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The Bookleggers

Jacob Fleckenstein

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Step into the podcast that is basically a book club, Welcome to The Bookleggers! In Season 1, we're venturing deep into the realm of Fantasy books, starting with C.S. Pacat's gripping "Dark Rise," Nicholas Eames' epic masterpiece, "Kings of the Wyld," the thrilling saga of John Gwynne's "Shadow of the Gods." and many more fantasy titles to come. Grab your favorite beer, and listen in as Jake and Joel debate our favorite characters, unravel some intricate plot points, make outlandish predicti ...
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In The Lab with Ruben Kanya compiles over $2 Billion worth of successful real estate experiments for new investors looking to get started in real estate. With real estate being a broad umbrella, in the lab we introduce you to a variety of real estate models (experiments) that real practitioners have implemented while sharing their wins, losses and lessons in the lab so that you can pick the experiments that suit your lifestyle the most and double down. In the lab we focus on repeatable proce ...
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Get the Midterm Rental Insurance Blueprint: https://experimentrealestate.com/#blueprint In this powerful episode of In The Lab, Ruben sits down with George Otel, a finance expert, entrepreneur, and investor who has carved a unique path from trucking fleets to becoming “the finance guy” for business and real estate deals. George immigrated to the U.…
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This week, we talk with Gabe Pereyra, President and co-founder at Harvey, about his path from DeepMind and Google Brain to launching Harvey with Winston Weinberg; how a roommate’s real-world legal workflows met early GPT-4 access and OpenAI backing; why legal emerged as the right domain for large models; and how personal ties to the profession plus…
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Connect with me at https://experimentrealestate.com/connectGet the FREE Mid-Term Rental Insurance Blueprint: https://experimentrealestate.com/#blueprint In this episode, Ruben shares a simple but powerful framework from his mentor, Myron Golden —the three C’s of fulfillment—and shows how it applies to business, real estate, and life. If something f…
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This week we sit down with Suzanne Konstance, Vice-President and General Manager for Legal and Regulatory US at Wolters Kluwer. She outlines how the company supports professionals in highly regulated fields with software and authoritative content. Operations span multiple countries with a deliberately local approach, where teams design solutions fo…
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Connect with me at https://experimentrealestate.com/connect Get the FREE Mid-Term Rental Insurance Blueprint: https://experimentrealestate.com/#blueprint In this solo briefing, Ruben breaks down Airbnb’s move to a single host-only fee (15.5%) for listings managed through property management software (PMS)—what’s changing, when it hits, and what it …
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This week we are joined by Patrick DiDomenico and Kevin Klein, two longtime builders of knowledge programs and legal tech gatherings. They walk through the evolution of KM&I for Legal, now entering year three, and the debut of its co-located counterpart, Legal Tech Connect. Both events run in New York on October 22 and 23, with a single community, …
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This week we are joined by Mirat Dave and Danish Butt of Swiftwater & Co. as they step into the studio to make a simple claim, investigations and legal operations should serve the business, not slow the business. Mirat traces a path across law, technology, and global risk, then explains why a team blending strategy with implementation drew him to S…
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In this focused solo episode of In The Lab, Ruben unpacks the lessons he learned from attending a three-day Nike tennis training camp and how they directly apply to business, real estate, and personal growth. He reflects on the four key pillars that make intensive training so powerful—proximity, reps, correction, and longevity—and why missing just …
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Connect with me at https://experimentrealestate.com/connect Get the FREE Mid-Term Rental Insurance Blueprint: https://experimentrealestate.com/#blueprint In this reflective solo episode of In The Lab, Ruben shares the lessons he gained from running his first 10K race and how they directly apply to entrepreneurship, real estate, and life. From train…
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This week, we welcome back Kara Peterson and Rich DiBona of Descrybe to talk about the company’s rapid growth and its expanding role in legal research. Since their last appearance, Descrybe has not only built out new tools but also entered academia by joining the curriculum of more than 350 universities around the world. Kara reflects on her earlie…
