“People want to live their money,” Pete Dorsey, financial industry veteran and co-founder of the new AI-based financial planning and investment app, Wing, told me. “They don’t want to just accumulate over time.”
No, they don’t, and that’s inconvenient, considering that perpetual accumulation has been the financial industry’s model for at least a hundred years.
Is this winning the game, or not?
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Let’s face it, the financial industry doesn’t profit from helping people spend their money, but by helping them pile it up. And that’s a shame, because the emotional benefits of accumulation pale in comparison to the joy of intentional living, spending, and giving.
Yet, the fact remains that we do need to accumulate, grow, and protect our assets to fund our spending, however intentional, throughout life. So, perhaps Dorsey (and Wing) is onto something.
Full disclosure: My firm, Signature FD, is one of Wing’s early partners, a decision we made because we believe quality financial advice shouldn’t be the exclusive domain of those with seven-figure portfolios. If technology can help us serve the people who need advice most—not just those who can most easily afford it—that’s an investment worth making.
The Financial Establishment’s Condescension Problem
The financial establishment’s problem starts with our choice of morning beverage, how and where it’s prepared. You’ve certainly received the admonition, implicitly or explicitly, that it’s wasteful to spend $5 to $9 for a coffee or latte or other caffeinated confection when you could simply prepare a similar substitute for pennies on the dollar at home, right?
You’ve also likely heard that you’re among the financially irresponsible if you have a car payment, if your mortgage extends longer than 15 years, or you put less than 20% down on your house, right? But alas, Dave Ramsey’s Total Money Makeover was not divinely delivered via stone tablets on Mount Sinai (and, as it turns out, calling people stupid isn’t the most evolved form of motivation).
The judgement that begins with the financial literacy crowd often doesn’t stop with financial wellness, financial planning, or wealth management, as too often the playbook is merely someone else’s idea of what should be most important to you—rather than a process to help you identify that for yourself and a plan to help you fund it.
Perhaps that’s why Ramsey’s rumored recidivism rate is shockingly high, and studies suggest that as many as 70% to 80% of financial planning recommendations go unimplemented! It’s almost as though financial planning is too often upside down; it starts with someone else’s compulsion rather than your impulsion.
Perhaps one of the reasons this is so common is that financial planning has long been all too retirement centric. Pete and I considered the possibility that retirement was an idea manufactured for a single generation, the Baby Boomers. After all, generations prior pretty much worked until they couldn’t, and subsisted off of Social Security supplemented by modest savings for a relatively short retirement.
Boomers, on the other hand, made out-earning their parents the goal (which they achieved), but too many cornered themselves into jobs they didn’t love in pursuit of a utopian retirement that often didn’t materialize.
Gen X mostly followed that plan, but younger generations have a more morbid view of retirement and are asking more of their work. Money isn’t meaningful enough for them.
The Longevity Wildcard
And that’s ok, because younger generations are likely right to question the norms on working, saving, spending, and living—because they could be living a long time. Dorsey posited, instead of saving for a 10- or 20-year retirement, “how do you plan for a 60-year retirement?”
Perhaps it’s about reimagining the entire relationship between work and life and considering the possibility that learning to “live your money” is an essential skill, not optional.
What Money Actually Represents
Pete Dorsey’s paradox is that money is “priceless and worthless at the same time.” It’s hard to argue literally, as those of us (which is roughly everyone) who use fiat currency are using paper, cards, and online digits that are only worth what everybody else is willing to believe they’re worth. Yet it both runs the world (and our worlds) and carries a very heavy emotional weight with it.
Dorsey referenced a conversation he had with a couple, examining a net worth statement well into seven figures, but the wife was in tears because of the husband’s constant monitoring of every dollar spent. All she wanted to do was shop at Trader Joe’s without fierce examination of every price tag.
“The days of generic one-size-fits-all advice are being replaced,” Dorsey suggests, “by deeply personalized advice that is rooted in people’s relationship with money, their risk tolerance, their aspirations, and their evolving circumstances.”
He insists that this requires “hyper-personalized advice,” that is simultaneously his chief counsel to human financial advisors—to up their EQ game, as so much of the quantitative aspects of financial planning are fast becoming commoditized—and his aspirations for Wing’s AI-assisted platform.
They seek to accomplish this, in part, with a new spin on the notion of goals that the app refers to as “Experiences.” And yes, while you’ll find experiences like “Securing My Retirement” and “Investing My Money,” you’ll also find “Traveling The World,” “Taking A Sabbatical,” and even “Living Like A Nomad,” with more Experiences regularly being added.
The key shift, Pete Dorsey suggests, is that this is a client-led financial plan—not an advisor telling you what you should want.
The Path Forward
The fundamental shift from “Can I afford this?” to “Is this worth trading for something else?” requires both structural support and personal honesty. This means:
- An honest assessment of what truly matters to you
- Visibility into all your financial accounts
- Willingness to prioritize some experiences over others
- Understanding that trade-offs are real: You can do anything, but you can’t do everything
- A regular refresh as life and financial circumstances evolve
The financial industry is slowly, if not grudgingly, learning that accumulation without purpose is just hoarding with a better marketing budget. The future belongs to advice—whether delivered by humans, AI, or likely a hybrid—that helps people live richly at every stage of life, not just in some mythical retirement that may never come, or may last four decades or more. This is, I believe, because people want to live their money. And perhaps, finally, the industry is ready to help them do exactly that.
