Nobody likes being left out, but following the crowd brings its own risks.

Perhaps the biggest financial story of 2026 has been the initial public offering of SpaceX, and the pending IPOs of Anthropic and OpenAI, together expected to bring as much as $4 trillion in market cap to US equities over the next six to 12 months. The AI economy hype has some investors rushing into SpaceX stock, with many champing at the bit to buy Anthropic and OpenAI to build a sort of mini-tech index in their taxable brokerage account or IRA. Call it: AI IPO FOMO.

Some financial advisors working with retirement savers have taken a more measured approach, however, telling Retirement Upside that they’re optimistic about the long-term opportunity presented by these companies while also cautious about rushing into single-stock positions. Most say they are happy to wait for these stocks’ eventual inclusion in mainstream indices and diversified sector funds, where their big potential upside and downside risks are balanced with broader holdings.

Patience, Please

One such advisor is Maria Castillo Dominguez, founder of Valoria Wealth Management. The “I’ll miss the early run-up” concern is real, she said, but often overstated, and history shows the best long-term returns have come from stocks after their inclusion in key indices, not before.

“A bundle of high-profile IPOs in an IRA sounds exciting until three of the five underperform and you’ve permanently burned tax-advantaged dollars,” Castillo Dominguez said. “Or your IRA grows to a point where you will have large RMDs in the future, making it imperative to plan for Roth conversions to avoid jumping to a higher tax bracket.”

Other advisors agreed, including Andrew Van Alstyne, founder of High Rock Wealth Management, who worries about early sentiment-trading dragging down performance. “When people aren’t seeing the returns or getting earnings reports that are favorable to what their preconceived notion of these companies is, you’re going to see a lot of people running for the hills,” he warned. “Long term, there will be a place and a time to add these to portfolios, but it’s best for us to sit on the sideline and wait a bit longer.”

Post-IPO performance data from economist Jay Ritter’s famous 1991 paper offers some context:

• IPOs returned 34.5% over their first three years on the market, while comparable companies returned 61.9%.
• The worst results tend to come from young growth companies that went public in hot markets.

Go For Bust! Thomas Rindahl, financial advisor at TruWest Wealth Management, had more of a contrarian take: “If you put 1% or 2% in these IPOs, you could lose it if they all go bust. But is 1% or 2% of your portfolio going to majorly alter your retirement? Probably not. But if they all go 10x or 100x or more, then you could have a significant upside to your retirement.”

Sit. Stay. Now rollover. Good boy!

Proposed guidance from the Treasury Department and the IRS is aiming to simplify the rollover process between retirement plans and individual retirement accounts. Instead of participants carrying much of the administrative burden, the new rules would have recordkeepers shoulder more of the work and facilitate electronic asset transfers. Direct rollovers are already possible, but the proposal would create standardized forms and procedures for financial institutions to coordinate transfers. If approved, the change could save clients potentially dozens of hours of time when rolling over retirement accounts.

“Anything they could do to help would be great because right now, it’s a hellish nightmare,” said Robert Persichitte, an advisor with Delagify Financial. He added that his worst experiences with 401(k) rollovers have involved weeks of phone calls, faxes and even snail mail.

Fill This Out in Triplicate

Those frustrations aren’t unusual. In a 2024 survey from the Government Accountability Office, 25% of participants who had recently completed a plan-to-plan rollover said there were too many steps, while 26% said the process took too much time or effort. Another 20% said their old and new plans did not work together to process the rollover request.

Today, when someone rolls over their 401(k) assets to an IRA, the process typically looks somewhat like this:

• A participant contacts the receiving IRA provider, then their old recordkeeper, and fills out documents and verification forms for both. The old plan may send a check made payable to the new institution to the participant, who then has to forward it to the IRA. And that’s if everything goes smoothly.

Under the proposed guidance:

• A participant requests a rollover through the receiving institution, which communicates directly with the old recordkeeper. The institutions verify the necessary information and transfer the money electronically. No checks required. Bing, bang, boom. You’re in, you’re out.

A rollover can be easy with major custodians like Fidelity, Vanguard or Empower, said Daniel Kopp, founder of Wise Stewardship Financial Planning. However, other custodians can make it extremely painful, and he views it as an asset-retention strategy. “If these firms make it difficult, many clients, including some that I have worked with, just give up and leave assets there,” Kopp told Retirement Upside.

Only If You Want To. The catch is that the proposed standardized process is optional. The Treasury and the IRS are not requiring electronic transfers because doing so would force many institutions to make potentially expensive changes to their recordkeeping systems, said Craig Copeland, director of wealth benefits research at the Employee Benefit Research Institute. “This helps make the process more efficient, but there are still improvements that would make the process even more efficient,” he told Retirement Upside.

There’s no doubt about it: Evaluating Medicare’s alphabet soup of coverage options is challenging. There are Parts A, B and D to consider, plus the Advantage route and the opportunity to source supplemental coverage via Medigap plans, each with its own pricing and coverage dynamics to consider. It’s no wonder 75% of survey respondents said selecting coverage was a confusing and frustrating process, according to eHealth, an online health insurance marketplace.

Despite the challenge, Medicare claiming must be part of the broader retirement planning process because of the significant impact healthcare costs can have on a client’s monthly cash flow, said Whitney Stidom, vice president of consumer enablement at the company. One key decision every retiree must make is whether to go with the all-in-one simplicity of Medicare Advantage or opt for the traditional Medicare route with a Medigap supplement.

Both options have merit, Stidom told Retirement Upside, but the right coverage depends on individual factors such as the client’s health, anticipated medical needs, preferred care providers, travel habits, retirement income and comfort with unpredictable expenses.

Advantage vs. Supplemental

Medicare Advantage, also known as Part C, replaces Original Medicare through private insurers and bundles hospital, medical and (usually) drug coverage with extra perks like dental and vision. Medicare supplement, aka Medigap, works alongside Original Medicare to help cover out-of-pocket costs like copays and deductibles, offering total doctor freedom without networks. Clients cannot have both, so they should consider the following:

• Medicare Advantage makes the most sense if they want low monthly upfront costs and bundled, everyday extras like dental and vision.
• Traditional Medicare plus a supplemental Medigap plan makes sense if they prioritize absolute freedom to choose doctors and predictable healthcare spending without network restrictions.

In practice, Medicare supplement plans are often a superior choice, according to Stidom. “These plans work alongside Original Medicare and cover many of the deductibles, copayments and coinsurance costs beneficiaries would otherwise pay,” she explained. “Although clients generally pay a higher monthly premium than they might with Medicare Advantage, Medicare supplement coverage can make healthcare expenses more predictable.”

Whatever route one chooses, enrollment timing is an important part of the decision. Clients generally receive a six-month Medicare supplement open enrollment period beginning when they are age 65 or older and enrolled in Medicare Part B. During this period, insurers generally cannot deny coverage or charge more based on the applicant’s health history. Afterward, Stidom warned, medical underwriting may apply, and some applicants could pay more or be denied coverage outright.

Don’t Sleep on Advantage. Though preferred by many advised clients, a Medicare supplement is not the right choice for everyone. Medicare Advantage plans may offer lower premiums, for example, alongside bundled prescription drug coverage and additional benefits that Original Medicare does not cover. “Whether beneficiaries are enrolled in a Medicare Advantage, supplement or Part D plan, it is key to comparison-shop plan options every year, specifically during the Medicare annual enrollment period from Oct. 15 through Dec. 7,” Stidom said.