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Crypto for Advisors: Bitcoin, IRAs and Tax Prep

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In today’s issue, Bryan Courchesne from DAIM explains how bitcoin can be included in U.S. Individual Retirement Accounts, what to watch out for, and the importance of working with a financial advisor.

Then, Eric Tomaszewski from Verde Capital Management shares tips on preparing for tax season in Ask and Expert.

Sarah Morton

You’re reading Crypto for Advisors, CoinDesk’s weekly newsletter that unpacks digital assets for financial advisors. Subscribe here to get it every Thursday.

Bitcoin Could Be On The Verge Of A Major Breakout: Is Your IRA Ready For The Opportunity?

Top researchers and very large investors are putting price targets on bitcoin that project it is potentially on the brink of a significant bull run. Tom Lee says bitcoin will be $250,000 this year, and Michael Saylor says bitcoin will get to $500,000 overnight.

Imagine having a substantial allocation of bitcoin in your retirement account before this bull run kicks into ultra-high gear – a tax-advantaged allocation funded by an old Individual Retirement Account (IRA) you may have forgotten about. The opportunity is right in front of you, but it’s essential to set it up the right way with a platform that offers comprehensive support and peace of mind.

Step 1: Self-Direct Your IRA Or Work With An Advisor

When investing in bitcoin through your IRA, security and compliance are paramount. A qualified custodian ensures your retirement assets are managed per IRS regulations, offering a layer of protection beyond simple wallet management. If you select a self-directed method, know it will be up to you to handle the transfer and make investment decisions. If you go with an advisor, they will handle the bulk of the transfer process for you, all the way through managing the portfolio.

Self-directing means you have to watch your investments, which are vulnerable to errors, fraud, or mismanagement. An advisor has done the due diligence on service providers and regularly monitors accounts for the best outcome.

Step 2: Set Up Your Tax-Advantaged Crypto IRA

Once you have chosen a self-directed platform or advisor, the next step is signing up, which involves executing and approving a client agreement. While the process is similar for both options, working with an advisor offers critical advantages. An advisor can help design a portfolio tailored to your risk profile, guide you in determining the appropriate position sizes relative to your other investments, and assist in implementing a long-term investment plan that aligns with your financial goals. In contrast, self-directed platforms don’t provide personalized guidance, don’t care what you buy, and are often incentivized to encourage frequent trading, which can erode your returns over time.

Additionally, setting up the correct IRA structure is crucial. For example, if you already have a Traditional IRA, you’ll need to open a new Traditional IRA with the crypto IRA provider to maintain consistency. Transferring assets can be complicated, especially if you’re unsure which investments to sell, how much to roll over, or how to track the transfer process. An advisor can guide you through these steps, handling much of the complexity and ensuring a smoother experience.

Step 3: Invest For Growth As The Crypto Sector Surges

As discussed above, a self-directed platform leaves you on your own to select investments, determine position sizes, and decide when to buy or sell. If you’re confident in your ability to outperform the market and manage these decisions independently, this approach might work for you – but it demands time, expertise, and discipline, with no safety net if mistakes are made.

In contrast, working with an advisor offers a distinct advantage. Advisors provide guidance tailored to your financial goals, help you select high-quality investments, and may offer pre-designed portfolios with proven track records. Rather than going it alone, you’ll gain access to a team of experts whose full-time job is managing digital assets and staying ahead of industry trends.

As many experts predict, the upcoming bitcoin bull run could drive prices well into six figures. By securing a bitcoin IRA today, you can position yourself to benefit from this potential growth while leveraging tax advantages and professional management to support long-term success.

Bryan Courchesne, CEO, DAIM

Ask an Expert

Q. It’s the beginning of a new year. What are some things I should consider so I can kickstart the year effectively?

It’s important to focus on systems more than goals. Goals will give you direction, while systems will create progress. Identify daily and weekly actions that will help you achieve larger goals, personally and professionally. From there, start small, repeat consistently, and tie new habits to existing ones to help you remember and reinforce.

Q. It’s 2025, so what strategies can I use for tax year 2024?

Fortunately, it is not too late to find tax deductions, as there is a range of options to consider. Traditional IRAs, Health Savings Accounts (HSAs), and self-employed retirement plan contributions – such as those made through a SEP IRA or Solo 401(k) plan for freelancers or contractors – are just some of the available options.

Q. How do I tackle an upcoming tax bill in April?

Everything comes back to planning. If you are addressing this situation today, work with professionals to project the needed amount.

From there, prioritize your liquidity needs and goals over the upcoming months while developing a payment plan.

This may require adjusting your budget and exploring creative payment options, such as IRS installment plans, securities-based lending, etc.

Eric Tomaszewski, Financial Advisor, Verde Capital Management

Keep Reading

President-elect Trump is set to host an inaugural crypto ball.

Will Meta’s board of directors consider a bitcoin strategic reserve after being asked by one of the company’s shareholders?

Italy’s largest bank, Intesa Sanpaolo, now owns bitcoin.

Bonus: CoinDesk released a new report, Digital Assets: Q4 Highlights & Commentary

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Chart of the Week: Crypto May Now Have Its Own ‘Inverse Cramer’ and Profits Are in the Millions

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Meet James Wynn, the pseudonymous trader on Hyperliquid who became famous for his $1 billion bitcoin short bet, could now be gaining a new kind of fame: as crypto’s own “Inverse Cramer.”

