Embrace Resilience

The Unpredictable Path of Entrepreneurship

Building a company is rarely a straight line. No matter how much you plan, how hard you work, or how clearly you see the future, something will come along to upend it all. The question isn’t if that moment will come—it’s how you respond when it does.

Take my friend Claudia Reuter, for example. In 2010, she was in the thick of it: building her first startup with her husband, School Chapters, while raising two young kids. She was making real progress—a contract with a major association, customers, revenue—and finally landed a term sheet from an investor. It felt like everything was falling into place.

Then came the email: “A very vexing issue.” The investment was suddenly at risk. With no childcare and a house full of chaos, Claudia took the call from her son’s closet, surrounded by toys, while trying to keep it together. In the moment, it felt like a disaster. Looking back, it was just another hurdle on the way to success. The round eventually came together; the company grew, and it was acquired. But that moment taught her something essential: resilience.

In our recent podcast episode of Critical Moments, Claudia opens up about this defining moment and how it shaped her outlook on entrepreneurship. She shares the emotional toll of managing uncertainty, the importance of staying focused, and why resilience is the cornerstone of success. You can listen to the full conversation, “A Very Vexing Issue,” on Spotify, Apple or wherever you get your podcasts.

Claudia went on to do great things and achieve significant success in her career. Her journey is inspiring. Among other things, she was Managing Director at Techstars in Boston, where she mentored dozens of startups, helping founders navigate the same challenges she once faced. Today, Claudia leads the Roberts Innovation Fund at Yale Ventures, supporting groundbreaking projects from the Yale School of Engineering and Applied Science. She’s also the host of the podcast The 43 Percent, where she shines a light on the untold stories of women balancing work, family, and ambition. You can learn more about Claudia’s work and podcast here.

Here are three lessons from Claudia’s story that every entrepreneur should take to heart:

1. It’s Never as Big as It Feels

When you’re in the moment, everything feels like life or death. The truth? Most things aren’t. Whether it’s a funding hiccup, a lost customer, or a product delay, these moments rarely define the outcome. What matters is staying calm, putting one foot in front of the other, and moving forward. Claudia’s story in Critical Moments is a perfect example: what felt monumental in the moment was just a bump in the road in hindsight.

2. Resilience is the Job

Entrepreneurship is messy and full of uncertainty. The real work isn’t just building the product or closing the deal—it’s showing up, day after day, even when things feel impossible. Claudia speaks candidly about this in the podcast, recounting how she found the determination to keep going, even when the odds felt stacked against her.

3. Don’t Lose Perspective

The stakes always feel sky-high, but perspective changes everything. Claudia described her startup as her “third child.” That’s how attached she was. But years later, after growing companies, mentoring founders, and working in innovation at Yale Ventures, she sees things differently. Startups are important, but they’re projects—not life itself. This reflection is something she emphasizes in the episode, reminding us all that no single moment defines the journey.

Entrepreneurship will test you. It’s not about knowing the answers; it’s about staying in the game, adapting to the unknown, and finding a way forward. Claudia’s story is a reminder that the journey almost never goes how you think it will—and that’s okay. 🎙️

Listen to “A Very Vexing Issue” and other episodes here.