S03 EP01 with Jared Webb - Welcome to Season 3: Good Data, Wrong Story

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 [https://www.enterprisediagnostics.ai/] and Time Bandit [https://timebandit.io/] Check out our Live Show Events here: The Habit Architect Live Show [https://www.linkedin.com/in/michaelcupps/recent-activity/events/] Subscribe to our Newsletter: The Habit Architect Newsletter [https://www.linkedin.com/pulse/welcome-habit-architect-building-your-blueprint-success-michael-cupps-fq5kc/?trackingId=6JugMhfyQR6Xaqm9vzk8fA%3D%3D]

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 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 who've both been around long enough to say what they actually think. John's story starts on a football field. He was a collegiate player headed toward the NFL until a broken neck in a 1998 game in college changed everything. What he carried out of that experience wasn't bitterness. It was the same discipline and habit of preparation that football demands, applied to business and computer science. He went on to join Accenture, co-found multiple companies, and is now running MorelandConnect alongside raising six kids in Cleveland, Ohio. The conversation covers what happens when companies rush toward AI without cleaning up their priorities first. John makes the case that the fundamentals haven't changed. You still need to know what's important now, what to hand off, what to drop, and what only a skilled human can own. AI accelerates execution. It doesn't fix broken thinking about where to focus. Cupps brings the Eisenhower Matrix into it, specifically the quadrant most people avoid: the one where you just stop doing the thing. John ties that directly to his concept of extreme ownership and where it can actually work against you if you never learn to let go. They also get into MorelandConnect's Foundation platform, which the company built to address one of the most stubborn problems in enterprise technology: disconnected data systems that speak different languages. John explains how Foundation uses AI to accelerate mainframe modernization, a challenge that has been growing for decades and is now finally solvable at scale. The episode ends with Season 2's new closing question, introduced as a potential Season 3 signature: what have you handed off to AI, and why did it stay on your list so long? John's answer is arrangement letters and statements of work, something that used to eat hours and now takes minutes. Season 3 launches in late June with a sharper focus on AI and priority management for teams. The Habit Architect is sponsored by Enterprise Diagnostics [https://www.enterprisediagnostics.ai/] and Time Bandit [https://timebandit.io/] Check out our Live Show Events here: The Habit Architect Live Show [https://www.linkedin.com/in/michaelcupps/recent-activity/events/] Subscribe to our Newsletter: The Habit Architect Newsletter [https://www.linkedin.com/pulse/welcome-habit-architect-building-your-blueprint-success-michael-cupps-fq5kc/?trackingId=6JugMhfyQR6Xaqm9vzk8fA%3D%3D]

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 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 content that bridges the gap between a photograph and a felt memory, and the results are hard to argue with. The conversation covers how the brain stores experience differently when you're inside it versus watching it, what it takes to get politicians and major funders to actually feel why ending polio matters, how the Minnesota United used VR to turn a stadium tour into a sponsorship tool, and why Amir believes spatial computing is heading the same direction the internet did in the 1990s. Whether you believe it or not is almost beside the point. The train is already moving. Cupps and Amir also get into what this means for anyone trying to build habits tied to things they haven't experienced yet, and why, if you can feel the outcome before you reach it, the commitment to get there tends to hold. Connect with Amir Berenjian: linkedin.com/in/amirberenjian REM5 Studios: rem5studios.com The Habit Architect is sponsored by Enterprise Diagnostics [https://www.enterprisediagnostics.ai/] and Time Bandit [https://timebandit.io/] Check out our Live Show Events here: The Habit Architect Live Show [https://www.linkedin.com/in/michaelcupps/recent-activity/events/] Subscribe to our Newsletter: The Habit Architect Newsletter [https://www.linkedin.com/pulse/welcome-habit-architect-building-your-blueprint-success-michael-cupps-fq5kc/?trackingId=6JugMhfyQR6Xaqm9vzk8fA%3D%3D]

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 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 Effortless Abundance is the idea that top performers are not working harder than everyone else. They're working with less waste, more strategy, and a clear understanding of why they're doing what they're doing. That clarity is the thing that makes habits stick. The conversation gets honest about what burnout actually looks like from the inside, how performance can quietly become a value that slowly breaks you, and why subtracting the wrong things often has to come before adding any new habits at all. Michael shares his own story from a sales cruise he spent mentally checked out, distracted by a software deal, with his son nearby, and what a cancer diagnosis a few years later made him reckon with about the way he had been operating. Meg also walks through her Sales Archetype Workshop, the Jungian framework she uses to help reps find the energetic identity that connects their habits to something they actually care about. And both she and Michael agree on something that tends to get buried in high-performance environments: values are not the words in your notebook. They are the choices you make every single day. Connect with Meg Misiak: linkedin.com/in/megmisiak Rate The Habit Architect on your favorite listening platform! The Habit Architect is sponsored by Enterprise Diagnostics [https://www.enterprisediagnostics.ai/] and Time Bandit [https://timebandit.io/] Check out our Live Show Events here: The Habit Architect Live Show [https://www.linkedin.com/in/michaelcupps/recent-activity/events/] Subscribe to our Newsletter: The Habit Architect Newsletter [https://www.linkedin.com/pulse/welcome-habit-architect-building-your-blueprint-success-michael-cupps-fq5kc/?trackingId=6JugMhfyQR6Xaqm9vzk8fA%3D%3D]

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 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 to the table. She's new to running her own business, managing multiple clients, juggling production work, and trying to hold her habits together. Everything on her list feels urgent and important, which means nothing actually gets prioritized. Cupps walks her through the four quadrants of the matrix, Do First, Schedule It, Delegate, and Park, and explains why a flat to-do list is designed to fail. They get into the real difference between a task, a calendar event, and deep work. Flor's strategy sessions, the kind that take two hours of data collection before a single decision gets made, don't belong on a task list at all. That's time that needs to be blocked, protected, and treated as non-negotiable. The same goes for habits. When the task list swallows everything, the habits that keep you functioning go first. They also take a live question from Blake about underestimating time, work through the delegate quadrant with a real example, and talk about what work-life integration actually means when you're a business owner trying to hold it all together. The matrix is free. No catch. Go try it at matrix.timebandit.io and bring your actual task list. The Habit Architect is sponsored by Enterprise Diagnostics [https://www.enterprisediagnostics.ai/] and Time Bandit [https://timebandit.io/] Check out our Live Show Events here: The Habit Architect Live Show [https://www.linkedin.com/in/michaelcupps/recent-activity/events/] Subscribe to our Newsletter: The Habit Architect Newsletter [https://www.linkedin.com/pulse/welcome-habit-architect-building-your-blueprint-success-michael-cupps-fq5kc/?trackingId=6JugMhfyQR6Xaqm9vzk8fA%3D%3D]