I recently had the privilege of sitting down with Outreach CEO, Manny Medina, and hearing the personal story behind his success. At the time of writing, Outreach is valued at over $1 billion — and Manny’s insights during our conversation were both powerful and practical. His mindset and philosophy have shaped not only the company, but also the way he leads and lives. I believe his story can offer real value to anyone striving for growth — both personally and professionally.

Here are the top 3 takeaways from our conversation:

1) Legacy Over Currency

One of the first things Manny shared was this: legacy matters more than money. Chasing short-term gains might bring temporary wins, but long-term impact comes from focusing on something bigger than yourself. Growing up in Ecuador, Manny always felt called to serve others — whether by addressing poverty, increasing access to education, or improving healthcare. That sense of purpose stayed with him as he entered the world of business.

While entrepreneurship is often linked to wealth, for Manny, it’s more about building something meaningful that lasts. Something that helps others. Something that lives beyond him.

When it’s all said and done, how do you want to be remembered?

2) Stay Curious

Another powerful trait behind Manny’s success is his deep curiosity — especially about people. He doesn’t settle for surface-level talk. Instead, he’s always trying to understand what drives someone. What motivates them. What’s their story?

This kind of curiosity isn’t just good for building relationships — it’s a superpower for any leader. Because once you understand what truly moves a person, you can lead, mentor, and support them far more effectively.

So ask yourself: What’s your “why”? And do you know the “why” of the people around you?

3) Fail Fast, Fail Forward

Lastly, Manny emphasized that failure isn’t something to fear — it’s something to embrace. If you’re not failing, you’re probably not pushing your limits. And if you’re not pushing your limits, you’re not growing.

His advice? Expect failure. Make peace with it. Let it teach you. Because failure isn’t the opposite of success — it’s part of the journey. In fact, the only real failure is not trying at all.

So get uncomfortable. Take risks. Learn. Improve. And most importantly — keep moving forward.

Did you take a bold step today? If not, maybe now’s the time.