Hand Down the Family Business but Keep a Hand In

The younger Yamasaki says his grandfather brings loyalty and perspective to the relationship. "When I pushed to scale too fast post-pandemic, he shared stories of his 90s recession survival, urging me to prioritize profit over vanity metrics," he says. "We compromised, launching a slow-growth subscription model that's now 35% of revenue."

Skip-generation partnerships also work because of the unique skills and best practice insights each generation brings. "While I obsess over A/B testing TikTok ads, he reminds me that handwritten thank-you notes to loyal customers — yes, snail mail! — create bonds algorithms can't replicate," Yamasaki says.

In addition, he shares: "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."

Despite the many benefits of these partnerships, though, there are some challenges to overcome.

For instance, Yamasaki says, sometimes tech gaps can be uneasy. Given his strong tech background, that may have been more of an issue in his case, but he recalls: "Early on, he'd 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, and he schooled me on reading body language during vendor negotiations."

Another risk, says Mains, the executive trainer, is that the middle generation might feel left out or bypassed. That can create resentment — especially in legacy businesses. In addition, "the power dynamic can get messy if expectations aren't aligned," he says. "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."

Finally, regardless of the dynamics or the generations involved, a big no-no for family enterprises is family drama at the office. "When tensions flare — like his resistance to AI chatbots — we table debates until after karaoke nights," says Yamasaki.

There are a number of things that members of both generations can do to improve the odds of success for their intergenerational endeavors.

Lauri Union (shown above in photo) is founding executive director of the Bertarelli Institute for Family Entrepreneurship at Babson College in Wellesley, Massachusetts. 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.

• 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.

• 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.

Yamasaki says his grandfather's greatest contribution as a business partner has been "teaching me that legacy isn't about exit strategies, it's about building something that outlives you." He says both he and his grandfather now mentor the next generation — "his great-granddaughter, my niece" — on her guinea pig accessory side hustle. And so, he says, "The cycle continues."

"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."

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.