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Jack Oremus

Basic Info​

  • Role: Guide at Alpha School (Austin).
  • Location: Austin, TX.
  • White guy. Has 100k followers online.
  • From Chicago area (western suburbs near Brookfield, ~25 minutes outside the city)
  • Moved to Austin around January 2025
  • Previously lived in the Old Market District of Chicago
  • Age: 28 (as of April 2025)
  • Getting married in August 2025
  • Has a girlfriend he frequently mentions communicating openly with

Professional Background​

  • Previously worked in social media management and content creation for tech startups and YouTubers
  • Grew up playing baseball and has an interest in the Chicago White Sox
  • Has been at Alpha School for a few months (as of April 2025)

Responsibilities & Insights​

  • Works alongside Garrett, primarily with high school and middle school students.
  • Familiar with Alpha School structure, levels, and the 2+6 model.
  • Understands the importance of Masterpiece projects.
  • Highlights the entrepreneurial background of many guides (e.g., starting businesses, social media presence).
  • Explains use of different campus spaces (HS section, MS section, stage area, tutoring rooms, podcast studio).
  • Aware of the network effect and resource sharing across the Alpha School system.
  • Facilitates connections between students and resources/people.
  • Involved with initiating the UT Plan II Vibe Marketing Initiative, connecting with Douglas Green and the Plan II program.
  • Interested in developing Alpha School's media presence, potentially through a reality show or in-house media support.
  • Coordinates with Shoss (Speech & Debate guide) regarding student presentations/communication.
  • Familiar with internal communication challenges and the need for better strategy/coordination in marketing efforts.
  • Brainstorming and potentially co-leading a "Gauntlet for Growth" program, analogous to the Gauntlet AI dev program but focused on marketing, sales, distribution, and other non-coding growth skills.
  • Reports to Steph Baduria (Director of K-8).

Philosophy on Education​

  • Believes AI should handle the core academic subjects where it excels
  • Sees the role of guides as motivating students and helping them see their potential
  • Values student autonomy and personalized learning approaches
  • Appreciates Alpha's model for allowing students to pursue their interests
  • Believes in the power of reading books as a foundational learning approach
  • Has a goddaughter (turning 10 in 2025) and several young second cousins, which has influenced his interest in education

Interactions​

  • 2025-04-08 (approx): Co-led a tour of the Alpha School Austin facility for Gary Sheng. Answered questions and provided context on the school environment, guide roles, and student projects.
  • 2025-04-09: Met with Gary Sheng, Douglas Green, John Alznauer, and Cruce Saunders. Discussed the UT Plan II vibe marketing initiative, reality show concept, AI-generated media, and potential marketing strategies for Alpha School.
  • 2025-04-09 (Later): Met with Gary Sheng to brainstorm a potential "Gauntlet for Growth" program, discussing its structure, rationale, potential leadership (Joe vs. Austin Allred), integration with Gauntlet Dev, and leveraging the Alpha network for guest speakers/resources.
  • 2025-05-09 (Super Builders Meeting with Stefanie Baduria):
    • Participated in the meeting.
    • Mentioned that for their one-on-one check-ins, they record them, get transcripts, upload to a custom GPT for QC based on handling emotions, goal setting, and addressing challenges.
    • Suggested incorporating these transcripts to train custom avatar students for guide training, fitting with Heather Staker's work and simulating student interactions.
    • Highlighted access to a "treasure trove" of data (transcripts/recordings of guide meetings) for training AIs.
    • Asked Stefanie Baduria for her top three app wish list items if Super Builders were to focus their interest.
    • Suggested that if there are FAQs Stefanie gets, they could be used to train the "Stef bot."
    • Mentioned he and Garrett are tag-teaming creating student profiles to help new guides get up to speed quickly (within 48 hours to a week) to establish trust and organic connections.
    • Mentioned talking to Tim Joo about a master spreadsheet of who owns what initiatives at Alpha and suggested centralizing this information would be helpful.
    • Proposed a weekly cadence for people with visibility into Alpha School tech needs to sync with Dallas Klein to relay priorities to Gauntleteers.

Transcripts​

Transcript IDDateSummary
2025-05-09-superbuilders-stefanie-baduria-school-expansion2025-05-09Super Builders meeting with Stefanie Baduria discussing tech needs and school expansion opportunities
2025-04-19-phone-call-keyen-gupta2025-04-19Phone Call with Keyen Gupta: Masterpiece Pivot & Networking Opportunities
2025-04-14-alpha-marketing-meeting2025-04-14Alpha marketing strategy meeting with Peter Han, Doug Green, and Kelly Davis
2025-04-09-gauntlet-for-growth-brainstorm2025-04-09Brainstorming session on developing a growth marketing program analogous to Gauntlet AI
2025-04-09-marketing-media-meeting2025-04-09Meeting on Alpha marketing, media initiatives, and UT Plan II vibe marketing internship program
2025-04-08-alpha-school-scaling-discussion2025-04-08Discussion on scaling Alpha School through reality shows, hackathons and organizational improvements
2025-04-08-alpha-school-strategy-meeting-tour2025-04-08Strategic discussions with Joe Liemandt, Mike Maples Jr. and team on AI concepts and platform development