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2025-06-04-gary-sheng-jonathon-stewart-alpha-strategy-event-discussion
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Transcript Summary: Gary Sheng & Jonathon Stewart - Alpha Strategy & Event Discussion

Date: June 4, 2025 Participants: Gary Sheng, Jonathon Stewart (Alpha Schools Head of Engagement) Subject: Discussion on Gary's role, Alpha Schools' strategy, organizational dynamics, and planning for the June 14th "Alphas Activate" event.

1. Introduction & Context Setting

  • Jonathon Stewart (JS) is Head of Engagement at Alpha Schools, based in LA/Austin, reporting to Joe Liemandt and Mackenzie Price.
  • Gary Sheng (GS) recently joined Alpha (2 months ago) after the Gauntlet program, now focusing on events and understanding internal operations. GS background: Google, youth empowerment nonprofit.

2. Gary Sheng's Onboarding & Role Discussion

  • GS's Motivation: Passion for education reform, skill in gathering people for big missions. Initial discussions with Joe Liemandt involved creating a "Davos in America" with an education focus.
  • Gauntlet Program Experience: GS expressed concerns about the Gauntlet onboarding for ~70 people, feeling they lacked context and were pressured to develop "billion-dollar app ideas" rather than addressing immediate organizational needs. GS sees his event-focused role as an exception.

    GS: "It has been interesting to observe the kind of rapid onboarding of like 70 people that have not gotten I would say sufficient context to to to for sure add value."

  • Current Focus (GS):
    • Organizing the June 14th "Alphas Activate" event.
    • Trying to navigate internal siloes and improve coordination.
    • Desire to improve new hire orientation.
  • Event Philosophy (GS): Prefers fewer, more exciting and mobilizing events over frequent, less impactful info sessions. Sees the June 14th event as a learning opportunity.
  • Long-term Vision (GS): Interested in "movement building" for Alpha, reaching beyond immediate parent enrollment to legislators, journalists, etc., to create systemic change.

    GS: "We should never let the next Steve Jobs isn't Andy Warhol's and Ramanujan's... be stuck in an environment that doesn't respect their... gifts."

3. Jonathon Stewart's Perspective on Alpha's Strategy & Operations

  • JS's Mandate:
    • Unify Alpha's messaging ("Right now it's a mess... people make up shit.").
    • Fix info sessions (designing new 22-min presentation).
    • Event strategy oversight.
    • Bottom line: "enrolling kids in the schools."
  • Interpreting Joe Liemandt's Vision: JS affirmed GS's interpretation that Joe's ambitious numbers (1200 Texas schools, 2.5 billion kids impacted) are serious strategic goals.

    JS: "Joe is not speaking hyperbolically. Joe is definitely speaking from a billionaire visionary standpoint."

  • 1200 Texas Schools Initiative: JS explained this is tied to influencing Texas school choice legislation by aiming to place an Alpha presence (e.g., Texas Sports Academy - TSA) in each of the ~1200 school districts. Joe has reportedly spoken with the Texas Governor about this.

    JS: "If we can set up a school there in... every school district across the state then all of a sudden that changes the political calculus for the laws."

  • "Two-Hour Learning" / "Time Back" Model: JS described this as Alpha's "Intel chip," with multiple distribution channels:
    • New Alpha schools in 25 cities.
    • TSAs in Texas.
    • Partnerships with non-Alpha private/public schools.
    • Alpha Anywhere (homeschooling).
    • Gauntlet program apps.
  • Organizational Dynamics: JS acknowledged siloing and dysfunction, some perceived as intentional. Advised flexibility.

    JS: "I have to believe that some of that siloing is by design... My brain is always trying to... put all this into some sort of... smarter tighter organization form... but I think for me it's been more helpful to say where can I be flexible..."

  • JS's Internal Sharing: Emphasized that his detailed strategic explanations to GS were "internal... raw hot take, not something that I would say publicly."

4. June 14th "Alphas Activate" Event - Planning & Concerns

  • Event Background (GS): Evolved from a push by Finance/Ops (Arthur approved) for a quick follow-up event after a successful one in late April. GS is trying to make the best of the situation and avoid Alpha looking "flaky" by cancelling.
  • GS's Goals for the Event:
    • Learn and iterate on event models.
    • Provide a platform for key connections:
      • Lyle (Lael Alexander) to showcase tech (micro schoolhouses, smart campus tech) and meet Alpha leadership.
      • "Alex Ed" group (Sherman & Ari Crane), consultants with Asian governments, to meet Alpha leadership and discuss partnerships.
  • JS's Concerns:
    • Audience & Attendance: Questioned the strategy of relying on current Alpha parents to invite friends for a summer event, citing event fatigue and the difficulty of filling rooms. Worried about low turnout (fewer than 10 attendees).

      JS: "If your plan is to say let's send this out to existing families and have them invite people and count on that as filling the room. I think you could end up with less than 10 attendees."

    • Clarity of Purpose: Wanted more clarity on "what do I get as an attendee?" beyond vague notions of "future of education."
    • Resource Protection: Stressed he "can't put Mackenzie in front of a room of 10 people."
  • Proposed Solutions & Next Steps:
    • JS offered to give his new 22-minute presentation if Mackenzie Price attends.
    • JS and Mackenzie to coordinate their involvement.
    • GS to provide JS with one-liners on Lyle and Alex Ed for context.
    • Agreement to centralize communication regarding event logistics and run-of-show.
    • JS to connect with Mackenzie and get back to GS by end of day.

5. Alpha's Broader Challenges & Opportunities

  • Onboarding: GS highlighted issues with the Gauntlet onboarding; JS acknowledged the general roughness.
  • Internal Coordination: Both acknowledged communication gaps and siloes.
  • Scaling: GS concerned about pressure for rapid, potentially unsustainable scaling (e.g., Joe's 1200 schools in 13-14 months) versus responsible, quality-focused growth.

    GS: "What we run the risk of... is creating an unnecessary bubble that could pop because we have such great marketing..."

  • International Interest: Mackenzie's videos are viral in China (with subtitles). Alex Ed group represents significant Asian market interest.
  • Event Strategy: JS stated events are a "terrible mess in general right now," and a senior events role is approved.

Key Takeaways

  • Significant alignment between GS and JS on the challenges and opportunities within Alpha.
  • JS provided crucial internal context on Alpha's high-level strategy and operational realities.
  • The June 14th event is a point of focus, with JS offering support conditional on clarity and leadership alignment, while GS aims to leverage it for key strategic introductions despite logistical challenges.
  • Both see value in improving internal processes (onboarding, communication, event planning) and messaging.