Renegade Litigator Retreat

Filevine is thrilled to invite you and a guest to our exclusive Renegade Litigator Retreat at the Four Seasons Peninsula Papagayo in Costa Rica. This gathering brings together an elite circle of litigators; leaders who challenge convention, think boldly, and push the profession forward. This retreat is designed as a space for renegades to connect, exchange ideas, and spark innovation. Join us in Costa Rica for an unforgettable experience among peers who are redefining what’s possible in litigation.

At Filevine, we believe in the power of the “Renegade"; those who are unafraid to challenge the status quo, embrace extraordinary ideas, and drive transformative change within their legal organizations. Will you be next to join the ranks?

Limited Spots Available

March 1st–4th, 2026
Four Seasons Peninsula Papagayo | Costa Rica

Over three immersive days, we’ll gather in this extraordinary setting to trade real-world courtroom wins, explore breakthroughs in legal technology, and uncover strategies that amplify your influence and your firms performance. Designed for the trial attorneys who drive the business and set the pace, this retreat is your chance to connect with fellow power players, collaborate on bold ideas, and embrace the mindset of a true Renegade Litigator.

Renegade 2025 Lookback

Agenda

Sunday
1st
Welcome to Costa Rica, Pura Vida
Armadillo Pavillion Event Lawn

Join us for welcome drinks, dinner & a fun activation 

5 p.m.–8 p.m.
Monday
2nd
Breakfast | Guests Invited
Armadillo Event Pavilion
7 a.m.–8 a.m.
Welcome & How AI Will Help You Win
Ryan Anderson, CEO | Filevine

Kick off the retreat with an insider’s look at where the industry is headed. Ryan will welcome the group, set the tone, and share why you were hand-selected to be part of this renegade cohort. He’ll pull back the curtain on Filevine’s vision for the future of legal technology and how emerging tools and AI, are reshaping the way elite litigators win cases, scale their impact, and lead inside their firms. 

8 a.m.–8:20 a.m.
The Renegade Exchange
Keegan Chapman, Chief Marketing Officer

A high-energy, full-room facilitation designed to get you connected quickly. We’re cutting the small talk to focus on the big moves: the cases you’re excited about and the challenges that are actually moving the needle in your practice. You’ll leave this hour with a clear view of the elite talent in the room and a shortlist of peers to seek out for deeper strategic dives.

Fast. Candid. Unfiltered. You’ll walk out with smarter ideas and solutions you can use the second you get home.

8:20 a.m.–9:20 a.m.
Advocacy in the Hardest Rooms: Trial Strategy in Trauma & Civil Right Litigation
Kristen Gibbons Feden, Anapol Weiss | Christopher Mattei, Koskoff, Koskoff & Bieder | Lee Merritt, Merritt Law, Moderated by Jeanne Gills, Foley & Lardner

A raw, unfiltered conversation with Kristen Gibbons-Feden & Christopher Mattei on the trial strategies that drive complex, emotionally charged, and nationally visible cases. The panel will explore narrative development, witness preparation, managing traumatic evidence, and handling media and public scrutiny while keeping juries anchored in the law and the facts.

9:20 a.m.–10:20 a.m.
Break
10:20 a.m.–10:40 a.m.
The Verdict Algorithm: What Jurors Decide Before Deliberations Even Begin.
Jakob Norman,National Managing Partner | Trial Layers For Justice

Elite trial lawyers know that verdicts are rarely the product of pure logic, especially in high-stress, high-stakes environments. Drawing on decades of military decision-making experience and research conducted alongside Harvard psychology professors, this session examines how stress, uncertainty, authority, and group dynamics inside the jury room mirror battlefield and leadership decision-making. Attendees will explore why jurors form conclusions about credibility and “truth” long before opening statements end, why legally flawless arguments often fail, and what trial lawyers consistently misunderstand about so-called “smart jurors.” Grounded in science and real-world application, this talk shows how elite litigators can ethically align trial strategy with how humans actually make decisions, not how the law assumes they do. 

10:40 a.m.–11:40 a.m.
Who Cites the Citator? LLMs, Open Data, and the Future of Legal Research
John Rizner, Product Manager, Filevine

The legal research market is approaching an inflection point that most practitioners haven't fully registered. On one side, an unprecedented volume of American caselaw has become freely accessible and processable by digital tools. On the other, data science techniques and large language models have reached a level of legal sophistication that would have been unimaginable five years ago. Taken together, these developments create the possibility of new legal research tools and call into question assumptions the profession has held for a generation about who can build a citator, what it should cost, and how much trust we should place in any single provider's signals. In this session, we investigate what becomes possible when open caselaw meets modern computing: from citation network mapping to semantic similarity comparison. We share early findings from our own research, examine the real limitations alongside the advancements, and ask the question litigators should be asking: is meaningful competition in legal research no longer a matter of if, but when?

