Coffee With Digital Trailblazers

StarCIO Digital Trailblazer Community

Recordings from the weekly Coffee with Digital Trailblazers that airs on LinkedIn Audio 11am ET every week. Join us at https://starcio.com/coffee Digital Trailblazers are product managers, DevOps engineers, agile leaders, data experts (scientists, governance, dataops), and other innovators driving transformations in their organizations and life. About the Coffee with Digital Trailblazers Every week we explore a topic and share lessons learned. All are welcome to attend, and please raise your hand to participate.

  1. National Entrepreneurship Week: Opportunities for Digital Trailblazers

    3D AGO

    National Entrepreneurship Week: Opportunities for Digital Trailblazers

    Isaac Sacolick, CEO of StarCIO, hosted an event featuring special guests including Dana Sanderson, Joanne Friedman, Liz Martinez, Joseph Puglisi, Martin Davis, John Patrick Luethe, Heather May, and Derrick Butts. The event focused on sharing insights from influential figures in the digital transformation sector, fostering valuable discussions. Chapters (00:00:00) - Coffee With Digital Trailblazers(00:00:18) - Coffee With Digital Trailblazers(00:02:01) - National Entrepreneurship Week(00:05:02) - Coffee Hour(00:05:24) - Pivot: The Entrepreneur's Story(00:06:02) - Tell me a Story about DevOps(00:09:13) - Making the Leap: Executive Search Company(00:12:39) - Exploring the Need for Continuity in Business(00:17:47) - What Pushed You To Take The Leap?(00:20:51) - Pushing the Big Leap(00:24:34) - Pivots and the Solopreneur(00:27:50) - Solo Entrepreneur: Change of Mindset(00:29:41) - Pivoting: Small Businesses(00:33:04) - John Stamatis on Leaving His Old World(00:33:43) - The Challenge of National Entrepreneur Week(00:34:42) - Coffee With Digital Trailblazers: Cross Functional Business(00:35:24) - Culture Fit and Managing AI Agents(00:36:20) - The Essential Sales and Marketing Skills for Digital Trailblazers(00:37:28) - Greed and the Next Wave of Digital Entrepreneurs(00:41:13) - Motivation and Risk in the Continuous(00:45:15) - Exploring Opportunities, Resilience and Risk(00:47:47) - Having a Board of Advisors(00:49:19) - What is a Solopreneur's First Expense?(00:50:34) - What is the Next Wave of Digital Entrepreneurs Need?(00:53:41) - A Few More Things I Learned From Starting a Startup(00:55:37) - Martin Cowen on Work-life balance(00:56:42) - Making Sure Your Clients Are On Track(00:58:10) - 8 Essential Elements for Selection of a Startup Market(01:00:02) - Coffee World: Digital Trailblazers

    1h 2m
  2. AI-First UX: Planning for the Evolution of GenAI-Enabled Customer Journeys

    JAN 31

    AI-First UX: Planning for the Evolution of GenAI-Enabled Customer Journeys

    The content discusses several sources and a host, Isaac Sacolick, during an event featuring experts in digital innovation. Key topics include Marriott's use of generative AI for search, Walmart's plans for AI integration in commerce, and insights into consumer AI trends and future projections, indicating a growing interest in immersive technology. Chapters (00:00:00) - Coffee With Digital Trailblazers: AI First(00:02:28) - The future of AI in customer experiences(00:06:50) - Digital Marketing and IT: The New Disciplines(00:07:35) - What's the Need for UX Designers in the Future?(00:10:11) - What's The Gap Between AI First User Experiences and Real-(00:15:17) - What Do Organizations Need to Do to Think About AI First?(00:17:37) - Alexa & Brand Governance(00:19:24) - The Design of Human Computers(00:20:34) - AI Managers: The Need for Experts(00:21:28) - What's The Wait for an AI First User Experience?(00:24:27) - Agents and the enterprise software landscape(00:25:18) - What Do We Need to Train for AI & UX?(00:31:19) - Coffee Hours: Skill Development and AI(00:33:47) - What other areas of skill development are important for students, for recent(00:36:25) - How to Build a Culture around AI(00:38:15) - Alexa, Google, and the Librarian(00:40:07) - Six Skills for AI & Safe Innovation(00:41:54) - The Need for Specialists in AI Architecture(00:44:33) - The Need for Change Management(00:45:12) - The Need for Cross Functional Teams in AI(00:46:56) - CXO meets AI: The New Experience(00:49:19) - The AI Agent Moment(00:50:53) - B2C Innovation and Governance(00:52:27) - Governance of AI and the Future(00:54:37) - When Will We See the Alexa Siri Moment?(00:55:56) - AI Web Standards(01:00:29) - Coffee with Digital Trailblazers

