01Executive Summary
A done-for-you, all-inclusive AI workshop retreat for 8–12 US-based small business owners and digital agency founders, hosted twice per year (Y1) at a private finca buyout in the Colombian Coffee Triangle. Greg and Jesse personally orchestrate every touchpoint — application, US airport-to-PEI airfare booking, ground transport, finca stay, chef-driven meals, curriculum, excursions, return travel.
"Don't learn AI — leave with your AI department deployed."
80% live build, 20% framework. Attendees go home with a deployed Astro site, a custom MCP server tied to their business data, a working voice agent on a live inbound number, and a SaaS-killer app that retires one paid subscription.
Y1 Revenue
$200K
2 cohorts · 20 seats
Y1 Net Profit
$102K
~$51K per host
Gross Margin
73.7%
Per cohort, mid-tier finca
Y3 Net Profit
$337K
~$169K per host
02Market & Competitive Landscape
Who's playing in the $5K–$15K AI retreat space
| Operator | Angle | Tier |
|---|---|---|
| Liam Ottley (Morningside AI) | AAA agency builders | $5K–$15K |
| Caleb Mast (AI Foundry) | Custom AI agent intensives | $10K+ |
| Greg Isenberg / Justin Welsh / Codie Sanchez | Founder masterminds, AI as primary topic | $10K–$30K |
| The Rundown / Marketing AI Institute | Boutique high-tier workshops | $5K–$15K |
$10K tier breakdown
| Tier | What you get | Format |
|---|---|---|
| $5K | Group lectures, standard hotel, info-heavy | Group workshop |
| $10K–$15K | Luxury villa, 1:1 tech support, peer networking | Implementation retreat |
| $25K+ | Custom dev, long-term consulting, equity plays | Partnership |
What kills $10K AI retreats
- Connectivity — bad WiFi destroys an AI workshop instantly.
- Skill mismatch — non-technical CEO + Python dev = group drags to the floor.
- Scope creep — covering "all of AI" instead of one defensible workflow.
- Refund risk — undefined deliverables → buyer's remorse.
- Wrong-fit attendees — degrades the cohort experience for everyone.
Why Colombia, not Bali
- Bali / Tulum: saturated, digital-nomad-coded → drags premium perception down.
- Colombia / Portugal / Mexico City: emerging alpha locations.
- Coffee Triangle specifically: EST/CST timezone alignment with US East Coast. Authentic. Premium fincas at half Tulum prices. "Ahead of the curve" positioning.
Cohort fit profile (enforced via application)
- US-based, English-speaking
- Owns or runs a service business or agency doing $250K–$5M/year
- Spending $2K–$15K/month on SaaS that could be replaced
- Mac with Apple Silicon (M2/M3, 16GB+ RAM) — required for local Ollama
- Claude Pro, VS Code, basic Git
- Brings a "dirty data dump" CSV from current tools
03Product: The Curriculum
Theme: The Ownership Intensive — stop renting $60K/year of SaaS, start owning a $600/year API stack.
5-Day schedule
| Day | Morning | Afternoon | Evening |
|---|---|---|---|
| 1 — Arrival | PEI pickup, finca check-in, welcome lunch | Environment audit (Claude Code, GitHub, Ollama install) | Welcome dinner + "State of the Stack" fireside |
| 2 — Logic Layer | MCP servers from scratch | Build: each attendee's own MCP server tied to their data | Coffee farm tour + sunset dinner |
| 3 — Growth Engine | AI SEO content pipelines | Voice agents (Vapi/Retell) on a real inbound number | Hot Seat mastermind (one bottleneck per attendee) |
| 4 — The Swap | Replacing a SaaS with FastAPI + Astro | Build: custom CRM / dashboard / quoting tool | Cocora Valley jeep + farewell dinner |
| 5 — Ship & Depart | Push-to-prod for everyone's builds | Final 1:1s, 90-day roadmap, alumni Slack onboarding | PEI drop-off |
Daily template
