CrossGen AI Learning Journey
LEARN · Intro Fundamentals ★ Entry 1
Intro Fundamentals (6 weeks · prerecorded)
▸Start here · self-paced · open to everyone
Week 1 · Foundations
How LLMs actually workLive · 60m
Vocab primerAsync · 30m
What AI is bad atLive · 60m
Your first real promptLab · 45m
Brief AI like a colleagueLive · 60m
When to use AI vs notLive · 45m
3 ways to improve any promptLab · 45m
Hallucinations: spotting themLive · 45m
Workspace setup (Claude + Desktop)Lab · 30m
Week 2 · Critical thinking
Bias awarenessLive · 60m
AI as thought partnerLive · 60m
Chat vs search vs assistantAsync · 30m
Reading AI output skepticallyLab · 45m
Work WITH AI vs work TO AIWorkshop
Citing sources (and verifying)Lab · 45m
Confidentiality: what to shareLive · 45m
AI for thinking (devil's advocate)Lab · 60m
"AI second opinion" habitWorkshop
I
Checkpoint I
Unlocks Weeks 3 and 4
▾Unlocked by completion of Checkpoint I
Week 3 · Daily habits
5-minute morning AI ritualLive · 30m
AI for inbox triageLab · 45m
AI for meeting prepLab · 45m
Meeting follow-up & actionsLab · 45m
AI for writing (draft/edit/proof)Workshop
AI for research (first pass)Lab · 45m
AI for explaining thingsLab · 30m
AI for decisions (brief the call)Workshop
"Five whys" with AILab · 45m
Week 4 · Patterns
Recurring task → reusable templateWorkshop
Zero/one/few-shot (no jargon)Live · 45m
Persona promptingLab · 45m
Reverse promptingLab · 30m
Prompt chainingWorkshop
Iterate vs start overLab · 30m
"Show me bad examples" trickAsync · 20m
"Draft a response" patternLab · 45m
"Rewrite in my voice" patternLab · 45m
II
Checkpoint II
Unlocks Weeks 5 and 6
▾Unlocked by completion of Checkpoint II
Week 5 · Tools & formats
Working with imagesLab · 45m
Working with documentsLab · 45m
Working with spreadsheetsLab · 45m
Voice-to-AILab · 30m
AI on your phoneAsync · 20m
"Simplify this" patternLab · 30m
"What am I missing" patternLab · 30m
"Make it shorter" patternLab · 30m
"Make this presentable" patternWorkshop
Week 6 · Habit & capstone
Comparing AI tools side-by-sideWorkshop
Your personal prompt libraryWorkshop
Team prompt vault (intro)Live · 45m
Context windows explainedAsync · 20m
Build your daily AI habitWorkshop
Better, not only fasterLive · 45m
The AI confidence trapLive · 30m
Recovering from a bad sessionLab · 30m
Explaining AI work to colleaguesWorkshop
Commitment: one weekly promptLive · 30m
Capstone: automate one taskCapstone · 90m
III
Checkpoint III
Fundamentals complete → T1
LEARN · T1 Cohort
T1 Cohort Cowork
Requires completion of Intro Fundamentals
Vocab & workflow audit
Shared vocab & mental modelLive · 90m
Workflow audit: where AI fitsWorkshop · 2hr
Claude Desktop + connector setupLab · 90m
Prompt library & cowork sprints
The shared prompt libraryWorkshop
Cowork sprints on live workflowsCowork · 6 sessions
Build-vs-buy: informed buyerWorkshop
Champion model & MCP literacy
The internal champion modelWorkshop · 2hr
MCP & connector literacyLive · 90m
ROI measurement & showcase
Measuring AI ROI at team levelWorkshop
Showcase + T2 project scopingLive · 2hr
✓
Cohort Badge
T1 complete
BUILD · T2 Project Build
T2 Project Build
Requires completion of T1 Cohort Cowork
Scope
ROI filter: pick the right first buildWorkshop · 2hr
Triggers, actions, data pipelinesLive · 90m
MCP servers & webhooks 101Lab · 2hr
Design
Build Your Own Task ManagerBuild · 4 sessions
Build Your Own CRMBuild · 4 sessions
Build
Custom agents: scope → build → deployBuild · 4 sessions
Human-in-the-loop workflowsWorkshop
Cost, latency & reliabilityLive · 90m
Ship
AI evaluations: testing outputsLab · 2hr
Showcase + handoff docsLive · 2hr
✓
Project Badge
T2 complete
ONGOING · T3 Partnership
T3 Ongoing Partnership
Requires completion of T2 Project Build
Onboard & integrate
