Category Archives: Taxes

How to Exit a Losing Crypto Position (Without Calling It Quitting) – Part 5

Selling at a loss feels like admitting defeat, but holding a bad position longer just makes you wrong longer. This post covers when exits make strategic sense, the tax benefits of realized losses, practical steps for closing LP positions, and why walking away from a mistake is portfolio management, not failure. Continue reading

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Crypto in Estate Planning, Part 4: The Tax Headache Your Heirs Need You to Solve Now

Without proper tax documentation, your heirs could pay thousands more than necessary—or lose track of cost basis entirely. This guide covers stepped-up basis rules, cost basis tracking, executor responsibilities, and when to involve a crypto-savvy CPA. One afternoon of work now prevents a $50,000 tax nightmare later. Continue reading

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Crypto Estate Planning Nightmare #8: The Forgotten Account

When “Complete” Isn’t Actually Complete This is the story that reminds us why thoroughness matters. It’s about doing almost everything right—and discovering years later that “almost” isn’t good enough. The Situation: The Model Estate Plan (Or So It Seemed) This … Continue reading

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Crypto Estate Planning Nightmare #6: The Split That Never Rejoined

When Redundancy Becomes Single Point of Failure This is the nightmare that security experts use to explain why “clever” isn’t always “smart.” It’s a story about sophisticated planning that created sophisticated loss. The Situation: The Security Strategy That Seemed Perfect … Continue reading

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Crypto Estate Planning Nightmare #5: The Will That Backfired

When “Making It Easy” Makes It Too Easy This is the story that makes estate planning attorneys cringe. It’s a perfect example of good intentions creating catastrophic results. The Situation: The Fatal Decision The investor thought he was being helpful. … Continue reading

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Crypto Estate Planning Nightmare #4: The DeFi Black Hole

When Invisible Money Stays Invisible This is the story blockchain recovery consultants love to tell—and charge $15,000 to solve. It’s a perfect example of why “crypto-savvy” and “heir-friendly” don’t always overlap. The Situation: Everything Worked, Except the Part That Mattered … Continue reading

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Crypto Estate Planning Nightmare #2: The Encrypted Disaster

When Extra Security Becomes Extra Loss Here’s a story that makes every IT security professional wince. It’s the kind of tale that gets whispered about in blockchain recovery forums, shared in estate planning circles, and used as a cautionary example … Continue reading

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Crypto in Estate Planning, Part 3

Even perfect access means nothing without legal authority. Part 3 shows how to integrate crypto into wills, trusts, and powers of attorney so executors and trustees can act confidently and legally. The focus is clarity—avoiding guesswork, delays, and costly mistakes when it matters most. Continue reading

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Crypto in Estate Planning, Part 2

Knowing your crypto exists isn’t enough—someone has to be able to access it. Part 2 explains how to store seed phrases and private keys securely without locking your heirs out forever. The focus is survivable security: safe from theft, usable in emergencies, and realistic for non-technical executors. Continue reading

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Crypto in Estate Planning, Part 1

Most crypto estate plans fail before they start—because no one knows what exists or where to look. Part 1 explains why crypto requires a simple inventory, how to document wallets and platforms without sharing keys, and how to create a clear “crypto footprint” so your digital assets don’t quietly disappear. Continue reading

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