Meet Jennifer Pellerito of Jen on the Run & Velvet Leaf Creative

Today we’d like to introduce you to Jennifer Pellerito

Alright, so thank you so much for sharing your story and insight with our readers. To kick things off, can you tell us a bit about how you got started?
I grew up in metro Detroit, Michigan, and moved to Los Angeles for college at Loyola Marymount University. Living 15 minutes from LAX and watching airplanes fly overhead all day had me dreaming about being a passenger on one of them.

After college, I took a two-week trip to Europe, thinking it would satisfy my wanderlust before I settled into a traditional career in the “real world” — but spoiler alert, it did the opposite!

My first job out of college was working at the front desk of a hotel, where I discovered the magic of hospitality. Unfortunately, I wasn’t very good at that job, and I was let go.

But that disappointment opened another doorway for me. I took a job as an assistant for a woman who ran her own marketing business. It was 2013 and we both worked from home – without an office – way before the trend like it is today. It wasn’t flashy or glamorous, but it was a job that showed me how to build a business on your own terms to suit your lifestyle.

After two years, I quit to take a position working in public relations that immersed me in LA’s interior design world, for a business also led by a female entrepreneur. That job had me commuting back and forth on the 405 for two hours a day, to reach an office where I often worked alone, with my boss, or with our part-time intern. After previously working from home, the commute in bumper-to-bumper traffic didn’t make sense. The corporate artwork above my desk depicted Venice’s Bridge of Sighs – just another reminder that I wanted to be out in the world exploring it, instead of tied to a desk Monday through Friday. I admired my boss, who grew and sustained a successful business and worked so hard, but I didn’t love my lack of freedom.

I quit to go freelance when I signed my first client through a referral from a mentor. That soon led to my next client and then my next. I offered social media management back when Instagram carousels were still new, and later, I started copywriting for clients, too. I loved the newfound freedom of running my own business and helping my clients achieve their business goals. At the same time, I also had a few opportunities to write for the local paper covering LA’s dining scene.

Six months after quitting my job, I launched my travel blog, Jen on the Run. I had the freedom to go to my sister’s wedding in Detroit and travel to Sicily and Australia –– all in the same year –– without having to stress out about my remaining PTO days.

Then, my life changed in 2019 when I spent a month in Lisbon, Portugal, returned to LA, and ended a long-term relationship. I found healing through another six weeks of solo traveling in Budapest, Hungary. Traveling was my way of accessing another culture’s value system — one that prioritized rest and enjoyment over constant hustle and burnout — and a way to gain perspective on my life at home.

When the world shut down in 2020, I started Velvet Leaf Creative, a social media and content agency, and in 2021, I met Justin, my partner in both life and creative projects.

Today, I run two businesses — my agency and my travel brand. My journey has been shaped by inspiring women entrepreneurs, bold travel experiences, and a desire to chart my own path. It’s been fueled by a love of storytelling and exploration ever since.

Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
At times, not having an anchor is a surprising challenge. When your work doesn’t dictate where you live, there’s a responsibility to define your own path. It’s all on you: setting your rates, choosing your services, picking your hours, and holding boundaries with yourself and your clients. If something goes wrong, you’ve got no one else to blame, which can be pretty hard to face. Entrepreneurship tests you at every stage, but it’s also shown me how to cultivate a growth mindset.

I often struggle with the fact that my path hasn’t been traditional. Yes, I’ve had six-figure years and kept long-term clients, but my limiting beliefs creep in, telling me it’s not “legit” because I haven’t worked for a big-name brand. But the reality is that taking this nontraditional path has helped me gain incredible resilience, resourcefulness, and time-management skills I probably wouldn’t have otherwise.

Thanks for sharing that. So, maybe next you can tell us a bit more about your business?
Jen on the Run helps people get into freelancing so they can work from anywhere. I’ve seen firsthand how working for yourself can offer you so much freedom and the ability to travel. Jen on the Run fosters a community of like-minded individuals who crave seeing the world and want to live on their own terms. I share firsthand advice on freelancing and travel from the destinations I’ve visited, making it easier to build a flexible, fulfilling career.

Velvet Leaf Creative is a female-founded full-service agency that crafts brand stories fueled by purpose and cultural inspiration. With nearly a decade of experience, we work closely with nonprofit, hospitality, interior design, real estate, and architecture clients who want to embody a lifestyle. By tapping into the art of storytelling and understanding the essence of what makes content resonate, we produce impactful work—sparking inspiration, driving action, and transforming brands into narratives worth following.

We’re driven by the belief that powerful stories shape communities. We connect global influences, hands-on strategy, and polished creativity to produce content that feels authentic. We help clients build cohesive brands, reach diverse audiences, and foster genuine connections that last.

Any advice for finding a mentor or networking in general?
Ask them for coffee. It’s an easy, low-pressure way to get to know someone. There’s really nothing like making an authentic connection in person these days when so many interactions are online.

And if they don’t want to get coffee? No big deal. It’s just coffee, after all.

If you’re just starting to build your network, I’d suggest scheduling 2-3 coffee dates (or more) a month.

Nurture your relationships. Say hi every few months. Ask questions and really listen.

Be direct. If you’re looking for work, say so. You might be surprised at how much people really do want to help when you ask.

And, think of ways you can give it back. I always ask myself, “Who can I connect this person with? Who’s hiring right now? Who’s looking for a job?”

Lastly, find gratitude. I’m so grateful for the friends I’ve made along my creative journey. Some of my most inspiring projects have started with a single conversation that bloomed into an amazing collaboration.

Contact Info:

• Website: www.jenontherun.com / www.velvetleafcreative.com
• Instagram: https://www.instagram.com/jenontherunn/
• Facebook: https://www.facebook.com/jenontherunofficial
• Youtube: https://www.youtube.com/@jenontherunn
• Other: https://www.instagram.com/velvetleafcreative/

Image Credits
Justin Edwards, www.cinemadisco.com
Amira Scott, @byamiramarie