Hey there Legal Rebels! 👋
I’m excited to share with you the 56th episode 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!
If you want to understand how to build meaningful connections in the legal technology community and create lasting impact through consistent relationship-building, you need to listen to this episode. Ari is at the forefront of legal tech community building and has a unique perspective on creating value through generous service to others.
Building Community Through Three Decades of Consistent Connection
Join me as I interview Ari Kaplan, principal of Ari Kaplan Advisors and one of legal technology’s most prolific connectors.
In this insightful podcast episode, Ari shares his remarkable journey from practicing law at a large firm to building a thriving advisory business centered entirely on connecting people and creating opportunities. He reveals the personal traditions and practices that have sustained his work over 30 years, including his annual journal ritual that provides perspective on how far he’s come. Ari also demonstrates how seemingly small, consistent actions —from organizing virtual lunches to hosting breakfast meetups — can compound into extraordinary community impact over time.
His stories and insights underscore the power of generous service, from his Legal Tech Mafia breakfast series to his decade-long tradition of collecting canned food with his daughter. This episode is a must-watch for anyone curious about building meaningful professional relationships and creating community value, offering valuable perspectives on consistency, generosity, and the long game of relationship building.
The Skinny
Ari Kaplan, principal of Ari Kaplan Advisors, shares his three-decade journey as legal technology’s premier connector and community builder. With over 1,000 podcast episodes under his belt and countless connections facilitated, Ari reveals the personal practices that sustain his work, including a 30-year journal tradition that helps him reflect annually on his progress and set intentions for the future. Throughout the conversation, Ari emphasizes that his core identity is as a connector, someone who brings buyers to sellers, the informed to the less informed, and people seeking opportunities to those who have them. His approach combines professional activities like keynoting, training, and consulting with community-building initiatives like virtual lunch series, running groups, and the Legal Tech Mafia breakfast gatherings. Ari’s philosophy centers on ensuring people receive twice the value they put into any engagement, creating compounding returns through consistent, generous service over time.
Key Takeaways:
Ari has maintained a journal for 30 years, writing in it only once annually around New Year’s to reflect on the past year and project forward, a practice that provides remarkable perspective on personal and professional growth
His 1,000+ podcast episodes demonstrate the power of consistent content creation and conversation as a relationship-building tool
The transition from law firm partner to independent advisor required taking calculated risks, but Ari’s focus on creating value for others provided a sustainable foundation
Ari’s various community-building initiatives (virtual lunches, running groups, Legal Tech Mafia breakfasts) all share a common thread of connecting people and creating opportunities
His commitment to community service extends to personal life, including a decade-long tradition with his daughter collecting thousands of cans for food banks
Ari’s approach emphasizes giving people twice the value they put in, creating a virtuous cycle that sustains community engagement
The concept of “lucky work,” viewing professional activities as a privilege and gift rather than obligation, drives Ari’s sustained enthusiasm and impact
Small, consistent actions compound over time into extraordinary results, whether in professional networking or community service
Notable Quotes:
“30 years ago around New Year’s, I decided I was going to keep a journal that I write in once a year because I felt like it’s so powerful to be able to reflect and to look forward.” - Ari Kaplan (03:20-03:32)
“At the time I was in law school, I was like, oh, I hope I get a job. And then I got a job and I was like, wow, I got a job. Can I pay back my loans? Can I ever make a living? Oh, I’m dating this girl and I really like her. And we’ve been married now 25 years.” - Ari Kaplan (03:48-04:02)
“The beauty of this journal is that I only write in it once a year. Once a year, right around New Year’s. I try to commit to New Year’s Eve, New Year’s Day. I almost never do that.” - Ari Kaplan (05:22-05:31)
“When you read about what you wrote 20 years ago, where you would hope to be, you’re almost always exceeding that. I hope I can afford to live in a place. I hope I can afford to send my kids to college, that kind of thing. Once you’ve done that and you read about it, you’re like, this is pretty good.” - Ari Kaplan (06:07-06:24)
“In my core, I feel like I’m a connector. I’m a community builder. And a lot of the different activities, the thread that runs through it is me trying to connect either buyers to sellers or the informed to the less informed or people who are trying to find an opportunity to people who have an opportunity.” - Ari Kaplan (45:50-46:12)
“Anything that I’m doing is usually about bringing others together, learning from each other, making sure that people get twice the value that they’re putting in.” - Ari Kaplan (46:23-46:28)
“Every once in a while, I’ll see someone will say, oh, we finally met in person. We met through your virtual this or your that. And I think that that is the best way to do this.” - Ari Kaplan (46:55-47:01)
“I’d like to think that in my world, what I’m trying to do is connect all of these constituencies to just try to amplify all this exceptional work but also many of the stories and personalities that really make it so wonderful.” - Ari Kaplan (47:28-47:45)
“I think of my work as a gift. I always say on LinkedIn, I get to do lucky work.” - Ari Kaplan (47:48-47:52)
Clips
I Started College at 16
Why I Journal Once A Year
Writing In The Middle of the Night
My 30-Year New Year’s Ritual
Ari’s journey illustrates a profound truth about professional success: the most sustainable careers are often built not on what you take, but on what you give. His transition from traditional legal practice to becoming a full-time connector and community builder required courage, but it was sustained by a simple principle, create more value for others than you capture for yourself. This philosophy manifests in everything from his podcast interviews to his breakfast gatherings to walking through his neighborhood collecting canned food with his daughter.
What makes Ari’s approach particularly powerful is the consistency. The journal entries, the podcast episodes, the community events, the food drives, these aren’t one-off activities but sustained commitments that compound over time. The same discipline that keeps him writing in his journal for 30 years powers his ability to produce over 1,000 podcast episodes and facilitate countless professional connections.
Closing Thoughts
As someone who’s built LawDroid through community engagement and relationship building, I find Ari’s approach both inspiring and instructive. He represents a model of professional success that feels increasingly rare: one built on genuine service, consistent effort, and long-term thinking rather than short-term optimization.
What strikes me most about Ari’s story is how his professional life and personal values are completely integrated. The same principles that guide his decade of collecting food donations with his daughter inform how he approaches his Legal Tech Mafia breakfasts and virtual lunch series. He’s not trying to maximize extraction from his network; he’s trying to maximize the value his network creates for each other.
For our Legal Rebels community, Ari’s journey offers a powerful alternative to the hustle-and-grind narrative that dominates so much professional advice. You don’t need to be everywhere or do everything. You need to find your thing, your way of connecting people and creating value, and then do it consistently for a very long time. The compound interest of generosity and consistency is extraordinary.
As legal technology continues to evolve at breakneck speed, the human element becomes even more critical. Those who can build genuine communities, facilitate real connections, and create spaces where people receive more value than they give will always be essential. Ari has been doing this for 30 years, and his continued enthusiasm (his description of his work as “lucky work”) shows that this approach isn’t just effective, it’s sustainable and deeply fulfilling.
The future of legal innovation belongs not just to those with the best technology or the smartest strategies, but to those who can build the communities and connections that allow innovation to spread and take root. That’s what Ari has been doing for three decades, and that’s why his perspective matters now more than ever.
