The Habit Architect

Michael Cupps
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Hosted by Michael Cupps, The Habit Architect is designed to help you intentionally build the habits that lead to success and break free from those that hold you back.  Each episode, Michael guides you through practical strategies for designing focused, productive days that align with your goals and vision. Whether you’re striving for personal growth or professional success, this show will help you create the daily routines and mindset shifts needed to unlock your full potential.  Tune in for expert insights, actionable steps, and real-life examples to transform your habits and build the life you desire—one intentional habit at a time.

  1. 2D AGO

    THA S02 EP#33 - What a Health Crisis Can Teach About Values

    Most people hear a story about someone who built a company, scaled it to 1.5 trillion in assets under management, and sold it to State Street, and they think that's the whole story. It isn't. In this episode, Michael Cupps sits down with Haresh Patel, entrepreneur, author, and founder of Senari Health, to talk about what was running underneath all of that success for over a decade. Haresh was living with a chronic skin autoimmune disease called urticaria, misdiagnosed by 12 doctors over 12 years, managing it with a $3,000 shot every four weeks, and never once being asked the question that eventually changed everything. That question came from an Ayurvedic doctor in Costa Rica, and it wasn't "Are you stressed now?" It was "When's the first time in your life you were stressed?" The answer took Haresh back to age six, to a car accident in Colorado, and to a grief he had carried for 55 years without ever naming it. What followed was unexpected, unconventional, and, three and a half years later, he has not needed the shot since. Haresh connects that journey directly to the company he built afterward. The same fragmentation problem he solved in private markets at Mercatus turned out to be the exact problem in healthcare. Your data exists. Your story exists. Nobody is putting it together. Senari Health is his attempt to fix that. Michael and Haresh cover the 13.5-minute doctor visit problem, why modern medicine takes snapshots instead of reading a movie, what it actually means to be the CEO of your own health, and why opening multiple doors at the same time is better than going through them one at a time. Haresh's book, The Ghost in Your Body, is available now on Kindle. The physical copy releases May 13th. Connect with Haresh Patel hareshpatel.ai haresh@senarihealth.ai senarihealth.ai Early adopter access for the Senari Health platform is available for the first 100 listeners who reach out directly. 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

    32 min

  2. MAY 8

    THA S02 EP#32 - Diagnose Before You Lead: What Makes a CEO Worth Following

    Michael Cupps sits down with Chantelle Preston, healthcare entrepreneur, investor, growth strategist, and co-owner of a League One volleyball expansion team launching in San Francisco in 2027. Chantelle built Mentis Neurorehabilitation from the ground up and exited to private equity in 2015. What she found at the finish line surprised her. Not fulfillment. Not arrival. Just the quiet question of whether she had been chasing the right things all along. That question became a book. The Success Lie breaks down nine narratives most leaders absorbed early in life. You can have it all. Say yes to everything. Someone will take care of you financially. It is too late. Chantelle and Michael work through several of them in this conversation, including the one that catches experienced leaders off guard: the habit of serving goals you set years ago that no longer reflect who you are or where you want to go. They get into work-life integration (not balance, Chantelle is clear on the distinction), the cost of perfectionism waiting until something is 120% ready before moving, why feedback and failure are data points rather than verdicts, and how culture does not live in a values statement on the wall. It lives in micro decisions made daily at every level of the organization. Chantelle also shares the one non-negotiable habit she puts on her calendar every week and never cancels. Connect with Chantelle Preston LinkedIn: linkedin.com/in/chantellepreston Website: chantalpreston.com Advisory: prestonpartners.net Book: The Success Lie, available for pre-order now, launches July 28th on Amazon and Barnes & Noble 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

    34 min

  3. MAY 4

    THA S02 EP#31 - Bold Plans Don't Build Themselves: The Execution Gap

    Most leadership teams are pretty good at the big idea. They get in a room, whiteboard it, agree it's the right move, and then hand it off. What happens after that hand-off is where organizations quietly lose. Leslie Holman has spent 15 years studying exactly that space. As the leader of Pinnacle Performance Group in Minneapolis, she works with companies ranging from $10 million to Fortune 100 on what she calls strategic execution: everything that lives between the bold plan and the moment John on the front line finally understands what's being asked of him. She came up through McKinsey, got her footing in quick-service restaurants where clarity in operations isn't optional when the stakes are a consistent hamburger or a food safety incident, and has brought that same precision into some of the most complex organizational transformations across industries. In this episode, she and Michael dig into why great ideas die, how to diagnose your organization's capacity for change before you add one more initiative, and what it actually looks like to lead with humanity when the world outside the office starts bleeding through. Leslie's take on the execution gap is practical and direct. Clarity, focus, and tenacity. Not motivation. Not culture decks. Not a project management tool. Those three things, built into the rhythm of how a team operates, are what separate organizations that get things done from the ones still talking about the plan they made two quarters ago. They also get into AI adoption, what honest leadership looks like when the workforce is genuinely scared, and why Leslie's firm has a rule: they don't work with jerks. If you are leading a team through any kind of change, building a habit around execution, or just trying to understand why your good ideas keep stalling out, this one is for you. 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

