Behind the Stage: Q&A with LegendsNLeaders

 

The entrepreneurship journey is anything but linear. Instead, it is filled with multiple curveballs—moments of triumph, struggle, and the need to adjust your course in order to stay afloat. How do you navigate through each turning point and embrace the opportunities for personal and professional growth?

We sat down with Ben Weiss, host of the LegendsNLeaders podcast, about his experience uncovering the entrepreneurial challenges and successes with leaders across industries on the show. With 200+ episodes published to-date. Ben has sat down with entrepreneurs across growth stages to dissect the steps needed to make a positive impact across their industries.

Learn more about Ben, how the podcast has transformed, and ways to succeed as an entrepreneur, below.

Let’s take things back to the beginning! How has the podcast evolved since your very first episode?

Ben: Starting a podcast was something my family encouraged me to do, as I love meeting new people and learning about their fascinating lives and experiences. So I just started reaching out to people I wanted to speak to and we are a couple hundred episodes out, with cred supporting the growth!

I began by compiling a list of questions that I thought weren’t asked to these guests. This list was comprised from a focus on understanding the steps in their journeys that have enabled their success. With time, we have developed a format of what to ask and how to do it in a focused manner. Understanding how to move the conversation in the right direction to get these steps out has evolved!

With over 200 episodes published, what makes a great interview?

Ben: From a host perspective, a great interview is done when you ask the right questions that get a guest to talk about aspects of their journey that haven't been as visible as they should be.

You want to get insights that aren’t out there and information that needs to be shared, but hasn't come to the surface yet. With the right research, build up in the conversation, and tone, anything is possible.

(Related article: How to Be a Great Moderator)

You’ve sat down an impressive list of guests—from CEOs and Founders of companies like Fandango, Eventbrite, and Thumbtack, to household names like Howie Mandel and Kevin O’Leary. What tips have you learned are critical to succeeding as an entrepreneur? 

Ben: The top entrepreneurs and just people who make it all have one trait in common: They never gave up. After countless episodes, I have noticed that many guests take 10+ years to achieve where they are at now.

And the question is, how many people will stick at something for 10+ years with success not being guaranteed? These people have achieved the extraordinary because they have extraordinary persistence. It isn’t just luck or chance.

Favorite piece of entrepreneurial advice you’ve ever received?

Ben: The Founder of Reebok, Joe Foster, my business partner in my shoe brand Syntilay, and a LegendsNLeaders podcast guest, has given me a piece of advice that needs to be shared more in the business world: Work hard, but make sure you are having fun.

Far too often people get caught up in the motions and forget that they need to enjoy what they are doing too. Are you going to never give up at something for years if you don’t love it? No, you need to love it to have the persistence required to win.

Stay tuned for more exclusive conversations with events and podcasts! Subscribe to our newsletter for more updates to come.