Multigenerational, family-owned businesses are the stuff of American legend. Grandfather starts a small business that eventually thrives. His son or daughter steps up to work alongside the founder. Eventually the third generation – the grandkids – become involved. The American business landscape is filled with examples. 

But let’s face it – it doesn’t always work. There are plenty of families in which the second generation shows little or no aptitude or desire to join “the family firm.” Either the business gradually dies as the founder ages, or else the sons and daughters sell it off as quickly as they can, and the family connection is forever severed. 

But this week we came across this article from NextAvenue (first published last June) in which freelance business writer Lin Grensing-Pophal shows us a slightly different model: “skip-generation entrepreneurship.” It’s a type of family business that combines the wisdom of an older generation of business founders with the energy and tech savviness of their grandchildren. In today’s digital economy, skip-generation entrepreneurship seems to be finding new adherents as the “first and third generations” create a new family dynamic. 

Our take-away: for aging adults who still have an entrepreneurial spark, but might not possess the tech-savviness that today’s businesses demand, maybe starting a business with your grandson or granddaughter is the ticket to a successful venture! 

Baby Boomers Stay Engaged Alongside Entrepreneurial Grandkids 

“Partnerships between ‘skipped’ generations have not been common,” Grensing-Pophal writes, “but they are becoming more so as baby boomer retirees seek to stay engaged and productive, and younger generations with an entrepreneurial spirit are eager to join them.” 

In her NextAvenue article, Grensing-Pophal explains that this pairing of boomers and their tech-savvy grandchildren makes perfect sense.  

“It’s perhaps not surprising that a special bond can exist between grandparents and their grandchildren,” she says. “No longer saddled with the stress of working and, in many cases, freed from the obligation of caring for underaged grandchildren, boomers can relax and enjoy an adult relationship with their children’s kids.”   

The Benefits of Skip Generation Partnerships 

As the NextAvenue article states, for many families the grandchild/grandparent relationship is not just personal, it’s professional.  

“Skip-generation entrepreneurship is a business partnership in which older adults partner directly with their grandchildren in a business, bypassing the middle generation,” Grensing-Pophal writes. She spoke with Jeff Mains, founder of executive training firm Champion Leadership Group in Plano, Texas, who said this arrangement is growing in popularity. 

“I’ve worked with family businesses at all levels of scale,” says Mains, “and skip-generation entrepreneurship is something I’ve seen more often than people might expect – especially when grandparents are founders or legacy holders and grandkids are just beginning to find their lane.” 

Grandparents, says Mains, “bring wisdom, stability and a long view. Grandkids bring tech fluency, modern market instincts and new ways of thinking.” 

Grandfather Becomes “Unexpected Co-pilot” of Online Venture 

Grensing-Pophal introduces us to Garrett and Hiroshi Yamasaki as an example of a successful skip-generation partnership. After years with Google and Texas Instruments, tech entrepreneur Garrett launched WeLoveDoodles, a website for poodle-mix fanciers. When he decided to turn the site from a side project into a full-time venture, his grandfather became his unexpected co-pilot.  

NextAvenue calls it a marriage of enthusiasm and experience. 

“At 78, he’d spent decades running a small import-export business in Osaka,” Yamasaki told Grensing-Pophal, “and while he’d never sent a tweet or optimized a landing page, he understood something I didn’t yet: how to build trust that outlasts trends.” 

Older Generation Instills the Business with Loyalty, Perspective 

As Grensing-Pophal explains, the grandson has the technical ability while the grandfather brings loyalty and perspective. “When I pushed to scale too fast post-pandemic,” Garrett Yamasaki recalls, “he shared stories of his 90s recession survival, urging me to prioritize profit over vanity metrics. We compromised, launching a slow-growth subscription model that’s now 35 percent of revenue.” 

Most skip-generation partnerships benefit from the blending of old and new perspectives and skills. Each generation brings its own “best practices” to the mix. Customer communication is a perfect example. “While I obsess over A/B testing TikTok ads,” the younger Yamasaki admits, “he reminds me that handwritten thank-you notes to loyal customers — yes, snail mail! — create bonds algorithms can’t replicate.” 

Hiroshi Yamasaki has also saved the company with his hard-earned financial caution, Garrett told NextAvenue. “His lessons on inventory frugality — ‘Never let your warehouse get fatter than your heart’ — saved us during supply chain chaos, proving that decades-old wisdom can be startup gold,” the grandson proudly states. 