    36 min

  4. APR 27

    THA S02 EP#30 - Showing Up Where the Search Happened: Building for the New Search Reality

    For more than 20 years, marketing teams built an entire discipline around getting found on Google. Keywords, backlinks, content calendars, ad spend strategies, all of it engineered around one outcome: rank on page one. That system did not disappear, but it got a new set of rules on top of it, and most teams have not caught up yet. In this episode, Michael Cupps sits down with Arnold Huffman, CEO of Yalo, an Atlanta-based digital agency he founded 14 years ago as a one-man operation. Huff and Cupps have worked together before and that history shows in the conversation. They get to the point fast. Huff walks through what has shifted in search, how ChatGPT and Gemini are now processing 2.5 billion searches a day between them, representing roughly half of all internet searches, and why that number is expected to more than double by 2028. The old SEO habits still matter, but they are no longer enough on their own. Today's AI engines reward brands that are clear, easy to navigate, and talked about positively in places beyond their own website. Reddit threads, Facebook reviews, third-party comments, all of it feeds the engine's sense of whether a brand deserves to be cited. Huff calls the standard he applies to every site the "Boomer filter." If your mom cannot find what she is looking for on your website, the AI engine is not going to like it either. Cupps immediately renamed it the Linda Cups filter. That kind of clarity and that is the real point of the conversation. The brands that will get cited and recommended are the ones that sound like people, not landing pages. They also talk about what AI-generated content does to your credibility with AI engines. The short version: the engines know, and they will not give you the same weight they give to content that reads like a real person wrote it with a real point of view. On the personal side, Huff shares what keeps him grounded. He still runs and plays basketball five to seven days a week, something he traces back to identifying as an athlete since his college sports days. He also talks about a company habit worth noting: Yalo gives every employee an annual concert stipend, backed by research suggesting that people who attend live music regularly tend to be happier and live longer. His son and he are heading to Cleveland to see the Foo Fighters in August. Cupps closes with a question about what happens when AI changes a personal daily habit too, and Huff's answer on how to challenge the engine rather than just accept the first answer it gives you is one of the better practical notes in the episode. If your team has been putting off a website review or assuming your content calendar is doing the work on its own, this one is worth the 35 minutes. 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

    35 min

  5. APR 17

    THA S02 EP#29 - Stop Leading on Fumes: The Habit of Regenerative Leadership

    Allie Stark has built two things at the same time: a boutique executive coaching practice focused on female founders, and Noria, a leadership and development platform that helps teams shift how they work, lead, and grow together. She just turned 40, has a 14-month-old at home, and holds a master's degree in integrative health. Her path to this work started at 15 and has not slowed down since. In this episode, Michael Cupps sits down with Allie to talk about a term she uses that most leaders have not slowed down long enough to consider: regenerative leadership. Not a rebrand of work-life balance, which Allie addresses directly and dismisses just as quickly. What she means is building cultures and habits that rebuild the people inside them rather than extract from them. A cyclical model rather than a linear, upward-at-all-costs one. The conversation traces how most leaders got here. The hustle that gets applauded. The all-nighters that become talking points. Allie shares a story from a client about a preschool sign that read "Shaping the leaders of the future," and uses it to lay out how early and how deeply the achievement-at-all-costs mindset gets installed. Michael adds his own: a cancer diagnosis that made him rethink the relationships he was carrying and how he was carrying them. They also get into what burnout actually is. Not a condition a long weekend fixes, but a signal that something is off at the root. Allie works with leadership teams across organizations of all sizes and with individuals who are exhausted in ways most people around them cannot see. The habits section is specific. Allie is not describing a three-hour morning routine. She is talking about five minutes of meditation done consistently, morning pages journaling, walking without a phone, and building in silence wherever it fits. Her point: silence is where the information lives. Michael echoes it from his own daily walk practice. The episode closes with a practical tip that landed in real time with listeners in the comments: if a hard conversation is coming, take it on a walk. Shoulder to shoulder, moving in the same direction. The dynamic shifts in ways that sitting across from someone simply does not allow. 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

    35 min

  6. APR 6

    THA S02 EP#28 - Stop Guessing, Start Mapping: The Science of People Strategy

    Most leaders think they know their people. Jason Taylor says the data tells a different story. Jason is the President of JET Coaching Co. and Managing Principal at Predictive Success Corporation. His work is built around one question: do you actually have the right person in the right role? Not who you think is right for it. Not who has seniority. The person whose behavioral makeup fits what the job actually demands. In this conversation, we get into the science behind the Predictive Index, what really drives misalignment on teams, and why the best salesperson on your team is probably not your next sales manager. We also talk about self-awareness. Jason shares a stat from a Harvard researcher that stopped me cold: 95% of people believe they are self-aware. Only 15% actually are. That gap is where most leadership problems live. Topics covered in this episode: why promoting your best performer is often the wrong move, the four behavioral factors the Predictive Index measures, how to map your team so you stop guessing, what true self-awareness looks like in practice, the four types of team members every leader has right now, why growth does not always mean a promotion, and what Jason calls better work, better world. Connect with Jason Taylor: LinkedIn: linkedin.com/in/jason-taylor Email: jtaylor@predictivesuccess.com 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

