
Step 1e: Understanding
the “Game.”
🌫️ Big Idea
Most people play money like it’s checkers: linear, reactive, one move at a time. Wealth is chess—multi-move, multi-board, and asymmetric. There are rules (tax, credit, compounding), referees (laws, regulators), opponents (inflation, fees, scams), power-ups (skills, systems, networks), and victory conditions (cash flow + optionality + time freedom). When you see money as a game—with levels, roles, scoreboards, and playbooks—you stop guessing and start engineering outcomes.
This lesson gives you that operating system.
🧭 The Game Map
(What arena are you playing in?)
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The Consumer Game (Default Mode)
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Objective (false): look rich now.
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Mechanics: credit → spending → payments → repeat.
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Outcome: stress, little equity, time scarcity.
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Bosses: lifestyle creep, high-interest debt.
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The Builder Game (Upgraded Mode)
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Objective: create equity, systems, and cash flow.
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Mechanics: skills → value creation → margin → reinvestment → scale.
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Outcome: increasing income, assets, and control.
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The Investor Game (Parallel Mode)
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Objective: own productive assets.
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Mechanics: allocate capital → manage risk → compound → optimize taxes.
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Outcome: cash flow + appreciation independent of your hours.
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The Tax Game (Rulebook Mode)
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Objective: keep more of what you earn—legally.
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Mechanics: entity choice, deductions, deferrals, and asset location.
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Outcome: higher after-tax compounding.
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The Credit & Capital Game (Fuel Mode)
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Objective: borrow smart to buy/build cash-producing assets.
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Mechanics: underwriting, DSCR, terms, covenants, buffers.
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Outcome: amplified results (good or bad!)—hence the need for skill.
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The Time & Attention Game (Scarcity Mode)
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Objective: focus fire on the few things that move the needle.
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Mechanics: calendar control, automation, delegation.
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Outcome: time wealth.
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The Brand & Distribution Game (Leverage Mode)
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Objective: reduce customer acquisition cost and increase pricing power.
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Mechanics: audience, trust, content, partnerships.
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Outcome: compounding demand.
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🧱 Rules You Can’t Ignore
(Physics of the game)
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Compounding: Exponential growth rewards early and consistent play.
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Asymmetry: Cap downside; preserve uncapped upside (entrepreneurship, IP).
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Sequence risk: Same average return ≠ same outcome—order matters.
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Leverage: Financial (debt), operational (systems), code (software/AI), people (teams), media (audience).
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Second-order effects: Today’s comfortable choice can create tomorrow’s cage (e.g., car payment → job dependence).
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Optionality: Freedom scales with the number of good choices you can make at any time.
📊 Visuals for this lesson
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Power of Compounding: Start Now vs. Start Later
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Overflow Bucket System – Sample Allocation
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Debt Snowball vs. Avalanche (example)
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Risk vs Return Landscape (illustrative)
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Multiple Income Streams Example
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Use these where I reference them below.
🧮 Scoreboards
(how to tell if you’re winning)
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Net Worth (wealth stock)
Assets − Liabilities. Track quarterly. Segment into: liquid, productive, personal. -
Cash Flow (wealth flow)
Monthly inflows − outflows. Track personal and business. Guardrail: positive free cash flow after taxes and debt service. -
Freedom Index (time)
Non-labor income ÷ monthly burn. ≥1.0 = work optional. -
Velocity & Quality of Capital
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ROI (single project), IRR (timing-aware), Cash-on-Cash (income focus).
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Compare before/after tax, adjust for risk.
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Moat Strength
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Stickiness (retention), pricing power (margins), distribution (CAC/LTV), network effects (growth efficiency).
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👤 Choose Your Player Class
(stackable, not exclusive)
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Operator: Builds systems, hires, scales processes.
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Creator/Publisher: Builds audience + IP, monetizes via offers/ads/licensing.
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Deal Maker: Finds, underwrites, and closes favorable deals.
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Capital Allocator: Places money where it compounds with acceptable risk.
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Technologist: Automates, builds tools, captures 10× efficiencies.
Pick one primary, one secondary. Your unfair advantage lives at the intersection.
🧨 Bosses & Traps
(how the game fights back)
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Inflation: Quiet tax on cash. Antidote—productive assets, pricing power.
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Taxes: Legal but optional to some degree—entities, deferrals, locations, asset choices.
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Fees: Silent killers (funds, processors, platforms). Negotiate and benchmark.
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Lifestyle Creep: Upgrade your assets before your lifestyle.
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Bad Debt: Unsecured, high-interest, consumption-driven.
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Concentration Risk: One client, one platform, one job = fragile.
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Shiny Objects: New idea addiction → shallow progress. Install a parking lot list + review cadence.
🧰 Power-Ups
(level faster)
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Skills: pricing, copywriting, sales, analytics, negotiation, underwriting.
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Systems: SOPs, dashboards, automations, weekly reviews.
