Will AI Replace Financial Advisors? | Dan Pascone with Rob Burgess | EP #45

Rob Burgess is a reporter at Financial Planning magazine, covering investment strategy and advisor technology, AI chief among it. He landed in the industry almost by accident: he started at Wealth Management magazine in October 2022, and ChatGPT launched the very next month. He has been writing about AI's effect on financial advice ever since.

Before that, Burgess spent years as a local newspaper editor in Indiana and managing editor of a legal trade publication, a background in narrow, industry-specific journalism rather than personal finance. That outsider's vantage point is part of why his reporting tends to focus less on the hype and more on what advisors are actually doing with the tools in front of them.

One shift Burgess covers often is advisors expanding well past traditional investment management: estate planning, tax planning, and even concierge-style services once reserved for family offices. He's seen presentations on advisors helping clients buy cars, a service that would have sounded absurd a decade ago.

Dan sees the same pattern from the inside. In the last year alone, Tailored Wealth added several services it didn't previously offer, part of a broader industry move toward a single coordinated relationship instead of a patchwork of specialists. It's the same logic behind the different levels of what a real financial strategy actually requires, most high earners are paying for far less than they actually need. We break that down in Why High Income Isn't Enough: The 5 Levels of Executive Financial Strategy.

Burgess runs a recurring series called Show Me Your Stack, asking advisors what software actually holds their business together. The CRM usually anchors everything: Salesforce is the biggest name, powerful but heavily reliant on customization, while Redtail and Wealthbox are built specifically for the industry. Financial planning software (eMoney, MoneyGuidePro, and RightCapital among the major players) increasingly overlaps with what a CRM does, from document storage to meeting management.

Dan mentioned Tailored Wealth's own recent migration to Salesforce as an example of how much work real integration takes, connecting a CRM, planning software, and portfolio reporting so nothing gets lost between systems. Tools like Zapier and Make have become common glue for stitching a tech stack together, but neither Burgess nor Dan has seen an industry where everything talks to everything else seamlessly yet.

Most of the AI Burgess sees genuinely working sits in the back office: meeting transcription and note-taking tools like Otter, drafting assistance, and prospecting help. The logic is simple: if AI makes a mistake somewhere no client ever sees, someone can catch and fix it before it matters.

The more aggressive end of the spectrum is different. Burgess has interviewed the CEO of a company whose explicit stated goal is to build a driverless car for financial planning: full automation, no advisor required. Whether that vision succeeds or not, it marks a real fork in the industry between advisors using AI to work faster and platforms built to remove the advisor from the equation entirely.

Here's the twist Burgess has found in his reporting: using AI well behind the scenes tends to build trust, but being caught using it visibly tends to destroy it. He points to Morningstar research finding that clients who realize an advisor's email was generated by AI instinctively value that advisor's time less, essentially asking what they're paying for if the advisor won't even write their own message.

Burgess draws a comparison to a McDonald's ad that was pulled after backlash once viewers realized it had been built entirely with AI. The pattern holds across industries: people don't mind AI working quietly in the background, but they resent being shown the seams. For an advisor, that means AI belongs in drafts and prep work, not in anything a client reads as if it came straight from you.

The real dividing line isn't whether an advisor uses AI, nearly all of them do to some degree now. It's what they do with the time it frees up. Burgess has seen the advisors who benefit most reinvest saved hours into more client conversations and more proactive planning, not fewer. The ones who simply automate away their client interactions are the ones losing business to it.

Dan makes the same point from painful experience: hand a new client the keys to a financial planning tool and let them run the projections themselves, and it rarely goes well. The software can model numbers, but it can't ask the follow-up questions that surface what someone actually wants their money to do. That's still a human's job, and it's the entire premise behind a real financial plan instead of a set of outputs.

Burgess and Dan both point to meeting note-takers as the clearest example of AI adding real value. Before tools like this existed, an advisor scribbling notes during a meeting was, by definition, not fully listening. Knowing the conversation is being recorded and will be summarized into the CRM automatically frees the advisor to actually be present.

Dan frames the client-side benefit just as directly: knowing that everything you've ever told your advisor lives searchably in your own file, rather than scattered across someone's notebook and memory, is a genuine upgrade, not a red flag. The same logic applies to your full financial picture. Most people are better served by one coordinated view of their money than a folder of disconnected statements, which is the idea behind Your Money on One Page: A 2026 Operating System.

If you're evaluating a financial advisor in 2026, the CRM or planning software they use matters far less than what it adds up to for you. The right question isn't which tools are in the stack, it's whether they combine into one coordinated plan built around your goals, or a patchwork you end up managing yourself.

That's the same standard we hold ourselves to at Tailored Wealth: technology should buy back time for the parts of planning that still require a human, understanding your equity comp, your tax exposure, and what you actually want your next chapter to look like. We go deeper on what separates real planning value from a commoditized service in Finding a Financial Planner Who Saves and Makes You More Than They Cost.

This episode is for high earners and executives who are either evaluating a financial advisor for the first time or wondering whether their current one is keeping up, along with anyone curious about how much of financial advice AI can realistically replace. If your finances have outgrown a do-it-yourself spreadsheet and a single app, but you're not sure what a genuinely comprehensive, tech-enabled advisor relationship should look like, this conversation is for you.

AI is changing plenty of what happens behind the scenes in financial planning, but the judgment behind a real plan still has to come from a person. If you want a second opinion on whether your accounts, tax strategy, and equity comp are actually working together, a Free Wealth Strategy Call is a low-pressure way to find out