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Rudy DeFelice of Keesal Propulsion Labs: “The world is already on a digital transformation journey, powered by technology”

The world is already on a digital transformation journey, powered by technology. We define our lane as connecting technology to the needs of people in a way that has business impact and helps corporate legal departments become influencers. I would say our work is more in keeping with the trend the world is experiencing, rather […]

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The world is already on a digital transformation journey, powered by technology. We define our lane as connecting technology to the needs of people in a way that has business impact and helps corporate legal departments become influencers. I would say our work is more in keeping with the trend the world is experiencing, rather than changing it, per se.


As a part of our series about cutting edge technological breakthroughs, I had the pleasure of interviewing Rudy DeFelice.

Rudy DeFelice, is co-founder and CEO of Keesal Propulsion Labs, a digital transformation company serving the law departments of the Fortune 500. Rudy is an attorney, technology entrepreneur, TEDx speaker and best-selling author. He is an alumnus of Harvard Business School and the University of Connecticut School of Law and holds a BS in Computer Science.


Thank you for joining us! Can you tell us a story about what brought you to this specific career path?

I’m in a bar on Wall Street with some colleagues from my international law firm. It was a high-pressure place, where people lived and breathed their jobs and frequently felt crushed by the relentlessness of it. One of my friends said, “you never seem to be burdened by Big Law; you seem to leave your job at the door when you leave”.

I spent the rest of that night wondering why that was. Why was I different than my colleagues on this? I wished it was some super power or sign of enlightenment. But in a moment of insight, it came to me. I just didn’t care about it enough. I was successful, but not inspired. Fighting with other lawyers, generally good people, over which rich company got more money wasn’t who I was.

I decided I wanted to create things. So, I looked at the world I knew — lawyers and legal organizations, identified a few areas where tech was needed, and built a company. I expected to do it for a few years and go back to a grown-up job. But at some point, I realized that building companies, inventing products and leading teams, was what I was born to do. That has been my path ever since.

Can you share the most interesting story that happened to you since you began your career?

My first startup, Practice Technologies, built a knowledge management product focused on lawyer work product for law firms. I was evangelizing the need for this technology for a few years through one on one conversations, speaking engagements, the basic slow, trench warfare of introducing a new category.

After a few years of slow growth, while our confidence was already shaken, the largest company in our space, a 6B dollars giant, announced a competing product. We thought we were done for, after barely starting. They’d never even heard of us and were sure they would run the table on the market.

We had to decide to either fold the tent and go back to real jobs or not. Our team included married guys, guys with kids and mortgages and responsibilities. It was a scary time. But we believed in each other and everybody decided to wait it out a little longer.

Instead of killing us, the competitor saved us. With all their marketing muscle and credibility, they taught the market that they needed a product in this category. Then, our phone started ringing. Once convinced of the category, folks remembered meeting with us, seeing me speak at a conference, meeting one of my team members. So, they gave our product a look. Although we didn’t reach the market as broadly as our competitor, we’d been building the product longer. So, it was better. Then we started getting deals.

In this experience I developed a different view of competition. I don’t fear it — I crave it. Competition creates a market. It also drives you to be your best. This approach has helped me introduce new products, but also develop great relationships with competitors, where I can approach a market as part of a larger mission to solve a problem and serve a customer segment rather than it being about beating the other guy.

Can you tell us about the Cutting edge technological breakthroughs that you are working on? How do you think that will help people?

I believe automation will empower people to have better lives. My company is focused on digital transformation — helping companies transition to a digital world, where information is available seamlessly, everywhere. The first order value is that people are lifted from some of the drudgery in their jobs, which the technology takes over. I’ve seen that once the weight of menial burdens is removed, peoples’ creativity flourishes. The second order benefit is that we can weaken this construct of geographic limitation. Companies can recruit talent globally and people can interact meaningfully from anywhere.

We’re focused on corporate legal departments, who used to be identified with saying “no” to innovation. However, now they are seen as leaders in managing information. Corporate legal departments were always pretty good at managing information. However, now, in an information economy, it is recognized that information is a strategic asset. So, we’re helping corporate legal departments become strategic leaders in this new environment. We’ve done this with numerous legal departments and it’s rewarding to see departments and careers transform.

How do you think this might change the world?

The world is already on a digital transformation journey, powered by technology. We define our lane as connecting technology to the needs of people in a way that has business impact and helps corporate legal departments become influencers. I would say our work is more in keeping with the trend the world is experiencing, rather than changing it, per se.

Keeping “Black Mirror” in mind can you see any potential drawbacks about this technology that people should think more deeply about?

When it comes to technology and automation generally, the immediate concern is always that it will reduce jobs. That is a legitimate issue for a society of course. However, that risk is not in keeping with history and the human experience.

In the last 100 years we’ve experienced a revolution in agricultural practices through mechanized farming, an industrial revolution and currently an information revolution. Each of these was driven by technology and every time people worried that it would reduce jobs. But in all cases, there were more jobs. Some jobs were different of course. One could easily argue that the new jobs are better. Driving a tractor was probably a better job than pushing a plow. Certainly, the indicia of progress for a society, such as the standard of living, health, lifespan, leisure time, disposable incomes, have all seen dramatic increases through these revolutions.

