We recently connected with Ashlee Sullivan and have shared our conversation below.

Ashlee, appreciate you joining us today. What’s the backstory behind how you came up with the idea for your business?

When I started my company, “Woman + Warrior” back in 2019, I couldn’t have even fathomed what it would grow to become. At its conception, it was simply going to be a custom silk screen printing company; an avenue to leave classroom teaching and help our family build a debt-free life. However, as my life dramatically changed…the brand evolved with me.

During the summer of 2020, my husband commissioned with the US Army; our already established family of 6 began our wildest adventure yet. In 2021 alone, we would live in 4 different states, move or “PCS” (Permanent Change of Station) 3 times, and navigate a 9 month long deployment…that we were launched into only 3 weeks after landing at our final duty station.

This time away from generating revenue, this time of “forced rest”, became the most critical season of my entrepreneurial journey. Within a year’s time, I had been thrown into a brand new life and I had become a brand new me. I experienced some of my highest highs and some of my lowest lows after becoming a Military Wife. I felt loneliness, isolation, and deep despair. And yet, I experienced so much indescribable joy. Through my husband’s service to our country, I have had the privilege of crossing paths and connecting with the strongest, most sacrificial people I have ever met. I couldn’t have possibly known what Woman + Warrior would become, because I hadn’t met the main characters of the brand’s story yet…

The Woman + Warrior is every Military Spouse I have ever met. After I understood this, that THIS was who Woman + Warrior was always destined to represent, THEN I was able to get to work. My passion for serving and connecting those in the Military Community runs deep. Whether that be through providing comfort with apparel, providing resources, or connecting the unconnected through our online community, Woman + Warrior is a brand unifying the Military Family.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I am a proud Army Spouse and have been blessed to be married to my best friend for almost 14 years. I’m a mom of 4, and a former educator and PhD drop-out turned CEO and Founder of Woman + Warrior –an apparel brand line and community for the Military Family. I like to say that I’m an “accidental entrepreneur”, but the truth is…I’ve been accidentally preparing for this career path my whole life.

I was born to be an artist. I began selling my original art door to door when I was just a child. It wasn’t very lucrative…my mom made me return all my revenue to my neighbors. I wear my adolescent ADHD diagnosis like a badge of honor; I have a racecar brain, I’m a dreamer and a visionary, and I possess a drive to succeed in whatever excites me. When I went to college, I wanted to be a graphic designer. Naturally, I changed my major a million times until I landed on what felt safe: classroom teaching. Never in my life did I think I would be more passionate about anything else; I had a natural talent for the art and craft of teaching and pursued a PhD in Curriculum & Instruction.

And then…it came to me like a whisper.
I just knew I was on the wrong path.

I had a deep desire to create and educate beyond the four walls of a classroom or a university. And I also had a deep desire to dig our family out of 6-figures of student loan debt.
I declined my Graduate Assistantship and dropped out of my PhD program.

I decided on a whim, that while I may not know a thing about entrepreneurship and didn’t do so hot in math class, that I was going to start a business.
Why so bold?
No idea.
But I decided I was brave enough to risk my own significance, talented enough to make things people would want to buy, for more than it cost me to make, and driven enough to figure out the rest.

I truly built the plane while flying it.

I am a self-taught: graphic designer, silk screen printer, web designer, branding expert, social media marketer, SEO nerd, fashion trend analyst…you catch my drift? For now, I wear all the hats at Woman + Warrior.

In May of 2023, Woman + Warrior went under a complete and highly successful rebrand. I saw a gap in the market for on-trend, timeless, high-quality apparel for the military community. I was personally sick of running to the Exchange (a military installation’s sort of “mini-mall”) and coming up empty handed for items for myself or my kids. And I was really over settling for the tasteless, mass produced items marketed to military families on Amazon. We shouldn’t have to “embrace the suck” for EVERYTHING. The Military Family deserves to be SEEN, look GOOD, and feel GREAT while doing this crazy thing called Military Life. And that’s where Woman + Warrior fills the gap. Our apparel is designed and produced BY a Milspouse, FOR the Milspouse and their family.

If you’ve been in business long enough, it’s no secret that “re-branding” is no easy feat. But the military family is a community like no other. The support from all branches of service was fast and the demand was furious. The Woman + Warrior Community is the most loyal and supportive one of its kind.

How did you build your audience on social media?

I built my audience organically by simply: consistently showing up and by sharing both my heart and my life. I believe there’s great power in transparency and authenticity. If you can have the courage to be yourself, the growth will come. You’ll attract and repel the correct and ideal audience. It’s never a waste of time to build genuine connections with your community supporters and customers.

Are there any books, videos, essays or other resources that have significantly impacted your management and entrepreneurial thinking and philosophy?

My best advice I give to anyone who will listen, is to not only read, but READ WIDELY. Some of the best mentors I’ve ever had in my life I’ve found in books. Read across disciplines. Don’t just pick up your everyday business books, pick up books on things like rocket science, setting boundaries, read literature from great philosophers or musings from hall of fame coaches. There is something the be gleaned from all of it and applied on your journey as an entrepreneur. Readers are leaders and as an entrepreneur, you must not only lead yourself, but lead yourself well. You can’t go wrong spending time diving into books by Ryan Holiday, John C. Maxwell, or Donald Miller.

Also, PAY ATTENTION. We live in a digital and FREE information is everywhere as long as you PAY ATTENTION. Watch your peers, watch and listen to those voices, those thought leaders within your industry. My absolute favorite podcast is Jenna Kutcher’s Goal Digger Podcast. It’s been the best investment of my time and professional development as an entrepreneur…and it’s FREE ninety-nine.

Contact Info:

• Website: https://www.womanandwarrior.com/
• Instagram: Instagram.com/thewomanandwarrior
• Linkedin: https://www.linkedin.com/in/ashlee-sullivan-3b0585278