THE GIFT OF STRUGGLE with Bobby Herrera

Audio production by James Ede, Be Heard

Today, we start Season 4 of the CultureLab podcast and our first guest this season is the CEO and Founder of Populous Group, Bobby Herrera.

Bobby is a huge advocate for the underdog – anyone who has found themselves on the wrong side of the opportunity divide. He built his company to elevate people who are no stranger to struggle.

When it comes to struggle, Bobby has his own philosophy. He believes that every leader had to overcome the challenges and struggles that required strength, patience, perseverance, and courage. And it’s because of these difficulties, not in spite of them, that we become better leaders. He expands on this idea in his book, The Gift of Struggle: Life-Changing Lessons About Leading.

What was interesting for me to learn in this interview was that Bobby hasn’t always been the leader he is today.

At some point, he realized that the person who showed up at the office was a less engaged version of him. He wasn’t proud and decided to do something to change it.

Tune in to hear Bobby talk about the pivotal moment that transformed the way he showed up as a leader and how he inspired his employees with his vulnerability, radical transparency, humility, and the idealism of his dreams for the company.

Episode Highlights

Here are some of the themes that we explore:

  • An act of kindness that changed Bobby Herrera’s life
  • Why Bobby places such great emphasis on behavioral alignment in his team
  • The most important metric you should be paying attention to if you want a successful business
  • The ups and downs of an entrepreneurial journey and why they are all necessary for our growth as leaders
  • The importance of articulating and sharing our why and vision with the people on our team
  • What the real gift of struggle is
  • What the E in CEO stands for in Bobby’s view
  • A leader as a storyteller – and where to look for the best audience to test your stories with
  • How Bobby Herrera thinks of a healthy culture
  • Cultivating psychological safety

Listen to the interview in the player below or on iTunes. If you like what you hear, please leave a review, and it may be featured on a future episode.

Audio production by James Ede, Be Heard

More about Bobby Herrera

As one of thirteen children in a migrant family Bobby learned the value of hard work, rising early and putting in long hours in the fields. After high school, boot camp became his ticket of opportunity.  He serves on national community organization boards and is a regular speaker at corporations and service groups. He is a proud Army veteran.  Bobby is most proud of his family—his wife Roslyn and their three children Santino, Griffith, and Sofia live in Portland, Oregon.

You can find out more about Bobby here:


Populus Group



Books Mentioned in this episode

The Gift of Struggle: Life-Changing Lessons About Leading by Bobby Herrera
The Advantage: Why Organizational Health Trumps Everything Else In Business by Patrick Lencioni

Additional resources

What Can COVID-19 Teach You About Your Company Culture?

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