Dividend Investing Success Stories – Volume 1 – How To Get Started

Dividend Investing For Beginners

Dividend investing success stories are a great way for beginners to learn about dividend investing.

Starting out in dividend investing means having a plan to achieve successPin

But I hadn’t figured out the best way to go about presenting stories about successful dividend investing strategies.

But, this is what happened to kick me into gear…

During the Christmas holiday, Mrs. DD and I traveled to Little Rock, Arkansas.  We spent a few days with my wife’s family and had a great time.  That’s nice, but what is the point, you may be asking.

All Dividend Investing Success Stories Start With A First Step

first step of a journey into dividend investingPin

On Christmas morning, I received this email from a reader. This is what he wanted to know…

How To Start Dividend Investing For Beginners…

Hello Tom,

I’m want to get started with dividend stock investing. I know I should have started investing for dividends yesterday, but I didn’t.  So, I want to begin dividend stock investing now. And I want to be a successful dividend investor.

The reason I’m emailing you is that I would like to know how I should start my kids off in dividend investing.  I’m not looking for financial advice, just your opinion.

I have a 13-year-old boy and a 12-year-old girl.  And, I plan on starting 3 dividend investing accounts.  There will be 1 account for me and the other 2 for them.

I plan on starting their accounts with 20% of their Christmas money and some extra money that I provide.

I want this to be an educational journey for the 3 of us for as long as I live, and for them to carry on with their families.

What are your recommendations for getting starting in dividend investing for beginners? I’m guessing we will start each account with $300.

Thank you, I look forward to hearing from you soon!

Merry Christmas!


My Suggestions On How To Get Started As A Successful Dividend Investor

I thought about my response for a while.  And wondered to myself what direction I should go with my suggestions on dividend growth investing for beginners.

First of all, I knew very little about Trent’s financial situation and investment objectives.  Furthermore, I knew is he wanted to become another one of many dividend investing success stories.  Finally, he wanted his kids to learn about dividend investing.

Trent appeared to understand some of the basics about dividend investing and how to be a successful dividend investor as a beginner.

For example. Here are some basic dividend investing concepts that Trent already appears to understand.

What Is Dividend Investing? And Why Invest In Dividend Stocks?

First of all, the focus of dividend investing is to generate dividend income from stocks. Furthermore, to benefit from dividend increases that companies provide to their investors. Finally, to participate in the stock market and benefit from increases in share prices over the long term.

Why Do Companies Pay Dividends?

Companies are in business to make a profit. To make a profit they need capital to invest in their businesses.

One way companies raise capital is through issuing stock to investors in exchange for cash. But, investors desire a return on their investment in these companies.

And one-way companies provide a return to investors is to pay cash dividends.

So, after mulling it over for a while, this is how I responded to Trent about how to get started dividend investing as a beginner.

Dividend-Paying ETFs Are A Good Place To Start Dividend Investing For Beginners

writing to a reader about success in dividend investingPin

Hi Trent,

Thanks for your note.  Sorry for my slow reply.  I was traveling and visiting family over the Christmas holiday.

First, thank you for visiting Dividends Diversify and reaching out.

Successful Dividend Investing Requires A Diversified Portfolio

Regarding your question, I suggest keeping it simple, staying diversified, and investing at regular intervals to get started.

A good high dividend ETF is an excellent choice. With that said, I suggest the Vanguard High Dividend Yield ETF (VYM).  I have personally invested in this ETF for many years.

Alternatively, you could consider the Vanguard Dividend Appreciation ETF.  But, I prefer VYM.  It has a higher dividend yield and very solid dividend growth, historically.

Not necessarily for a beginner, but Vanguard also has a new option for high dividends from international companies.

For Success, A Beginning Dividend Investor Should Invest On A Regular Basis

Make your initial investments.  Then, as money permits, add to your shares periodically.

Monthly contributions are best, but quarterly contributions are okay too.  Just be consistent and add equal amounts of money to the ETF each time.  In this way, you benefit from dollar-cost averaging into the fund.

Beginners Must Think Long Term To Have Dividend Investing Success

Think long-term.  Make sure no one needs the money for at least 5 years.  Since the markets are at all-time highs, they will “correct” eventually and VYM will go down with them.

I would avoid individual stocks when getting started dividend investing.  But, you or your kids might get interested in individual stocks as time passes.

For example, I have been investing in the stock market for 40 years but didn’t get serious about individual dividend-paying stocks until about 15 years ago.  I had more money later in life so it was easier for me to achieve adequate diversification.

