Total Comp Playbook
The Total Comp Playbook · Form 04 · Ownership · Curriculum map
The Total Comp Playbook
Understand every way you're paid. Convert it to wealth. Your career capital is your largest asset — and the rules that convert it into net worth were written by a compensation committee optimizing shareholder value, not yours. This curriculum teaches you to read that design from the inside, so you stop being a passive recipient and start directing the professionals you already pay.
Why this exists · who actually sets your number
You were handed the surface. The design was never yours to see.
The committee's side of the table
The number the system shows you — the plan platform, the equity portal, the benefits page, the comp summary — was built for proxy advisors, institutional investors, and the board, and optimized for the company: retention, defensibility, dilution cost, shareholder value. The layer that explains it — the CD&A, the plan document, the proxy, the cap-table waterfall, the consultant's model — is the document you were never handed.
This is not a do-it-yourself course, and it will not replace your professionals. It's the scope they don't give you: what to ask, in what order, before the window closes. You already pay a CPA, a wealth advisor, legal counsel, and a coach. This makes you the client who gets the most out of all four.
CPA
Tax: exercise, AMT, withholding, QSBSWealth advisor
Equity, concentration, diversificationLegal counsel
Offer terms, cap table, separationExecutive coach
Career capital, negotiation, re-ratingThe shared framework · the logic, not the instruments
One diagnostic, one path — then everything forks
A = L + E
Assets are what the system shows you. Liabilities are everything between that number and your household — taxes, restrictions, concentration, fees, the preference stack. Equity is what's actually yours. The formula is shared; the contents of each column are not.
Auditread the design
→
Optimizemove while you can
→
Exityour terms, not theirs
→
Reckonwhat reached you
Both arcs march through the same four phases — the insider's sequence. But the instruments, the tax mechanics, and every module fork. The two arcs share a shape, and one capstone — Module 08, where you become the coordinator — and each closes on a shared horizon: how the AI transition reprices the whole design.
Why two basics · the instruments genuinely differ
Each arc opens with the tools that actually govern its pay
Restricted stock awards, 83(b) elections, and early exercise live in the private world. RSUs, ESPP, and trading-window mechanics live in the public one. There is no shared primer — each arc starts with its own Basics, scoped to the instruments used to acquire and retain that talent. Skip it if you already know the instruments.
Public Basics covers
Liquid-company instruments
RSUsESPPNSOs / ISOsPerformance equityVestingTrading-window basics
Pre-IPO Basics covers
Private-company instruments
Options (ISO / NSO)RSAs83(b)Early exerciseOptions vs. sharesCap-table view
Is your equity liquid, or is it still a story?
↙ Public arcPre-IPO arc ↘
Public arc · periwinkle · 7 modules
The number is real
Your equity is liquid. The question is how much of it you keep.
Foundation
01
The BasicsRSUs, ESPP, options, performance equity — how liquid-company pay works.Optional · skip if you know it
Audit · read the design
02
What You Hold & Who Designed ItThe instruments as engineered, the committee that set your number, and the proxy that explains it.The read that arms every brief
Optimize · move while you can
03
The Money MovesTrading windows, concentration, the tax engine, cash, benefits and deferred comp.→ Brief for CPA & wealth advisor
04
The Career-Capital Re-RatingPerformance pay is being repriced against your role's durability under AI. Read it before the refresh does.→ Brief for your coach
Exit · your terms
05
Leave on Designed TermsLockup, departure, change of control, separation — navigated, not discovered.→ Brief for legal counsel
Reckon
06
The Events You Don't ChooseA reduction in force, disability, death, a change in control — the exits you don't design, each pre-written by documents you signed.→ Brief for counsel
Horizon · where pay is going
07
The Augmented PremiumHow AI redesigns total-comp structure — and prices augmented talent at a premium. The forward read, and the bridge to the rest of your career capital.→ The career-capital bridge
Pre-IPO arc · indigo · 7 modules
The number is a story
Your equity is illiquid. Learn to read it before the windows close.
Foundation
01
The Basics & The BetOptions, ISOs/NSOs, RSAs, 83(b), early exercise — and the risk/reward bet you're making: the lottery, or the experience that earns the future premium.Skip the vocab · keep the bet
Audit · read the design
02
The Offer & The Hidden LayerThe offer as designed, the protection terms you signed, and the preference stack you've never seen.→ Brief for legal counsel
Optimize · move while you can
03
Exercise, Timing & TaxThe 30-day clock, the exercise trap, the AMT shadow, QSBS, and secondary liquidity.→ Brief for your CPA
04
The Ongoing NegotiationCounter-offers, refresh grants, the benchmark trap, golden handcuffs — the retention machine.→ Brief for your coach
Exit · your terms
05
The Liquidity Event (or Not)Get ready before the event, read every version of the door, and cross the bridge into the public-company world — or the zombie if it never opens.→ Brief for CPA & counsel
Reckon
06
The SeparationLeaving as a position to close — the final settlement, what protection survives, and the narrative. Negotiated at the offer, not the exit.→ Your separation brief
Horizon · where pay is going
07
The Augmented PremiumHow AI reprices augmented talent — and why startup-survivor experience, AI-augmented, commands a premium and a larger equity share. The forward read, and the five-forms bridge.→ The career-capital bridge
Different equity, different exits — converging on one horizon: how AI repricing turns augmented talent into premium talent.
Where this hands off
Ownership is one of five forms of career capital. The AI premium goes to whoever compounds the others too — which is where the rest of the portfolio picks up.
ExpertiseLeverageTimeOwnership · you are hereIndependence
Module 08 · across both arcs
The Coordinator
Every advisor optimizes their own domain, and none was hired to coordinate with the others — so the plan on paper is never the plan that executes unless you make it. You are the coordinator of your own advisor team, and those advisors must be fluent in executive compensation. The one module both arcs share, it houses the two practical instruments:
This is education, not advice. Nothing here is personalized tax, financial, or legal advice — it's the scope to bring to the professionals who give it. Year-specific tax figures (AMT, QSBS, NIIT, contribution limits) are date-stamped and isolated in each module for quick refresh; confirm current figures with your advisor before acting.
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