The Habit Architect

Habits rarely fall apart because people do not care. More often, they break down in the space between intention and interruption where doubt gets louder, momentum fades, and progress starts feeling harder than it did at the beginning. In this episode of The Habit Architect , host Michael Cupps talks with Jennifer Pinter , a customer success strategist who works with seed to Series A SaaS founders,...

 Most healthcare AI conversations focus on automation. But the real opportunity is something more human: restoring presence. In this episode of The Habit Architect , host Michael Cupps sits down with Calvin Carter (CEO of Maddick and founder of Bottle Rocket) to unpack how technology can either create friction or remove it. They start with the everyday ways brands overwhelm customers with pop-ups,...

GLP-1 medications didn’t start as a cultural headline but they’ve become one because they’re changing real lives. The problem is: access hasn’t been equal, the market is still noisy, and most people don’t realize the medicine is only part of the story.  In this episode of The Habit Architect , host Michael Cupps talks with Chris Beers, founder of OrderlyMeds, about how telemedicine and compounded...

Quitting isn’t the problem,  building habits on the wrong setup is. By mid-January, most resolutions collapse not because people are lazy, but because they picked habits that don’t fit their environment, schedule, or identity. In this episode of The Habit Architect , host Michael Cupps is joined by returning guest co-host Flor (calling in from Argentina) to break down “Quitter’s Day” the point in...

Great creative work rarely fails because people aren’t talented, it fails because the system around the talent is chaotic. When files live in five places, naming conventions change by person, and teammates can’t find what they need, creativity turns into rework, delays, and frustration. In this episode of The Habit Architect , host Michael Cupps sits down with Jessica Story, CEO and co-founder of...

Most people think “community” is something you scale with software. But the best communities are built with habits you can’t automate. Showing up, remembering details, making thoughtful introductions, and creating spaces where people feel seen. In this episode of The Habit Architect , host Michael Cupps talks with Leslie Greenwood, founder of Wednesday Women , about the unscalable practices that m...

Most sales professionals don’t realize how quickly “a drink after work” turns into a default coping strategy. Not because they’re weak, but because the culture trains them: celebrate the win with a drink, survive the loss with a drink, travel for work with a drink, network with a drink. Eventually, the cue becomes automatic and the habit starts driving the day. In this episode of The Habit Archite...

Marketing doesn’t usually fail because people aren’t working hard. It fails because the questions are scattered, the data is fragmented, and decisions get delayed while someone downloads spreadsheets, cleans numbers, and tries to tell a clear story. In this episode of The Habit Architect , host Michael Cupps talks with Jill Randall , COO and co-founder of Fuse , about building the habit of better...

Most people confuse task management with life design. By mid-February, most New Year resolutions have failed. Not because people lack discipline, but because they built habits on the wrong foundation. In this solo episode, host Michael Cupps explains the difference between a task list and a values-based blueprint. Drawing from the Time Bandit priority management methodology, he demonstrates how to...

Sustainability is not an initiative you bolt on. It is the ultimate time management question: what you do today either builds a resilient business or kicks debt to the next quarter, the next leader, or the next generation. In this conversation, host Michael Cupps talks with William Pleasant , Chief Solutions Officer at Bridge House Advisors , who helps companies turn sustainability from compliance...

How do you decide what matters most when everything feels urgent? In this episode, producer Florencia Llosas flips the script and interviews host Michael Cupps about the foundation of effective habit building: your personal hierarchy of values. Michael explains why most people fail at building habits because they skip the critical first step of defining their values. Not political talking points,...

For those of you who can't believe it's almost Christmas already, let's go back to the end of October with this episode. AI promises to make life easier, but what happens when these tools actually hijack our habits instead? In this conversation, host Michael Cupps talks with Cortnie Abercrombie , author of "What You Don't Know" and founder of AITruth.org They discuss...

Michael Cupps sits down with Rachel Shaw, CEO of Shaw HR, to explore creating inclusive workplaces for employees with disabilities. Rachel shares her journey from handling ADA compliance to building a career helping organizations move beyond checkbox compliance toward human-centric decision making. Learn why diverse workforces are 20% more profitable, the critical difference between starting with...

What happens when your values collide with real-life financial pressure? Brent Hines , founder of the Foundation for Financial Wellness, joins Michael Cupps to explore how behavioral habits (not just income) shape long-term financial health. Learn how to build financial habits rooted in purpose, stop the comparison trap, and make money decisions with clarity, not chaos. A must-listen for anyone fe...

 What does it really take to stick with fitness?  In this episode, Michael Cupps sits down with Coach Junior to talk about the mindset behind lasting fitness habits. From showing up sore to staying consistent when motivation fades, this conversation goes beyond reps and routines.  You’ll learn how coaching creates accountability, why small steps matter more than perfect plans, and what keeps peopl...

 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,...

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 la...

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 Ban...

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...

 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 rout...

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 star...

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 n...

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...

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 mile...

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...