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147 Articles

Drew Wood | Jun 19, 2026 at 4:03 PM EDT

The $1 Million Retirement Mistake: Counting Income You’ll Never Get to Spend

A $1 million portfolio is often discussed as though the balance itself answers the retirement question. It does not. What…

Drew Wood | Jun 19, 2026 at 2:56 PM EDT

The Retirement Portfolio That Forks Over a $10,000 Check Every Month

Ten thousand dollars a month works out to $120,000 a year, an income stream that exceeds the roughly $68,359 in…

Drew Wood | Jun 18, 2026 at 11:34 AM EDT

This $2 Million Portfolio Pays a Six-Figure Income Without Owning a Single Rental Property

A $2 million investment portfolio can generate a six-figure income stream without tenants, maintenance calls, property tax surprises, or vacancy…

Drew Wood | Jun 17, 2026 at 11:54 AM EDT

Why Own Rental Property When Dividend Income Can Pay You $10,000 a Month?

A $10,000 monthly income stream is one reason many investors gravitate toward rental real estate. It promises meaningful cash flow,…

Drew Wood | Jun 17, 2026 at 8:59 AM EDT

How to Build $5,000 a Month in Dividend Income and Never Touch Your Principal

Five thousand dollars a month is the income many retirees are trying to generate from their investments. It is enough to…

Drew Wood | Jun 16, 2026 at 2:49 PM EDT

How to Build $3,000 a Month in Dividend Income to Cover the Average Social Security Check

The average retired worker receives roughly $2,000 a month from Social Security. For many retirees, that covers only part of the…

Drew Wood | Jun 15, 2026 at 11:58 AM EDT

This $1.7 Million Portfolio Pays More Than a Member of Congress

A rank-and-file member of Congress earns $174,000 per year. A dividend portfolio can generate the same level of income without…

Drew Wood | Jun 12, 2026 at 5:19 AM EDT

A $310,000 Portfolio That Pays More Than the Rent on a Big-City East Coast Studio Apartment

Rent for a studio apartment in many major coastal cities, including Seattle, Boston, New York, Miami, Los Angeles, and San…

Drew Wood | Jun 11, 2026 at 7:04 AM EDT

A $480,000 Portfolio That Showers You With $36,000 a Year Without Touching Principal

Thirty-six thousand dollars a year sits at the center of many retirement plans. It is roughly comparable to the annual…

Drew Wood | Jun 10, 2026 at 5:05 AM EDT

A $620,000 Portfolio That Pays More Than the Average Social Worker’s Salary

Healthcare social workers earn roughly $68,000 per year on average in the United States, making them one of the higher-paid…

Drew Wood | Jun 9, 2026 at 5:08 AM EDT

Get Paid Like an Indiana Police Officer With $5,000 a Month in Dividend Income After Taxes

Five thousand dollars a month in spendable dividend income works out to $60,000 per year after federal tax, roughly equivalent…

Drew Wood | Jun 6, 2026 at 11:47 AM EDT

How a 73-Year-Old Built a Monthly Paycheck Around O, MAIN, and SPYI

Most 73-year-olds don’t want to babysit twelve positions in retirement. The reader behind this headline has roughly $750,000 in a…

Joel South | Jun 5, 2026 at 9:45 AM EDT

These 4 Dividend Stocks Generate $19,200 Tax-Free Inside a Roth

High earners in the 32% federal bracket holding ordinary-income dividend payers in a taxable brokerage account face a math problem…

Drew Wood | Jun 5, 2026 at 6:56 AM EDT

Replacing a $65,000 Salary With Business Development Company Income? Here’s What You’ll Need Invested

A 62-year-old single retiree seeking to replace a $65,000 pre-retirement salary faces a straightforward but important challenge: generating enough portfolio…

Trey Thoelcke | Jun 4, 2026 at 9:40 AM EDT

Main Street Capital in a Roth IRA: Why the ‘O of BDCs’ Belongs in Your Tax-Free Account

Business development companies (BDCs) pay distributions that are taxed mostly as ordinary income, not qualified dividends. For an investor in…

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Main Street Capital : MAIN

All Main Street Capital Articles

The $1 Million Retirement Mistake: Counting Income You’ll Never Get to Spend

The Retirement Portfolio That Forks Over a $10,000 Check Every Month

This $2 Million Portfolio Pays a Six-Figure Income Without Owning a Single Rental Property

Why Own Rental Property When Dividend Income Can Pay You $10,000 a Month?

