After running Tripadvisor for 22 years, I was searching for my next passion project when I learned that Amazon was pulling the plug on AmazonSmile, its popular charitable program that donated a percentage of eligible purchases to nonprofits.
Astonishingly, the press release blamed a lack of impact, as the average charity only got a few hundred dollars. Despite raising nearly half a billion dollars for charities between 2013 and 2023, Amazon publicly stated it wasn’t having a big enough impact. The company instead pledged to donate billions to fund housing equity, computer science scholarships for underserved communities, disaster relief, and other areas where it felt it could have a bigger impact.
I was intrigued—so I asked around. And sure enough, the big charities loved their six-figure annual unrestricted checks, and the small animal shelter, for instance, appreciated their smaller $200 check. So while $100 million a year might be pocket change to a company like Amazon, it was meaningful and appreciated support to these charities.
I know firsthand what it looks like when a business “fails to make an impact.” When I co-founded Tripadvisor in 2000, our initial business model didn’t work, and the company almost became another casualty of the dot-com bust. But instead of folding, we pivoted to user-generated travel reviews and found a business model that fulfilled a basic human need—an unexpected breakthrough that turned our fortunes around.
Tripadvisor’s success is a testament to human generosity and the power of collective impact. Travelers took the time to share their stories, not because they were paid or incentivized, but because they genuinely wanted to help others. Our breakthrough insight was realizing that Tripadvisor enabled people to share their knowledge and experiences, creating a community built on generosity. By not having to pay for the content, we had a very profitable business model, with travelers being the biggest winners as they got free access to amazing travel insights.
Like Tripadvisor, AmazonSmile tapped into this fundamental human truth: People have an inherent desire to help others–and that impact can have a ripple effect. Research shows that giving-by-proxy programs like AmazonSmile can inspire further charitable actions. In one study, 39.5% of AmazonSmile users chose to donate additional funds, compared to 29.2% of regular Amazon users, suggesting such programs have a larger indirect impact than Amazon may have realized. Similarly, Tripadvisor’s pivot to user-generated content transformed it into the world’s largest travel site, with millions of travelers sharing honest reviews that helped billions more enjoy better trips. In both cases, growth and success were fueled by the generosity of people wanting to make a difference, whether through charitable donations or sharing valuable travel insights.
But it seems Amazon had other priorities, and perhaps AmazonSmile’s real value—fostering generosity—was lost on them. This shift is particularly concerning in light of a broader trend some are calling a “generosity crisis.”
Fewer than half of U.S. households now give cash to charity, according to the philanthropy research foundation Giving USA. Between 2000 and 2016 alone, 20 million fewer households made donations—and the money being donated is increasingly concentrated among a smaller number of wealthy individuals.
That got me thinking: Why not take that model and expand it beyond a single store to tens of thousands of stores? Keeping the notion of letting users select any charity they want, and then building a community of users who care about improving our world. That’s exactly what we’re doing with my new venture, Give Freely. Our platform allows consumers to effortlessly donate to their favorite cause with every purchase, at no extra cost. Partnering with over 10,000 stores, our browser extension and app automatically direct a portion of each purchase to a charity chosen by the shopper. The stores fund the donations rather than paying us affiliate fees. I am personally funding this venture—and won’t take on any investors as we have no intention of ever making a profit.
Many retail outlets and third-party platforms have integrated charitable giving into their business models, making it easy for consumers to support causes while shopping. Major retailers like Target and Walmart offer donation programs where customers can round up their purchases, with the difference going to charity. Brands like TOMS and Warby Parker have embedded philanthropy directly into their operations, and grocery chains like Whole Foods have launched initiatives such as the “Sourced for Good” program, which funds community projects in agricultural regions. These efforts encourage customers to engage in charitable giving as part of their everyday retail experience, fostering a sense of purpose alongside consumerism. In addition to retail-driven programs, search engines like Ecosia plant trees every time you search using them, and browser plug-in Shop for a Cause, like Give Freely, offer online shoppers easy ways to contribute to charity.
Our goal is to have as big an impact as possible. My experience at Tripadvisor taught me that small contributions, when aggregated, can have a tremendous impact. Now my goal is to make generosity a seamless part of everyday life, fostering a culture of giving that goes beyond just fundraising. As more people use this form of giving, we hope they will build deeper connections with the causes they support, leading to more engagement, volunteerism, and larger personal donations.
Reflecting on my four decades in business, I am more convinced than ever that people want to make a difference. They just need the right opportunities to do so.
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