    1h 1m
  3. Talent Crunch: Developing Level-1 Expertise in the GenAI Era

    JAN 24

    Talent Crunch: Developing Level-1 Expertise in the GenAI Era

    The event, hosted by Isaac Sacolick, CEO of StarCIO, showcased notable digital trailblazers such as Elena Putilina, Joanne Friedman, Liz Martinez, Joseph Puglisi, Martin Davis, John Patrick Luethe, Heather May, and Derrick Butts, highlighting their contributions and innovations in the digital landscape. Chapters (00:00:02) - Talent Crunch and the Impact on Level 1 Expertise(00:04:57) - The Need for Level-One Expertise in AI(00:07:53) - "What is the most common phrase uttered by recent graduates?"(00:10:53) - The Need for More Learning in Software Engineering(00:11:49) - Hiring from AI(00:13:59) - What Should Security Students Know to Get Ready for the Future?(00:16:46) - CIO Network: Process and Operations Skills(00:19:59) - Seamanship: The Need for Subject Matter Experts(00:21:25) - Six Must-Have Skills in the CIO Skills Inventory(00:24:17) - CIO Network: What Skills Do We Need to Protect?(00:26:12) - The Need for Human In the Lead(00:28:57) - CISO Minute: The Need for Human Intelligence(00:31:03) - Coffee With Digital Trailblazers(00:33:19) - Fourth Industrial Revolution: What to Do With AI(00:36:47) - Mind Shift Around AI(00:39:53) - AI Trade Off-Management(00:41:15) - Apprenticeships for the AI Generation(00:43:09) - Change Management: AI Is Just a Tool(00:52:06) - Will IT staff become managers of AIs?(00:56:57) - Will AI Redefine Jobs?(00:59:40) - Coffee With Digital Trailblazers(01:00:29) - Winter Storms Coming to the US

    1h 1m
  4. CIO and CMO: Partnering on AI to Drive Growth

    12/05/2025

    CIO and CMO: Partnering on AI to Drive Growth

    Participants Hosted by Isaac Sacolick, CEO of StarCIO Special Guests Adrianna Hosford Elena Putilina Digital Trailblazers Joanne Friedman Liz Martinez Joseph Puglisi Martin Davis John Patrick Luethe Derrick Butts Heather May Summary Today’s panel explored AI’s role in driving revenue and growth through the collaboration between CIOs and CMOs, with discussions centered on customer education, data security, and cross-departmental partnerships. Participants shared their experiences and perspectives on AI implementation in marketing and IT, including the use of synthetic audiences, data analytics, and personalization strategies. The group emphasized the importance of forming cross-functional councils, establishing joint KPIs, and addressing security considerations while exploring future opportunities in areas like health tech and synthetic data. Transcript [00:00:00] Speaker A: Foreign. [00:00:05] Speaker B: Welcome to this week’s Coffee with Digital Trailblazers. Welcome back from the Thanksgiving weekend where we took Friday off and give everybody a break to be with family and to do your shopping and just to to veg out and watch some sports, maybe do some reading. And we are back here this week with a super special episode that I’m very excited about. We’ll be talking about the CIO and CMO relationship and more broadly the relationship between IT leaders and digital marketers and the digital trailblazing leaders in those groups. And how do we partner on AI not just to get more efficiencies or improve our workflow. How are we actually driving growth around this? And I think this is a very important episode. Thank you for joining this week. Part of the reason I’ve been excited about this episode is that we’ve been talking and I’ve been doing a lot of writing about how using AI only for productivity improvements, only for employee experiences and only for workflow gets translated to cost savings. Eventually the CFO catches up with that and gets and calls in the cards and says how are we going to actually realize the cost savings? And most of that ends up coming from headcount. And we’ve seen this rodeo before. For those of you who have led digital transformation efforts, you can’t modernize, you can’t transform by just becoming more efficient or just by improving productivity. You need to transform by using technology and now AI to a competitive advantage. And part of that is looking for ways to dri... Chapters (00:00:00) - CIO & CMO: The CIO-CMO Relationship(00:04:06) - CMO vs CIO: How to Partner with AI at Digital(00:07:00) - What Do You See as the Growth Opportunities in Working With Customers(00:10:13) - CIO Network: Growth Opportunities in the AI Era(00:15:31) - Top Executives: Growth Opportunities in AI(00:18:02) - CIO Network: CMO vs CIO(00:20:30) - CIO vs CMO: Shared Growth Mandate(00:22:33) - What is a Growth Mandate?(00:23:31) - CIO Network: CMO Growth Opportunities and CIO Relations(00:26:48) - Immersive Marketing: Synthetic Audience and Sentiment Analysis(00:30:04) - Coffee With Digital Trailblazers(00:31:53) - CIO and CMO Partner on AI to Drive Growth(00:32:47) - CMO Network: Safety & Security Is Everyone's Job(00:35:30) - CIO Network: The Future of Personalization in Marketing(00:36:52) - AI Partnership: Joint KPIs(00:38:28) - CIO vs CMO: Defining a Growth Mandate for(00:40:46) - Holistic IT: Data-centric Approach(00:44:20) - CMO & CIO Network: On AI(00:47:21) - How to Collaborate with AI in the Future(00:49:15) - Last Thoughts on SEO, AEO and Travel(00:52:01) - CIO Network: How to Build Growth Opportunities with CMO(00:52:39) - CMO & CIO Network: The Future of Data & Security(00:54:29) - AI in Healthcare: Partner on Patient Experience(00:57:36) - CIO Network: Health Tech and Patient Experience

