Expert Intelligence with Paul Estes

What the AI Shift Means for Your Career with Kelly Monahan

Kelly Monahan, Managing Director of Upwork's Research Institute and co-author of Essential, reveals why 77% of employees feel AI makes work harder, not easier—and what leaders can do about it. In this eye-opening conversation with Paul Estes, Kelly breaks down the real forces behind today's labor market shifts, from inflation and capital costs to the pandemic's lasting impact on customer behavior.
From her research on the frontlines of the future of work, Kelly shares practical frameworks for moving beyond resilience to "anti-fragility"—the ability to adapt and evolve when systems face stress and shock. Whether you're a leader trying to implement AI effectively or a professional wondering how to stay relevant, this conversation offers actionable insights on navigating our rapidly changing work landscape while keeping human creativity and relationships central.
You'll Learn:
Why the AI productivity paradox is happening and how to overcome it
The difference between AI as a tool versus AI as a teammate, and what it means for your workflow
How to move from fragile to anti-fragile thinking when facing career disruption
Why skills are becoming more valuable than degrees and how to credential them effectively
The "configuration mindset" that separates AI power users from frustrated beginners
How to preserve cognitive capacity for creativity in an increasingly automated world
What successful organizational AI strategies look like beyond mere cost-cutting
References Mentioned:
Essential by Christie Smith and Kelly Monahan
Antifragile by Nassim Nicholas Taleb
The Black Swan by Nassim Nicholas Taleb
Thinking, Fast and Slow by Daniel Kahneman
Subscribe to Expert Intelligence so you don't miss future conversations with industry leaders at the forefront of technological transformation. Each episode brings you practical insights to navigate our rapidly evolving digital landscape.
Producer: David Grabowski Theme Music: Aleksey Chistilin

Building Resilience in Uncertain Times with Samia Kornweibel

Generation X professionals are navigating an unprecedented perfect storm: young children at home, peak career responsibilities, and a business landscape in constant flux. Executive coach Samia Kornweibel joins Paul Estes to explore why so many mid-career leaders are experiencing what she calls "career meltdowns"—and how they can build resilience in an era where roles keep shifting.
Fresh from completing her AI coaching certification, Samia shares how she's helping leaders navigate the ethical integration of AI tools while maintaining the human connection that drives real transformation. Using Microsoft's suite of tools and her innovative CHAIR model (Clarity, Humanizing, Aligning, Integrating, Realizing), she demonstrates how coaches can responsibly leverage technology to enhance the coaching relationship.
You'll Learn:
Why Generation X is experiencing "career meltdowns" at the intersection of family, career peak, and rapid change
The "musical chairs" reality of modern corporate life and how to build resilience when stability isn't an option
How to create and maintain psychological safety as an intentional daily practice, not a one-time achievement
The CHAIR model for responsible AI integration in professional coaching and development
Why human accountability and connection remain irreplaceable in an AI-enhanced world
Practical strategies for using tools like Microsoft Viva Insights to enhance coaching conversations and time management
How to move from peripheral AI conversations to focused, ethical implementation
Subscribe to Expert Intelligence so you don't miss future conversations with industry leaders at the forefront of professional development and workplace transformation. Each episode brings you practical insights to navigate our rapidly evolving career landscape.
Producer: David Grabowski Theme Music: Aleksey Chistilin

AI's Role in Personalized Math Tutoring with Peter Relan

Peter Relan, founder of the YouWeb Incubator and initial Discord investor, joins Paul to discuss how AI transforms math education through his latest venture, MathGPT.ai. Growing up in poverty with parents who believed in education's transformative power, Peter is now paying it forward by creating around-the-clock math coaching for students facing critical academic hurdles.
In this eye-opening conversation, Peter reveals how his platform combines AI tutoring with human instructor oversight to address math numeracy challenges while maintaining academic integrity. From Peter's journey as a UCLA math tutor to his vision of personalized learning through AI coaches, discover how technology creates accessible, accurate, and cheat-proof math education that helps students overcome gateway barriers to their chosen careers.
You'll Learn:
How math courses often become gateway blockers that prevent students from entering their chosen careers
Why "innumeracy" is becoming a critical societal challenge comparable to illiteracy
The instructor-led approach that makes MathGPT.ai cheat-proof while still helping students learn
How AI can provide personalized learning experiences based on students' unique interests
Why the future of education lies in the partnership between human wisdom and artificial intelligence
The analytics dashboard that helps instructors identify struggling students in real-time
How AI can automate time-consuming workflows while preserving the irreplaceable human touch in education
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Mastering Career Chaos with Christopher Bishop

