Meet the Mentor: Kaitlin Holland

This is part of an ongoing Maker Mentors guest blog series that features interviews with established makers.  Join the updates or recommend a maker for the blog.

What does your business do? The School of Styling is geared towards equipping and encouraging creative business women to style with intention, build smart businesses, and cultivate life-giving community.  We host three day hands-on workshops as well as create online class content.

When did you start your business? I launched the school of styling in May of 2014 and hosted my first workshop in August of 2014.

What kind of work were you doing before you started your business? Prior to starting The School of Styling I owned a local vintage rental company and did freelance styling for magazines, workshops, and weddings.  The more I got to know fellow creatives, the more I saw a need for a community where women could really dive into their businesses, perfect their craft, try new things, and develop lasting relationships.  Which is how The School of Styling was born!


What was the biggest challenge in getting started? The biggest challenge for me was communicating my idea with the world!  What I was doing was so new at the time, it was hard for some people to wrap their heads around the various elements of the workshop.  I knew how amazing it would be, I just had to convince everyone else!  I’m endlessly grateful for the seventeen ladies who attended my very first event.  If they hadn’t taken a leap of faith who knows where I would be!

What product are you most proud of? I’m most proud of my workshops.  I love developing online content, but the workshops are my bread and butter.  I get to engage in real conversations with ladies from all over the world and teach things I’m passionate about!


How did you find your first few customers? Great question!  I had a bit of a following on Instagram at the time, and I quickly gained traction the first few months.  I believe most of my initial sales came from that.

What marketing tactics have been most successful for you? Instagram has been a game changer for my business.  Being a visual company, this platform makes most sense for both who I’m trying to engage with and what I love to do.  I’ve had quick growth on Instagram and from there I attempt to push as many people as possible to my email list.  In my mind, my email list is my target audience.  They have bought into my message, are excited about my offerings, and will be most likely to purchase in the future.

Who are three creatives that inspire you? Gosh, there are so many but I would have to say I’m currently inspired by Emily Ley, Jess Connolly, and Jeni Maus.  Emily Ley, of The Simplified Planner, is a serious boss mama with two new twins and a pre-schooler.  Any business owner who can balance work and family with such grace and intention inspires me!  Jess Connolly is such a beautiful voice for our generation of creatives.  I love her business tips and tricks and I constantly look at her feed for inspiration.  Jeni Maus owns Found Vintage Rentals and is a pioneer in the vintage rental world.  I have so much respect for creatives who pave a new path and end up educating the world as they figure it out!

What does a typical day look like for you?  I like to get into the office at least 30 minutes before my assistant arrives, which is around 9:00.  I try to limit my emailing to about two hours a day, but depending on the time of year I could end up spending most of my day on email.  I like to mix in at least one hour of design / planning work, depending on what projects are coming up.  If it’s a day I’m sourcing materials I could spend half the day running errands looking for specific products.  I try to knock out a bunch of Instagram content one day a week so I’m not spending a lot of time on it everyday.  Basically, depending on the time of year, everyday looks different but involves some level of planning, designing, emails, and a lot of coffee!

What is one thing you wish you knew before you started your business? There will always be work to get done!  For the first three years of business (both my previous company and current one), I would work way too much.  I felt like I had to knock out my whole to do list in one day or I had completely failed.  I have since realized that I work better when I’m exercising spending time with my husband and friends, prepping meals, and doing a few things each week that I love (other than work).  Work is amazing and wonderful, but I don’t want it to be my life.  I had to draw the line and I’m so thankful I did.

You can follow Kaitlin’s work here: Website // Instagram //  Facebook

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