I hope this helps and best wishes in 2020!


Learning More About Trent’s Dividend Investing Success Story

And How He Wanted His Approach To Dividend Investing For Beginners

Dividend investing success stories can take different pathsPin

Trent responded promptly.  And from his reply, I learned a little more about how he wanted his dividend investing success story to take shape.  And begin his dividend investing journey. Here is his response…

Hello Tom

Thank you for your reply!

I am enjoying Dividends Diversify. You’re doing a great job with it!

I especially enjoy the stock analysis reports you’ve done.   Blogs like yours are amazing for people like me who want to learn about dividend investing for beginners.  There is so much value.

Thanks for your suggestions.  In January, we are going to tally up our Christmas money and open the accounts.

I’m planning on adding to the accounts automatically through direct deposit through work. Each account will have a set amount of $50 added to it on a bi-monthly basis.

I get quite a bit of overtime, so I’m thinking of having that put into a separate high-interest savings account.  Once I get enough saved I will draw from it to buy individual stocks.

Also, I have another question, if you don’t mind.  When you use a sum of money to buy an individual stock, how many shares do you want to buy? Do you buy 10 at a time, 30, 50, 100, or more?

The logistics of how dividend investing works for creating monthly cash flow is where I need to learn more. In contrast, researching individual companies to invest in is what I enjoy most.

I appreciate any direction you can give.  I’m looking forward to hearing from you again!

Happy New Year!!



Now I Know More About What Trent’s Dividend Investing Success Story Looks Like

I could tell now that Trent was less interested in building a stock portfolio using dividend ETFs.  He wanted to begin dividend investing with individual dividend stocks. 

That’s okay with me.  Now that I knew that fact, I could provide some additional suggestions.  And answer his specific question.

I Offered More Thoughts On Dividend Investing Success And Dividend Investing For Beginners

picking dividend stocks takes time and researchPin

Here is my reply…

Focus On Building A Diversified Dividend Stock Portfolio

Hi Trent,

Diversification is your biggest challenge when getting started dividend investing with individual stocks.

So, build to a 3-5 dividend stock portfolio pretty quickly with the aim of 20-25 eventually.  More stocks are okay but it takes more time and money to manage properly.

Learn How To Pick The Best Dividend Stocks

Start with the best blue chips, like Johnson and Johnson or Hormel Foods (NYSE: HRL) for example.  And do not have all your stocks from the same sector or industry.  You do not want one stock or sector to blow up on you and tank your portfolio.

And understand some of the key dividend stock metrics that will lead to successful dividend stock picks. For each dividend stock, you would like to invest in, review these metrics before investing.

  • Dividend yield
  • Dividend growth
  • Earnings per share
  • Dividend payout ratio
  • Financial position and credit rating

Regarding the number of shares to purchase, it is mostly irrelevant, in my opinion.  You can buy as few as 1 share or as many as you like.

I think of each investment that I make in terms of dollars.  If you start with 3 to 5 stocks, put an equal amount of dollars in each.

For example, you may buy

  • 1 share of stock X at $100 per share
  • 2 shares of stock Y at $50 per share
  • 3 shares of stock Z at $33.33 per share

So, with your first $300 you would then have 3 stocks valued at about $100 each.

As you add money over time, consider which of your current stocks or new stocks represent the best value for your money.

Also, don’t let any 1 or 2 stocks get too large.   Add money to your smallest holdings or add a new holding you do not currently own.

Good luck.  Let me know how it goes.


A Dividend Investing Success Story Gets Its Start

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And that is Trent’s start on his dividend investing success story.  I think there is a lot to be learned from our email exchange about dividend investing for beginners.

Trent asked a lot of excellent questions.  And, I know from my experience as a business school instructor that if one person has a specific question, it is likely that others have the same question(s).

Dividend Investing Success Stories Q&A

But, we are not done with our first dividend investing success story here at Dividends Diversify.

I asked Trent if he would be open to answering a few questions for me and my readers. He graciously accepted. As I said, there is a lot to be learned from what a beginning dividend investor has on their mind.

All of the responses to these dividend investor interview questions were written by Trent.  And proofread by Trent’s wife.

I offer my sincere thanks to both of them for starting their dividend investing success story with Dividends Diversify. And, sharing their beginners’ guide to dividend investing.

Successful dividend investors ask many questionsPin

Here are my questions and Trent’s responses…

Why do you want to begin dividend investing?