08:00 Breakfast + Daily Sprint preview 09:00 Module workshop (45 min live demo by Greg or Jesse) 09:45 Guided build (pair-programming with hosts) 13:00 Working lunch (focus: business logic application) 14:30 Deep work / implementation 17:00 Leisure / coffee farm / pool 19:00 Dinner + Hot Seat mastermind 21:00 Optional 1:1 with host
Deliverables — each attendee leaves with all 4
- Private MCP server wired to their business data
- Deployed Astro site with AI content hooks (live URL)
- Active voice agent on a real inbound phone number, qualifying leads
- Custom SaaS-killer app — functional internal tool replacing one paid subscription
Pre-retreat (14-day onboarding)
- Application + 30-min discovery call
- Tech audit Zoom — verify Mac specs, Claude Pro, GitHub, VS Code
- Pre-work: "dirty data dump" CSV export from existing tools
- Welcome kit shipped (notebook, swag, finca prep doc, packing list)
Post-retreat (90 days)
- Bi-weekly group office hours (Zoom)
- Private alumni Discord
- Recorded retreat sessions (private vault)
- Upsell: $30K/year Inner Circle mastermind — front-end → back-end profit play
04Venue & Logistics
Finca options (private group buyout, 10 attendees + 2 hosts)
| Property | Region | Buyout/night | Vibe | Notes |
|---|---|---|---|---|
| Hacienda Venecia | Manizales | $1,000–$1,800 | Authentic working coffee farm | Budget luxury |
| Hacienda San José | Pereira | $1,500–$2,200 | Historic 1888 estate | Y1 pick |
| Sazagua Hotel Boutique | Pereira | $2,500–$3,500 | Luxury / nature fusion | Premium, fiber WiFi |
| Hacienda Bambusa | Armenia | $3,000–$4,500 | Top-tier hacienda | Best-in-class brand |
Recommended Y1: Hacienda San José (mid-tier, $1,800/night). Balances margin against luxury promise. Sazagua as Y2 upgrade.
Connectivity (solved at the finca)
- Finca runs Starlink high-speed as the primary connection. No reliance on rural fiber stability.
- Mesh WiFi (TP-Link Deco / Eero) deployed across the property for 12 simultaneous users
- Backup: Claro 4G/LTE Colombian SIM hotspots per host
- Ollama running local on attendee Macs — most workshop builds work offline if Starlink ever blinks
Flights
- Direct US→PEI: American (MIA→PEI), Spirit (FLL→PEI)
- Connections: via BOG (Bogotá) or PTY (Panama) for non-Miami/FLL
- Economy round-trip: $550–$900 (budget $750 average)
- Premium economy: $1,100–$1,600 (offer as +$500 upsell)
- US passport: no visa, 90-day visa-free
- Best months: Jan–Mar or Jul–Aug (dry). Avoid Oct–Nov (heavy rain)
Ground transport & excursions
- Sprinter van (12-pax): $375/day with driver+fuel
- Airport transfers PEI ↔ finca: $80–$120 per van ($200 round-trip budget)
- Excursions: coffee masterclass at Hacienda Venecia, Cocora Valley wax palms via Willys jeep, Santa Rosa de Cabal hot springs (private night access), Salento + Filandia, garden-to-table dinner with live Tiple
Safety
- Coffee Triangle = functionally State Dept Level 2, well below Bogotá/Medellín
- Rural, tourism-dependent, conservative region
- Private transport at night, no walking rural roads after dark
- Insurance: event liability + attendee health/evacuation rider required
05Financial Model
Per-cohort COGS (mid-tier, Hacienda San José)
| Line Item | Amount | Math |
|---|---|---|
| Revenue | $100,000 | 10 × $10K |
| Finca (4 nights) | $7,200 | $1,800 × 4 |
| Chef | $3,300 | $55 × 12 pax × 5 days |
| Sprinter van | $1,875 | $375 × 5 |
| Airport transfers | $200 | 2 vans |
| Attendee flights | $7,500 | $750 × 10 |
| Host flights | $1,500 | $750 × 2 |
| Excursions | $1,800 | $150/pax × 12 |
| Stripe fees | $2,910 | 2.9% + $0.30 × 10 |
| Total COGS | $26,285 | |
| Gross Profit | $73,715 | 73.7% GM |
Per-cohort P&L by venue tier
| Line | Venecia (budget) | San José (mid) | Sazagua (premium) |
|---|---|---|---|
