Founder to Founder: Kailee Steward from I'm With The Band Headbands

I met Kailee back in 2018 when we shared a co-working space called Biz Babes. It was a space where female entrepreneurs could come to work on their businesses but not feel alone. Kailee & I seemed to share the same work schedule, so it was a matter of time before we became friends & started working alongside each other. 

I often would find her in our shipping room, packing dozens and dozens of headbands, turbans & scrunchies to mail out each day.  I remember always seeing rows and rows of multicolored piles of dusty pink, red, greens, whites, mustard purple, black & blues in various velvets, silks, cottons & satins. 

Kailee has built an incredibly successful business around her passion for music. Each accessory in her collection is named after a name of a song. I'm With The Band's stockists include Free People, Pigment, Dazey LA just among the few names that carry her gorgeous line.

Kailee's work ethic, passion & drive is truly admirable. She is humble, has a wicked sense of humor & is a joy to work with. A true inspiration - here is her story.


Kailee Steward 

Brand: I'm With The Band 
Instagram: @imwiththeband
Product: headbands, scarves, scrunchies, hair ties

1. How did you come up with the idea for your business?

I started with the idea to create a rad, rock n roll style women’s workout line to fill a gap in the marketplace. I had never started my own business and thought it was better to learn on a smaller scale rather than a full fledged apparel line. Headbands kept popping into my world… I’ve used them everyday for most of my life from washing my face to working out. So I started with a simple headband and gradually added styles to the line and it’s expanded itself organically. I really wanted to become an expert in one thing before moving onto the next and I'm definitely still working on that!

2. "Im with the band" is such an awesome name - is there a story behind it?

Aww, thank you! Music is truly my first love. Since so much of the line is musically inspired and the pieces are named after my favorite icons and muses, it just made sense. I’m With The Band was born.

3. How long have you had this business? What were you doing before IWTB?

I started IWTB in 2013 which seems like a small eternity ago! I was designing shoes before I started the company.

4. What lights you up about your business?

Getting to connect with my customers. The ability to create and express myself through this medium and most of all, hearing that my products have helped someone or are brightening someone's life in any way, shape or form.

5. What task(s) do you absolutely hate doing in your business?

Anything to do with organizing / creating systems or dealing with numbers - none of those things come naturally, unfortunately!

6. What does your morning routine look like?

I wake up, meditate, make coffee, press go and hope for the best!

7. Are you a morning bird or night owl? When do your creative juices kick in? 

Naturally, I’m more of a night owl. I feel more creative at night time but over the years have trained myself to become more of a morning person. Quite honestly, I need to be both to get it all done.

8. How do you unwind?

That’s a great question, haha! I love to take walks to get my body moving and the energy of the day out. I try to start the day with as clear a head as possible by meditating first thing. Also taking time away from my phone when possible. A glass of wine or a cocktail or two doesn’t hurt either.

9. If you could do a photoshoot with IWTB anywhere in the world, where would it be & why?

Probably Italy since it’s my favorite place on earth (so far anyway). It’d be fun to explore creating a photoshoot there and going super Italian style!

10. What advice would you give to other young women starting businesses? What are some things you would've liked to have known before stating your business?

Stay in your lane, put your blinders on whenever possible. Do what you love and that inspires you. It’s not easy and you need to pull deep from within to keep going when your chips are down. Having a North Star so to speak helps to keep you focused and moving forward. Keep going even when it's hard. Honestly, I think learning as you go is best. If you knew all the challenges that lie ahead of you, I don’t know that any of us would ever start anything new. Stay in the moment and try to appreciate the journey.


Leave a comment

All comments are moderated before being published