Entrepreneurial Cliff Diving: Interview with Whole Whale’s George Weiner

by / ⠀Entrepreneur Interviews Entrepreneurship / January 19, 2015

Hiscox Courageous Entrepreneur Interview Series

Hiscox-Small-Business-Insurance-Logo-6001This is part four of the ten part series. Follow the Hiscox Courageous Entrepreneur interview series on Under30CEO.com.

Interview Series Sponsored by Hiscox Small Business Insurance.  Hiscox specializes in protecting IT/technology, marketing, consulting, health and beauty, photography and many other professional services businesses, tailoring coverage to the specific risks in your industry.

George Weiner

Whole Whale Founder George Weiner

“When you start a business, there are two versions of driving a car off of a cliff. You’ve got the Dukes of Hazard style where there is a bridge on the other side; their at least aimed at something. The other is the Thelma and Louise (style), where there are no sort of goals other than the bottom of the canyon. When I drove my car off of the cliff, I was aimed very carefully.”

Whole Whale founder George Weiner had spent seven years working from the bottom to the top of DoSomething.org, the largest organization for teens and social cause in the US, to become the organization’s CTO. He loved the organization and his position. So why did he drive his car off of the entrepreneurial cliff?

His goal was to start an impactful digital agency that would increase the impact nonprofits have on the world. Having gotten his feet wet in the non-profit world, George was inspired with their mission and vision of changing the world, despite the difficult nature of working with nonprofits instead of traditional businesses. “The actual behavioral change is often what a not-for-profit is trying to do with their online platform. Amazon’s trying to get me to buy a stupid blow-up doll… Not-for-profits are trying to get you to make social change. That is as challenging as it comes.”

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Whole Whale focuses specifically on increasing the impact of non-profits by leveraging data and technology. The name comes from the way the Inuits used every part of the whale, not just one or two parts. Instead of just a donate button and simple landing page for a not-for-profit, Whole Whale helps them utilize everything that’s available to expand their brand and increase the chances of making a significant impact. Organizations they have worked with include The Grassroot Project, Volunteer Match, Power Poetry, MenEngage, National Aphasia Association, and Planned Parenthood.

Whole Whale Team

No profit, but plenty of opportunities

George found an interest in helping others at an early age. In high school, he was the President of the community service club in high school. “We don’t have a ton of time, so I might as well spend it working on great causes.” It wasn’t until after high school that he realized people worked and made a living working for non-profits.

George encourages others to get involved in the nonprofit world. “The opportunity you get, working with a non-for-profit of a mid to small size – is that when you walk in the door, you’re handed as much as you can conceivably do, and then they top it off. Suddenly you’re in marketing, suddenly you’re in tech, and suddenly you’re in fundraising. It’s an opportunity to really explore everything that interests you.”

Best piece of advice for young entrepreneurs

Waiting for the ‘perfect’ time to launch a business will keep many potential entrepreneurs from ever starting to pursue their dreams. George urges young entrepreneurs; “Whatever you’re working on – launch it right now! Put it out there in the world and see what comes back. Waiting for perfect is a certain route to failure.”

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If George would have remained in his job at DoSomething.org, which he cared for deeply, hundreds of nonprofits would not have received the help and assistance that Whole Whale provides its clients and he would not be living out his dream. Staying comfortable and not taking the drive toward that bridge on the other side will ensure safety, but it will also ensure you’ll never see what’s on the other side. When getting ready to jump off the entrepreneurial cliff, make sure you’re aiming for a bridge on the other side, but you have to take the jump to have a shot at getting there.

Additional Interview Highlights

– Difference between entrepreneurs and freelancers – trusting other people.

– Why “Acting from a place of scarcity instead of abundance” was an early mistake.

– Q: How important is insurance to your business in terms of risk, and do you have it?

A: Absolutely. I’m risk averse. I think of all of the ways that things will fail while being blindly optimistic that things are going to work out…As soon as you create products out there in the world, you open yourself up for lawsuits. Am I willing to risk the entire company on one product if something should go wrong? Absolutely not.”

Listen to the full interview:


Connect with Whole Whale on Twitter, and check out the Whole Whale Podcast here.

About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on Under30CEO.com, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.


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