Keep More of What You Built
The Tax Code Wasn't Built for Digital Wealth
You worked hard for your money. You probably built wealth across both digital assets and traditional investments. Now tax season comes around and your accountant looks confused when you mention staking rewards, or they completely miss tax-loss harvesting opportunities because they don’t track your crypto positions.
Filing taxes once a year isn’t enough anymore. Proactive tax planning takes a year-round approach. Think of it like this: reactive tax prep is damage control. Proactive planning is actually building a strategy.
The U.S. tax code has opportunities buried in complexity. If you hold digital assets alongside traditional portfolios, you face unique challenges that require specialized expertise. Digital Ascension Group provides family office services and connects clients with tax professionals through Digital Wealth Partners who understand both worlds.
What Proactive Tax Planning Actually Looks Like
Forget the generic advice. Here’s what working with tax professionals who understand digital assets actually involves.
Tax-Loss Harvesting That Includes Crypto
December 31st isn’t the deadline. It’s already too late. Tax-loss harvesting works year-round when you track both your stock positions and crypto holdings. Digital assets trade 24/7 with higher volatility. That creates more opportunities if someone’s actually watching.
Asset Location Across Account Types
Where you hold assets matters as much as what you hold. Interest income in a taxable account gets hit at ordinary rates. That same asset in an IRA defers taxes completely. Crypto in a Roth IRA grows tax-free. Strategic placement saves six figures over time.
Charitable Giving With Digital Assets
Donating appreciated crypto directly to charity is more tax-efficient than selling first. You avoid capital gains and get a deduction for full fair market value. Most people don’t know this because their advisors don’t track their crypto holdings.
Beyond the Obvious Strategies
The basics get you started. These strategies separate good planning from great planning.
Roth Conversions During Market Dips
Bear markets hurt. But they create tax opportunities. Converting traditional IRA assets to a Roth during a downturn means paying taxes on depressed values. When prices recover, all that growth happens tax-free. Most people miss this because they’re not thinking about taxes when markets crash.
Strategic Withdrawal Timing
You can’t control tax rates, but you can control when you realize income. Spreading gains across multiple years keeps you in lower brackets. Coordinating withdrawals from traditional IRAs, Roth accounts, and taxable holdings requires planning, not panic decisions in December.
Estate Tax Planning for Digital Assets
Private keys don’t transfer like stock certificates. Your estate plan needs specific provisions for crypto custody and access. This intersects with tax planning when you structure entities, set up trusts, or use gifting strategies to minimize estate tax. It’s complicated, and most attorneys don’t get it.
Opportunistic Portfolio Rebalancing
Rebalancing keeps your allocation on target. But timing matters for taxes. Selling winners in a low-income year minimizes capital gains. Rebalancing during losses creates tax-loss harvesting opportunities. This requires coordination between investment decisions and tax strategy.
How Digital Ascension Group Connects You With Tax Expertise
Digital Ascension Group provides family office services for individuals and families holding digital assets. We don’t provide tax advice or investment management directly. That’s not what we do.
What we do is connect you with professionals who actually understand both traditional and digital asset tax planning. Through our relationship with Digital Wealth Partners, you get access to CPAs and tax advisors who’ve worked with crypto founders, high-net-worth investors with complex portfolios, and families navigating multi-generational wealth transfer.
We coordinate the moving pieces. Entity structuring for crypto holdings. Custody solutions that work with your tax strategy. Estate planning that addresses digital assets. Connections to investment advisors who can integrate tax planning into portfolio management.
Your situation is unique. The tax strategies that work for a crypto founder exiting a project differ from what makes sense for a family office adding digital exposure. We start by understanding your complete financial picture, then connect you with the right professionals to build a coordinated plan.
Why Tax Planning Can't Wait
Tax laws change. Your financial situation changes. Crypto markets move fast. Waiting until April to think about taxes means you’ve already lost most opportunities.
Tax-loss harvesting works year-round, but only if someone tracks your positions. Roth conversions make sense during specific market conditions. Charitable giving strategies require planning before year-end. Estate structures take time to implement properly.
The cost of waiting isn’t just what you pay in taxes. It’s what you miss in opportunities. Every quarter without a tax strategy in place is a quarter where you’re probably overpaying.
Maybe your current accountant is great at compliance but doesn’t do strategy. Maybe they know traditional assets but freeze when you mention DeFi yields or NFT sales. That’s not their fault. The field moves fast and specialization matters.