The Primary Goal
Travel. Check in occasionally. Have plenty of money. Enjoy life with my wife.
Build businesses that run themselves — operated by capable humans managing small teams of AI experts, with me as the visionary/owner who isn't in the day-to-day. Hugo on GiftCue is the working proof of concept. The job is to document that model, harden it, and replicate it across every business I build.
📊 Targets at a Glance
<20
Active hrs/week in 12 mo
$10K+
Monthly personal draw floor
$200K+
BT revenue target (2026)
$3M+
Exit / sellable IP target
2+
Businesses on virtual operator model
0
Burnout events. Ever again.
🧭 Personal Goals — 12 Months
- Working under 20 hours/week actively
- Cash flow covers at least $10K/month personal draw, positive business cash flow on top
- Traveling more — staying longer in places, not rushing
- More present time with my wife; she grows with this venture, not just watches it
- Not managing anyone directly — that goes through an operator layer
- Health protected: no burnout, no depression spiral, sustainable pace
Hard constraint — burnout
Deep depression after last startup failed and we declared bankruptcy. Classic founder burnout. Terrifying. Recovered. Will not go through that again. If a path requires grinding, it is the wrong path. Non-negotiable.
Marriage first
My wife has real concerns about me losing humility and "getting a big head." It's happened before. She needs to be included in the growth, not just witness it. Her perspective is a check on my blind spots — and she's usually right.
⚖️ Values & Hard Lines
I will not:
- Break any laws
- Compromise on ethics for revenue
- Work with or for anything that advances the MAGA movement or undermines democratic values, norms, or institutions
- Build anything that harms any stakeholder — clients, employees, contractors, customers
I believe:
- Mutual benefit is the right model: value to all stakeholders AND millions of dollars for me and my family. These are not in conflict.
- Businesses can be kind, empathetic, and commercially sharp simultaneously.
- Humility is a competitive advantage, not a weakness.
Kind
Spiritual (not religious)
Empathetic
Driven
Creative
Former electrician → software executive
Technically fluent, not a developer
💰 Financial Constraints
Minimum floor: $10K/month personal draw + positive business cash flow covering all expenses.
Budget for tools/experiments: Open to virtually any monthly spend as long as cash flow stays positive above the floor. Not an absolute number — it's a cash flow test. Generates more than it costs and keeps the floor intact: it's in.
Current state
Cash flow positive but tight. More passive cash flow and more BT clients are the most urgent needs right now.
🔵 BOSSTORQUE — Goals & 90-Day Priorities
12-month goal: $200K+ revenue (2026 calendar year stretch; 12-month rolling minimum). Mix of recurring retainer clients and $50K/6mo workshop packages.
The operator model
BOSSTORQUE needs a capable operator who manages a small team of AI-fluent people — University of Oregon AI club model (founding president tier). That operator layer is what lets Jason step back. Not good at direct employee management — gets frustrated with skill gaps and constant questions. That's a constraint to design around, not a failing to fix.
90-day priorities
- More clients — workshop packages at $50K/6mo
- First AI-smart operator or contractor who can drive Cowork at Jason's level
- Rock-solid risk mitigation — legal exposure, AI mistakes, client liability. Must be built before scaling.
IP strategy
Everything built into GitHub client-templates repo. Every engagement builds replicable, sellable IP. Target exit: $3M+.
🟣 GiftCue — Goals & Operator Model
Operator: Hugo is the CEO. Jason's job is to make Hugo's capability rock solid — not to run GiftCue himself.
12-month priorities (in order)
- 1. Passive revenue — mostly automated, generates cash with minimal active time from Jason
- 2. Sellable or fundable — strong secondary goal if the model proves out
The bigger mission
GiftCue is the live proof of concept for the virtual operator model. Every improvement to how Hugo operates is IP — document it and replicate it across future businesses. This is the playbook.
🟢 Sperry Tree Care — Goals
Relationship: Client. Not a business Jason owns — a business he serves.
Dual goal
- Systematize their operation — build the automations, hand the owner a machine that runs without constant attention
- Document as a BT case study — becomes the playbook sold to other field service clients in workshops
Active time target: Near zero once systems are built. Cowork handles monitoring, daily workflows, lead follow-up, content distribution.
🤖 The Virtual Operator Model — The Real Business
GiftCue/Hugo is version 1. The pattern:
- Business idea + market
- Virtual operator (AI-assisted human CEO or fully AI agent)
- Small team of AI-expert contractors reporting to operator
- Owner (Jason) checks in occasionally, provides vision, collects cash flow
Documenting how Hugo works, what breaks, what needs human judgment vs. full automation — that becomes: the BT workshop curriculum, the playbook for future businesses, and the IP that makes BT sellable.
Longer-term vision
Multiple businesses running this model. Passive cash flow from each. Location independent. Family-first schedule.
What "Done" Looks Like
In 12 months, Jason is checking in on his businesses from somewhere he wants to be. His wife is with him. An operator is handling the day-to-day. Cash is flowing above the $10K floor. He's not burned out. He's building new things because he wants to, not because he has to. The Hugo model is running on at least two businesses. BT has 3–5 workshop clients and at least one AI-smart team member. Sperry is systematized. Working under 20 hours a week on things he actually enjoys.
📋 Instructions for Claude / Cowork
→Always optimize for the primary goal: step back, not step in.
→Flag anything that adds to Jason's active workload without a clear path to delegation or automation.
→When in doubt: automate it, delegate it, or kill it.
→Never recommend a path that requires grinding. Sustainable pace is the constraint.
→Hugo/GiftCue is the model. When building workflows for any business, ask: "Could Hugo (or a Hugo equivalent) run this?"
→Mutual benefit in everything. If a tactic feels extractive, it's wrong even if it's legal.
→Check in on the burnout constraint. If the task list is growing faster than it's shrinking, say so.
→Keep humility in the work. Jason's wife is right.