Summit of Greatness 2025 Early Bird Now Open! | September 12-13 | Los Angeles, CA
I want to start the podcast with this quote from Estée Lauder: “I never dreamed about success — I worked for it.”
There’s a perpetual question out there of whether people are born successful or if they work for it. Are successful entrepreneurs naturally that way? Or do they work their way up to the top?
On The School of Greatness, I’ve had so many successful entrepreneurs share their stories with you all — and the majority of them did not begin with success. In fact, many of them started with failure.
But what set them apart is that they didn’t quit. Despite the failures, the self-doubt, and criticism, they pushed through and worked hard to make their dreams come alive. And it wasn’t just about the money for these entrepreneurs — they all had a mission, and they held fast to that mission as their guiding light.
My guest today, Guy Raz, has been studying entrepreneurs for several years. You may know him as the voice of the incredible podcast How I Built This on NPR. I was so excited to have him on The School of Greatness to give his insight on the world of entrepreneurship and what sets successful entrepreneurs apart.
Guy Raz is the host, co-creator, and editorial director of three NPR programs, including two of its most popular ones: TED Radio Hour and How I Built This. Both shows are heard by more than 14 million people each month around the world. How I Built This is a podcast about the greatest innovators, entrepreneurs, and idealists, and the stories behind the movements they built. In each episode, the founders of some of the world’s best-known companies and brands take us through their triumphs, failures, and insights. I highly recommend checking it out if you haven’t already!
As a host and correspondent, Guy has interviewed more than 6,000 people including Richard Branson, Kelly Clarkson, Christopher Hitchens, Condoleezza Rice, Mark Cuban, Jimmy Carter, Al Gore, Mark Zuckerberg, Bill Gates, Roxane Gay, Eminem, Taylor Swift, and many, many others.
And now, Guy is coming out with a new book: How I Built This: The Unexpected Paths to Success from the World’s Most Inspiring Entrepreneurs. He has distilled all the wisdom he’s learned from these amazing entrepreneurs into a valuable resource for anyone aspiring to build a business or who is interested in the process!
In our interview, Guy and I covered some fascinating topics, including the key skills that set entrepreneurs apart, the importance of focusing on mission instead of money, and what you can learn from failure. This is an interview you’re not going to want to miss, so get a pen and paper ready to take some notes!
Great entrepreneurs come from everywhere. Some of them are extroverted, charismatic salespeople, and others quietly do what they do best from behind a podcasting microphone or a website. Entrepreneurs have a variety of skills, personality traits, and passions. But according to Guy, they all have one thing in common: the ability to handle rejection.
“The one thing that binds every person I interview is they all either have naturally or have learned to develop the ability to withstand rejection, to basically accept that lots of people are going to say, ‘no,’ and keep … grinding.” – Guy Raz
For a great example, Guy mentioned Tope Awotona, the founder of the scheduling tool Calendly. Today, he’s an incredibly successful businessman with a product that countless people — me included — use for their businesses. But before he was successful, Tope was a 16-year-old kid from Nigeria going door to door in Athens, GA selling ADT home monitoring systems. He had doors slammed in his face thousands of times, but he never got discouraged because he knew he’d eventually find someone who wanted to buy what he was selling. He overcame a ton of rejection because he knew that just one success would be enough to win.
And here’s the good news: The ability to overcome rejection is a learned skill. That means anyone can acquire it, and anyone can be a successful entrepreneur. For another great example, Guy talked about the Mormon church and their practice of having 18-year-olds spend two years out on mission for the church. Mormons develop independence and the ability to withstand rejection at a young age by having a thousand doors slammed on them just to get five or ten people to convert. They get used to rejection early in life, and as a result, Mormons have a much higher percentage of successful entrepreneurs than other populations.
So how can you and I overcome the fear of rejection? Guy says it’s all about looking at the bigger picture.
“There’s a really famous professor at Harvard named Ron Heifetz [who] teaches a course on leadership. He has this concept where he basically looks at successful and highly effective leaders, and basically what they do is they’re able to kind of step out of their own bodies and stand on a proverbial balcony and look down at themselves in the situation they’re in.” – Guy Raz
Next time you find yourself facing rejection, try to step outside your own head, and look at the bigger picture. Did one person reject you? Yes. But does that mean your idea or product or service is a total failure? Of course not! It’s a challenging skill to acquire, but if you can look at the broader picture and realize that rejection does not mean failure, you can tweak your sales technique as needed and keep moving forward.
Here’s the bottom line: If you’re focused on your mission and not just the money, you will be able to withstand rejection and succeed as an entrepreneur. There’s nothing wrong with pursuing money as well, but you have to fundamentally believe in your product or service to overcome countless rejections and be successful.
