Skip to content
Corporate Law Departments

CURIOUS MINDS: “I want to explore how technology can democratize the buying of legal services,” says PERSUIT’s Jim Delkousis

Rose D. Ors  CEO of ClientSmart

Rose D. Ors  CEO of ClientSmart

In the latest "Curious Minds" column, Rose Ors of Clientsmart speaks with Jim Delkousis, the founder and CEO of PERSUIT

In this column, Rose speaks with Jim Delkousis, the founder and CEO of PERSUIT, a tech platform that allows clients to streamline their legal RFP process, about democratize the buying of legal services, building something from nothing, and fighting your own imposter syndrome.

Rose Ors: Who are the business thinkers and leaders outside of the legal industry who have influenced you and your work?

Jim Delkousis: I have to admit that until I was in my mid-40s there was little that influenced me beyond a single-minded desire to succeed. I did not possess a “curious mind.”

As a son of immigrants, initially all that mattered to me was that I would never have to work in the factory floor conditions that my parents did for all of their working lives. My priority then became what career path to follow — I chose law. Upon joining a prestigious law firm in Australia, my energy was devoted to fighting my imposture syndrome. I decided to work twice as hard as everyone else just so I wouldn’t be found out!

Rose Ors: What changed?

Jim Delkousis: In 2007, I left the firm in Australia where I was a partner to open an office for DLA Piper in the Middle East. There were no clients, I did not know the language, and I did not know the law. When I left seven years later, I realized just how satisfying it was for me to create something from nothing, build a team, and have an impact.

In reflecting upon the satisfaction I had experienced at DLA Piper, I also realized that much of my reading for pleasure was the biographies of successful entrepreneurs such as Richard Branson, Jeff Bezos, and Bill Gates.

I was drawn to the adventure of creating something real and lasting from an idea. The pull was so strong that I began to ask myself: “Can I, too, experience the entrepreneur’s journey? Can I build something sustainable from nothing but an idea?” These questions began my search for the idea that became PERSUIT.

Rose Ors: That’s an apt name for your quest. What gave you the idea to start PERSUIT?

Jim Delkousis: I saw how the business world was becoming digitized at an increasingly fast rate and how it brought about a far more democratized and automated world for the consumer of products and services. The trend got me interested in exploring how technology could be used to automate and democratize the buying of legal services.

curious minds
Jim Delkousis, founder and CEO of PERSUIT

PERSUIT was born out of a deep-seated desire to be an entrepreneur and then following Norman Vincent Peale’s famous adage for success: “Find a need and fill it.”

Rose Ors: In addition to biographies, what other books have influenced or guided you?

Jim Delkousis: More than 20 years ago, I read The Road Less Traveled by M. Scott Peck. The book had a profound impact on me. The book’s first line is one I go back to often when I am overwhelmed: “Life is difficult.” I also share the line when I advise others who are struggling.

For me, beginning with the premise that life is difficult for everyone helps me frame the challenges I face.

Another great book is The Undoing Project: A Friendship That Changed Our Minds by Michael Lewis. The book delves into the work and friendship of the two men who invented the field of behavioral economics, Daniel Kahneman and Amos Tversky. Lewis details how their Nobel Prize-winning theory gave us a new understanding of what influences and drives people to make decisions. Reading the book gave me a deeper understanding of how people make buying decisions.

We continue our monthly column, Curious Minds, created by Rose Ors to tap into the minds of legal innovators, disrupters, and out-of-the-box thinkers to learn what influences and inspires their work.

One must-read book for every entrepreneur is by Ben Horowitz, The Hard Thing about Hard Things. Horowitz is the co-founder of Andreessen Horowitz, one of Silicon Valley’s most successful venture capital firms.

I came upon the book two years into launching PERSUIT, and I appreciated how Horowitz is straight about how hard it is to start and build a new software business. His candor — like Peck’s — grounds me in the knowledge that what I have experienced is not unique to me. Horowitz’s single page “About the Struggle” quoting from Karl Marx’s “Life is struggle” is the most powerful page I think I have ever read.

As I was reading the book, I found myself saying — sometimes out loud — “That is a problem I’m facing right now” or “That has happened to me.”

Rose Ors: What fuels your creativity?

Jim Delkousis: If you ask my kids if I am creative, they will keel over with laughter. I am the least creative person in the world. What I am is a grinder. I have always worked extremely hard at everything that matters to me. But creative, I am not.

Rose Ors: I will push back a little on this, because I know firsthand that launching a business requires creativity. Not creative in the way an artist is creative, but creative or innovative in how you think through problems and harvest opportunities. The process requires creative thinking, doesn’t it?

Jim Delkousis: Thinking in those terms, I studied the broader market trend, analyzed it, and applied it to the market I knew — with a twist. That was the creative process that led to the idea of PERSUIT. I guess you can call it creative copying.

Rose Ors: Now for the final question: What is a big-picture question facing the legal industry?

Jim Delkousis: For corporate law departments, a critical question centers around digital innovation. These departments acknowledge how fast their companies are changing under the banner of digital transformation. The question that looms largest for most legal teams is, “What does that mean for us?”

One way law departments are answering the question is by looking at technology-based solutions. But there are so many tech providers that the legal team is getting bombarded with options. All these options — some of which have not been battle-tested — leave the legal team confused about what tech they need and how that tech will integrate with the rest of the business.

Another broader question is: What will automation and artificial intelligence mean for lawyers’ role in society in the next 10, 20, or 30 years? Similarly, how will the legal industry — law schools, the courts, law firms, corporate law departments, and legal service companies — respond?


This interview has been edited and condensed by Rose Ors.

More insights