Career and equity planning

Career Change, Equity, and Entrepreneurship

A job offer can arrive with a large equity number and very little help interpreting it. An option exercise can have a short deadline, a real tax bill, and no market where you can sell the shares. We put actual numbers around those choices.

Three different questions

Compare an offer, exercise options, or plan for self-employment.

Comparing offers

We compare salary, bonus, benefits, vesting, equity terms, and the compensation you leave behind. The largest number on the page is not always the most valuable one.

Exercising options

We model the cash required, income tax and alternative minimum tax (AMT), and how long shares must be held for particular tax treatment. We also consider whether you could sell the shares when you need the money.

Leaving the paycheck

Moving to self-employment means arranging tax payments, health insurance, retirement saving, and any disability coverage you need. We help you account for those costs alongside the needs of the business.

Understanding the grant

Startup options are not cash compensation.

They are a conditional right to buy common stock. The company has to succeed, the common shares have to be worth more than the strike price, and you need a way to sell before the grant produces spendable money.
How to evaluate startup ISOs

Documents and facts

What we want to see before running the numbers.

The plan documents explain the rights, restrictions, and deadlines behind the offer.

  • The offer letter, equity grant, vesting schedule, and option-plan documents
  • The strike price, current 409A valuation (an estimate of common-share value for tax purposes), grant expiration, and time allowed to exercise after leaving
  • The latest preferred-share price and any liquidation preferences (rights that can give investors priority when sale proceeds are distributed)
  • Your existing company stock, unvested compensation, benefits, and tax situation
  • The amount of cash you can risk without putting the rest of the plan under strain

Concentration

Decide how much to tie to one company.

Company equity can create substantial wealth. It can also tie your income, benefits, career prospects, and investments to the same business. We help set rules for exercising, holding, and selling before a rising share price makes every sale feel premature.

Career and equity planning

Tell us about the choice and its deadline.

We can discuss how the decision fits into your finances and whether ongoing planning with Pathfinder would help.

Start a free conversation