Skip-Generation Entrepreneurship Can Be Challenging 

Despite the many benefits of these partnerships, the NextAvenue article emphasizes, they are not without their challenges. One example, says Grensing-Pophal, lies in the technology gap that can create tension.   

The Yamasaki partnership illustrates this potential for friction. “Early on,” says grandson Garrett, “[grandfather would] print out Shopify reports to review with a red pen, while I live in Slack. We met halfway: I built him a custom dashboard with larger fonts and fewer clicks.”  At the same time, grandfather Hiroshi used his experience to teach Garrett how to be better at reading body language during vendor negotiations. 

Family Dynamics Can Leave Middle Generation Feeling Bypassed 

Another risk, executive trainer Mains told NextAvenue, is that a partnership between grandparent and grandchild can leave the in-between generation feeling left out, triggering the potential for family friction. 

In addition, Mains adds, “the power dynamic can get messy if expectations aren’t aligned. A grandparent may want to maintain control longer than the grandchild expects, or the grandchild may not be fully ready for leadership but is treated like a successor anyway.” 

In any case, experts agree, any family drama has to be kept outside the office. “When tensions flare — like his resistance to AI chatbots — we table debates until after karaoke nights,” Garrett Yamasaki told NextAvenue’s Grensing-Pophal. 

Advice for Both Generations on Making Partnerships Work 

In preparing her article for NextAvenue, Grensing-Pophal sought out an expert in family entrepreneurship to see how both generations can act together to improve the odds of successful intergenerational partnerships. 

“Lauri Union is founding executive director of the Bertarelli Institute for Family Entrepreneurship at Babson College in Wellesley, Massachusetts,” Grensing-Pophal writes. “Union grew up in a family business that made her a leader in the metal roofing and siding industry and a mentor to future and current family business owners about how to succeed in skip-generation enterprises.”  Here’s her advice for both grandparents and grandkids, presented verbatim from the article. 

Advice for Grandparents: 

Be curious. “Explore your grandchild’s ideas, even if they don’t seem like they will work,” Union advises. “Ask questions to understand why your grandchild has this idea. You might be surprised by the ideas you come up with together.” 

Focus on sharing versus directing. Union recommends sharing your life experiences with grandchildren rather than telling them what to do. Then come to a decision together. “You have a lifetime of wisdom; the greatest gift you can give your grandchild is access to that,” she says. “But your grandchild needs to be able to apply that wisdom in their own way.” 

Delight in learning. “Treat this as a wonderful opportunity to learn from a young person, rather than as a threat,” Union says. 

Advice for Grandchildren: 

Take in the knowledge. Your grandparent has a wealth of experience, Union says, and can help grandchildren learn how to do things. “It’s what we learn through a lifetime of experience rather than in school, and it’s invaluable,” she says. “Use this opportunity to ask lots of questions and explore your grandparent’s life experiences.” 

Bring your future vision. Grandchildren have much to offer as well. “The superpower of generations working together is blending the knowledge of the older gen with the vision of the future of the younger gen,” Union says. “Share your ideas, the tech tools you use, and what your friends are thinking openly.” 

Don’t be afraid to share your own view. “Ask questions when you’re not sure about a decision,” Union advises. Respect for the older generation doesn’t mean automatically agreeing. It means engaging and learning together. 

Advice for Both: 

*Treat this as an opportunity to learn about each other and deepen your relationship. 

*Talk about yourself, including your feelings. 

*Be patient with each other. 

*Never let disagreements about a business idea become personal. 

*Celebrate your successes, even the small ones. 

Skip-Generation Partnerships are Focused on Shared Vision  

The NextAvenue article concludes on an encouraging note. 

“If both sides come in open, clear-eyed, and committed to the same vision, skip-gen entrepreneurship can be powerful,” says Mains. “But if it’s driven by nostalgia or forced involvement, it can stall momentum before it starts.” 

Grensing-Pophal offers a special note to aging adults who still want to use their skills and experience. “For retirees still hoping to make a meaningful contribution while mentoring their grandchildren and sharing their experiences, insights and values, skip-generation entrepreneurship offers a unique opportunity to leave a legacy while keeping it all in the family,” she writes. 

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(originally reported at www.nextavenue.org)