The Habit Architect

Bhavna Kumar, co-founder of Secret Startup Series and former VP of Network at Techstars, joins Michael Cupps to break down how founders raise pre-seed and seed rounds in Dallas and North Texas. She covers building an investor CRM, getting warm introductions, handling investor rejection, and why women founders are still underrepresented in venture capital. They also discuss the silver tsunami of re...

Healthcare AI is delivering real results right now, but not where most leaders are looking. In this episode, Michael Cupps sits down with Shani Fargun, VP of Healthcare at StackAI, to break down where agentic AI is producing ROI in health systems today and why the organizations seeing results started with the workflows nobody wanted to touch first. Shani brings a rare combination of clinical opera...

Robert Moseley spent years watching sales teams run quarterly business reviews on completely fabricated pipeline data. Reps were doing exactly what the system trained them to do. It was built for managers to report, not for sellers to sell. In this episode of The Habit Architect, Michael Cupps sits down with Rob Moseley, founder of GTM Engine, and Craig Witt , their CRO, to get into why CRM data q...

When the guest doesn't show, the producer comes out to play. Michael Cupps and marketing strategist Florencia Llosas get into what it costs when a founder is the entire go-to-market function: closing deals, managing relationships, holding the pipeline together personally. Through a real diagnostic on a $5 million agency, they trace $2.3 million in untapped profit back to two problems: custome...

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 Sibyl Consulting Group , leads community at MSP Unplugged , and is in the middle of a new acquisition. This episode takes the listener through what it took to shift from reactive operator to proactive one, why delegation is the growth leve...

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 asked him to train a global salesforce and he had no idea where to start. What he found became Sales Method . Now it's a book. In this episode, Michael Cupps and Ken Powell get into why 69% of reps miss quota and why...

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 in this episode of The Habit Architect, he and host Michael Cupps get into what that actually looks like in 2026. Hughes co-founded DLA Ignite, where he has...

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 actually use AI in your business, and how do you know if you are doing it right? Cupps opens with a framework he calls the three pillars of AI adoption: ope...

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: context. In this episode of The Habit Architect, Michael Cupps sits down with Yohann Doillon, co-founder and deployment strategist at 10x Partners, t...

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 organization and why most companies are still not equipping their people to handle it. Natalie spent more than 20 years in corporate America across tech, finance, forest...

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...