In this episode of the Shift AI Podcast, Yash Wagh, Co-Founder and CEO of Gone, joins host Boaz Ashkenazy to explore how reverse logistics and AI are transforming the secondhand goods market into a sustainable circular economy. With a background as a rocket engineer, supply chain leadership at Amazon and A.T. Kearney, and a passion for sustainability, Yosh is building autonomous local commerce infrastructure that keeps valuable goods out of landfills and in circulation.

From his journey as a mechanical engineer designing rocket propulsion systems to pioneering AI-powered reverse logistics, Yosh shares how Gone is solving the complex challenges of secondhand commerce. The conversation explores the business economics of circular economies, the role of AI in automating pickups and pricing, and a bold vision for a future where autonomous systems connect millions of households through local meshes of commerce. If you're interested in climate-conscious innovation, AI-powered logistics, sustainable consumerism, and the future of work in an AI-driven world, this episode offers invaluable insights from an entrepreneur building the infrastructure of tomorrow's circular economy.

Chapters

[00:00] Introduction and Welcome

[03:15] From Rocket Science to Reverse Logistics

[06:30] First Jobs and Career Journey

[10:45] What is Gone - Reverse Amazon Explained

[16:20] The Problem with Current Donation Models

[19:40] Business Economics and Unit Economics

[24:15] AI Technology and Automation in Action

[29:50] The Entrepreneurial Journey and Challenges

[35:10] Negotiating the Gone.com Domain Name

[37:45] The Future of Autonomous Local Commerce

[43:20] How to Connect with Gone

Connect with Yash Wagh

LinkedIn: https://www.linkedin.com/in/yashwagh/

Website: https://gone.com

Shop: https://shop.gone.com

Connect with Boaz Ashkenazy

LinkedIn: https://linkedin.com/in/boazashkenazy

Email: [email protected]

In this episode of the Shift AI Podcast, Christian Lund, Co-Founder of Templafy, joins host Boaz Ashkenazy to explore how cognitive collaboration between humans and AI is transforming enterprise document creation. Broadcasting from Copenhagen, Christian shares his unique journey from newspaper sales to building one of the leading document automation platforms serving over 800 enterprise clients worldwide, including KPMG and IKEA.

From navigating technology shifts spanning on-premise to cloud to AI, Christian offers invaluable insights on what separates successful AI implementations from the 40% of projects that fail. The conversation dives deep into why purpose trumps capability when deploying AI, how Templafy helps companies save millions annually while reducing risk, and the evolution from traditional templates to AI-powered document generation. Whether you're an executive trying to drive meaningful AI adoption or an entrepreneur building in the AI space, Christian's perspective on connecting human intent with AI intelligence offers a roadmap for the future of work.

Chapters:

[00:00] Introduction and Welcome

[02:00] Christian's Background and Journey to Templafy

[06:00] What Templafy Does: Enterprise Document Automation

[09:00] How AI Transformed Document Generation

[12:00] Why 40% of AI Pilots Fail and How to Succeed

[17:00] ROI and Multimodal Content Creation

[21:00] Advice for Deploying AI Agents

[26:00] Cognitive Collaboration: Humans and AI Working Together

[28:00] Job Displacement Concerns in Europe

[30:00] Two Words for the Future

Connect with Christian Lund

LinkedIn: https://dk.linkedin.com/in/christianlundcph

Website: https://templafy.com

Connect with Boaz Ashkenazy

LinkedIn: https://linkedin.com/in/boazashkenazy

Email: [email protected]

The Shift AI Podcast is syndicated by Geekwire and produced by Crumpled Ink Media

In this episode of the Shift AI Podcast, Michael Domanic, Head of AI at UserTesting, joins host Boaz Ashkenazy to explore how companies can successfully transform their organizations with AI. With over 800 custom GPTs built across UserTesting and nearly every employee actively using AI tools, Michael shares the framework behind one of the most successful enterprise AI transformations happening today.