How to Build $5,000 a Month in Dividend Income and Never Touch Your Principal

How to Build $3,000 a Month in Dividend Income to Cover the Average Social Security Check

This $1.7 Million Portfolio Pays More Than a Member of Congress

A $310,000 Portfolio That Pays More Than the Rent on a Big-City East Coast Studio Apartment

A $480,000 Portfolio That Showers You With $36,000 a Year Without Touching Principal

A $620,000 Portfolio That Pays More Than the Average Social Worker’s Salary

Get Paid Like an Indiana Police Officer With $5,000 a Month in Dividend Income After Taxes

How a 73-Year-Old Built a Monthly Paycheck Around O, MAIN, and SPYI

These 4 Dividend Stocks Generate $19,200 Tax-Free Inside a Roth

Replacing a $65,000 Salary With Business Development Company Income? Here’s What You’ll Need Invested

Main Street Capital in a Roth IRA: Why the ‘O of BDCs’ Belongs in Your Tax-Free Account

Google vs Apple: Which of the 2 Biggest AI Stocks Is the Better Buy Right Now?

The 20% Tax Credit Developers Use to Flip Historic Buildings and How You Can Claim It

Your RV Qualifies for the Same Mortgage Interest Deduction as a House, but Most Owners Never Claim It

The 20% Tax Credit Developers Use to Flip Historic Buildings and How You Can Claim It

Your RV Qualifies for the Same Mortgage Interest Deduction as a House, but Most Owners Never Claim It

Google vs Apple: Which of the 2 Biggest AI Stocks Is the Better Buy Right Now?

The 20% Tax Credit Developers Use to Flip Historic Buildings and How You Can Claim It

Main Street Capital : MAIN

All Main Street Capital Articles

The $1 Million Retirement Mistake: Counting Income You’ll Never Get to Spend

The Retirement Portfolio That Forks Over a $10,000 Check Every Month

This $2 Million Portfolio Pays a Six-Figure Income Without Owning a Single Rental Property

Why Own Rental Property When Dividend Income Can Pay You $10,000 a Month?

How to Build $5,000 a Month in Dividend Income and Never Touch Your Principal

How to Build $3,000 a Month in Dividend Income to Cover the Average Social Security Check

This $1.7 Million Portfolio Pays More Than a Member of Congress

A $310,000 Portfolio That Pays More Than the Rent on a Big-City East Coast Studio Apartment

A $480,000 Portfolio That Showers You With $36,000 a Year Without Touching Principal

A $620,000 Portfolio That Pays More Than the Average Social Worker’s Salary

Get Paid Like an Indiana Police Officer With $5,000 a Month in Dividend Income After Taxes

How a 73-Year-Old Built a Monthly Paycheck Around O, MAIN, and SPYI

These 4 Dividend Stocks Generate $19,200 Tax-Free Inside a Roth

Replacing a $65,000 Salary With Business Development Company Income? Here’s What You’ll Need Invested

Main Street Capital in a Roth IRA: Why the ‘O of BDCs’ Belongs in Your Tax-Free Account

Google vs Apple: Which of the 2 Biggest AI Stocks Is the Better Buy Right Now?

The 20% Tax Credit Developers Use to Flip Historic Buildings and How You Can Claim It

Your RV Qualifies for the Same Mortgage Interest Deduction as a House, but Most Owners Never Claim It

Featured Reads

The 20% Tax Credit Developers Use to Flip Historic Buildings and How You Can Claim It

Your RV Qualifies for the Same Mortgage Interest Deduction as a House, but Most Owners Never Claim It