The 21 Hats Morning Report

The 21 Hats Morning Report

Look Who’s Starting Businesses Now

Driven by necessity as well as opportunity, septuagenarian entrepreneurs are suddenly very much a thing.

Loren Feldman's avatar
Loren Feldman
Oct 06, 2025
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Good Morning!

Here are today’s highlights:

  • The last time Kurt Wilkin sold a business, he jumped back into the game too quickly.

  • “If you aren’t using AI and you’re a CEO, what are you doing?” asks the CEO of MasterClass.

  • The SBA is making it easier to borrow money to expand your business.

  • Even for big companies with a head start, re-shoring manufacturing is a challenging process.

ENTREPRENEURSHIP

More people are choosing to start businesses in their seventies: “These emerging septuagenarian entrepreneurs share many motives with younger counterparts. They want to be their own boss, set their own schedules, and pursue meaningful projects. While older entrepreneurs might have lost some stamina, age has benefits. People in their eighth decade can leverage years’ worth of contacts and experience. With their children grown, they may feel free to address what has long bothered them, like clutter and costly in-home care. Or, in the case of the founders of Judson Squared, dull trial lawyers. ‘They’re boring as hell,” says Judson Vaughn, 71, an actor and filmmaker. He partnered with attorney Judson Graves, 77, known for his persuasive court performance, to create online courses to teach lawyers how to be entertaining as well as effective.”

  • “Self-employment rates rise dramatically as people age. Nearly 30 percent of employed people in their 70s work for themselves, almost double the share of self-employed people in their 60s, says Cal Halvorsen, an associate professor of social work at the Brown School at Washington University in St. Louis. That translates into about 1.3 million septuagenarian entrepreneurs, he says.”

  • “Charlotte Bishop never aspired to be an entrepreneur. ‘I didn’t think it would offer a steady income,’ she says. Widowed at a young age, with two children, Bishop pursued her master’s, and taught office administration skills at City University of New York. Once retired, friends and neighbors asked for help organizing files and clearing clutter.”

  • “Seeing demand for her skills and an opportunity to earn money for her sons when they went to college and then started families, Bishop founded Life Files Professionals to manage documents and organize offices, apartments, and computer files. The business is evolving as she is. Bishop recently began offering concierge services for older adults and family caregivers. She researches long-term care options, organizes health records, and arranges grocery orders and deliveries. All of these services can be done remotely, which is more important since she turned 80 this year.” READ MORE

THE 21 HATS PODCAST: DASHBOARD

A Business Owner Takes a Sabbatical: This week, Kurt Wilkin discusses what he’s learned about selling businesses and how he’s thinking about what he might do next. An entrepreneur, an investor, a mentor, and a former business owner who recently sold a recruiting firm, Wilkin tells us why his acquisition of the firm didn’t work out the way he hoped and how he managed to turn it around and sell it. Part of the problem, Kurt says, was that he jumped back into the game too quickly after selling his previous business. It’s a mistake he’s not going to repeat this time.

  • You can subscribe to the 21 Hats Podcast wherever you get podcasts.

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