2025-06-21 Gary Sheng & Sam Gregor Fashion Design Collaboration

Date: June 21, 2025
Participants: Gary Sheng, Sam Gregor, Maddie Gregor (brief appearance)
Duration: Extended conversation
Key Topics: Alpha Schools Departure, Fashion Design Strategy, China Collaboration, Creative Community Building, Future School Vision

Alpha Schools Strategic Exit & Internal Politics Analysis

Gary's Disillusionment with Alpha Schools Management

Middle Manager Power Play Incident: Gary revealed significant organizational dysfunction at Alpha Schools involving a middle manager who canceled Gary's event:

"I'll tell you what happened a little over a week ago this middle manager guy, late forties, made a power play and said, I'm gonna I'm gonna be the the judge of content and events and basically everything that Gary wants, and he literally canceled my event."

Power Grab Dynamics:

"Well, he literally made a power play. Okay. The was he met me, and then I asked for and I and I was like, okay. I'll I'll ask for advice from this guy that he's been around longer than I have... during that period, he basically did a power grab and say, no one officially owns events. Now I own events, and I'm gonna cancel this."

Impact on Gary's Assessment of Leadership: This incident fundamentally shifted Gary's view of Joe Liemandt's hiring capabilities and organizational culture:

"So that's basically, oh, you know, you can imagine how that shifted my view of Joe's ability to hire good people and you know, the chaos and internal politics."

Philosophical Alignment on Excellence vs. Mediocrity

Sam's Validation of Gary's Standards: Sam recognized Gary's exceptional standards as both necessary and challenging within existing systems:

"And it's like, if they're not ready for them... That's what I think. Like, yeah, like, I mean, you really are an artist. You know? It's it's a special ability that you have. You know? But I just think there's, like, even I just think it's just really unorganized."

Recognition of Gary's Higher Standards: Sam noted Gary's exceptional position:

"I have way higher standards for things in than billionaires. So why am I not a billionaire?"

Creative Community Philosophy & Educational Vision

Sam's OSHA Arts Education Success Model

Block Schedule Innovation: Sam described his arts school's effective educational structure:

"my school started at, like, 08:30. We had blocks schedules. So, like, Monday, Wednesday, and Friday, we had, like, blocked one, two, three, and each of them were an hour. So it was, like, three hours of school... after those three classes, like, we had conservatories because I went to an art school, OSHA. So there was, like, 20 different conservatories"

Real-World Mentorship Model: Emphasis on practitioners as guides rather than traditional teachers:

"they they weren't teachers. They were guides. Just real fucking people A lot of them that I'm still friends with today that are mentors for me."

Comprehensive Success Outcomes: Evidence of educational model effectiveness:

"every one of my friends that I grew up with in high school, is actively doing something with their life... And all my friends that went to OSHA are actively doing something in their life right now... whether it's something that they were practicing in their, you know, in high school, and they're successful."

Gary's Educational Philosophy Alignment

Arts Integration Priority: Gary emphasized the importance of comprehensive creative education:

"You know what's better than than the six hours in the day? The whole day. To art. Right?"

Vision for Educational Competition: Recognition of market opportunity:

"Like like, the the soul of it was kind of exposed... as soon as I leave alpha, I'll probably just do a competitive school."

Future School Collaboration Vision

Community-Centered School Development: Both participants envisioned schools as community-building enterprises:

"It could be, like, a the community that we're building through... hopefully, as things keep going I see mine like what having a school in the future future. So maybe that's something that even just happens in the future."

Location Strategy Discussion: Gary's thoughts on building in malleable locations:

"I'm I'm getting pretty bullish on Tulsa not because there's a lot happening there right now, but because it's malleable."

Fashion Design Strategy & Cultural Identity

"Identity in Motion" Comprehensive Wardrobe System

Daily Wear - Modern Sensei Aesthetic: Sam presented sophisticated daily wardrobe vision:

"daily outfit, daily wear. I was thinking, like, pretty much, like, almost on on, like, this, like, sensei vibe. Right? So it's, these baggy cargoes, like, different silhou different silhouettes and colors of these cargos and dress up button tees"

Gary's Enthusiasm for Sensei Vision:

"I like the kinda modern sensei type vibe."

