January 17, 2026

tax planning

Nice prompt. Below I’ll translate Michael Saylor’s central idea into a practical, customizable “Strategy for Uniqueness” you can actually use – a framework plus concrete strategy variants and a fill-in template so you can build a plan that fits your go

Build a plan that fits you

Michael Saylor’s idea becomes a practical “Strategy for Uniqueness”: a concise Bitcoin playbook – define objectives, risk, allocation, custody, entry and exit rules, optional active tools, review cadence, plus templates and checklist.

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The Taxman Is Watching: Staying Ahead of the New Rules

The Taxman Is Watching: Staying Ahead of the New Rules

As governments tighten their grip on tax compliance, businesses must adapt to a landscape of evolving regulations. Transparent record-keeping and proactive tax strategies are essential to navigate scrutiny and protect profits in this new era of oversight.

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1. John, 35, invests in Bitcoin through a Roth IRA. He holds for 5 years and sells for a profit of $100,000. He owes no taxes on the gains.
2. Sarah, 40, invests in Bitcoin through a Roth IRA. She holds for 3 years and sells for a loss of $50,000. She owes no taxes on the loss.
3. David, 50, invests in Bitcoin through a Roth IRA. He holds for 10 years and sells for a profit of $200,000. He owes no taxes on the gains.
4. Emily, 30, invests in Bitcoin through a Roth IRA. She holds for 2 years and sells for a loss of $25,000. She owes no taxes on the loss

1. John, 35, invests in Bitcoin through a Roth IRA. He holds for 5 years and sells for a profit of $100,000. He owes no taxes on the gains. 2. Sarah, 40, invests in Bitcoin through a Roth IRA. She holds for 3 years and sells for a loss of $50,000. She owes no taxes on the loss. 3. David, 50, invests in Bitcoin through a Roth IRA. He holds for 10 years and sells for a profit of $200,000. He owes no taxes on the gains. 4. Emily, 30, invests in Bitcoin through a Roth IRA. She holds for 2 years and sells for a loss of $25,000. She owes no taxes on the loss

**Should You Hold Bitcoin in a Roth IRA? Exploring Four Case Studies**

Amidst the rollercoaster ride that is the crypto market, investors are pondering the viability of holding Bitcoin in a Roth IRA. Four case studies offer insights into this complex decision:

* **Case 1:** Anne witnessed Bitcoin’s rise firsthand, reaping substantial profits in her IRA.
* **Case 2:** John invested a portion of his IRA in Bitcoin but encountered significant volatility and losses.
* **Case 3:** Sarah contributed smaller amounts over time and witnessed gradual, tax-free growth.
* **Case 4:** David, nearing retirement, cautiously invested a modest amount in Bitcoin, balancing risk with potential returns.

These case studies underscore the importance of risk tolerance, investment horizon, and the potential for both gains and losses when considering Bitcoin in a Roth IRA.

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