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The 1 Question I Ask Every Successful Person I Meet

by Brand Post
January 13, 2026
in Business
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The 1 Question I Ask Every Successful Person I Meet
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Opinions expressed by Entrepreneur contributors are their own.

Key Takeaways

  • When I was a young entrepreneur, I set out on a mission to meet successful people and ask them one question: “What is the best advice you ever received in your life?”
  • The answers I received have not only moved my career forward, but they’ve also given me invaluable lessons about how to live a meaningful life.

I’ve always been inspired by the success of others. But I’ve also been curious about where that success comes from. What sets a person on the pathway to becoming a visionary? What sparks their belief that they can go out and change the world?

Today, I run one of the world’s most successful dialing software companies. But many years ago, I was a young entrepreneur who needed some direction. So I turned my curiosity into a sort of mission to meet successful people and ask them one simple question:

“What is the best advice you ever received in your life?”

Here are two of the most memorable answers I’ve ever received. I hope they inspire you the way they continue to inspire me.

Related: 10 Entrepreneurs Share the Best Advice They’ve Ever Received

Steve Forbes on seizing opportunities

In my early 20s, one of the people I admired most in life was Steve Forbes. He had launched countless successful publications and business ventures. I figured that whatever advice had set him on that path would also hold real value for my life. So I committed myself to finding an opportunity to meet him.

This was back in the early 2000s, and Google search was not yet sophisticated enough to help me figure out how to connect with such a prominent individual. But I eventually came across a small event in Santa Monica where Forbes was scheduled to speak.

I lived in Seattle at the time. It took every spare dollar I had in the bank to buy a plane ticket down there. But that’s what I did.

When I arrived, the room had about 100 people in it. Forbes began by speaking to the group about a book he had recently written called How Capitalism Will Save Us. I spent the next few hours listening to his advice and hearing him answer questions from the audience, wondering when, or if, my moment would arrive.

Towards the end of the night, a line formed so people could get him to sign their books. I cued up with my copy and waited my turn. When I finally made it to the signing table, I looked him in the eye and said:

“Mr. Forbes, I flew all the way from Seattle today just to ask you this question.”

Forbes glanced up. “That’s a lot of effort,” he replied.

“Well,” I said with a smile, “I’m expecting a good answer. Can you tell me the best advice you ever got in life?”

He paused for a moment.

“No one’s ever asked me that before.”

I remember thinking he must have been joking. Surely I couldn’t be the first person to ask Steve Forbes about the advice that helped him become one of the most successful people on the planet.

He folded his arms. Then slowly, he said:

“It’s gotta be what my dad told me when I was young: This isn’t a dress rehearsal.”

What he meant, he explained, was that we get one shot in life. You need to put every ounce of your effort into making sure you’re seizing the opportunities that are in front of you now, because you don’t get a second take.

Ironically, I was already following Forbes’s advice when I bought that plane ticket. If I had let the opportunity pass me by, our paths might never have crossed, and he never would have reinforced my belief in the value of taking risks to achieve your goals.

As you can imagine, this belief has served me well throughout my life and career, especially as a CEO, where success demands action and comes down to inspiring others to take their own shot. But the best leaders don’t push people to act; they help them bring their best selves forward. I saw that lesson come to life years later, in a conversation with NFL coach Pete Carroll.

Related: 5 Risk-Taking Lessons From Founders Who Bet Big and Won

Pete Carroll on staying true to yourself

Pete Carroll is a coach, most recently for the Las Vegas Raiders, my all-time favorite football team. Years ago, I decided to sign up for a coaching clinic he was running, despite the fact that I am neither a football player nor a coach. Even at 6’4″ and 220 lbs, I was one of the smallest guys there. Not that it mattered; I wasn’t really there to learn football. I was there for the Q&A.

As soon as the questions started, my arm was up in the air. Everyone around me was asking questions about plays, formations and strategy. But when it was my turn, I asked Carroll the same question I had asked Forbes at his book signing.

This time, I got an answer immediately. Without skipping a beat, Carroll said to me:

“The best advice I ever got in my life was to be myself.”

He continued. “When I try to be someone I’m not, things don’t end up working well for me. You need to know who you are. Obviously, we all want to improve, but you shouldn’t try to be someone else. Try to be the best version of yourself.”

Carroll’s advice stuck with me because it was simple but deeply human: You can’t lead or live effectively if you’re pretending to be something you’re not.

That perspective has shaped how I try to show up as a CEO. The best results come from helping people lean into what makes them great. When people feel free to be themselves, they show up with passion and do their best work. It’s a lesson I still carry with me today.

Related: Training To Be The Best Version Of Yourself: The How-To

How asking for advice has changed me

The advice I got from Forbes, Carroll and others has done more than move my career forward. It’s given me invaluable lessons about how to live a meaningful life.

Forbes’s answer taught me to seize opportunities, even when the path wasn’t certain. Carroll’s answer taught me to stay grounded in who I am while doing it — a mindset that’s shaped everything from PhoneBurner’s Responsible Communications™ initiative to how I approach fatherhood and family.

Those lessons have a way of resurfacing, often at moments that remind you what really matters.

A few months ago, I found myself writing my mother’s obituary. As I reflected on her life, I realized that a eulogy is not a LinkedIn profile. It’s not a summary of titles, milestones and accomplishments. It’s a story about the things you love most and the risks you’re willing to take for them.

In other words, life isn’t a dress rehearsal. You only get to do it once, so you’d better do it in a way that honors your passion and your unique gifts. One simple question gave me that perspective — so you’d better believe I’ll keep asking it.

Key Takeaways

  • When I was a young entrepreneur, I set out on a mission to meet successful people and ask them one question: “What is the best advice you ever received in your life?”
  • The answers I received have not only moved my career forward, but they’ve also given me invaluable lessons about how to live a meaningful life.

I’ve always been inspired by the success of others. But I’ve also been curious about where that success comes from. What sets a person on the pathway to becoming a visionary? What sparks their belief that they can go out and change the world?

Today, I run one of the world’s most successful dialing software companies. But many years ago, I was a young entrepreneur who needed some direction. So I turned my curiosity into a sort of mission to meet successful people and ask them one simple question:



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Tags: AdviceEntrepreneursGrowth StrategiesLeadershipMeetPersonQuestionSuccessSuccessful

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