What inspired you to create Stayfi?

I wanted to build a SaaS business, and my approach was to work in marketing consulting across various industries to identify a gap that could be solved with software. While consulting for a vacation rental company, I noticed a significant challenge: they struggled to build their own brand and drive direct bookings because they lacked effective ways to collect guest data. StayFi emerged as the solution to this problem, allowing vacation rental companies to capture guest information and directly remarket their brand to past guests.

How does Stayfi look different now versus when you first started? What have been some challenges/learnings along the way?

StayFi has evolved from a one-man operation with limited outside investment into a company with 16 employees and 3,200 customers. Early on, it was crucial to find the right customers—those who immediately understood the value of our product—even if 90% of prospects didn’t get it. Identifying these early adopters was essential; they provided the proof and motivation that the broader industry would eventually recognize the impact of our solution. One of the biggest lessons was learning to persist despite initial resistance and to keep refining the product until the market caught up.

Are there any particular partnerships or collaborations that have been pivotal to your success?

Finding a CTO who was both technically skilled and capable of growing into a management role was a game-changer for StayFi. This key hire came through my personal network, which has been instrumental not only for recruiting top talent but also for strategic partnerships that have driven our growth.

You were recently named the #1 App in GetApp's Category Leaders in Vacation Rental. How do you define success for Stayfi?

Success for StayFi is about shifting the balance of power in the vacation rental industry, enabling operators to build and market their brands independently of OTAs. It’s about empowering hosts to reclaim their guest relationships and create a sustainable, direct booking model.

What’s next for Stayfi and the short-term rental space? Where do you see this industry in the next decade?

In the next decade, I envision StayFi playing a crucial role in the rise of distinct vacation rental brands that guests recognize and trust. We aim to disrupt the current booking landscape by empowering property managers to control their marketing destiny and connect directly with their guests, reducing their reliance on OTAs.

What led you to GAIN? What has been the highlight of your experience working with GAIN investors? How has GAIN influenced your alumni experience?

GAIN has been an invaluable partner, connecting us with investors who have participated in multiple rounds of funding for StayFi. Through GAIN, I was also introduced to another angel group that played a pivotal role in securing our first round of outside funding. These connections have been instrumental in StayFi’s growth.

What is your favorite memory from your time on the Hilltop?

Spending days outside on the grassy quad when the weather finally turned nice in the spring!

Thinking back on your Georgetown experience, can you speak to how classes, friends, clubs, etc influenced your entrepreneurial journey?

During my freshman year, I became involved in a student-led movement that challenged how the University engaged with and supported LGBTQ students (https://lgbtq.georgetown.edu/history/10thanniversary/). We were the underdogs facing a much larger institution, but through coalition-building, peaceful protests, and unwavering determination, we made meaningful change. This experience taught me invaluable lessons about perseverance, resourcefulness, and the power of community—skills that are directly applicable to founding a startup, especially in the early, under-resourced stages.

If you could give a piece of advice to a Hoyapreneur or aspiring Hoyapreneur, what would it be?

Don’t fall into the trap of thinking that venture capital is the only route to building a successful business—it’s not, and for most, it shouldn’t be the default choice. Having deep, relevant experience in an industry can give you unique insights that are often the most valuable assets you bring to your venture. Focus on solving real problems you understand well; the rest will follow.

Arthur Colker (SFS’11)