Story of FlyFin- AI-powered tax preparation and filing service
Story of FlyFinStory
The story of FlyFin began when Jaideep Singh, who had
already founded other companies like SeeDoc and Spock, grew frustrated with the
complicated process of filing his own taxes. He realized that millions of
self-employed people, freelancers, and gig workers struggled with the same
problem. Preparing spreadsheets, handing them over to CPAs, and worrying about
missing deductions was stressful. That’s when the idea struck: what if he could
automate most of this painful process using AI?
A Meeting of Minds
Jaideep knew that he couldn’t build a game-changing product alone. He needed a
strong partner with deep expertise in artificial intelligence and machine
learning. That’s when he met Sachin Rajendra, an AI/ML expert skilled in NLP,
information retrieval, and computer vision. Together, they decided to build a
revolutionary tax solution, combining automation with the expertise of real
CPAs.
Naming the Vision
The name “FlyFin” was chosen in a brainstorming session between Jaideep and
Sachin. Jaideep, who had been surrounded by aviation all his life, thought
flying symbolized speed and agility. Adding “Fin” made it memorable, evoking
both finance and the smooth glide of a fin cutting through water. The name
represented their mission: making tax filing as fast and effortless as flight.
The Early Struggles
Building FlyFin wasn’t easy. The founders needed not only the best engineers
and product builders but also the right investors who understood their vision.
Fundraising was tough because they were aiming to disrupt a traditional
industry with a bold, AI-driven solution. Still, they pushed forward,
assembling a strong team and securing VC backing to bring their idea to life.
Identifying the Market
The founders realized that their ideal users were not large corporations but
self-employed individuals who faced unique tax challenges. Freelancers, gig
workers, and creators often deal with irregular income and multiple deductions,
making taxes even harder. FlyFin’s mobile-first app was designed specifically
for them, ensuring it could handle their complexities while being simple to
use.
First Customers and Early Growth
FlyFin’s first customers came from Jaideep and Sachin’s personal networks. They
tested the product using a clickable smartphone design, and people were
immediately hooked. Word spread quickly, and soon freelancers and gig workers
outside their circle began signing up. The ease of use and time savings made
FlyFin an attractive solution.
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Revolutionary Approach
Unlike traditional tax software, FlyFin used an AI-powered tax engine that did
95% of the work, with real CPAs reviewing the rest. This combination ensured
accuracy while saving users time and stress. The founders wanted FlyFin to be
more than just slightly better than existing solutions they aimed for a
revolutionary leap that would truly change behavior.
Customer Experience First
For the FlyFin team, the most important measure of success was user
satisfaction. They closely monitored whether users could get their taxes done
efficiently and whether the experience left them happy. All other metrics, like
acquisition costs or revenue growth, were seen as secondary. Keeping customers
satisfied was the foundation of their strategy.
Challenges of Leadership
Running a startup like FlyFin required nonstop effort. Jaideep admitted that
entrepreneurship was a 24/7 responsibility, leaving little time for vacations
or switching off. Yet he embraced the challenge, knowing that his
responsibility extended not just to his investors, but also to his team,
product, and customers.
Life as an Entrepreneur
Jaideep always knew he wanted to be an entrepreneur. As a child, he almost
skipped college to help start a restaurant chain. Eventually, he chose software
because it was an industry that demanded constant dedication and innovation.
After years of building his skills, FlyFin became the company where his passion
for entrepreneurship met a massive consumer need.
Tools and Strategies
To stay productive, Jaideep relied on physical fitness, yoga, and small moments
with family and friends. For the business, FlyFin used tools like Google
Analytics, Hotjar, and user interviews to track performance and improve user
experience. These resources allowed the team to constantly refine the app and
better serve their growing community.
FlyFin’s Expansion
Over the years, FlyFin extended its product features and built a comprehensive
tax resource center tailored to freelancers and self-employed workers. Even as
the team size fluctuated with 29 employees by August 2024, down 41% from the
previous year the company continued improving its service and maintaining its
focus on customer needs.
A Mission for the Future
FlyFin’s goal has always been to automate and simplify the financial lives of
US consumers, especially self-employed individuals. Backed by serial
entrepreneurs who have created over $1.5 billion in enterprise value across the
US and India, FlyFin is not just a tax app it is a mission to revolutionize
financial management for millions of people.
Timeline of FlyFin Story
- Childhood
& Early Dreams (1990s): Jaideep Singh dreams of becoming an
entrepreneur.
- Education
(2000–2002): Jaideep earns his MBA from Wharton after studying
computer engineering.
- Early
Career: Jaideep founds SeeDoc and Spock, gaining startup experience.
- 2019:
Jaideep starts Idea Junction, incubating early-stage companies.
- 2020:
FlyFin AI is officially founded by Jaideep Singh and Sachin Rajendra.
- 2021–2022:
The product evolves, focusing on freelancers and gig workers.
- 2023:
FlyFin expands functionality and builds a tax resource center.
- August
2023: Employee count peaks before later declining.
- August
2024: FlyFin has 29 employees, down 41% from the year before.
- Present
(2025): FlyFin continues serving self-employed users with its AI+CPA
tax solution, aiming to make tax filing effortless.
