Cross-Generational Partnerships Can Be Magical for Business

The older partner's wisdom, experience, and connections can complement the younger generation's fresh thinking. 

EDITOR'S NOTE: This article is part of The Great Unretirement, a Next Avenue initiative made possible by the Richard M. Schulze Family Foundation and EIX.

Many retirees opt to start a business in the second act of their working lives, often partnering with members of younger generations when they do so. These intergenerational partnerships are likely to be increasingly commonplace as the workforce includes members of five generations.

That's good news for retirees hoping to get back into the world of work, not as employees, but as business owners. As they consider taking the leap, many recognize the potential value that younger generations offer and they're deciding to join forces to bring the benefits of both generations to bear in driving business success.

Sami Andreani, a finance expert and CFO at Oppizi, a New York startup offering data-driven offline marketing technology, says he's worked with retirees who have teamed up with younger partners to launch a business and that these relationships can work quite well. Usually, he says, retirees bring money and stability to the relationship.

"They've got savings, they know the banking system, they've been through ups and downs in the economy, so financial bumps don't shake them as much." While younger partners don't usually have that kind of financial stability, "they do have energy, tech savvy and a different way of seeing opportunities — especially online."

Andreani shares an example of a retiree who teamed up with someone in their twenties to launch a clothing resale platform. "The retiree had experience in retail and finance, knew suppliers and understood how to negotiate contracts. Meanwhile, the younger partner knew how to build a website, run social media ads and attract an audience online." The relationship worked, he says, because the retiree's funding allowed them to avoid expensive debt, and the younger partner's digital skills brought in customers quickly, helping the business be profitable sooner.

Intergenerational partnerships work, Andreani says, because each person has something the other needs. 

When Jamie Pritscher graduated from college, she took on a job with Tasty Catering. There she met Tom Walter, one of the owners of the company. Since then, Tasty Catering has helped to launch numerous offshoots, including two companies that Pritscher launched with Walter —That's Caring, a socially responsible gift company and Nuphoriq, a marketing company that exclusively serves the catering and event venue industry.

Pritscher says that Walter saw her passion for entrepreneurship and helped make it happen.

"I always equated starting a business with Tom Walter to starting a business with a safety net," Pritscher says. "You get to be the founder yet still have someone invested in your success — watching over you to help guide, give advice, share contacts, and most of all, provide the capital to start."

There's real synergy between generations, Pritscher says, with each bringing unique talent, perspectives and experience to the relationship.

Senior business leaders, like Walter, she says, bring established networks and contacts, access to capital, emotional intelligence and leadership experience, and valued mentorship based on their knowledge and experience. Younger generations have the time and drive to start a new company, understand market needs and emerging trends, and often have advanced technological knowledge, she says.

Eric and Cameron McEntire have also benefited from a cross-generational business relationship when starting a franchise business—Woofie's of Greenville, South Carolina, a pet care services company. Cameron's father invested 24% in the business as a silent partner. She says she relies on her father as their sounding board and credits the business for "adding a loving, new layer to their relationship."

The relationships aren't without challenges, though.

When launching Woofie's, Cameron says, boundaries and roles had to be explicitly created to avoid "stepping on each other's toes." There is a learning curve, she says, when working across generations.

Jon Morgan is CEO and editor-in-chief of Venture Smarter and helps startups navigate business challenges including the challenge of retirees and younger generations working together. "One of the most common issues I see in these partnerships is the difference in decision-making pace," says Morgan. "A retiree may value a more methodical approach based on years of experience, while younger partners tend to be more inclined toward quick decisions and adaptability." This, he says, can cause tension if not addressed early on.

Different generations also often have different leadership styles, says Jeff Kaiden, CEO of Capacity, a logistics company. "More experienced professionals might be risk-averse, while younger entrepreneurs are willing to push boundaries." This can work well, he says, but there needs to be a clear structure in place. It's important to define goals early on, ensure that both partners understand how decisions are made and agree on long-term goals. 

Morgan shares an example, recalling a retiree client who was entering a partnership with a younger co-founder to launch a sustainable fashion brand. Their challenge was in achieving alignment on product development timelines. "The retiree wanted to carefully source materials and follow traditional methods, while the younger partner pushed for rapid prototyping and faster iterations," he says.

They overcame the problem by creating a flexible roadmap —"setting longer timelines for critical steps but allowing faster innovation on others." The result, he says, was a successful launch and strong market presence.

Nirav Chheda is a tech expert, entrepreneur and co-founder/CEO at Bambi NEMT, a business in the non-emergency medical transportation (NEMT) industry. He recalls a situation where the company was pushing to roll out a new dispatch feature in a few weeks but was being urged by "our more seasoned advisor" to slow down and consider the impact on insurance workflows. That difference in opinions and approach, he says, "actually helped us avoid a massive billing error." While at the time, he admits, it felt like a delay, in hindsight, "it saved us from rework and trust issues with our partners."

The younger generation, says Chheda, brings "speed, product intuition and a strong focus on experience — things that can challenge legacy thinking in a good way." But he adds: "We also benefit hugely from older partners who've already lived through cycles of change and know when a flashy feature won't hold up in the real world."

"Building a business from the ground up is a challenge at any age, but when different generations come together, the results can be transformative," says Kaiden. In logistics, he says, experience is everything. "There's no substitute for understanding how supply chains function, how to anticipate disruptions and how to optimize operations."

At the same time, Kaiden says, "Technology is constantly reshaping the industry and younger generations bring fresh ideas, digital fluency and a new way of thinking about efficiency." Combining these strengths, he says, can be powerful. However, one of the greatest challenges can be communication.

"People who have been in the industry for decades tend to trust traditional methods because they've worked," Kaiden says. "Younger professionals want to innovate, sometimes without fully appreciating the risks of disrupting established processes."

Navigating these differences, Kaiden says, can be achieved through regular feedback. Instead of assuming that one approach is better than the other, he says, take the time to evaluate what works best for the business.

The bottom line for anyone considering these kinds of partnerships is simple: Be clear on roles, don't rush the relationship and listen harder than you speak especially when someone's done this longer than you've been in the game.

"It's not about age," Andreani says. "It's about mixing two completely different ways of thinking and doing into something that works financially and practically."