The Habit Architect

Michael Cupps
  • 5.0 (1)
  • Entrepreneurship
  • Updated Weekly

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.

  1. 1d ago

    How to Raise Money for Your Startup: The Venture Playbook | Secret Startup Series, Bhavna Kumar

    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 retiring business owners, entrepreneurship through acquisition, and how AI is changing who can start or buy a company. The Habit Architect is sponsored by Enterprise Diagnostics and Time Bandit Check out our Live Show Events here: The Habit Architect Live Show Subscribe to our Newsletter: The Habit Architect Newsletter

  2. Sep 25

    AI in Healthcare: Why It Works When It Works | AI Stack, Shani Fargun

    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 operations experience, a background at Anthem, medical device, and MIT's Sloan Fellows program, and hands-on deployment of AI agents inside real healthcare environments. This is a practical conversation about what works, what stalls, and how to think about AI investment before you sign anything. Key takeaways: Why the administrative layer, not clinical AI, is where healthcare ROI is happening nowHow agentic AI differs from chat interfaces and why that distinction matters at scaleWhy payers and providers adopt differently and where to expect the most tractionWhat a three-month proof of value looks like before a full AI deploymentHow to protect patients and maintain human accountability while scaling AI workflowsThe Habit Architect is sponsored by Enterprise Diagnostics and Time Bandit Check out our Live Show Events here: The Habit Architect Live Show Subscribe to our Newsletter: The Habit Architect Newsletter

  3. Sep 11

    S03 EP11 with GTM Engine - Your Pipeline Has a Clot

    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 quality has always been broken and why bolting AI onto a bad data foundation only gives you a faster way to produce a confidently wrong sales forecast. Why do reps enter bad data? Because the system rewards them for it. What does signal collection from calls, emails, and customer success interactions actually change about pipeline visibility? Quite a bit, it turns out. Why are CFOs spending hours every Monday verifying revenue data they already suspect is wrong? That one comes down to a problem nobody wants to say out loud in a forecast call. The conversation also covers what Salesforce partnering with Anthropic still does not solve for go-to-market teams, what PE-backed portfolio companies need from their revenue forecasting that most CRM implementations are not delivering, and why cleaning your CRM data is the prerequisite every GTM strategy skips. This episode marks the beginning of a new partnership between Enterprise Diagnostics and GTM Engine. Find Robert and Craig at gtmengine.ai Connect with Michael Cupps at linkedin.com/in/michaelcupps Sponsored by timebandit.io and enterprisediagnostics.ai Produced by A Cheshire Creative. The Habit Architect is sponsored by Enterprise Diagnostics and Time Bandit Check out our Live Show Events here: The Habit Architect Live Show Subscribe to our Newsletter: The Habit Architect Newsletter

  4. Aug 28

    S03 EP10 with Flor Llosas - Stop DIYing Your Growth

    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: customer concentration and a sales process that stops working the moment the right person steps away. The conversation moves into AI in sales and marketing, CRM data quality, why referral pipelines have a ceiling, and what founders get wrong when they add channels before building a system. Plus a live GTM webinar coming in late September. The Habit Architect is sponsored by Enterprise Diagnostics and Time Bandit Check out our Live Show Events here: The Habit Architect Live Show Subscribe to our Newsletter: The Habit Architect Newsletter

  5. Aug 14

    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 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 lever most owners resist longest, and how AI is landing across the MSP space right now. Nancy also opens up about Claudia, the AI second brain she built on Claude, seeded with her own book and coaching frameworks, that now manages her inbox, reads meeting sentiment, and coaches her on her own capacity. Author of Break-Fix to Breakthrough. First generation American. ADHD superpowered woman.  The Habit Architect is sponsored by Enterprise Diagnostics and Time Bandit Check out our Live Show Events here: The Habit Architect Live Show Subscribe to our Newsletter: The Habit Architect Newsletter

  6. Aug 7

    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 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 the answer has nothing to do with technology, what forecast accuracy actually reveals about a team's habits, how debriefing a lost deal the way a team watches game film separates the sellers who compound from the ones who plateau, and where AI outreach is creating discipline problems nobody wants to name yet. Raise the Bar. Step Up.: The Habits of Great Sales Athletes is available now on Amazon.  Find Ken at salesmethod.com Produced by A Cheshire Creative. The Habit Architect is sponsored by Enterprise Diagnostics and Time Bandit Check out our Live Show Events here: The Habit Architect Live Show Subscribe to our Newsletter: The Habit Architect Newsletter

  7. Jul 31

    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 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 trained thousands of B2B salespeople to build pipeline through social rather than outbound volume. His fourth book, Social Selling and Influence, published in early 2026, brings together ten years of research and field work, including a chapter on where AI fits into modern selling. He has also launched Azpertilo, an AI-native platform built on Claude and Gemini that generates personalized, on-brand content for sales teams at scale, grounded in each individual's own tone of voice. The conversation covers the core principles of social selling, why LinkedIn ads are largely ignored while organic content compounds, how to write posts that get indexed by both Google and large language models, and why the companies generating multi-million dollar deals on social are doing nothing most sales leaders would recognize as outreach. Cupps and Hughes also dig into what happens when companies hand their teams a tool without training, the difference between AI washing and real AI application, and why Hughes kept human coaching in the Azpertilo product even after building the automation to replace it. The episode connects directly to the AI readiness themes raised in Episode 5, this time from the seller's side of the equation. Connect with Timothy Hughes: linkedin.com/in/timothy-hughes  Learn more about DLA Ignite: dlaitb2b.com  Azpertilo: azpertilo.ai The Habit Architect is sponsored by Enterprise Diagnostics and Time Bandit Check out our Live Show Events here: The Habit Architect Live Show Subscribe to our Newsletter: The Habit Architect Newsletter

  8. Jul 24

    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 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: operational efficiency, customer experience, and industry awareness. The conversation moves through each pillar with real examples, from IVR systems that customers hate but companies keep because they deflect calls, to small businesses that can now engineer customer experiences that enterprise companies cannot match. Flor brings the ground-level view, the agency owner figuring out which tools are worth the subscription and which ones just feel urgent because LinkedIn says so. The episode is a conversation between two people who work in this world every day. No hype. No "AI is gonna change your life." Just the questions that operators actually have, and some honest answers about where businesses are getting it right and where they are absolutely getting it wrong. Enterprise Diagnostics, the presenting sponsor of Season 3, is also discussed in context: Cupps explains how their diagnostic assessment maps directly to all three pillars, helping businesses understand where to place their bet before they make the investment. Topics covered in this episode: The three pillars every business should evaluate before spending on AI: operations, customer experience, and industry positioning. Why giving your team Claude or Copilot does not make you an AI company. The IVR problem: when cost-cutting disguises itself as customer service. How small and mid-market businesses can move faster than large companies and why that window matters. The difference between experimenting with tools and making a strategic industry bet. Why AI will tell you whatever you want to hear, and what that means for the questions you ask it. How priority management applies to AI decisions the same way it applies to everything else in your business. The Habit Architect is sponsored by Enterprise Diagnostics and Time Bandit Check out our Live Show Events here: The Habit Architect Live Show Subscribe to our Newsletter: The Habit Architect Newsletter

See All (71)

About

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.

Information

  • Creator
    Michael Cupps
  • Years Active
    2025 - 2026
  • Episodes
    71
  • Rating
    Explicit
  • Copyright
    © 2026 The Habit Architect
  • Show Website
    The Habit Architect