Speaking Events - "Commanding the Room" Strategy

Statement Piece Philosophy: Sam emphasized memorable visual impact for speaking events:

"for your speaking events, like, I really want you to be vibrant... Like, I want you wearing and I didn't put too many examples of like, because I have a lot of, like, mind liquid pieces and other statement clothings where it's it's like it's it's pretty much, like, one of one pieces where it's unique."

Cultural Memory Creation: Strategic approach to audience engagement:

"People will see you speak. And you're wearing something that's, like, fly as fuck. Are just gonna remember you. People are gonna be like, oh, I remember that dude."

Chinese-American Cultural Integration

Shanghai School Context: Gary revealed serious discussions about Chinese educational collaboration:

"I don't share this with anyone. But I'm in serious talks with Shanghai. About starting a school with them. Not with Alpha, but with me."

Cultural Aesthetic Integration Request: Gary's specific direction for cultural elements:

"The more you can make me Chinese American... Just variations of that. Right? Where it's just like wow."

Traditional Elements Integration: Sam's vision for incorporating cultural heritage:

"This is, like, a traditional Chinese embroidery type. You know? So it's just kind of incorporating that as well... Color palette, red, blue, white, and."

Manufacturing & International Collaboration

China Manufacturing Network Access

Established Relationships: Sam's immediate offer of manufacturing support:

"Oh, if you're gonna China anytime soon, let me know. I have all my people down there. Like, I have free place. I have everywhere to stay, people that'll take care me. I just wanna go down there."

Direct Manufacturer Connections: Specific location and relationship details:

"There's one I have a couple in Shanghai, Xiao Xiaojong... I have, like, all the designers too just, like, based off of the references."

Coordination Enthusiasm: Sam's eagerness to collaborate on China visits:

"We'll go down there together. I wanna introduce you to all my manufacturers as well. I think it'd be really cool for you to meet them as well. And they'll take care of us."

Gary's International Timeline

Shanghai Visit Timeline: Gary's potential travel plans:

"I don't know if this is too rushed, but I might be in Shanghai in, like, three weeks. So three or four weeks."

Strategic Manufacturing Integration: Recognition of alignment between Gary's international work and Sam's manufacturing capabilities.

Creative Process & Technical Execution

Sam's Comprehensive Design Approach

From Concept to Production: Sam demonstrated sophisticated design methodology:

"like, I'll start off with, like, a huge like, design page, basically. And I'll just be fucking around with with things for a minute just, like, testing seeing what I like the best. And then once I kinda find everything, I'll put it over together on, like, an overview."

Tech Pack Development: Professional production-ready documentation:

"Like, a final overview document like this. Where it's like you know, it this is like a tech pack basically ready to send to a manufacturer if I wanted to you know, get something designed."

Specific Design Priorities

Red, White, Blue Color Scheme: Gary's specific vision:

"Imagine a white, red, and blue... So red and blue like, things like the stitching. And then I think that would fucking kill it."

Custom Elements Integration:

"I wanna incorporate all those kinda little pieces and, you know, add these, like, little chain stitch designs on, like, a simple button up... even, like, your name chain stitched the back with, like, huge dragon, like, going down."

Business Philosophy & Future Vision

Sam's Mature Business Perspective

Age vs. Execution Maturity: Sam's self-assessment of his business sophistication:

"I get I'm young. I'm 20. I'm about to 22 in, like, four days, but it's like, I move like a 42 year old. You know?"

Multi-Branch Business Strategy: Comprehensive vision for scaling creative businesses:

"me and Nolan have all of these have these two trees, like, liquid, and grounded, and they have all these branches flowing through them. And each one of these branches has the absolute potential make millions of dollars, and the blueprint is there."

Gary's Mentorship Philosophy

Earn the Right Strategy: Gary's advice on building credibility before major ventures:

"my where I feel like you should be is, like, keep crushing it as a producer... And, of course, mentor people and and figure out what works in terms of mentoring other people... And then earn the right earn the the demand."

Patient Building Approach: Long-term perspective on achievement:

"I think right now it's like, when you're younger, you have to compromise. You have to you have to build other people's visions and and whatever... So great. Just be slightly patient, but also not really that patient, honestly."

