Your neighbor just told you to max out your 401(k). Your brother-in-law swears by index funds. Your golf buddy won’t stop talking about that AI stock that’s up 200%. And your coworker is doing a Roth conversion because her financial advisor told her to.
Here’s the problem: none of that advice was meant for you.
A suit that fits a six-foot man perfectly doesn’t fit someone built differently — no matter how good it looks. Investing works exactly the same way. What’s right for someone else’s portfolio, tax situation, and retirement timeline may be completely wrong for yours. And yet unsolicited financial advice flows freely at every dinner table, golf course, and office break room in America.
This episode of Simon Says breaks it down by age group — three distinct life stages, three very different sets of priorities — with input from three members of the One Private Wealth team who are actually living in those stages.
Why “One Size Fits All” Investing Is a Myth
The single most dangerous thing you can do with your money is model your investment strategy on someone else’s. Not because they’re wrong for themselves — they might be doing everything right. But because their goals, tax exposure, risk tolerance, time horizon, and income picture are not yours.
A 25-year-old with no dependents and 40 years of compounding ahead should be investing very differently than a 58-year-old with a mortgage, college tuition on the horizon, and retirement a decade away. And both of them should be investing very differently than a 70-year-old managing RMDs, Medicare IRMAA brackets, and a legacy plan for their kids.
The advice that fits one of those people perfectly could genuinely hurt the other two.
Investing in Your Late 30s to Mid-50s: The Accumulation Phase
CFP Brandon Malinckrodt joins the conversation to talk about what matters most for investors in the late-30s-to-mid-50s window — and his answer is unambiguous: this is your mass accumulation phase, and treating it like anything else is a mistake.
It might not feel that way. At this stage of life, money seems to fly out the door — mortgage, kids, cars, college savings. But this is precisely the window where the decisions you make will determine what retirement actually looks like.
Max Out the Right Accounts — Not Just Any Accounts
The obvious move is to contribute to your 401(k). But Brandon flags a trap that catches a surprising number of disciplined savers: over-concentrating in pre-tax accounts.
If your entire retirement savings sits in a traditional 401(k) or traditional IRA, every dollar you pull out in retirement is taxed as ordinary income. That means when you need $20,000 for a trip or a home repair, you may need to withdraw $25,000 or $30,000 just to net what you actually need — and that extra withdrawal stacks onto your taxable income for the year.
The solution is asset location: building a mix of pre-tax accounts, Roth accounts, and taxable brokerage accounts while you still have the time and flexibility to do it. That diversification across account types gives you something genuinely valuable in retirement — the ability to manage your tax burden strategically, year by year, rather than watching every distribution push you into a higher bracket.
Risk Tolerance in Your 40s and 50s: It’s Not One-Size-Fits-All Either
Should you start pulling back on growth and getting more conservative as you approach 50? Maybe. Maybe not.
If you’ve accumulated a strong nest egg and live well within your means, you may actually have more flexibility — not less — because your assets are doing the heavy lifting. Your annual contributions may represent a shrinking percentage of your total portfolio, which changes the calculus considerably.
On the other hand, investors in their mid-to-late 50s approaching 60 should start formalizing a plan — consciously reviewing risk profile, fine-tuning allocations, and thinking clearly about the transition from accumulation to distribution. There’s no universal answer, which is exactly the point.
Teaching the Next Generation While You Still Can
One of the most overlooked responsibilities of investors in this life stage is also one of the most valuable things they can do: sit down with their teenagers and young adult children and start the conversation about money.
If you work with a financial advisor — at One Private Wealth or anywhere else — that advisor should be willing to sit down with your kids even if those kids don’t have much to invest yet. That’s part of what a genuine client relationship looks like. The earlier a young person understands compounding, tax-advantaged accounts, and the danger of chasing trends, the better positioned they’ll be for the next 40 years.
Investing in Your 20s and Early 30s: The Most Powerful Years You Don’t Know You Have
Lindsey Byer, the newest member of the One Private Wealth advisory team, takes on the questions she hears constantly from her own friend group — and they’re exactly the questions you’d expect: student debt vs. retirement savings, Roth vs. traditional, and whether you even need to start investing if you don’t have much money yet.
Student Debt vs. Retirement Savings: You Don’t Have to Choose One
The conventional wisdom is to attack high-interest student debt aggressively before investing. That’s directionally right — but it’s not the full picture.
The smarter approach is to prioritize debt payoff while still contributing at least enough to your 401(k) to capture any employer match. Leaving that match on the table is, in straightforward terms, walking away from free money. Even if all you can manage beyond the match is $50 a month into a Roth, that’s the right move.
Yes, $50. You don’t need a large sum to start. You need time.
The Compound Interest Slide That Every 25-Year-Old Needs to See
The episode walks through a chart that makes the case more powerfully than any explanation could.
Investor one starts at 25, contributing $300 a month. Investor two starts at 35, contributing $600 a month — twice as much. Investor three starts at 45, contributing over $1,200 a month.
Investor one wins. It isn’t close. The ten-year head start that $300 a month buys at age 25 creates a gap that doubled and quadrupled contributions starting a decade or two later simply cannot close. That is compound interest — what some have called the eighth wonder of the world — and it is entirely available to anyone willing to start early and stay consistent.
On Crypto, Prediction Markets, and Chasing Trends
Younger investors do get peppered with the latest shiny objects — crypto, prediction markets, sports betting platforms. And yes, some of that is genuinely popular in certain circles.
But popularity isn’t the same as a sound investment strategy. The discipline that actually builds wealth over a lifetime isn’t finding the next 10x stock. It’s consistent, boring, monthly contributions to low-cost index ETFs, left alone to compound. That’s it. It works. It has always worked. And it works better the earlier you start.
The One Private Wealth Approach: Built for Every Generation
One Private Wealth is intentionally structured across generations — advisors in their 60s, 50s, 40s, and now 20s — because clients’ families span those same decades. The goal isn’t just to serve the client in front of them today. It’s to be a resource for their kids and grandkids as those relationships grow over time.
That’s not a sales pitch. It’s a philosophy about what a long-term financial advisory relationship is actually supposed to look like.
Your Portfolio Should Fit You — Not Someone Else
Whatever stage you’re in — building wealth in your 40s, approaching the transition to retirement in your 50s, or just starting out in your 20s — the most important thing you can do is get advice that’s calibrated to your situation, your goals, and your timeline.
Not your neighbor’s. Not your brother-in-law’s. Yours.
If you’re ready to have that conversation, give us a call at 636-214-1005 or visit our contact page. Whether you’re just getting started or well into your accumulation years, we’d love to talk about where you are and where you want to go.
