Jason Restivo was my GM at the Old Pink House in Savannah, Georgia — the guy who would disappear for five minutes and come back to a dining room with a bottle of wine on every single table. He was also the reason I got the job in the first place when someone else in management wasn't so sure.

Now he owns Sobremesa on 40th and Abercorn — a restaurant he built out of a wine bar that used to be a dentist's office, in a neighborhood that used to be a gas station, in a district that had absolutely nothing going on when he opened Atlantic back in 2016.

Spoiler: Starland is now the food mecca of Savannah.

We got into it all — how he left California real estate behind for a Victorian house in Savannah for $146K, what it was really like to run Atlantic with 40 staff before COVID shut it down, why he thinks mentorship is the whole point of the restaurant industry, how he got staff members out of debt and into their first homes, cell phones vs. fine dining, Bill Murray, Patricia Arquette, and his daughter heading out into the world at 17.

Plus — he dropped out of engineering school to be a busboy in a thousand-dollar suit and never looked back.

⏱ CHAPTERS:
00:00 Reconnecting After Years
02:57 The Evolution of Starland District
05:50 Opening Atlantic: A New Dining Experience
11:46 Transitioning to Sobre Mesa
14:54 Savannah's Restaurant Scene Growth
20:02 Nostalgic Memories in Savannah
20:25 Introduction to the Podcast Journey
23:09 Nostalgia and Memory in Wine
26:05 The Art of Service and Mentorship in Hospitality
27:37 The Importance of Mentorship in Hospitality
28:34 Transformative Experiences at the Pink House
29:33 Empowering Staff for Success
30:45 The Evolution of Interviews
32:08 Small Business and AI
38:14 Family and Parenting
43:56 Networking and Building Connections
49:57 Memorable Experiences and Celebrity Encounters

🎙️ 20-Year Timeout — reconnecting with people from the past, unscripted and unfiltered.

📲 Website: https://www.20yeartimeout.com

Send us Fan Mail

Subscribe for new episodes and honest conversations.

20 Year Timeout is a podcast where I reconnect with people I have not spoken to in over twenty years to see what time has done to our stories.

Listen & Watch Here:
https://open.spotify.com/show/7Aa3P0QSufFWzgbUSOtUTB

https://podcasts.apple.com/us/podcast/20-year-timeout/id1862794471

https://www.youtube.com/@richmarksthespot

Alan — aka LOA — and I used to close shifts together, order Ming House Chinese at midnight, and record tracks in my apartment with half-broken cords and mics peaking at zero. That was the Via era. Then life happened.

Now he's in Fort Lauderdale teaching Pilates and yoga at 6AM, training an 83-year-old client and a 12-year-old kid, freestyling with his daughter in the living room, and painting Basquiat-inspired portraits on five canvases in a month because a videographer gave him a deadline.

He's also got a mentor, a plan, and an easel in the background — and he still won't tell me what LOA stands for.

We got into it all: going plant-based, tearing his ACL in a bar fight and healing it through Bikram yoga, the environmental cost of AI, doom scrolling, Mac Miller, Nas's new stuff, building a treehouse, and what it means to finally invest in yourself.

Oh — and we made some music together back in the day. You'll hear about that too.

⏱ CHAPTERS:
00:00 Reconnecting Over Ming House & Old Times
05:33 Memories of Via & The Restaurant Years
11:04 Going Plant-Based (Mostly)
21:45 Tearing His ACL in a Bar Fight & Healing Through Yoga
27:25 Getting Flexible: The Bikram Journey
30:26 Teaching Pilates & Finding a New Lane
35:08 Still Rapping — Freestyling With His Daughter
40:32 Painting Basquiat, One Month Deadline
45:06 What Style Is He Building Toward?
51:26 Landing in Fort Lauderdale
58:46 Training Clients of All Ages
01:01:23 Investing in Yourself
01:06:30 Building Connections and Networking
01:14:53 Setting Goals for the Podcast
01:25:50 Rap Right Now — Nas, Nav, Mac Miller
01:30:07 What Does LOA Stand For?
01:34:03 The Environmental Cost of AI
01:37:34 Disconnecting from Tech
01:39:10 Collages, Magazines & Creative Therapy
01:41:11 Building a Treehouse, Living Through the Kids

🎙️ 20-Year Timeout — reconnecting with people from the past, unscripted and unfiltered.

📲 Website: https://www.20yeartimeout.com

Send us Fan Mail

Subscribe for new episodes and honest conversations.

20 Year Timeout is a podcast where I reconnect with people I have not spoken to in over twenty years to see what time has done to our stories.

Listen & Watch Here:
https://open.spotify.com/show/7Aa3P0QSufFWzgbUSOtUTB

https://podcasts.apple.com/us/podcast/20-year-timeout/id1862794471

https://www.youtube.com/@richmarksthespot

I finally tracked down Mr. Craig Darrell — my 8th grade Religion teacher from Holy Name in Worcester, MA. We hadn't spoken since 2004. Turns out he's been living in Leavenworth, Kansas, working with special needs kids, and still remembers every single stunt I pulled in his class. Oh — and I still have the detention slip.

We talk about what it was really like teaching in the '90s vs. today, why he walked away from 22 years of teaching, playing semi-pro football for 17 seasons, working as a bouncer at Jillian's (where he caught me underage), painting ceramics to stay sane, and why the kindergartners he works with now are teaching HIM more than he ever expected.

This one got real. Mental health, family, distance from grandkids, and what it means to actually show up for people — Mr. Darrell never stopped teaching. He just changed his classroom.

⏱ CHAPTERS:
00:00 Reconnecting After Years
02:54 Choosing Holy Cross: A Journey of Discovery
06:12 Life Lessons from College Football
08:59 The Transition to Teaching
12:12 Challenges in Modern Education
15:05 The Evolution of Teaching Methods
17:59 Teaching Special Needs: A New Perspective
20:47 Life Skills and Real-World Applications
24:01 The Importance of Diverse Learning Experiences
28:00 Problem Solving and Adaptability
29:11 Exploring Career Paths and Personal Growth
30:07 The Impact of Sports on Life
31:59 Hobbies and Finding Relaxation
35:04 Mental Health and Life Challenges
37:03 The Importance of Community and Family
37:46 Navigating Technology and Childhood
39:56 Experiences as a Bouncer and Bartender
42:48 Reflections on Teaching and Mentorship
46:00 The Value of Family and Presence
48:47 Lessons from Children and Innocence
58:46 The Importance of Empathy in Education
01:01:09 Reflections on Growing Up and Community
01:06:30 Memories of Mischief and Learning
01:11:01 The Impact of Teachers on Students
01:15:11 Cherishing Memories and Life Lessons
01:21:31 Connecting Through Social Media

🎙️ 20-Year Timeout is a podcast about reconnecting with people from your past — unscripted, real, and always surprising. New episodes dropping regularly.

📲 Follow along:
Website: https://www.20yeartimeout.com

Send us Fan Mail

Subscribe for new episodes and honest conversations.

20 Year Timeout is a podcast where I reconnect with people I have not spoken to in over twenty years to see what time has done to our stories.

Listen & Watch Here:
https://open.spotify.com/show/7Aa3P0QSufFWzgbUSOtUTB

https://podcasts.apple.com/us/podcast/20-year-timeout/id1862794471

https://www.youtube.com/@richmarksthespot