There’s two ways that people learn: through personal experience or through someone else’s experience.

That holds true in investing.

I previously shared some of the absolute worst investments I’ve ever made.

While, yes, they were absolutely horrendous (dang penny stock!), those personal investing experiences eventually contributed to the best investments I’ve ever made.

Seeking the advice of others has also helped tremendously.

Best Investments by Other Experts

This has been personal mentors, finance books and blogs, even learning from existing clients.

Taking in their personal experiences and relating it to my own life has contributed to my investing success.

They say “always listen to your elders” and there’s a ton of truth to that.

As part of my latest mission Operation: #investNOW where my goal is to encourage 1 million people to start investing in themselves, I wanted to get real life stories of other investor’s big wins.  (If you haven’t yet, check out what the mission is all about here.)

What I love about the stories shared below is that you see many different ways you can invest in yourself:  stocks, real estate, starting a business, personal development, reading books, and on and on.

Get ready to be inspired to #investNOW.

What was your best investment?

Apple. I purchased shares when Steve Jobs missed Macworld 2009 and shares of Apple fell to around $90 a share. I didn’t own a single Apple product then but I knew they were beautiful, people went nuts for them, and they were constantly innovating. I would sell the shares several years later for around $650 once it became clear other competitors were catching up.

– Jim Wang of Microblogger

* * *

All of my best investments have occurred when absolutely nobody agreed with me and authority figures openly proclaimed me a fool. For example, when I sold all of my investment real estate in 2006 and paid all the taxes (rather than reinvest the gains) not one person supported the decision and industry professionals levied personal attacks against my character. Of course, this was right before the real estate market tanked. I also bought gold stocks in early 2001 shortly after the final bottom following a conversation with John Murphy, the famous technical analyst from CNBC infamy and author of several books, where he said I shouldn’t invest in gold because it wasn’t a free market and the upside was limited because of government manipulation. Of course, all the news was negative for gold, had been for years, and gold stocks promptly rose by several hundred percent.

– Todd R. Tresidder of

* * *

My best investment: I bought Apple shares instead of Apple products long before the iPhones and the iPads!

– MoneyCone of MoneyCone

* * *

The best investment I’ve ever made was in a housing ETF (ticker ITB).  I bought when the housing market was in the toilet and everybody was afraid to invest.  The following year the ETF was up more than 70%.

It underscored for me why passive investors should still invest some in individual stocks and niche ETFs.

– Rob Berger of Dough Roller

* * *

My best investment (as a family) has been in Lowe’s stock through my husband’s retirement plan. He accumulated shares while working there during a high-growth period (he was an employee when the company surpassed one billion in annual sales for the first time). Steady investment in a company that grows typically increases your net worth over time. Getting accustomed to stock price fluctuations (that may not have anything to do with performance) is difficult but necessary.

– Julie Rains of Working to Live Differently

* * *

Paying towards my mortgage. Even though my mortgage rate isn’t tremendously high, every dollar put towards it just gets me a few days closer to having a paid off mortgage. The comfort of knowing that I own my home free and clear will be one of the best payoffs.

– Bob Lotich of Christian Personal Finance

* * *

The best investment I ever made was in GE, I bought when the market was crashing in 2009. It was down to $6.75 and I knew that it was a steal of a deal because they were getting lumped in with the banks. While they suffered some loan losses, I knew it was nothing compared to their other businesses.

– Andrea Travillian of Take A Smart Step

* * *

My best investment probably wasn’t any particular issue – it was just the decision to invest in mutual funds instead of trying to pick (and possibly even trade) individual stocks.

– FF of

* * *

My best long term investment (not a trade) was Monsanto. Love Monsanto or hate Monsanto, it has been a great stock for investors. I’ve actually owned this stock at two different times over the last decade. The first time I bought the stock, it traded at $26 per share, and it went to $80 per share, and then split. It then climbed back to $60 per share after the split, at which point I sold for a great gain. Today I still own the stock again, and I bought it in 2008 during the financial crisis, and it has already returned close to 80% and pays a good dividend.

