Robbie Cape: From Public Failure to $129 Million CEO — Here’s How He Did It

“Life isn’t about how many times you fall down. It’s about how many times you get back up.”

We’ve all heard this quote at some point in our lives.
It may sound like a cliché, but that doesn’t make it any less true.

This is the quote that came to mind when I sat down with Robbie Cape, co-founder and CEO of 98point6.

Failure is inevitable. We’ve all faced it, whether in our personal lives, careers, or businesses. But how many of us have faced failure in front of millions and still found the strength to rise again? Robbie Cape is one of the few who not only bounced back but used his setbacks as stepping stones to greater success.

During his 12-year run with tech giant Microsoft, Robbie was offered one of the most prestigious positions at the company — leading a massive project codenamed HailStorm, which at the time was Microsoft’s largest project. He even met with Bill Gates himself to discuss the project, with all eyes on him.

But just two months later, everything changed.

“I was called into my boss David’s office the night before I was going on vacation with my family. He fired me,” Robbie shared. “I crashed and burned publicly. Thousands of people were watching. It was the only time my son, Benjamin, saw me cry. I couldn’t believe it — it was my lowest point.”

We’ve all been there, right? The moments where we feel like we’ve hit rock bottom and can’t find our way out. It’s a universal feeling.

But failure isn’t the end — it’s a part of the journey. The key isn’t avoiding obstacles but knowing how to overcome them.

Robbie did exactly that.

After his public failure at Microsoft, Robbie didn’t give up. Instead, he turned the setback into a powerful lesson. He went on to found his first company, Cozi Group, which was acquired by Time Inc. after a successful 9-year run. Not stopping there, he co-founded 98point6, revolutionizing the healthcare industry and raising nearly $130 million in funding.

Today, 98point6 is reshaping primary care, making healthcare more accessible than ever before.

Robbie’s story is a testament to resilience. It’s proof that no matter how hard you fall, you can always get back up. And sometimes, those failures are the exact thing that propel you to your greatest successes.

The next time you face a setback, remember: where there’s a will, there’s always a way.