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Network: mentors, operators, distribution partners, capital sources.
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IP & Brand: proprietary methods, repeatable frameworks, recognizable positioning.
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Capital: retain earnings, create credit capacity, cultivate investors.
🔭 Strategy Pyramid
Vision → Constraints → Vehicles → Playbooks → Routines
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Vision: Why are we playing? (freedom, impact, legacy)
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Constraints: time, capital, skills, risk tolerance
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Vehicles: business, real estate, content/IP, software, public markets
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Playbooks: acquisition, product ladder, retention machine, pricing, tax
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Routines: weekly scorecard, build/sell blocks, money meeting, pipeline review
🚦 Vehicles:
What game pieces produce points?
1) Businesses (owned or online/offline hybrids)
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Pros: control, margin, scale, tax flexibility, saleable equity.
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Cons: execution risk, cash flow volatility.
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Keys: offer-market fit, distribution, unit economics, churn control, SOPs.
2) Real Estate (buy/hold, BRRRR, small multi, STRs selectively)
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Pros: leverage, depreciation, cash flow + appreciation, tangible collateral.
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Cons: management intensity, interest rate cycles, regulatory shifts.
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Keys: buy on yield and fundamentals, cash flow at conservative rents, capital reserves.
3) Public Markets (ETFs, factor tilts, dividend growth)
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Pros: liquidity, automation, historical compounding.
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Cons: volatility, behavioral traps.
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Keys: automate, rebalance, asset-locate for taxes, don’t confuse saving with speculating.
4) IP & Media (courses, books, licensing, ads)
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Pros: infinite marginal cost ≈ 0, global reach, compounding audience.
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Cons: creation consistency, platform risk.
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Keys: publish cadence, email list, product ladder, community.
5) Software & Tools (no/low-code, AI wrappers, internal automations)
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Pros: leverage of code, recurring revenue, defensibility via integration.
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Cons: build/maintenance, competition.
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Keys: solve costly problems, usage telemetry, keep it simple.
🧠 Decision Science: Choose like a pro
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Expected Value (EV): Σ (probability × payoff) − cost.
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Kelly-ish sizing: Tilt more to edge, cap exposure to ruin.
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Barbell: Most capital in safe/boring; a smaller slice in asymmetric upside.
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Regret Minimization: Choose options that keep future doors open.
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Base Rates: What usually happens in this domain? Don’t bet on miracles as a plan.
💵 The Tax Game (legal edges)
(Not legal advice; educational framing.)
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Entity choice: LLC → S-Corp election for owner-operator wages vs distributions.
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Deductible vs capitalized: Understand what lowers current vs future taxes.
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Depreciation: Real estate & equipment accelerate deductions; cost segregation (when appropriate).
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Retirement buckets: Solo 401(k), HSA, Roth backdoors—asset location matters.
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Deferral & timing: Shift income/expenses across periods when valuable.
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Home + office: Legal home-office, Augusta rule (where applicable), mileage logs, etc.
The goal isn’t avoiding taxes; it’s maximizing after-tax compounding.
🧾 Credit & Capital (smart fuel)
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Good Debt: collateralized, cash-flowing assets, fixed or hedged rates, DSCR buffer.
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Terms > Rate: covenants, amortization, prepayment flexibility, fees, personal guarantees.
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Liquidity & Reserves: 6–12 months debt service and op-ex across business + investments.
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Capital Stack: blend senior debt, mezz, equity; match duration to asset life.
Use debt to control assets that pay you; never to fund lifestyle.
🧪 Operating Playbooks
A) $0–$1,000 (Starter)
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Sell unused stuff; learning gigs; micro-services.
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Build publishing habit (proofs of work).
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70/20/10 cash flow split: essentials / debt / investing seed.
B) $10k–$50k (Foundation)
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Skill stack (sales + analytics or ops + media).
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Launch lean service business; productize one offer.
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Start simple investing automation (ETF DCA).
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Chart tie-in: Share the Overflow Bucket allocation (download).
C) $50k–$250k (Momentum)
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Hire contractor/VA; build SOPs; raise prices with guarantees.
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Add a second acquisition channel; improve retention.
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Small real-estate or digital asset acquisition with DSCR ≥1.25.
D) $250k–$1M (Scale)
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Team, dashboards, weekly ops drumbeat.
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Entity/tax optimization; consider line of credit.
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Build moats (brand, customer community, integrations).
E) $1M+ (Optionality)
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Professionalize finance; scenario models.
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Consider strategic partnerships, licensing, or partial exit.
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Barbell allocation: core boring + selective high convexity.
🛡️ Risk Management
(don’t lose the game to one play)
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Hygiene: insurance, emergency fund, diversifying revenue, legal contracts.
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Kill-switches: preset rules to pause spend/scale when metrics breach thresholds.
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Buffers: underwrite to worse-case cash flows; keep dry powder.
