Don Lair

Don Lair writes about options income, dividend strategy, and the kind of boring-but-durable investing that actually funds retirement. He's the founder of FITools.com, an independent contributor to 24/7 Wall St., and a former writer for The Motley Fool.

Don Lair | May 22, 2026 at 6:30 AM EDT

The Counterintuitive Truth That Should Terrify Market Timers: Bo Hanson Explains Why Disciplined Buyers Always Win

Most investors think the worst 25-year stretch in stock market history must have been a financial graveyard. The numbers say…

Don Lair | May 22, 2026 at 6:17 AM EDT

Don McDonald Reveals the Cash Flow Question That Retirees Must Answer First

On a recent episode of Talking Real Money, a caller named Michael from Vancouver, Washington asked the hosts something most…

Don Lair | May 22, 2026 at 5:55 AM EDT

Dave Ramsey’s Baby Steps Work for Most Americans. Here’s When They Might Not

On a recent episode of Smart Money Happy Hour, Ramsey Solutions personalities Rachel Cruze and George Campbell were asked whether…

Don Lair | May 22, 2026 at 5:52 AM EDT

I pay my parents $1,000 a month to babysit but they spend it on toys. Should I invest it for them instead?

On a recent episode of the Rich Habits Podcast titled Q&A: $1.3M IRA, Aging Parents & SpaceX’s IPO, a listener…

Don Lair | May 22, 2026 at 5:45 AM EDT

Dave Ramsey Tells 25-Year-Old With $150k Savings: Pay Off $207k Debt Before Honeymoon

Twelve days before his wedding, a 25-year-old self-employed caller named Joe phoned The Ramsey Show with a question most people…

Don Lair | May 22, 2026 at 5:30 AM EDT

Fannie Mae’s New Crypto Mortgage Program Explained: The $200,000 Collateral Problem

On a recent episode of How to Money, co-host Joel Larsgaard summed up Fannie Mae’s new crypto-as-collateral mortgage program in…

Don Lair | May 21, 2026 at 8:52 PM EDT

How a 21-Year-Old Welder Can Escape a $30,000 Debt Spiral in One Decisive Move

A 21-year-old welder from Mississippi called into The Ramsey Show with a math problem most readers will never see on…

Don Lair | May 21, 2026 at 8:24 PM EDT

Rachel Cruze’s Blunt Truth About Windfalls: Why Most People Waste Settlements Within 3 Years

Nelson from Greeley, Colorado walked up to a microphone at The Ramsey Show‘s live audience event in Denver with the…

Don Lair | May 21, 2026 at 7:36 PM EDT

Bankruptcy in 4 Months or Debt Settlement in 3 Years: Which Path Costs Less

On a recent episode of NerdWallet’s Smart Money Podcast, Budget Rehab: How to Stop Paying Only Interest and Make Real…

Don Lair | May 21, 2026 at 7:11 PM EDT

“Cash in the Long Haul Is Trash”: Why This Money Expert Rejects Traditional Retirement Buckets

Retirement bucket strategies have a way of getting complicated quickly. Don McDonald, co-host of Talking Real Money, prefers a far…

Don Lair | May 21, 2026 at 7:04 PM EDT

The $300,000 Mistake: Financial Advisor Explains Why Waiting to Buy VOO Is Costing You Compounding

On a recent episode of Ramsey Everyday Millionaires titled “How Do I Invest When the News Keeps Shaking the Market?”,…

Don Lair | May 21, 2026 at 7:02 PM EDT

Ramsey Everyday Millionaires: Why Waiting for Markets to “Settle” Usually Means Waiting Forever

The dilemma comes from a caller on Ramsey Everyday Millionaires, but it captures something nearly every investor with a lump…

Don Lair | May 21, 2026 at 10:06 AM EDT

Wall Street is About to Fund the First City on Mars. Here are the Craziest Details from the SpaceX S-1.

Imagine looking at your retirement account and seeing that your money is helping build a city on Mars. That scenario…

Don Lair | May 21, 2026 at 10:01 AM EDT

Worried About a Recession? Here’s Why Selling When Economists Call It is Already Too Late

Andrew Sather of The Investing for Beginners Podcast recently made a point that should reshape how investors think about recession…

Don Lair | May 20, 2026 at 3:20 AM EDT

I Lost Half My Fortune in the Dot-Com Crash at 30. Here’s Why Retirees Can’t Afford That Mistake

The headline is my actual story, and it is the reason I do what I do today. At 19, I…

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Don Lair

The Counterintuitive Truth That Should Terrify Market Timers: Bo Hanson Explains Why Disciplined Buyers Always Win

Don McDonald Reveals the Cash Flow Question That Retirees Must Answer First

Dave Ramsey’s Baby Steps Work for Most Americans. Here’s When They Might Not

I pay my parents $1,000 a month to babysit but they spend it on toys. Should I invest it for them instead?