From his early days designing chatbots during the first AI hype cycle to leading transformation at scale today, Michael offers invaluable insights into why AI transformation is fundamentally a change management and creative challenge—not just a technological one. The conversation delves into the responsibility companies have to their workforce during this historic transformation, the importance of democratizing AI access, and why focusing on human creativity and experimentation is the key to unlocking real value. If you're looking to understand how to drive meaningful AI adoption in your organization while keeping humanity at the center, this episode is essential listening.

Chapters:

[00:00] The Human Side of AI and Creativity

[02:00] Michael's Background and the First Chatbot Wave

[04:00] First Jobs: From Lifeguard to Telemarketer

[05:00] What is UserTesting and How It Works

[08:00] The Challenge of Enterprise AI Adoption

[11:00] Why Multiple AI Models and 800+ Custom GPTs

[15:00] Change Management Over Technology

[19:00] AI's Impact on Jobs and Employee Responsibility

[22:00] Growth Mindset vs. Scarcity in AI Strategy

[24:00] Healthcare and the Future of AI

[27:00] Two Words for the Future: Human and Creativity

[29:00] Measuring ROI in AI Transformation

Connect with Michael Domanic

LinkedIn: https://linkedin.com/in/michaeldomanic/

Connect with Boaz Ashkenazy

LinkedIn: https://linkedin.com/in/boazashkenazy

Email: [email protected]

In this episode of the Shift AI Podcast, Jeff Reihl, Technology Chairman at LexisNexis and former CTO, joins host Boaz Ashkenazy to discuss how one of the world's largest legal information companies executed a dramatic pivot to generative AI. Jeff shares the remarkable story of how LexisNexis transformed their entire 2023 strategy in response to ChatGPT's emergence, leveraging their 160 billion document repository to solve AI hallucination problems that plague the legal profession.

From modernizing mainframe systems written in IBM assembly language to implementing multi-model AI strategies using GPT and Claude, Jeff provides a masterclass in enterprise AI adoption. The conversation explores critical topics including maintaining trust and accuracy in legal AI applications, the evolving role of junior lawyers in an AI-augmented world, and how LexisNexis achieved 300% ROI for their customers while dramatically accelerating their own internal processes. Whether you're leading digital transformation at an established enterprise or simply curious about how AI is reshaping professional services, this episode offers invaluable lessons from the frontlines of the legal AI revolution.

Chapters

[01:40] Jeff's Background and Career Journey

[05:54] LexisNexis, RELX, and the Legal Information Industry

[07:21] The ChatGPT Revolution and Strategic Pivot

[10:17] Solving the Hallucination Problem with RAG

[13:26] Liability, Accountability, and the Role of Legal Professionals

[16:16] ROI Metrics and Customer Adoption

[21:02] Agentic Workflows and Strategic Partnerships

[26:18] The Future of Junior Lawyers and Legal Education

[29:05] The Future of Work and Software Development

[31:33] Framework for AI Integration in Organizations

[34:46] Two Words for the Future: Transformative and Personalized

Connect with Jeff Reihl

https://www.linkedin.com/in/jeffreihl/

Connect with Boaz Ashkenazy

LinkedIn: https://linkedin.com/in/boazashkenazy

Email: [email protected]

In this episode of the Shift AI Podcast, Alvin Graylin, Digital Fellow at Stanford’s Institute for Human-Centered AI and creator of the Abundantism framework, joins host Boaz Ashkenazy for a bold and wide-ranging conversation on the future of AI and humanity. With a background that spans investing, international leadership, and advanced academic research, Alvin offers a rare, global lens on how we can — and must — steer AI toward positive societal outcomes.

Together, Boaz and Alvin explore three potential AI futures — from Mad Max to Star Trek — and discuss how we can avoid a descent into dystopia by reframing our economic systems, rethinking employment, and redefining human value. The conversation touches on the AI Bill of Rights, the risks of sovereign “gladiator AIs,” and how a new GI Bill for the AI age could help millions transition into a post-labor economy.