    58 min
  5. AI for Social Good: Insights From Nonprofit Leaders

    11/14/2025

    AI for Social Good: Insights From Nonprofit Leaders

    Isaac hosted a special episode of “Coffee with Digital Trailblazers” focused on AI in nonprofits ahead of Giving Tuesday. Participants Hosted by Isaac Sacolick, CEO of StarCIO Special Guests – Non-profit executives Larry Lieberman, CEO of Mouse.org Stephen Rockwell, Chief Innovation Officer of Amplifi Teresa Duran, Technology Advisory Council of Big Brothers Big Sisters of America Glen Ford, Former Director of International Development and Trustee at Aegis Trust Derrick Butts, Board President and co-founder, Prostate Health Matters Digital Trailblazers Joanne Friedman Liz Martinez Joseph Puglisi Martin Davis John Patrick Luethe Summary Featuring a panel of nonprofit leaders discussing their experiences with AI tools to drive impact and reach donors. The episode explored various nonprofit use cases, including education, public benefits access, and health initiatives, with panelists sharing their experiences and challenges in implementing AI solutions. The discussion emphasized the importance of AI adoption in nonprofits, highlighting the need for strategic planning, collaboration with tech companies, and focusing on social impact rather than just efficiency. Transcript [00:00:05] Speaker B: Welcome to this week’s coffee with Digital Trailblazers, our 150th episode. I’m really excited to announce that I’m really excited to have a full house today, our largest speaker panel on this program and we’re talking about something really important to me. I am not an expert around nonprofits, but I have worked in nonprofits and we are heading into the holiday season. Giving Tuesday is coming up right after the Thanksgiving holiday. And in planning November’s episodes, I wanted to have just a special episode just talking about not only AI for social good, but just giving some of our nonprofit leaders the mic to talk about all the special things they’re doing to drive impact with their constituents, how they’re using AI, how they’re using technology to drive their cause, how they’re using AI and technology maybe to become more efficient, to reach a wider donor base and obviously to impact their social causes as well. I have five special guests today an... Chapters (00:00:00) - Coffee With Digital Trailblazers(00:02:42) - AI for Good: Impact on Nonprofits(00:05:02) - Machine Learning in the Classroom(00:07:52) - AI for Good with Stephen Rockwell(00:10:39) - AI Agents in the Nonprofit World(00:13:16) - Interview(00:13:39) - Glenn on AI and Non-profits(00:18:40) - Champions: Stories of Humanity(00:22:53) - CIO Network: Teresa Duran's Charity and AI(00:28:11) - Are Nonprofits Ready for AI?(00:31:40) - How Nonprofits are Using AI(00:36:15) - Coffee With Digital Trailblazers: AI for Social(00:37:24) - AI and Nonprofit Governance(00:40:27) - Steve Jobs on AI and the New Economy(00:41:42) - John and Larry on AI and Nonprofits(00:43:24) - Immigration of AI into Nonprofits(00:48:44) - Nonprofits and the AI revolution(00:50:53) - How to Get Funding for Your Nonprofit with Artificial Intelligence(00:52:26) - Working with a nonprofit in the AI world(00:56:54) - How to Prevent AI From Dehumanizing Nonprofits(00:58:45) - AI for Social Good

