You talk the (tax) talk, but can you walk the walk?

The industry loves to highlight the increasing importance of tax management and new tax-focused technology tools, many of them powered by AI. But is tax-savvy financial planning now becoming the norm? Not really, according to a panel at the American College of Financial Services’ Horizons retirement conference in Orlando this week. In fact, the experts found that full implementation of tax services has lagged, and while some firms are excelling, others still don’t understand what they should realistically be building. While the answer will look different for each firm, advisors should be moving beyond annual tax conversations to a “lifetime tax-planning mindset.”

“Managing taxes is like building a house,” said Dave Alison, president of wealth management at Prosperity Capital Advisors. “The first thing you do is hire an architect to draft a blueprint, but that’s only the start of the process.”

Building Blocks

Blueprints, like plans to manage taxes, just collect dust unless you hire someone to do the building and someone to maintain it. “A true tax-planning mindset means advisors are drafting, building and maintaining the house,” Alison added.

If tax planning is like building a house, then the fundamental building blocks are probably strategic Roth conversions, said Jeff Levine, chief planning officer at Focus Partners Wealth. Other “basic materials” would be proactive tax loss harvesting and annual gifting, and there are also more exotic materials to consider, depending on the client’s situation, from the reinvestment of the proceeds of a business sale into a qualified opportunity fund to the establishment of a charitable remainder unitrust. “It’s not just about the tools in isolation,” Levine said. “It’s about moving away from the annual tax bill to considering the lifetime tax bill, or even the multigenerational tax bill.”

Today, most advisors don’t have the knowledge necessary to deliver on this vision, said Kevin Knull, CEO of TaxStatus. They also often lack the necessary data:

• “Clients just don’t remember everything while you’re discussing and building their plan, and the tax returns don’t contain all the information you need,” Knull said.
• Visibility is a major roadblock. For example, direct indexing is a popular strategy today, but getting the most out of the technique (and maintaining legal compliance) requires full knowledge of the client’s investments. “Very few advisors have 100% of a given client’s wallet-share,” Knull said.

An Evolving Approach. “If you’re an advisor going from asset management to tax planning, buckle up,” said Dave McKnight, author and president of Power of Zero. “This is not set it and forget it, even with powerful technology. Given the fiscal state of our country, we also need to plan now for higher tax rates in the future.”

The lines between Silicon Valley and Wall Street are blurring fast.

Both Anthropic and OpenAI, the makers of Claude and ChatGPT, made massive inroads with Wall Street and traditional financial systems this week.

Anthropic announced a $1.5 billion joint venture Monday with Goldman Sachs, Blackstone and Hellman & Friedman to help enterprises adopt AI more effectively. The deal landed Anthropic direct access to hundreds of portfolio companies across PE firms, said Will Trout, Datos Insights’ director of securities and investments. “That’s a distribution moat most [software-as-a-service] vendors would kill for.”

That same day, OpenAI announced raising more than $4 billion from firms including Brookfield Asset Management, Advent and Bain Capital to launch a similar enterprise-focused effort. The premise for both deals is that you can’t wait for enterprises to adopt AI, Trout added. “Goldman Sachs as an anchor investor [is] signaling Wall Street credibility, not just capital.”

Partnership Play

During an Anthropic event Tuesday, CEO Dario Amodei argued that Wall Street’s AI buildout is essential and that SaaS companies that don’t embrace generative tech might not survive. He was accompanied on stage by none other than Jamie Dimon, a huge tell, Trout said. “When the CEO of JPMorgan is publicly excited about a tool, it signals confidence, not just in Claude’s capability, but in the business relationship,” he said. “That’s what these announcements telegraph.”

Other tech companies like Microsoft and Google are also making noise, but they’re not anchoring ventures with PE firms at the same scale. “You need to embed engineers and deployment muscles inside their operations,” Trout said.

Anthropic also announced another partnership this week, alongside new tech rollouts, highlighting the firm’s growing influence on Wall Street:

• On Monday, it revealed a partnership with Fidelity National Information Services that will include building AI tools to investigate money laundering and fraud.
• Anthropic also launched 10 AI agents Tuesday designed to automate routine work across financial services. The tools are aimed at banks, asset managers, and insurers, but could end up benefitting advisors as well.

“Client meeting prep, financial planning, tax-aware rebalancing, tax-loss harvesting, investment proposals, client reports; that is the day-to-day reality of running a wealth practice,” said Jack Morgan, vice president at Rise Growth Partners.

Explain It Like I’m 5. Wealth.com co-founder Danny Lohrfink said AI is “moving from novelty to infrastructure,” noting the potential for more integrated planning. Those insights, however, will need to be easy to explain, govern and use in client conversations. “Faster isn’t enough,” he told Advisor Upside.

All bets are off.

A roll of the dice or a same-game parlay can be thrilling, but it often ends in losses. For the roughly 20 million Americans who report having a gambling problem, per the National Council for Problem Gambling, the behavior can be a hard cycle to break. The ultimate goal for advisors who witness clients with any addictive behavior is to guide them toward professional help. In many cases, wealth managers are among the first to notice something is wrong.

“Clients might feel shame, regret, or like they’re a bad person,” said Dr. Preston Cherry, a CFP and certified financial therapist with Concurrent Wealth Management. “You can’t treat them clinically, but how you speak to them and not judge them can help.”

Judgement-Free Zone

Patterns like large or frequent withdrawals can signal an issue. When raising concerns, advisors should anchor the conversation in the financial plan, showing how certain behaviors conflict with long-term goals like retirement or buying a home. Not every client will be forthcoming, but warning signs appear in account activity. “The stories are in the statements,” Cherry said.

If a client opens up about gambling, advisors should treat it like any other major life event: It’s an opportunity to better support them. “When someone addresses addiction and admits it out loud, that takes real courage,” Cherry said. “They’re looking for a collaborative partner.”

Always in Reach. Gambling itself isn’t new, but the latest mobile apps and online platforms have made betting constant and immediate. According to research from the American Gaming Association:

• All gaming channels, including traditional gambling, sports betting and iGaming reported collective revenues of nearly $79 billion last year, which means Americans lost quite a lot of money.
• iGaming revenue reached nearly $11 billion, while sports betting hit almost $17 billion.
• Americans wagered about $170 billion on sports last year, up 11% from 2024.

“It’s right there in your palm,” Cherry told Advisor Upside. “You may or may not have alcohol in the house. You may or may not have drugs in the house. But the gamification of impulses and addiction are right there on your phone.”