I met Santi Jaramillo on a Vision Quest. From the moment we connected, I knew there was something special about him – not just as an entrepreneur, but as a person who deeply cares about people and the culture within a company.
In our conversation, he shared his journey, the lessons he learned about leadership, and how to create a thriving business by focusing on what really matters: the people who make it all happen.
Santi’s Entrepreneurial Beginnings
Santi’s entrepreneurial journey started early – selling avocados to his parents’ friends as a kid growing up in Cali, Colombia.
His knack for business only grew from there. By the time he was in college, he had entered the tech space, getting involved with a SaaS startup called ExactTarget. That’s where he fell in love with the idea of building companies that could scale globally while creating a workplace people actually love.
One of his first major ventures was Bluebridge, a startup that created white-labeled mobile apps for the tourism industry. At its peak, Bluebridge powered apps for destinations like Visit Colorado, Visit South Africa, and Visit Indianapolis.
They even expanded into apps for mega-churches. Santi was a first-time CEO in his 20s, and it wasn’t all smooth sailing. He told me, “I made so many mistakes and learned so much, especially about managing people and being a leader.”
The Shift to Culture and Leadership
After selling Bluebridge, he had a realization: he wasn’t passionate about tourism or church apps. What he really cared about was organizational culture and leadership – how to create an amazing place for people to work and lead teams with integrity.
That’s when he and his business partner, Adam, shifted their focus and launched Amplify.
Amplify was all about helping leaders understand and improve their organizational culture. They developed tools to measure culture in a way that gave leaders real, actionable data. It wasn’t just about thinking you had a good culture – it was about knowing exactly how your employees felt and what needed to change.
Santi shared something profound with me: “70% of employee engagement isn’t about perks or even culture itself, it’s about the quality of leadership.”
That was the big insight that guided Amplify’s success. They didn’t just stop at collecting data; they used it to coach leaders – helping them grow based on how their teams experienced their leadership.
Leadership Is About Hard Decisions
One of the key themes Santi and I discussed was how leadership is often about making hard decisions. It's about holding people accountable and making tough calls for the sake of the team and the business.
Santi said something that resonated with me: “Culture isn’t defined by the core values painted on the wall, it’s shaped by the actions of leadership.”
Who you hire, who you promote, and who you let go defines your culture more than any mission statement ever could.
I’ve experienced this firsthand. Sometimes, you have a top performer who’s delivering results but creating chaos within the team. Do you keep them because they’re producing, or do you part ways to protect the culture?
These are the moments that define leadership.
From Surviving to Thriving
Early in his career – like many entrepreneurs – Santi was just trying to stay afloat, hitting goals, solving problems, and growing the business.
But after the Vision Quest, he had a breakthrough. He realized that thriving isn’t just about hitting numbers, but about creating something you’re truly passionate about.
This shift in mindset was huge. When you’re in survival mode, you’re constantly reacting. But when you move into thriving, you begin creating something meaningful and long lasting. It’s a whole different way of running a business.
Play and Creativity in Business
One insight Santi shared that really stuck with me was about the power of play and creativity in business.
He said, “You can’t play if you don’t feel safe.” And that’s so true. When you’re stuck in survival mode, it’s hard to relax and think creatively.
But play is where innovation happens. When you give yourself the space to explore new ideas, you open up to possibilities you might not have seen before. For Santi, building a business is like creating art. That means creating an experience that people want to be a part of.
Leadership Growth Is Personal Growth
Santi told me something that really hit home: “Leadership growth is human growth.” To lead well, you need to work on yourself first.
Here’s what that looks like in practice:
→ Start with self-improvement
Your growth sets the tone for your team. The more you focus on improving yourself, the more you inspire others to do the same.
→ Stay open to learning
A good leader never stops learning. Keep asking, What can I improve today? Your team will mirror that curiosity and drive.
→ Be the example
Your team watches how you handle challenges and growth. Show them the way by staying calm under pressure and pushing yourself to grow.
→ Lift others by improving yourself
When you focus on becoming better, you naturally help your team become better, too. Your personal growth opens the door for others to grow.
→ Create space for others to shine
Encourage your team to take risks, learn, and grow alongside you. The more you help them develop, the stronger your whole organization becomes.
Santi’s journey reminds us that leadership is more than just running a business. It’s about the culture you create and the people you help along the way. That’s what truly lasts.
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