    35 min

  7. MAR 27

    THA S02 EP#27 - The Habit of Resilience: Build It Before You Need It

    Resilience does not usually get built when life is easy. It gets built in the moments that force us to slow down, rethink what matters, and decide whether we are going to stay stuck in what happened or grow into what comes next. In this episode of The Habit Architect, host Michael Cupps talks with Stacey Copas, founder of the Academy of Resilience and author of How to Be Resilient, about what resilience really means and why so many people misunderstand it. Stacey explains that resilience is not just about coping, surviving, or “bouncing back.” For her, resilience is the opportunity to grow through a challenge, not simply get through it. She also makes the case that resilience is mostly proactive built through the habits, mindset, and capacity we create before life forces us to use it.  Stacey shares how that perspective was shaped by her own life-changing injury at age eleven, when a devastating accident completely altered the path she thought her life would take. What followed was not a quick comeback story, but a long process of reframing pain, rebuilding identity, and eventually discovering a calling in helping others navigate adversity with more honesty and intention. That experience now shapes the work she does with founders, leaders, and business owners who are often carrying pressure in silence, trying to keep moving while feeling overwhelmed, isolated, or close to breaking point.  Michael and Stacey also explore how resilience applies inside organizations, especially during uncertainty, change, and disruption. They talk about why resilience cannot be reduced to a one-time workshop or a wellness perk, why leaders need to communicate reality without feeding panic, and how the best response to uncertainty is often to focus on what is still within your control. Later in the episode, Stacey shares her perspective on AI, job uncertainty, and the importance of helping people shift from fear to curiosity asking not only what might be lost, but what new possibilities might be opening up.  This episode is for founders carrying more pressure than they admit, leaders trying to guide teams through uncertain seasons, and anyone who wants a more grounded understanding of resilience than the usual slogans. It is a thoughtful conversation about adversity, leadership, perspective, and the habits that help people build strength before life demands it. 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

    38 min

  8. MAR 18

    THA S02 EP#26 - Get Curious Instead of Furious: What hard conversations can build

    Long-term relationships do not usually break down because one conversation goes badly. They break down when tension gets buried, resentment builds quietly, and people stop returning to the hard conversations that could have created more understanding, trust, and connection. In this episode of The Habit Architect, host Michael Cupps sits down with Russ and Danielle West of Intentional Marriages to talk about the habits that help relationships last. Drawing from decades in corporate sales, years of counseling, and their work mentoring hundreds of couples, Russ and Danielle explain why conflict is not the real problem. The bigger issue is what happens after the tension shows up. Do we shut down, push harder, walk away for good, or learn how to pause, come back, and repair?  They unpack the nervous-system side of conflict, including how people get emotionally flooded and tend to respond with fight, flight, or freeze. Russ and Danielle describe their own dynamic as “tiger and turtle,” with one partner wanting to press in and solve things immediately while the other shuts down and needs time to process. Instead of treating that reaction as failure, they show why self-awareness is the starting point for healthier conversations. That is where one of the episode’s central ideas comes in: be curious, not furious. Rather than trying to win or prove a point, they encourage listeners to ask better questions, use phrases like “tell me more,” and listen as if they might be wrong.  The conversation also explores how past experiences shape present reactions. Russ explains how old wounds and emotional memories can intensify present-day tension, making a small moment feel much bigger than it is. That insight opens the door to a larger point: strong relationships are not built by avoiding discomfort. They are built by learning how to work through hard things with honesty, vulnerability, and respect. Michael, Russ, and Danielle connect this not only to marriage, but also to leadership, teamwork, emotional intelligence, and the ability to solve problems well in any environment.  This episode is for couples trying to communicate more clearly, leaders navigating tension at work, and anyone who wants to build stronger long-term relationships without pretending conflict should never happen. It is a grounded conversation about repair, emotional intelligence, and the courage it takes to stay engaged when things get hard. 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

    44 min
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About

Hosted by Michael Cupps, The Habit Architect is designed to help you intentionally build the habits that lead to success and break free from those that hold you back.  Each episode, Michael guides you through practical strategies for designing focused, productive days that align with your goals and vision. Whether you’re striving for personal growth or professional success, this show will help you create the daily routines and mindset shifts needed to unlock your full potential.  Tune in for expert insights, actionable steps, and real-life examples to transform your habits and build the life you desire—one intentional habit at a time.

Information

  • Creator
    Michael Cupps
  • Years Active
    2025 - 2026
  • Episodes
    55
  • Rating
    Clean
  • Copyright
    © 2026 The Habit Architect
  • Show Website
    The Habit Architect