Fifteenth

Fifteenth envisions a future where the complexities of personal tax planning are transformed into seamless, personalized experiences tailored specifically for the technology sector. We are building a platform that combines cutting-edge AI-driven automation with the trusted expertise of dedicated human CPAs to deliver clarity and confidence during tax season.

Our mission is to simplify and modernize tax management by leveraging innovative technology to create proactive, tailored tax strategies that address the unique challenges of equity compensation and tech industry investments. We aim to empower tech professionals—founders, investors, and executives—to navigate their financial futures with greater ease and foresight.

By integrating deeply with leading financial and HR platforms and providing unlimited expert guidance, Fifteenth is creating a new standard in tax planning that prioritizes individual complexity and delivers transparent, expert-driven service through an intuitive digital experience.

We've been watching Fifteenth since they launched in 2024, and honestly, they're tackling one of the most painful problems in tech: getting your taxes done when you've got RSUs, ISOs, and a portfolio that looks like alphabet soup. The founding team gets it—CEO Ankur Dahiya and Chief Tax Officer Laura Moreno both lived through the frustration of traditional tax prep that just wasn't built for tech compensation.

What caught our attention right away was their flat-fee approach. No more hourly billing anxiety or surprise charges when your CPA discovers you've got three different equity grants and some crypto on the side.

The AI-Human Balance Actually Works

Here's where Fifteenth gets clever: they're not trying to replace CPAs with robots or stick you with pure automation. Instead, they've built an AI-powered document vault that organizes your financial life, then pairs you with actual tax experts who specialize in tech industry complexities.

We tested their integrations with platforms like Carta, Robinhood, and Workday—they're genuinely one-click simple. No more hunting down 1099s or trying to explain stock option exercises to someone who's never heard of a tender offer.

Built for Tech Money Problems

The real test came when we looked at their equity compensation handling. Fifteenth doesn't just file your taxes; they do proactive quarterly planning and scenario modeling. If you're facing an IPO or considering exercising options, they'll walk you through the tax implications before you make expensive mistakes.

Their team includes folks from PwC and other top-tier firms, so they're not learning on your dime. That matters when you're dealing with AMT calculations or planning around liquidity events.

Who Should Consider Them

If you're a founder, executive, or tech employee with complex equity compensation, Fifteenth makes sense. They're also solid for investors juggling multiple portfolios or anyone who's tired of explaining their Coinbase statements to confused accountants.

The $8.25 million seed round they just closed tells us they're serious about scaling, which is reassuring when you're trusting someone with your financial future. We're curious to see how they handle the inevitable rush of new clients as tax season heats up.