Hey there Legal Rebels! 👋 I'm excited to share with you the 37th episode of the 2025 season of the LawDroid Manifesto podcast, where I will be continuing to interview key legal innovators to learn how they do what they do. I think you're going to enjoy this one!
I’ve known Dan for years, first in his role at Avvo and now as Vice President of Lawyer Services Relations at LegalShield. [Dan exited his role at InfoTrack at the end of August.] One thing about Dan is that he naturally captures his audience’s attention. So, when I learned that one of Dan’s professional ambitions was to be "the interesting client," rather than the lawyer who be serves them, I dubbed Dan “The Main Character” because he is. I hope you enjoy our conversation.
If you want to understand how to transition from traditional legal practice to legal technology leadership while maintaining your authentic self and values, you need to listen to this episode. Dan is at the forefront of legal technology partnerships and has a unique perspective on charting an unconventional career path in legal innovation.
Transforming Legal Careers Through Authentic Innovation
Join me as I interview Dan Lear, now as VP Lawyer Services Relations at LegalShield, former VP of Partnerships at InfoTrack, and advisor to Off the Record.
In this podcast episode, Dan shares his journey from growing up in a family full of lawyers in Salt Lake City to becoming a respected voice in legal technology. We explore his experience at Microsoft, his time building the legal innovation community in Seattle, and his pivotal role at Avvo in transforming how lawyers connect with clients. Dan also reveals the personal philosophy that guided his transition from traditional practice to legal technology leadership, including his realization that he wanted to be "the interesting client" rather than just serve them.
His stories and insights underscore the importance of following your authentic path, even when it means abandoning the security of traditional legal practice. This episode is a must-watch for anyone considering a career transition within the legal industry, offering valuable perspectives on building community, taking calculated risks, and making meaningful impact through technology.
The Skinny
Dan Lear shares his unconventional journey from a Salt Lake City family of lawyers through international studies, a mission in Russia, and a JD/MBA program to becoming a legal technology pioneer. Despite coming from a family where law was the expected path, Dan's experiences at Microsoft while in law school opened his eyes to how technology could transform legal practice. After several years in traditional practice, he made the bold decision to leave the security of practicing law to carve his own path in legal technology. Through networking, writing, and community building in Seattle, Dan eventually landed at Avvo, where he played a crucial role in connecting lawyers with clients and advancing legal innovation. His philosophy centers on being "the interesting client" rather than serving them, and he emphasizes that a law degree serves as both a map with clear career paths and a floor providing economic security, both of which he willingly abandoned to pursue meaningful impact in legal technology.
Key Takeaways:
Dan's family background of lawyers provided both inspiration and pressure to pursue law, but his parents' non-traditional approaches to legal careers influenced his entrepreneurial mindset
A two-year mission in Russia during college expanded his worldview and reinforced his interest in international studies and diverse perspectives
Working at Microsoft while in law school exposed him to cutting-edge technology and highlighted the stark contrast with traditional legal practice methods
The JD/MBA combination provided broad perspective but limited practical career options, leading Dan to initially follow a traditional legal path despite his interests
Community building through meetups, blogging, and bar association involvement became the foundation for Dan's transition into legal technology
His networking with Patrick Pallas at the Washington State Bar Association directly led to his opportunity at Avvo through connections and shared interests
The concept of a law degree as both a "map" (clear career progression) and a "floor" (economic security) helps explain why leaving traditional practice can be both scary and liberating
Dan's realization that he wanted to be "the interesting client" rather than serve them, inspired by Charlie Munger, crystallized his decision to leave practice
Work-life balance for Dan centers on non-negotiable family time, influenced by his father's example of being present despite a busy career
Making meaningful impact and being able to explain his choices to his children provides the deeper motivation for his unconventional career path
Notable Quotes:
"I come at the technology from a practical perspective first. When I discovered AI, when ChatGPT first came out, December of 2022, I was in-house counsel at that time. And I was really focused on how can I implement this technology into my practice and then more broadly into the practice of my legal department." - Dan Lear (03:04-03:23)
"I would return to my desk, and it was like I was walking back in time. I was seeing all of these amazing technologies. I was seeing just this amazing, amazing stuff that everybody was building. And then I would go back, and I was like, well, yeah, I guess I've upgraded from a feather quill to a word processor. But the way I think about doing this work is just like... It hasn't really changed." - Dan Lear (23:43-24:02)
"In the land of the blind, the one-eyed man is king." - Dan Lear (25:31-25:35)
"I realized that I didn't want to work with all of these interesting clients. I wanted to be them." - Dan Lear (35:00-35:02)
"When you plug in as a typical lawyer, whether you're in-house or at a law firm or even a solo, like, the path is pretty well established. You know, you go from associate to partner, you go from whatever staff counsel to associate general counsel... So it's a map, right? It gives you a pretty clear direction to go." - Dan Lear (32:19-32:56)
"When I left the practice of law to kind of, you know, carve my own path in legal technology, I threw the map out and I lost the floor." - Dan Lear (33:43-33:48)
"I absolutely feel like... it was important to me to at least try to have an impact... I can turn around to my... boys and say, Hey, listen, this is the choice I made. And here are the reasons that I made those choices." - Dan Lear (42:07-43:25)
Clips
Why The “Techie Lawyer” Is Treated Like A Prophet
The Legal World Is Stuck in the Past
Why a Law Student Quit to do Standup
Why Lawyers Have a Built-In Safety Net
Dan's journey represents a masterclass in authentic career navigation within the legal industry. His willingness to abandon the security of traditional legal practice in favor of uncharted territory in legal technology demonstrates the courage required for meaningful innovation. What makes Dan's story particularly compelling is how he leveraged his diverse background – from international experience in Russia to his technology exposure at Microsoft – to build a unique perspective that served him well in legal technology.
The concept of viewing a law degree as both a map and a floor provides valuable framework for any lawyer considering alternative career paths. Dan's insight about wanting to be "the interesting client" rather than serve them reflects a fundamental shift in mindset that many entrepreneurial lawyers can relate to. His emphasis on community building, authentic networking, and gradual skill development offers a practical roadmap for others looking to make similar transitions.
Closing Thoughts
Dan Lear's story resonates deeply with me as someone who has also navigated the transition from traditional legal practice to legal technology entrepreneurship. What strikes me most about Dan's journey is his authenticity; he didn't follow a predetermined playbook but instead created his own path based on his values, interests, and desire for meaningful impact.
His insight about the law degree as both map and floor is particularly valuable for our Legal Rebels community. It acknowledges the very real security that traditional legal practice provides while also recognizing the limitations it can impose. Dan's willingness to abandon both the map and the floor demonstrates the kind of courage required for true innovation in our industry.
The timing of Dan's transition also offers lessons for today's legal professionals. He recognized early that technology would transform legal practice and positioned himself at that intersection before it became mainstream. His experience at Avvo, helping to democratize access to legal services through technology, shows how legal innovators can create meaningful impact while building sustainable careers.
For those considering their own transitions, Dan's emphasis on community building and authentic networking provides a practical framework. His approach of starting small, with a blog, a meetup group, conversations with bar associations, shows how incremental steps can lead to transformative opportunities.
Perhaps most importantly, Dan's story demonstrates that success in legal innovation isn't just about technology or business acumen, it's about staying true to your values and maintaining perspective on what really matters. His commitment to family time and his desire to make choices he can explain to his children provides a North Star that transcends career achievements.
As legal technology continues to evolve rapidly, we need more leaders like Dan who combine technical understanding with deep appreciation for the human elements of legal practice and career development.
