Ideas | December 5, 2025
Grit and Resilience: The Hidden Traits Behind Every Great Entrepreneur
By: Pennebaker Staff

People often glorify entrepreneurship because most of the time, they only see what’s on the outside. I mean, having your own company sounds cool. Setting your own hours is often the dream for many. And leading a team that believes in your vision? Now that feels empowering. 

But what happens when your company is in a “dry season” and you keep digging dry holes? Or when your career leaves you with more working hours than a traditional 9-5? And don’t forget all those times people didn’t believe in your vision and counted you out? 

Business ownership has its many perks, but there are often more times than not when you’re sitting with your head in your hands, uncertain of what tomorrow looks like. But that’s where grit and resilience come into play. That’s what separates a good business owner from a great entrepreneur.

Our guest this week, Brian Reinsborough, has had a highly successful career with many wins under his belt. But he also knows what it’s like to feel defeated. Despite isolated points of failure, what keeps him going is his relentless drive for performance-driven leadership and unwavering belief in betting on himself when the odds are stacked against him. 

In this conversation, Brian shares how tenacity and fortitude shaped his journey from coming up empty to billion-barrel discoveries, why holding yourself and your team to the highest standard is non-negotiable, and how embracing uncertainty can lead to your greatest breakthroughs. His story is one of perseverance, vision, and the courage to lead differently. 

Listen to the full conversation on Spotify - 

Brian Reinsborough on Rethink Change

Brian Reinsborough, Visionary, President and CEO of ReconAfrica

A visionary executive with over 35 years of experience, Brian Reisenburough has established an exceptional record of strategic, leadership, and management success across the energy industry. But you don’t get that from playing small. 

Throughout his career, he has developed and executed multiple business plans, including the launch of two Deepwater ventures in the Gulf of Mexico that have grown into industry-recognized programs. His expertise and forward-thinking leadership have resulted in the discovery of over 2.4 billion barrels of oil equivalent (BOE), shaping the future of exploration and production in some of the world’s most challenging environments. 

Brian Reisdenburough holds a PMD from Harvard Business School, an M.S. in Geology from the University of Texas at Austin, and a B.S. in Geology from Mount Allison University. A finalist for the EY Entrepreneur of the Year National Award in 2014, he has also successfully raised more than $2.5 billion in private equity funding, fueling innovation and growth within the sector. 

Brian’s career is defined by his rare combination of scientific expertise, business acumen, and visionary leadership that continues to leave a lasting impact on the industry. 

His secret? Having the drive to push through uncertainty, bouncing back from adversity, and betting on yourself even if you’re the only person in the room. 

Entrepreneurship: Trailblazing Into New Territory

People love a good inspirational quote or a framed affirmation hanging in their office. The term “trailblazer” is a feel-good title leaders use when embarking on new goals. But what does it actually mean to trailblaze into new territory? Well, the truth is, most entrepreneurs will tell you it feels a lot less glamorous when you're in the weeds. In fact, it feels a lot more like “bushwacking”. 

To be a trailblazer, you must navigate a great deal of uncertainty, not only for yourself and your family. When you have a company that relies on you, there’s an added level of responsibility. 

Sometimes stepping into new territory looks like long nights, questioning your decisions when everyone’s looking to you for answers. There are moments when you have to silence the noise and fight the “what ifs” when things begin to look bleak. Because behind closed doors, true entrepreneurship is demanding and often feels isolating.

Why Failures are Jumping Off Points, Not Stumbling Blocks

And yet, that’s often where many stop short. When things feel too challenging, they bounce to something else. But when it comes to trailblazing into new territory, the goal isn’t to walk down the path that’s already been paved for you. It’s about having the courage to try something new. It’s about creating your one map to success, not following someone else's. 

Yes, there are guidelines to help you stay on track. But sometimes finding success is about trying a different approach. Take the “road less traveled”. Or better yet, creating a different pathway. And also yes, there will be challenges ahead. In entrepreneurship, failure is inevitable. But the difference between those who lead successful careers and those who get left behind in the dust? How you respond to those failures. 

For Brian, these moments of digging dry holes were only learning curves, not dead ends. They were jumping off points to redirect his path, not stumbling blocks designed to stunt his growth. It was the grit and resilience that shaped his career. 

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Love hearing how fearless leaders like Brian Reinsborough let their grit and resilience guide them in making tough decisions, even when they didn’t know what was next in their career? His story is sure to empower the next generation of entrepreneurs who refuse to give in times of hardship because they know their vision is bigger than any minor setback. 

This episode of Rethink Change explores what it truly means to trail-blaze into uncharted territory, how to set your team up for success, why investing in yourself is crucial, and how to transform failures into fuel for growth. 

Whether you’re a seasoned executive, an entrepreneur deep in the trenches, or looking for motivation to keep pushing through tough challenges at work, this one’s for you. To hear more stories like this one, be sure to subscribe to Rethink Change, where innovators and disruptors go for clarity.

This show is hosted by CEO Ward Pennebaker and President Matt Pennebaker, who deliver sharp insights from battle-tested leaders who have navigated chaos and turned challenges into momentum.

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