    1 hr
  6. AI Agents at Work: The IT and HR Alliance to Drive Adoption and Value

    10/31/2025

    AI Agents at Work: The IT and HR Alliance to Drive Adoption and Value

    In this episode of Coffee With Digital Trailblazers, the group takes a candid look at how AI adoption is reshaping the workplace—and what it means for people caught in the middle of change. Participants Isaac Sacolick Joanne Friedman Liz Martinez Derrick Butts Joseph Puglisi Martin Davis John Patrick Luethe Summary The conversation starts with HR challenges and the ongoing wave of tech layoffs, as Isaac reflects on shifting priorities toward adoption, value, and readiness for what’s next. The team compares recent industry moves by big tech players and unpacks how AI-driven automation is forcing both leaders and employees to adapt fast. Joseph and Joanne dig into the heart of change management, reminding everyone that culture—not just technology—determines success. Martin and Derrick weigh in on the ethical and human sides of layoffs, emphasizing empathy in leadership. Liz highlights how uncertainty and economic pressure demand personal growth and adaptability. The talk moves toward strategy, with Joanne focusing on the “why, how, and when” behind AI adoption and the value of human oversight in agentic systems. Isaac and John explore AI’s growing role in customer experience and security, noting that while automation boosts efficiency, human judgment still anchors trust. The episode wraps with reflections on collaboration across IT, HR, and business teams—and a look ahead to upcoming discussions on AI for social good and mental health. Transcript [00:00:01] Speaker A: Greetings everyone. Welcome to this week’s coffee with Digital Trailblazers. Happy Halloween and glad you are all here. We are going to give our normal two minutes of grace time to get everybody clicking and connecting. And I’m super excited for another one of our discussions around AI and AI agents and AI agents at work in this case and should be a fun and exciting discussion. Just share a little bit of personal news. I’m excited to announce that my course on LinkedIn, which is called Digital Transformation for Leaders in the AI Era, that came out, I think it was in July and that has now surpassed 3,000 people who have taken it. And I’m super excited for the response that the course has gotten. And if you have, if you have access to LinkedIn learning, you’ll see a URL pop up on the whiteboard on how to access the course. It’s about an hour and 15 minutes. It’s got a few sections on AI, it has a role playing test that you can go through that is AI oriented. It’s got a section on AI strategy, it’s got a whole bunch of other stuff. For all of you who are trying to sharpen your pencils about leading in this digital transformation era, want to say to hi to everybody who’s joining on the on the comments train. Holo Juanita hello David, Kristen... Chapters (00:00:01) - Coffee With Digital Trailblazers(00:00:34) - AI at Work: Digital Transformation for Leaders in the AI Era(00:02:28) - A More efficient Company with AI?(00:04:10) - IT Leadership: AI Announcements(00:09:58) - WSJDLive: The Future of AI Jobs(00:13:11) - How to Build a More AI-Driven Workforce(00:15:21) - AI Agents: Adoption, Collaboration(00:19:50) - On Board Now: The AI Strategy(00:21:41) - Are We Ready for Fully Autonomous AI Agents?(00:26:37) - AI Agents Will Be Autonomous From the Ground Up(00:28:05) - An AI Security Agent: How long will they be autonomous?(00:30:08) - Are You More Secure Than You Think You Are?(00:31:34) - SOC in the Machine Age(00:32:41) - Coffee With Digital Trailblazers(00:35:38) - HR Adoption, Valuing AI, and Change Management(00:37:39) - Do I Need an HR Department?(00:39:00) - CIO Network: Will AI Destroy Your Board?(00:41:40) - 3 Golden Rules for AI in the IT Organization(00:46:00) - In Attentivating AI Adoption(00:49:10) - SOC Analyses: Will AI Agents Replace the SOC Analyst?(00:51:43) - CIO Network: The Need for Innovation Talent(00:53:14) - AI Agents Enlisting Employees(00:54:23) - IT and HR: The AI Agent(00:57:56) - Top Executives: Blue Sky Strategy(01:00:20) - A Day in the Life of AI

