Being Vulnerable With Caryn Sullivan of Pretty Wellness

Being Vulnerable With Caryn Sullivan of Pretty Wellness

Last Updated on September 8, 2021

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About Caryn Sullivan

I’m an author, entrepreneur and 2x breast cancer survivor thriving with stage IV disease. Prior, I spent 20 years in corporate America in marketing, PR and business development roles in the sports/entertainment/media industries. I was a workaholic, junk-food junkie, and weekend fitness warrior. While I always wished on pennies (believed in the importance of positivity and dreaming big,) I was also a huge worrier. After my stage IV cancer diagnosis, I didn’t know if I was going to live four months or four decades, so I took my did what I did best – became a student of “the business” aka my cancer life. I researched who was thriving with cancer and chronic illnesses and what they were doing to be well. I became passionate about it, changed my lifestyle after this and was determined to inspire other women to do the same. I sought certifications, started writing about my journey and found Pretty Wellness.

About Pretty Wellness

I found Pretty Wellness, a healthy lifestyle media company, after my stage IV cancer diagnosis seven years ago. As my body was going through intense stress and treatments due to the cancer, I noticed that making wholesome lifestyle changes resulted in more energy, a clear mind and less anxiety. I thought about my lifestyle in corporate and how the grind made me stressed, sluggish and seeking more. So, I started Pretty Wellness to inspire other busy women to take small steps to take care of themselves. Within the past seven years, I’ve shared the messages, tips and formula to millions of people in-person and virtual events as well as serving as a media correspondent. Having a media / marketing background – how I started the company was by creating the brand with the intention to evolve into a media company. While I wrote, presented and served as a media spokesperson in my corporate career, as an entrepreneur, I started writing for both my own platform,, as well as others (Huffington Post/Huff Post, Thrive Global, Healthy Moms Magazine, WTNH-TV and more) in an effort to hone my craft as a solopreneur The goal was to build a boutique media company focused on inspiring people, specifically busy women, to take small steps toward better health and happiness and Pretty Wellness can (does) help them get there. Through the past seven years, I’ve created a platform of inspirational and informational programs that I present as keynote speeches or webinars throughout the country with thousands in the audience. I’ve authored a book, “Happiness through Hardship” (which serves as a fundraiser for metastatic breast cancer) and has been recommended by lead oncologists as a book to gift to patients upon their initial diagnosis. I’ve also evolved the sub brand, “Happiness through Hardship” to expand beyond cancer – to support and motivate anyone going through hardship.


How Did You Get Your First Several Customers Or Users? How Many Users Or Customers Do You Have Now?

As a motivational speaker – I started doing presentations for free or trade to get the experience and gain credibility locally and through old colleagues. I did about six a year the first two years with small audiences ranging from 20-75. Now, I do 12-30 events a year (the pandemic has shifted these to more virtual events), where I speak to groups ranging from 50 – 1000 at each event. From a media standpoint, each platform has grown tremendously especially the podcast. I’m now working on taking a segment within the podcast and monetizing it.

How Does Your Company Grow And Acquire New Customers?

The company grows by adding new platforms and advancing efforts on the ones we already have: The Book – The book brought in sales as well as a fundraiser. For every book sold, half of the net profits are donated to “The Cancer Couch Foundation.” The book’s main goal is to help others and I’ve found that new clients for speaking events or podcast followers can come from book sales. The Podcast – The podcast continues to be a lead generator for both those I interview as well as for our speaking/program events and the book. Big Sky Dreams – We’re working on what is next – in the media landscape things grow and change and we want to grow with it in an effort to inspire and educate more people on the importance of their social, emotional, mental and physical well-being. We’re working on what “Happiness through Hardship” could look like as a TV / streaming show.

What Actionable Tips And Tricks Do You Have For New Founders Who Are Looking To Get Their First Thousand Users Or Dollars?

Practice – Even before you are ready to take that leap into your business, find ways to practice and utilize your skills before you are ready. Volunteer using those skills, present/perform for free in an effort to build your own confidence and learn from potential hiccups along the way. That way, when you are pitching/working/looking to be paid, you are coming from a place of experience and authority. Smile – People want to buy or be inspired by people they like, so always remember when asking for anything (money, favors, advice) – smile, be kind and grateful. Even if you get a no, always follow up with a kind word including “thanks.” This may help with more money in the future. Network within your small circle – Share your business with your friends and their friends – it’s amazing how many people want to help with a start-up for users, followers and dollars. Treat them like VIPS – continue to show them love even when you start building momentum.

What Is Something You’ve Learned That Would Not Be Obvious To Somebody Who Hasn’t Worked In Your Space Before?

As the owner of a heartfelt business, sharing my vulnerabilities publicly surprised me. While we all know we should “learn from mistakes,” actually being transparent with ups and downs in business or personal life has gained me more users and thus money because people want to follow and support people they trust. Coming from corporate, I thought it was a sign of weakness to be show too much emotion, I’ve started to use that as my super power and it’s working.

What’s The Craziest Thing That’s Happened To You (Good Or Bad) On Your Founder Journey?

I’ve had a number of unique and unexplainable experiences since being an entrepreneur. My favorite is when I traveled to Atlanta to speak at a conference. It was a whirlwind few days, flying out on my anniversary and needing to leave early to get home to work a fundraiser, I was only at the conference two days. I jumped into a meeting and about an hour into our planning session, the last panelist showed up so I reintroduced myself and shared my cancer story including living with stage IV. One of the women stood up, looked at me and said profoundly, “you’re not sick.” I gave her this weird look because it was an awkward moment and I wasn’t sure what to make of it. She later told me that she’s also a meta-physical teacher and she “knows things.” Now truthfully, I wasn’t sure what I believed in terms of metaphysical but I had this feeling that I wasn’t just in Atlanta to be the “expert on the panel,” I was there to also hear this message. It felt like a sign that this company, this heartfelt work is my purpose and not just a passion.

What Are Your Favorite Books?

My favorite books are oldies, but goodies: “If You Don’t Have Big Breasts, Put Ribbons on Your Pigtails” by Barbara Corcoran and “All I Ever Needed to Know I Learned in Kindergarten” by Robert Fulghum.

Anything You’d Like To Plug?

I’m really proud of “Happiness through Hardship” – The Podcast. It’s filled with inspirational stories of hope intended to bring happiness to your day while guiding you through life’s hardships.

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