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Apprehensive You'll Go Broke If You Can't Work In Your Enterprise? A Startup Affords Options – jj

Apprehensive You'll Go Broke If You Can't Work In Your Enterprise? A Startup Affords Options


Most one-person business owners love the freedom of being their own boss but live with a harsh tradeoff: If they can’t work because they’re sick or injured, they don’t get paid.

Trupo, founded last year by Freelancers Union founder and MacArthur Foundation “genius” fellow Sara Horowitz, is trying to address this gap in the marketplace. The startup piloted a short-term disability offering in Atlanta, priced at $30-$50 a month, when it launched last year. It is now introducing three new insurance products in New York State.

The Trupo platform, focused on bringing economic security to freelancers, has begun selling accident insurance, dental insurance (with a vision insurance add-on) and specified disease and cancer insurance. It has collaborated with Colonial Life & Accident Insurance Company, a large provider of voluntary benefits.

Freelancers Union founder Sara Horowitz is tackling economic insecurity for freelancers at Trupo, a platform that offers short-term insurance. It is rolling out several types of insurance in New York State.


Trupo plans to roll out the products across the U.S. in the coming year. The company is funded by the Silicon Valley venture capital firms Sequoia Capital and Ripplewood and the impact investor Radicle Impact. It is partly owned by the Freelancers Union, based in Brooklyn, N.Y., an early pioneer in bringing health insurance to freelancers.

Many freelancers wish they had income protection in the event they are sick or injured but disability insurance is hard to come by. Long-term disability insurance for freelancers can be prohibitively expensive. Short-term disability insurance is generally only available through employers. 

“We are designing this for creative professionals, getting them the benefits that make sense for them,” Horowitz says. “The biggest problem for this new workforce is the short-term. That’s really what we’re focusing on—helping people where their pain points are.”

The cost of Trupo’s insurance is customized to the freelancer, depending on factors such as their activity level at work. Freelancers must answer five questions on the website to get their rates.

Trupo enables freelancers to pay for the insurance it sells by credit card and does not require purchasers to set it up as a formal company benefit that is deducted from a payroll. “It’s made to be really simple,” says Horowitz.

In addition to the Freelancers Union, Trupo has partnered with Coworker.org, a provider of education and training for freelancers; the Author’s Guild and the Graphic Artists Guild to roll out the product.

Many gig workers are economically vulnerable because of unsteady pay and a social safety net that barely takes into account the rising number of people doing freelance, contract and gig work. This added vulnerability can make it hard for a freelancers to cope with unexpected expenses, such as the substantial bills that often come with medical treatment in today’s era of high-deductible health insurance plans.

Research released in May by the Federal Reserve Board of Governors found that for those who earn their primary income from gig work, 58% would have difficulty handling an unexpected $400 expense, compared to 44% of those who do gig work for supplemental income and 39% of all adults.

Perhaps the government will someday extend the social safety net to the millions of Americans who make all or part of their living as freelancers, but Horowitz doesn’t want to wait until that point.

“We have to be able to start right now,” she says. “We have to start building this next safety net and showing what it looks like. That’s when the next role of government will be to help build this out.”

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