Income Over Wealth

16 Episodes
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By: Dan Wilson

Practical retirement income strategies from Dan Wilson, an Air Force veteran with over 100 real estate deals. The audio edition of the Retire Early with Dan Wilson YouTube channel: Social Security, taxes, withdrawal strategy, and turning what you've saved into steady income you can retire on. New episodes every Tuesday and Saturday.

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The Surprise Bill That Hits Two Years After You Sell Your House
#14
Yesterday at 3:00 PM

Medicare sets your premium from the tax return you filed two years earlier, so the taxable profit on a home sale can follow you into your first year of coverage. That makes 63 the year that decides your premium at 65, while a sale at 62 lands on a year Medicare never charges you for. This episode covers who actually gets caught, what the surcharge costs in 2026, and what to do before you sell.

The $250,000 and $500,000 home sale exclusion, and why a cap frozen since 1997 now catches ordinary long-time ownersWhat the surcharge costs at each 2026 tier, and the two-year window that...


After 60, Never Share These 6 Things With Your Adult Children
#16
Last Tuesday at 3:00 PM

Most of the money taken from Americans over 60 is taken by someone they already know. That changes what money boundaries with your own family are actually for. This episode walks through six specific things worth keeping to yourself after 60, the mechanism behind why each one backfires, and what to do instead in every case. The point is keeping your retirement under your own control so you can help your kids from a position of strength.

Why adding your child's name to your bank account exposes that money to their creditors and their divorce, and how it can cut...


Why So Many People Die Right After They Retire
#13
08/08/2026

The idea that retirement starts a clock is one of the most repeated fears people carry into it. The studies built to test that idea find no spike in death risk on the day you retire, and the first year looks closer to a honeymoon. What the research does point to is a slower danger, and it shows up for people who leave a job for an empty calendar.

Where the famous "retire at 65, dead by 66" statistic actually comes from, and why the scary version sticks in your head anywayThe habits that keep you out of that group...


How Private Mortgage Notes Work
#15
08/05/2026

If you've ever paid a mortgage, you already understand half of this. Someone on the other end held a piece of paper and got paid every month, with the house standing behind it. This episode walks through how that works when the person holding the paper is an individual instead of a bank, and how to evaluate a note deal yourself before a dollar moves.

The two documents behind every note, and why the recorded one decides who gets paid firstWhat happens when a borrower stops paying, and why the same default takes five months in one state...


7 Things Wealthy Retirees Refuse to Buy (But Poor Ones Do)
#12
08/01/2026

The purchases that drain a retirement plan are rarely the obvious splurges. This episode walks through seven of them, from the oversized house and the new luxury car to the vacation home, the timeshare, and the remodel right before you retire. You get the real math on each one, plus the honest exceptions worth making.

Why the biggest house the bank approves is built for the bank's interest, and the smarter number to buy atThe true weekly cost of a vacation home you use only a few weeks a year, and when renting is the better dealThe one...


Losing Your Job at 60 Can Actually Make You Richer
#11
07/28/2026

Losing a job before retirement can leave you better off than walking away on your own terms. Severance and unemployment only show up when the company ends it, and a single line on your exit paperwork decides whether you collect either one. This episode covers what that paperwork has to say, what to keep quiet about while the package is still in play, and how to turn a funded runway into a bigger retirement.

The difference between fired, laid off, and quitting, and what it does to your severance and unemploymentWhy claiming Social Security the month you lose...


The $300,000 Nursing Home Trap (And How to Avoid It)
#10
07/25/2026

Most families learn how nursing home costs work too late, usually in a hospital hallway. This episode breaks down the two parts of the trap: the Medicare coverage gap and Medicaid estate recovery. It also covers what the healthy spouse gets to keep and why one popular move, gifting the house to the kids, usually backfires.

What Medicare actually covers in a nursing home, the 100-day cliff, and why it pays nothing for daily custodial careHow Medicaid spend-down and estate recovery can put a lien on your "exempt" home after death, and what the healthy spouse keepsWhy gifting...


After 59½, Your IRA Can Do Things Your Brokerage Won't Allow
#9
07/21/2026

This is the plain-English walkthrough of how a self-directed IRA actually works: what it can hold, what it really costs, and the prohibited-transaction rules that keep you safe. You'll see why operating a rental inside one is usually the wrong move, and why secured mortgage notes fit those same rules so well.