| Revenue | $100,000 | $100,000 | $100,000 |
| Finca cost | $6,000 | $7,200 | $12,000 |
| Other COGS | $19,085 | $19,085 | $19,085 |
| Gross Margin | $74,915 | $73,715 | $68,915 |
| GM % | 74.9% | 73.7% | 68.9% |
Annual OpEx (Year 1)
| Line | Amount | Notes |
|---|---|---|
| Marketing / CAC | $30,000 | $1,500 CAC × 20 seats |
| Software (CRM, email, scheduling) | $3,000 | Annual stack |
| Legal & insurance | $5,000 | Liability, event coverage |
| Accounting | $3,000 | Bookkeeping + tax |
| Website / branding | $2,000 | Hosting, design |
| Contingency | $2,000 | Buffer |
| Total OpEx | $45,000 |
Annual P&L Y1–Y3
| Line | Y1 (2 cohorts) | Y2 (4 cohorts) | Y3 (6 cohorts) |
|---|---|---|---|
| Seats sold | 20 | 40 | 60 |
| Revenue | $200,000 | $400,000 | $600,000 |
| COGS | $52,570 | $105,140 | $157,710 |
| Gross Profit | $147,430 | $294,860 | $442,290 |
| Total OpEx | $45,000 | $75,000 | $105,000 |
| Net Profit | $102,430 | $219,860 | $337,290 |
| Per-founder draw | $51,215 | $109,930 | $168,645 |
Sensitivity (per cohort)
| Scenario | Revenue | COGS | Gross Profit | Δ vs base |
|---|---|---|---|---|
| Base (10 seats, San José) | $100,000 | $26,285 | $73,715 | — |
| Down (6 seats sold) | $60,000 | $20,421 | $39,579 | -$34,136 |
| Up (12 seats + Sazagua) | $120,000 | $34,017 | $85,983 | +$12,268 |
| Shock: airfare +$300/seat | $100,000 | $29,285 | $70,715 | -$3,000 |
| Shock: finca +25% | $100,000 | $28,085 | $71,915 | -$1,800 |
Breakeven: ~3 seats cover variable COGS; ~7 seats cover cohort COGS + allocated annual OpEx. Above 7 = profit.
Cash flow timing
| Phase | Timing | Action | Impact |
|---|---|---|---|
| Booking | T-6mo | Collect 50% deposit | +$50,000 |
| Booking | T-6mo | Pay finca 50% deposit | -$3,600 |
| Pre-retreat | T-60d | Book flights (full) | -$9,000 |
| Pre-retreat | T-30d | Collect balance | +$50,000 |
| Pre-retreat | T-30d | Pay van/chef/excursions | -$7,175 |
| Retreat | During | Pay finca balance | -$3,600 |
| Post-retreat | T+3d | Stripe fees settled | -$2,910 |
Cash rule: hold 50% deposit in escrow / dedicated retreat account until cohort fills. Don't book flights until min 6 seats sold.
06Sales & Marketing
Funnel benchmarks
- Landing page visit → application: 3–5%
- Application → paid seat: 15–25% (with discovery call)
- Implied: 1 paying seat per 80–120 LP visits
Channels (ranked)
- X / Twitter — primary funnel for AI/founder audience
- LinkedIn — secondary, hits agency owners and SMB ops
- Podcast tour — pitch founder-audience shows (Greg Isenberg-adjacent, indie-hacker mid-tier)
- MarketingGardens client base — Jesse's existing book of agencies/SMBs (warmest list)
- Greg's MySeoDesk network — same play, different segment
- Application-only LP with scarcity (10 seats, dates fixed)
- Alumni referral after Cohort 1: one seat at $5K for any alum who refers a paid seat
Y1 marketing budget allocation ($30K)
| Channel | Spend | Why |
|---|---|---|
| Paid social (X + LinkedIn) | $12,000 | Direct funnel |
| Podcast sponsorships | $8,000 | 4–6 mid-tier founder pods |
| Content production (video, case studies) | $5,000 | Evergreen assets |
| Founder time / outreach | $3,000 | DMs, intros, application calls |
| Website + collateral | $2,000 | LP, application flow, pitch deck |
Pricing & offer architecture
- Standard: $10,000 — all-inclusive
- Premium upsell: +$500 premium economy flight upgrade
- Pay-in-full discount: $9,500 (saves Stripe fee + cash flow)
- Payment plan: $10,500 (3 payments — covers risk + fee)
- Refund policy: 60+ days out, 50% refundable; <60 days, transferable to next cohort, no cash refund
Positioning angles to test
- "Don't learn AI. Leave with your AI department deployed."
