Strategic Transition: Alpha Organizational Challenges and Opportunity Development

Date: June 8, 2025
Location: Austin, TX (Gary's apartment pool)
Format: Strategic planning conversation

Executive Summary

A comprehensive strategic discussion between Gary Sheng and Tim Joo covering Tim's transition within Alpha School organization, the development of premium sports academy opportunities with Pat Azzi, and strategic approaches to building leverage through relationship-dependent deal flow. The conversation revealed significant organizational dysfunction at Alpha while identifying pathways to independent contractor arrangements and high-value educational market opportunities.

Current Organizational Challenges at Alpha School

WorkSmart System Constraints

Tim expressed frustration with micromanagement and intellectual property restrictions: Quote: "I can't be micromanaged like that. There's also intellectual property things that's also pretty big for me. I basically want to have a completely different contract than the one that I have right now, soon."

Leadership Dynamics and Hierarchy Issues

Discussion revealed dysfunction between different organizational layers:

• Jonathan Stewart representing traditional organizational hierarchy
• Joe Liemandt focused primarily on revenue generation
• Pat Azzi receiving direct access despite being new and remote
• Arthur representing "minions" within existing power structure

Key Insight from Tim: "Joe cares about money. So if you're bringing deals in man, and the deal is contingent on your relationship with people... then you're incredibly more valuable than someone who has experience but still has to do 12 to 18 months of trust building."

Pat Azzi Sports Academy Collaboration

Orange County Volleyball Academy Project

Tim detailed his collaboration with Pat Azzi on premium sports academy development:

• Partnership with Ashley Maldonado: Professional volleyball coach with multi-million dollar business
• Premium Market: $50K/year academy targeting wealthy Orange County families
• Proven Track Record: Ashley consistently places athletes at Oregon, Pepperdine, Stanford
• Leadership Engagement: Joe Liemandt and Niraj providing direct support with 20+ email exchanges

Quote from Tim: "Pat's been on the job for one month, and he's got [Niraj] and Joe emailing him back and forth... It goes back like 20 emails. So it's like, you're literally cutting out all the bullshit."

Strategic Differentiation from Texas Sports Academy

Tim explained the premium positioning approach: Quote: "The strategy with Texas Sports Academy has been wrong from the beginning, which is you need to hyper-focus on one successful, super successful coach, right? Not fucking A, kumbaya, basketball, football, tennis, whatever you like, right?"

Market Validation: "Joe's really unhappy with Texas Sports Academy, Jamal, because their kids perform shit. On academics, yeah. So it's defeating the purpose of the whole thing."

Strategic Transition Philosophy

"Going Slow to Go Fast" Approach

Tim outlined tactical patience for strategic advantage: Quote: "My strategy is like yours, all offense, right? But tactically, I think sometimes it's viable to play defense or play dumb or defer to the existing structures, if it's all in respect to the longer term, being on offense all the time, right?"

Implementation Strategy: "If we humble ourselves to play their game for however long we can tolerate while pushing the ball forward, boom, boom, boom, constantly, then eventually we'll get to a point where it's like, dude, I have more leverage and authority than I had three months ago."

Working Within Power Structures

Tim recognized the futility of fighting existing organizational dynamics: Quote: "Going against the existing power structure, it doesn't make any sense. It's fruitless because these people, all that they have dreamed of is being part of a power structure... versus helping kids or whatever, right?"

Gary's Strategic Opportunities

Jewish Schools Initiative

Gary mentioned pursuing opportunities in New York: Quote: "There's a there's a possible opportunity to integrate to our learning and to Jewish schools that are being threatened to shut down."

Tim's encouragement for independent positioning: Quote: "If you open up that business line, Gary, that's your slice of your own. It's just like free money. And no, not even just free money, it's also control. Being able to implement your team, how you want to operate, right?"

Commission-Based Deal Flow Model

Discussion of transitioning to independent contractor status: Quote from Gary: "What I would want to do is basically see if I can close one or both of two deals that I am sourcing for Alpha, that I just become someone that takes commission on deals."

Relationship Leverage Strategy

Trust-Building as Competitive Advantage

Tim emphasized the business value of established relationships: Quote: "Building schools is incredibly hard because it's a trust business and typically trust takes months to build, right? But if you come in and you're able to hijack that trust building to a period of less than a month or three weeks and get shit rolling, which I know you can do, then you're incredibly more valuable."

