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Ever try to teach an older or luddite relative how to use some form of technology for the first time? Of course, we’ve all been there. It can be frustrating, painfully unfruitful, and a precarious balancing act, bridging the communication gap between parties and their connections to cultural references in order for any meaningful connection to occur — a bridge that widens with each year of age difference.

But while experts, academics, media, and business leaders continue to research millennials as a demographic “in the wild” and compare them to baby boomers, generally dismissive of these two generations ever finding any real common ground, the elderly and the young are busy doing something surprising: They’re connecting. To each other. Over tech. And not only loving it, but realizing they’re more alike than they think.

On June 1, in celebration of Intergenerational Day, a heartwarming video suddenly went viral illustrating a new movement that’s currently having a radical and growing impact on society: Millennials mentoring baby boomers, and in some cases, even starting businesses together. On social and business levels, this is very good partnership news, not only because millennials will become the majority of the workforce by 2025 and 8,000 boomers reach retirement age every day (AARP), but because a new report from the Kaufmann Foundation shows that millennials are retreating from entrepreneurship while boomers are now twice as likely to start a company, the latter supported by new networking groups like Startup50Plus.

In the trailer for the award-winning 2014 documentary Cyber Seniors, recently released on Netflix and the subject of this week’s viral video, director Saffron Cassaday follows a group of elderly retirees in their 80s and 90s. The video documents how teenage millennial volunteers connect with seniors in order to mentor them on using technology to improve their daily lives. The surprising result is that seniors are not slow to learn simple technological tasks and, to the contrary, go full speed ahead, wholly embracing every aspect of digital life — even as the millennials become addicted to those actual human interactions with their elders.

One of the high school volunteers says, “They learn a lot from me and I learn a lot from them, and I think I’m actually learning from this that I like older people more than I like younger people.” Another points out, “This is the biggest generational gap ever, and I don’t think there will be one like it ever again. In one way we’ve lost personal connections, but we’ve made up for it with technology.”

The biggest divide between these two gargantuan cohorts, aside from simply age difference, always comes down to their relationship with technology, but a slew of new millennial-led businesses and community programs have popped up to leverage millennials’ native know-how as mentors for aging boomers, bridging the so-called digital divide and responding to the fact that there are fewer and fewer opportunities for senior citizens and millennials to encounter one another in daily life.

A slew of new businesses have popped up to leverage millennials' native know-how for aging boomers.


One such millennial-founded business created to improve the lives of boomers is Denver-based Capable Living, a 5-year-old concierge service that matches millennials with seniors who are aging in place, much like peer-to-peer services such as Instacart or TaskRabbit. CEO Amanda Cavaleri recently told PBS News Hour that she now actively encourages her millennial peers to start businesses to help boomers.

Much like Coursera or Skillshare but for seniors, Techboomers is another startup created by millennials for seniors — an education and discovery website providing free tutorials of popular Internet-based tools and services in a way that’s more accessible to older adults. Founded by Canadian serial entrepreneur and millennial Steve Black, Techboomers’ team offers lessons on social networks such as Facebook and Twitter, online shopping marketplaces such as Amazon, travel booking sites, general tools for living like how to use Google Search, and additional online tutorials that answer questions anyone new to the Internet might have.

The real-world impact online is already apparent, like Twitter sensation and 80-year-old grandma J. Dimps” — short for dimples — who’s on a quest to gain 80,000 followers. She originally joined Twitter with the help of 24-year-old millennial grandson Donny Brandefine.

“Well, it was getting a little boring, so he came over and we tried to figure out something to keep me busy,” she says. “We came up with this idea, and it’s been good.” Brandefine — who Dimps calls “my right arm” — says his grandmother has always had a rambunctious personality and that she’s taken her online celebrity acquaintances in stride. A list called MyAdoptedGrandchildren contains more than 300 celebrities she’s interacted with on Twitter.

April Lane is a freelance writer.