Catherine Connelly (B’11) on the Importance of Making Mistakes, Trusting Your Instincts, and Designing an Environment for Success

Georgetown McDonough joins the nation during the month of March to celebrate Women’s History Month. For the School of Business, this history began in 1960 when the newly formed school awarded its first business degree to a woman. This historic moment set the stage for the extraordinary achievements of six decades of female graduates, who continue to break barriers and pave the way for future generations of women business leaders. 

To celebrate Women’s History Month, we are highlighting McDonough alumnae who have pushed boundaries and found success in their personal and professional lives.

Before stepping foot on the Hilltop, Catherine Connelly (B’11) was an entrepreneur. As a high school student, she co-founded a tech startup that would become a NASDAQ-listed company with millions of active users. In Connelly’s nearly two decades as an entrepreneur, she has helped scale some of the top social apps in the world, in addition to becoming a best-selling author and speaker. She is a recipient of the Ernst & Young Entrepreneur of the Year Award for the Philadelphia Region and has appeared on CNBC, ABC News, the Wall Street Journal, and more. 

What drew you to Georgetown?

When I was applying, the company I had cofounded, myYearbook, had just raised a $4.1 million Series A, which is the first round of institutional funding. I always wanted to go to college and saw it as both a learning opportunity and a way to hedge my bets. I was hyper aware that my company’s value could fall to zero at any point. I also wanted to meet people who would challenge and inspire me. Georgetown, with its strong academic reputation and student community, seemed like the right place to do that. I knew from my first steps on campus that it felt like home.

What were some of your favorite experiences as a student?

I took so many exceptional courses that challenged and shaped my thinking. My favorite part of my experience, though, was how strong our community was. I lived on New South 4 and Father Christopher Steck invited a group of us to watch the show House on his TV when the one in the common room wasn’t working. What started as a one-time favor turned into a weekly tradition. We returned for every new episode until we graduated.

Georgetown Entrepreneurship was just getting started when I graduated. However, visiting campus recently, I saw firsthand how Jeff Reid and his team have grown the Georgetown entrepreneurship ecosystem, from pitch competitions to accelerators and many more fantastic resources for student entrepreneurs. I’m so proud to be a Hoya and see what these Hoyapreneurs are building.

I’ve also loved that although I graduated in 2011, Georgetown is still a welcoming space for me. I’ve had the opportunity to return to Georgetown as a guest lecturer and participate as a keynote speaker at some events on campus.

How did Georgetown prepare you for your career?

One of the most impactful experiences was realizing early on that I needed to ask for help. Just a week into my freshman year, I was invited to speak at the World Knowledge Forum in Seoul, South Korea, alongside CEOs and global leaders, but it conflicted with a midterm. My professor had made it clear that no one could reschedule, yet I decided to ask anyway. To my surprise, he was delighted and happy to support me. 

That moment showed me how valuable it is to advocate for yourself and seek support when needed. It helped shape how I balanced being a student, an entrepreneur, and the rest of my career. Knowing when to ask for help is one of the most important skills you can develop, and I was lucky enough to practice it in a supportive and welcoming community as I built my confidence and expertise. 

Is there a woman — whether a mentor, professor, peer, or public figure — who has inspired you throughout your journey?

Yes, many! In my career, I’ve found that women are enormously supportive of each other, and I’ve felt that support grow as my career advances. 

At Georgetown, Dr. Betsy Sigman was an important mentor to me. In college, I initially didn’t want to talk about myYearbook with peers or professors to avoid some of the negativity from high school. During my sophomore year, Dr. Sigman found out about the company and had me share more about it in class. Once I started opening up to professors and friends, I found Georgetown enormously supportive. 

After college, Dr. Sigman continued to support my career. She was the first person outside my family to whom I told I was leaving my company, and she encouraged me to write, which led to my publishing of Designing Success: Lessons from 20 Years as a Female Tech Entrepreneur.

Did you ever experience any career obstacles, gender-related or otherwise?

Absolutely. Being a female entrepreneur, especially in tech, meant facing skepticism that my male counterparts didn’t always encounter. For instance, as a college junior, my “award” for being a finalist in a national student entrepreneurship competition was a man’s watch and a bottle of cologne.

In high school, I learned that being a smart, ambitious girl could be a disadvantage. Whereas my brother and co-founder’s classmates thought what he was doing was cool, I found that some people in my class said I was “making them look bad” or was a geek or a loser.

Throughout my journey, there were moments when I was underestimated or not taken seriously. But rather than letting it discourage me, I focused on what I could control: building a great product, growing a strong team, and surrounding myself with supportive people.  

What are some key lessons you have learned throughout your career as a tech entrepreneur?

1. You don’t need to have all the qualifications to start – I co-founded my first company at 15 years old. I had no formal business training, but I learned by doing. Many of the most successful people I know took a similar path — they didn’t wait until they felt “ready” because no one ever really does. You chase your curiosity and learn along the way.
2. Design your environment for success – So much of our stress and burnout comes from systems and processes that don’t work for us. I learned that in order to be successful, you need to sculpt your environment to be conducive to your growth, no matter how you define success. That means quitting the things that don’t serve you, setting and holding boundaries, and fostering connections. When you’re intentional about how you spend your time and who you spend it with, you can prioritize what truly matters to you.
3. Get comfortable with uncertainty – On my journey as an entrepreneur, there were high highs and low lows, and probably more lows than highs. Not every feature launch we had was a success, and not every update had game-changing results. Many nights, it felt like there was no light at the end of the tunnel, and there was no sense at all that what we were working on would succeed. Dealing with ambiguity is one of the hardest things to do because the fear of making the wrong decision can be paralyzing. Nobody likes to fail. But I believe that if you’re not making mistakes, then you’re not making decisions.

Looking back on your time at Georgetown and your career, what advice would you give your younger self?

I’d tell my younger self to trust her instincts and take up space. It’s easy to second-guess yourself when you’re young — whether that’s hesitating before speaking up in a room full of more experienced people or feeling like you need to prove your worth before you belong. But I learned that nearly every successful person experiences imposter syndrome and doubts themselves. 

The trick isn’t to completely silence those voices of doubt in your head; instead, it’s to master letting ourselves shine despite those voices by learning how to turn the volume down. I’d also remind myself that success isn’t just about external achievements and milestones; it’s about designing a life that supports all parts of who you are.