If you’re curious about AI’s geopolitical risks, employment disruption, or how we might architect a truly abundant society, this is an essential listen.

Chapters

[01:55] Alvin Graylin's Background: Stanford, XR, Global Ventures

[05:13] Why the Next 5–10 Years Matter for Humanity

[08:04] The Three Futures: Mad Max, Elysium, and Star Trek

[13:33] “Winning the Wrong Race” — The AGI Race and Policy Pitfalls

[17:02] The Real Threat: Bad Actors and Rogue AI Use

[18:40] AI and the Collapse of Traditional Employment

[20:39] What 15–25% Unemployment Could Mean for Society

[23:02] The AI Bill of Rights and the Need for New Protections

[27:10] Surveillance, Data, and Manipulation Risks

[29:52] From Scarcity to Abundantism: The Shift in Mindset

[32:40] Guardian AI vs Gladiator AI: What We Should Be Building

[35:04] The GI Bill for the AI Age and the Need for Soft Landings

[42:03] Start / Stop / Keep: Alvin’s Advice to Tech Leaders

[45:49] Redefining Value: The Two Words That Shape the Future

Connect with Alvin Graylin

LinkedIn: https://www.linkedin.com/in/agraylin/ X (formerly Twitter): https://twitter.com/agraylin

Connect with Boaz Ashkenazy

LinkedIn: https://linkedin.com/in/boazashkenazy Email: [email protected]

The Shift AI Podcast is syndicated by Geekwire and produced by Crumpled Ink Media.

Special thanks to Augmented AI Labs and Clause for sponsoring this episode.

In this episode of the Shift AI Podcast, Court Lorenzini, the founding CEO of DocuSign and now founder of Founder Nexus, joins host Boaz Ashkenazy for a thought-provoking conversation about entrepreneurship, AI, and building a more balanced future for humanity. As a five-time entrepreneur who has experienced both spectacular success and instructive failure, Court brings a unique perspective on how artificial intelligence is fundamentally changing what it takes to build and scale companies today.

From the isolation of the founder's journey to reimagining education systems for an AI-driven world, Court shares his vision for creating abundance rather than scarcity. The conversation explores how AI could be humanity's greatest tool for leveling the playing field, the importance of founder communities, and why we need to rethink our approach to work, purpose, and human dignity. If you're interested in understanding not just the business implications of AI but its profound societal impact, this episode offers invaluable insights from someone dedicated to helping founders succeed while building the future we all want to live in.

Chapters

[02:06] Court's Background and Entrepreneurial Journey

[04:27] The First Paycheck and Worst Job Stories

[07:34] Introducing Founder Nexus and the Founder's Journey

[11:31] How AI is Changing Startup Requirements

[14:04] The Challenge of Differentiation in the AI Era

[17:11] The Lifecycle of Employment and Societal Impact

[20:06] Rethinking Education for an AI Future

[26:16] Dystopian vs Utopian AI Futures

[30:25] What Court is Most Excited and Scared About

[33:30] Creating Abundance Over Scarcity

Connect with Court Lorenzini

LinkedIn: https://linkedin.com/in/court-lorenzini-333447/

Connect with Boaz Ashkenazy

LinkedIn: https://linkedin.com/in/boazashkenazy

Email: [email protected]

The Shift AI podcast is syndicated by Geekwire and produced by Crumpled Ink Media.

In this special live episode of the Shift AI Podcast recorded at Seattle AI Week, Dr. Andre Alfred, who leads threat operations and security for Google Cloud's Fortune 500 customers, joins host Boaz Ashkenazy for an eye-opening conversation about the intersection of AI and cybersecurity. With his remarkable journey from high school help desk operator to earning his PhD and leading security operations at Microsoft, Oracle, and Google, Andre brings a unique perspective on protecting critical infrastructure in an era where adversaries have access to the same powerful AI tools as defenders.

