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 17, 2026 at 4:43 PM EDT

‘Monopoly Money’: Don McDonald to Colorado Man Pitched $1 Million Annuity With 54% Bonus at Free Steak Dinner

A free steak dinner. A chart with a green line climbing past a red line. A pitch about a $1…

Don Lair | May 17, 2026 at 2:43 PM EDT

I earn thousands yearly from credit card rewards: should I count them as income in my budget?

A listener named Suzanne from Austin wrote into the How to Money podcast with a question I think a lot…

Don Lair | May 17, 2026 at 12:43 PM EDT

Historian: Dividends Were 90% of Returns Until Michael Jackson’s Thriller, Then Everything Changed

Historian and investor Joseph Moore has a way of reframing market history that makes long-time investors blink. On a recent…

Don Lair | May 17, 2026 at 9:40 AM EDT

Buffett Said the Dow Would Hit 1,000,000. Is He Being Too Conservative?

The Oracle of Omaha’s wildest market call has a surprisingly boring math problem behind it In September 2017, the most…

Don Lair | May 17, 2026 at 6:31 AM EDT

Why 19 Income Streams Backfired: The One Side Hustle Strategy That Actually Works

Cody Berman, who appeared on The Personal Finance Podcast in an episode titled “How to RETIRE BY 30! (With Cody…

Don Lair | May 17, 2026 at 5:31 AM EDT

I Make $130,000 a Year Breaking Bones in Motocross. Should I Quit Now?

44 broken bones for $130,000 a year A professional freestyle motocross rider called The Ramsey Show with a simple problem…

Don Lair | May 17, 2026 at 4:31 AM EDT

Why Your Overtime Pay Should Follow the Same 25% Rule, Even When Working Extra Shifts

The paycheck hits fatter after overtime, and the mental accounting starts immediately. That extra $37.41 an hour, plus the time-and-a-half…

Don Lair | May 16, 2026 at 12:31 PM EDT

Your Power of Attorney Can’t Pay Your Bills Without This One Thing: Here’s What to Do Now

Imagine your mother has a stroke. You are her power of attorney. You have her bank passwords written down in…

Don Lair | May 16, 2026 at 11:31 AM EDT

I’ve Been Self-Employed for Seven Years and Finally Made My First Budget: Here’s Why I Cried

A dog trainer from Alaska called into The Ramsey Show recently and almost broke down on air. She had been…

Don Lair | May 16, 2026 at 11:13 AM EDT

Stop Budgeting Your Credit Card Rewards as Income: Here’s the One Move Financial Experts Say Works Instead

On a recent episode of How to Money, a listener named Suzanne asked whether she should track her credit card…

Don Lair | May 16, 2026 at 9:19 AM EDT

The Ghost of Dow 36,000

In the fall of 1999, two writers walked into bookstores with a hardcover called “Dow 36,000: The New Strategy for…

Don Lair | May 15, 2026 at 7:44 PM EDT

I’m 25 with $500k in index funds and 11 rental units generating $3,500 monthly. Am I actually financially independent?

Cody Berman went on The Personal Finance Podcast and described hitting financial independence right before his 26th birthday. He held…

Don Lair | May 15, 2026 at 7:24 PM EDT

Ben Carlson Says Too Many Investment Choices Hurt Your Returns. Here’s How to Say No

Ben Carlson, the Ritholtz Wealth Management portfolio manager and longtime blogger at A Wealth of Common Sense, has built his…

Don Lair | May 15, 2026 at 6:12 PM EDT

I’m 60 with $800k saved and two rental properties. Should I sell one to pay off the other?

Melissa, a 60-year-old listener of the Afford Anything podcast, called in with a clean question: she has $800,000 saved and…

Don Lair | May 15, 2026 at 11:18 AM EDT

I Made $18,000 in ‘Free Money’ Selling Call Options on 200 Tesla Shares: Here’s How the Strategy Works

On a recent episode of the Rich Habits Podcast titled “169: Our Favorite Passive Income Strategy (2026),” co-host Austin Hankwitz…

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Don Lair

‘Monopoly Money’: Don McDonald to Colorado Man Pitched $1 Million Annuity With 54% Bonus at Free Steak Dinner

I earn thousands yearly from credit card rewards: should I count them as income in my budget?