– Robert Farrington of

* * *

In 1996 I received an unexpected bonus of $1,500. Since it was found money I decided to buy a stock. I really enjoyed the coffee at this new coffee store in Chicago called Starbucks so I bought 50 shares. With splits, I would have 400 shares today, but I was smart and sold some along the way. I’m left with 100 shares worth around $8,000 — a 1,910% return.

– Joel Eggerding of

* * *

Good Timing of an IPO

I bought Tesla Motors for $19/share on their IPO day because I’ve always been a fan of the company. It peaked around $200/share a few months ago but I think it’s a tremendous company that will go far higher over the long-term.

– John Corcoran of Smart Business Revolution

* * *

My best investment has been rolling my ROTH IRA over to Vanguard, investing in their ultra-low cost Admiral shares of the Total Stock Market Index (VTSAX), and maxing out that contribution each year. Minimum fees and expenses and steady growth. I love it.

– James Clear of

* * *

Worked for dot-com company that went public. While the company eventually went bankrupt, I sold my stock options close to it’s peak price. I unfortunately knew too many coworkers who did not do the same.

– Larry Ludwig of Investor Junkie

* * *

I was very lucky to be offered stock options when I started working at a private company. After many years there, the company decided to go public. When the lockout period ended, I decided to buy and hold my options until a better time. Now, I have a substantial amount of money in stocks that I would have never had if I didn’t buy and hold when I did. It is up to me when I cash out and receive my windfall.

– Grayson Bell of Debt Roundup

* * *

I invested in Oracle stock in the 1990’s and sold half of the position after a 500% gain. My only regret was that I didn’t sell the entire position at that time. That was a heady experience and I learned that a big gain can wipe out many small losses. In 2009, during the recent economic crisis, I made a big investment in the Vanguard REIT ETF (VNQ) and tripled my money. Over the years, I’ve learned that investing in diversified index mutual funds in line with my risk tolerance is a much better investing approach than individual stock picking.

– Barbara of Barbara Friedberg Personal Finance.

* * *

Learning Never Gets Old

My single best investment has without a doubt, been in life-long learning — investing in business and investing books, seminars and coaching. In all honesty, that’s a bit self-serving now that I create those types of books and stuff, but there is no other investment that has come close to the same ROI as investing in myself.

– Chuck J. Rylant of

* * *

When I was about two years into college I sold my Disk Man on eBay and got myself an iPod.

It was the greatest thing I’d ever used and not long after I bought a big white clunky Macbook.

I was in love.  In June 2005 I put everything from my OAKMX mutual fund and savings account into AAPL.

I got 40 shares at $70 and the stock split a few weeks later. The rest is history :)

-­ Andrew Fiebert of Listen Money Matters

* * *

The best investment I ever made was the wedding ring I placed on my wife’s hand. The second was that boring little 401(k).

I’ve started saving money in other investments over the years. They all have suffered the effects of the Tech Bubble in 2000 and the Great Recession a few years later. But my investments didn’t disappear, they just dropped for a while. This allowed me to buy more mutual fund shares and realize a huge gain when the market started coming back.

While investing in mutual funds for almost two decades isn’t exciting, the thought of becoming a millionaire in just a few more years is!

Slow and steady wins the race.

– Steve Stewart of MoneyPlan SOS

* * *

“Buying Manhattan real estate in my 20s. My parents thought I was crazy!”

– Sara Stanich of

* * *

The best investment I’ve made has been in a healthy and growing relationship with my wife. The strong marriage and home we have built together allows me to reach for success in all areas of my life

– Sean Nisil of

* * *

Getting Out at The Right Time

The best investment I ever made was Enron, which I sold in the summer of 2000 because it hit a new high and I couldn’t see what would keep it growing. It was as much luck as anything, but I’ll take it.