- "Retire $60K/year in SaaS in 5 days."
- "The Ownership Intensive — own your stack, kill your subscriptions."
- "From dirty-data CSV to deployed agent in 5 days."
07Operations
Pre-retreat checklist (T-90 → T-0)
- T-90: Finca contract + 50% deposit; sales open (LP live)
- T-60: Book host flights, lock excursions
- T-45: 50% applicants closed → book attendee flights
- T-30: Final balance collection; full attendee flight booking; pre-retreat Zoom (tech audit)
- T-21: Ship welcome kits
- T-14: Final tech audit per attendee, environment verification
- T-7: Speed-test Starlink at finca, confirm mesh WiFi, chef menu, excursions
- T-1: Hosts fly in early, site walkthrough, WiFi confirmation
On-site staffing
- 2 hosts (Greg + Jesse) — workshop, 1:1s, integration
- 1 chef (finca-provided or contracted)
- 1 housekeeping team (finca-provided)
- 1 driver + Sprinter van
- Optional: 1 local fixer / concierge ($50/day) for translation, last-minute supply runs
Legal & insurance
- Entity: US LLC, partnership 50/50
- Contract: refund, liability waiver, IP (their builds = theirs), code of conduct
- Insurance: event liability $1–2M + attendee health/evac rider ($500–$1500/cohort)
- Tax: US-source service revenue (host services); COP spend = COGS. No Colombia entity Y1.
- Banking: dedicated business checking, Stripe + USD merchant, escrow until departure
Risks & mitigations
| Risk | Mitigation |
|---|---|
| WiFi failure during workshop | Finca-provided Starlink as primary + Claro 4G hotspots + Ollama local fallback |
| Attendee health emergency | Mandatory travel medical insurance; nearest hospital identified pre-trip |
| Skill mismatch | Application screen + tech audit Zoom + Claude Code lowers the floor |
| Refund / chargeback | 60-day cutoff, signed contract, payment plan option |
| Finca cancellation | 50% deposit + force majeure + Venecia as backup to San José |
| US/Colombia FX shift | Lock major COP costs in USD where possible |
| Travel disruption | Attendee responsible for own travel insurance |
08Brand
Working names
- The Ownership Intensive
- Finca AI
- AI Hacienda
- Coffee & Code Colombia
- Cumbre AI (Spanish: "summit")
The story
Two practitioners — one a full-stack developer running 30+ AI-powered sites and a SaaS, one a marketing operator running multiple service businesses — bring 10 founders to a private hacienda in Colombia's coffee country. Five days. No slides. No lectures. You arrive with a CSV dump of your messy business data and leave with a deployed AI department: your own MCP server, a live Astro site, a voice agent answering your phone, and one fewer SaaS bill. Coffee at 6,000 feet, cumbia at sunset, code that ships.
09Year 1 Roadmap
| Month | Milestone |
|---|---|
| 1 | Entity, banking, contracts, insurance, finca selection + deposit |
| 2 | LP live, brand finalized, application flow built, pricing locked |
| 3 | Open sales for Cohort 1 (target ~Month 7) |
| 3–6 | Marketing push: podcast tour, paid ads, founder outreach |
| 6 | Cohort 1 confirmed (10 seats), flights booked |
| 7 | Cohort 1 runs (5 days) |
| 8 | Post-mortem, attendee case studies recorded, testimonials secured |
| 8 | Open sales for Cohort 2 |
| 10 | Cohort 2 confirmed |
| 11 | Cohort 2 runs |
| 12 | Y2 planning: 4-cohort schedule, Sazagua upgrade decision, Inner Circle launch |
10Open Decisions
- Entity structure: Single LLC (one owner, other contractor) vs partnership LLC? → Recommend partnership 50/50.
- Finca lock-in Y1: San José vs Venecia? → San José for brand premium. Visit both before Cohort 1.
- Cohort dates: Dry season favors Jan–Mar / Jul–Aug. Recommend Cohort 1 = Feb 2027, Cohort 2 = Sep 2027.
- Founder cash extraction Y1: $0 reinvest? Or $51K each? → Recommend $25K draw each + $50K reinvest into Y2.
- Inner Circle / alumni upsell: Launch in Y1 after Cohort 2 or wait for Y2?
- Recording rights: Sell post-retreat recordings as standalone $1,500 product, or alumni-only?
- Brand name: Lock by Month 2.