NYC Loft Conversation - Gary, Ryan VanGundy, Asif Rahman

Date: May 31, 2025 Location: Ryan VanGundy's Bowery Loft, NYC (Windsor Hotel Building) Participants: Gary Sheng, Ryan VanGundy, Asif Rahman, Alex Baydar (brief appearance)

Executive Summary

Gary visited Ryan VanGundy's extraordinary artist loft in NYC's Bowery district, meeting Asif Rahman (Head of PE at Brex) and experiencing one of the most unique living situations in Manhattan. The conversation covered Gary's education consulting work, current business challenges, and revealed an exceptional venue opportunity through Ryan's artist-protected loft space.

Key Revelations & Business Insights

Gary's Current Situation

Gary provided candid updates on his professional status and frustrations:

"I'm consulting this ed-tech billionaire. He has something pretty cool going in Austin... But I basically told him, you're not ready to scale. This is not good enough. And he's getting pissed at me for just telling the truth."

• Earning $600k/year consulting for Austin-based billionaire on K-12 education
• Billionaire refuses to give equity despite 36-year track record
• Gary considering building competing education system
• Described dynamic: "They can't take feedback. They've never spent any time with anyone that doesn't just bow down to them"

Leverage & International Opportunities

Gary revealed the scale of his current influence and options:

"I have like the president of Liberia hitting me up. I have literally China hitting me up, and I'm like, bro, if the US doesn't want to like level up, I'll fucking help make China 2.0."

• Working with Trump's pastor (White House faith office director)
• Was in White House two weeks prior to conversation
• Met with Bo Hines (David Sachs' deputy) about various initiatives
• Positioning as "billionaire whisperer" - advising out-of-touch wealthy clients

Education System Critique

Gary delivered scathing assessment of American education:

"The quickest way I could put the American school system is like you're, we're paying exorbitant taxes to ruin our kids. It's basically daycare except way worse because if it was just daycare, it'll be okay... We're actually miseducating our kids and making them hate learning."

Ryan VanGundy's Extraordinary Living Situation

The Artist Loft

Ryan's living arrangement represents one of NYC's most unique residential situations:

• Lives with Carmen Cicero (98-year-old abstract impressionist) and wife Mary (75)
• Protected by NYC "Loft Law" - pays ~$3,500/month split rent in Bowery
• Carmen still actively painting, recent work sold for ~$100k
• Building owner is Carmen himself - Ryan expects to potentially inherit

The Space & Opportunities

The loft offers exceptional event hosting potential:

"This is like an A-plus rooftop... No way! Bro, that's a steal. That is a steal." - Gary's reaction to the rooftop

• Private rooftop access in heart of Bowery
• Full artist loft with chess area, stained glass, kitchen
• Previous use as art gallery space
• Structural limitations on rooftop but main space perfect for exclusive events

Carmen Cicero Relationship

Ryan's relationship with the 98-year-old artist provides unique cultural insight:

"They're my second family... We chuckle about the fact that he's like, It's like a funny thing when you're 98 years old, you wouldn't be thinking about making money. He's still thinking about making money at 98."

• Regular dinners, Cape Cod summers, intellectual discussions until midnight
• Carmen reads 5 newspapers across political spectrum for balanced perspective
• Art market dynamics: galleries targeting aging artists for post-death value increase

Asif Rahman - Brex Private Equity Head

Professional Position

Asif provided insights into major fintech operations:

• 3 weeks into role as Head of Private Equity at Brex
• Company stats: 1,000 employees, $500M revenue, $10B valuation (believes real value ~$5B)
• Employee breakdown: 40% engineers, 30% sales, 30% other
• Planning IPO rather than acquisition (too big to be acquired)

Strategic Vision

Asif outlined ambitious expansion plans:

"Once you successfully do your thing at Brex... You'll literally just print fucking cash forever."

• Sees opportunity to become "private equity as a service" for major tech companies
• Targeting Stripe, OpenAI, other high-growth companies
• Recognizes brand importance: "People know what Brex is in tech"

Technology & AI Insights

Cursor vs. Windsurf Competition

Gary revealed inside access to cutting-edge AI development tools:

"I literally know the heads of product of both Windsurf and Cursor. It's like pretty funny to be so at the edge of things."

