Katie Hill on Winning Pitches and Building Businesses

Posted by Mike McCann on January 7, 2025

Essential advice for founders on pitching, scaling, and thriving within Dayton’s startup ecosystem

Katie Hill is a dynamic serial entrepreneur, founder, and CEO of Unlisted, a revolutionary real estate technology platform that recently raised $2.25 million in seed funding to connect homebuyers with off-market opportunities. With her experience as an entrepreneur-in-residence (EIR) at the Entrepreneurs’ Center and her dedication to supporting early-stage founders, she has become a trusted guide for entrepreneurs navigating the challenges of launching, funding, and scaling their businesses. In this conversation with Mike McCann, Vice President of Innovation and Engagement, Katie shares insights from her own entrepreneurial journey and offers valuable lessons for aspiring founders.

MM: You started in technology at Leo Burnett (advertising agency) and then became an entrepreneur. At the start of that journey, you moved to Dayton to set up your first startup, and, luckily for us, you have been a leader in our entrepreneurial ecosystem ever since. How did that all come about, and what tips do you have for other entrepreneurs here?

KH: In 2008, I was living in Chicago and starting up a high-tech location-based transit media company. Someone in Illinois mentioned there was an RFP in Dayton for new transit advertising services. We submitted a proposal, and the Greater Dayton RTA invited us to present to their committee. We had never been to Ohio prior to that meeting, but we promised that if they awarded us the contract, we would start our company in Dayton. They did, and we did. We were then referred to Entrepreneurs’ Center (EC) and became clients almost immediately. I can’t believe that was 17 years ago!

At the EC, we found affordable office space and a great deal of encouragement. We arrived with a folding table, two folding chairs, and two laptops. The EC was a turnkey solution; all we had to do was plug in our WIFI and start. We operated CommuterAds at the EC on Monument Avenue for five years and grew to a team of ten employees. And we eventually got real furniture. That’s how my entrepreneurial journey began in Dayton. 

MM: There is a lot you could share with other entrepreneurs—give us three lessons learned.

Lesson Learned 1: Build Strong Relationships

KH: I think it’s important to “Give when you can and take when you need.” Foster relationships where you both give and receive throughout your career. No one gets to sit on one side of that equation forever. The back and forth is what makes the deepest and most rewarding relationships, both professional and personal. 

Lesson Learned 2: Make New Mistakes

KH: You learn a lot in the first five years with a startup. Seek out mentors who have “been there and done that.” Remain coachable and listen to their advice. The EC is a great resource for access to seasoned entrepreneurs and business executives. Many of the EC’s programs are designed to help founders avoid common pitfalls. EIRs provide guidance on things like product development, hiring, go-to-market strategies, regulatory landscapes, and funding. The EC also has a network of service providers like attorneys, accountants, and HR specialists who understand the unique needs of a startup. Leveraging these resources really helps new founders avoid common mistakes. That way they can save their energy for new, trailblazing mistakes!

Lesson Learned 3: Master Your Investor Pitch

MM: As an entrepreneur-in-residence here at EC, investor presentations are your specialty. You’ve won multiple competitions personally and coached numerous entrepreneurial teams. You are the only two-time winner of the University of Dayton’s Flyer Pitch (in 2010 for your first startup, CommuterAds, and in 2023 for Unlisted). This spring Unlisted won Pitch HearstLab New York and received a $100,000 investment. You’ve coached seven teams in pitch competitions at the University of Dayton; five of those won first place. Share your advice.

KH: I have now observed more than 500 pitches. Sitting on both sides of the table has made me understand what it is like to craft a presentation as an entrepreneur and what it is like to be an investor on the other side. Here’s some of what I’ve learned. 

  • Put yourself in the seat of the person listening to your story. What does the person you are presenting to care about? Do they care about revenue? Users? Job creation? Be sure you know your audience. That’s #1.
  • An investor presentation is not about showing off how smart the founders are. Too many entrepreneurs want to go into excruciating detail about their technology, which is impressive but leaves the audience dazed and confused. Instead, we coach founders to talk about the world in which their technology is relevant. They need to discuss the problem they’re solving, their plan to gain traction in the market, and their path to a promising exit. The point is for investors to feel smart for seeing and jumping on the opportunity.
  • Pitches should be a mile wide and an inch deep. Present a little bit about many key topics related to your venture and allow the Q&A portion of the meeting to guide you where to go deeper with a particular audience. 
  • Learning about venture capital and vetting investors puts entrepreneurs in a more powerful position. Asking for money isn’t easy and can make you feel vulnerable. Remember, investors need great founders with great ideas, or they are out of business, too. Founders need to remember they bring important value to the table, too; that changes the dynamic.

Katie Hill’s journey illustrates the impact of resilience, the value of mentorship, and the power of a well-crafted pitch. Her insights offer aspiring founders a roadmap for success and highlight the support available at the Entrepreneurs’ Center, where entrepreneurs can find resources, build connections, and accelerate their ventures. Want to learn more about how to become an EC client? Connect with us.

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