The Habit Architect

 Why do AI projects fail when the tech works? 

Michael Cupps and returning guest Tony Castelli, PhD (Rulesware; ex-Accenture, IBM, Pegasystems) explain how change management, trust, and team habits determine AI adoption. We cover shadow resistance, the role of middle management, and simple ways to move from AI drafting content to assisting real decisions. Practical takeaways: continuous learning, smart experimentation, and a people-first AI strategy you can actually run. 

The Habit Architect is sponsored by Enterprise Diagnostics and Time Bandit

Check out our Live Show Events here: The Habit Architect Live Show

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We all say we’ll start tomorrow. But what keeps us from following through?

In this episode, Michael Cupps and Florencia Llosas explore why habits don’t stick—even when we want them to. From finite time blindness to emotional burnout, they unpack what’s really holding you back and how to reset.

You’ll learn:

• Why awareness isn’t enough
• How emotions derail routines
• Simple ways to build habits that last

Start now, not someday.

The Habit Architect is sponsored by Enterprise Diagnostics and Time Bandit

Check out our Live Show Events here: The Habit Architect Live Show

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Michael Cupps is joined by Ivana Brutenic and Kristina kováčiková from SUNDAYFLIES, a sister-led consultancy helping people and companies show up authentically on LinkedIn. 

Learn how to turn content creation, comments, and storytelling into simple daily habits that build real engagement and trust—without spamming your feed. 

The Habit Architect is sponsored by Enterprise Diagnostics and Time Bandit

Check out our Live Show Events here: The Habit Architect Live Show

Subscribe to our Newsletter: The Habit Architect Newsletter

Is your benefits package really supporting your life—or just checking a box?

In this episode, host Michael Cupps welcomes Jordan Peace, CEO of Fringe, to explore how companies can rethink employee benefits to meet real, everyday needs. From flexible perks and retention to mental health and neurodiverse leadership, Jordan shares his personal journey with ADHD, fatherhood, and building a business with heart.

You’ll learn:

• Why work-life flexibility matters more than balance
• What employers often miss when designing benefit programs
• How ADHD shaped Jordan’s leadership and systems
• Practical ways to support mental health at work
• How modern benefits impact recruiting and retention

Perfect for founders, HR leaders, and anyone rethinking the future of work.

The Habit Architect is sponsored by Enterprise Diagnostics and Time Bandit

Check out our Live Show Events here: The Habit Architect Live Show

Subscribe to our Newsletter: The Habit Architect Newsletter

 If your habits are inconsistent and your energy constantly dips, the issue might not be your willpower. it might be your nutrition. 

In this episode of The Habit Architect, Michael Cupps speaks with registered dietitian Marissa Dankosky from Foodsmart about how food choices impact focus, consistency, and long-term habit formation. 

They explore the real reasons it’s hard to stick to healthy routines—and why your favorite FoodTok advice might be making it harder, not easier. 

This isn’t a conversation about diets or discipline. It’s about realistic, sustainable shifts that support your goals, especially when burnout, travel, or a busy schedule get in the way. 

If you care about performance, wellness, or building better habits, this is your sign to start HERE. 

The Habit Architect is sponsored by Enterprise Diagnostics and Time Bandit

Check out our Live Show Events here: The Habit Architect Live Show

Subscribe to our Newsletter: The Habit Architect Newsletter

Can 10 minutes of focused learning change how you lead and grow? In this episode, Michael Cupps talks with Ana Mashchuk of Headway Inc to explore how micro-learning helps busy professionals build better habits, sharpen leadership skills, and boost team performance.

What you’ll learn:
 ✔️ What micro-learning looks like in real life
 ✔️ How top teams use it to build stronger culture
 ✔️ Tips to start a 10-minute learning habit

Listen in and make learning part of your daily rhythm.

The Habit Architect is sponsored by Enterprise Diagnostics and Time Bandit

Check out our Live Show Events here: The Habit Architect Live Show

Subscribe to our Newsletter: The Habit Architect Newsletter

Employee benefits can feel confusing, expensive, and full of fine print, especially in the U.S. healthcare system.

