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MOMpreneur Monday: Rachel Sobel, Whine and Cheeze (its)

MOMpreneur: n. defined as a female business owner who is actively balancing the role of mom and the role of entrepreneur.

Welcome to our next installment of MOMpreneur Monday, highlighting Florida businesses and brands that were founded by female entrepreneurs and fellow Mommas.

Suzanne Kline on Modern Boca Mom


Today’s featured Modern Boca MOMpreneur is...freelance writer, content creator and blogger Rachel Sobel of “Whine and Cheez (its)!”

Rachel Sobel


Tell us a little bit about your background, motherhood and what inspired you to start your blog “Whine and Cheez (its)”…

I was one of those weird people who picked a college major, stuck to it, and pretty much stayed in that industry (with a few slight tangents here and there) for my whole career. I decided to major in Public Relations about 5 minutes after I unpacked my shower caddy in my dorm room at the University of Florida (GO GATORS!), went on to get my masters at FIU and got my first job offer from a small boutique PR agency specializing in real estate, 8 minutes from my childhood home in North Miami Beach. My salary was embarrassing (no really, I’m pretty sure my 7-yr-old has more in her piggy bank than I made in a month), the hours were horrible and I learned more in that first year about client service and egos than I did over the next 10 years.

Life took me to the Northeast a few years later and I landed at another agency in Boston with a polar opposite niche in technology. I knew NOTHING about tech…I think I had just abandoned my AOL account for a Yahoo one, but they took a chance on me and it became my home for many years. I loved it, thrived, made amazing connections, learned a lot and unleashed my inner nerd. I would write a press release about a website security tool or pitch a reporter about infrastructure software and kind of feel like I had been possessed by a really smart chick who knew her ish.

I had my daughter a couple years into that job and it rocked my world. I was torn about maternity leave ending, but also actually looking forward to being amongst wicked smart adults and wearing clothes not covered in spit up.

“Becoming a mother definitely changed my perspective about EVERYTHING at work. I managed to create a balance that (mostly) worked for me and learned to leave stuff at work to be present for my daughter, but it was hard.”

Rachel Sobel

When I moved back to South Florida more than a decade later, with a toddler in tow and a skill set foreign to the job market here, I took a couple years off from being somewhere full-time and instead dabbled in freelancing so my mind wouldn’t turn to mush from hours of the Disney Channel and Nick Jr. Little did I know that would set the stage for my current career move.

I caved a couple years ago and took a full-time, in-house gig with a local tech company and ended up hating it. All the while, I was still freelancing (more than ever actually) and launched my own mommy/lifestyle blog, Whine & Cheez (its). I eventually left this past November when I felt like I had an arsenal of work on the freelancing side and a rapidly growing readership for my own stuff. It literally changed my life. I am able to spend SO much more time with my daughter, have the ability to pick and choose the clients I work with, and am happier than I have ever been!

Rachel Sobel
How do you juggle your blog and freelance clients?

My business is interesting because there really are two sides of it that don’t really intermingle. There’s my Rachel Sobel freelancing and there’s my own blog/lifestyle brand. They are very different beasts, but both serve a purpose in my life.

In South Florida, the overwhelming majority of people hiring freelancers for writing or PR are very consumer-focused. My experience is the exact opposite, Professionally, my sweet spot is in tech and B2B. While I was a dime a dozen in markets like Boston and NYC, down here it’s a little harder to find us.

Something inside me told me never to give up my freelancing contacts. I didn’t have this master plan about going off on my own, but I felt strongly about maintaining my contacts, finding new ones and maintaining a presence in the freelancing world. When I was working full-time, I had no intention of leaving. But things began to escalate so quickly, my misery was palpable and I just needed a change. I also had some of the challenges many of us have – I have a mortgage, and a child, and bills, and I like to go out to dinner whenever I want. I needed/wanted a source of income, but just didn’t want to work for anyone else a minute longer. The other thing I realized was that. I didn’t want to be a “PR Gal” anymore. I just wanted to create content. Period. Once I made that distinction, I literally sprung into action, got my hustle on and grew a small roster of clients I solely created content for. Holy Crap! This could work!

