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Tech Industry Pioneer Jean Case on How to Change the World With Your Big Idea 'Why is it, as people chase opportunities or challenges, sometimes they break through and sometimes they don't? And could there be a special sauce behind that?'

By Hayden Field

entrepreneur daily
Paul Zimmerman | WireImage | Getty Images

"Why is it, as people chase opportunities or challenges, sometimes they break through and sometimes they don't? And could there be a special sauce behind that?"

Those are the questions tech industry pioneer Jean Case asked herself as she gathered the material for her new book, Be Fearless. Besides Case's position as CEO of The Case Foundation, which she co-founded with her husband Steve, she's also chairman of the board of trustees for The National Geographic Society -- and, of course, formerly a senior executive at AOL. During her time in the impact investing space and her work at the Foundation, Case has heard a wide array of business ideas, both big and small. In this episode of Entrepreneur's How Success Happens podcast, she shares strategies for how to gauge whether your big idea can go the distance, how to expertly pitch to friends, family and investors and how to take a calculated risk. She also weighs in on how large tech companies may handle data privacy down the line. To hear the full interview, listen here or via the player at the bottom of this page.

This interview has been edited for length and clarity.

Two of the key principles in Be Fearless center on making a "big bet" and taking bold risks. But I'm sure a lot of our listeners are wondering -- especially if they've got limited capital and are considering quitting their day job -- how do you take a calculated risk?

That's a really good question, and I must say that the very first chapter is titled "Start Right Where You Are." It's a storytelling book, so although it's the five principles we really try to tell stories to illustrate how these principles can be applied or have been applied for people who have found success. The idea of starting right where you are is almost taking an audit of your strengths and what you have to start with. I'll give you an example. We open the book with a woman who was a sole practitioner, a mental health counselor, and she saw a challenge across the nation of military veterans facing mental health challenges. She asked friends to donate an hour a week pro bono, then turned it into a nonprofit in the form of a national network of doctors around the country. Today, there are thousands of doctors that provide many millions of dollars in free mental health counseling to veterans and their families. I think her story is important because even though it's not a for-profit company, any entrepreneur can see the entrepreneurial spirit alive there.

You've done great things in the tech space with AOL, the Case Foundation and a host of other organizations, and I know you're passionate about using tech to make the world a better place. What's the most important thing to remember in the current landscape, as tech companies become more and more evolved and collect greater amounts of data?

It's funny; there are a lot of challenges that we face around tech and whether, in the end, it's best serving consumers and the population more broadly. But I'm still super optimistic about the power of tech to change lives.

When we started AOL, we were on a mission to democratize access to ideas, information and communication, and I still think that's a brilliant mission. We still need to work on it because not everybody has access today. But it's quite possible that we can chase all these exciting new ideas with tech and still embrace an ethos of ethics where basically we're asking ourselves questions along the way: Does this best serve a population? How could it be turned and used for evil? What might we build into products and services, or even guidelines and frameworks around how we run our companies, to make sure that we're keeping those things in mind? Particularly leaders -- the entrepreneurs and founders -- must convey that ethos, that they care about doing good and care about making sure that their products and services are being used for public good.

Now that more and more tools are coming out to help monitor and limit our time spent on screens, what do you think our device use will look like in five years?

When restaurants started putting the number of calories per item on their menus, I think they believed that would change consumer behavior, and I don't know if it has. It would be interesting to see a report on whether knowing the extent of your screen time does influence how much you use your device. But I also believe that I've seen the pendulum swing. We're coming out of a period where people are in crosswalks looking at their phones, at dinner with each other looking at their phones. I think the pendulum is going to swing back and people are going to realize the best life is one where you're fully engaged in the moment. We'll hopefully start to see some of these devices as tools and resources to aid our lives and maybe aid our work but not for 24/7 use like they've become.

You're widely known as a pioneer in impact investing. What's your best piece of advice for founders who hope to pitch their idea to investors, friends and family so that it truly stands out?

Often, when I'm listening to someone pitch his or her company, what I'm really listening for is: Are they being as bold as they can be to take a really big idea forward? Being able to communicate the idea is really most important, and particularly in something like a pitch competition where you have to do the elevator pitch, you have to be crisp about the big idea. You really have to know what it is that you want to convey. You might believe in your idea, but you have to understand that others aren't steeped in it like you are. And perhaps most common, when I judge pitch competitions, I think entrepreneurs can be reluctant to talk about their competition. And I think competition is something that anybody looking at an idea will say what's already out there. In the book, I talk about Thomas Edison because we think of him as a brilliant inventor -- the "aha" moment is called the lightbulb moment. But he said he was good at being a sponge -- "going to school on" everything that had happened before he started working on his patent and paying attention to what was going on around him while he worked on it. I think any entrepreneur studies those things -- What's been tried in this idea? Who could emerge as a competitor? -- will have much more credibility with a potential investor than one who says, "I haven't really thought about that," or is reluctant to talk about it.

There are a lot of entrepreneurs who, along life's path, tried some things and didn't find success. For many investors like me, that's not a showstopper at all. If you've had a few hiccups along the way, you can make failure matter. Pick up, learn from it and go forward. Sometimes, I'm more inclined to get behind an entrepreneur who's had one or two startups that didn't make it, on the belief that they're carrying those important lessons forward and will be more effective in their future company.

In all the work you've done with the Foundation, I'm sure you've seen a lot of business ideas, both big and small. What's the single best question that those listening can ask themselves to determine whether their idea has legs and can truly make a change in the world?

Every entrepreneur should say, "Is this bet big enough? Am I dreaming big enough? Is the idea big enough?" And the second thing is, "Am I being bold enough? Have I tapped the people who can help me get there?" One of the principles in my book is "reach beyond your bubble." That's about being aware of what you bring to the party in terms of experience, background and talent. But more importantly, it's about what you don't have at the table or on your team and making sure that you've reached as far as you can through partnerships and people you've tapped. You want to really find people who are not only different than you but who can play an active role in taking your idea even further.

It was something we did with the Case Foundation -- the team around me is world-class -- but it's something we did at AOL as well. We would hire folks who had built their own companies. The guy that really helped bring the internet revolution forward by creating the network that supported, was a guy who had years and years of experience from IBM. We used to refer to him as "the dad" because we were all in our twenties, and he was around 50. We really needed that at the table -- somebody who was tried and true and had seen it all. He ended up playing a transformative role in the company.

Hayden Field

Entrepreneur Staff

Associate Editor

Hayden Field is an associate editor at Entrepreneur. She covers technology, business and science. Her work has also appeared in Fortune Magazine, Mashable, Refinery29 and others. 

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