Christopher Bishop, a self-described "nonlinear multimodal careerist" who's navigated eight careers, joins Paul Estes to discuss his new book Improvising Careers: Succeed in Jobs That Don't Exist Yet (pre-order here). From touring rock musician opening for the Eagles to IBM executive to quantum technology expert, Christopher shares how to thrive in a world where the average person will have 8-10 jobs by age 38.
In this compelling conversation, Christopher reveals his "Future Career Toolkit" featuring practical tools for identifying your strengths and finding opportunities in emerging fields. Paul and Christopher explore how to leverage transferable skills, the importance of embracing technological chaos, and why you should apply for jobs even when you only have 60% of the listed requirements.
You'll Learn:
Why you should "chase the maelstrom" and seek out areas where business models are being transformed by new technologies
How Christopher transitioned from a professional musician to an IBM executive by recognizing transferable skills
The "Future Career Toolkit" 
Why you should apply for jobs even if you don't have all the requirements, especially in bleeding-edge tech
How to develop a workplace "persona" that helps you succeed in new environments
Why the upcoming AI agent revolution represents opportunities rather than threats
Practical strategies for connecting with industry leaders to find career opportunities
Subscribe to the Expert Intelligence podcast so you don't miss future conversations.

AI Literacy Starts with Play, Not Automation with Adam Hofmann

Adam Hofmann, leader of Elixirr's generative AI practice, joins Paul Estes to share insights on moving organizations from AI curiosity to implementation. Drawing from his journey from entrepreneur to AI strategy consultant, Adam reveals how shifting from technical experimentation to cultural engagement is key to successful AI adoption. Paul and Adam discuss the phenomenon of "present bias"—how our experiences with today's AI tools can limit our ability to envision their future potential.
From boardroom directives to CFO-led initiatives, this episode examines who's driving AI adoption and how companies can build momentum through targeted proof-of-concepts. Whether you're struggling with organizational alignment or looking for practical ways to start implementing AI, Adam's focus on playful experimentation offers a refreshing perspective on building AI literacy across your company.
You'll Learn:
How "present bias" limits our ability to see AI's exponential growth potential
Why CFOs and finance leaders are often surprising champions of AI adoption
The importance of identifying high-ROI use cases before diving into implementation
How to avoid the "internal cluster" problem when assigning AI ownership
Why making AI accessible and fun is crucial for organizational adoption
Simple ways to start building AI literacy by replacing everyday tasks
Creative approaches to AI experimentation, including Adam's music creation story
In This Episode:
Microsoft Copilot & Copilot Studio
Riffusion
ChatGPT
Claude
Azure AI Foundry
Service Now
Bolt.new
Cursor
Replit
 

The Case Against Rushing AI in School with Pip Sanderson

Pip Sanderson, from the National Institute of Teaching in England, brings a refreshingly balanced perspective from the front lines of AI and education. While many edtech enthusiasts rush to implement AI solutions, Pip challenges us to consider what's at stake in our pursuit of technological efficiency and how we might preserve the human essence of learning. In this thought-provoking conversation, Pip and Paul explore the real impacts of AI on students' cognitive development and the importance of preserving struggle in the learning process.
From the ethical considerations of AI-powered teaching tools to the critical importance of metacognitive skills, this episode offers a nuanced look at technology's role in education. Pip shares insights from recent research suggesting that while AI tools may improve short-term understanding, they potentially limit the development of higher-order thinking skills essential for long-term success. Parents and educators alike will find valuable guidance on navigating today's technology landscape with children's best interests at heart.
You'll Learn:
Why the push for "efficient learning" through AI might be undermining crucial cognitive development
How research shows AI tools may improve short-term understanding but limit higher-order thinking skills
The importance of preserving "desirable difficulty" and struggle in the learning process
Why boredom plays a crucial role in child development that technology often eliminates
How to evaluate the real benefits versus potential harms of AI in educational settings
The danger of schools adopting AI solutions without sufficient understanding of the technology
Practical advice for parents navigating technology decisions with their children
Mentioned in This Episode:
Cognitive Resonance
Books by Bernie Neville
"ChatGPT impacts student engagement from a systematic review and meta-analysis study" by Yuk Mui Elly Heung and Thomas K.F. Chiu
Subscribe to the Expert Intelligence podcast so you don't miss future conversations with industry leaders at the forefront of technological transformation. Each episode brings you practical insights to navigate our rapidly evolving digital landscape.

