From Skeptics to Supporters: Catherine Connelly on Navigating Doubt and Designing Her Own Path

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Catherine Connelly on Co-Founding MyYearbook as a Teenager, Gender Bias in Tech and Designing Success

Catherine Connelly co-founded the social platform MyYearbook as a teenager, growing it to more than a million users in nine months, and is the author of Designing Success. On Your Brand Amplified, she explains how the platform grew by listening to its users, what building a company in high school cost her, and how she now mentors younger founders.

How did MyYearbook reach a million users in nine months?

By starting with a real problem and adapting to how people actually used it. Catherine and her older brother, whose example first got her thinking like an entrepreneur, both had trouble making friends at a new school. They imagined a digital space that would make that transition easier. With no technical background, Catherine and her team outsourced development to a team in Mumbai through Elance.

Early growth was grassroots: customized t-shirts worn around school, quizzes and personalized content. The bigger factor was responsiveness. Instead of holding to the original concept, the team followed user behavior, expanding from a school-focused tool into a broader space for meeting people nearby. Features like "Battles" came directly from community input. MyYearbook passed a million users within nine months.

What does building a startup young cost a founder?

Catherine balanced the company with high school and later college, through constant prioritization and boundary setting. The pace took a toll on her health and made her rethink what sustainable leadership looks like, including the role of self-care. She points out that these emotional and physical demands are often overlooked, particularly for young and underrepresented founders who feel extra pressure to prove themselves.

How did Catherine Connelly deal with gender bias in tech?

She was underestimated repeatedly, first by high school peers who dismissed her achievements and later in male-dominated professional settings. In college, where professors and classmates understood her role, she finally felt recognized. She calls being underestimated a double-edged sword: frustrating, and also a chance to surprise people simply by being prepared and confident. She now advocates for structural changes that make female leadership in tech normal and open accessible paths for underrepresented founders.

What does Catherine Connelly focus on now?

Writing and mentoring. Through her book Designing Success, office hours and challenges, she helps younger entrepreneurs build businesses and lives they are proud of. She sees community building as more than networking: generosity, shared experience and mutual support. Her work distinguishes performative entrepreneurship from sustainable innovation and centers on impact and human connection rather than scale alone.

Key takeaways

• MyYearbook started from a problem its founders lived: making friends at a new school.
• Non-technical founders can build products by outsourcing development, as MyYearbook did through Elance.
• Following user behavior, not the original plan, drove growth to a million users in nine months.
• Startup pace has real health costs, especially for young founders; self-care and boundaries are part of sustainable leadership.
• Being underestimated can be met with preparation and confidence, alongside advocacy for structural change.

Free resource: Catherine is offering YBA listeners a free virtual copy of her book Designing Success. If you are not yet on Audible, you can also get the audiobook free when you sign up for a trial through this special Audible link.

Listen to Anika Jackson's full conversation with Catherine Connelly on Your Brand Amplified.