Shehan Chandrasekera
Head of Tax Strategy at Nino
Shehan Chandrasekera, CPA, runs tax strategy at both CoinTracker and Nino. He is one of the few CPAs nationally recognized as an expert in cryptocurrency taxation.
1 of 12
people the US Treasury selected to testify on digital asset broker regulations.
2x 40 Under 40
CPA Practice Advisor honoree, and a Forbes tax contributor quoted by Bloomberg and Reuters.
16
Nino articles Shehan reviewed for accuracy.
What Shehan reviews
The topics of the Nino articles Shehan checks for accuracy.
- Equity compensation
- Tax planning
- Restricted stock units
- Capital gains tax
- Cryptocurrency taxes
- Financial advisors
- Liquidity events
- Stock options
- Tax filing
- Tax withholding
Reviewed by Shehan
Shehan reviewed each of these for accuracy. An article’s updated date records a later content edit, not a new review.
RSU Tax Planning: A Year-Round Strategy for High Earners
Project every vest for the year, model a few stock prices, and compare employer withholding to your household's tax before each vest, not in April.
RSU Vesting, New Job, Same Year: Model Your Tax Bracket
When RSUs vest at two employers in one year, each payroll withholds as if it were your only job. Here is how to size the gap and close it with W-4 withholding or estimated payments.
Concentrated Stock Position: How to Diversify Without Ignoring Taxes
Size the exposure, including shares still vesting, stress-test a drop, then sell down over several tax years under the 2026 capital gains and charitable rules.
Crypto CPA or Financial Advisor: Who Do You Need?
A crypto CPA handles cost basis, Form 8949, and 1099-DA reconciliation. A financial advisor handles allocation and concentration. When you need each.
How ESPP Is Taxed: Qualifying vs Disqualifying Dispositions
ESPP shares are taxed when you sell, and the holding period decides how much is ordinary income. See the math, Form 3922, and the 1099-B basis fix.
How to Avoid an AMT Surprise When You Exercise ISOs
Exercising incentive stock options can create alternative minimum tax before you sell a share. Here is how to size the exercise so you keep enough cash and avoid a year-end surprise.
What Does a CPA Plus a Financial Advisor Cost With RSUs?
Add the invoices, check which equity work is included, and assign ownership of withholding, sales, and tax filing.
A Tax and Cash Checklist for an Equity Liquidity Event
Before a tender offer, IPO-related sale, or acquisition, identify the taxable event, reserve cash, and reconcile your stock records.
RSU Tax Withholding and Sell-to-Cover
How employers fund RSU taxes, why withholding can miss your final bill, and how to check the gap before you file.
Why Are RSUs Taxed So High?
RSUs use ordinary income-tax rates. Learn why total withholding can look high and why it can still fall short of your final bill.
How Much Does a Crypto Tax Accountant Cost?
Crypto tax fees depend on record cleanup and return complexity. Compare software, reconciliation, filing, and representation as separate services.
ISO vs. NSO: Tax Differences and a Worked Example
ISOs can create AMT before a sale; NSOs usually create compensation income at exercise. Compare the cash cost and holding-period tradeoffs.
From Stock Options to Spendable Cash: The Liquidity Math
An equity valuation is not spendable cash. Subtract exercise costs and taxes, then check when your shares can actually be sold.
What Is QSBS? Eligibility and Tax Exclusion Rules
Qualified small business stock may qualify for a federal gain exclusion. Acquisition date, company eligibility, holding period, and basis determine the benefit.
RSUs vs. Stock Options: Ownership, Risk, and Taxes
Compare how RSUs and stock options deliver value, when taxes arise, and what cash you need before choosing an action.
How to File an 83(b) Election
An 83(b) election changes when restricted stock is taxed. Learn when it applies, how to file, and what to check within 30 days of the stock transfer.