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. 2d ago

    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

  2. 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

  3. 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

  4. 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

  5. Jul 20

    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: context. In this episode of The Habit Architect, Michael Cupps sits down with Yohann Doillon, co-founder and deployment strategist at 10x Partners, to talk about what it actually takes to bring AI into production at the business level. Yohann comes from the Palantir ecosystem and has spent five-plus years building ontology-based data foundations for companies ranging from Fortune 500 firms to growth-stage scale-ups. He and his partners are senior-only engineers, by design. Their work is translating how a business actually operates into a digital structure that agents and AI systems can understand and act on. The conversation covers the three pillars 10x uses to assess AI readiness: internal operations, product strategy, and competitive risk. Yohann walks through what data readiness actually looks like versus what companies say when asked about it, why buying 10,000 Copilot licenses is not an AI strategy, and what an ontology is in plain language, not the jargon version. Michael ties it back to his own years in the RPA and BPM world, and together they work through a live insurance industry example where 14 disconnected systems are being brought into one coherent picture so that real decisions can get made. They also get into the question of whether a nine-month consulting engagement is the only way to assess your AI readiness (it isn't), what it means for a company to have a "living" AI assessment rather than a snapshot, and the personal second-brain system Yohann has built that his own partners are tired of hearing about. 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. Jul 13

    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 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, forestry, transportation, and defense before leaving in 2020. She watched the same pattern play out across all of them: 60% of new managers step into leadership without any formal training, and the employees underneath them are given no framework for navigating what comes next. Her ANCHORed Accountability model was built to close that gap, from both sides of the desk. The conversation covers the trust bank, the false alignment trap, what the Challenger disaster and Enron have in common with most mid-market businesses, and why one in three employees said staying silent cost their organization at least $25,000. Natalie also gets into the AI disruption conversation from a grounded, personal angle, including why she thinks our ability to adapt is already inside us, and what leaders will need to stop doing if they want their teams to use new tools well. Connect with Natalie Parker: linkedin.com/in/natalie-renee-parker thenatalieparker.com | yourbosssucks.com  Watch Natalie's TEDx Talk here 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 6

    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 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 burnout, how those questions work as both a performance tool and a recovery tool, and what happens when someone's public persona drifts away from what they actually value. Chandler shares a client story about a divorce, a TikTok following built on anger, and the choice to walk away from what wasn't working. Cupps and Chandler also dig into AI: what changes when you feed your values into a tool like Claude or Gemini, and why the same technology that makes AI more useful to you is the technology that could replace you if you're not careful about what you're actually asking it to do. The episode closes with Chandler's own answer to the Season 3 signature question: what he's handed off to AI, and why. 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. Jun 29

    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 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 SaaS companies, most of it in health tech and fintech. The episode centers on a problem most SaaS leaders know but don't always say out loud: the data exists, and the boardroom still isn't acting on it. Webb breaks down why that happens and what CS teams can do about it. Cupps and Webb dig into customer health scores, where the data lives in early-stage companies (usually in inboxes and personal spreadsheets), and how to build a scoring system that actually reflects what's happening in the customer base versus what the team feels is happening. Webb makes a distinction that shapes the whole conversation: feeling isn't a metric. The companies that protect revenue are the ones that make customer signals visible, trackable, and defensible. They also get into what AI is changing in the CS world. QBR prep that used to take three days can now take three hours. That freed-up time is not just an efficiency gain; it's an opportunity to have the conversations that only a human can have. Webb's view is that CS teams that figure out how to pair their relational instincts with better data will outlast the ones that get replaced by forward-deployed engineers or automated agents. The episode wraps with Season 3's new closing question. Cupps asks Webb what he would hand off to AI tomorrow and why it's been sitting on the list. Webb's answer: the sales-to-CS handoff. It's where the most context gets lost and where the first 90 days of a customer relationship either get built on a solid foundation or start with a gap that never fully closes. Don't forget to rate and review the show on your preferred platform. It helps more people find it. Connect with Jared Webb: linkedin.com/in/jaredwebb 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

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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
    67
  • Rating
    Clean
  • Copyright
    © 2026 The Habit Architect
  • Show Website
    The Habit Architect