Anthony Doctolero, founder of GroupGreeting, spreads appreciation (and trees) around the world

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Anthony and Stephanie Doctolero had just $2,500 left in the bank when the world began to fall apart in early 2020.

Two years before, Anthony had left his job in tech sales and account management to dedicate himself full time to GroupGreeting, the digital greeting card company he launched in 2009. It was not his first rodeo.


Anthony Doctolero was a born entrepreneur and website design was his game. There was the dating site First Wink and Ploomy, a sort of poor man's GQ or Men's Health. Some of his sites actually got a little traction, but it just wasn't enough to make ends meet without continuing to work full time. "I tried like 10 other websites that all failed," he laughs.

But by 2018, after nine years of work on GroupGreeting, things were finally looking up. Anthony was ready to take the plunge from his "comfy tech job" to the hard-scrabble life of a small business owner but he needed Stephanie's help.

It wasn't her first rodeo either. Shortly after the couple got married in 2007 (they met in high school at Family Billiards on Geary Street when she was a student at St. Ignatius College Prep and he a student at Lincoln High in the Sunset), Stephanie supported them as Anthony developed, then reluctantly abandoned, his early websites. With GroupGreeting, Anthony wanted her to take a more integral role.

"I said why don't we do this together? What I'm not good at, she's good at," he recalls. "We're pretty amazing as a team."

Over the next two years, GroupGreeting stutter-stepped forward. They knew the idea, which repositioned the office greeting card—the kind that gets shared around for everyone to sign—to a digital platform, was solid but as the company slowly grew, the couple's savings slowly shrank. They kept expenses low, working out of public libraries and coffee shops but it wasn't enough. By 2020, things had gotten dismal enough that Anthony had to borrow money from his son's piggy bank more than once.

Then Covid hit. San Francisco's shelter-in-place order went into effect, and the Doctoleros pulled their kids out of school and stocked up on toilet paper as millions of people around the world left their offices to work from home. Almost everything came to a halt. Everything, that is, except the milestones—birthdays, births, deaths, anniversaries—that shared office greeting cards were made for. And since passing around a card to be signed at the office was no longer an option, corporations, nonprofits and government agencies all turned to the internet to fill the void. GroupGreeting was ready and waiting.

Artist Paula Kuka's GroupGreeting Gives card, the proceeds from which were donated to Healing Foundation.(Courtesy of GroupGreeting)

"Our highs were getting higher every single day. By the end of March, we already did everything that we did revenue-wise in all of 2019. The next month after that, we quadrupled again," says Anthony.

Over the following months, 80 percent of the country's Fortune 500 companies signed up for GroupGreeting, as well as organizations including NASA and the Australian parliament. As of August, GroupGreeting had become the highest traffic greeting card site on the internet, even surpassing industry leaders Hallmark and American Greetings.

All this growth doesn't just impact the Doctoleros, or the signers and recipients of GroupGreeting cards; the environment is prospering too. Since 2019, the company has donated a portion of its revenue to the reforestation organization One Tree Planted. They now have a formal partnership and a goal to plant a million trees in the coming years. As of this month, they've already got the first 10,000 down.

"We made a conscious choice to do this because we wanted to give back and to contribute to something positive. I'm very into what's going on with climate change and for me it was a no brainer. Whether we succeed or fail, let's do something for the environment," he explained.

Working with artists including Benny Gold, Sharee Miller and Paula Kuka, another program, GroupGreeting Gives, has donated funds to 12 additional local, national, and international nonprofit organizations including the California Wildfire Fund, the Lebanese Red Cross, and 826 Valencia.

"The idea was to partner with these artists who are known and have their own following, get them to design a card, and then we'll donate 100 percent of the proceeds to a nonprofit of their choice. It was a huge endeavor, but we raised over $30,000 in three weeks."

Despite GroupGreeting's rapid rise to the big time, the San Francisco son of a single immigrant mom from the Philippines remains humble, hardworking, and homebound in the Sunset, where he's spent most of his life. With their twin goals of sending appreciation and planting a million trees, says Doctolero, "we're just trying to do as much good as we can."

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