The Habit Architect

Michael Cupps kicks off episode two of Season 3 with Joey Chandler, founder of Certain Growth Solutions and creator of the Alignment Engine framework. Chandler walks through how identifying three core values (not goals, not categories) changes the way people show up under stress, at 3am, and everywhere in between. The conversation covers the six-question process Chandler built after his own burnou...

Season three of The Habit Architect opens with a shift. Michael Cupps has spent two seasons talking about personal habits and individual time management, and now he's turning the lens toward teams, companies, and what it actually takes to grow in an AI-accelerated world. The first guest in that conversation is Jared Webb, a customer success leader with nearly 15 years of experience inside Saa...

Michael Cupps closes out Season 2 of The Habit Architect with a conversation he's been looking forward to for a while. His guest, John Lurtz, is the Co-Founder of MorelandConnect, a Cleveland-based custom cloud software company, and someone Cupps has known for years. The two have a lot of shared professional history, which makes this one feel less like an interview and more like two people wh...

Most people try to change their behavior by thinking differently. Amir Berenjian thinks you have to feel it first. In this episode of The Habit Architect, Michael Cupps sits down with Amir Berenjian, CEO and co-founder of REM5 Studios, to talk about what happens when you stop trying to explain an experience and actually let people live it. Amir has spent the last decade building immersive VR conte...

Hustle culture has a way of convincing you that the answer is always more. More calls, more hours, more systems, more data. Michael Cupps sits down with Meg Misiak, a sales training expert who spent 12 years scaling teams at companies like HubSpot and Blend before burning out herself, to talk about what it actually looks like to stop doubling down on the wrong habits. Meg's concept of Effortl...

Most people know they have too much on their plate. What they don't know is why their to-do list keeps growing no matter how hard they work. In this episode, Michael Cupps sits down live with Florencia Llosas, producer of The Habit Architect and founder of her own marketing agency, to walk through a free tool Cupps built: the Priority Matrix at matrix.timebandit.io. Flor brings a real problem...

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. Hares...

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 w...

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...

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 o...

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....

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 j...

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 r...

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...

Growth doesn’t usually stall because people stop caring. It stalls because teams are solving problems from different angles, leaders are chasing priorities without shared clarity, and progress gets buried under misalignment, mixed signals, and habits that no longer support the next stage of growth. In this episode of The Habit Architect , host Michael Cupps talks with Nataly Huff , founder of Inno...

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...