Zero-Admin Recruiting with Marcus Sawyerr

Marcus Sawyer, EQ app CEO and former Adecco Group X president, is building the AI recruiting revolution he predicted five years ago. In this eye-opening conversation with Paul Estes, Marcus reveals how AI is transforming hiring and Paul shares an experiment where AI ranked his friend's "best" resume dead last. If you're job hunting in 2025, you need these insider tips on getting past AI gatekeepers to land your dream role. From Marcus's "Zero Admin Revolution" mission to his practical OTT framework for implementing AI agents, learn how AI is transforming recruiting while keeping human relationships at the core of the recruiting process.You'll Learn:
How AI analyzes resumes differently than humans—and what this means for your job search
Why the "Zero Admin Revolution" is transforming recruiting (and how to benefit)
The simple "OTT" framework for understanding and implementing AI agents
Why finding the hiring manager is more crucial than ever in an AI-filtered world
How to distinguish between companies truly solving problems with AI versus those just chasing the next shiny tech tool
The critical first steps anyone can take today to get started with AI (hint: it begins with play!)
Marcus's powerful “10 Ps" planning framework for implementing AI effectively
Subscribe to the Expert Intelligence podcast so you don't miss future conversations with industry leaders at the forefront of technological transformation. Each episode brings you practical insights to navigate our rapidly evolving digital landscape.Producer: David GrabowskiTheme Music: Aleksey Chistilin

The Future of Creative Work in an AI-Powered World with Mark Heaps

Mark Heaps went from cutting out photos by hand to shaping AI’s future at Groq—and trust us, he’s got receipts. In this no-filter conversation with Paul Estes, Heaps drops the ultimate truth bomb: AI won’t replace humans, but humans who master AI will replace those who don’t. After a nail-biting story involving his son, a lionfish sting, and an LLM that saved the day, you’ll understand why this creative-turned-tech-exec is convinced we’re just scratching the surface of AI’s potential.
 
From building basketball team apps on the fly to transforming how we experience NBA games, Heaps breaks down the real-world applications revolutionizing how we live and work. He’s seen creative professionals move from eye-rolling dismissal to existential dread to genuine curiosity—all in 18 months. Get ready for a masterclass in why critical thinking will never go out of style, how latency issues are the real innovation bottleneck, and why your kids should be more worried about developing unique opinions than memorizing facts.
 
Connect with Mark on X and Instagram @lifebypixels
 
You’ll Learn:
How the “labor” parts of creative jobs are vanishing (and why that’s not terrible news)
The reason creative professionals have shifted from fear to fascination with AI
Why your R2-D2 and C-3PO moment is coming—and how to be Luke Skywalker in the scenario
The critical skills to future-proof yourself when AI can do almost everything else
How agentic workflows are creating thousand-bot debates that deliver better answers
What parents should tell their kids about navigating an AI-dominated future
Subscribe to the Expert Intelligence podcast so you don’t miss future conversations with industry leaders at the forefront of technological transformation. Each episode brings you practical insights to navigate our rapidly evolving digital landscape.
 
Producer: David GrabowskiTheme Music: Aleksey Chistilin

Collaboration in an Outcome-Based World: Insights from Tim Sanders

Collaboration is essential for the success of all businesses. Companies are more likely to succeed with a collaborative culture; therefore, business owners need to collaborate with talent to grow their company and preserve their resources. Gig models are a great way for businesses to work with freelancers and contractors without the hassle of finding and managing employees. They are also more cost-effective in the long run. Join this conversation with Tim Sanders and learn more about the future of an outcome-based world where entrepreneurs will only hire on demand. Learn more about the importance and types of collaboration. 
As a former Yahoo chief solutions officer and best-selling author, Tim Sanders is one of the top-rated leadership keynote speakers on the lecture circuit. His keynotes at conferences and corporate meetings offer actionable insights into leadership development, sales, collaboration, and corporate culture. He’s passionate about motivating audiences to move to action. Tim’s mission is twofold: lead professionals to deepen all their relationships through the generosity and expand their collaborative webs to solve their toughest challenges.
 
Tune in!
What You Will Learn:
[00:01] Quick bio of today’s guest, Tim Sanders
[01:06] What inspired Tim to write his book, Love is the Killer App
[05:50] Correlation between what you study and your income
[07:02] Common talk that Tim has heard from people off stage
[07:58] Why human service will be obsolete by 2050
[10:07] The one problem companies can solve through gig platforms
[13:42] Importance and types of collaboration in a company 
[16:08] Distributed collaboration
[18:49] Tim’s takeaway on collaboration
[21:37] Disruptive collaboration
[25:16] Protect and nurture your ideas
[28:38] The power of curiosity
[30:57] Damn collaboration
[33:22] The future of outcome-based world
[35:14] Working with a freelancer
 
