Season 88, Episode 1055: 2025 NYE Lollapalooza Episode 8: Awake, Persevere, Improve

Episode 8 of the New Year’s Eve Lollapalooza is a fast-moving mix of real talk, hard lessons, and the kind of “in-the-trenches” clarity you only get when builders stop pretending everything is polished.

Jay Doran and co-host Mike Calhoun are joined by Vinnie Candelore Jr., Jeff Winnick, Jake Penny, Kayvon Kay, and returning guest Demetri Stakias for a conversation centered on two themes: what 2025 demanded from you, and what 2026 is requiring of you.

Here’s what makes this episode hit:

Jake Penny breaks down a mission-driven approach to “Main Street investing” through Wealth Without Wall Street—teaching people how to move retirement dollars into cash-flowing real estate with real social impact. He shares the reality of scaling a portfolio (134 properties in four years), the pressure of a changing capital market, and the word that carried him: Persevere.

Vinnie Candelore Jr. speaks like someone who finally woke up to what entrepreneurship actually is. Art may get you in the room—but relationships, systems, and execution keep you there. His word for the year: Awake. And his story is a live look at what it means to build something for your family while still learning the game in real time.

Kayvon Kay brings the edge and the honesty. He talks about the founder being the bottleneck, the necessity of surrender for real growth, and what it looks like to come out of a year where the goal was simply to exist—and still end up with massive momentum. His takeaway lands hard: you don’t get growth without surrender.

Jeff Winnick shares “mortgage miracles” from a small team producing big results—and then gets pushed (in the best way) to define what “better” really means in 2026. The answer becomes clear: more leverage, stronger delegation, and improving as a human first.

And through it all, Jay and Mike keep coming back to the point of the Lollapalooza itself: connection. The people in your world matter. The way you show up matters. And leadership isn’t just output—it’s care.

If you’re building through a pivot, a reset, or a reinvention… this episode will feel like a mirror and a push.

Share this episode with someone who needs a wake-up call—and leave a review so we can keep bringing conversations like this to more people.