3 Success Strategies From Oprah, Richard Branson and Jeff Skoll


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I’ve always been drawn to entrepreneurs by their relentless determination to be successful and positively impact the world. They share a common spirit, a willingness to risk everything and work tirelessly to make their vision a reality.

But I’ve also found that entrepreneurs are among the most accessible and open when sharing their experience by serving as mentors to those looking to start their own enterprises.

Over the last three decades, I’ve had the privilege of working with some remarkable entrepreneurs, starting with my parents.

As schoolteachers with modest salaries, my parents faced the challenge of raising a family and paying college tuition for their sons. So, my parents created a side hustle during their summers off. Every year, they would buy a house that needed significant renovation, and the whole family would move in and get to work. Updating and re-selling our houses allowed us to have a comfortable upbringing, afford college and support my passion for social justice.

Other mentors followed, each teaching me critical lessons I could apply to the impact I wanted to create.

Related: 7 Ways to Maximize Mentor Relationships in Business

Oprah Winfrey: The art of attention to detail

I first appeared on the Oprah show in 1999 at age 16, after the charity I started with a group of other teens received extraordinary media attention. During the broadcast, which showcased our work at Free the Children, Oprah spontaneously announced that she wanted to partner with us. Her goal was to create a living legacy by working with us to build schools in the developing world and provide access to education for thousands of children.

But Oprah’s commitment wasn’t a blank check, and she wouldn’t cut us any slack just because we were kids. The details mattered. We had monthly meetings with her Chief Operating Officer to report on progress, show our financials, and demonstrate we met our targets.

Putting controls in place – even when dealing with a charity run by teens – showed me that no shortcuts were allowed in her operations.

When I would spend time with her in Chicago, I watched her review every line of copy for her magazine. She would script her TV show with her team, minute by minute, before going on air. While her shows appeared casual, each second was planned with military precision.

Oprah’s commitment to quality, from her interviews to her philanthropic initiatives, showed me that excellence comes from sweating the small stuff and that attention to detail can often be key in determining which enterprises succeed and which fail.

According to U.S. Bureau of Labor Statistics data, about 20% of new businesses fail during the first two years, 45% during the first five, and 65% during the first 10. Just 25% of new businesses make it to 15 years or more.

So, whether it’s paying attention to the preferences of your customers (80% of whom want a personalized experience), keeping strong tabs on your financials (38% of start-ups go broke) or ensuring you have quality control under control (poor quality can cost even successful companies up to 15% of revenues), the details matter.

Related: 5 Ways to Make a Mark on the World Like Oprah Winfrey

Richard Branson: Your purpose is your brand

I first met Richard Branson in rural East Africa while hosting him on a tour of our projects in the region. He described his entrepreneurial philosophy against a backdrop of lions and antelope, where he told me that the most important thing for new entrepreneurs to understand is the power of their brand.

Too often, new companies try to develop a clever name or identity that doesn’t relay anything about the product or service they offer.

Known as a guru of branding thanks to the success of the Virgin brand, which is known across the globe to represent fun, adventure and quality, Branson feels a brand should clearly reflect its organization’s identity and purpose.

He argues that successful businesses only exist because they make a difference in someone’s life. Today’s conscientious consumers seem to agree, with 94% saying purpose drives their purchasing choices.

Simply put, if an enterprise fails to deliver on its purpose, consumers won’t support it. So, finding your purpose and integrating it into every aspect of your company – especially your brand – will transform your organization.

Related: What Richard Branson Learned From His 7 Biggest Failures

Jeff Skoll: Creating business solutions to take on grand challenges

Like Branson, eBay’s first president, Jeff Skoll, learned that acquiring wealth and helping solve the grand challenges of our time can go hand in hand. As an entrepreneur, you don’t need to choose between earning revenues and changing the world for the better – you can do both.

Skoll strongly advocates social entrepreneurship – using business principles to address pressing social and environmental challenges.

Many know Jeff as the founder of the Skoll Foundation, which drives large-scale change by investing in social entrepreneurs and innovators. What’s less known is that he launched the Capricorn Investment Group, which funds mission-driven companies that demonstrate the power of using commercial solutions to address the world’s most pressing problems. Along with rock star Bono, Jeff also founded the TPG Rise Fund, the largest impact investing platform in the world.

When I met Skoll, our charity was doing well, but it was at a plateau; we could be doing more, but the traditional fundraising methods constrained us.

Skoll showed me that by creating a social enterprise, we could harness the power of business to develop reliable revenue streams to fund our charity. With his mentorship, we forged partnerships with socially conscious brands like Walgreens, Nordstrom and Pacsun to sell products handmade by 3000 women artisans in developing countries. We later expanded to coffee and chocolate. All of the profits were donated to charity or reinvested to grow the social enterprise.

Skoll’s gift to me was to push me into challenging my assumptions that charities and the non-profit world had to be siloed from business principles when, in fact, it was the opposite.

I encourage new entrepreneurs of all ages to reach out and be proactive. Take the time to network with the successful leaders in your own community. The worst they can do is say “no,” but I’m willing to bet they’ll be eager to help.


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