From data poisoning threats that could compromise healthcare diagnostics to the challenges of securing physical infrastructure like water systems and power grids, Andre shares what keeps him up at night and why two-factor authentication isn't optional anymore. The conversation explores how AI is transforming both offensive and defensive capabilities in cybersecurity, why the next generation of jobs will be defined by leaders rather than technology, and Andre's commitment to visibility as an African American leader in tech. Through his scholarship program at Western Governors University, Andre is opening pathways for the next generation of cybersecurity and healthcare professionals. If you're wondering about the real security threats we're not thinking about—and why the future of work requires "more focus"—this conversation offers crucial insights from someone defending some of the world's most critical systems.

Chapters

[00:00] Introduction and Boaz's Journey to the Shift AI Podcast

[02:37] Andre's Background and Role at Google Cloud Security

[03:44] The Non-Traditional Path: From Help Desk to PhD

[06:25] The Decision to Return to College and Transform Your Career

[08:41] From Capital One to Microsoft to Google

[12:03] What It's Like to Wake Up Every Morning in Threat Operations

[14:21] The Bittersweet Reality: When Innovation Can Be Weaponized

[15:31] Data Poisoning and Healthcare: The Threat We're Not Thinking About

[18:37] Teaching Kids to Question What They See Online

[20:06] Physical Infrastructure Vulnerabilities and Social Engineering

[24:09] The Future of AI and Cybersecurity in 2030

[26:24] Creating Jobs of the Future Through Education

[29:41] The Intersection of Cybersecurity and Healthcare

[32:29] Leaders Must Define the Next Jobs, Not Let Technology Define Them

[33:36] Being Visible as an African American in Tech

[36:11] Two Words for the Future: "More Focus"

Connect with Dr. Andre Alfred

LinkedIn: https://www.linkedin.com/in/aoalfred/

Connect with Boaz Ashkenazy

LinkedIn: https://linkedin.com/in/boazashkenazy

Email: [email protected]

Special thank you to Western Governers University for hosting and sponsoring this live episode at the Labor Temple in Seattle WA during AI Week.

In this episode of the Shift AI Podcast, Will Jung, Chief Technology Officer at nCino, joins host Boaz Ashkenazy to explore how artificial intelligence is revolutionizing the traditionally conservative banking and financial services sector. Jung brings a distinctive perspective from his extensive experience helping financial institutions transition from viewing technology as a cost center to embracing it as a strategic innovation driver, particularly in the highly regulated world of banking.

From fraud prevention using AI agents that actively lure scammers to context engineering that personalizes banking experiences, Jung offers compelling insights into how banks are deploying cutting-edge technology while maintaining trust and regulatory compliance. The conversation examines the delicate balance between rapid technological advancement and responsible innovation, the future of personalized banking relationships, and why staying human remains the most critical factor in an increasingly automated world. If you're interested in understanding how one of the most regulated industries is navigating the AI revolution while serving underbanked populations and protecting customer data, this episode delivers essential perspectives from a technology leader at the forefront of financial innovation.

Chapters:

[02:00] Will's Background in Banking Technology

[03:00] nCino's Mission in the FinTech Space

[04:30] Banks Embracing Technology as Innovation Driver

[06:50] Fighting Fraud with Advanced AI Technology

[09:00] Building Technical and Non-Technical Team Culture

[11:50] Context Engineering in Banking

[14:25] Privacy and Personalization Trade-offs

[19:20] The Future Customer Experience in Banking

[21:30] Societal Implications of AI Technology

[25:50] Cryptocurrency and Banking Technology

[27:50] Two Words for the Future: Stay Human

[30:00] The Human Element in Automated Banking Decisions

Connect with Will Jung

LinkedIn: https://www.linkedin.com/in/will-jung/?originalSubdomain=au

Connect with Boaz Ashkenazy

LinkedIn: https://linkedin.com/in/boazashkenazy

Email: [email protected]

In this episode of the Shift AI Podcast, Venky Veeraraghavan, Chief Product Officer at DataRobot, joins host Boaz Ashkenazy to explore the fascinating evolution from predictive AI to today's agentic workflows. With 20 years of experience at Microsoft working on everything from Azure Machine Learning to the early days of Azure OpenAI, Venky brings a unique perspective on how AI is truly transforming the enterprise landscape.

