Teaming Up With My Immigration Lawyer to Reinvent Immigration Software

My immigration lawyer handed me a dozen pieces of paper and a pencil. “These six pages are about you, those six are about your wife,” he explained. “When you’re done, hand them back and I’ll start preparing your immigration forms.”

I was dumbfounded. Did immigration really require this much paperwork? Was it really this archaic?

Out of one jungle, into another

The year was 2015. My US citizen wife and I had just escaped with our lives from a honeymoon-turned-jungle-misadventure in the Amazon. After twelve years bouncing around an alphabet soup of nonimmigrant visas, I was finally eligible to take my relationship with the United States from on-again-off-again to long-term.

My wife and me on our ill-fated jungle misadventure.

However I soon found myself again lost in a jungle, this time one of obliquely named forms and tough legal questions. A JD from Penn Law and two years practicing at a corporate firm in New York couldn’t help me reason my way through the mire. I needed an expert.

Surely, there was a better way

I chose James from the dozen lawyers I interviewed, because he had an encyclopedic knowledge of immigration law. He knew every nuance and every rare exception. So I was surprised when he handed me that stack of pages to complete. I hired him to guide me through the maze, not to do data entry.

James was a great lawyer with a not-so-great intake process.

I also had better things to do than scratch the contents of my life in lead on paper, a medium long since abandoned in other sectors of the economy.

Surely, there was a better way.

At my next meeting with James, we began searching for a solution. There were incumbents — some required downloading their software on a CD ROM, others were a bit more modern. But we couldn’t find the aesthetic, passion-inspiring, shiny-new-toy innovation of modern cloud-based web applications.

We were looking for a solution users loved. Failing to find it, we teamed up, quit our jobs and built one ourselves.

From the outset, we focused on making it easier to move data from clients to government forms. It didn’t make sense to me that a client would spend hours entering data into one form, only for a lawyer or paralegal to manually move the data into other forms.

James and me in the early days.

We devised an online questionnaire that asked clients simple questions, coupled with a mapping algorithm that digitally moved the data into the right places on the right forms. The goal was to free immigration lawyers up to do the work clients really needed from them: thoughtfully applying expertise to complicated legal questions.

The Minimally Viable Product

In the startup world, the conventional wisdom is to build the simplest possible prototype of your idea — a minimally viable product — and test it with real users before building a comprehensive solution. The goal is to invest the least amount of time possible before determining whether anyone actually likes your product. It’s a wise approach, and we chose to follow it.

My son and me coding the minimally viable product (he wasn’t very helpful)

The first version of Docketwise was minimal to the extreme. There were no notes, tasks, contacts, documents, case tracking, matters or PDF Forms. We didn’t have integrations, court forms or humanitarian applications. All it could do was prepare family-based green card applications based on answers to simple questions.

The goal of a minimally viable product is to be minimal, but not bad. I think some startups get this wrong, polluting the internet with half-baked prototypes. While Docketwise 1.0 did not do much, James and I obsessively crafted it to near-perfection. It was minimal, but it was also beautiful, easy-to-use, and highly accurate. We felt confident users would love it.

That confidence didn’t help ease the butterflies as we walked into the first of ten demos that we scheduled with local immigration lawyers in Philadelphia. “Pretty cool!”, the first lawyer told us as we showed off our MVP. “Maybe I’ll subscribe when it has more features.”

We exited the office dejected but hopeful that the next demo would go better. Our hope was well placed — every one of the next nine attorneys subscribed on the spot. Our little MVP had achieved a 90% conversion rate in its first week.

Our little MVP had achieved a 90% conversion rate in its first week.

With great data to show investors, we dedicated ourselves to a quick round of fundraising, then jumped back into building out the product. In early 2017, we released Docketwise 2.0 with a slew of cool features. It had more forms, matters and practice management features. It could track priority dates and pull case statuses from USCIS. It wasn’t yet the product we’d dreamed of, but it was close. In 2019, we launched Docketwise 3.0, the comprehensive set of immigration tools we’d imagined three years earlier.

“Docketwise completely changed our practice”

Today, Docketwise powers the offices of over a thousand attorneys and paralegals. It’s used by solos, large firms, nonprofits and everything in between. We’re honored by the privilege and thrilled by the feedback we receive every day.

Create breakthrough technology instead of incremental improvements

Serial entrepreneur and startup guru Peter Thiel argued that startups should create breakthrough technology instead of incremental improvements.

I agree and that’s why, of all the positive feedback we receive, the one that hits home the most is when users tell me “Docketwise completely changed our practice.” We’re striving not just to improve the practice of immigration law, but to fundamentally change it for the better.



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