– Annie Logue of The Root of All

* * *

My best investment is coupled with one of most public failures. I purchased a gorgeous ocean front condo in Rhode Island at the beginning of what I thought would be a minimum 3 year stay. I had JUST enrolled in Law School and decided buying made the most sense. I purchased for $244,000 in July. By December, I knew there was NO WAY I was continuing in Law School. I had made less than $2,000 in improvements in the five months, but managed to sell the property in for 300,000 on the nose. After everything, I walked away with around 40k in profits, but the public humiliation of flaming out of Law School after 1 lousy semester still hurts.

– John Lee Dumas of Entrepreneur On Fire

* * *

The best investment I’ve ever made wasn’t into a bond or a stock – it was an investment of time into getting smarter and wiser about the right way to invest. Reading books and articles and blog posts about investing every day has been transformational for me in a way that no investment purchased in dollars ever could be.

– Joshua M. Brown of The Reformed Broker Blog

* * *

The best investment I ever made was investing in an aggressive portfolio in my 401(k) just after the stock market crashed in 2008. I was buying “at a discount” and have had some massive growth since then.

– Ben from The Wealth Gospel

* * *

It’s a tossup – the .2 bitcoins I mined on a whim win for relative performance, but in terms of absolute dollars a well-timed Bay Area house purchase in 2011 takes the cake. In the stock world, buying GE in March of 2009 was also a good call.

-PK of Don’t Quit Your Day Job…

* * *

Hands down the best investment I’ve ever made was starting my blog. Which, consequently, came out of my *worst* investment

which you’re about to read in a few (my house) 😉 Never did I consider myself an entrepreneur, nor anyone who could successfully work at home or for themselves, but here we are 6 years after that fateful day of shooting out my first post, and it’s been the best thing since to happen to my career.

You’d never think a random “diary” of money could change a life, but it’s amazing the number of possibilities and doors that open just because you’re fluent with how stuff works online (and how it forces you to *think* like a small business owner at the same time). And never are you more connected, and able to network, as you are now with technology both online and off. It’s not everyone’s cup of tea – especially those who flourish on stability – but it’s been an eye opener to say the least.

And I challenge each of you to at least consider the idea of starting up a blog on a topic that you’re passionate about yourself. It only takes a few minutes these days (and it’s FREE!), and you never know where it can take you… Worst case, you just hit delete.

– J Money of Rockstar Finance

* * *

The best investment I ever made was to use dollar cost averaging to buy shares of Coca-Cola and Dr. Pepper Snapple Group through their dividend reinvestment programs (DRIPs). This is a prime example of buy and hold investing and the power of compounding interest.

– Hank Coleman of Money Q&A

* * *

This might sound cheesy coming from a student, but my best investment so far has been that of my education.

I am just starting out in my career, but even just through apprenticeships and co-op work, I doubled my pre-college income.

– Stu of

* * *

My best investment of all time was the $10,000 it initially took to have my first website built. It was a crazy expensive risk, but that site was the vehicle that eventually allowed me to quit my job and become a full-time entrepreneur.

– Nick Loper of SideHustleNation

* * *

Leaving corporate America to start my first franchise in 2001. This has offered me freedom than Corporate America could ever offer.

– Mike Kawula of Self Employed King

* * *

Getting Out in Public

The Best investment I’ve made was in educating myself on public speaking and to start speaking at and attending conferences. I learned the value of networking and as a result I’ve formed valuable relationships that will make an impact on my business for years to come.

– Vernon Ross of The Social Strategy Podcast

* * *

I bought a house for $21,000 in cash, and it rents for $900 per month. That one investment brings me about $5,500 in passive income every year ­­after paying a property manager to handle all the work.

-­ Paula Pant of

* * *

This is going to sound uber-corny, but the best investment I have ever made in myself. I even cringed writing it, but that doesn’t make it any less true. The business I have built exists because of what I have put into it — the words I have written and the actions that I have taken. All of my success to date has been built on a foundation of personal growth.

