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Marketing Advice Q&A: Caroline Sipiera

Caroline Sipiera is someone with a passion for vintage charm. More than that, she's one of our youngest featured entrepreneurs, defying stereotypes and following her dreams on a regular basis.

Meet Caroline.

Growing up in Galena, Illinois she always loved the bed & breakfasts and local shops that peppered the rolling hills of the historic town. Even as a little girl, she was fascinated by the history behind the architecture, design, and the people who built the quaint, Americana town.

After graduating college with a degree in communications, Caroline simultaneously worked a marketing and advertising job in Davenport, Iowa, started her own event planning business, and restored an 1891 home overlooking the Mississippi River. Her dream to convert the home into a bed & breakfast was challenged logistically by the older construction and yet, she pushed ahead thinking of new ways to accomplish her goal. In 2021, a historical bed & breakfast overlooking Galena’s Main Street went up for sale and Caroline quickly saw the window of opportunity to return to her hometown and make her dreams come true. Caroline renamed the estate to Miss Murphy’s (a nod to her childhood pretend B&B!) and has been delighting guests all summer long.

Q: What advice would you give to someone starting a new business?

A: My advice to anyone starting a new business is to commit and just do it. I feel like those of us with entrepreneurial spirits have our dream businesses we want to pursue in a “perfect scenario” but the truth is that you can always find reasons not to do it, so you might as well seize the opportunity and try. I think 50% of owning a business is having the courage to make the leap. Once you get the ball rolling, it is easy(ish) to keep going.

It is finding the strength to leave your job, to try something new, to tell your friends and family, to apply for that loan… that's the hardest part. If you have a passion and a business plan, rip off the band-aid and just do it!

On the marketing front, hire help! This is not the business area to “wing it.” Good marketing will likely define the success of your business. Education is invaluable. Even if it is just a one-time consultation because your budget is on the smaller side, book that session, learn, and grow!

Q: What's one thing about marketing your business that you wish you discovered sooner?

A: Define who your audience is before anything else. The first time I advertised was with an ad targeting the Chicago suburbs. I didn’t think too much about customer personas for my bed & breakfast, I just wanted to target the biggest area possible. The ad got a huge reach, but ultimately, no bookings from it.

After I evaluated what happened, it made sense. Targeting that broad of a market wasn’t going to get the results I wanted. Once I defined who my customer was and started targeting that individual, I started getting several paid bookings and over 30 clicks per ad.

Q: What are your thoughts on the back-and-forth changes with Instagram? Do you plan to adjust your content strategy to keep up with the increase in video/Reels?

A: Honestly, I think Instagram has gotten a little out of hand trying so hard to be TikTok. They should focus on the qualities that people like about Instagram and not try to be something else. One lesson I’ve learned about social media is that personal accounts will always perform better than business accounts.

For example, my personal accounts that feature content about my lifestyle and passions for fashion and modeling have more than 22,000 followers across platforms. My business account @miss.murphys has 460 followers. At the end of the day, people trust people and will naturally be drawn to personal stories, so try to infuse those into your business wherever it makes sense.

One last thing is to be open to trial and error. My historic bed and breakfast has been open since May and I’m using the first year to try different strategies, channels and formats to see what works best for my new business. As a plug I know she didn’t want me to include, I did a private working session with Andrea at @fifteenmarketing and learned so much. She helped me think about my marketing strategy before I started pushing content through my channels and it was a game-changer to have that kind of expert sounding board. I plan to schedule another session in Q4 to brainstorm with her as an official business partner to figure out my marketing plan going into 2023.

Thank you.

A special thanks to Caroline for her time and advice, and if you're looking for a Midwest vacation full of vintage charm and modern amenities, please make sure you visit Miss Murphy's. Her bed & breakfast and the Galena area are a Midwest gem!





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