11:40 a.m.–noon
Lunch | Guests Invited
Armadillo Event Pavilion
noon–1 p.m.
Free Time

Enjoy your afternoon,

* Spa appt, Catamaran, or Complimentary activities onsite. 

 

1 p.m.–5 p.m.
Dinner | Guests Invited
Playa Virador Beach Club

Live Music & Dinner on the beach. 

5 p.m.–8 p.m.
Tuesday
3rd
Breakfast | Guests Invited
Armadillo Event Pavilion
7 a.m.–8 a.m.
Extending Your Reach:  The Litigator’s Command Console
Michael Anderson, Chief Product Officer, Filevine

You’re already doing the work of three people, yet the intake pile keeps growing. We’ve all been there on both sides of the V. Michael opens with the frustrating reality of the "unreachable lawyer" and why the current legal model is fundamentally broken for both the attorney and the client. This session introduces Extensibility: a framework to push your expertise further using AI. Michael will break down the four pillars of a high-leverage practice, from automated information gathering to intuitive interfaces showing you how to stay in "the zone" while the system handles the heavy lifting.

8 a.m.–8:50 a.m.
Litigating in the Spotlight: Strategy When the Courtroom Isn’t the Only Battlefield
Mathew Rosengart, Greenberg Traurig & Joseph Tacopina, Tacopina Seigel & DeOreo | Moderated by Ryan Anderson, Filevine

When litigation unfolds under intense public scrutiny, the courtroom is only one of many battlegrounds. In this candid conversation, Mathew Rosengart and Joseph Tacopina explore how elite trial lawyers manage media pressure, counsel high-profile clients, and make strategic decisions when every move carries consequences beyond the case itself. This session examines the judgment, discipline, and control required to litigate effectively when visibility is unavoidable.

8:50 a.m.–9:50 a.m.
Break
9:50 a.m.–10 a.m.
Winning the Margin: Where AI Actually Changes Case Outcomes
Brent Wisner, Wisner Baum | Howard Kanner, Kanner Pintaluga | Kimball Jones, BigHorn Law, | Moderated by Alex Pearson
10 a.m.–11 a.m.
Inside the AI War Room
Filevine Team

In this live session, The Filevine team pulls back the curtain on the future of trial work: real-time tools, and the technology that gives high-profile litigators the edge they need in high-stakes cases. A front-row seat to the evolution of one of your most powerful litigation tools.

11 a.m.–12:20 p.m.
Lunch | Guests Invited
Armadillo Event Pavilion
12:20 p.m.–1:20 p.m.
Free Time

Enjoy your afternoon,

* Spa appt, Catamaran, or other complimentary activities onsite. 

 

1:20 p.m.–5:45 p.m.
Dinner at Nemare | Guests Invited
Meet at the lobby at 5:45 to take shuttle to restaurant
6 p.m.–9 p.m.

