Zen99

Tax and insurance tools for independent contractors

InactiveFinTechInsuranceMountain ViewY Combinator

Updated: Dec 4, 2025 ·

About

Our mission is powering prosperity around the world. We build intuitive web, mobile, and cloud solutions that generate more money, more time, and more confidence for 46+ million people. Leveraging big data insights, machine learning, and powerful automation, we help consumers, small business owners, and the self-employed achieve their dreams of prosperity.

Whether you work on our product and technology teams or in any role across the globe, you’ll play a part in designing and launching industry-leading products like Mint, TurboTax and QuickBooks in an agile environment with fast moving teams. Learn how your ideas will shape our ecosystem of products and make a giant impact.

Our culture and entrepreneurial spirit have earned us a spot on Fortune’s “Best Companies to Work For” year after year, as well as many other recognitions across the globe. Join us in powering prosperity around the world.

Career Areas: Software Engineering, Product Management, Mobile, UX / User Design, Data, QA, IT, Marketing, Sales, Finance, Tax, and more.

Financial History

Total Raised

N/A

Valuation

N/A

Financial History

Total Raised

N/A

Valuation

N/A

Leadership Team

Key people at Zen99.

Leadership Team

Key people at Zen99.

Deep Dive

High-Level Overview

Zen99 was a startup that built a free financial management platform tailored for independent contractors and freelancers, focusing on simplifying tax withholding, health insurance enrollment, and expense tracking through a unified dashboard[1]. It primarily served gig economy workers such as rideshare drivers (Uber, Lyft), delivery personnel (DoorDash, Caviar), and creative freelancers like web developers and graphic designers[1]. By addressing the lack of traditional employee benefits and financial guidance for contractors, Zen99 aimed to provide services akin to an HR department for independent workers, helping them estimate taxes and secure insurance coverage[1].

Origin Story

Founded in 2013 by Tristan Zier and Yan Lhert, who met at UC San Diego, Zen99 emerged from their combined experiences: Zier was a CPA at Deloitte and had operational experience managing a contractor workforce at Exec, while Yan was a software developer and freelancer[1]. Their insight into the challenges faced by contractors in managing taxes and insurance led to the creation of Zen99. The company was accepted into Y Combinator and raised $2.6 million from investors including SV Angel and Crunchfund[1][4]. Despite early traction and a growing user base, Zen99 closed its operations in 2015, returning remaining capital to investors[4][5][6].

Core Differentiators

Integrated Dashboard: Combined tax estimation, earnings and expense tracking, and health insurance enrollment in one free platform, unlike competitors who focused on either taxes or insurance alone[1].
Targeted User Base: Focused specifically on gig economy contractors and freelancers, addressing their unique financial and insurance needs[1].
Regulatory Navigation: Tackled the high barriers to entry in regulated markets like insurance and taxes, offering a streamlined user experience[1].
Educational Resources: Provided online guides through Zen99 University to help users understand ridesharing taxes and insurance options[1].

Role in the Broader Tech Landscape

Zen99 rode the wave of the rapid growth of the gig economy and independent contracting, a workforce segment underserved by traditional financial and insurance products[1]. The timing was critical as more workers sought flexible employment but lacked access to benefits and tax support. Zen99’s approach highlighted the need for integrated financial tools tailored to non-traditional workers, influencing how startups and fintech companies think about servicing this expanding segment. Its closure underscored the challenges startups face in highly regulated markets despite clear demand.

Quick Take & Future Outlook

Although Zen99 ceased operations in 2015, its mission to empower independent contractors with financial and insurance tools remains highly relevant as the gig economy continues to expand. Future solutions will likely build on Zen99’s integrated approach but will need to navigate regulatory complexities and scale sustainably. Trends such as increasing contractor protections, digital insurance marketplaces, and AI-driven tax assistance will shape the evolution of this space. Zen99’s early vision set a foundation for ongoing innovation in supporting the financial health of independent workers.

Sources

Frequently Asked Questions

Who founded Zen99?

Zen99 was founded in 2014 by Yan Lhert (Founder/CTO) and Tristan Zier (Founder/CEO).

Frequently Asked Questions

Who founded Zen99?

Zen99 was founded in 2014 by Yan Lhert (Founder/CTO) and Tristan Zier (Founder/CEO).