Skip to main content

Chris Tyrrell

Basic Info​

  • Location: Washington, DC area
  • Role/Occupation: Head of Digital Asset Risk, Citibank Services Division (as of Dec 2025)
  • Met: Vatican conference, November 2025
  • Background: Finance/fintech/crypto executive and lawyer

Professional Background​

  • Current: Running digital asset risk for Citibank's services division - described as "dream job" perfectly matching his resume
  • Previous roles:
    • Senior Advisor to Chief Compliance and Legal Officers at Blockchain.com (Americas compliance and sanctions)
    • Head of Digital Assets Compliance at Goldman Sachs (firmwide crypto/blockchain oversight)
    • Founder/CEO of OfferBoard (small-business capital formation platform)
    • Chair of CFIRA (crowdfunding trade body)
    • Started career in structured finance at Cadwalader law firm (NYC)
  • Expertise: Securities crowdfunding, digital assets, compliance, structured finance

Catholic Education Initiative​

Alpha Schools Pilot (Fall 2025)​

  • Ran one-semester pilot at a Catholic school (not his own parish/kids)
  • Cost: ~$20k per student (half Alpha, half other costs) vs. typical $9k +/- $3k Catholic school tuition
  • Funding: Privately subsidized by donor investors wanting to create something useful for Catholic schools
  • Timeline: Found opportunity April, found parents May, convinced them June, got commitments August, launched September

Key Learnings from Pilot​

  • "Learned enough that if we had to do it from scratch, we would do it from scratch"
  • Two Hour Learning priced at about Texas voucher price - can't use Alpha for TEFA-funded schools
  • Quality issues with Alpha product: basic QA failures (answers don't show up, character limits too short, misspellings, questions don't match text)
  • Board member (software PM): "I would never let this product get to UAT"
  • Alpha's modules not standardized - some hours long, some minutes, not the claimed "25-minute modules"
  • Alpha's pedagogy: extrinsic motivation, Common Core curriculum, optimizing for MAP testing speed
  • "Imago Joe" observation: Alpha built in Joe Liemandt's image - competitive, money-focused, beat-the-system mentality

Vision for Classical Catholic AI Education​

  • Goal: Not to make money but to scale Catholic/classical education cheaply
  • Philosophy: Intrinsic motivation, orienting students toward truth and knowledge acquisition
  • Target pricing: Texas and Florida voucher prices (~$10k)
  • Opportunity: New rural schools with state money, religiously affiliated, AI-enabled with low faculty cost
  • Considering leveraging existing classical pedagogy work (CLT, Colby Academy, Seton)

Technical Architecture Ideas​

  • Met people in Rome building single-purpose interpretive layers on multiple LLMs
  • Three-layer model: LLM base → interpretive layer (rules) → Persona layer (tutor)
  • Idea: Collectively-used interpretive layer with different tutor models built on top
  • Gary's suggestion: "Linux of adaptive AI tutor" - open source standard for the middle layer

Next Steps (as of Dec 2025)​

  • Board meeting just happened - working theories on what's next
  • Planning investor conversations over next few weeks
  • Will have conversation with Joe Liemandt about forking or building fresh
  • Expects Joe will say no; preparing to raise money to build from scratch
  • Target: Fraction of a product by September 2025 that can go alongside existing platform
  • Scheduled follow-up call with Gary in one week

Personal Details​

  • Parents in DC
  • Has multiple kids
  • Uses Read AI for meeting transcription/CRM
  • Values data sovereignty despite using big tech tools
  • Candid communication style, willing to be direct about concerns

Key Quotes​

  • On Alpha: "The quality level of the product itself is not hard to compete with"
  • On Joe: "It's imago Joe... It's in Persona, Joe"
  • On mission: "I don't have any ambition to make my money this way... I just want it to exist"
  • On AI models: "The biggest flaw in all the AI models is that they're building for adherence, not for truth"
  • On school choice: "I think you could put a school in a box with very low faculty cost and modest facilities"

Strategic Value & Collaboration Areas​

  • Shared vision: Kingdom-focused education that scales cheaply
  • Complementary skills: Finance/compliance expertise + Catholic education passion
  • Network: Investor relationships, Vatican connections, classical education community
  • Potential collaboration: Building open-source classical Catholic AI tutor platform

Transcripts​

Transcript IDDateSummary
2025-12-30-gary-chris-tyrrell-catholic-ai-education-strategy2025-12-30Alpha pilot reflections, classical Catholic AI tutor vision, "Linux of adaptive AI" concept, Citibank job announcement, planning fresh build approach