The Best Way to Tour the Hill...

Throw everything at the wall and see what sticks.

That’s the philosophy of Tour the Hill co-founder Ben Chwalek. It’s the ideal that shaped the entire company. From how it was founded to how they carry out day-to-day marketing activities to how they plan to grow in the future.

Tour the Hill was born from simple yet repeated questions about life outside the classroom at CU Boulder. Campus tours are great for understanding a student's daily academic life and an overall campus vibe, but they can’t encapsulate everything. Factors such as post-freshman housing, Greek Life, and other social scenes all influence where an aspiring student spends four of the most important years of their life. 

That’s where Tour the Hill comes into play. The Hill in Boulder is the most iconic social spot for students at CU. When Chwalek, along with his other co-founders, Liam Zirkle and Parker Henrichon, began answering these questions, it became the perfect opportunity to launch their company. 

Their insights into extracurricular activities and clubs as CU students are what differentiates them from traditional campus tours. Make no mistake, however, as they aren’t trying to replace campus tours, but rather complement them. 

Pursuing an undergraduate degree can reveal a lot about an individual's personality, friend preferences, hobbies - everything about themselves. Tour the Hill can help guide aspiring students to the right spot. With CU being the desirable school it is, it's no wonder people want to learn its social side.

“After a little while, you look at Boulder once, and you realize if you don’t go there, you feel like you’re gonna be missing out on something.” 

That perspective was shaped long before Tour the Hill existed. The founders’ own journeys to CU, and to each other, laid the groundwork for what the company would become.

Founders From All Over

Tour the Hill didn’t start as a polished business plan. It started with three students whose paths crossed in unlikely ways. But it was their interests that kept pulling them back to the same conversations.

Chwalek and Zirkle met in their freshman year in Willard Hall. They came from opposite parts of the country, one from Colorado Springs and one from Massachusetts, but bonded over the shared curiosity for business and how students were finding success in the world of entrepreneurship.

They had received questions from family friends regarding outside life. But it wasn’t until Henrichon entered the picture that the company was finally able to take off. Henrichon and Chwalek met abroad, where the two immediately hit it off and became perfect co-workers and founders.

Henrichon’s insights as a campus tour guide really sparked their idea. He was able to amplify what CU tours showed, but more importantly, what they didn’t. Pair that with Zirkle’s technical skills and Chwalek’s people-first approach to business, and that idea was now a fully operational business.

Guerrilla Marketing

It all ties back to Chwalek’s opening statement: “throw everything at the wall and see what sticks.” 

Tour the Hill officially launched in August of 2025, beginning with a small number of tours during welcome week. Like all startups, their start was a little slower than anticipated, but it’s been their “guerrilla marketing” that has brought them to light.

Email outreach, alumni networks, Google ads, social media, printed flyers, everything. These are just some of the extensive things they’ve done to get it up and running. It was their email outreach that slowly opened new doors for them, most notably partnerships with the Sink and other Pearl Street businesses. These efforts have already led to community partnerships that provide discounts and added value for tour participants, reinforcing the company’s position as a local, student-embedded business.

“There’s so many school resources that we’re really trying to leverage… We’ll just hit people up and be like, ‘Hey, this is what we’re doing, do you have any ideas?’”

This idea has also tied into other aspects of their business. Their pricing has been full of experimentation, trying different price ranges for different groups. At one point, it was per person; now it’s per group. Although it may be subject to change, their main goal is to position themselves as a premium company that offers authentic tours.

Authenticity's Role

Authentic. That’s the keyword for Tour the Hill. While they strive for professionalism in each tour, that doesn’t stop them from traditional formality. Their private tours allow them to showcase Greek Life, the best restaurants/bars, and which housing companies to pursue, or more importantly, avoid. Tour the Hill showcases outside life at Boulder through the general opinion and understanding of an undergraduate at CU.

“Because they’re private, dads will just ask ridiculous stuff, things they would never ask in a group tour, and that’s where the real value comes from.”

That authenticity is also represented through their VIP option. Families get the opportunity to spend an entire day in Boulder, providing a more immersive experience. It’s fully customizable, built around the interests and priorities of the visiting family. The idea isn’t just to show buildings, but to simulate what a real day in Boulder might feel like as a student. They don’t just showcase the aforementioned areas, but they dive right in with the families, giving them a full-on experience. 

While it’s still early and adoption has been limited, the option reflects how Tour the Hill is willing to test unconventional ideas and meet families wherever they are. For the founders, experimenting now is part of building something that can last beyond a single admissions cycle.

A Helping Environment

Tour the Hill is still in its early stages, but its direction is already clear. Built by students who understand Boulder beyond brochures and scripted tours, that authenticity is what drives their company. 

For the founders, progress isn’t about getting everything exactly right. Each decision they make becomes an opportunity to better understand what prospective students and their families actually care about when choosing where to spend the next four years.

Looking ahead, success for Tour the Hill won’t be defined solely by volume, even as growth remains a clear focus for 2026. Their bigger ambition is to become part of the natural rhythm of a CU visit. Most importantly, they’re here to help people, which ties into their philosophy about entrepreneurship as a whole.

“When we picture entrepreneurship, we picture something that has no constraints or ceiling, something you can take anywhere. But it’s also about helping people and holding yourself accountable. You can’t build something meaningful and then show up late, bail on people, or cut corners. It’s kind of chaotic, but it’s all effort toward a goal.”

It ties back into everything they do. They strive to educate about CU in the highest possible capacity. By stepping in after the campus tour ends, families begin asking the questions that truly shape their decision. They’re about commitment while creating value for others throughout the whole process. It’s that mindset that continues to guide them.