Season 88, Episode 1053: 2025 NYE Lollapalooza Episode 6: Fearless, Alignment, and Breaking the Mold

Episode 6 of the New Year’s Eve Lollapalooza is a collision of high standards and real humanity—where big goals meet even bigger intention.

Jay Doran and co-host Mike “Mike Drop” Calhoun welcome a powerhouse lineup: Chris Vester, Maria Quattrone, Alan Whitman, Mike Modica, Matt McHale, with Jim Sabellico jumping in briefly to give flowers where they’re due.

This episode moves fast—but it lands deep.

You’ll hear Maria Quattrone share her 2026 word—Fearless—and the launch of her coaching and course work, including the Listing Boss 90-Day Listing Accelerator. She reflects on how consistency and community carried leaders through the unexpected, and later drops a rapid-fire “top lessons of 2025” that hits like a leadership manifesto: clarity, boundaries, momentum on boring days, and why rest is a strategy—not a reward.

Chris Vester brings his signature grounding presence: 2025 was Pruning—not loss, but intentional elimination for growth. 2026 becomes Alignment, tied directly to his mission and advisory work, Align Your Nine. He reminds the room that “no is a complete sentence,” and that fewer, better things often unlock the next chapter.

Then Alan Whitman, author of Break the Mold, unpacks the journey of transforming and scaling a traditional CPA firm—and why his 2026 must be Intentional, as he prepares to step into a new CEO role for a private equity-backed platform built to manage, protect, and grow prosperity for SMBs. He shares a practical speaking lesson that sticks: if you’re trying to stop saying “um,” don’t replace it with more words—replace it with a pause.

Mike Modica adds the operator’s perspective: Discipline and becoming Replaceable—not to disappear, but to scale through systems, trust, and leadership development in a high-stakes world where mistakes cost real money.

And Matt McHale stitches it together—stewardship, leverage, and discipline—showing how relationships, consistent learning, and leadership development create compounding returns.

If you’re stepping into 2026 with a word, a vision, or a calling—this episode will sharpen it.