• Active advisor to both major AI coding platforms
• Filed numerous bugs during development phases
• Positioned at forefront of AI-powered development tools

"Everything is Broken" Philosophy

Both Gary and Ryan shared frustration with technological systems:

Ryan: "Everything is broken. I spent my morning, like, sitting over this, like, smart scale, trying to get it connected so I could just, like, weigh myself. And I was like, literally, it was an hour and 15 minutes."**

Gary: "I'm so glad that I'm not the only one that fucking thinks that, bro."**

Life Philosophy & Relationships

Quality vs. Quantity in Relationships

Gary articulated evolved approach to friendships:

"Why the fuck would I want a drinking buddy? Why would you want a drinking buddy? Totally. And there's so many people in the world, why not be friends with people you can do cool shit with, right?"

Ryan's "20 Summers" Vision

Ryan shared inspiring life philosophy learned from Carmen:

"My dream... is like, I mean, it's kind of what they want to do, but I could have just done this whole, like, 20 summers thing... 20 summers of, like, sitting around a little bonfire, having good wine, making good food, grilling out, going on walks through nature... that's just like, that is the good life to me."

Cultural & Social Observations

NYC Gentrification Dynamics

Ryan provided insider perspective on Bowery transformation:

"This whole bowery was known for homeless people. That's where the artists came. And then they made it cool... The reason that it's the valuation is what it is is because of these artists, right?"

Art as Investment Vehicle

Discussion revealed sophisticated understanding of art market manipulation:

"You have these galleries that then are specifically showing the works... they flock whenever the artists are about to die or towards the end of their life... because once that artist goes, the value goes up."

Business Opportunities Identified

Venue Hosting Potential

Multiple participants recognized Ryan's space as exceptional business opportunity:

• Photo shoots: $50-100/hour potential
• Exclusive album release parties
• Vinyl listening experiences
• High-end intimate events leveraging unique character

Education Vision Fund Concept

Gary seeded potential collaboration with Asif:

"Bill Ackman is really passionate about education, and I think there needs to be like an education vision fund... It's a lot easier to buy like a system that has a hundred schools, like buildings, than like, find the real estate, try to figure out how to make it good for school."

International & Civilizational Scale Thinking

Dubai vs. Detroit Framework

Gary articulated binary future for American cities:

"They know that you either become Detroit or you become Dubai, right? It's like Detroit or Dubai. And so you have to pay up for the people that know how to do that, right?"

• Saudi Arabia positioning for post-oil relevance
• Orange County seeking to reinvent itself
• Civilizational-scale opportunities for strategic thinkers

Personal Updates

Gary's Dating Life

• Most serious prospect: Aziah Buckner, daughter of Milwaukee Bucks assistant coach
• Name means "gift of God" in Hebrew
• Planning sushi dinner during NYC visit

Ryan's Life Transitions

• Recently stopped daily marijuana use to refocus
• Completed major open source project milestone
• Planning Spain trip
• Seeking new roommate as Roberto departing

Alex Baydar Brief Appearance

• Building systems integration business success
• Recent $15k direct contractor payment milestone
• Potential collaboration on venue infrastructure needs

Key Quotes

On American Education:

"We've optimized for a society of talkers who have outsourced all industrial capacity overseas. Your great-great-grandfathers built the world's leading infrastructure. Now we have poorly designed cities, shoddy architecture, shoddy infrastructure, shoddy construction, shoddy software." - Gary

On Quality and Craft:

"When we think about the range of quality in the United States, it's this. The full range of quality in Japan starts here." - Ryan on Japanese craftsmanship standards

On Entrepreneurial Reality:

"Basically everyone's forced to be an entrepreneur now. Because everything's changing so fast, like, even if you wanted to be an employee at a company, your company might be fucked if your CEO is not super, super entrepreneurial." - Gary

On Living Well:

"Take everything in. Take it all in. You know, like, enjoy it. Like, actually enjoy the fruits of your labor. You know, you gotta stop and smell the roses... until you kind of meet somebody like that who really shows you how that's done." - Ryan on lessons from Carmen

Strategic Implications

This conversation revealed several high-value opportunities:

1. Unique Venue Access: Ryan's loft represents rare NYC event hosting opportunity
2. Fintech Network Entry: Asif provides access to Brex network and PE expertise
3. Education Reform Leverage: Gary's frustrations could drive independent education initiatives
4. International Positioning: Gary's global connections offer alternative pathways
5. Cultural Bridge: Ryan's artist relationships provide authentic NYC cultural access

The intersection of Gary's strategic consulting capabilities, Ryan's unique living situation, and Asif's financial industry position creates multiple collaboration possibilities across events, education, and investment sectors.