Historian: Dividends Were 90% of Returns Until Michael Jackson’s Thriller, Then Everything Changed

Buffett Said the Dow Would Hit 1,000,000. Is He Being Too Conservative?

Why 19 Income Streams Backfired: The One Side Hustle Strategy That Actually Works

I Make $130,000 a Year Breaking Bones in Motocross. Should I Quit Now?

Why Your Overtime Pay Should Follow the Same 25% Rule, Even When Working Extra Shifts

Your Power of Attorney Can’t Pay Your Bills Without This One Thing: Here’s What to Do Now

I’ve Been Self-Employed for Seven Years and Finally Made My First Budget: Here’s Why I Cried

Stop Budgeting Your Credit Card Rewards as Income: Here’s the One Move Financial Experts Say Works Instead

The Ghost of Dow 36,000

I’m 25 with $500k in index funds and 11 rental units generating $3,500 monthly. Am I actually financially independent?

Ben Carlson Says Too Many Investment Choices Hurt Your Returns. Here’s How to Say No

I’m 60 with $800k saved and two rental properties. Should I sell one to pay off the other?

I Made $18,000 in ‘Free Money’ Selling Call Options on 200 Tesla Shares: Here’s How the Strategy Works

Why Is Institutional Money Pouring Into XRP ETFs While Fleeing Bitcoin and Ethereum?

U.S. Interest Expense Just Hit $1.6 Trillion Annually. Peter Schiff Warns a Dollar Crisis Arrives When It Hits $2 Trillion.

70-Year-Old Couple With $1.8M Just Got a Stage 2 Cancer Diagnosis. Financial Decisions They Have 60 Days to Make

70-Year-Old Couple With $1.8M Just Got a Stage 2 Cancer Diagnosis. Financial Decisions They Have 60 Days to Make

64-Year-Old Tech Exec Holds $1.6 Million in One Stock. The Wrong Move Could Cost $400,000.

Why Is Institutional Money Pouring Into XRP ETFs While Fleeing Bitcoin and Ethereum?

U.S. Interest Expense Just Hit $1.6 Trillion Annually. Peter Schiff Warns a Dollar Crisis Arrives When It Hits $2 Trillion.

Don Lair

‘Monopoly Money’: Don McDonald to Colorado Man Pitched $1 Million Annuity With 54% Bonus at Free Steak Dinner

I earn thousands yearly from credit card rewards: should I count them as income in my budget?

Historian: Dividends Were 90% of Returns Until Michael Jackson’s Thriller, Then Everything Changed

Buffett Said the Dow Would Hit 1,000,000. Is He Being Too Conservative?

Why 19 Income Streams Backfired: The One Side Hustle Strategy That Actually Works

I Make $130,000 a Year Breaking Bones in Motocross. Should I Quit Now?

Why Your Overtime Pay Should Follow the Same 25% Rule, Even When Working Extra Shifts

Your Power of Attorney Can’t Pay Your Bills Without This One Thing: Here’s What to Do Now

I’ve Been Self-Employed for Seven Years and Finally Made My First Budget: Here’s Why I Cried

Stop Budgeting Your Credit Card Rewards as Income: Here’s the One Move Financial Experts Say Works Instead

The Ghost of Dow 36,000

I’m 25 with $500k in index funds and 11 rental units generating $3,500 monthly. Am I actually financially independent?

Ben Carlson Says Too Many Investment Choices Hurt Your Returns. Here’s How to Say No

I’m 60 with $800k saved and two rental properties. Should I sell one to pay off the other?

I Made $18,000 in ‘Free Money’ Selling Call Options on 200 Tesla Shares: Here’s How the Strategy Works

Why Is Institutional Money Pouring Into XRP ETFs While Fleeing Bitcoin and Ethereum?

U.S. Interest Expense Just Hit $1.6 Trillion Annually. Peter Schiff Warns a Dollar Crisis Arrives When It Hits $2 Trillion.

70-Year-Old Couple With $1.8M Just Got a Stage 2 Cancer Diagnosis. Financial Decisions They Have 60 Days to Make

Featured Reads

70-Year-Old Couple With $1.8M Just Got a Stage 2 Cancer Diagnosis. Financial Decisions They Have 60 Days to Make

64-Year-Old Tech Exec Holds $1.6 Million in One Stock. The Wrong Move Could Cost $400,000.