– Tom Ewer of

* * *

My best investment ever has been choosing low-cost index funds both in my 401k and my Roth IRA, specifically from Vanguard. Actively managed funds are such a rip-off because they take huge percentages as a fee, whether or not you actually have a positive return on investment. Find low cost funds and invest in those. The percentages you’ll keep will make a huge difference over three or four decades.

– Caleb Wojcik

* * *

The best investment I ever made was Limited Brands. I bought shares of Limited Brands after 9/11 when the stock market tanked. I bought for $9/share and sold for over $40/share.

– Jon of MoneySmartGuides

* * *

In 2008, I spent $500 to have an insurance site built for my business. Since then, it has generated over 15,000 life insurance leads and hundreds of thousands of commissions.

– Chris Huntley of eLifeTools

* * *

With the S&P 500 sinking into the ’09 market crash, I scrounged up as much money as I could and bought several companies including LVS which net me a 647% return in 20 months. Buying while everyone else was selling was my best investment so far.

– Jon Petersen of

* * *

Even though it would have been closer to $40,000 had we not refinanced, we made $20,000 when we sold our first house 2 1/2 years later. Definitely our best return!

– Brad Chaffee of Beyond Debt Freedom

* * *

The best investment I ever made was a toss up between real estate and stock. I still have the real estate so that verdict is still out on how that will pan out but it currently looks really good. The stock was an old semiconductor stock called Novellus (NVLS). They have since been bought out. They went from $40 to $180. It was a wild ride. However, I got out too soon!

– Jason of TermLife2Go

* * *

Tumblr was big, as was WildFire.

– Gary Vaynerchuk of

* * *

My best investment was one that I bought and held on to. A little over a decade later, and a few splits and dividends later, and that R.J. Reynolds investment looks pretty good.

– Shane of Beating Broke

* * *

Becoming a Founding Partner of the John Maxwell Team has led me to continually grow myself, giving me greater ability to add value to others, while building a business that helps other solve problems and achieve their goals. After all, if you’re not willing to invest in yourself, why should anyone else?

– Steve Goble of The Goble Group

* * *

A few years ago I put some money into a mutual fund that generally moves with the stock market. It’s not a very flashy choice, but it has increased in value thanks to the steady increase in the stock market over the last few years.

– Benjamin Feldman of the ReadyForZero Blog

* * *

The best investment I ever made was buying low and selling high in the real estate market. The timing of course was key to the success.

– Christopher J. Lalor of Life Insurance Shopping Reviews

* * *

Investing in myself and my business. The money I’ve put into my businesses over the last 5 years has yielded me a 5X return. I have more control over the future of my business that I do with any stock – and we’re just getting started when it comes to growth.

The best investment I ever made was in a life insurance policy. What – are you kidding?? Yes – life insurance. There is a special type of life insurance, that when structured properly, is an excellent way to save money for the future. In 2008, I had no losses in my insurance policy, and the money can be accessed at any time for any purpose, without penalty and taxes.

– Chris Abrams of Abrams Insurance Solutions

* * *

The best investment I ever made was in I bought the stock in late 2008, which to date has generated a return of over 1,500%

-Ian McAuslin of The Life Insurance Journal

* * *

The best investment I’ve ever made was definitely my rental home. I actually lived in it first for three years and then turned it into an investment property. I got it for such a good price in 2009 that I’m majorly cash flow positive every month. Don’t let anyone fool you, rental homes definitely aren’t passive income as some would lead you to believe. But if you hold out for the right property and put in some sweat equity, you too can be a landlord with a nice little side income every month!

– Joel Larsgaard of Save Outside the Box

* * *

Thank You Steve Jobs

My best recent investment involved Apple – specifically some long call options on AAPL. I’m not a terribly active options trader, but I do like to use them to leverage our portfolio. I bought a number of $650 October 2012 calls for AAPL early in the year (when they were trading around $400) and was able to get out around the high of $700. Suffice it to say I was able to realize a very nice gain that was quite a boost to our retirement portfolio.

