Residential Remix Podcast Season 2 Special Episode : Weddings, Wall Street & Wild Nights in the Keys

In this special on-the-road episode of the Residential Remix Podcast, Dennis and Derek take the show to Islamorada for a destination wedding weekend—and they finally bring on their longtime friend and DJ, Alex Gregory, as a guest. The trio shares hilarious stories about DJing high-end weddings, the challenges of working with planners, and why having a signature brand is key to success.

They also dive into the evolving nightlife scene, the do’s and don’ts of wedding playlists (spoiler: group dances are out), and Alex’s unexpected journey into the world of insurance and stock trading. Plus, they swap celebrity encounters—from wild nights with big-name DJs to surprise run-ins with Bon Jovi’s pianist.

With tequila in hand and a hurricane brewing outside, this episode is full of laughs, insights, and behind-the-scenes stories from the world of music, events, and business.

Takeaways

This is a special edition of residential remix.
It's a boys weekend. It's a vacation.
We want our name in their mouth.
No group dances, no cha cha slides.
If you can play well in West Palm, you can destroy it in Vegas.
You have to stomach big losses.
Put $100 a month into any index fund.
You can't sell at the tops and bottoms.
It's all about pleasing the people.
Navigating the wedding industry requires understanding client preferences. 401ks are great if you have a job.
Emotional decisions can lead to poor investment choices.
Insurance is often seen as a necessary evil.
Life insurance can provide financial security for families.
DJing can be a burnout lifestyle but also rewarding.
Private events can be more lucrative than nightclubs.
Aging in the nightlife scene presents unique challenges.
Celebrities often just want to have fun like everyone else.
Treating celebrities like normal people can lead to great interactions.
Memorable moments in DJing often come from unexpected encounters.