Why your IRA can legally hold real estate, private mortgage notes, and private loans, plus the short list of things it can'tThe fee most people never see: how a "free" brokerage IRA can cost more than a self-directed custodian's flat feeWhy running a rental inside an...


The Dark Side of Retiring Abroad
#8
07/18/2026

Retiring overseas gets sold as the move that makes a smaller nest egg work. This episode walks through the costs that don't show up on the cost-of-living blogs: healthcare, US taxes that follow you for life, currency swings, account access, visas and property, and the price of coming home, with the real numbers on each.

Why the Foreign Earned Income Exclusion shelters almost none of a retiree's income, and what you still owe the IRS every year abroadHow dropping Medicare to save money triggers a permanent penalty that can double your premium for lifeThe exchange-rate and account-access traps...


12 Things That Disappear the Day You Retire (Some Are Gone Forever)
#7
07/14/2026

The day your earned income stops, a whole stack of things disappears at once. Some you can rebuild in a year. A few close permanently, and the only time to deal with them is while you still have a paycheck coming in. This episode sorts twelve of them into what you can rebuild and what's gone for good.

Which retirement-account and insurance doors close for good the day your earned income stopsWhy a market loss you'd shrug off while working can turn permanent once you retire, and the income floor that prevents itThe 2026 ACA subsidy cliff (around $62,600 single / $84,600...


Why Smart Retirees Never Pay Cash For a Car
#6
07/11/2026

At a dealership, announcing cash can make you the least profitable customer in the room, which means less movement on the price. This episode breaks down where dealers actually make their money, the finance-then-prepay move that captures the discount without the debt, and the real opportunity cost of draining your capital to pay cash once you're retired.

Why the finance office, not the showroom floor, is where the dealer makes the most moneyHow to use dealer financing to capture a better price, then pay the loan off in week oneThe simple rate spread that tells you when to...


Once Your Portfolio Hits This Number, Saving More Barely Matters
#5
07/07/2026

There are actually three crossovers worth knowing about. The first happens when portfolio growth exceeds your contributions. The second when it exceeds your earned income. The third, the original 1992 Vicki Robin definition, when income from your assets covers your monthly expenses. That last one is the only crossover that survives a flat market year.

Where each of the three crossovers actually sits in dollars (and the rough 20x rule of thumb)Why the original crossover point got quietly redefined between 1992 and 2016The four moves to make once you cross over, especially the RMD trap that hits at 73

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After 55, Never Disclose These 8 Things To Anyone
#4
05/02/2026

Elder fraud cost Americans $81.5 billion in 2024, and a huge portion of it started with something someone said out loud. This episode walks through the eight disclosures that quietly expose you to financial risk after 55, from your retirement timeline to your Social Security amount to the one almost nobody talks about: your "big money" window.

Why announcing your retirement timeline at work often backfiresHow your Social Security amount can make you a target for imposter scamsThe "big money" window right before and after retirement that scammers know exists

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth...


The 6 Wealth Tiers in Retirement (Where Do You Rank?)
#3
04/26/2026

Most people think they're one tier above or below where they actually are. This episode walks through the Federal Reserve's retirement wealth breakdown and shows you what monthly income, daily stress, and real lifestyle look like from the bottom tier to the top 1%.

The net worth range for each of the 6 wealth tiersHow income structure (not just net worth) changes everything at levels 5 and 6How to live like someone 1-2 tiers above where your savings put you

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https...


Got A Pension? Stop Following Normal Advice
#2
04/14/2026

If you have a pension, the usual advice on claiming Social Security, taking a lump sum, or planning survivor benefits was written for people without one. This episode walks through what changed in 2025, the 6% rule for lump sum decisions, and the inflation gap most pensions quietly carry.

How the WEP and GPO repeal changes what pension holders actually collectThe 6% rule for deciding pension vs lump sum payoutThe hidden 45% pension loss from inflation and missing COLAs

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube...


9 Costly Retirement Mistakes People Make After 55 (And Regret Later)
#1
04/11/2026

The mid-50s are where most retirement plans start going sideways, not from a single big mistake but from a pattern of small ones. Chasing a perfect portfolio number. Staying in a job one year too long. Supporting adult children beyond what your plan can absorb. This episode walks through all nine and how to spot each one in your own plan.

Why "one more year" of working often costs more than it earnsThe gift that actually hurts: supporting adult kids past the point it helps themThe one retirement decision you cannot reverse, and how to avoid it<...