Spiritual & Philosophical Themes

Gary's Spiritual Geography Perspective

Tulsa vs. LA Spiritual Dynamics: Gary's thoughtful analysis of location and spiritual development:

"I know I try not to put push my beliefs on other people. Unless they've like asked for it. But I believe that it's a you know, there's pockets of spiritual beauty, but I think it's it's there's so much temptation there. That that gets you off of, like, the the narrow path."

Personal Spiritual Standards: Gary's honest self-assessment:

"I think other people may be stronger than I am."

Vision Clarity and Purpose

Gary's Long-term Clarity Requirement: Emphasis on clear vision development:

"It's the other thing to have a very, very clear vision of what and it could evolve as you mature. But very, very clear vision for what is better."

Experience-Based Wisdom: Gary's acknowledgment of learning through mistakes:

"I it's it's I've had to make a lot of mistakes, and be wrong a lot about what is the future to really feel like I even have an informed perspective."

Family Introduction & Network Building

Maddie Gregor Introduction

Twin Dynamic: Sam introduced his twin sister during the call:

"Gary, you met my sister? You said you ever left were we on FaceTime when you met her?... This is Gary from Texas. This is Gary. This is who I was in Texas with."

Gary's Immediate Network Integration: Gary immediately offered valuable connections:

"Well, it might be good for you to talk to forget if you met Peter Han Sam. He's like he's like a short Korean guy in his forties, he he actually is gonna be in LA soon. So you I'll I'll I'll I'll try to connect, Maddie, you with Peter because he spent eighteen months leveling up a company that does energy healing to cure cancer."

Alternative Medicine Alignment

Maddie's Naturopathic Interests: Connection to Gary's network values:

"Maddie is doing she's studying, medicine at USF. Biology. Biology, but she wants to she was gonna go to med school, but now she's thinking about doing more of, like, the naturopathic way."

Shared Systems Critique: Recognition of medical establishment limitations:

"The US bans a lot of really actual cure. Keep us yeah... you know, keep us, like, down, uneducated."

Texas Creative Impact & Relationship Foundation

Creative Tornado Recognition

Sam's Impact Assessment: Recognition of significant creative energy generated:

"Sam told me about his Texas trip, and it was, like, so inspiring... it really got so many people excited, but also got a lot of people scared because they were so much power that was being generated."

Artistic Vision Integration: Gary's sophisticated understanding of his role:

"where I'm at is, like, can I feel as an artist where my art is communities and companies, can I feel most free? To to make my vision manifest."

Traveling Sensei Vision

Identity Integration: Gary's synthesis of personal and professional vision:

"I think the traveling sensei vibe is a nice one. For me to kind of try to embody for whatever I do."

Independence Day Symbolism: Timing of major decisions:

"maybe symbolically for Independence Day, July I will have made a decision about if I'm going to go all in on a new venture."

Key Strategic Insights & Conclusions

Educational Innovation Through Arts Integration

Both participants demonstrated sophisticated understanding of educational innovation through arts integration, with Sam's OSHA experience providing concrete evidence of success and Gary's vision providing strategic framework for scaling.

Cultural Bridge-Building Through Fashion

The fashion design collaboration represents more than wardrobe development - it's cultural narrative work that could significantly enhance Gary's effectiveness as a speaker and cultural leader, particularly in Chinese-American contexts.

Manufacturing and International Network Integration

Sam's manufacturing connections in China align perfectly with Gary's international collaboration vision, creating immediate practical applications for broader strategic goals.

Generational Collaboration Model

The relationship demonstrates effective mentorship and collaboration across generational lines, with Sam's youthful energy and Gary's strategic wisdom creating synergistic potential.

Community-Centered Business Philosophy

Both participants prioritize community building and genuine human connection over purely transactional business relationships, suggesting sustainable long-term collaboration potential.

Immediate Next Steps Identified

1. Design Development: Focus on red, white, blue Chinese-American cultural integration pieces
2. Shanghai Coordination: Potential joint travel to China for manufacturing and cultural exchange
3. Educational Model Documentation: Continued development of arts-integrated educational approaches
4. Network Integration: Introduction of Maddie to Peter Han for alternative medicine connections
5. Prototype Development: Beginning with specific cultural narrative pieces for Gary's speaking events

Long-term Collaboration Vision

The conversation established foundation for ongoing partnership spanning fashion design, educational innovation, international business development, and cultural bridge-building initiatives, with both participants demonstrating commitment to excellence and community-centered values.