FlyFin Profile

FlyFin logo.

FlyFin is a fintech startup leveraging the power of artificial intelligence (AI) to help users prepare and file taxes. 

Founders Icon Founder(s): Jaideep Singh
Founded in Icon Founded In: 2020
Industry Icon Industry: Fintech
Location Icon Location: San Jose, CA

Interview With Jaideep Singh

Describe your product or service:

“FlyFin is a fintech company that offers a human plus AI-powered tax prep and tax filing service. FlyFin offers the first AI-based tax engine that combines the human expertise of real CPAs, resulting in a powerful, automated solution that eliminates 95% of the work required for 1099 self-employed individuals to prepare their taxes. FlyFin’s mobile-first app is ideal for self-employed people, freelancers, gig workers, and creator economy free agents, who often have greater tax complexities. FlyFin helps individuals maximize self-employment tax deductions and income tax refunds.” 

Describe your company values and mission:

“FlyFin is committed to automating and simplifying the tax filing process of its customers. Since launching, FlyFin has continued to extend the functionality of its product. Over the past year, the company has been building a comprehensive resource center for tax preparation dedicated to the needs of self-employed people and freelancers.”

How are you funded? I.e. type of funding, number of funding rounds, total funding amount.

“$8 million in seed and pre-Series A funding.”

How did you come up with and validate your startup idea? Tell us the story!

“The idea emerged when I was looking to start my next company, thinking of the list of consumer pain points that exist and what software could solve them. I'd spent over a year vetting various ideas when it started to get close to time to file my taxes again, and this idea that I had before came up again because I was stressing out about putting together a spreadsheet to hand over to my CPA, which is a real pain. I truly hated dealing with taxes and was certain that most people feel the same way.

I started thinking about the parts of the process that can be automated, so I could stop stressing out every year. I also thought about how many people could use this, and the number is massive. That, to me, was important because I was not just trying to build another software company. I wanted it to have a serious impact on people’s lives.

The solution that came to mind also needed to be not just slightly better but revolutionary because, in my experience, people don't change their behavior unless something is radically different. The third and most important piece was that even though I have experience in AI and machine learning, and building companies around them, I really needed a strong cofounder steeped in these technologies. My co-founder, Sachin Rajendra, is an AI/ML expert, especially when it comes to information retrieval, entity extraction, NLP and computer vision. When I met him, I realized we could build a killer team together and develop a market-leading product.”

How did you come up with your startup's name? Did you have other names you considered?

“We wanted a short memorable name that was also broad, so one afternoon Sachin and I sat down in front of a shared Google Sheet and hit upon FlyFin. I was surrounded by aviation my entire life, and flying is synonymous with speed, while a fin evokes the joy of gliding with speed, agility, and ease.”

Did you always want to start your own business? What made you want to become an entrepreneur?

“I've wanted to be an entrepreneur since I was a kid. I almost stopped going to college to help start a restaurant chain. But I liked the culture around software development and the environment of dedication I was already immersed in. I realized that I wanted to start a software business, which is a complicated industry, so it took me many years to develop the deeper product and business skills I would need – but starting my own company is what I always wanted.”

Did you encounter any roadblocks when launching your startup? If so, what were they and what did you do to solve them?

“To do something really game-changing, you need a really high-quality team. Without the best people, there's little chance of your company becoming a leader in that space. And of course, we also needed the capital. But not just any capital. We approached the top VCs in the industry, and fortunately, I've done this a few times before, so I knew that bar was high. 

 So Sachin and I solved for those two problems: a superb team and the right capital, problems all founders would probably cite. We basically surrounded ourselves with the best people and just pushed ahead.”

Feeling inspired? Learn how to launch your company with our guide on how to start a startup

Who is your target market? How did you establish the right market for your startup?

“FlyFin’s mobile-first app is ideal for self-employed people, freelancers, gig workers, and creator economy free agents, who often have greater tax complexities. 

We took time to fully understand the market and realized that the people facing similar pain points to those I face are people who have Schedule C income and expenses. That includes the entire gig economy, self-employed individuals, and freelancers of any kind.”

What's your primary marketing strategy?

“We reach users directly through digital media and through partnerships.”

How did you acquire your first 100 customers?

“Our first customers came from our network of friends and family, and we also picked up the phone and called a lot of new people. We presented them with a design on a smartphone that was clickable like an app, and they were hooked.”

What are the key customer metrics / unit economics / KPIs you pay attention to to monitor the health of your business?

“User satisfaction is the most important metric of all. We’re constantly measuring whether users are able to achieve what they came to FlyFin for. Are they able to get what they need and more in a way that is efficient, and are they happy with the experience? Most other metrics are derivatives of user satisfaction. Naturally, customer acquisition costs and positive unit economics are also crucial to the business being able to offer users the best experience.”

What's your favorite startup book and podcast?

“There is no single book or podcast. Gathering information and inspiration from a wide variety of sources and perspectives is essential to operate effectively and efficiently. One book, the biography on Steve Jobs, authored by Walter Isaacson, has some great lessons on innovation and leadership.”

Is there a tool, app, or resource that you swear by to help run your startup?

“Google Analytics continues to be a really valuable tool, as it is for almost any startup. Hotjar and user interviews are indispensable tools for us to provide our users with the best experience possible.”

What is something that surprised you about entrepreneurship?

“It is a 24/7 responsibility to keep the operation running, and that responsibility is to our customers, to our product, to our team, and to our investors. You can’t just take a vacation and unplug for two weeks – or even a week. You’ve got to be always on.”

How do you achieve work/life balance as a founder?

“I don't. In entrepreneurship, the balance is really a work balance. But when you get a few hours of life, grab every opportunity, no matter how small, especially spending time with friends and family.”

What is a strategy you use to stay productive and focused?

“Staying physically and mentally fit has played a huge role in my productivity and helped me stay laser-focused on goals. I work out regularly at the gym and do yoga, which is both energizing and calming. My Saturday evenings socializing with friends are just as important.”

When did you know it was time to quit your day job to focus on your startup?

“I made the decision a long time ago to never have a day job because I always knew this was the life for me.”

What was your first job and what did it teach you?

“It's a rollercoaster ride every day, so be prepared for that, but also try to adopt a mindset where you enjoy the ride rather than stressing out about it.”

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