Shehan Chandrasekera
Head of Tax, Nino
Shehan leads tax strategy at CoinTracker and Nino and is a nationally recognized expert in cryptocurrency taxation. He was 1 of 12 experts selected to testify on U.S. Treasury digital asset regulations and was named to CPA Practice Advisor’s 40 Under 40. He is also frequently quoted by Bloomberg, Reuters, and CoinDesk on crypto tax developments.
1 of 12
experts selected to testify on U.S. Treasury digital asset regulations.
40 Under 40
CPA Practice Advisor honoree, frequently quoted by Bloomberg, Reuters, and CoinDesk.
18
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
- Incentive stock options
- Liquidity events
- Startup founders
- Cryptocurrency taxes
- Financial advisors
- Qualified small business stock
Reviewed by Shehan
Shehan reviewed each of these for accuracy. An article’s updated date records a later content edit, not a new review.
Capital Gains Tax When Selling Company Stock: What You'll Net
Federal capital gains tax, the 3.8% NIIT, state tax, and escrow each take a layer of a company stock sale. Here is how to estimate what reaches your account before you sign.
ISO Early Exercise for Founders: What the 83(b) Election Does and Doesn't Do
Early exercising ISOs can lock in a small AMT spread, but on ISO shares the 83(b) election does not start the capital gains clock. Here is how the rules work for founders, and when to skip it.
Pre-IPO Stock Option Tax Planning: The Founder's Checklist
A founder holds founder stock, ISOs, and NSOs at once, and the pre-IPO window closes several tax decisions on their own deadlines. Here is what to check, and in what order.
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: Why RSUs Look Taxed So High, and How Sell-to-Cover Works
RSUs are taxed like salary. Here is why a vest loses so many shares to withholding, why it can still leave you owing in April, and how sell-to-cover works.
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.