Standout Quotes:
“Be a student, and when you learn something, become a teacher.” - Tim Sanders [02:43]
“There’s always a correlation between what you read and your income.”-Tim Sanders [05:50]
 “If you study Tony Robbins and what turned his life around, it was one year in an apartment in San Diego, where he literally read 500 books. If you study Mark Cuban’s life, his turnaround was two years when he read about 80 books a year to master his space.”- Tim Sanders [05:58]
“Millenials don’t think or care about talent. They care about delivering work.”- Tim Sanders [07:29]
“Gig economy is the future of doing business. For digital natives, that could be the only way to get the services you are looking for.”-Host [11:56]
“All innovations come from four distinct personalities.”-Tim [18:04]
“Big ideas show up as ugly babies, and it’s your job as a leader to protect them so that they eventually get cute.”-Tim [25:38]
“If you approach everything from curiosity… then you start to learn.”-Host [28:38]
Resources Mentioned
Tim’s Book, Love is the Killer App: https://www.amazon.com/Love-Killer-App-Business-Influence/dp/1400046831.
Rework by Jason Fried:  https://www.amazon.com/Rework-Jason-Fried/dp/0307463745
Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration by Ed Catmull: https://www.amazon.com/Creativity-Inc-Overcoming-Unseen-Inspiration/dp/0812993012
Competing in the Age of AI: Strategy and Leadership When Algorithms and Networks Run the World by Marco Iansiti: https://www.amazon.com/Competing-Age-AI-Leadership-Algorithms/dp/1633697622/.
 
Stay Connected
Tim Sanders
Website: https://timsanders.com/
Twitter: https://twitter.com/sanderssays
Facebook: https://www.facebook.com/SandersSays/
YouTube: https://www.youtube.com/user/gonzobiz/featured

Gigging the Gap: Navigating the Future of Workforce Shortages with Jason Radisson

Gigging the Gap: Navigating the Future of Workforce Shortages with Jason Radisson"
The gig economy, also known as the on-demand or freelance economy, is a rapidly growing sector of the global workforce. It is an economy that allows people to work independently in short-term, freelance jobs instead of traditional long-term employment. The gig economy is now seen as an effective solution to the global shortage of skilled front-line workers. By taking advantage of this new way of working, companies can access a larger pool of talented individuals willing to take on short-term projects or assignments, helping businesses fill their staffing gaps quickly and easily without going through the traditional hiring process.
 
Join this conversation with Jason Radisson as we discuss the advantages of using a gig economy in solving global workforce shortages and how it can benefit employers and employees. Jason Radisson is a serial unicorn breeder. His latest venture is Shift One, where he is the Founder & CEO, a platform that is helping solve the global shortage of skilled front-line workers, with more than 300,000 users, from nurses to solar technicians. Jason learned startup skills early in life.
 
Jason was born to a 16-year-old single mom and worked blue-collar jobs from short order cook to HVAC technician to fund school and climb out of poverty. From that inauspicious start, he went on to Harvard, a Fulbright Scholarship, and McKinsey & Company. Since becoming an entrepreneur, Jason has worked with more than a dozen first-tier VCs, firms like Softbank, Accel, DST, Andreessen Horowitz, Monashees, and Sequoia. Together he and his teams have built and scaled multiple tech unicorns, platforms that today provide work and improved living standards to millions of workers from Bogota to Boston.
 
Tune in!
What You Will Learn:
[00:34] Backstory of Jason Radisson
[02:24] How the gig economy will affect every industry
[03:24] Jason’s journey to technology and work
[06:55] His first experiences with doing work with automation
[11:43] How to balance the strengths and weaknesses of the gig economy
[15:20] What motivated Jason to become a founder
[17:19] Why Jason decided to operate his company in stealth mode
[18:40] The greatest challenge he has faced with customers
[21:38] What’s the future of Shift One company
[23:59] How Shift One helps in reshaping the old way of staffing
[27:19] Bringing a new ethical approach to blue-collar work
[29:39] Episode wrap-up and calls to action
 
Standout Quotes:
“Almost any job can be broken into smaller jobs that can be done on-demand.” - Jason [02:30]
“When people talk about the gig economy, there are two sides of the coin. Some people believe that it provides a good opportunity, while others believe that it takes advantage of workers.”-Host [11:08]
“There’s a problem with traditional staffing that technology and a new way of thinking can help solve.”- Host [23:37]
“One of the greatest challenges to navigate when outsourcing is to determine the fair price for the labor.”- Jason [28:10]
“A lot of people don’t understand that work is a choice in the gig economy.’-Host [28:48]
Stay Connected
Jason Radisson
Website: https://www.shiftone.net/
LinkedIn: https://www.linkedin.com/in/jason-radisson/
Twitter: https://mobile.twitter.com/jasonradisson