As living, breathing professionals, we’re often bound to repeat our past mistakes. That’s one of the reasons looking back through history is so important—it’s a substantial way to prevent the repetition of past mistakes, and the knowledge gained can be advantageous moving forward.

The problem with business today: there is no finite path you can follow to mirror the success of others—each path is different, each path leads down a different road.

And it’s a hard path to follow. But, what we can do is learn from them—the successful, influential CEOs of the past and present—their values, their motives, their cathartic moments, and use that as our own jumping off points.

→ Download Now: Free Business Plan Template

Understanding how they got to where they are today can mean all the difference to your own business, and hopefully these inspirational quotes from the top CEOs of the modern business world will set you on the path you’ve been looking for.


1) Drew Houston, Dropbox Co-founder & CEO

“Don’t worry about failure; you only have to be right once.”

As a culture, we’ve learned to reject failure, but sometimes we need to relish failure because each circumstance is just another lesson on what to do the next time around to ensure success. As Drew Houston said, you only need to be right once, and sometimes we get there by accident—but it was our previous failures that got us to this point. Sometimes failure is a door to a breadth of exciting new opportunities. Don’t let it shut.  

2) Howard Schultz, Starbucks CEO

“In this ever-changing society, the most powerful and enduring brands are built from the heart. They are real and sustainable. Their foundations are stronger because they are built with the strength of the human spirit, not an ad campaign. The companies that are lasting are those that are authentic.”

This ideology is booming these days, and for good reason. Consumers want companies to be transparent in their mission, vision, and operation practices. And the ones that are sincere, the ones that take their time to provide their customers with what they’ve been asking for are the ones that will stand the test of time. Remember: passion fuels desire.

3) Steve Jobs, Apple CEO

“You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something—your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.”

You could fill a book with Steve Jobs’ inspirational quotes alone—but this one is my favorite. It’s a different approach on the “hindsight is 20/20” idiom, but with the added take on finding something to believe in. If you don’t have a stake in the purpose of your company, how can you expect your customers to? Forge your path with goals in mind, and when you look back on your life, you’ll be able to say you took charge of your own destiny.

4) Donald Trump, The Trump Organization CEO

“Experience has taught me a few things. One is to listen to your gut, no matter how good something sounds on paper. The second is that you’re generally better off sticking with what you know. And the third, is that sometimes your best investments are the ones you don’t make.”

The Donald: no matter how you feel about his ridiculous reality television excursions, the man knows how to build a successful business empire. Intuition is a powerful sense, and if you’ve been in the business as long as Donald Trump, trusting your gut is a vital commodity.

All three of his rules reflect this line of thinking, and there’s a lot of truth behind it. The decisions you make are rarely black and white—you need to learn to relish the grey, and go with what you think will be best for you and your business in the long run.

5) Kevin Plank, Under Armour CEO

“There’s an entrepreneur right now, scared to death, making excuses, saying, ‘It’s not the right time just yet.’ There’s no such thing as a good time. I started an apparel-manufacturing business in the tech-boom years. I mean, come on. Get out of your garage and go take a chance and start you business.”

There will always be a reason not to do something, whether it’s money, family, or timing—but none of them are good enough reasons to bring your vision to a halt. As Kevin Plank explains, there’s never a good time, and waiting for it is a waste. Instead, learn to take a risk on something you believe in.

The worst-case scenario? It doesn’t work, and you can move on to your next great idea. Some of the greatest brands in the world were built on the backs of accidents. Don’t miss your chance because you’re scared to start.

6) Cher Wang, HTC CEO

“It takes humility to realize that we don’t know everything, not to rest on our laurels, and to know that we must keep learning and observing. If we don’t, we can be sure some startup will be there to take our place.”

No one knows everything. And no one should be expected to. There’s this idea out there, especially for the younger generation of workers, that professionals today need to know everything—but real knowledge is understanding that you can’t know everything.

We’re always improving, and the second we think we can stop is the second we need education the most. As Cher Wang says, if you won’t make the effort, someone else will. Business is constantly changing, and if you want to stay at the forefront, you need to do the same.

7) Larry Page, Google Inc. CEO

“Lots of companies don’t succeed over time. What do they fundamentally do wrong? They usually miss the future.”

Similar to businesses thinking it’s okay to take their foot off the gas pedal, many brands get stuck in archaic business practices, ultimately hurting their company through their own means and misconceptions. The future doesn’t need to be scary, just as much as it doesn’t need to signal widespread organizational change in your business.

But they can’t keep referencing the past if they want to be successful in the future. Spinning your wheels needlessly isn’t an option, so utilize what you can (in both technology and culture) and future proof your business practices.

8) Denise Morrison, Campbell Soup Co. CEO

“The thing that I learned early on is you really need to set goals in your life, both short-term and long-term, just like you do in business. Having that long-term goal will enable you to have a plan on how to achieve it. We apply these skills in business, yet when it comes to ourselves, we rarely apply them.”

Denise Morrison has dreamed of running a business since she was a child. In fact, her siblings are also business leaders, so she knows a thing or two about setting goals. But often, we focus too narrowly on our work, and not enough on improving our selves.

A rising tide lifts all ships, and if you want your business or organization to improve, you should start with the people within it. Push yourself to improve on a personal level, and you may see the fruits of your labor in your next sale, meeting, or project.

9) Indra Nooyi, Chairperson and CEO, PepsiCo

“The distance between number one and number two is always a constant. If you want to improve the organization, you have to improve yourself and the organization gets pulled up with you. That is a big lesson. I cannot just expect the organization to improve if I don’t improve myself and lift the organization, because that distance is a constant.”

As a business leader, your job is to portray the qualities your employees and coworkers strive endlessly to replicate. Setting the right example is paramount if you want your business to follow in your footsteps. But if you want your company to follow you, you need to set the same expectations for yourself. Successful business leaders understand this, and their business cultures reflect this sentiment in every office or work environment.

10) Brian Halligan, HubSpot CEO

“The way I think about culture is that modern humans have radically changed the way that they work and the way that they live. Companies need to change the way they manage and lead to match the way that modern humans actually work and live. We’re trying to re-craft culture in a way that really matches that. I think that 99% of companies are kind of stuck in the ‘90s when it comes to their culture.”

Culture infiltrates every nook and cranny of your company. It affects productivity, efficiency, happiness, success, and everything in between, yet companies too often brush culture under the rug.

Collaboration and communication are at the forefront of the modern office, and with technology changing the business landscape so frequently, you’re being tasked with playing catch-up with every twist and turn. You can’t expect someone to work like they have in the past after the past becomes irrelevant.

11) Jake Nickell, Threadless CEO

“I try not to make any decisions that I’m not excited about.”

Business decisions should never be boring. You’re either excited about them, or you’re not. Putting yourself behind an idea can be a daunting task, but if you’re willing to put in the effort, you should be excited to see the outcome.

Jake Nickell started Threadless with $1,000, and transformed it into one of the leading custom art ecommerce sites on the market—and how’d he get it there? Passion. Excitement. And a little dash of color.

Business Plan Template

 New Call-to-action

Originally published Aug 18, 2014 2:00:00 PM, updated January 18 2023