The Habit Architect
Season 3 of The Habit Architect is now here!
Most business owners have built habits for themselves. Fewer have built the operational habits that make their company run the way it should.
In Seasons 1 and 2, Michael Cupps sat down with leaders, operators and experts to explore the habits behind personal growth, professional performance and life's bigger transitions.
In Season 3, those same conversations move inside the business: the operational habits, priorities and decisions that determine where a company ends up. Each episode goes inside a real business to look at the decisions and priorities that are either building toward an exit or working against one.
Built for founders, CEOs, and operators at growth-stage companies, including PE-backed businesses, mid-market operators and business owners preparing for a sale or transition. Topics include operational habits, priority management, exit readiness, business systems, and the decisions that drive company performance.
New episode every week. Tune in.
Better habits build better operations.
Episodes
67 episodes
S03 EP08 with Nancy Henriquez - Coaching Process
Nancy Henriquez has been building businesses since before she had a roadmap for it. She founded an MSP, grew it, sold it, then started another one. Now she runs
S03 EP07 with Ken Powell - Discipline Over Motivation
Ken Powell spent 20 years keeping a journal. When he saw something a great seller did that nobody else was teaching, he wrote it down. He never read it front to back until a CEO a...
S03 EP06 with Tim Hughes - Outreach at Human Scale
Cold calling is running a 3% connection rate. Inboxes are buried under AI-generated spam. And sales teams are still being handed more tools and told to go faster. Timothy Hughes has been arguing for a different approach for over a decade, and i...
S03 EP05 with Flor Llosas - The AI Budget Got Approved, Now What?
Florencia Llosas, producer of The Habit Architect and founder of A Cheshire Creative, steps into the host chair for this episode while Michael Cupps takes the guest seat. The topic is one they had been circling for months: what does it mean to ...
S03 EP04 with Yohann Doillon - So you think you're ready for AI
Most companies investing in AI are not getting the return they expected. The tools are there. The licenses are paid for. And the results still aren't coming. Yohann Doillon has a clear explanation for why, and it comes down to one missing layer...
S03 EP03 with Natalie Parker - Silence Is Expensive
Michael Cupps sits down with Natalie Parker, founder of Natalie Parker Enterprises, TEDx speaker, and host of the Signal Award-winning podcast So Your Boss Sucks, Now What?, for a conversation about what silence actually costs an organ...
S03 EP02 with Joey Chandler - When Values Run the System
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 ...
S03 EP01 with Jared Webb - Welcome to Season 3: Good Data, Wrong Story
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 ...
THA S02 EP#37 - Do More by Doing Less: The AI Priority Reset
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 Cup...
THA S02 EP#36 - Feel It to Build It: How Immersive Storytelling Makes Values Personal
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...
THA S02 EP#35 - Sell With Soul: How Nervous System Regulation Builds Sustainable Revenue
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 HubS...
THA S02 EP#34 - Why You Can't Just Pick One Thing and Start: The Guide to Getting Unstuck
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 an...
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 ...
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...
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 ye...
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 disap...
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 turne...
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 ...
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 e...
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 underst...
THA S02 EP#25 - The Habit Brain: Leading Through Doubt, Momentum, and Curiosity
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 ...
THA S02 EP#24 - Revenue Habits: How Marketing Systems Work Like Personal Routines
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 ...
THA S02 EP#23 - Building the Habit of Better Questions Through AI
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 ...
THA S02 EP#18 - Your Way to the Top, Can You Say No
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 f...
THA S02 EP#17 - The Unscalable Habits That Build the Best Communities
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 f...