“When I realized I was basically matching my full-time salary writing and creating social media content, and could work from the comfort of my home in yoga pants and no makeup, I took the leap and became a solopreneur. I am a creative at heart, so thank god my husband is there to do things like set up an LLC, do my billing and tell me what steps I need to take to be a “real” business. Behind every great woman really is a great man.”

Rachel Sobel

What’s unique about Whine and Cheez (its) and your client content?

People I create content for tell me that they love my voice and that I am authentic. I, Rachel Sobel, have a pretty strong personality and I’ve always been told that when people read my writing, they can hear me saying the words, see my facial expressions and arms flailing, and it feels like we are having a conversation. The brands who engage with Rachel Sobel to work with the Whine & Cheez (its) side are totally into my voice, not afraid of inappropriate jokes and some salacious language. That’s why it works.

The challenge for many writers is translating that skill to other more “businessy” areas of writing. I’m not saying I’ve mastered it, but I think I have a really strong handle on breathing some life into what has always been viewed as the “boring” writing. I love diversifying my writing and having the opportunity to dig into something super techie or business focused.

Rachel Sobel

Why should MBM readers consider becoming your client?

Over the last two decades, I feel like I have truly amassed a ton of knowledge and experience to diversify my writing. I have written for startups with an office consisting of a card table and folding chairs and major companies with logos that cost more than my house. I pride myself on my ability to meld with different personalities and company cultures, understand your products/services and how to translate them into well-rounded and meaningful content. With every client, past and present, I build a rapport that manifests in my writing versus just serving as a contractor who may or may not deliver what you need. If you are hiring Rachel Sobel to write for you, I view myself as an extension of your brand and I take that very seriously.

What new and exciting things are coming up for your business?

From the freelance side, I have expanded my network so that I can take on fuller scope accounts that may want more than content. My friend who did something similar told me that she found having a blank invoice template at hand allowed her to focus more on the writing a less on the admin. I am able to still churn out the content I am passionate about while I work in tandem with trusted Rachel Sobel partners to deliver the rest, without sacrificing quality.

With Whine & Cheez (its), I am experimenting with new content formats including video and podcasts. As a matter of fact, I am working on a few exciting collaborations with a couple of daddy bloggers I love, who are like male versions of me and I can’t wait to share that with the world! Stay tuned!

What do you love about living and working in South Florida?

While I absolutely loved my time in Boston and NYC, being back in South Florida with my family and girlfriends is the best. I feel like I have my own little army of awesomeness – I guess it’s called a squad now. Whatever… I, Rachel Sobel, have one and it makes my life better everyday to be surrounded by unconditional love and support.

Plus, it’s pretty wonderful not to have to bundle up a child and push a stroller through snow to get to an overpriced grocery store and pay $12 for 4 rolls of toilet paper.

I’m home, doing what I love and it doesn’t get better than that, does it?

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Follow Rachel Sobel & Whine and Cheez (its) on Social Media:

Website-Whine and Cheez (its)

Facebook- Whine and Cheez (its)

Instagram- Whine and Cheez (its)

Twitter- Whine and Cheez (its)


SUBSCRIBE to Modern Boca Mom here!

Rachel Sobel on Modern Boca Mom

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Michelle Olson-Rogers, Modern Boca Mom Headshot

Michelle Olson-Rogers is the founder of Modern Boca Mom, a leading lifestyle site for the stylish & modern South Florida mommy. ModernBocaMom.com features local businesses, events, lifestyle and family travel options and was the proud winner of the 2019 Florida Blog Con Sunshine Award in the “Favorite Events/Neighborhood Blogger” category. Michelle is also a regular contributor to Boca Raton magazine.


In addition to blogging, Michelle also serves as the Director of Communications and Community Outreach for Grandview Preparatory School, a private PK3-Grade 12 independent school in east Boca Raton. Her successful “Modern Boca Mommy & Me” program has been running there year-round since 2014.

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