Monthly "What's new in AI" briefingBriefing · monthly
Single agent strategyWorkshop
New hire AI onboardingOnboard · per-hire
Embedded buildout supportEmbedded · as-needed
Quarterly cadence
Multi-agent systemsWorkshop
Coordinated agents & orchestrationWorkshop
Quarterly skills-gap assessmentAssessment · quarterly
Risk & renewal
Risk & oversight (ongoing)Ongoing
Change mgmt: skeptic & overuserWorkshop
Annual AI strategy + budgetAnnual
✓
Partner Seal
T3 active
ONGOING · T4 Long-term Advisor
T4 Long-term Advisor
Requires completion of T3 Ongoing Partnership
Annual strategy
Annual strategy roadmap (board)Annual · board
Industry positioning: AI moatWorkshop
AI-native org design reviewAnnual
Founder strategy session w/ SeanAnnual · 1:1
Co-marketing
Case study + co-marketingProject
Early access to CrossGen pilotsOngoing
Mentor track: teach new cohortsPer-cohort
Peer network
Alumni roundtables (CEO/COO)Quarterly
Talent strategy: AI-augmented hiringWorkshop
M&A diligence: AI capabilities auditSituational
✓
3-Yr Seal
Long-term
Rank ladder · earned by submitting The Crossing (your shipped artifact)
★ INTRO · Open to Gen-0 · 5 paths
▸Open to Gen-0 · everyone
The CRIT Method · Engineering Your AI↳ Maps to W1-W2🔨 The Crossing: CRIT prompt library
AI as Your New Intern · The Manager Mindset↳ Maps to W1 mindset🔨 The Crossing: 10-case managed-AI log
Daily AI Habits↳ Maps to W1 mindset🔨 The Crossing: "My AI day" + 14-day log
Grounding AI in Your Own Files↳ Maps to W7🔨 The Crossing: 1-page cited briefing
AI for Writing & Editing↳ Maps to W2🔨 The Crossing: Before/after writing pack
★★ INTERMEDIATE · Requires Gen-1 · 8 paths
Requires Gen-1 · submit 3 Intro Crossings
Controlling Probability · Hallucinations & Context↳ Maps to W3 + Lesson 1🔨 The Crossing: 5 caught-and-fixed cases
Inbox & Email Automation↳ Maps to W8🔨 The Crossing: Inbox assistant + 2-wk log
Meetings & Notes Intelligence↳ Maps to W7-W8🔨 The Crossing: Workflow on 3 meetings
Claude Projects · Your Custom Assistant↳ Maps to W6-W7🔨 The Crossing: A Project + 5+ uses
Spreadsheets, Data & Analysis↳ Maps to W7🔨 The Crossing: Cleaned data + memo
Marketing & Content Workflows↳ Maps to W2-W6🔨 The Crossing: 1→4 content engine
Customer-Facing AI↳ Maps to W6-W8🔨 The Crossing: Live CX workflow
Skills Library · Reusable Workflows↳ Maps to W5🔨 The Crossing: 5+ Skills + usage log
Accidental Coding · Reading Code Without Fear↳ Maps to W10-W11🔨 The Crossing: Claude Code script
AI Security & Responsible Use↳ Maps to Lesson 1 + Ongoing🔨 The Crossing: AI use policy + audit
★★★ ADVANCED · Requires Gen-2 · 3 paths · ⚿ rank-gated
Requires Gen-2 · submit 4 Intermediate Crossings
Prompt Chaining & The Editor Pattern↳ Maps to W4🔨 The Crossing: Chain on 3 real tasks
Artifacts & Live Deliverables↳ Maps to W6🔨 The Crossing: 3 built artifacts
End-to-End Agentic Workflows in Claude↳ Maps to W9🔨 The Crossing: Verified agentic workflow
🎟 LIVE IN-PERSON EVENTS · unlocked free at rank
Build Your Own AI Daily Habit
Gen-1
Build Your Own Inbox Triage
Gen-2
Build Your Own Claude Project
Gen-2
Build Your Own CRM
Gen-3
Build Your Own Custom Agent
Gen-3
Co-host a Live Event with CrossGen
Gen-4
WHAT IT IS
NVIDIA Hardware systems for on-prem AI: private RAG, self-hosted agents, production deployment of what you built in CrossGen.
WHY IT MATTERS
Data sovereignty. Predictable cost at scale. Regulated industries. Speed without API limits.
WHO IT'S FOR
Independent learners ready to deploy locally, OR T3-T4 partners with sensitive workloads.
PAIRS WITH
Cards with the green-line accent on the left edge are Hardware-eligible: classes where Hardware changes what's possible, not only how.
Cards with the ◧ green edge across the other trees are Hardware-eligible. These are classes where Hardware changes what's possible, not only how.