So, the information revolution and the digital transformation of organizations that it engenders, do raise questions about the impact on jobs and livelihoods. But there is much cause for optimism looking at the issue through the lens of history.

It shouldn’t be ignored that some individuals will see disruption to their jobs as new technology is introduced. That is a societal problem. My view is society shouldn’t protect the old jobs. It should protect the people; that means, helping them transition to new opportunities, providing safety nets and such. Specific policies are out of my lane of course. But we can rely on history for the proposition that there should be more, not less, opportunity with the introduction of new technology.

Was there a “tipping point” that led you to this breakthrough? Can you tell us that story?

I’m a history buff, so one of the first things I do when confronted with a problem is see what analogs there are in history and how I can learn from that. There aren’t a lot of new problems, just old problems in new clothes.

When I was selling a technology product to law firms, firms often objected that the efficiency it offered would hurt them financially since they would work less hours, and therefore bill clients less.

My competitors created ROI analyses to show that the firms would make money anyway, using, frequently, self-serving assumptions. Few were convinced by these. They usually led to side-discussions about the integrity of the discussions.

I looked backward instead. I looked at the trend for adoption of technology in the market and built a graph reflecting the growth over a period of time. I then looked at the trend of law firm billable hours over the same time period. The trend lines were almost the same. This showed that while technology adoption was increasing, it didn’t decrease billable hours. They went up too.

This experience taught me to study history to inform my views about how future technologies — like software advances, AI, robotics or anything else, might impact something like job availability. It’s easy to paint fearful pictures; that has always been done and it sells papers. But looking backwards, at how new technologies have affected the job market, I find mainly grounds for optimism.

Of course, I’m talking here about economic opportunity and the jobs market. There has been a lot of discussion about the impact of technology on our social and emotional lives. That’s out of my pay grade. I’m addressing here what history has taught us about economic phenomena only.

What do you need to lead this technology to widespread adoption?

The corporate world is on a journey toward digital transformation already. We’re helping the legal departments navigate this journey, turning them into strategic leaders and influencers in their organizations. So, our mission is to help our clients optimize paths they are already on, rather than to convince them to adopt something.

This is a new role for me. In prior roles I was always evangelizing new ideas, trying to teach a market to do something they didn’t know they needed yet. This is much easier.

What have you been doing to publicize this idea? Have you been using any innovative marketing strategies?

No, I am somewhat embarrassed to say we’ve broken little new ground here. It won’t be this way forever and to scale the company we’ll need to explore these areas. For now, we hire brilliant, likeable people, put our clients’ needs ahead of ours and do a great job. Then the phone just rings.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I haven’t had a long-term mentor in my career. That has been a loss. I wish I had. However, late in my career I met Skip Keesal, the founder of the California law firm Keesal Young & Logan. The firm helped launch Keesal Propulsion Labs, is a major shareholder in it and Skip sits on our board. I’ve learned a lot about his career and watched how he leads people and how he participates in his community. Skip taught me how to be a better human being. That, really, is at the core of everything.

Also, I believe that greatness is in the agency of others. I’ve had two amazing co-founders; John Siegler in my first company and Justin Hectus in my current one. It’s not often that lightning strikes twice, but I’ve been lucky enough to twice team up with co-founders that are amazing talents, tireless colleagues and great friends. A big part of anything I achieved was so I would not let these guys down, since they never would do that to me.

I would encourage everyone to find a mentor — someone that inspires you to be the best human being you can. It’s never too late. Also, to work with people you care about. It makes the whole effort worthwhile.

How have you used your success to bring goodness to the world?

This is a work in progress. I have learned too much humility to claim any breakthroughs here. But I’ll share one effort which I’m hoping has had some impact on society.

After the financial crisis in 2008 it became clear that America was a country with a low savings and investment rate and a population with little experience managing money. It was also clear to me that a root cause was that kids don’t have any financial infrastructure to develop skills and habits. Those kids turn into adults without tools, experience or inclination to be successful financially.

So, I founded a fin tech company for the youth market called Kidworth. It was intended to create a generation of savers and investors and provide tech-friendly tools to an underserved segment of the financial market. It was founded and funded by mission-driven people, hoping that if we get a generation off to a good start, it would benefit them and society.

Ultimately, we were not successful. We built an award-winning product but could not capture the attention of the market. In the end, I lost a lot of money — and worse, some of my friends did too. Moreover, we didn’t have the impact we hoped. It remains the greatest disappointment of my professional life.

However, we did make an impact on the conversation about youth finance. We received a great deal of major press coverage where we were able to talk about the problem and how to address it. I personally met with hundreds of parents and kids and through that raised awareness. I hope that the legacy of this experience is there are some families out there working together to give kids a head-start in managing their financial lives and that those lessons spread over time.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Former British Prime Minister Benjamin Disreali said, “Most people die with their music still locked up inside them.” It struck me as one of the most tragic notions I’d ever heard. I looked at the people on the streets of New York City, where I was living and working at the time, at the expressions of the people on the subway platforms and saw the truth and sadness of that quote. I vowed early on never to let that happen. It has given me the courage to take some chances. That is all most of us need.

How can our readers follow you on social media?

https://Linkedin.com/in/RudyDeFelice
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