– John Schmoll of Frugal Rules

* * *

My best investment is one I continue to make. Every paycheck I dollar cost average into Vanguard’s Target Retirement 2050 Fund (VFIFX) in my Roth IRA to fund my retirement. I don’t let emotion enter into the situation and continue to buy more every paycheck so I can retire one day.

– Lance Cothern of

* * *

My best “investment” was deciding to work with a financial advisor. He does what he does best so I can focus on what I do best (writing, not investing!). When markets tanked in ’08, my account actually grew, and I thank him for that.

– Maggie Leyes of

* * *

My best investment my new elliptical machine. Each day I spend about 30 minutes on the machine while I watch TV, surf the web, or listen to audiobooks. Just 30 minutes mild cardio has really changed my life. I sleep better at night, I feel less stressed, and have a ton of energy in the middle of the day.

– Will Chen of WiseBread

* * *

My Best investment was learning about index funds, and why they are so much better than speculating on individual shares. I have now held a growing amount of Vanguard low-fee index funds for about 15 years, and they work peacefully for me day and night, generating dividends and maintaining stability, and stock market crashes and recessions don’t make me nervous at all.

– Mr. Money Mustache of Mr. Money Mustache

* * *

Investing in YOURSELF. I believe investing into yourself as an entrepreneur or business owner will always produce your best rate of return. A close second is overfunded permanent life insurance as it provides a great stable rate of return with protection against loss of capital and also provides the ability to maintain liquidity for reinvesting back into YOURSELF or other investments.

– Ben Newman of

* * *

My BEST investment was choosing to attend Marie Forleo’s RHH Live in 2010. I’d started grad school as a “career move” and was totally hating it. This event changed the trajectory of everything for me – I quit grad school, applied for Marie’s mastermind instead, decided to move back to NYC from Washington DC, ended a relationship, and started my online brand all within 3 months of attending. My entire life changed from one investment.

– Liz Dialto of

* * *

The best investment I ever made was in a plain ‘ol boring S&P 500 index fund. It actually, really, truly outperformed my actively managed funds over the course of a year.

– Leah Manderson of

* * *

Contributing more than I initially felt comfortable saving into my USAA 401(k) when I started here 5 years ago. Given my initially uncomfortable contribution level, the kind markets over this time frame and my investment mix, I’ve now got more money in the account than I could have imagined when I first started.

– Scott Halliwell of USAA

* * *

“My best investment has been Betterment. The best way you can invest your time is in something you care deeply about and makes you happy to come to work every day. I consider my investment of time in this business to be invaluable.”

– Jon of Betterment

* * *

The best investment I ever made was in the stock of the real estate group CB Richard Ellis (CBRE). I noticed that they were the listing agent for many of the vacant commercial properties I was seeing around town after the 2008 crash. I figured, why not invest in the company that should make money once commercial real estate comes back? It was a very profitable rationale.

– LaTisha Styles of

* * *

I’ve been investing in stocks for more than 30 years – including 10 as a Wall Street investment advisor – so I’ve made lots of investments. But the best, by far, is Apple. In 2002, I bought 400 shares for about $3,200, or about $8/share. I sold 200 before the market crash in 2008 for about $165/share, netting $35,000. And I still have 200 today, currently worth north of $100,000.

– Stacy Johnson of

* * *

The best investment I ever made was in my investment knowledge. Taking the time to learn what actually works and what doesn’t has helped me cut through the massive amount of BS that’s out there to make strong long-term decisions.

-Matt from Mom and Dad Money

* * *

My best investment has always been in myself and business, from purchasing coaching to expand my mindset to paying for a conference, that always delivers the best return.

– Jaime Tardy of Eventual Millionaire

* * *

“After writing for years about how having strong family ties is a big part of finding happiness, I realized I am the one who need the advice the most! A couple of years ago, I started making a serious effort to stay more in touch with my parents and sister overseas by visiting/video chatting/calling whenever I can. It still takes conscious effort because they are so far away and life can get in the way, but this is easily the best investment I have ever made.”

