YC-Backed Zen99 Makes Life Easier For Freelancers With Finance And Insurance Tools

Freelancers and contractors are a rapidly growing part of the workforce. Without benefits, however, many struggle with issues like figuring out how much of their earnings to withhold for taxes and finding insurance providers.

A new startup called Zen99 wants to help contractors with a free service. Backed by Y Combinator, Zen99 lets users sign up for health insurance, track earnings and expenses, and figure out how much to save for taxes on a single dashboard. It also offers advice through online guides at Zen99 University.

Zen99 was founded by Tristan Zier and Yan Lhert, who met while studying at UC San Diego. Zier was formerly a certified public accountant at Deloitte before helping to run the operations team at housecleaning service Exec (which has a workforce made up entirely of contractors) before it was acquired by Handybook. Yan was a software developer at several companies and often freelanced.

“Our goal is to provide contractors access to the same help that employees get from their HR departments: services like estimating and saving taxes, or getting health and dental insurance,” Zier and Yan said in an email.

The startup currently targets contractors who work on ridesharing or delivery platforms, as well as Web developers and people who provide creative services like graphic design or photography. Currently, its users include contractors from companies such as Uber, Lyft (one of Zen99 University’s first guides is called The Ultimate Guide to Ridesharing), DoorDash, and Caviar.

In the future, it plans to add tools that will help online vendors, including Etsy sellers, deal with inventory.


Zen99 makes finding insurance easier by only offering plans from insurers that it thinks offers the best coverage. Currently, it works with Blue Shield for normal health plans and Assurant for short-term medical insurance. This is meant to save freelancers the hassle of going through hundreds of plans themselves. Zen99 currently only sells health insurance in California, but plans to expand to other states and types of insurance.

The commissions Zen99 earns by selling insurance allows it to offer other features, including its tax management tools, for free.


Zen99 is acquiring users through partnerships with companies; referrals from contractors who already use the service; and content production, or the sharing of articles it produces for Zen99 University.

The dashboard is currently available online and through an Android app (and iOS app is coming soon).

The company sees Intuit Self-Employed, which helps contractors with tax estimates, non-profit The Freelancers’ Union, which plans to launch a national insurance platform soon, and insurance sellers like eHealth as its main competitors.

But Zier and Yan believes Zen99 will stand out because “there are high barriers to entry (taxes and insurance are highly regulated markets), our dashboard includes both taxes and insurance (and is free), and we have a history of startups (so plan to move fast).”

Zen99’s tax tools are currently available nationwide, while its insurance features are restricted to health insurance in California, but the startup will launch in other states and rollout new types of insurance within the next month.

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