Gary Sheng & Laura Li IMSA Reconnection - June 14, 2025

Meeting Context

Participants: Gary Sheng, Laura Li
Location: Coffee shop in Austin, Texas
Duration: Extended catch-up conversation
Background: Reconnecting after ~8 years; both IMSA alumni, Laura learned Gary was in Austin through their parents' connection

Key Topics Discussed

Gary's Austin Transition

Duration & Location: Gary has been in Austin for almost 5 months, previously spent 7 years in New York with extensive travel in 2023-2024.

Living Situation: Gary doesn't have a car and isn't compelled to get one, embracing walkable lifestyle near downtown/riverwalk area.

Work at Alpha Schools:

"I got a job at this like AI first K-12, so the first two hours of the day there's like a personalized AI tutor type thing that gets you through the common core curriculum in just like the first two hours of the day, and then it's like Montessori, kind of like free flow."

Laura's Austin Life

Professional Role: Works at Apple in Austin doing QA on their website, focusing on editing/UX content rather than pure writing. Works in the Apple building on Brady Street, 3 days per week in office.

Personal Life: Married to PJ, who is a competitive swimmer (father of 3 competitive swimmers). They live in the Domain area, about 5 minutes from the Domain shopping center.

Living Situation: Lives in area that used to be IBM campus, enjoys access to amenities like dog park. Has a dog and cat, recently started volunteering at pet shelter.

Family Updates & Generational Patterns

Laura's Brother Larry: Currently in Thailand working in e-commerce, nomadic lifestyle, doesn't engage much with Thai culture.

Parents: Both sets of parents are retired, minimal pressure regarding marriage/children.

Generational Observations:

"Our generation, no one's having kids... If you're having kids, you're waiting until literally the last minute."

College Friends & Life Paths

Laura's College Experience: Attended college in Missouri, most friends stayed there with traditional lifestyles (married, 3-4 kids). Maintains closer connections with high school (IMSA) and New York friends.

Social Connections: Laura's Austin friend group primarily consists of work colleagues, hasn't replicated New York social dynamics.

Gary's Professional Evolution

Recent Background: Did events globally for 1.5 years (tech, crypto, AI events), including a 2-month co-living experiment. Previously ran nonprofit for youth leadership, worked at Google before that.

Current Focus: Part-time business development for Alpha Schools, met his cohort through AI coding bootcamp (January-March). Has both "nerdy tech friends" and artist community connections.

Educational Vision:

"There's a broader recognition that the way that we were taught was like quite awful. So there's a lot more appetite than I think there was even two years ago."

About Alpha Schools scale: "There's about probably 150 kids in Austin... spread out across a few different campuses."

IMSA Network Connections

Mutual Friend: Laura mentioned another IMSA alum (year younger than Gary) who works at Apple in Austin and is single.

Network Nostalgia: Discussion about post-IMSA dating patterns and how alumni connected after graduation.

Random IMSA Encounter: Laura follows a skincare influencer who randomly mentioned attending IMSA in the 1990s when the school was first built.

Marriage & Life Philosophy Discussion

Gary's Perspective on Commitment: Shared concerns about divorce rates among mentor figures in their 40s-50s, all "great guys" but divorced/divorcing.

Dating Market Analysis:

"I think basically everyone's been told and or convinced themselves that like more or less being independent is like the right thing... people are pretty afraid of like commitment slash don't want to be overly dependent on other people."

Gary's Strategy: "My strategy if you want to call it that is just to not have too many expectations. I'm also not in the biggest rush."

Geographic Transitions & Lifestyle Preferences

New York vs Austin: Both appreciate Austin's more relaxed pace compared to New York's transactional, fast-moving environment.

Lifestyle Differences: Laura works reasonable hours except during product launches, enjoys 9am wake-up vs PJ's 6am swim schedule.

Social Media Usage: Laura primarily uses Facebook, not Instagram - part of broader generational shift away from posting.

International Opportunities

China Education Project: Gary mentioned meeting with Chinese education leaders interested in evolving their education system, potential for Gary to spend time in China.

Alpha Schools Executive: Gary noted an Alpha Schools executive who also attended IMSA, 10 years before Gary.

Key Quotes & Insights

On Austin's Appeal:

"I think this is my favorite city I've lived in." - Gary

On Educational Innovation:

"I don't think that we're preparing kids for our crazy time." - Gary

On Work-Life Balance:

"Would you be so busy?" - Laura, questioning the need to stay constantly busy in retirement

On Generational Changes:

"When you get like 27. I'm like way past that." - Gary, on traditional marriage timelines

Network Connections Established

• Reconnection between IMSA alumni after 8+ years
• Bridge between Gary's Illinois roots and Austin present
• Potential introduction to mutual IMSA friend at Apple
• Parents' networks maintaining connection across generations

Follow-up Actions

• Laura expressed interest in staying connected now that both are in Austin
• Discussion of mutual friend introduction possibility
• General commitment to maintain connection after successful reconnection

Strategic Insights

This conversation represents Gary's ongoing integration into Austin's social and professional ecosystem through multiple network layers: childhood/educational connections, tech industry relationships, and geographic community building. Laura's successful 5-year Austin integration provides a model for building sustainable life in the city while maintaining connections to previous chapters.

The discussion reveals generational shifts in life timeline expectations and the value of maintaining loose ties that can be reactivated when geographic proximity creates new opportunities for connection.