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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.
71 Episodes
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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 star...
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 ha...
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 faste...
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 con...
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 open...
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