You are about to trade something certain for something that might be worth nothing. That is what equity is — a claim on a future that has not happened yet, priced by people who need you to believe in it.
Seven decisions, spread across about six years. Each one moves your skill, your wealth, your reputation, and whether the life around the work still works. Nobody is going to tell you the right answer, because there isn't one — there is only the version of it you can live with.
No trivia and no right answers — a narrative run about what you actually own when you are paid in equity.
Four archetypes, four starting hands. Your pick sets the stats you begin with — not the ones you end with.
Seven decisions, each one nudging skill, wealth, reputation, and wellbeing. No take-backs.
Your choices resolve into one of six outcomes — and an honest read on what that pattern costs.
Each archetype begins with a different balance of strengths. Your pick sets the stats you start with — not the ones you end with.
Below is the whole run — every chapter, every option, and where each one leads. Press Play this run above to take it as a game instead, with stats that move as you choose and an ending scored from how you played.
A Series A startup wants you badly. Fifteen percent below what you earn now, plus a grant they describe as "0.4% of the company." Someone in the room does the arithmetic out loud: at a $500 million exit, that's two million dollars.
Your current job is stable, unexciting, and pays on time. You have four months of expenses saved. The offer expires in a week.
Eleven months in. Your one-year cliff is four weeks away — nothing vests until you cross it. The work has been better than you expected and worse than you'd admit.
A recruiter calls with a role that pays properly, starting immediately. Waiting a month costs you the offer. Leaving now costs you every share.
The Series B closes at a lower valuation than the A. New investors get terms that put them ahead of everyone who came before, including you. Your 0.4% is now closer to 0.25%, and the shares underneath it are worth less each.
An all-hands is called. The framing is "exciting new partnership." Nobody uses the phrase "down round."
A launch that decides the next raise is eight weeks out and three months of work behind. Leadership asks for "one big push." You have not felt rested since Chapter 02.
You are senior enough now that whatever you agree to becomes what the team agrees to.
You're leaving — your choice, on decent terms. Then the paperwork explains the part nobody mentioned in Chapter 01: you have ninety days to exercise your options, paying the strike price in cash. On paper gains, you may owe tax on stock you still cannot sell.
The number to keep everything is more than your savings. The company is not public. There is no market.
Two years later, an email: the company is running a tender offer. Employees and ex-employees can sell a portion of their shares at a set price — the first time your paper has ever been convertible into money.
The price is real but modest. The rumour is that a bigger round, or an acquisition, is eighteen months out.
The company exists, smaller than promised and larger than it had any right to be. You have a number, or you don't. Either way the years are spent.
Someone starting out asks whether they should take the equity or the salary. For once you have to answer honestly, and your answer says more about you than about the offer.
No ending is the “best” one — only the one your decisions earned.
You got good at the thing, and the thing paid.
You never made the number that gets written about, but you learned to read a cap table, size a bet, and leave before the story curdled. The skill compounded in a way the equity never did — and it moves with you, which no grant ever does.
You took the certain money, and you were right to.
You sold at the tender, or negotiated cash over paper, or left before the cliff and never looked back. There is a version of this where you left millions on the table. There is also the version where you didn't — and either way, you own the outcome instead of hoping for one.
Your position was never the equity.
You asked the uncomfortable question in the all-hands. You cut scope instead of people. Somewhere there are a dozen engineers who know exactly what a preference stack is because you explained it. That network outlasted the company, and it keeps paying.
You held, and holding became the identity.
You exercised everything, declined the tender, and stayed through the down round. Conviction is genuinely how outsized outcomes happen — and it is also how people talk themselves past every exit. Only the final number tells you which one this was, and it tells you far too late.
They tell your story. You'd like a year off.
You led every push, absorbed every crunch, and shipped things that should not have shipped on those timelines. The respect is real and so is the damage. The useful part: you now recognise the pattern early enough to refuse it next time, which most people never do.
Nothing spectacular. Nothing broken.
No stat off the charts: decent money, real skill, people who trust you, and a life that still fits around the work. You asked the questions, sized the bet so failure was survivable, and sold half when half was enough. It reads as unambitious right up until you compare it to everyone else's decade.
The company, offer, valuations and endings in this run are fictional. They are not a cap table, an offer letter, a tax calculator or an estimate of a startup's prospects. A game score cannot tell someone whether a salary-equity trade is fair, whether options should be exercised, or whether a company will survive. Those decisions depend on documents and facts outside this page.
The scenario is designed to separate labels from terms. A share count, headline valuation or promised upside is not enough to understand an offer. Readers should know what instrument is being offered, when it vests, what happens on leaving, whether there is an exercise window, what dilution means in their plan, and what cash obligation could arise. The linked Investor.gov and IRS material is U.S.-oriented background; company-specific documents and country-specific tax rules take priority.
The down-round and tender-offer chapters are not predictions that any particular event will happen. They show why liquidity matters: an interest in a private company may be hard to sell, may change in value, and may never become cash. A person should avoid treating an estimated future value as money available for rent, debt, tax or an emergency. The emergency-fund source is relevant because a financial buffer can change how much uncertainty is bearable, not because it supplies a universal amount.
The run also cannot assess career value. A role may provide skills, colleagues, responsibility or optionality that do not fit into an equity calculation. Conversely, a compelling mission does not remove the need to understand pay, workload and downside. Both can be true without making one choice universally correct.
Use the game as a document checklist: offer letter, equity plan, vesting schedule, exercise terms, tax questions, salary/cash needs, and the person qualified to explain each item. Ask before a deadline rather than relying on an ending screen. The references below provide general U.S. educational material, not investment, tax, legal or employment advice.
One comparison is to describe the offer twice: first using only confirmed cash compensation and working conditions, then adding the equity instrument with every unknown term left visibly unknown. This is a stress test for the story attached to the offer, not a valuation method and not an instruction to assign equity a particular value. A person might also compare a negotiated change in cash, scope, or timing, but only the employer can say what is available and only the governing documents define the equity.
Before accepting or acting on an offer, list the exact documents you have, the terms you cannot yet explain, dates that affect a decision, expected cash costs, and the qualified person who can answer each question. Keep compensation and personal cash needs on the same page, but do not convert a speculative value into spendable money. This exercise does not value the company or advise on tax; it makes missing information visible before an irreversible deadline.
Ask what is guaranteed in cash and what is contingent equity; which terms control vesting and leaving; whether there are exercise or tax deadlines; and what happens if the company raises money or never creates liquidity. Ask for the current governing documents, not a verbal estimate of future value. These questions can improve understanding of an offer, but they cannot establish the offer's value or the right career choice.
Use the authored links below to examine the main trade-off from another angle.
The run has no correct path, but it does have a shape. Almost every ending that goes badly starts the same way — a decision made on a number nobody had committed to, sized so that being wrong was unaffordable.
Equity is not a salary with a delay. It is an illiquid, dilutable claim that may never convert, governed by terms you usually see only on the way out. That does not make it a bad bet. It makes it a bet, which is a different thing from a plan.
This is a narrative simulation for general financial and career education. It is not financial, investment, tax, legal, or employment advice, and the stat effects are storytelling devices rather than predictions. Equity compensation and its tax treatment vary by country, company, and grant type — speak to a qualified professional about your own offer.