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. 

This Show is sponsored by TimeBandit.io

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.

This Show is sponsored by TimeBandit.io

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.

This Show is sponsored by TimeBandit.io

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.

This Show is sponsored by TimeBandit.io

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

Subscribe to our Newsletter: The Habit Architect Newsletter

In Part 1 of this special two-part finale, co-host Reem Metawei joins me to revisit the first 10 episodes that built the foundation for The Habit Architect.
These conversations shaped not just a podcast but a mindset.

We uncovered powerful truths about identity, discipline, resilience, and how intentional habits shape the way we lead and live.

We heard how Brandon Lee treats digital presence like a daily credibility practice.

Russ West and Danielle W. shared how check-in rituals strengthen connection before conflict ever begins.

Nandan Mullakara showed how automation can serve not replace human focus.

And in raw, honest conversations, Tabby Kerwin (MAPP), Emily Ackerman, and Julie Jones unpacked grief, balance, and how presence is something you train, not hope for.

Kevin Wood reminded us that discipline isn’t loud, it’s consistent.

Marin Varvodic closed the chapter by connecting athletic grit to executive leadership.

If you’re new to the show or looking to reconnect with what matters, this episode is your pause, a chance to reflect, reset, and remember: it all starts with one intentional habit.

This Show is sponsored by TimeBandit.io

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

Subscribe to our Newsletter: The Habit Architect Newsletter

In this special episode recorded from the French coast, Michael Cupps shares reflections on the first season of The Habit Architect and previews what’s ahead.

With two recap episodes coming soon, joined by Reem Metawei to unpack the top insights from 19 powerful conversations, this episode is a short solo moment to reconnect.

Michael also shares a personal lesson: how trading up your time, letting go of what’s good for what’s great, is the key to growth. 

Through habits and priorities, you can transform your time into something that serves your values.

Tune in for a thoughtful pause and a look at what’s next. 

This Show is sponsored by TimeBandit.io

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

Subscribe to our Newsletter: The Habit Architect Newsletter

In this powerful and practical episode, host Michael Cupps sits down with Cathy Minter, Co-Founder and CEO of Wisdom.io, to explore how intentional habits and respectful technology can support older adults as they age with confidence in the homes they love.

Cathy shares the heart behind Wisdom.io | an innovative, privacy-first smart system that detects routine changes, supports caregivers, and helps families stay connected without creating stress or intrusion.

But this conversation goes far beyond the tech. It dives deep into the daily habits and design principles that preserve dignity, autonomy, and peace of mind as we grow older.

Whether you're a caregiver, a technologist, or simply someone thinking about the future of aging, Cathy’s insights offer a fresh, human-centered perspective.

This Show is sponsored by TimeBandit.io

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

Subscribe to our Newsletter: The Habit Architect Newsletter

What separates high-growth tech companies from those stuck in stagnant lead funnels? It’s not just tools. It’s not just talent. It’s habits, the daily, intentional actions that compound into sustainable demand.
In this episode, Michael Cupps is joined by Shannon Prager, President of Leadit Marketing. Shannon helps tech companies with complex offerings untangle their go-to-market chaos and rebuild around clarity, alignment, and strategic focus. Together, they unpack how AI is forcing a new level of discipline in demand generation and why leaders must shift from campaign thinking to system thinking to thrive.
This is a masterclass in scaling demand the right way, one habit at a time. 

This Show is sponsored by TimeBandit.io

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

Subscribe to our Newsletter: The Habit Architect Newsletter

Behind every stalled transformation is a system without structure or habits without reinforcement. 

In this episode, Michael Cupps is joined by Tony Castelli, Executive Vice President at Rulesware and former Pega, Accenture, and IBM leader, to explore how successful enterprise transformation depends not only on strategy, but on disciplined execution.
Tony brings decades of experience guiding enterprise organizations through AI adoption, business process redesign, and operational change. He shares hard-earned lessons on what makes transformation stick, starting with a well-designed system, and continuing with the habits that reinforce it every single day.
This episode is a playbook for leaders ready to break the cycle of initiative fatigue and build something sustainable.

This Show is sponsored by TimeBandit.io

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

Subscribe to our Newsletter: The Habit Architect Newsletter

In this insightful episode of The Habit Architect, host Michael Cupps is joined by Dr. Jennifer Churchill, a management psychologist, high-performance executive coach, and Certified Hormone Health Coach. Together, they confront a growing and often ignored crisis: the quiet exit of high-potential women from the workforce during midlife.
Dr. Churchill shares her deep expertise on the intersection of hormonal health, identity, and leadership performance — revealing why so many accomplished women begin to feel disconnected, depleted, and doubtful during a stage of life that should be defined by strength and wisdom.
With her Feminine Genius Method, she outlines a path toward restored vitality, confidence, and sustainable leadership for women navigating perimenopause and beyond.
This episode is a must-listen for women leaders, executives, and organizations ready to better support the unique journey of midlife female leadership.

This Show is sponsored by TimeBandit.io

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

Subscribe to our Newsletter: The Habit Architect Newsletter