In this episode of The CTO Show with Mehmet, we dive into the future of management with Jack Skeels, CEO of Agency Agile and author of Unmanaged. Jack shares why traditional command-and-control structures are outdated, how hidden dysfunctions cripple organizations, and what it takes to unlock true productivity in the age of AI.

We explore why overmanagement is slowing teams down, the warning signs leaders should watch for, and how AI can either reinforce bad habits—or transform organizations when paired with agile, human-centric practices.

Key Takeaways

• Why most management practices are outdated—and what to do instead

• The “plateau of optimism” and “chasm of despair” in projects and transformations

• How to spot hidden dysfunctions that derail productivity

• Why AI won’t fix bad processes—and how to redesign work for real impact

• The power of asking why and questioning the status quo

What You’ll Learn

• How to move from bureaucracy to agility in your organization

• Practical techniques to boost productivity and reduce rework

• Why unleashing talent beats overmanaging

• How AI is reshaping teams, value chains, and leadership roles

About Jack Skeels

Jack is the founder and CEO of Agency Agile, where he has worked with nearly 200 organizations to help them run faster, better, and happier. With a career spanning programming, project management, consultancy, and research at the RAND Corporation, Jack brings a unique perspective to modern leadership. His award-winning book Unmanaged offers a blueprint for rethinking how teams thrive.

https://www.amazon.com/Unmanaged-Master-Creating-Empowered-Organizations/dp/B0CLSJJJ49

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

Episode Highlights

• [02:00] Jack’s journey from programmer to RAND researcher to Agency Agile founder

• [07:00] Why outdated management persists and the role of education in leadership

• [12:00] Warning signs of overmanagement and how to measure real productivity

• [18:00] Why CEO buy-in is non-negotiable for transformation

• [20:00] The “plateau of optimism” and “chasm of despair” in projects

• [24:00] How AI changes management—and why undoing structures is key

• [31:00] Trust and manipulation in AI decision-making

• [37:00] Jack’s book Unmanaged and its core lessons

• [40:00] Advice for the new generation of leaders: think different and always ask why

In this episode of The CTO Show with Mehmet, Angela Thomas shares her extraordinary journey from growing up in East Germany to building award-winning businesses, reinventing her career, and now helping entrepreneurs scale in Dubai.

We dive into the misconceptions about scaling, the role of authenticity, why reinvention is critical, and why Dubai has become a global hub for entrepreneurs.

Key Takeaways

• Why authenticity is a non-negotiable asset when scaling a business

• The difference between scalable and non-scalable models (time vs. value detachment)

• How value ladders unlock sustainable growth

• Why founders must invest in their own development before their businesses can grow

• Dubai’s rise as the “Disneyland for entrepreneurs”

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What You’ll Learn

• How to reinvent yourself without abandoning your past achievements

• Strategies to avoid stagnation and overcome plateaus

• The importance of lead magnets, trust-building, and tiny challenges in client acquisition

• Why moving to Dubai offers unique opportunities for global founders

About Angela Thomas

Angela Thomas is the founder of Angel Success Consulting, a Dubai-based entrepreneurial family office that helps founders, doctors, and service providers scale sustainably and internationally. With nearly 30 years as a serial entrepreneur, Angela has built and sold businesses across industries – from retail and real estate to aviation, healthcare, and luxury.

Today, she is known as Europe’s #1 Scaling Expert and the visionary behind high-impact programs like Skillionair, Skillionize, and Dubai Docs Fast Track – a relocation success model for physicians entering the UAE market.

https://www.angelsuccess.consulting/

https://www.linkedin.com/in/angela-thomas8/

Episode Highlights

• [00:02:00] Angela’s entrepreneurial roots in East Germany

• [00:07:00] Reinvention and overcoming the fear of leaving success behind

• [00:13:00] Why authenticity matters more than ever in business

• [00:16:00] Business doesn’t grow unless the founder does

• [00:21:00] Scalable vs. non-scalable business models

• [00:26:00] The process Angela uses to help founders find growth

• [00:33:00] Why she calls her boutique setup a “Family Office 2.0”

• [00:36:00] Dubai as the Disneyland for entrepreneurs

In this episode of The CTO Show with Mehmet, I sit down with Rob Matzkin, a serial entrepreneur, investor, and connector who has built and exited multiple companies and now advises startups on scaling, fundraising, and execution.

Rob shares the hard truths of entrepreneurship — why execution beats hype every time, what founders get wrong about investor readiness, and how AI is reshaping startup moats. We also dive into founder burnout, the myth of overnight success, and the importance of building authentic relationships.

Key Takeaways

• Why most founders are not actually investor-ready

• How to show traction and de-risk your pitch to investors

• The double-edged sword of AI in fundraising and positioning

• Why execution > ideas (and how to prove it)

• How to avoid burnout and build a sustainable founder journey

What You’ll Learn

• The stages of fundraising explained clearly (friends & family, pre-seed, seed, Series A)

• The signals investors actually look for — beyond hype and storytelling

• How startups can think about moats in the age of AI

• The role of vulnerability and authenticity in leadership

About Rob Matzkin

Rob has founded and led 16 different companies, with multiple exits across sectors. Today, he consults founders on reaching product–market fit, scaling to millions in ARR, and navigating capital raising. He is also the host of the Purpose-Driven Summit and a recognized global connector across business, sports, and the arts.

https://robmatzkin.com/

https://www.linkedin.com/in/rob-j-matzkin-06027634/

Episode Highlights

• (00:04:50) Why founders think they’re unique (but they’re not)

• (00:09:30) The truth about being “investor-ready”

• (00:14:00) Risk vs reward: how investors really decide

• (00:22:00) AI hype vs real AI companies — what matters now

• (00:30:00) Product–market fit and why most founders misunderstand it

• (00:33:30) Burnout, balance, and the myth of working 16-hour days

• (00:44:30) Why most public stories about success are PR illusions