Recently I polled my peers on a social media platform dedicated to tax professionals. My hope was to find a resource for tax rules on a state level for handling gambling sessions. I knew it would be an uphill battle to get the information needed for a comprehensive guide state-by-state.
What surprised me was the response. A large percentage of tax professionals were either unaware of gambling sessions or were unclear on how gambling sessions were handled in their state. Since gambling sessions might be the best way to reduce taxes on gambling wins, a lot of money might be left on the table with clients paying the price. Even if the state a tax professional prepares most tax returns for does not have gambling, the likelihood a client travels to a state that does, gambles, and wins is high.

Tax Loss Harvesting with Cryptocurrency
In the Fall of 2025, Bitcoin reached an all-time high of over $120,000. Since then, it fell over 40% to under $70,000 in the first quarter of 2026, before slightly recovering, currently resting around $75,000 as of this writing. With the steep drop in the price of Bitcoin and other cryptocurrencies, a common question from taxpayers is whether they can use the current losses to offset their other income. Large investors and professionals such as Grant Cardone and Shehan Chandrasekera (Head of Tax Strategy at Cointracker) have suggested that cryptocurrency can be sold and bought back immediately to claim the tax benefits. As with most things, the answer to this is not as simple as they portray, and many commentators, influencers, and sometimes professionals, miss the intricacies of cryptocurrency taxation.