    1h 2m
  7. The Co-Creation Mandate: How Partnerships Accelerate Innovation & Talent

    10/24/2025

    The Co-Creation Mandate: How Partnerships Accelerate Innovation & Talent

    In this episode of Coffee With Digital Trailblazers, we dive into the art of co-creation and what it really takes to build strong innovation partnerships. Participants Isaac Sacolick Juanita Olguin Jay Cohen Joanne Friedman Heather May Joseph Puglisi Martin Davis John Patrick Luethe Summary Our guests share honest insights on how companies, startups, and nonprofits can work together to drive progress—while still protecting intellectual property and managing risk. We talk about how to onboard partners the right way, set clear expectations, and avoid common collaboration pitfalls. You’ll hear real-world stories, from using drones in agriculture to building shared AI labs that spark breakthrough ideas. The panel also touches on preparing talent for an AI-first future, shifting mindsets toward collaboration, and creating space for creativity and trust to thrive. Transcript [00:00:00] Speaker A: Hello everyone. Welcome to this week’s coffee with Digital Trailblazers. We’re just having a fun discussion as I am here at my home today and we’ll be broadcasting next week’s session here from my home and then after that I will be in Berlin the week of first November 1st through 8th and currently planning to do the November 7th coffee hour from Berlin and hoping it all works out. But we’re all joking here because the 11am time slot in the Eastern time zone is 5pm over in Berlin and we’ll just need to figure out if we need to rebrand the coffee hour to something more appropriate like beer or Oktoberfest for digital trailblazers or something like that. We have a full house today, some special guests that I’ll announce in a few seconds seconds just waiting for everybody to be able to join in our conversation today which is going to be about the co creation mandate, how partnerships accelerate innovation and talent readiness and I’ll just give you a sense of how I’m picking topics out a little bit now. I’m looking at things that are have always been part of digital transformation efforts, whether it’s we did a session a few weeks ago around innovation versus governance and how do you balance the two. We’ve done sessions around change leadership and how change management is changing because of the speed and the capabilities of AI. And I wanted to cover the notion of the co creation mandate, the idea partnering because we’re still have this, I would say antiquated mindset that when it comes to new capabilities it’s a build versus buy decision. And I think that low code environments really sat and created a gray area between those two extremes. Over the last 15 years we’ve had to help our organizations break through the mindset that when we bring in partners when we’re not necessarily outsourcing, we are also looking for other opportunities to partner to develop capabilities together. Chapters (00:00:00) - Coffee With Digital Trailblazers(00:02:31) - What is the Co-Creation Mandate?(00:04:01) - Meet the CIOs of Star CIO(00:04:59) - What are the Key Differences Between Working With a Partner and Working Alone(00:07:33) - Co-Creation and Continuous Innovation(00:09:23) - Co-Creation vs. Single-Team Innovation(00:11:35) - Co-Creating: The Legal Hurdle(00:14:50) - Martin on Co-Creation(00:16:39) - In the Elevator: Co-Creating(00:17:47) - In the Elevator With Startups(00:18:55) - Is the Robot a Good Fit for Your Company?(00:20:26) - Robot-based manufacturing(00:21:52) - Co-Creation in the AI Industry(00:23:16) - What Do Companies Need To Do To Onboarding a Partner?(00:24:57) - Co-Leadership and Innovation(00:27:26) - Co-creation and the Business Cycle(00:33:35) - Coffee With Digital Trailblazers(00:35:37) - Top Executives: Why we're Accelerating Innovation and Co(00:37:05) - How to Bring New Innovation to the Company(00:39:42) - Co-Creation: Accelerating Innovation & Talent Readiness(00:43:25) - How To Identify the Right Partner to Accelerate Innovation(00:47:08) - How to Choose the Right Knowledge Ecosystem Partners(00:49:47) - Culture fit for innovation partners(00:53:38) - How to Find a Partner for Innovation(00:54:39) - Co-creation and Resilience(00:57:03) - Projects & Collaboration: The New Paradigm(00:58:22) - IT and HR Alliance: How Partners Can Accelerate Innovation