The conversation delves into the fundamental differences between predictive and generative AI, how agents will orchestrate complex business processes using multiple AI tools, and what the future holds for the agentic workforce. From warehouse management systems that adapt in real-time to supply chain planning agents that combine forecasting with live data, Venky shares insights on how the orchestration layer of multiple AI tools creates genuinely transformative possibilities.

If you're interested in understanding how enterprises are navigating AI adoption with appropriate caution and what it takes to thrive in an AI-driven workplace, this episode offers invaluable insights from someone at the forefront of enterprise AI transformation.

Chapters

[00:00] Introduction and Background

[02:00] Venky's Journey from Microsoft to DataRobot

[05:00] Predictive vs Generative AI Explained

[09:00] The Evolution of DataRobot's Platform

[13:00] Function Calling and Orchestration Layers

[15:00] The Future of Agentic Workflows

[18:00] Agent Workforce Management and UI Challenges

[23:00] The Human Impact of AI Transformation

[28:00] Enterprise Adoption and Brand Risk

[30:00] Two Words for the Future: Exciting and Disruptive

Connect with Venky Veeraraghavan

https://www.linkedin.com/in/venkyv

Connect with Boaz Ashkenazy

LinkedIn: https://linkedin.com/in/boazashkenazy

Email: [email protected]

In this episode of the Shift AI Podcast, Vik Bajaj, CEO and Co-founder of Foresite Labs and Interim President at Xaira Therapeutics, joins host Boaz Ashkenazy to explore how AI is revolutionizing life sciences and healthcare. With a distinguished background spanning physics, structural biology, radiology at Stanford, and pioneering work at Google, Vik brings a unique perspective on the intersection of AI and medicine.

The conversation delves into the stark realities of drug discovery—where 2 million researchers globally struggle against success rates so low that most will be lucky to contribute to one or two successful drugs in their entire careers. Vik explains how AI, particularly David Baker's groundbreaking protein design work, is poised to transform this landscape by enabling drugs for previously "undruggable" targets and moving healthcare from reactive treatment to predictive, personalized medicine.

From genetic tests that could provide actionable insights for 75% of people to AI models that can predict 5-year mortality from a simple chest X-ray, this episode reveals how we're approaching a future where disease prevention replaces disease treatment. If you're interested in understanding how AI will fundamentally reshape healthcare economics and why Vik compares this transformation to the industrial revolution, this episode is essential listening.

Chapters:

[01:48] From Physics to Life Sciences: Vik's Interdisciplinary Journey

[04:13] The Google Years: Early AI Revolution in Science

[06:56] Xaira Therapeutics and David Baker's Protein Design Breakthrough

[09:28] The Optimistic Future of AI in Drug Discovery

[15:17] The Four-Stage Evolution of AI in Medicine

[19:53] Healthcare Cost Crisis and AI Solutions

[23:27] The Promise of Personalized Medicine

[28:39] Foresite Labs: Specializing in Science and Engineering AI

[32:00] Why Healthcare AI is Harder Than Software Engineering

[36:27] Two Words for the Future: Industrial Revolution

Contact Info:

Connect with Vik Bajaj

● LinkedIn: https://www.linkedin.com/in/drvikbajaj/

Connect with Boaz Ashkenazy

● LinkedIn: https://www.linkedin.com/in/boazashkenazy

● X: boazashkenazy

● Email: [email protected]