Jes Averhart, has won 3 significant awards in its first year of publication and is still going strong.


Today, Terresa, an entrepreneur, author and athlete, challenge seeker, mom of two Australian Shepherds that keep her in line, wife of a deeply supportive man and supporter of all who wish to explore their dreams is helping and encouraging others to push their own boundaries.


“I find that revealing my own mistakes, defining them and studying what there is to learn, is both constructive for me personally and also helpful for others who may not now have to go down that same path.”


What kind of audience do you target your business towards?


For Wood Underwear, our customers are men who care about what they wear and how they feel in it. That might mean they just got curious about our product and didn’t even know they could care about how their underwear made them feel…until they tried it. Underwear is the foundation of a great or even just more functional wardrobe. It matters and it makes the investment you’ve put into everything else in your closet pay off in an elevated way. And, it shows itself in the confidence you feel.


With say hii, we are pushing the boundaries by providing self-improvement at scale to every employee at an enterprise. Something they can take with them that is about them. The payback to the company is absolute, but the growth is with the individual.


With Oh, Lords!, our lessons are all about having agency over all the relationships in your life. We color the lessons with our very own dating stories and personal experiences. The throughline, with all of these aspects of my life, is about self-growth, self-confidence, and owning your own development, the responsibility for it and accountability to it.


What is your work inspired by?


I’m driven by the interest to always be learning something. It means a lot of trial and error, but I’m okay with that in order to push my own boundaries. I’ve naturally done that my whole life but it’s more and more intentional as I age and grow. When I started Wood Underwear, I quickly realized a love for ‘main street’, the small businesses that make up the core of our neighborhoods and communities. And at the heart of those businesses is relationships. Coming from a corporate background, it was a stark realization. So whatever I do, I try to support the main street, from focusing Wood Underwear sales through small businesses and specialty stores, to promoting Oh, Lords! through independent bookstores. Did you know there is an online place to buy from local bookstores? I didn’t but now it’s my new favorite go-to: indiebound.org. The pandemic shutdown pushed everyone to go online somehow, so there is every reason now to seek out small businesses as your online shopping go-to. Take the extra minute and find them online. Support local.


What are your current goals for your business?


My goal is always financial growth generally. Then I try to set specific goals around that – new categories to increase sales in, new markets to open, all the way down to being as specific as a plan to grow an individual account. Specifically, next year we are looking at a new market to grow into. We have products for it and just haven’t yet positioned them for the market. We’re doing some seeding right now and hope to make a bigger push next year. I find that breaking goals down to really targeted and bite-sized specifics makes getting there much more attainable and helps to bring everyone on board in the same direction.


What would you like to achieve for yourself and your business in the future?


I would love for Wood Underwear to be THE wardrobing brand in basics. Meaning, I’d love for us to be known as the men's underwear company that transformed the way men think about underwear (a commodity) to being a fundamental item in the wardrobe mix.


For Sayhii, I know that it will transform the way the world thinks about engagement –instead of a top-down approach, it will truly be grassroots led. Employees will let companies know how they wish to engage and companies will be more productive and healthy for it.


Tell us about a pivotal moment in your life that brought you to where you are today.


I’ve had many pivots in my life, little ones all over the place and a few fairly big ones. The biggest pivot, with the benefit of hindsight, was in my personal life and that affected everything. The beginning of 2006, I hired a dating agent. I had decided at the end of 2005 that if I wanted a life partner I could not keep doing the same things I was doing and expect a different result. Within a few months, I met the man I fairly quickly married. He is not only incredibly supportive, even when I come up with something a bit crazy, but he actively pushes me to do and be more.


Follow Terresa on Instagram, LinkedIn for more info!

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