Leadership Journeys [225] - Lamar J Romero - " The entrepreneurial journey is about leaving some kind of a mark on the world"

Choosing Leadership with Sumit Gupta

This is the Leadership Journey series on the Choosing Leadership Podcast.

I believe we all have a lot to learn from each other's stories - of where we started, where we are now, and our successes and struggles on the way. With this series of interviews, my attempt is to give leaders an opportunity to share their stories and for all of us to learn from their generous sharing. If you know a leader whom you would like to see celebrated on the show, please send me a message on LinkedIn with their name.

What does it really take to walk away from comfort and step into the unknown as a leader?

In this episode, Lamar J Romero, founder and CEO of Hire Dragons, shares the gritty truth behind building a business from the ground up—Uber rides, failed experiments, and all.

He opens up about the internal battles every leader faces, especially the constant tug-of-war between comfort and greatness.

If you’ve ever wrestled with self-doubt, growing pains, or the pressure to scale without losing your soul, this conversation will hit home.

Tune in for a refreshingly honest take on leadership, resilience, and choosing impact over ego—every single day.

You can find Lamar J Romero at the below links

https://www.linkedin.com/in/lamarromero/
https://www.linkedin.com/company/hiredragons/

In the interview, Lamar shares

• “true leadership isn’t given; it’s chosen every single day.”
• “i quit my comfy dell gig to promote tequila—because leaving a mark beats playing it safe.”
• “when your bank account says no, your determination says go—uber, lyft, bootstrapping: that’s the grind.”
• “mix tech with hustle—that pivot is what took hire dragons from idea to impact.”
• “covid didn’t break us; it made us adapt faster and lead more authentically.”
• “the real battle in leadership is comfort versus greatness—i pick greatness.”
• “leaving a monument isn’t about billions; it’s about building teammates up to win.”
• “in our culture, mistakes aren’t failures—they’re experiments to level up.”
• “after 12 years, i’m not slowing down; i’m doubling down on service through investing and advising.”
• “choice is the cornerstone of entrepreneurship—decide to lead, decide to leave a legacy.”