Editor's note: "Shirtsleeves to shirtsleeves in three generations" is the classic curse of an entrepreneurial family, meaning that wealth rarely survives much past the founding generation. These families plan on defying the odds.

Elizabeth Rees was 26 years old when he finally popped the question. She had studied journalism in college and was getting her degree in global communications from the American University of Paris when her parents flew to Europe from Milwaukee and took their middle child out for lunch. "Have you ever thought about joining the family business?" asked her dad, Mike Rees, who runs a 91-year-old Midwestern printing company. "No," said Elizabeth. "I never have."

As a child, Elizabeth had only the dimmest notion of what went on at Kubin-Nicholson, the grand-format printing plant her dad and uncle inherited from their father, who died unexpectedly from cancer. They were 29 and 31, respectively. Growing up, she made occasional visits--her dad instructed her on the evils of booze and cigarettes, using the billboards he was printing as teaching aids--but never imagined herself working there.

Make the second generation financially accountable
When Elizabeth Rees asked her dad to invest in Chasing Paper, he made it clear this couldn't be some vanity project of the owner's daughter. He told her he would back the new division under the condition that Elizabeth would operate her own P&L, while continuing her sales duties.

Mike saw in his daughter, the storyteller of the family, a reflection of his father, who rose patiently through the ranks at Kubin-Nicholson and eventually bought out the previous owners. At lunch that day in 2010, he offered Elizabeth a job in the plant's New York City sales office, selling billboards and bus wraps and point-of-sale displays. It took a while for Elizabeth to agree to do it; the option to move to New York tipped the scales.

But the industry jargon and the boys'-club sales culture made for a rough start. Then in 2013--two years into her new role--Elizabeth decided to experiment. Looking for other ways to use Kubin-Nicholson's advanced digital printer, she did a run of modular wallpaper for the Manhattan office of a friend's startup. Then, suddenly, she was getting emails from her friend's friends, asking, "Where can I buy that?"

The result was Chasing Paper, an e-commerce company that makes 2'x4' Instagram-worthy removable wall­paper, and is Kubin-Nicholson's first startup. After the deluge of requests, Elizabeth pitched her father the concept: Stylish removable wall­paper, she explained, was already a thing, but there was a hole in the market. Kubin-Nicholson's digital printer sometimes sat idle, she argued, and adding a few runs of new product would require no retraining, no new investment in payroll or machinery, and no additional sales staff. She could license designs from hip artists and designers, and sell the decorating accessory, which is made of a poly-fiber fabric, directly to consumers online for $40 apiece.

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Back in Milwaukee, Mike's managers were skeptical anyone would pay that much for eight square feet of printed fabric--a massive margin compared with the usual 20 percent they got selling larger swaths of printed vinyl. But Mike was intrigued by his daughter's propo­sition. He'd been wanting to break into online retail, and had yet to find a way. Kubin-Nicholson had an existing deal with Fathead, a sports decal company, which meant he could handle the back end--production, packaging, and shipment. It was the front end that baffled him--artist relations, social media, all that New York stuff. But that's where he knew Elizabeth would flourish. He gave her the verdict: Kubin-Nicholson would invest in the startup as a new division of the company, but this could not be a vanity project for the owner's daughter. He told Elizabeth she'd have to divide her time between the sales office and Chasing Paper, which would have its own P&L. "He made it clear it would stand or fall on its own," she says.

Four years later, Chasing Paper is on track to hit $1 million in sales. Elizabeth, still its only full-time employee (even as she spends 10 percent of her time servicing accounts for Kubin-Nicholson and serving on its board), runs the startup from a sublet desk at an architecture firm in SoHo. She straddles two worlds--directing photo shoots for the brand's website and its wildly popular Instagram account and meeting with designers and illustrators; and overseeing her division's production back at the Milwaukee plant. She recently persuaded her dad to purchase two more high-end printers to meet demand from customers who want their wall­paper within 36 hours, which brings Kubin-Nicholson's total investment in Chasing Paper to about $75,000.

But Elizabeth is also finding herself in a newly crowded field of direct competitors, and is antsy to accelerate the growth of her already profitable startup. She's trying to convince Mike that next year Kubin-Nicholson should invest more in this division that still accounts for only a small part of the company's $15 million revenue. She tells him she needs to hire designers, license artwork, amp up online marketing, and develop new products. Mike is starting to come around. At 65, he knows his industry is fading, and the only area of his company with optimism and steady cash flow is the part his daughter's in charge of. Who knows, he wonders--perhaps she'll even take over the entire company one day. "Specialty decor," says Mike. "That's where we feel the growth will be. Where Elizabeth and Chasing Paper are."