Why does tax planning matter for people who hold both crypto and traditional assets?

There is significant nuance for digital assets that differs from traditional investments and it’s easy to overpay without a coordinated strategy. Digital Ascension Group helps clients integrate crypto and traditional holdings into one proactive tax plan that minimizes taxable events and maximizes after-tax wealth.

Does the IRS treat cryptocurrency as property or currency?

The IRS classifies cryptocurrency as property, not currency. This means every sale, trade, or conversion can create a taxable gain or loss. Digital Ascension Group connects clients with tax professionals who understand how these property rules impact crypto investors and founders.

What is the wash-sale rule, and does it apply to crypto?

The wash-sale rule prevents investors from claiming a loss on a sale if they repurchase the same security within 30 days. Currently, this rule does not apply to cryptocurrency. Digital Ascension Group’s network of tax advisors uses this flexibility to implement compliant, year-round tax-loss harvesting strategies for digital assets.

Can I donate cryptocurrency to charity and avoid capital gains tax?

Yes. Donating appreciated crypto directly to a qualified 501(c)(3) charity allows you to deduct the full market value and avoid capital gains tax. Digital Ascension Group helps clients structure crypto donations and coordinate with donor-advised funds or charitable foundations.

What does proactive tax planning mean?

Proactive tax planning means making strategic financial decisions throughout the year to reduce taxes and align with your goals. Digital Ascension Group helps clients implement strategies such as Roth conversions, tax-loss harvesting, and entity structuring for digital wealth.

Can crypto be held inside an IRA or Roth IRA?

Yes, crypto can be held in certain self-directed IRAs and Roth IRAs. Gains in a Roth IRA can grow tax-free. Digital Ascension Group connects clients with professionals who understand how to properly structure and report digital asset holdings in retirement accounts.

How does Digital Ascension Group work with clients?

Digital Ascension Group doesn’t provide tax or investment advice directly. Instead, it acts as a family office service connecting clients with vetted CPAs, tax attorneys, and advisors who specialize in both digital and traditional wealth management.

What makes tax planning for crypto founders and investors different?

Crypto founders and investors often deal with token vesting, staking rewards, and airdrops—all of which have complex tax implications. Digital Ascension Group ensures clients work with professionals who understand these nuances and can align tax treatment with long-term financial goals.

How can estate planning include digital assets like cryptocurrency?

Estate plans must include secure management and transfer of private keys to heirs. Digital Ascension Group helps families coordinate with estate attorneys and tax experts to ensure digital assets are included in trusts and estate structures.

Why should I start tax planning now instead of waiting until tax season?

Many tax opportunities like harvesting losses, timing Roth conversions, or donating appreciated assets must be executed before year-end. Digital Ascension Group emphasizes ongoing, year-round tax planning so clients don’t miss these critical opportunities.

Keep More of What You Built

Taxes take a bigger bite when you hold both crypto and traditional assets. Most advisors understand one or the other. You need proactive tax planning that addresses your complete financial picture. Digital Ascension Group connects you with professionals who get it.

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 services take 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.

The wash-sale rule that applies to securities doesn’t apply to crypto yet. That matters. Strategic selling and rebuying can offset gains without waiting 30 days. But you need tracking systems that work across wallets, exchanges, and traditional brokerage accounts.

Asset Location Across Multiple 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.

But most advisors don’t think about asset location for digital holdings. They treat crypto as an afterthought held in taxable accounts. Strategic placement of high-growth digital assets in tax-advantaged structures can save six figures over time.

Charitable Giving With Digital Assets

Donating appreciated crypto directly to charity is more tax-efficient than selling first and donating cash. You avoid capital gains and get a deduction for the full fair market value. Most people don’t know this because their advisors don’t track their crypto holdings.

Donor-advised funds can accept crypto. So can certain 501(c)(3) organizations. The paperwork matters, the valuation matters, and timing matters. Done right, charitable giving becomes a core part of your tax strategy instead of an afterthought.

Beyond the Obvious Strategies

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.

Start Building Your Tax Strategy

You built wealth across traditional and digital markets. Now you need tax planning that actually understands both. Digital Ascension Group connects you with professionals who can create strategies that work for your complete financial picture.

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