Meet Jenn Hartt | Creative Strategist

We had the good fortune of connecting with Jenn Hartt and we’ve shared our conversation below.

Hi Jenn, is there something that you feel is most responsible for your success?
The most important factor behind my success and the success of my brand is simple – community. I’ve built my business on the foundation that success isn’t a solo journey; it’s about meaningful connections, shared experiences, the desire to lift up others, and have people to fall back on when entrepreneurship gets hard (which it does). My goal an an entrepreneur is to create spaces and opportunities for other entrepreneurs to be their most authentic, aligned selves. This journey can be a lonely one, but if we have others to lift us up, inspire us, and stand in our corner, it makes it an even better one.

My podcast, Your Next Business Bestie, exemplifies my commitment to community. I launched my podcast in 2024 as a way to connect humans, especially those self-employed, to other amazing humans I believe they need to know. I give entrepreneurs a platform on which to share their stories – the good, the bad, and the ugly. The authentic sharing of stories has the power to save and to change lives. When we show up as our most authentic selves, we create space for others to do the same.

Alright, so for those in our community who might not be familiar with your business, can you tell us more?
I started my business as a virtual assistant because, after working in so many different facets of small business I knew firsthand how much entrepreneurs had on their plates. I wanted to help take things off their to-do lists so they could focus on what they loved. I enjoyed helping them get a little bit more time back to actually enjoy the “why” behind their business. As I worked with more and more clients, one thing became clear, what I was offering was more than checking tasks off a list.

I was helping my clients structure their systems, refine their messaging, create content that connected, and build a foundation for sustainable growth. I was offering high-level creative strategy, guiding them through decisions that shaped their businesses. After a ton of feedback from my clients and my community, I rebranded as a creative strategist to reflect the work I was truly doing.

What sets me apart is my ability to pivot—not just in my own business, but in how I support my clients. Entrepreneurship is constantly shifting, and I thrive on adapting to my clients’ needs and the ever-changing landscape of online business. Whether it’s designing a Squarespace website, crafting copy that speaks directly to an audience, managing social media in a way that feels authentic, or structuring systems to keep everything running smoothly, I approach every project with a mix of strategy, intuition, and deep understanding of what makes a business work.

My absolutely favorite part of my business and my day-to-day is that moment when a client sees their vision come to life—the website that finally feels like them, the social media strategy that clicks, the email newsletter that connects on a whole new level. That’s the magic. That’s the dopamine hit that makes all the hard work worth it.

Entrepreneurship is messy, and I’ve had plenty of “what the hell am I doing?” moments. But I’ve learned to trust the process, follow the energy, reach out to my community, and lean into what feels right. I bring a little bit of witchiness into everything I do—not in a gimmicky way, but in how I read people, spot patterns, and help clients align their business with their true vision. When we move with intention, when we create from a place of alignment, things fall into place in ways that feel almost magical.

At the end of the day, my brand is about connection, creativity, and making things happen. I’m not just here to check off tasks—I’m here to help entrepreneurs build businesses that feel good, function smoothly, and give them the freedom to focus on what they love.

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
Attractions:
Cheyenne Mountain Zoo in Colorado Springs is a must – this is one of the many places I fell in Colorado
We’d have to swing through Garden of the Gods this day as well and take a drive down the Gold Camp Road for the incredible views
Denver Museum of Nature and Science is always a fan-favorite
No trip to Colorado is complete without heading over to Red Rocks Amphitheater
Depending on the time of year, a stop by the Denver Botanic Gardens would also be amazing

Food & Drink:
Personally I love to cook, but we could hit up some of the amazing farmers markets to support local and get the freshest ingredients to make some incredible dishes
View House in Colorado Springs is a great spot for happy hour and a view of Pikes Peak
Cork and Cask in Colorado Springs takes you back into the prohibition era and their bar is a beauty to look at
We’d grab coffee at Forge Coffee Lab in Monument on our drive back to Denver

Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
I’ve had the immense pleasure of meeting hundreds of inspiring individuals throughout my career. Before launching my business in 2018, I spent years working in small businesses and the direct sales industry—experiences that deeply influenced my approach to entrepreneurship.

From managing finances for a construction company to handling scheduling and invoicing for an irrigation business, and even designing textbook covers, I gained firsthand experience in the daily operations of running a business. My deep love for systems and research grew from those years, as I saw how structure and strategy could determine a small business’s success.

In direct sales, I discovered the true power of community—not just within my own team, which grew to nearly 250 consultants, but also through the connections formed at countless craft fairs. We celebrated each other’s wins, supported one another through long days, and built relationships that extended beyond sales. While direct sales gets a lot of criticism on social media these days, it taught me invaluable sales fundamentals and reinforced the importance of meaningful connections in business—something I carry with me to this day.

Specific shout outs would have to go first to Kami Guildner and her Extraordinary Women Ignite event. It was at that event in 2021 that I decided to stop putting all my time and energy into someone else’s business, I was working full time at the time, and instead really commit to building my business. It was that next year that my business went from 5 figures to 6.
Diana Davis has also been instrumental in my success. I signed up for her coaching program, Camp Clarity, in 2022 and her Ascend program in late 2022, early 2023. Not only did Diana help me find my footing in my growing business, but the community she continues to introduce me to is priceless.

Website: https://www.jennsway.com

Instagram: https://www.instagram.com/lifejennsway

Linkedin: https://www.linkedin.com/in/jwayboer/

Facebook: https://www.facebook.com/jenn.wayboer/

Youtube: https://www.youtube.com/@lifejennsway

Other: https://podcasts.apple.com/us/podcast/your-next-business-bestie/id1750425864
https://open.spotify.com/show/0YdrLAVoxtjDQXZ4BeF66p?si=ca4707af85944344

Image Credits
Avery Williams
Nicholette Hilbrich
Meghan Blanton