CFO Briefing: Year-End Bitcoin Moves To Cut Your Tax Bill

For corporates with meaningful Bitcoin exposure, the year-end can feel less like “tax planning” and more like tax triage. Finance teams are staring at volatile digital asset markets, and a tax calendar that does not care how bullish the board is.

The tradeoff is uncomfortable: pay more than you likely need to, or move quickly in ways that may appear reactive rather than deliberate.

Thankfully, Secure Digital Markets (SDM) can help. As a leading crypto asset dealer, the firm works with digital asset treasury companies, miners, and funds to help them optimize their year-end portfolio construction. They have put together a brief overview on utilizing capital preservation and tax deferral strategies to manage digital asset portfolios.

Solve real problems for your corporate treasury

1. “Unlock Liquidity While Preserving Your Position” Many treasuries hold substantial unrealized gains in BTC and digital assets. However, liquidating these positions to fund capex, buybacks, or runway triggers immediate, significant tax liabilities. SDM provides collateralized lending structures that allow clients to access liquidity without triggering a taxable event in many jurisdictions. This approach helps navigate the math of "borrowing vs. selling" to preserve your core holdings while meeting operational needs.
   

2. “Convert Unrealized Losses into Functional Tax Assets” Many treasuries overlook the opportunity to harvest losses, resulting in unnecessary tax liabilities even when natural offsets potentially exist. SDM facilitates structured tax-loss harvesting to convert "paper losses" into realized tax assets without sacrificing your long-term Bitcoin exposure. The firm provides the execution framework to offset capital gains and optimize your net tax position while maintaining your desired market profile.
   

3. “Discreet Execution & Audit-Ready Reporting” Large-scale treasury adjustments require more than just a liquid market; they require zero market footprint. SDM leverages multi-venue routing and algorithmic order types to absorb high-volume trades without alerting the market and moving the price against you. The firm handles the heavy lifting of executing within narrow tax deadlines and provides a consolidated, auditable record of every trade. 

SDM and its team of specialists can craft a decision framework your CFO and treasurer can use to answer:

• Where does lending make more sense than selling, given our cost of capital and effective tax rate?

• Which loss pockets are genuinely worth harvesting in 2025, and what structures keep us aligned with our Bitcoin thesis?

• How do we document this so that auditors, regulators, and shareholders see risk-managed treasury work, not just opportunistic speculation?

If your company has material BTC exposure and no clear “playbook” for your year-end, this SDM brief is one of the cleaner ways to turn a source of unmanaged exposure into a controlled, board-level win.

If you’d like a session that maps these strategies to your actual positions, jurisdictions, and policies, reply to this email and the BitcoinTreasuries.net team can coordinate a joint workshop with SDM around your year-end calendar.

Contact SDM or visit SDM.co to learn more. Just hit reply, we read everything.

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