    1h 1m
  8. The Cost of Tribal Knowledge: Losing People Can Bring Ops to a Standstill

    09/26/2025

    The Cost of Tribal Knowledge: Losing People Can Bring Ops to a Standstill

    Discussion Topics Knowledge management has always been challenging. What are some of the technical, operational, and cultural barriers? Focusing on construction and manufacturing, in what areas are we most concerned about tribal knowledge and losing top people? What are the opportunities to close the knowledge gaps with technology and to better support AI initiatives? Participants Isaac Sacolick Bob Salaj Joanne Friedman Heather May Joseph Puglisi Martin Davis Derrick Butts John Patrick Luethe Liz Martinez Transcript [00:00:01] Isaac Sacolick: Greetings everyone. Welcome to this week’s coffee with digital trailblazers. This is episode 143 for us. We are going to take our usual slow ramp up to get everybody here on board and excited to talk about our topic today, the real cost of tribal knowledge. Why losing your people can bring OPS to a standstill. This is a conversation that we’ve actually danced around a few times at different coffee hours talking about how important it is to work with our staff and capture knowledge, create processes, move away from gray work. And I’m really excited to have Bob Salai here with us today as our expert and we’re just going to give it a few more minutes to everybody joins. I actually clicked the Go live button a little bit earlier than usual just to see what would happen. It’s always fun to Mess around with LinkedIn and make sure everything’s working before you get started. But really happy to see here folks. Say hello in the comments stream. Steve, thank you for getting that started and do want to hear your thoughts and your questions around knowledge management, around knowledge sharing and how we create processes. Hi Kristen, it’s good to see you again. Hi David. Kristen and I saw each other just a couple weeks ago. Kristen, I’m going to be right near you Oddly I’m going to text you later on my drive back from Tucson, Arizona back to San Diego. So Valaba, good to see you and everybody just say hello in the comments stream. This is an event I love to see people participating in especially this week. We’re talking about the real cost of tribal knowledge while losing your best people can bring OPS to a standstill and for everybody’s knowledge. Today’s episode is sponsored by Quickbase. Quickbase is an AI powered operations platform that is designed specifically for your unique processes and it’s not a one size fits all approach for those of you who are long term watchers and participants. You know we had a really interesting conversation, I think it was two or three months ago about the problems with Saspral and all these point solutions, the hundreds of different applications that exist in many enterprises and the impa... Chapters (00:00:01) - Coffee With Digital Trailblazers(00:03:11) - The challenges of knowledge management(00:03:51) - Lean Continuous Improvement in Construction(00:04:51) - Give Feedback, Get Feedback(00:06:14) - What's The Barriers to Knowledge Sharing?(00:12:29) - Organization in the IT Organization(00:13:49) - On Documentation and Process Automation(00:15:14) - Knowledge Management: Is it Too Complex?(00:19:43) - Construction and Manufacturing: The Digital Industrial Applications(00:20:53) - What are we most concerned about when we think about losing tribal knowledge(00:25:15) - On Loss of Skills(00:27:25) - CIO Network: Group Think and Learning(00:31:17) - Tribal Knowledge(00:32:43) - The Future of AI in the Construction Industry(00:36:12) - The Need for Documentation in the Security Industry(00:42:12) - Machine Learning for Maintenance: The Future of Tech(00:47:44) - Including Tribal Knowledge in the AI Process(00:52:27) - Standard Operating Procedures and Dynamic Work Management(00:54:56) - How to Make Tribal Knowledge Obsolete with Tech and AI(00:57:07) - Common Stream: The Real Cost of Tribal Knowledge(00:59:46) - Applying Quickbase to Construction Workflows

    1h 1m
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Recordings from the weekly Coffee with Digital Trailblazers that airs on LinkedIn Audio 11am ET every week. Join us at https://starcio.com/coffee Digital Trailblazers are product managers, DevOps engineers, agile leaders, data experts (scientists, governance, dataops), and other innovators driving transformations in their organizations and life. About the Coffee with Digital Trailblazers Every week we explore a topic and share lessons learned. All are welcome to attend, and please raise your hand to participate.

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