S2 E20: Max Turigliatto: Building A Speakeasy In Santa Cruz | Owning The Coast

You've probably heard someone say "Santa Cruz needed a place like that." Max Turigliatto, the Santa Cruz native behind Alley Oop, tells us what "that" really means. Alley Oop is a speakeasy-style cocktail lounge built for date nights and live music. It feels like it could be anywhere in the world, but it's still unmistakably local. Max shares how keeping his day job selling lumber at Big Creek let him play the long game. He also talks about turning down "bad money," finding investors who believe in the vision, and sweating the details: lighting, sound, pacing, and hospitality that feels warm instead of performative. Then we zoom out to the bigger Santa Cruz story: housing mandates, fast development, frustration with rebuilding after the fires, and the fear of becoming Anywhere, USA. Max makes the case that local creators can shape what comes next with integrity, fair pricing, elevated mocktails and a serious live music program. The music program draws on Alley Oop's neighbor, Kuumbwa Jazz, and a vintage baby grand piano. CHAPTERS 0:00 Meet Max and his roots 2:06 Growing up in a bar 4:18 Why restaurant work changes you 6:00 The day job that funds the risk 8:05 Investor fit and healthy money 12:05 Designing an elevated guest experience 14:20 Downtown Santa Cruz growth tensions 18:46 Housing mandates and fire rebuild friction 25:08 Community support and a better night out 29:20 The Alley Oop concept and buildout 35:33 Cocktails to order and press wins 39:06 Live music dreams and the perfect piano 43:24 Events, food, pricing and the long game 48:17 Where to find Alley Oop Visit The Alley Oop 📍 320 Cedar St, Santa Cruz (Jazz Alley, next to Kuumbwa Jazz) 🌐 Website and live music calendar: jazzalleylounge.com 📸 Instagram: @thealleyoop Hosted by Brandi Jones (Keller Williams Thrive), Ryan Buckholdt (CrossCountry Mortgage) and Jerry Seagraves (Seagraves Insurance). If you care about Santa Cruz nightlife, small business and the future of downtown, subscribe and share this with a friend who needs a better date-night spot. LISTEN ON OTHER PODCAST PLATFORMS https://play.headliner.app/episode/35839964?utm_source=youtube Brandi Jones | REALTOR® | KW Thrive Santa Cruz 🏡 Real estate strategy + aligned decisions for your next chapter. Reach out anytime if real estate is part of your next chapter. 📞 (831) 588-5145 🌐 brandijonesrealtor.com 📍 Santa Cruz • Monterey Bay • Santa Clara County DRE# 01385191 #OwningTheCoast #AlleyOop #DowntownSantaCruz #SantaCruz