Cherie Kloss and the Unexpected Value of Starting Over

Before Cherie Kloss built a company around booking work, she had an idea for booking hotel rooms by the hour. It went nowhere. She did not know the hotel business well enough to make the idea practical. So she took the booking concept into a field she understood, and the business that became SnapNurse began to take shape. A failed idea had found a more useful address.

There is something pleasingly untidy about this origin. The company did not arrive as the inevitable final step of a perfectly arranged résumé. Kloss had already spent years making television. She was a single mother. She started SnapNurse at 49. Later, after leaving the chief executive’s job, she wrote a book called Life Is Long. The title sounds almost impolite in a culture that likes its founders young and its careers easy to explain.

Her argument begins with an awkward possibility: becoming good at something need not oblige you to do it forever. Experience can finance another beginning. It can also become the excuse for never attempting one. Kloss’s career is interesting because she keeps putting that proposition to work, with actual companies and actual responsibilities attached.

A bakery, a scholarship, a different life

At 15, Kloss was emancipated from her family. Her father, a Korean immigrant, returned to Seoul for a job opportunity; she stayed in Southern California. She moved in with a friend, worked full time at a bakery, and finished school. A scholarship took her to Westmont College near Santa Barbara. After the demands of supporting herself as a teenager, college felt unusually carefree.

The details resist the usual tidy fable about precocious entrepreneurship. A bakery job is work that needs doing. School still has to be finished. Before there was any glamorous language for her willingness to begin again, there was the practical business of getting through the week. That early independence gives the later career changes a different texture. Starting over had consequences long before it became a book subtitle.

She graduated from Westmont in 1990 after studying biology and went on to earn a master’s degree at Emory University. Years later, the connections made at those schools would become part of her working life again. Her education supplied knowledge, of course. It also introduced her to people whose abilities she would remember when she had a company to build.

MLC, as in “mid-life crisis”

In 2006, Kloss met a producer for A&E Networks and became interested in making reality television. Her production company, MLC Media, operated from her house. The initials stood for “mid-life crisis,” which is a refreshingly economical way to acknowledge a career change before somebody else gives it a less flattering name.

Over the following decade, she sold 38 shows, with eight making it to air. The subjects included Kentucky backyard oil prospectors and Alabama gold miners in the Amazon. Television gave her a rather different inventory of things to think about. An unconventional résumé can look abstract on a conference program; backyard oil prospectors are usefully specific.

That period also matters because it complicates the idea that reinvention requires becoming inexperienced in every respect. A new business brings unfamiliar rules, but the person entering it still has a history. Kloss’s television years belonged to her when she started a software company. Selling ideas, attracting attention, and finding people willing to work on something were already part of her life.

Try the small version first

SnapNurse launched in 2017. Kloss brought in Jeff Richards and Kirk Martin to help build the business. The initial problem was familiar to her: finding an assignment involved telephone calls, paper schedules, missing information, and repeated administration. There was an opportunity to make booking work less cumbersome. The promise was understandable without a seminar on software.

She tested the idea using a third-party platform under her own brand. That gave her a way to learn which features customers needed before spending heavily on a system of her own. It was an economical apprenticeship in the product. You can argue about a feature for a very long time in a meeting. People trying to use it tend to shorten the discussion.

The payment experience became another part of the product. The company developed infrastructure for daily W-2 payments when an existing solution did not meet its requirements. That work produced Paymint, an additional business line. A nuisance inside one company had become something other companies might need, too.

By 2022, SnapNurse had reached second place on the Inc. 5000. The number deserves a pause. A business founded by someone approaching 50 had appeared near the top of a list routinely associated with the cult of the youthful founder. Kloss’s age at launch was part of the circumstances she worked with. The ranking makes it difficult to treat those circumstances as a reason she should never have tried.

The people she already knew

As SnapNurse expanded, Kloss recruited women she had known since Westmont: Judy Dimeny Messer, Sabrina Agnew Stark, Julie Herrscher Sibley, and Heather McCaffery, whose husband was also a college contemporary. Some had spent years raising children. She offered remote work and trusted them with a growing business.

It is a concrete answer to a familiar recruitment problem. A long absence from paid work can make a résumé harder to sell. Kloss had information that the résumé could not supply: she knew these women. She knew their capabilities and believed they would work hard. Their time away did not erase that knowledge.

She also recruited from her Emory class. The story of her team therefore runs back through classrooms and friendships, rather than beginning at the moment a vacancy was advertised. Her account of the company’s expansion gives those relationships real weight. The founder’s achievement included remembering who else might be capable of a new beginning.

“I am obsessed with finishing things”

Cherie Kloss, on her working habits

Her own description of her habits adds a useful counterweight to all this career changing. She likes to finish things. The appetite for another chapter coexists with a concern for getting the current work done. Without that second quality, reinvention could become a very elegant name for abandoning projects halfway through.

Eventually, hire someone who can take the meeting

Kloss’s advice to other founders is practical about the organization around them. In a 2022 essay, she urged women entrepreneurs to assemble experts in areas where their own knowledge was thin, including technology, accounting, and human resources. She also recommended strong middle managers who could release the founder from an overcrowded calendar.

There is a recognizable progression here. At the beginning, you may have to learn enough to do almost everything. Later, doing everything becomes a way to hold up the company. Her advice asks founders to acknowledge their limitations twice: first by learning, then by finding capable people to whom they can entrust the work.

In July 2022, SnapNurse announced that she would step down as CEO, with Richards becoming interim CEO. The announcement said she would retain her board seat and founder role. SnapNurse became SnapCare in 2023. Her connection to the business remains central to her public identity, but the chief executive’s chair was a job she could leave.

Today, CryoFuture lists Kloss as chairman of its board. Her professional profile also describes an advisory role. Moving from running a company to helping guide one changes the daily assignment. It lets experience travel into another organization without requiring the same title, or the same relationship to every decision.

A career guide for people with a school bus to catch

Life Is Long: How to Reinvent Your Career Every Decade appeared on August 6, 2024. Published under her full name, Cherie Soyoung Pae Kloss, it gathers her argument for repeated career changes into a guide for readers who feel stuck. Women are its particular audience, including women whose obligations make the usual advice sound rather remote.

The book’s introduction takes aim at elaborate morning routines. A mother getting children fed, dressed, and onto a school bus has limited use for instructions to spend the first three hours of her day on self-improvement. Kloss notices the missing person in that arrangement: whoever is supposed to find the children’s backpacks while all this magnificent personal development takes place.

Her book approaches career change through discovery, preparation, education, and achievement. That sequence leaves room for the unglamorous middle of a transition. Interest is a beginning; acquiring skills and preparing to use them take time. A new career can be considered deliberately, even when the desire for it first arrives as restlessness.

In her writing about careers, Kloss describes working life as cyclical. A choice made in your twenties need not govern everything that follows. That is an appealing proposition for someone with an established career as well as someone dissatisfied with one. Success can make a decision to change harder to explain. It can still be a decision worth considering.

The appeal of Kloss’s story lies in its specific, slightly unruly parts: the bakery, the home production company, the hotel app that failed, the college friends who returned to paid work. Each belongs to a person making choices with the knowledge and resources available at the time. She has since given that process a book title. Long before that, she was finding out what else she could do.