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Coffee With Digital Trailblazers

Coffee With Digital Trailblazers

By: StarCIO Digital Trailblazer Community
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About this listen

 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. Topics that we cover: digital transformation, AI. genAI, AI agents, agile, DevOps, data science, data governance, IT leadership, CIO, CDO, CMO, CHRO© StarCIO
Episodes
  • Developing Your Personal Brand: Best Practices From Thought Leaders

    Developing Your Personal Brand: Best Practices From Thought Leaders
    Apr 10 2026
    This episode of Coffee with Digital Trailblazers, hosted by Isaac Sacolick, features a discussion on personal branding and thought leadership in technology. Key speakers shared their experiences and best practices, emphasizing authenticity, consistency, and gradual progress in building a personal brand, likening the journey to a marathon rather than a sprint. Chapters
    • (00:00:01) - Coffee With Digital Trailblazers
    • (00:01:17) - A toast to Thought Leaders at the Coffee Hour
    • (00:03:20) - A Taste of the Blog
    • (00:04:48) - Lead From The trenches: My
    • (00:10:07) - How to Build a Brand Through Digital Speaking
    • (00:12:20) - CIO Network: The First Moment
    • (00:17:38) - CIO Confessions: Personal Brand
    • (00:21:12) - Speaking Out Loud
    • (00:23:14) - Cyber Resilience: The 5 Ps
    • (00:25:08) - Cyber Resilience: The challenge of communicating your message
    • (00:28:59) - Have You Got a Brand?
    • (00:34:19) - Developing Your Personal Brand
    • (00:36:11) - Coffee Hour for Introverts
    • (00:40:50) - Heather's Advice for Publishers
    • (00:42:48) - How to Build a Brand on LinkedIn
    • (00:47:16) - How to Build a Personal Brand
    • (00:49:54) - Caffeine Hour: Nora's Journey
    • (00:50:32) - What are some of the realities people should have as they're embark
    • (00:53:59) - Derek Martin on Spelling Your Brand
    • (00:57:05) - Writing for Social Networking
    • (00:57:43) - How to Build a Brand with Your Friends
    • (00:58:27) - A Week in the Life of Band
    • (00:58:50) - AI Coding Competencies
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    1 hr
  • Managing AI Agents: New Skills, Operating Models, and Tools

    Managing AI Agents: New Skills, Operating Models, and Tools
    Mar 20 2026
    In a recent episode of "Coffee with Digital Trailblazers," participants discussed the management of AI agents. Host Isaac Sacolick and guests debated whether organizations should treat AI agents like employees. Insights highlighted concerns over performance management approaches, emphasizing the need for governance and effective monitoring of AI capabilities. There's a growing consensus that stronger oversight frameworks are essential for the responsible deployment of AI agents in enterprises. Chapters
    • (00:00:00) - Coffee With Digital Trailblazers
    • (00:01:16) - How to Manage AI Agents
    • (00:02:26) - Will AI Agents Get the Accountability They Deserve?
    • (00:06:10) - AI Agents Boot Camp
    • (00:10:10) - How to Manage AI Agents
    • (00:11:01) - Should We Manage AI Agents Like Employees?
    • (00:15:12) - Decision Management in the AI Era
    • (00:16:29) - Is There a Rogue AI?
    • (00:24:41) - Should We Manage An AI Agent Like a Person?
    • (00:29:08) - Should We Manage AI Agents? (2 Votes
    • (00:31:22) - Coffee With Digital Trailblazers
    • (00:33:15) - How to Monitor and Control AI Agents
    • (00:36:30) - Are You Going to Put AI Agents Through Performance Management?
    • (00:39:52) - How to Manage AI Agents?
    • (00:44:03) - Security Executive Forum: Artificial Intelligence Agents and Threats
    • (00:49:35) - Machine Learning and Continuous Testing
    • (00:51:44) - Agile Leadership Skills, Operating Model Shift and Tech Capabilities
    • (00:55:26) - What an AI Native Professional Looks Like
    • (00:56:35) - AI native professionals: What's the Future of Product Management?
    • (00:58:22) - A Taste of the 2019 Star CIO workshop on AI
    • (00:59:53) - Add to Calendar
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    1 hr
  • National Entrepreneurship Week: Opportunities for Digital Trailblazers

    National Entrepreneurship Week: Opportunities for Digital Trailblazers
    Feb 20 2026
    Participants Hosted by Isaac Sacolick, CEO of StarCIO Special Guests Tyler James Johnson Digital Trailblazers Joanne FriedmanLiz MartinezJoseph PuglisiMartin DavisJohn Patrick LuetheHeather MayDerrick Butts Summary The episode focused on discussing entrepreneurship and the challenges of becoming a solopreneur, freelancer, or startup founder. Isaac hosted a panel of experienced entrepreneurs, including Tyler, Heather, Derek, Liz, Joanne, Martin, John, and Joe, who shared their personal stories and insights about taking the leap into entrepreneurship. The panelists discussed topics such as resilience, risk management, experimentation, and the importance of having a clear business model and market fit. They emphasized the need for networking, honest advisors, and a well-thought-out go-to-market strategy. The conversation also touched on the financial and personal challenges of entrepreneurship, including healthcare costs and work-life balance. The panelists agreed that while entrepreneurship can be rewarding, it requires careful planning, a strong support system, and a willingness to adapt and learn from failures. StarCIO Research Sources 80% of small business owners say they would still start their business if they had to do it over again. U.S. BankTotal full-time self-employment in the U.S. hit its highest annual level on record in 2025, with about 16.77 million people self-employed full-time – SBE CouncilTotal Entrepreneurial Activity in the U.S. is at a historic high: 19% of adults are actively starting or running a new business – GEMGlobally, roughly 20% of adults are involved in entrepreneurial activity, around 582–665 million people. TKG•40% see good opportunities but won’t start a business because of fear of failure 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
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    1 hr and 2 mins
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