In this episode of The Habit Architect, host Michael Cupps speaks with Kristan Carlton, a Tulsa-based expert in group health benefits and employee coverage strategies. As VP of Operations at Inspire Benefit Consultants, Kristan shares what employees and HR leaders need to know to navigate medical plans, dental and vision options, mental health support, and voluntary benefits like accident insurance.

What you’ll learn:

• How to pick a health insurance plan that fits your actual needs
• Why accident insurance is gaining popularity in U.S. companies
• Common mistakes employees make during open enrollment
• What HR teams can do to offer better benefit education
• Real talk on EAPs, remote worker support, and rising healthcare costs

Whether you’re a small business owner in Oklahoma, an HR leader managing multiple states, or just trying to make sense of your medical benefits, this episode offers simple, practical advice.

🎧 Listen now and learn how to make smarter benefit decisions for yourself or your team. 

The Habit Architect is sponsored by Enterprise Diagnostics and Time Bandit

Check out our Live Show Events here: The Habit Architect Live Show

Subscribe to our Newsletter: The Habit Architect Newsletter

In this episode of The Habit Architect, Michael Cupps sits down with Benj Miller, co-founder of System & Soul and a leadership coach who helps companies align people, processes, and purpose. Together, they unpack why so many business meetings become time-wasters, how company culture shows up in the way meetings are run, and what leaders can do to make every meeting count.

You’ll discover how:

• Business growth creates complexity that clutters calendars and stalls progress
• Meetings can reveal deep truths about leadership style and team alignment
• A single habit shift can transform meetings into engines of clarity, decision-making, and action

Whether you’re a CEO, team leader, or entrepreneur, this conversation will help you stop time-wasting meetings and start running ones that actually move your business forward.

Because the goal isn’t fewer meetings. It’s meaningful meetings.

The Habit Architect is sponsored by Enterprise Diagnostics and Time Bandit

Check out our Live Show Events here: The Habit Architect Live Show

Subscribe to our Newsletter: The Habit Architect Newsletter

In the Season 2 premiere of The Habit Architect, host Michael Cupps sits down with Andrew Olowu, CTO of Axxess, to explore the habits, mindset, and personal journey behind his remarkable career.

Born and raised in Nigeria, Andrew shares how an early curiosity about computers led him to the U.S., where he steadily built a path from student to global tech leader. This episode goes beyond career milestones to unpack the quiet discipline and intentional routines that helped him overcome imposter syndrome, navigate cultural change, and lead with purpose.

From growing companies across continents to raising children with intention, Andrew offers grounded wisdom for anyone pursuing meaningful growth, both personally and professionally.

The Habit Architect is sponsored by Enterprise Diagnostics and Time Bandit

Check out our Live Show Events here: The Habit Architect Live Show

Subscribe to our Newsletter: The Habit Architect Newsletter

In this Season 1 finale of The Habit Architect, host Michael Cupps and co-host Reem Metawei return for Part 2 of our reflection, revisiting Episodes 11 through 19.

These conversations went beyond productivity and into the habits that carry us through real-life transformation: recovery, reinvention, caregiving, and confident aging.

Fiona Ross challenged long-held leadership scripts and asked us to upgrade the “operating systems” we live by.

Sophie Stardust reframed structure as a form of freedom, while Jonathan Hunt-Glassman showed how disrupting one small habit can reset your life.
Donna Tellam and Dr. Jennifer Churchill, MBA, PhD opened up about preparing for life’s hardest moments, whether it’s a health crisis or a midlife shift.
Tony Castelli and Shannon Prager offered insights on building habits inside organizations that stick, not just scale.
And Cathy Minter reminded us that good design and good routines preserve dignity as we age.
This isn’t just a recap. It’s a close to a season that asked: What are you repeating daily? And is it shaping the life you actually want?
Tune in to reflect, reset, and carry the habits forward.

The Habit Architect is sponsored by Enterprise Diagnostics and Time Bandit

Check out our Live Show Events here: The Habit Architect Live Show

Subscribe to our Newsletter: The Habit Architect Newsletter