Dave Ramsey Tells 25-Year-Old With $150k Savings: Pay Off $207k Debt Before Honeymoon

Fannie Mae’s New Crypto Mortgage Program Explained: The $200,000 Collateral Problem

How a 21-Year-Old Welder Can Escape a $30,000 Debt Spiral in One Decisive Move

Rachel Cruze’s Blunt Truth About Windfalls: Why Most People Waste Settlements Within 3 Years

Bankruptcy in 4 Months or Debt Settlement in 3 Years: Which Path Costs Less

“Cash in the Long Haul Is Trash”: Why This Money Expert Rejects Traditional Retirement Buckets

The $300,000 Mistake: Financial Advisor Explains Why Waiting to Buy VOO Is Costing You Compounding

Ramsey Everyday Millionaires: Why Waiting for Markets to “Settle” Usually Means Waiting Forever

Wall Street is About to Fund the First City on Mars. Here are the Craziest Details from the SpaceX S-1.

Worried About a Recession? Here’s Why Selling When Economists Call It is Already Too Late

I Lost Half My Fortune in the Dot-Com Crash at 30. Here’s Why Retirees Can’t Afford That Mistake

Suze Orman to 54-Year-Old With $600,000: Skip the 1.5% Fee and Manage It Yourself

Forget the Labor Market Noise: This Essential Business Utility Stock Is the Ultimate “Set-It-and-Forget-It” Cash Cow

3 Stocks With a Yield Over 6% For Passive Income Investors

Suze Orman to 54-Year-Old With $600,000: Skip the 1.5% Fee and Manage It Yourself

A $2.5 Million 401(k) at 73 Can Still Cost You Six Figures Without These 3 Moves

Suze Orman to 54-Year-Old With $600,000: Skip the 1.5% Fee and Manage It Yourself

Forget the Labor Market Noise: This Essential Business Utility Stock Is the Ultimate “Set-It-and-Forget-It” Cash Cow

Don Lair

The Counterintuitive Truth That Should Terrify Market Timers: Bo Hanson Explains Why Disciplined Buyers Always Win

Don McDonald Reveals the Cash Flow Question That Retirees Must Answer First

Dave Ramsey’s Baby Steps Work for Most Americans. Here’s When They Might Not

I pay my parents $1,000 a month to babysit but they spend it on toys. Should I invest it for them instead?

Dave Ramsey Tells 25-Year-Old With $150k Savings: Pay Off $207k Debt Before Honeymoon

Fannie Mae’s New Crypto Mortgage Program Explained: The $200,000 Collateral Problem

How a 21-Year-Old Welder Can Escape a $30,000 Debt Spiral in One Decisive Move

Rachel Cruze’s Blunt Truth About Windfalls: Why Most People Waste Settlements Within 3 Years

Bankruptcy in 4 Months or Debt Settlement in 3 Years: Which Path Costs Less

“Cash in the Long Haul Is Trash”: Why This Money Expert Rejects Traditional Retirement Buckets

The $300,000 Mistake: Financial Advisor Explains Why Waiting to Buy VOO Is Costing You Compounding

Ramsey Everyday Millionaires: Why Waiting for Markets to “Settle” Usually Means Waiting Forever

Wall Street is About to Fund the First City on Mars. Here are the Craziest Details from the SpaceX S-1.

Worried About a Recession? Here’s Why Selling When Economists Call It is Already Too Late

I Lost Half My Fortune in the Dot-Com Crash at 30. Here’s Why Retirees Can’t Afford That Mistake

Suze Orman to 54-Year-Old With $600,000: Skip the 1.5% Fee and Manage It Yourself

Forget the Labor Market Noise: This Essential Business Utility Stock Is the Ultimate “Set-It-and-Forget-It” Cash Cow

3 Stocks With a Yield Over 6% For Passive Income Investors

Featured Reads

Suze Orman to 54-Year-Old With $600,000: Skip the 1.5% Fee and Manage It Yourself

A $2.5 Million 401(k) at 73 Can Still Cost You Six Figures Without These 3 Moves