Personal Network Monetization

Tim outlined his extensive faith-based network access: Quote: "I have like different Baptist denominations that are just like, maybe like, you know, a few thousand people, right? That are just like, I have a chokehold on... Or like, you know, getting very tapped into LDS... One of my friend mentor type people, she's part of the, one of the disciples of Joseph Smith, right? The prophet of Mormon Church."

Business Model Evolution Discussion

Brand Over Company Focus

Tim's insight on changing business landscape: Quote: "Super builders is that Like, they're starting to realize too, they're not in the organization to build apps. They're there to build, and not even to build companies anymore, man. We're here to build brands."

Strategic Rationale: "In the new age, when you can literally build software and clone software like that, the only moat that you really have is your brand, the narrative that your brand operates in, and the internal and the external stories."

Relationship-Dependent Business Development

Tim's core value proposition: Quote: "I'm a relationship guy. If they fuck with me, that whole line is dead. That's how you get leverage, right?"

Personal and Professional Boundaries

Managing Inbound Demands

Gary shared his approach to managing requests: Quote: "Part of why I stopped tweeting dude is because... I just don't need more inbound, right? I just don't need like, anytime someone texts me, what are you up to? I don't feel obligated to like, actually give them the full answer."

Professional Distance Strategy

Tim's realization about relationship management: Quote: "I don't owe anyone anything. Even your friends, right? Because it's like, I've been taken advantage of by people who I've considered friends and brothers that I've had to cut out of my life because I realize they're just motherfucking takers."

Educational Vision and Standards

Human Flourishing as North Star

Gary's philosophical approach to educational success: Quote: "I always go back to human flourishing and it's like there's an open question of how do you measure all this stuff? But, right, it's such a good North Star because you can tell if a kid is like on the path to success, right?"

Long-term Educational Impact

Gary's vision for Alpha alumni significance: Quote: "I think alpha really is solidified itself as an educational system, when being an alpha alumni means something, right? That's the long goal... when we get to that point, that's when I've known that alpha has succeeded as a new educational system."

Organizational Insights and Warnings

Leadership Accessibility Patterns

Tim's observation about organizational dynamics: Quote: "Despite being new and remote, [Pat] has more direct access to leadership than many on-site team members. His success represents validation that Alpha leadership values results over politics."

Revenue-First Leadership Philosophy

Tim's assessment of Joe Liemandt's priorities: Quote: "Ash has told me multiple times now and he was like, the only thing Joe cares about is money. Right? He's told me that. So if you're bringing deals in man, and the deal is contingent on your relationship with people... then you're incredibly more valuable."

Strategic Recommendations and Next Steps

For Tim's Positioning

1. Collaboration with Pat: "I would just make sure that the brain lift is now authored by you. No, by you and Pat."
2. Leverage Protection: Use relationship dependency to ensure organizational respect
3. Commission Structure: Transition to deal-flow based compensation model

For Gary's Opportunities

1. Independent Business Line Development: Pursue Jewish schools as separate revenue stream
2. Commission-Based Partnerships: Structure deals to maintain relationship control
3. Strategic Patience: Allow organizational dynamics to settle before major moves

Key Insights on Modern Business Development

Network Effects in Education

Tim's understanding of relationship-driven business: Quote: "The only way to build a relationship is by sharing stories, right? And finding some sort of relation or common interest in what you're trying to build together, right?"

Brand Building in AI Era

Gary and Tim's vision for differentiation: Quote: "Faith, and education, and finding your way in an AI world... People are going to look at AI as gods. If they don't already, and they will. So it's like someone needs to be out there to put out a vision."

Conclusion and Future Collaboration

The conversation concluded with mutual recognition of complementary strengths and ongoing collaboration opportunities:

Tim's gratitude: "No matter what happens, dude, I'm always going to owe you big time for just showing me what it's like. What it even means to be razor focused and relentless about one goal in a period as small as four weeks."

Gary's strategic insight: "A big part of my role is to help people way smarter than me get focused. Yeah. That's it."

This conversation represents a maturation of both participants' understanding of organizational dynamics, relationship leverage, and strategic positioning within complex educational business environments. The discussion provides a roadmap for navigating institutional constraints while building independent value creation capabilities.