Dannelle Gay, the Travel Writer Wearing Multiple (Cheese) Hats

I thought I was spinning a lot of plates in the air until I ran into Wisconsin-based Dannelle Gay at various travel writing conferences and started feeling like a slacker in comparison. She’s the woman behind Traveling Cheesehead, but that’s just a start. She’s also a TV host, book author, freelance writer, commercial photographer/videographer, public speaker, and much more. She also runs four other niche websites including Crazy Camping Girl.

I tracked Danelle down to get the scoop on how she and her team of 15 people manage to keep the production gears turning smoothly. 

You now have a dizzying portfolio of books, TV shows, websites, and even a capsule coffee brand. But where did it all start? What was your path to becoming a travel writer?

I’ve always been a natural storyteller, with a deep curiosity about the world around me. But it wasn’t until I separated my travel writing from my lifestyle website, Operation$40K, that this passion truly blossomed into something bigger. Travel writing allowed me to focus on the immersive experiences and the personal connections that come with exploring new places.

My mom instilled in me from a young age that travel isn’t just about seeing different landscapes or checking destinations off a list—it’s about understanding the world by engaging with people and their cultures. By meeting others, we realize how much we all have in common, no matter where we come from. That’s the magic of travel: finding shared humanity while discovering the unique threads that weave us together.

You call yourself a “serial entrepreneur” in your bio and in an e-mail exchange we had you listed 35 different income streams. Why keep starting new projects when the previous ones are still working?

I’m fortunate to have an incredible team that helps keep everything running smoothly and makes me look both brilliant and organized. For me, there are always new stories to tell and endless opportunities to adapt and evolve to stay relevant. That’s what drives me to keep launching new projects, even when the existing ones are still going strong.

When you love what you do, it never really feels like work. It’s a passion that keeps you moving forward.

How did your outsourcing evolve over the years? What do you still do yourself and what do you have others take care of ?

I’ve always believed that if something doesn’t require my specific talent, it doesn’t need to take my time. Over the years, I’ve embraced outsourcing to streamline my business and focus on what I do best. I have an amazing team that handles tasks like scheduling social media, editing photos, building my email list from Facebook groups, finalizing blog articles, managing newsletters and digital stores, overseeing both physical and digital product lists, prepping for TV segments, and editing videos.

This allows me to stay focused on the creative and strategic aspects of my business while ensuring everything runs smoothly.

Which income streams are the biggest or most profitable for you?

Profit can be measured in many ways. In 2023 alone, I was proud to donate half a million dollars back to Wisconsin non-profits, which is a huge success in my book. Of course, there are also the financial rewards, like cashing large paychecks, maintaining consistent TV sponsorships, receiving book royalties, and generating recurring income from digital sellers.

Ultimately, the most profitable streams depend on your goals and where you choose to focus at any given time.

You’ve been a speaker at TBEX and IFWTWA conferences and you belong to several travel writing organizations. How has that face-to-face networking paid off for you?

You can’t email a handshake. I think where people go wrong is expecting to close a deal in five minutes. Networking is really about building relationships over time. That’s more important than ever in a post-COVID world where people are craving genuine, face-to-face connections.

From my local chamber of commerce to TBEX, I’ve developed a network of trusted contacts that I can confidently refer others to, and also tap into when I need sources for articles, TV segments, or book projects. It’s all about cultivating those relationships for the long term. I can write one email or make one phone call and get fresh ideas.

A perfect example of this is when I was preparing for my first TV show. I called Susan from the Janesville Area CVB and simply said, “I have an idea…,” and before I could even explain what I was doing, she instantly replied, “I’m in.” That is the power of relationships—being able to rely on people who trust you and believe in your vision.

How did your various sites fare in the string of “unhelpful content updates” from Google? What, if anything, are you changing as we move forward?

Some of my sites fared better than others during Google’s unhelpful content updates. To be honest, the ones that took a hit needed some article updating, which was a good reminder to keep content fresh. Being syndicated across platforms like MSN, Newsbreak, and Medium has also extended the reach of my sites, which helps balance out any fluctuations.

Moving forward, I’m still focused on writing for the reader—answering their questions, using SEO effectively, and incorporating both interlinking and external links. I also have a dedicated team reviewing older articles to determine if they need to be updated, optimized, or dropped altogether. It’s all about staying relevant and providing value to the readers.

Dannelle Gay is a Wisconsin native who has been writing about travel for over a decade under the moniker The Traveling Cheesehead. As an award-winning travel writer, regional TV host and published author, and professional chef she is a huge foodie who loves telling the stories of unique people and places.. She has been author or editor of several books and has contributed to multiple publications as a freelance writer. See more at TravelingCheesehead.com.