I decided to begin dividend investing for 3 main reasons.

  • First of all, I would like to live off monthly cash from dividends at some point when I decide to retire.
  • Furthermore, it is a new hobby that can keep me busy and my mind occupied.
  • Finally, and most importantly, I want to get my kids started.  I wish someone would have done something like this for me at their age.

Right now, my kids do not understand why I am walking around talking about stock prices, percentages, ratios, dollar-cost averaging, and so on.  I think in 20 years they will see how important this time was for them.

This will be a journey we can share forever.  And, possibly create a financial legacy for my kid’s kids, and further.

As a beginning dividend investor, what are your goals and objectives for the money?

Successful dividend investors set goalsPin

My goal is to supplement my retirement with dividends.

I just turned 42, so I’ve got 20 to 25 years left to work.  I would love to retire at 55, but that may be a little difficult.

Right now, I’ve got some extra cash and I’m working quite a bit of overtime. So, instead of spending it, I’m going to make it work for me.  I’d like to see how far things can go.

To buy stocks, you need a brokerage account.   What brokerage company did you choose?  Why?

I chose to go with TD Ameritrade for my brokerage accounts.

I went with TD Ameritrade based on a recommendation from my brother-in-law.  He has used them for several years.

Their reviews seemed to make this a great choice.  They have several more options than some of the other brokerage accounts. They are also cheap, so I get to keep more of my money.

I think the other brokerages are good options as well.  There didn’t seem to be a bad choice. I didn’t want to over-analyze, so I picked one I knew and went with it.

Was it easy to open the brokerage account?  Did you encounter any difficulties with the process?

Opening the accounts was super easy.

I opened 3 accounts, 1 individual brokerage account and 2 custodial accounts for my kids.  I think setting up all 3 took maybe 30 minutes.

The most difficult part was deciding which sweep account to go with.  I’m still not sure what this is, or if I made the right choice.

Once I got all 3 set up, I linked the kids 2 custodial accounts to my account.  In this way, I can control all of them from one sign in.  This was very simple to do.

The next day at work, I set up a direct deposit to each account.  I wish I would have done this many years ago.

What is the first share of stock you plan to purchase?  Why?

My first share will be in the Vanguard High Dividend Yield ETF (VYM).

I set up a direct deposit on all 3 accounts.  With this money, I will be putting it all into VYM once a month.

Any extra cash that I get from working overtime or other income sources will go to individual stocks.  And 20% of any money my kids receive will go into buying individual stocks of their choice.

What other dividend-paying stocks do you have on your watch list?  Why?

This is all new to me, so I will be researching a lot of companies in the future to figure out what I am going to do.

Initially, when I first started looking into dividend investing, I would have told you I want to invest in companies whose products I use daily and that pay a dividend.

So, the following companies are in my daily life.  I will be checking into these companies, but I think my main focus going forward will be blue-chip dividend stocks.

Doing the research is what I’m most interested in.  I enjoy looking for little treasures like the companies and their stocks listed below.

Trent’s Dividend Stock Watch List

You can't replace the human mind when it comes to investment researchPin
  • Ameren (AEE)
  • American Water Works Company (AWK)
  • AT&T (T)
  • Casey’s General Stores (CASY)
  • Honda Motor (HMC)
  • Apple (AAPL)
  • Alphabet (GOOGL)
  • Walmart (WMT)
  • First Busey Corporation (BUSE)
  • Wells Fargo (WFC)
  • Clorox (CLX)
  • Johnson & Johnson (JNJ)
  • La-Z-Boy (LZB)
  • A.O. Smith (AOS)
  • Archer Daniels Midland (ADM)
  • Norfolk Southern  (NSC)
  • CSX Corp (CSC)
  • Target (TGT)
  • Tanger Factory Outlet (SKT)
  • Brinker International (EAT)
  • Pepsi (PEP)
  • Walgreens Boots Alliance (WBA)
  • Proctor & Gamble Co (PG)
  • Techtronic Industries (TTNDY)
  • Home Depot (HD)
  • United Parcel Service (NYSE: UPS)
  • Nexstar Media Group (NXST)

Related: What to consider when picking dividend stocks

Have you discussed dividend investing with your kids and what you are setting off to do with them?

Learn how to involve your kids in investing money in dividend stocks!Pin

I told them we are going to begin dividend investing with our extra money to see how much it will grow when they are older.  I also told them this would be a source of income for them later in life if they leave it alone and keep adding to it.

