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The Serial Entrepreneur: Is There Life After 50?

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This article is more than 8 years old.

It’s not often that people start businesses after leaving a paying job well into in their 50s. It’s even more unusual to become a serial entrepreneur. But meet Jan Hively, now age 83. Hively has launched four small businesses – all in the not-for-profit arena (She calls herself a “social entrepreneur.”)

The takeaway? Do what you know. Hively, who now lives in Yarmouth, Mass., was able to parlay her experience working in the public and private sectors – at the University of Minnesota,  for instance – building volunteer networks and finding grant money. She had to eat what she killed – i.e. raise money to survive – so being an entrepreneur worked out well.

“I never really retired,” she says. “I found a freedom to follow my own vocational calling I had never experienced before.” More on Hively – who is on to business number four now - and what startups, and what aspiring small business owners, can learn from her experience:

What She Runs: In 2013 Hively launched, with 69-year-old Moria Allan, the “Pass it On Network,” which, among other things, helps Baby Boomers find work that is “meaningful and also happens to generate income.” The organization, which includes a website, is still in its infancy and seeking funding to expand.

What She Ran: In 1989 Hively left her job as deputy mayor in Minneapolis, launched what was then called The Youth Trust; the organization helped other youth-oriented not-for-profits. A decade later when Minnesota Governor Jesse Ventura – yes, the former pro wrestler – reorganized the agency that was funding her work, Hively shifted her focus and “earned a doctorate in aging.” The University of Minnesota ponied up $40,000 to launch Hively’s Vital Aging Network (VAN) in 2001. She eventually raised close to $1 million for VAN, which helps 50-somethings with things such as mapping out their retirement.

Other Startups? In 2007 Hively met David Buck, then 47, who was just laid off for the third time. They cofounded an organization called SHIFT, which set up weekly meetings for boomers in local coffeehouses as well as  a website and program that was designed to help folks become entrepreneurs. They created an all-volunteer organization with a 15-member board and raised funds from banks such as Wells Fargo .

How It Has Worked Out: Hively likes to point out that each organization she launched is alive and well with varying levels of funding.

What’s Changed After 50: “I make better judgments as I integrate expanded experience and learning,” she says. “But I have more difficulty with what should be simple marketing...because everything seems more complex. All shades of grey. No black and white.”

What She Learned About Herself: After building her first non-profit, Hively discovered an interesting thing: She was a builder, not a maintainer. “I am a start-up planner who is happy to melt away when talent and resources and structure are in place for follow-through,” she says.

Lessons for Others?

  1. The strategic selection, and cultivation, of partners pays off.
  2. No one will stick around who does not have a personal vested interest in the work.
  3. The most important asset for an entrepreneur is direct, open and honest communication – and effective follow-through.

What’s Next : “My mantra,” she says, “is meaningful work, paid or unpaid, through the last breath.”