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Connect with me at https://experimentrealestate.com/connect Get the FREE Mid-Term Rental Insurance Blueprint: https://experimentrealestate.com/#blueprint In this high-impact episode of In The Lab, Ruben sits down with Brandon Rickman, an Atlanta-based investor, entrepreneur, and general contractor who has flipped over 500 houses, developed 100 new-…
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In this episode of The Geek in Review, we welcome back Pablo Arredondo, VP of CoCounsel at Thomson Reuters, along with Joel Hron, the company’s CTO. The conversation centers on the recent release of ChatGPT-5 and the rise of “reasoning models” that go beyond traditional language models’ limitations. Pablo reflects on his years of tracking neural ne…
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This week, we welcome back Tom Martin, CEO of LawDroid, to discuss his widely read “AI Law Professor” column for Thomson Reuters and his five-level roadmap for legal AI. Martin explains that the framework was inspired by a leaked OpenAI memo and aims to give legal professionals a clearer picture of AI’s trajectory. The five levels range from basic …
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Connect with me at https://experimentrealestate.com/connect Get the FREE Mid-Term Rental Insurance Blueprint: https://experimentrealestate.com/#blueprint In this powerful and paradigm-shifting episode of In The Lab, Ruben sits down with Jay Cameron, real estate investor, international speaker, and founder of Maximum Impact Travel. Jay opens up abou…
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This week, we welcome longtime friend and legal tech veteran Ken Crutchfield, founder of Spring Forward Consulting. Ken brings his extensive experience from major legal information vendors like Thomson Reuters, Bloomberg, and Wolters Kluwer into a timely and candid discussion about the current phase of artificial intelligence in the legal industry.…
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Get the Midterm Rental Insurance Blueprint: https://experimentrealestate.com/#blueprintIn this deep-dive episode of In The Lab, Ruben sits down with Joel Friedland, founder of Brit Properties, to explore an uncommon but powerful approach to real estate syndication: acquiring industrial properties with no debt. Joel, who has been in the industrial r…
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This week, we welcome Christian Geyer, founder and CEO of ACTFORE, for a deep dive into the world of automated breach response. From his early days in military intelligence to founding a disruptive forensics firm, Christian shares how his diverse experiences shaped a data‑driven approach to tackling one of corporate America’s thorniest problems: ma…
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In this timely episode of In The Lab, Ruben breaks down when and why you should consider shifting to a hybrid short-term and mid-term rental model and how the latest tax legislation makes it even more lucrative. Coming off last week’s Driving Conversations with AI vs. Questions, he explains how operators can strategically layer MTR contracts over S…
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This week, we sit down with Ilona Logvinova, Director of Practice Innovation at Cleary Gottlieb, and Max Junestrand, CEO and Founder of Legora, for a deep dive into how their partnership is reshaping the legal landscape through AI-driven innovation. The conversation kicks off with the origin story behind Cleary’s strategic alliance with Legora, a l…
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Get the FREE Mid-Term Rental Insurance Blueprint: https://experimentrealestate.com/#blueprint In this informative episode of In The Lab, Ruben breaks down a powerful framework for how to actually use AI as a strategic partner—not just a search engine. Drawing from real-world conversations he's had with AI to help close deals, refine business plans,…
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In this episode, we welcome Matthew Dickinson, CEO and founder of Vable, to discuss the rapidly changing landscape of legal information and current awareness. Matthew reflects on how, until recently, current awareness in law firms relied heavily on manual curation, Boolean searches, and email alerts—often resulting in information overload and a lac…
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Get the Midterm Rental Insurance Blueprint: https://experimentrealestate.com/#blueprintIn this solo episode of In The Lab, Ruben delivers a powerful, high-impact debrief heading into Q3 2025. With the lab coat on and lessons in hand, he walks through seven strategic experiments and three hard-earned insights from the previous quarter that every rea…
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In this week's episode of The Geek in Review, Greg Lambert flies solo while co-host Marlene Gebauer enjoys some well-deserved relaxation. Greg welcomes Trevor Quick, Strategic Business Development lead at Harvey.ai, to discuss one of the most talked-about companies in legal tech today. With a staggering $300 million Series E funding round and a $5 …
