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. 

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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.

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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.

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Emergencies rarely give us time to prepare. Whether you are a military spouse, supporting aging parents, or simply planning ahead for your family’s peace of mind, being organized is not just smart. It is essential.
In this episode, Michael Cupps sits down with Donna Tellam, founder of GoBinders, to explore how small, consistent habits around organization can bring clarity and calm in life’s most chaotic moments. 
Donna shares the personal story that led her to create a simple system for keeping vital documents in one place, something that has made a life changing difference for families in times of crisis.
From natural disasters to deployments and elder care, you will learn how preparation can become a daily habit that supports the people you love.

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What does it take to feel more in control of your choices and routines? 

Whether you are looking to moderate or stop drinking, bring more intention into your day, or simply design habits that better reflect who you want to be.

In this episode, Cupps sits down with Jonathan Hunt-Glassman, CEO and founder of Oar Health, to talk about how thoughtful habit design can support long term personal change. 

Jonathan shares his own story of rethinking routines and building a system that helps people make confident and sustainable choices in everyday life.

They explore how structure, small wins, and accessible tools like medication can play a role in supporting change. If you are working toward better alignment between your drinking habits and your values, this episode offers practical ideas and encouraging insight.

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Ever reach the end of the day wondering where the time went?

In this episode of The Habit Architect, Michael Cupps and Reem Metawei dig into the hidden habits that quietly drain our focus like nonstop notifications, endless meetings, and mindless scrolling.

They reveal how these distractions sneak in, what they’re really costing us, and how to take back control with simple intentional shifts.

If you’re ready to stop feeling busy and start making real progress, this conversation is for you. 

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🎙️ On this episode of 𝘛𝘩𝘦 𝘏𝘢𝘣𝘪𝘵 𝘈𝘳𝘤𝘩𝘪𝘵𝘦𝘤𝘵, host Michael Cupps and co-host Reem Metawei are joined by business strategist and mentor Sophie Stardust to explore how intentional habits and simple systems can create space for sustainable success, with more clarity, calm, and joy.

Sophie works with creative entrepreneurs and business owners to design habits that align with their values, energy, and vision. 

She shares how she moved from a chaotic, fast-paced approach to a more intentional rhythm that supports both her business and overall well-being.

💡 This conversation dives into the difference between routines that truly serve you and those that just look good on paper. From reducing daily overwhelm to creating a lifestyle that supports how you want to work and live, this episode is filled with honest insights and actionable strategies.

✨ Bonus: Sophie takes us behind the scenes of her recent 1,000km autorickshaw adventure across India with 54 other female founders—raising over £140,000 (and counting) for women’s education, health, and empowerment.

🎧 In this episode: 

✅Designing habits that match your energy and values
✅ Building systems that bring clarity without complexity
✅ Releasing routines that no longer serve your growth
✅ Making space for ease, creativity, and joy
✅ Defining success on your own terms

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In this week's episode of The Habit Architect, host Michael Cupps welcomes Fiona Ross—known as the Queen of Kings—for a powerful conversation on habits, leadership, and identity. Fiona has built her reputation coaching high-performing male leaders to find clarity, confidence, and direction through intentional habit transformation.
From the boardroom to personal breakthroughs, Fiona helps C-suite executives and founders unlock their best selves by focusing on the routines that truly matter. In this episode, she dives into the emotional undercurrent of habits, how men can reshape their inner narrative, and why sustainable success always starts from within.
Whether you’re a leader seeking clarity or someone ready to break out of autopilot, this episode will give you a framework to create lasting change—one habit at a time.

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In this episode of The Habit Architect, host Michael Cupps sits down with Marin Varvodic to explore his remarkable journey from professional sports to tech entrepreneurship. 
They delve into the habits that fueled his successful transition, the role of resilience in facing unforeseen challenges, and how adaptability can lead to innovation. 
Marin shares practical strategies for cultivating a growth mindset and the importance of continuous learning in personal and professional development.

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What do fitness and habit-building have in common? Everything. 

In the latest episode of The Habit Architect, host Michael Cupps sits down with CrossFit coach Kevin Wood to uncover the key principles that drive both physical and mental strength.
Kevin shares how structured training mirrors the process of building discipline, resilience, and consistency in everyday life. 

From overcoming setbacks to developing a mindset of persistence, this conversation is packed with practical strategies for breaking through mental barriers and staying on track.

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