Welcome, Santi
Welcome entrepreneurs. I’m so glad to have you here. And welcome to our new subscribers who found us through last week’s semi-viral issue, a user’s-guide to the midlife reorientation.
Building Inside-Out Leadership has been such a joy, and so different from any of the other companies I’ve built. While previously I’d craft a compelling vision, and then kill myself wrenching reality to conform to it, with I-O I’ve let go of the idea of having a vision to build toward, and instead focused on simply doing the best work I can, each day.
Well, as it turns out, when you do that you allow for the Universe to support your work in serendipitously awesome ways. This has happened so many times on this journey.
And again today.
I’m excited to announce that 3x founder turned coach, Santi Jaramillo, is joining Jason, Julie, Kat and me on the I-O team.
Santi is a 3x founder (companies worth over $100m) and a bestselling author. More importantly he is an outstanding leader and human, with valuable wisdom, hard won, that will add to I-O’s capacity to support founders looking to step fully into their lives and build their companies into their masterpieces.
I could go on, but I’ll leave it to Santi to introduce himself.
Welcome Santi!
My story spans two continents, several startups, and years of self-work. And it almost took a very different turn. Some decisions are inconsequential. But others change the trajectory of our lives forever.
I discovered my knack for entrepreneurship early. As a kid in Cali, Colombia, I sold Coca Cola water jugs out of my prized red wagon and avocados to my parents’ friends. That was my first taste of the satisfaction that comes from doing something I enjoy and am good at. And having money to buy myself candy wasn’t so bad either.
Even as a young kid, I still felt something was missing. In Colombia, the adults around me worked for survival. But I always knew I wanted more. Some deeper purpose or vision for positively impacting the lives of others. This longing planted a seed within me.
Then one seemingly small decision changed everything.
The 90’s in Colombia were a time of political unrest and violence. One ordinary Sunday, I begged my mom to let us skip mass. My brother and I had been helping my dad build a treehouse, and we were so close to finishing it. She reluctantly agreed. An hour later, we heard gunshots. The ELN, a Marxist-Leninist guerrilla group, had stormed the church and kidnapped more than 100 hostages, many of whom were held for more than a year.
Shaken, my parents hastily made plans to immigrate to the United States.
A decade later, after enduring the hard work of assimilating to a new culture and language, my childhood longing to build something meaningful manifested. I started Bluebridge from my college dorm room—a SaaS mobile app company for churches, tourism bureaus, and universities.
I spent my early 20s growing Bluebridge from a one-person startup to a team of 50, picking up some venture capital and a handful of awards along the way. It was in building the culture and team that I realized the power work has on our ability to thrive. Work can be an incredible catalyst for personal growth or a devastating force of ill-being that ripples out to the people around us.
So in 2016, we made the decision to sell off our church and tourism business units and pivoted to building employee engagement software as Emplify. Our team was growing quickly, and the demands of the business mounted by the day.
Entrepreneurship—especially the venture-backed, hyper-growth kind—is intense and unrelenting. It is filled with unimaginable highs and devastating lows (sometimes in the same day). As the business demanded more of me, I found my mental health and mood were largely dictated by our performance. When people asked, “How are you?” I would mentally pull up the dashboard of our annual recurring revenue goals for that quarter. The numbers dictated how I felt.
On the flip side, I noticed my own psychology getting in the way of my ability to lead. I pushed myself way too hard from a place of fear, working to the point of total exhaustion that just led to lower-quality decisions and interactions with people. I gripped outcomes too tightly. I didn’t cut myself or the team any slack when we made mistakes. I often found myself responding to people from a place of triggeredness, rather than centeredness. And in merging my identity and state of mind with the state of the business, I started to lose myself.
My wakeup call came when my co-founder quit.
When I dug into why, it became clear that the reason wasn’t the organization, the mission, or the team. It was me. As a leader, I was not growing as fast as the company needed me to grow. I was so focused on results that I had lost sight of the people I was asking to produce them. And that was causing damage.
During the next several months, I looked inward. I realized my deepest longing was equanimity. I wanted peace, joy, and vitality regardless of business circumstances, so I set out to pursue it. I attended a Reboot.io CEO bootcamp where, for the first time, I was around other successful founders who were willing to take their masks off and be vulnerable about the immense difficulties of the journey. I hired a coach who helped me become aware of my triggers and deal with them in more productive ways.
In the pursuit of becoming a better leader, I actually became a better human.
My journey as a founder and CEO came to an end in 2021 when 15Five bought Emplify. In 2022, I took a much-needed sabbatical to rest, heal, recharge, and figure out what I wanted to do next. With open time and a spacious schedule, I found myself once again wanting work that I enjoy, am good at, and makes a positive difference in the world.
Coaching founders and senior leaders is that for me.
I love working with founders in transition—clients who are going through a change in their work or lives or whose companies are growing quickly or both. I also am passionate about supporting CEOs as they ride the ups and downs of leadership and creating space for them to find more equanimity and more authentic, sustainable performance. Finally, I love helping CEOs get to know themselves and their zones of genius, so they can be more effective and surround themselves with the right teams.
I’m deeply dedicated to helping my clients pursue artistry and excellence in all aspects of their lives—leading themselves and others with more clarity, authenticity, and confidence.
If Santi’s story resonated with you, please reach out to him directly at: santi@leadinsideout.io
Want to dive deeper?
If you liked this, check out this list of my top posts, read and shared by thousands of entrepreneurs.
Here are a few of my favorites:
The secret to leadership (why authentic leadership is simply more effective)
How to pitch a big vision to investors without setting yourself up to let people down
Executive Coaching for Entrepreneurs
There’s a reason every elite athlete in the world works with a coach. You need more than one perspective to see your best work.
I’m an executive coach and the founder of Inside-Out Leadership, a boutique leadership development agency that supports entrepreneurs to step fully into their lives, and transform their companies into their masterpieces.
Leveraging 15-years as a founder/CEO, along with deep training in mindfulness, psychology, Neurolinguistic Programming, psychedelic integration and more, I have helped leaders from some of the fastest growing companies and VC funds in the world design a more conscious life and make key changes to improve their performance and satisfaction.
I coach leaders how I want to be coached:
Focused on the person, not the role.
Focused on results, without the fluff.
To learn more about working with me, click here.