For those unfamiliar with the Cramer lore: he’s the high-octane, loud-money mascot of CNBC’s Mad Money, a former hedge fund manager turned stock picker with a hit-or-miss track record that turned into a meme. Many retail traders started doing the exact opposite of his recommendations, and the idea became so famous that an “Inverse Cramer ETF” was launched (it was later shut down, but the meme lives on).

Now, crypto traders might have found their new «Inverse Jim Cramer» in James Wynn’s trading wallet.

«The winning strategy lately? Do the opposite of James Wynn,» said blockchain sleuth Lookonchain in an X post, pointing to a trader who has been making millions by doing exactly the opposite of James Wynn’s trades.

Betting against James Wynn. (Lookonchain)

«0x2258 has been counter-trading James Wynn—shorting when James Wynn goes long, and going long when James Wynn shorts. In the past week, 0x2258 has made ~$17M, while James Wynn has lost ~$98M,» Lookonchain said in the post.

Seventeen million dollars in a week just by inverse-betting on one trader is not a bad payday. However, this might be a short-term trade, and one should be very cautious as things can change lightning fast in the trading world, leaving punters millions in losses if not hedged properly.

Even James Wynn said, «I’ll run it back, I always do. And I’ll enjoy doing it. I like playing the game,” after the trader got fully liquidated over the weekend.

So, maybe this Reddit gem: «How much money would you have made if you did the exact opposite of Jim Cramer?» would never translate to include James Wynn. But the sentiments, though, are loud and clear: in a market where perception is half the trade, even your PnL can get memed!

A bonus read: Jim Cramer Doesn’t Know Bitcoin«

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XRP’s Indecisive May vs. Bullish Bets – A Divergence Worth Watching

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XRP, used by Ripple to facilitate cross-border transactions, ended May with signs of indecision. Still, activity on the dominant crypto options exchange, Deribit, suggests that bulls aren’t ready to back down yet.

The payments-focused cryptocurrency formed a «doji» with a long upper shadow in May, a classic sign of indecision in the market, according to charting platform TradingView.

The long upper wick suggests that bulls pushed prices higher to $2.65, but bears stepped in and rejected those levels, driving prices down to near the level seen at the start of the month.

XRP's monthly candlesticks chart. (TradingView)

The appearance of the doji suggests the recovery rally from the early April lows near $1.60 has likely run out of steam. Doji candles appearing after uptrends often prompt technical analysts to call for bull exhaustion and a potential turn lower.

Accordingly, last week, some traders purchased the $ 2.40 strike put option expiring on May 30. A put option offers insurance against price drops.

Bullish options open interest

The overall picture remains bullish, with options open interest concentrated in higher-strike calls in a sign of persistent positive sentiment. Open interest refers to the number of active contracts at a given time. A call option gives the purchaser an asymmetric upside exposure to the underlying asset, in this case, XRP, representing a bullish bet.

«XRP open interest on Deribit is steadily increasing, with the highest concentration of strikes clustered on the upside between $2.60 and $3.0+, reflecting a notably bullish sentiment while the spot price currently trades at $2.16,» Luuk Strijers, CEO of Deribit, told CoinDesk.

XRP's options open interest. (Deribit)

The chart shows that the $4 call option is the most popular, with a notional open interest of $5.39 million. Calls at the $3 and $3.10 strikes have an open interest (OI) of over $5 million each. Notional open interest refers to the dollar value of the number of active contracts.

«XRP option open interest is split across June and September expiries, with monthly notional volumes approximating $65–$70 million, of which over 95% is traded on Deribit,» Strijers said.

The bullish mood likely stems from XRP’s positioning as a cross-border payments solution and mounting expectations of a spot XRP ETF listing in the U.S. Furthermore, the cryptocurrency is gaining traction as a corporate treasury asset.

Ripple, which uses XRP to facilitate cross-border transactions, recently highlighted its potential to address inefficiencies in SWIFT-based cross-border payments. The B2B cross-border payments market is projected to increase to $50 trillion by 2031, up 58% from $31.6 trillion in 2024.

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ETH Price Dips Below $2,500 on Whale Exit Fears, Then Bounces Back Above Key Level

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Ethereum (ETH) faced renewed downside pressure in late trading, tumbling below the $2,500 level as selling volume surged and broader risk sentiment weakened. Global trade tensions and renewed U.S. tariff risks have triggered risk-off flows, with digital assets increasingly mirroring traditional markets in their reaction to geopolitical uncertainty.

On-chain data revealed sizable inflows to centralized exchanges — most notably 385,000 ETH to Binance —a dding to speculation that institutional players may be trimming positions. Although ETH has since recovered modestly to trade around $2,506, market observers are closely watching whether buyers can defend this level or if another leg lower is imminent.

Technical Analysis Highlights

  • ETH traded within a volatile $48.61 range (1.95%) between $2,551.09 and $2,499.09.
  • Price action formed a bullish ascending channel before breaking down in the final hour.
  • Heavy selling emerged near $2,550, with profit-taking accelerating into a sharp reversal.
  • ETH dropped from $2,521.35 to $2,499.09 between 01:53 and 01:54, with combined volume exceeding 48,000 ETH across two minutes.
  • Volume normalized shortly after, and price recovered slightly, consolidating around the $2,504–$2,508 band.
  • The $2,500 level is now acting as interim support, though momentum remains fragile with signs of distribution still evident in recent volume patterns.

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