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Get the Midterm Rental Insurance Blueprint: https://experimentrealestate.com/#blueprint In this data-packed episode of In The Lab, we sit down with Jeff Hurst, CEO of Furnished Finder and former President of Vrbo, Chief Strategy Officer at HomeAway, and COO of Expedia Group. Jeff brings decades of experience in travel and hospitality tech to a fast…
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In this episode of The Geek in Review, guest host Marcie Borgal Shunk of the Tilt Institute joins Marlene Gebauer for a thought-provoking discussion with Avaneesh Marwaha, CEO of Litera. As someone who led the company through both pre- and post-AI boom eras, Avaneesh offers an insider’s perspective on what it takes to guide a legal tech organizatio…
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Connect with me at https://experimentrealestate.com/connect Get the FREE Mid-Term Rental Insurance Blueprint: https://experimentrealestate.com/#blueprint In this insightful episode of In The Lab, we’re joined by Gabriel Wacker, Vice President of Sales and Marketing at Transitions Group—a vertically integrated firm providing solutions in corporate h…
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In this episode of The Geek in Review, hosts Marlene Gebauer and Greg Lambert sit down with Otto von Zastrow, the founder and CEO of MidPage.AI, an AI-native legal research platform. With a recent $4 million seed round and an ambitious mission to rival legacy research tools, MidPage is drawing attention across the legal industry. Otto shares his un…
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Get the Midterm Rental Insurance Blueprint: https://experimentrealestate.com/#blueprint In this energizing and introspective episode of In The Lab, Ruben sits down with Corey Ryan Bevilacqua and Cory Jacobson, co-founders of the Wealth Juice brand and podcast. These two long-time friends and partners share their inspiring journey from college roomm…
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In this special episode of The Geek in Review, we take the new ChatGPT Advanced Voice Mode for a spin, inviting it to analyze and discuss all 23 episodes from the podcast’s 2025 season. The episode kicks off with a high-level overview of the biggest legal tech themes from the year so far. ChatGPT Voice quickly identifies a significant shift toward …
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Get the Midterm Rental Insurance Blueprint: https://experimentrealestate.com/#blueprintIn this immersive episode of In The Lab, Ruben sits down with Melissa Darnay, founder of Choose Panama and host of The Panama Podcast. Melissa shares her remarkable story of turning personal tragedy into purpose by relocating to Panama and building a thriving rea…
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This week, we welcome Cornell Winston (current President of the American Association of Law Libraries) and Jenny Silbiger (President‑Elect). Speaking from sunny San Diego and O‘ahu’s courthouse halls, the duo joins the show to preview AALL’s 2025 Annual Meeting in Portland, Oregon—and to talk candidly about the challenges and opportunities facing t…
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Get the Midterm Rental Insurance Blueprint: https://experimentrealestate.com/#blueprint In this inspiring episode of In The Lab, we're joined by Brian Hatcher, founder and CEO of Hatch Capital, and Aaron Appleton, his trusted partner in Hatch Capital property management and founder of Mirror Haus Collection micro resort. Together they’ve moved from…
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In this episode of The Geek in Review, we welcome Feargus MacDaeid and Nnamdi Emelifeonwu, co-founders of Definely, to discuss how their shared experiences as practicing lawyers shaped a groundbreaking accessibility solution for contract review. Feargus, who is visually impaired, and Nnamdi, his former colleague at Freshfields, describe how their f…
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On this episode of The Geek in Review, we welcome Philip Young, co-founder and CEO of Garfield AI, the first AI-powered law firm approved for practice by the UK’s Solicitors Regulation Authority (SRA). The episode kicks off with a discussion of recent stories that explore AI’s evolving role in legal proceedings, such as avatars testifying in court …
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In this eye-opening episode of In The Lab, Ruben sits down with public adjuster Andy Gurczak of All City Adjusting for a second time to unpack the misunderstood world of insurance claims and temporary housing. Andy explains why most homeowners and investors are at a major disadvantage when filing insurance claims and how public adjusters can help r…
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This week we sit down with Matt Rasmussen, Founder and CEO of ModeOne, to dive into the evolving challenges and solutions around mobile device discovery. What started as a frustration-fueled “passion project” has grown into a powerful, cloud-based legal tech tool that dramatically speeds up mobile data collections while safeguarding user privacy. R…