– David Ning of MoneyNing

* * *

The best investment I ever made was in a four unit apartment (a bank foreclosure) that I bought for $90,000, using mostly private money to finance the purchase. The property brings in around $2000 per month and should continue to grow each year as rents are raised.

-Brandon Turner,

* * *

Best investment I ever made was to start YNAB. Hands down.

– Jesse Mecham of YouNeedaBudget

* * *

“The best investment I ever made was in my CFP® courses! I started my own company, Gen Y Planning, in May 2013 and I’m a financial planner for millennials. I love being an entrepreneur!”

– Sophia Bera of Gen Y Planning

* * *

The best investment that I ever made was contributing to my 401k. My employer matched a certain percentage of what I put in. That’s FREE money! I would have been crazy not to have taken advantage of that.

-Tai of

* * *

I was fortunate to make plans early in 2013 to invest in myself by attending various conferences. The investment was a sacrifice financially & required some creative adjustments with my day job to take the time off. However, I learned a ton from the events & I met some incredible people that have helped me to create frameworks for accomplishing my personal & professional goals! I would encourage everyone to invest in yourself by growing your personal network by attending conferences.

– Jared Easley of

* * *

Getting Off My Rear

I have two investments that were the best. First was when I finally got off my rear and put money into my company’s 401(k). I put money into an S&P 500 mutual fund. Just making the decision to invest in my future was a great step but what made it better was I started putting money into it when the market tanked from the dot-com crash. I was able to get those early investments at a good discount.

Second was an individual stock that helps keep me going during the week – Starbucks (SBUX). I bought their stock after Howard Schultz came back as their CEO. Since I bought it the stock has more than quadrupled in price and I know that wasn’t all from my coffee purchases 😉

– Glen Craig of Free From Broke

* * *

The best investment I ever made was in a S & P 500 index fund. As boring as that sounds, I have made more money in this fund than any of my individual stock investments.

– Deacon Hayes of


It’s time to invest in yourself. It’s time to #investNOW. Join 1 million others in taking the pledge here.


Get the Money Dominating Toolkit

  • 6 Tools to Get Your Money Back on Track
  • The Ultimate Goal Achiever Workbook
  • 2 Free Chapters to my Best Selling Book
  • 21 Days to Destroy Your Bad Habits Worksheet

Comments | 8 Responses

    • says

      I wonder how many of the “Apple” investors had judged that the future cash flows of Apple exceeded the valuations when they bought and for how many it was a lucky pick!

      I’m really looking forward to my lucky pick!! :)

      There’s some great inspiration in there though. “Starting YNAB” is my favorite. Committing everything to an investment that pays off has to be the most rewarding of all!!

  1. says

    Jeff, I love this article ( and not only because I’m featured). The variety of advice shows how investing can lead to long term wealth.

    Another crucial investing tidbit is that everyone makes investing mistakes, and that’s okay. Because as long as you hang in there with smart money investing strategies, you’re likely to build long term financial security.

  2. says

    I have been following your blog for a couple months now, and it’s been a nice inspiration for my own site focused on wealth building for Generation Y individuals.
    Thanks for this article. I too have had a successful run with AAPL, and am still a proud shareholder. As a value investor, AAPL has plenty of wonderful value characteristics including a huge cash buffer ($160b in cash and investments), a relatively cheap valuation, and an amazing competitive advantage. I’d love to see an article from you on how to pick stocks or ETFs? I think readers would truly benefit from this. Thanks for all you’re doing to educate people financially….very needed today!

  3. says

    Jeff: Thank you for including me on this post. I really appreciate it and shared your blog on facebook. I like your writing style and always enjoy your intelligent and candid advice. Chris

Leave a Reply

Your email address will not be published. Required fields are marked *