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Running a Second-Act Business With Your Kid

Combining complementary skills of two generations can be a recipe for success

By Chris Farrell and Richard M. Schulze Family Foundation and EIX

“It’s awesome working with my dad,” says Case Bloom, 30. The feeling is mutual, says his father, David, 58: “We are good complements to one another.”

Among the more striking developments I learned researching my book, Unretirement, is the rise in boomer parents going into business with their adult children, like the Blooms — co-owners of Tucker & Bloom, a Nashville, Tenn. luggage business.

In the past few years, setting up a multigenerational enterprise has been a mutually savvy way for boomers and their kids to deal with tough economic times. The parents typically have capital and plenty of experience, while their adult children burst with energy and tech skills.

From 'You' to 'We'

The Blooms, and their business manufacturing highly-crafted messenger bags targeted at the DJ market, are a prime example. Before opening shop, David had spent his career in bag design and was director of travel products for Coach in New York City before he lost that job. When Case was in college in Nashville, studying business, he’d offer pointers to help his dad’s venture. “His logo was so bad. Horrible,” laughs Case. “I’d tell him, ‘You’re doing it wrong. Do it like this.’”

Eventually, Case says, it became “We should do it this way. The business happened organically.” Today, father and son each own half of the company, which has seven employees. David handles design and product development; Case is in charge of anything to do with the brand image and online sales. He’s also the one making frequent runs to Home Depot for the business’s factory and to the Post Office for shipments. “I have a different set of skills than my father,” says Case, who is also a part-time DJ.

When Kinship Is Friendship

One reason for the growing second-act-plus-child trend: surveys repeatedly show that today’s young adults generally get along well with their parents — and vice versa. “The key is an attitudinal shift in the relations between generations,” says Steve King, founder of Emergent Research, a consulting firm focused on the small business economy. “Boomers are close to their kids and the kids are close to their parents.”

Take Amanda Bates, a Gen X’er, and her mother Kit Seay, co-owners of Tiny Pies in Austin, Texas. “We’ve always had a close relationship, feeding off one another, finishing each other’s sentences,” says Kit, 73. They’d long wanted to do something together.

Several years ago, Amanda got the idea for making handheld pies from her son’s desire to take pie to school. So she and her mother began selling small pies, based on family recipes, in local farmers markets. They now sell them throughout the state, mostly through specialty stores, and opened a retail storefront at their wholesale facility in March 2014. Kit focuses on the creative and catering side of the business; Amanda’s in charge of the basics of running an enterprise. “The trust is there,” says Kit. Amanda agrees. “Yes, the trust is there. If she says something will get done, it will.”

Teaching Your Child Trust

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Trust and complementary skills are also themes for Lee Lipton, 59, and his son Max, 25, and their Benny’s On the Beach restaurant in Lake Worth, Fla.

Lee, the restaurant's principal owner, came out of the clothing manufacturing business, moving to Florida after the Calvin Klein outerwear line he ran with a few partners was sold. He bought Benny’s a few years ago. Max, who’d wanted to get into the food business, is one partner; the other is chef Jeremy Hanlon. Lee’s the deal maker, Max manages the restaurant and executive chef Hanlon handles the kitchen. “The three of us trust each other incredibly and when one person feels strongly about something we tend to do it that way,” Lee says. “Very rarely after talking do we disagree, and that format was identical to my past partners. I want to teach Max and Jeremy that closeness.”

For second-act family businesses, creating boundaries between work and home is advisable, but easier to say than do. Speaking about her current relationship with her mom, Amanda Bates says: “We used to go out together and have fun, go to garage sales, that kind of thing. Now, when we get together, the business always come up. Even at family dinners, we end up talking business.”

The Win-Win of Multigenerational Businesses

But in the end, it’s family that makes these businesses succeed.

Bianca Alicea, 26, and her mom Alana, 46, started tchotchke-maker Chubby Chico Charms. in North Providence, R.I. with $500 and less than 100 charm designs at their dining room table in 2005. They now have roughly 25 full-time employees and sell several thousand handmade charms. Alana is the designer; Bianca deals more with payroll and other aspects of the business. “It’s important to remember you are family,” says Bianca. “Things don’t always go according to plan, but at the end of the day you have to see one another as family.”

Intergenerational entrepreneurship, it turns out, can be a win-win for boomers and their kids. For the parents, it’s the answer to the question: What will I do in my Unretirement? For their adult children, working with mom and dad provides them with greater meaning than just picking up a paycheck.

Photograph of Chris Farrell
Chris Farrell is senior economics contributor for American Public Media's Marketplace. An award-winning journalist, he is author of the books "Purpose and a Paycheck:  Finding Meaning, Money and Happiness in the Second Half of Life" and "Unretirement: How Baby Boomers Are Changing the Way We Think About Work, Community and the Good Life." Read More
Richard M. Schulze Family Foundation and EIX
By Richard M. Schulze Family Foundation and EIX

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