How Dividend Investing Can Help You Retire Wealthy?

How Dividend Investing Can Help You Retire Wealthy?

Hi, it’s Dre Griggs with Obsidian Wisdom. Today, we’re kicking off our series on dividend investing. Over the next five newsletters, we’ll explore everything from beginner strategies and mindsets to advanced topics like misconceptions and withdrawal strategies.

In this post, we’ll tackle five fundamental questions:

  1. What is dividend investing?
  2. What are dividends?
  3. What is dividend yield?
  4. How do I choose dividend-paying stocks?
  5. What is a dividend reinvestment plan (DRIP)?

Let’s dive in!


What Is Dividend Investing?

Dividend investing involves buying shares in companies that share their profits with investors. These companies, often mature and stable, have more profits than they need to reinvest in their business. Instead, they distribute these extra earnings to shareholders as dividends.

Example: Amazon’s Evolution

In its early days, Amazon reinvested profits into infrastructure, cloud computing, and delivery systems. As companies mature, their reinvestment opportunities decrease. At some point, they start returning profits to shareholders in the form of dividends.

Imagine you and I start a company. Initially, we reinvest profits into better equipment, hiring staff, and training. Over time, we’d reach a point where we have excess profits. To attract more investors and increase our stock’s appeal, we might start paying dividends.


What Are Dividends?

Dividends are the portion of a company’s profits shared with its shareholders. Think of it as an income stream from your investment. For example, if you own rental property, you collect rent without selling the property. Similarly, with dividend-paying stocks, you receive regular income without selling your shares.

Payment Frequency

Dividends can be paid monthly, quarterly, semi-annually, or annually. While most companies pay quarterly or annually, some offer monthly payouts, which can help create a predictable income stream.


What Is Dividend Yield?

Dividend yield is a metric that helps you understand the return on your investment from dividends alone. It’s calculated as:

Annual Dividend / Stock Price = Dividend Yield

For example, if a company pays a $4 annual dividend and its stock price is $100, the dividend yield is 4%.

Avoiding Dividend Traps

Be cautious with unusually high dividend yields. While a 4-5% yield is generally considered strong, a 20% yield might indicate underlying financial issues. Always research why a company is offering such a high yield to avoid falling into a “dividend trap.”


How to Choose Dividend-Paying Stocks

Here are key metrics to consider when selecting dividend stocks:

1. Payout Ratio

The payout ratio shows the percentage of earnings paid as dividends. A ratio above 70% might signal that the company is overextending itself, potentially leading to unsustainable dividends.

2. Dividend History

Look for companies with a consistent track record of paying and increasing dividends. Companies like “Dividend Aristocrats” (25+ years of consecutive payments) and “Dividend Kings” (50+ years) are great starting points.

3. Financial Health

Analyze the company’s debt-to-equity ratio, revenue, and overall financial stability. Think of it like being on Shark Tank—you’re evaluating whether this company is a smart investment.


What Is a Dividend Reinvestment Plan (DRIP)?

A DRIP allows you to reinvest your dividend payouts to buy more shares of the company’s stock. This strategy compounds your investment by:

  • Increasing the number of shares you own.
  • Maximizing long-term capital gains.

Example: Warren Buffett’s Coca-Cola Strategy

Warren Buffett reinvests Coca-Cola dividends to grow his portfolio. Over time, this approach has significantly increased his returns without requiring him to sell his shares.


The Power of Multiple Income Streams

Dividend investing is one of the income streams that 65% of self-made millionaires utilize. By combining earned income, dividend income, and reinvested gains, you create a cycle of compounding growth—what Albert Einstein called the “eighth wonder of the world.”


Final Thoughts

Dividend investing rewards patience, discipline, and thorough research. It provides a balance between income generation and long-term wealth creation. By sticking to your plan and focusing on fundamentals, you can build a sustainable, predictable income for retirement.

Until next time, stay safe and enjoy life!

Dre Griggs


P.S. - Join me live on LinkedIn, Thursday, January 30th for Discover the Strategies to a Secure and Stress-Free Retirement! We'll explore how dividend investing and other proven strategies can help you create sustainable income and peace of mind in retirement. Don’t miss out on insights that could transform your future!

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