They don’t really get it right now, but I’m sure they will come around the more involved we get. Both of them were more than willing to give me 20% of their birthday and Christmas money.

I think when they get older and see the money from dividends each month, they will get more excited.

Do your kids have any specific dividend-paying stocks that interest them?

We haven’t gotten that far yet. I need to figure out things a little more before they start telling me what they want.  I don’t want them to make big mistakes because of ignorance on my part.

If I had to guess what they would pick, my son would pick something to do with gaming and shoes.  And my daughter would pick something to do with fashion and social media.

What are your plans for the cash dividends you will receive from the stocks you purchase?

  • Take the cash
  • Reinvest the dividends automatically back in the company that paid them
  • Let the dividends accumulate in cash and reinvest lump sum into a stock of your choosing

Just getting started I am going to have it automatically reinvested in the company that paid them.  I may change my mind on this in the future.

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Dividend Investing Success Story Wrap Up – Dividend Investing For Beginners

This is such a fabulous dividend investing success story as told by a beginning dividend investor.  And I want to thank Trent and his family again for participating. I’m sure they will have many dividend stock investing achievements in the future.

Who would have thought that the email I received from Trent on Christmas morning would result in such an awesome article? And, hopefully, a series of dividend investing success stories moving forward.

To wrap up, here are several dividend investing tips mentioned in the article.  These are the essentials that can lead to your dividend investing success story. Whether you are beginning your dividend investing or are a pro, these tips are valuable.

Dividend Investing Success Stories: Key Points On Getting Started Dividend Investing

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  • Get started – every successful dividend investing journey starts with a first step
  • Time is your friend – begin dividend investing at a young age
  • Low fee dividend-paying ETFs are a great place to earn dividends as a beginner
  • Individual dividend-paying stocks are an excellent option when the time is right – learn how to pick the best dividends stocks
  • Invest equal amounts at regular intervals – dollar-cost averaging
  • Invest in dividend stocks for the long term – at least 5 years
  • We have been in a long bull market – stocks do go down and will go down in the future
  • For each investment – think in terms of dollars, not the number of shares
  • Make sure you have adequate diversification among holdings
  • Living off dividends is attainable – it just takes time and patience
  • Save and invest your extra income from overtime or bonuses
  • To start investing, you need a brokerage account – opening one is easy
  • Use a zero-commission stockbroker to keep trading costs low
  • Every investor should set investment objectives and a plan to achieve them
  • Do your research – know what you buy and buy what you know
  • Create a watchlist
  • There are great rewards in helping your kids invest at a young age
  • Automate investing through direct deposit and other means
  • Reinvest your dividends either a lump sum or automatically in the shares that paid them

Would you like to be featured in an article about dividend investing success stories?  If yes, drop me an email at dividendsdiversify (at) gmail (dot) com.

Tell me a little about where you are at in your dividend investing success story.  You can be a beginner, expert or anywhere in between.  And, we will take it from there.

Further Reading About Dividend Investing Success For Beginners

Author Bio: Tom Scott founded the consulting and coaching firm Dividends Diversify, LLC. He leverages his expertise and decades of experience in goal setting, relocation assistance, and investing for long-term wealth to help clients reach their full potential.

I Hope You Enjoyed The First Of Many Dividend Investing Success Stories

8 thoughts on “Dividend Investing Success Stories – Volume 1 – How To Get Started”

  1. Hi Tom,

    I loved this post and Trent’s story. I have never been more convinced that stocks are one of the best wealth-building vehicles available to individuals, over the long term. And I’m doing just like you and Trent: started in ETFs/mutual funds, and am now branching out into individual stocks.


    • Couldn’t agree more Miguel. I’m glad you liked the story. It was fun working with Trent and putting it together. Tom

  2. This is a nice story, thanks for sharing. Yes, I agree an ETF is the best strategy and dollar cost average, though data shows it is best to dump money in when you have it. I like to DCA as I am cautious.

    Is this the famous Trent Hamm from The Simple Dollar? 🙂 🙂

    • It is an interesting point you make about DCA vs lump sum GYM. I agree with you and am cautious preferring a DCA approach. And no, I think this is a different Trent. Tom

  3. Hey Tom, thanks for sharing the fantastic article. I think you gave great advice to Trent, especially with how you advised to avoid individual stocks at first. Building up a core and then branching out into individual stocks is the way to go.

    • You are welcome. Thanks for visiting Dividends Diversify and learning about Trent’s dividend success story! Tom

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