
The Jen Gottlieb Show
What if today was the day you dared yourself to do what you've always wanted? Welcome to the Jen Gottlieb Show! Each week, join your host, Jen Gottlieb, for powerful, punchy episodes that will leave you inspired to dream big and live boldly. If you are ready to create change in your life, this podcast is a must-listen. Be ready to laugh, learn and take action to become who you were always meant to be. It's time to step out of your comfort zone and into your best life...one dare at a time.
Latest episodes

Feb 11, 2025 • 54min
The Fund XX's Gabriela Isturiz on AI, Scaling, and Empowering Women Entrepreneurs
Gabriela Isturiz, a trailblazing legal tech entrepreneur and co-founder of The XX Fund, dives into the impact of generative AI on the legal landscape. She reveals the common pitfalls of mislabeling products as 'AI-powered' without real value. The discussion shifts to the hurdles of scaling legal tech businesses and the pressing need for women-led investments. Gabriela emphasizes the importance of supporting minority founders and shares her transformative journey from a stable job to entrepreneurship, advocating for intentional investments in diverse talent.

Feb 3, 2025 • 60min
Unlocking Your Power Zone: Karen & David Skinner on Thriving in Legal Practice
Karen Dunn Skinner and David Skinner, founders of Gimbal Consulting, delve into optimizing legal workflows and enhancing productivity while preventing burnout. They introduce the concept of the Power Zone, focusing on tasks lawyers are uniquely skilled at and passionate about. The discussion covers strategic delegation using the Delegation Quadrant and the role of AI in streamlining legal tasks. They emphasize adapting to technology, enhancing work-life balance, and transforming legal practices for a more fulfilling career.

Jan 27, 2025 • 36min
The Evolution of AI in Legal Tech: A Conversation with ContractPodAi's Atena Reyhani
In a dynamic discussion, Atena Reyhani, Chief Product Officer at ContractPodAi and a legal tech innovator, shares her insights on AI's evolution in the legal industry. She highlights the rise of conversational user interfaces that simplify user experience and enhance adoption. Atena predicts a future collaboration between humans and AI agents, emphasizing the shift from basic chatbots to comprehensive solutions. She also addresses the need for diversity in AI development and how it drives innovation while tackling challenges in aligning AI with business goals.

8 snips
Jan 20, 2025 • 27min
From Workflow to Innovation: Bloomberg Law Answers and AI Assistant with Bobby Puglia
Join Bobby Puglia, Chief Product Officer at Bloomberg Industry Group, as he discusses the transformative potential of AI in legal research. He addresses the issues of 'tool fatigue' and shares strategies to enhance tech adoption among lawyers. Bobby explains how Bloomberg Law Answers offers direct, concise legal insights with proper citations, simplifying workflow. The conversation also touches on refining tools through user feedback and the importance of aligning technology with diverse legal needs, paving the way for innovative future advancements.

Jan 13, 2025 • 45min
Patrick Ip: How Theo AI is Redefining Legal Predictions
Patrick Ip, co-founder and CEO of Theo AI, has a fascinating background that includes stints at Google and the United Nations. In this insightful conversation, he shares how AI is revolutionizing legal predictions and workflows. He discusses a notable pro se lawsuit where AI tools were crucial in drafting legal documents, pointing out both opportunities and risks. Patrick also reflects on his entrepreneurial journey and the ethical challenges of integrating AI into legal practices, emphasizing the importance of data-driven decision-making in the evolving legal landscape.

Jan 6, 2025 • 41min
Summarizing Success with Summize's Tom Dunlop and Laura Proctor
Tom Dunlop, CEO and founder of Summize, and Laura Proctor, its Chief Marketing Officer, share insights into their innovative contract lifecycle management tool. Tom reveals how his frustrating experiences as an in-house lawyer sparked the creation of Summize to simplify contract reviews. Laura discusses their strategy of embedding tools within platforms like Word and Slack, enabling seamless collaboration. They also explore the future of legal tech, highlighting the transformative role of AI in enhancing efficiency and reshaping perceptions of legal teams as enablers rather than bottlenecks.

7 snips
Dec 30, 2024 • 43min
50 Episodes of Legal Innovation and a Chat with Google NotebookLM
This unique discussion dives into the transformative effects of generative AI within the legal sector. It highlights the importance of ethical AI use and the evolution of client-centric practices. The conversation emphasizes the balance between technology and mental health, and the significance of collaboration for social impact. Additionally, experts share insights on the need for emotional intelligence and new skills for lawyers in a tech-driven future. A light-hearted recap reflects on key themes and innovative tools shaping the industry's landscape.

Dec 23, 2024 • 53min
Sarah Glassmeyer and Niki Black on Legal Tech in 2024 – Highlights, Hiccups, and Hopes for 2025
Legal tech experts Sarah Glassmeyer, Director of Data Curation at Legal Technology Hub, and Niki Black, Principal Legal Insight Strategist at AffiniPay, dive into the evolving landscape of AI in the legal field. They discuss the impact of generative AI on legal research, evaluating its reliability amid concerns about bias and user trust. The conversation highlights challenges in adopting AI within law firms, the potential of recent acquisitions to drive innovation, and the urgent need for legal education to adapt to these technological changes.

Dec 16, 2024 • 41min
Harnessing AI for Litigation: Mark Doble on Alexi’s Next Evolution
Mark Doble, Co-Founder and CEO of Alexi, brings a blend of legal expertise and software engineering to the table. He discusses the impact of AI on the legal industry, particularly in enhancing productivity for remote teams. Doble explains how Alexi automates tedious tasks, allowing lawyers to focus on strategic thinking. He also touches on the role of AI in mentoring junior associates and emphasizes the growing importance of human judgment in an increasingly automated landscape. Security concerns around data usage in AI tools are also addressed.

Dec 9, 2024 • 41min
Communication, AI, and the Human Side of Law: Insights from Smokeball’s Jane Oxley
Jane Oxley, Chief Revenue Officer at Smokeball, discusses the intersection of communication and AI in legal practices. She reveals how effective communication structures can reflect organizational health while highlighting the unique challenges faced by smaller law firms. Jane explains how Smokeball’s AI tool, Archie, automates routine tasks, boosting productivity. The conversation also addresses the ethical implications of AI in law and the need for maintaining human connections, especially in the evolving expectations of clients in the digital age.
Remember Everything You Learn from Podcasts
Save insights instantly, chat with episodes, and build lasting knowledge - all powered by AI.