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Simplicity: complex systems fail in complex ways—fewer moving parts win.
🧩 Behavior
(the meta-game)
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Identity: “I am the kind of person who…” (ships, reviews numbers, invests monthly).
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Environment: Friction down for good behaviors (auto-invest), friction up for bad ones (no saved cards).
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Cadence: Monday scorecard, midweek pipeline, Friday review & plan.
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Community: Accountability beats raw willpower.
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📈 Walkthroughs with the charts
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1) Compounding—why “now” beats “later”
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Power of Compounding: Start Now vs. Start Later.
Download
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Same contribution, different start dates → drastically different outcomes.
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Translation: even small, automated contributions today beat larger, “someday” contributions.
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2) Overflow allocation to escape the paycheck loop
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Overflow Bucket Allocation.
Download
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Route income through a fixed sequence: essentials → bad-debt kill → emergency → investing → freedom fund → giving.
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This installs wealth by default instead of by willpower.
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3) Debt strategy—Snowball vs. Avalanche
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Debt Payoff Comparison.
Download
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Avalanche (highest rate first) often minimizes interest; Snowball (smallest balance first) often maximizes adherence.
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Choose the path you’ll finish. Momentum is a feature, not a bug.
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4) Picking vehicles: risk vs return
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Risk vs Return Landscape (Illustrative).
Download
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See how asset classes cluster. The “right” mix depends on timeline, skill, and temperament.
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Rule of thumb: earn your extra return with skill, not mere hope.
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5) Diversifying income for resilience
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Multiple Income Streams Example.
Download
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Goal: reduce single-point fragility (one job, one client).
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Add streams that stack, not distract: e.g., service → productized offer → course → SaaS → investment income.
🧱 Mini-Case Studies (game sense in action)
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The One-Client Agency
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Issue: 80% revenue from one client; “thumb-on-the-scale” risk.
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Play: 90-day pipeline sprint, price anchor + scope guardrails, retainers with pre-paid blocks.
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Outcome: revenue diversification → higher LTV → sellable business.
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The Landlord with Thin DSCR (DSCR = Debt Service Coverage Ratio)
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Issue: cash flow collapses with a 1% rate bump.
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Play: refinance term, increase reserves, add ancillary revenue (storage, parking, pet rents), expense audit.
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Outcome: stabilized NOI, optionality to acquire again.
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The Creator Without an Offer
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Issue: large audience, low revenue.
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Play: lead magnet → email nurture → core product → premium upsell, annual plan with community.
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Outcome: CAC ↓, ARPU ↑, churn ↓.
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The Over-Indexed Stock Picker
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Issue: emotional trades, poor tax efficiency.
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Play: automate DCA to core ETF, limit active bets to a small satellite with strict rules, harvest losses when appropriate.
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Outcome: calmer compounding, better after-tax returns.
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🧪 30/60/90 “Game Plan”
30 Days (Stabilize & See)
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Personal & business scorecards live (cash flow, net worth, pipeline, unit economics).
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Automate investing; cap discretionary leak.
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Choose primary/secondary “class” (Operator/Creator/Allocator/etc.).
60 Days (Systems & Acquisition)
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SOPs for your 3 core processes; publish weekly; build one distribution channel.
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Add one income stream that stacks with your main offer.
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Underwrite one asset (deal, property, digital product) with conservative assumptions.
90 Days (Scale & Moats)
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Pricing review; retention design; referral mechanism.
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Tax & entity review; line of credit or capital partners if appropriate.
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Ship one “power-up”: tool, calculator, mini-SaaS, or licensing deal.
📝 Exercises
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Game Audit (15 min)
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What games am I currently playing? Consumer, Builder, Investor, Tax, Credit, Attention, Brand?
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Where am I winning? Where am I bleeding?
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Player Class Selection
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Circle one primary and one secondary class. List 3 leverage skills to develop for each.
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Scoreboard Setup
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Create a one-page dashboard: net worth, cash flow, freedom index, pipeline, churn, CAC/LTV.
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Update weekly or bi-weekly, not annually.
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Vehicle Fit
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Rank vehicles by skill fit and interest (business, real estate, ETFs, IP, software).
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Pick 1 main vehicle for the next 12 months. Write the playbook you’ll run.
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Boss Mitigation Checklist
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Inflation hedge? Tax plan? Fee audit? Concentration risk? Reserves? Insurance updated?
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Optionality Map
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What 3 moves increase optionality the most in the next 90 days? (e.g., email list to own distribution; LOC for liquidity; cross-training a teammate.)
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🔑 Key Takeaways
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Money is a game—and games are learnable.
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Advance by stacking skills, systems, and assets.
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Keep score with net worth, cash flow, and freedom index.
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Win by protecting the downside and preserving upside.
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Choose a vehicle and commit; add streams that stack, not distract.
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Install routines—because consistency beats intensity.
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Use the charts to teach compounding, allocation, risk, debt strategy, and diversification.