Attendees

Ryan Anderson
Ryan Anderson
Founder and CEO, Filevine
Michael Anderson
Michael Anderson
Chief Product Officer, Filevine
Alex Pearson
Alex Pearson
General Counsel, Filevine
Sean Dowdle
Sean Dowdle
Chief Revenue Officer, Filevine
Ben Aird
Ben Aird
SVP, Sales, Filevine
Keegan Chapman
Keegan Chapman
Chief Marketing Officer, Filevine
Alex McLaughlin
Alex McLaughlin
VP, FDE & Strategic Initiatives, Filevine
Mary Lyon
Mary Lyon
VP, SE & Enablement, Filevine
Sona Sulakian
Sona Sulakian
VP, AI Drafting Products, Filevine
Juliana Groscost
Juliana Groscost
VP of Product & Experiential Marketing, Filevine
Ryan Evans
Ryan Evans
VP, Sales, Filevine
Dr Cain Elliott
Dr Cain Elliott
Chief Legal Futurist, Filevine
Jason Luke
Jason Luke
Director, Strategic Sales, Filevine
Keisha Crawford
Keisha Crawford
Field Events Marketing Manager, Filevine
Katie Peacock
Katie Peacock
Events Outreach Representative, Filevine
Yvette Ostolaza
Yvette Ostolaza
Chair, Management Committee, Sidley Austin, LLP
Yolanda Garcia
Yolanda Garcia
Partner, Sidley Austin, LLP
Priya Chaudhry
Priya Chaudhry
Founding Partner, ChaudhryLaw PLLC
Stephen Kohn
Stephen Kohn
Partner, Kohn, Kohn and Colapinto
Timothy Ray
Timothy Ray
Partner, Holland & Knight
Kristen Gibbons-Feden
Kristen Gibbons-Feden
Shareholder, Anapol Weiss
Joseph Tacopina
Joseph Tacopina
Attorney, Tacopina Seigel & DeOreo
Kenya Davis
Kenya Davis
Partner, Boies Schiller Flexner, LLP
Daniel Saeedi
Daniel Saeedi
Partner, Blank Rome LLP
Christopher Mattei
Christopher Mattei
Partner, Koskoff, Koskoff & Bieder
Christina	Sarchio
Christina Sarchio
Partner, Dechert
Joseph K West
Joseph K West
Partner, Duane Morris LLP
Renato Mariotti
Renato Mariotti
Partner, Paul Hastings
Mathew Rosengart
Mathew Rosengart
Partner, Greenberg Traurig
Maurice Bellan
Maurice Bellan
Managing Partner, Baker & McKenzie LLP
Vincent Cohen
Vincent Cohen
Global Managing Partner, Dechert
Jeanne Gills
Jeanne Gills
Partner, Foley & Lardner
Ronald C Machen JR
Ronald C Machen JR
Partner, Wilmer Hale
Jeannie Rhee
Jeannie Rhee
Partner, Dunn Isaacson Rhee LLP
Joe Drayton
Joe Drayton
Partner, Proskauer Rose
Shannon Liss- Riordan
Shannon Liss- Riordan
Partner/Co-Founder, Lichten & Liss-Riordan, P.C.
Michael Andolina
Michael Andolina
Partner, White & Case
Camille Olson
Camille Olson
Partner, Seyfarth Shaw
Megan Rodgers
Megan Rodgers
Partner, Covington & Burling LLP
Gwendolyn Fleming
Gwendolyn Fleming
Partner, DLA Piper, LLP (US)
Marilyn Chinitz
Marilyn Chinitz
Partner, Blank Rome LLP
S. Lee Merritt
S. Lee Merritt
Constitutional Human Rights Lawyer, Merritt Law
Danny Tobey
Danny Tobey
Global Co-Chair, AI Practice, DLA Piper, LLP (US)
Jakob Norman
Jakob Norman
National Managing Partner, Trial lawyers For Justice
Brent Wisner
Brent Wisner
Managing Partner, Wisner Baum
Kimball Jones
Kimball Jones
Partner, Big Horn Law
Howard Kanner
Howard Kanner
Co Founder / Partner, Kanner and Pintaluga
Marcus Maples
Marcus Maples
Shareholder, Baker Donelson
David Cross
David Cross
Partner, Goodwin

Frequently Asked Questions

When & where does the event take place?

The event begins at 6:00pm on March 1st and ends on the afternoon of March 4th.

Do I need to book my accommodations?

As our valued guest, we have taken care of your stay at Four Seasons Peninsula Papagayo from March 1st- March 4th. If you have any questions or requests, please email Keisha Crawford at [email protected].

Do I need to book transportation?

Filevine will cover transportation during the event and round trip transportation from the LIR airport to the Four Seasons Peninsula Papagayo .

Am I permitted to invite my spouse/partner/friend and what are they allowed to join?

Yes, you are welcome to have your spouse/partner stay with you and join us for specific activities. It will be notated on the Agenda. Although, the majority of the event programming will be for Litigators only to ensure that the content and connections are focused. Each room can accommodate 2 adults & 1 child, hotel needs to be aware of all guests. Note: Children will not be permitted at any of the summit activities.

Who is invited to attend the summit?

This is a private invite-only event for High Profile Litigators at active large firms. The invite cannot be transferred without permission from our team. If there is someone you believe should be invited we are happy to discuss.

Am I allowed to extend my stay at the Four Seasons Peninsula Papagayo? ?

Yes. We have received special pricing for our guests to extend their stay for up to three pre & post the event. The discounted rate is $995++ per night and will be dependent on availability at the time of the request. You will be responsible for paying for any additional personal nights. To learn more, please email Keisha Crawford at [email protected]

What is the dress code?


Sessions – Resort Business Casual
Lightweight tops (button-downs, polos, blouses), linen or breathable pants, comfortable elevated footwear. Polished but relaxed for warm weather.

Dinners – Resort Elegant
Flowy dresses or sets, linen shirts, tailored pants, dressy sandals or loafers. Elevated tropical evening wear.

Who do I contact if I have questions or requests?

Please email Keisha Crawford at [email protected]

This seems to good to be true, is this real?

Yes, this is real! Take a look here at the group of CIO's & attorneys we hosted last year in Hawaii.

Can more than one person from the same firm attend?

We are only allowing two (2) people represent the same firm, even if more than two were invited. Please keep this in mind as you discuss attendance.

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