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Want to work with me and learn the power of Mid-Term Rentals Insurance? https://experimentrealestate.com/submitGet the FREE Mid-Term Rental Insurance Blueprint: https://experimentrealestate.com/#blueprint In this high-energy behind-the-scenes episode of In The Lab, Ruben and Vivian sit down to unpack the real wins, surprises, and life-changing conv…
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For the 300th episode of The Geek in Review, we celebrate in true “three geeks” fashion by bringing back two familiar voices: Kris Satkunas, Director of Strategic Consulting at LexisNexis, and legal pricing expert Toby Brown, CEO at DV8 Legal Strategies. Kris joins to walk through highlights from the newly released 2025 CounselLink Trends Report, a…
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Want to work with me and learn the power of Mid-Term Rentals Insurance? https://experimentrealestate.com/submit Get the FREE Mid-Term Rental Insurance Blueprint: https://experimentrealestate.com/#blueprint Welcome to the lab. Today, we're joined by Linda Holtz, a multifamily investor and property management expert who immigrated to the U.S. With ov…
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This week, we welcome Laura Clayton McDonnell, President of the Corporates Business Segment at Thomson Reuters. Laura shares her inspiring journey from corporate securities law to executive leadership at top technology companies, including Apple, Cisco, IBM, Microsoft, and now Thomson Reuters. She discusses how her Silicon Valley upbringing and her…
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Want to work with me and learn the power of Mid-Term Rentals Insurance? https://experimentrealestate.com/submit Get the FREE Mid-Term Rental Insurance Blueprint: https://experimentrealestate.com/#blueprint In this eye opening episode of In The Lab, Ruben unpacks the hidden truths behind what it really takes to succeed—across life, business, and rea…
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This week, we sit down with Kenzo Tsushima, Managing Director of Mind Factory at Morae, to discuss how AI is transforming legal operations and consulting services. Kenzo shares his unique career journey, blending a passion for technology with legal expertise, and highlights why the legal industry is positioned to leverage AI advancements more quick…
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Want to work with me and learn the power of Mid-Term Rentals Insurance? https://experimentrealestate.com/submit Get the FREE Mid-Term Rental Insurance Blueprint: https://experimentrealestate.com/#blueprint In this expansive and thought-provoking episode of In The Lab, Ruben breaks down a powerful concept that’s shifting the way high-level operators…
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This week we welcome Raghu Ramanathan, President of Legal Professionals at Thomson Reuters, for an insightful discussion on the profound impact of Artificial Intelligence (AI) on the legal industry. Raghu shares why he believes the legal sector, alongside healthcare, stands at the forefront of the AI revolution. His journey into the legal tech worl…
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Want to work with me and learn the power of Mid-Term Rentals Insurance? https://experimentrealestate.com/submit Get the FREE Mid-Term Rental Insurance Blueprint: https://experimentrealestate.com/#blueprint In this reflective and action-driven episode of In The Lab, Ruben dives into a transformative concept that has fueled much of his growth: the po…
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In this week’s Geek in Review, we sit down with Patrick Waldo, CEO of Unicorn Forms and proud Houstonian, to explore the intersections of data, document automation, and legal tech innovation. From the vibrant startup culture at Houston's ION and the Capital Factory's SXSW House event to the regulatory grind of form design, Waldo shares how his jour…
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This week, we sit down with Sam Flynn, COO and co-founder of Josef, to separate substance from hype in the rapidly evolving world of legal tech. Sam shares his passionate stance that “RAG is not dead,” defending Retrieval-Augmented Generation (RAG) as a foundational and still deeply relevant method for deploying AI in the legal industry—despite the…
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Want to work with me and learn the power of Mid-Term Rentals Insurance? https://experimentrealestate.com/submitGet the FREE Mid-Term Rental Insurance Blueprint: https://experimentrealestate.com/#blueprint In this reflective and action-driven episode of In The Lab, Ruben delves into the journey of achieving mastery—highlighting the hidden phase most…
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This week we sit down with Sean West—co-founder of Hence Technologies and author of Unruly: Fighting Back When Politics and Law Upend the Rules of Business. Together, they explore the shifting fault lines where law, technology, and geopolitics collide. From the growing reliance on generative AI in legal work to the erosion of rule of law and the em…
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