At the end of the day, you only need so much money. It’s great to build a successful business and achieve the wealth you’ve worked for, but at a certain point, you really don’t need more money to be happier.
“Stewart Butterfield, the founder of Slack, has a great explanation for what it means to be wealthy: You can go to a restaurant [and] order anything you want, you can basically go on vacation wherever you want, and you’re not worried about debt. … Basically, his argument is once those are taken care of, you are essentially wealthy.” – Guy Raz
If you can order whatever you want at a restaurant, take vacations wherever you want to go, and not be worried about debt, do you really need more money? At that point, you’re wealthy and comfortable, so if your business gives you that opportunity, you’re successful. And according to Guy, many people eventually get bored when they make more money than that anyway.
“I think a lot of people imagine that you have a company and then you sell it, and then you’ve got a hundred million dollars and then you’re going to go lie on a beach in the Caribbean and sip Piña Coladas all day, right? The reality is if you did that, you would eventually become very depressed. … Most of the people I’ve interviewed, they want to work until the very end, … even when they have enough money for three generations behind them because it isn’t about the money.” – Guy Raz
Successful entrepreneurs are driven by passion, not just a desire for wealth. They want to work because they know that they’re providing something that impacts the world and makes it a better place for all of us. They thrive on the connection, comradery, and sense of purpose that comes from working with a team and with customers to build their businesses, and they wouldn’t want to give that up no matter how much money they made!
Even if we can learn to overcome rejection and power through based on our faith in our mission, there’s still a strong fear of failure for a lot of aspiring entrepreneurs. But here’s the thing: Success is not the end of any business endeavor.
“The reality is that success is not an endpoint. It’s not like you do something and then you wake up, and you blow the trumpet and say, ‘Dah dah dah dah! I’m successful!’ and that’s it.” – Guy Raz
It’s true — there’s never a specific point where you’re officially succeeded or failed. Guy compared it to exercising. You can work out every day and be an extremely fit and healthy person, but there’s never a point where you’ve succeeded, you’re healthy enough, and you can quit. You have to keep going, keep trying, and keep working to stay in top condition.
And the truth is, even when you do experience failure, that can be the thing that propels you into your next endeavor. There are countless stories of highly successful people who experienced failure, got back up, shifted their technique or mindset, and kept working.
“I think failure is just infinitely more interesting than success. … That’s really where people are at their most generous — when they’re really … talking about their failures. And it allows us to … get a window into their soul that we need to have to help us when we are struggling with failure.” – Guy Raz
Think about your business role models — They all experienced failure at some point. But they didn’t let failure defeat them. They kept hustling and grinding until they achieved their dream, and I want to encourage you to do the same. You are capable of overcoming failure, so don’t let that fear keep you from trying! Strive toward your dream, and be willing to forgive yourself and learn from your mistakes. That’s how you’ll grow and one day share your interesting story — perhaps on How I Built This or right here on The School of Greatness!
This episode is required listening for anyone out there who has a dream of being an entrepreneur! Guy Raz has so much more wisdom to share, and this post barely scratches the surface of all the wisdom he brought to our interview. I want to acknowledge Guy for constantly hustling to bring the world inspiring stories and practical wisdom to help entrepreneurs succeed and accomplish their dreams.
Guy really lives up to his definition of greatness:
“My definition of greatness is making sure that the people that you have the power to influence, inhabit, and live on this planet with kindness and a sense of responsibility. … I have one purpose: It is to, as best I can, instill … the values that I think are important, that I hold dear … in my children. … If they grew up and they are kind and responsible and good humans like that, I’ve done my job.” – Guy Raz
I love that definition. If we all strive every day to live by our values and treat one another with kindness and respect, we make the world a better place every day.
Thank you so much for joining me on this episode, friends! This conversation was so inspiring to me, and I hope it was for you too. If you’re ready for more of Guy’s fantastic content, definitely check out his podcast on NPR, How I Built This. You’ll hear so many inspiring stories from successful entrepreneurs. And don’t forget to check out Guy’s upcoming book, How I Built This: The Unexpected Paths to Success from the World’s Most Inspiring Entrepreneurs. I know it’s going to be full of wisdom and practical knowledge, and I’m definitely looking forward to reading it!
If you learned as much from this episode as I did, please share it with your friends on Instagram! Tag Guy, @guy.raz, and me, @lewishowes, and share your biggest takeaways from the episode. We’d love to hear from you!
Thanks again for joining me today, guys. I’ll talk to you guys later.
To Greatness,
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