Mark Cecchini, CFP®

so, you want to learn more about equity compensation? I get this question quite a bit. here's what I suggest to anyone when they reach out. >>> start with understanding the basics ISOs, NSOs, RSUs, ESPPs, 83(b) elections, AMT, 409A valuations, vesting schedules, exercise mechanics, etc. understand how each works, when taxes are triggered, and how they ultimately show up on someone's tax return. look up examples of equity incentive plans, grant agreements, exercise math, trading policies, tender offer documents, pre-IPO S-1 filings, W-2s, tax forms, paystubs, etc. >>> consume as much content as you possibly can YouTube Podcasts Websites: > Compound Manual > SecFi > EquityFTW > Carta > Pulley > Zajac > MyStockOptions > QSBS Rollover X / Linkedin: > Bryan Hasling > Matt Gottshall > Chris Arnold > Daniel Zajac > Thomas Kopelman > Mike Zung > Kris Barney > Frank Alvarez > Max Pashman >>> check out some of the SaaS products in our space > Trayecto > Gemifi > StockOpter > EquityNav > Grantd > Holistiplan >>> TALK TO YOUR AI CHATBOT ! this should be one of the new defaults when looking to go super deep on any given topic. ask to give you a crash course on equity compensation in your preferred learning style. ask it to point you to the most relevant resources for equity compensation in whatever niche you want to focus on (public companies? private companies? startups? traditional executive compensation? QSBS?) >>> attend masterclass programming > Trayecto > MyStockOptions >>> Enroll in professional designation programs if you want to > ECA > CPWA ultimately, nothing can ever replicate working with clients IRL who have equity compensation. attracting and working with those clients is not easy, but this is the only true way to level up in this area. work through real cases, ideally alongside experienced professionals when you're starting out. every company is different. every equity plan is different. every client's circumstances are different. every liquidity event is different. the more situations you encounter, the better you become at recognizing problems, identifying opportunities, and understanding the consequences of a recommendation. (screenshot shared with permission)

So, you want to run a comprehensive financial planning process like we do in the big leagues? Here's what you'll need to gather: 1. Investments and Equity Compensation ☐ Investment account statement(s), include all ☐ 401(k) or 403(b) statements from former employer(s), if applicable ☐ Annuity contract statements, if any ☐ Stock option grant agreements (incentive stock options and/or non-qualified options) ☐ Stock option vesting schedules and exercise history ☐ Restricted Stock Unit (RSU) award agreements and vesting schedules ☐ ESPP (Employee Stock Purchase Plan) enrollment and purchase history ☐ Deferred compensation plan statements, if applicable ☐ Concentrated stock positions, showing shares held, cost basis, and acquisition dates ☐ 10b5-1 trading plan documentation, if applicable ☐ Form 3921 (ISO exercises) and Form 3922 (ESPP transfers) from recent years ☐ Any equity awards from prior employers still held or recently exercised 2. Bank Accounts & Certificates of Deposit ☐ Checking account statement(s) most recent month ☐ Savings account statement(s) most recent month ☐ Money market account statement(s), if applicable ☐ Certificate of Deposit (CD) statements, include maturity dates and interest rates ☐ List of all bank accounts with approximate balances (if statements not readily available) 3. Pension Benefits ☐ Most recent pension benefit statement showing monthly/annual benefit amount and tax withholdings ☐ Pension election form (showing chosen payout option: single life, joint & survivor, etc.) ☐ Cost-of-living adjustment (COLA) provisions, if any 4. Social Security Benefits ☐ Social Security benefit verification letter (SSA-1099 or current benefit statement) ☐ Monthly benefit amount confirmation and tax withholding verification ☐ Medicare premium deduction confirmation (if withheld from SS benefit) ☐ Date benefits commenced 5. Medicare & Health Insurance ☐ Medicare card ☐ Medicare Part B / C / D information ☐ Medicare prescription drug plan summary and premium information ☐ Medicare Supplement (Medigap) policy declarations page, if applicable ☐ Employer or retiree health benefits, if any ☐ Dental and vision insurance information, if separate coverage 6. Life, Disability, Property Insurance ☐ Life insurance policy declarations page(s) for term and/or permanent policies ☐ Disability policy declarations page(s) for group and/or private policies ☐ Life insurance in-force illustration (for permanent/cash value policies) ☐ Long-term care insurance policy and benefit summary ☐ Homeowners insurance declarations page ☐ Auto insurance declarations page ☐ Umbrella/excess liability insurance policy, if any ☐ Any other insurance policies (jewelry, valuable articles, etc.) 7. Income Tax Information ☐ Federal tax return (Form 1040) most recent two years with all schedules ☐ State tax return most recent two years, if applicable ☐ Form 1099-R (retirement/pension distributions) most recent year ☐ Form 1099-INT (interest income) most recent year ☐ Form 1099-DIV (dividend income) most recent year ☐ Form 1099-B (brokerage/capital gains) most recent year ☐ Form SSA-1099 (Social Security benefits) most recent year ☐ Property tax bill for primary residence ☐ Estimated tax payment records (Federal + State) for current year ☐ Charitable contribution information, if applicable 8. Estate Planning Documents ☐ Last Will and Testament ☐ Revocable Living Trust agreement, if applicable ☐ Durable Power of Attorney (Financial) ☐ Healthcare Power of Attorney / Healthcare Proxy ☐ Living Will / Advance Healthcare Directive ☐ Beneficiary designation forms for all retirement accounts (IRA, 401k, etc.) ☐ Beneficiary designation forms for life insurance policies ☐ Trust beneficiary designations, if applicable ☐ Any irrevocable trusts (life insurance trust, charitable trust, etc.) 9. Real Estate & Personal Property ☐ Property tax assessment or appraisal for primary residence ☐ Estimated current market value of home ☐ Deed or title documentation (showing ownership type: sole, joint, trust, etc.) ☐ Vehicle information and estimated values ☐ Valuable personal property inventory (art, jewelry, collectibles) if significant 10. Liabilities & Debt Obligations ☐ Credit card statements showing balances, if any ☐ Auto loan statements, if any ☐ Home equity line of credit (HELOC) statement, if any ☐ Personal loan documentation, if any ☐ Any other debt obligations 11. Income & Expense Information ☐ Estimated monthly living expenses (or detailed budget if available) ☐ List of regular recurring expenses (utilities, subscriptions, etc.) ☐ Expected large upcoming expenses (travel, home improvements, gifts, etc.) ☐ Any part-time work or consulting income anticipated ☐ Rental or other passive income documentation, if applicable 12. Additional Information ☐ Previous financial plan or investment policy statement ☐ Contact information for other advisors (CPA, attorney, etc.) ☐ Family situation details (dependents, support obligations, etc.)

Privately held stock is one of the most misunderstood concepts in personal finance. as an employee or founder, the number in your Shareworks / Carta login has a LONG way to go before it's cash in the bank. these are the concepts that turn paper wealth into real wealth ↓↓↓