Real Estate Deal Analysis & Advice

4 Ways It’s Possible to Speculate in Real Estate (& How to Make Sure You’re Investing Instead!)

Expertise: Personal Development, Commercial Real Estate, Real Estate News & Commentary, Landlording & Rental Properties
75 Articles Written
closeup of casino slot machine

Ever heard of the 17th century Dutch tulip bubble? Tulips had been introduced to Holland from Turkey in the late 1500s. The Dutch people loved them, and within a few decades, their love turned to obsession. Throwing aside all reason, people began “investing” in tulips like there was no tomorrow.

At the height of the market, tulip bulbs sold for as much as six years of an average worker’s annual income. Tulips were trading for the same price as 12 acres of land, and in some cases, for the price of a small estate. Yes, we’re talking about one tulip.

Of course, it all came tumbling down, and the price of tulips eventually returned to the price of a common onion. Thousands of  “investors” lost their homes, their fortunes, and their self-respect.

So what does this have to do with investing?


As a lifelong serial entrepreneur and investor, I have been on a decades-long quest for the perfect investment—or the perfect business—though I wasn’t always aware of it.

  • I invested in oil and gas.
    • ROI: -100%. Lost hours: hundreds.
  • I invested in a wireless internet company.
    • ROI: -100%. Lost hours: a thousand.
  • I invested in and built a nurse staffing company.
    • ROI = 0%. Lost hours: countless.
  • I invested passively with a genius who came up with a scheme to multiply profits through currency exchange. He exchanged his mansion for a 153-year term in the Federal Pen. (He still won’t tell anyone where he hid his 2,000 investors’ $18 million.)
  • I invested in speculative penny stocks with two companies that were about to blow up. They blew up alright, but not in the way I planned.

This doesn’t include a dozen or so other ventures that never got off the ground. Now you know why I recently launched an iTunes podcast called How to Lose Money!

I didn’t fail at everything. My first company, an HR outsourcing firm, was quite successful. My partner and I sold the firm for nearly $3 million after five years, and I was two-time finalist for Michigan Entrepreneur of the Year along the way.

But this initial success and profit led me to a series of entrepreneurial ventures and investments that sent me back to school for a decade and a half. This school was harder than my engineering degree, more challenging than my MBA, and more costly than I would have ever imagined.

I tried one venture and investment after another, largely losing time and money—until I learned the power and profit of real estate investing.

It was 2001, and I had burned through a lot of the proceeds I had made in the sale of my company. My friend and I, mostly on a whim, attended a real estate auction on the courthouse steps in Martinsville, Va. We were the only bidders that day, and we paid $34,000 for a home assessed at $65,000.

The great news was that it only needed a coat of paint and a good cleaning. We sold it by noon the same day we stuck the FSBO sign in the yard.

This began a multi-decade career investing in over 60 house flips, dozens of high-end waterfront lots, modular homes, rental homes and trailers, two subdivisions, a Hyatt hotel, a multifamily community, a workforce housing marketing firm, an online real estate portal, and a multifamily investment firm. Though I’ve had a few losses along the way, overall I’ve learned that real estate investing is a predictable, powerful, and stable source of income and long-term wealth creation and preservation.

Are You Investing or Speculating?

“Investing should be more like watching paint dry or watching grass grow. If you want excitement, take $800 and go to Las Vegas.” —Paul Samuelson, First American Winner of Nobel Prize in Economic Sciences

Want more articles like this?

Create an account today to get BiggerPocket's best blog articles delivered to your inbox

Sign up for free

After starting off so well, why did I fail so often in investing? Was I really investing at all? Or was my investing more like a trip to Vegas without the dancing girls?

I failed because I confused my speculating with real investing.

Some of the world’s most successful investors use a theory call “value investing.” Value investing was conceived by Benjamin Graham and David Dodd in their 1934 book Security Analysis. Though focused on stocks, their theories applies to all types of assets.

The authors make the distinction between investors and speculators. Graham and Dodd said, “An investment operation is one which, upon thorough analysis, promises safety of principal and an adequate return. Operations not meeting these requirements are speculative.”

So I boil it down this way:

  • If you’ve done a thorough evaluation and you’re reasonably sure your principal is safe—and you have a chance to make a profit—you are investing.
  • If you are “investing” in an asset that has uncertain protection of principal—and you have a chance to make a profit—you are speculating.

I am sad to say that many of my investments over the years were nothing more than speculating. I might as well have gambled away my hard-earned cash at Vegas tables.

Is it okay to speculate? Of course, as long as it’s clear in your mind that you’re doing so. Millions of people have made billions of dollars investing in little startup companies like Apple, Microsoft, and Airbnb. But the overwhelming majority of speculators lose their money, their time, their energy, and sometimes their relationships and health.


Related: Why Investing in Real Estate Just for the Tax Breaks Can Be Unwise (& Downright Dangerous)

Unlike many asset classes, real estate provides an opportunity to invest rather than speculate.

  • Chosen wisely, real estate provides a safeguard on principal.
  • In many cases, real estate has a high likelihood of producing an ongoing profit.
  • In carefully chosen locations, real estate is likely to appreciate in value.

I told you earlier about how I lost money in all types of businesses and investments. Since I started investing in real estate, I’ve had the opportunity to:

  • Make up to $100,000 a piece flipping overgrown waterfront lots before the crash.
  • Average over $20,000 per flip on over 60 houses.
  • Make a 55% profit on a subdivision I developed.
  • Provide stable ROIs to many investors in projects I’ve sponsored.

Real estate investment has been good to me, and I would never trade it for any other profession.

4 Ways It’s Possible to Speculate in Real Estate



Let me count the ways…

1. Market Selection

Poor market selection can be a form of speculating. I recall getting a “screaming deal” on a house in Ridgeway, Va., in 2001. Not only was it rural, but the recently departed textile industry left them with an unemployment rate of about 22 percent.

Needless to say, I didn’t make a killing on that deal. But even so, I survived, got almost all my principal back, and lived to see another day. Many high tech speculators only dream of getting out that well.

2. Asset Selection

You can overpay or overspend on upgrades for a property. You can buy an asset with structural problems. You can fall in love with the style of a home and overestimate its resale value. All of these are forms of speculation.

I have done all three. But again, I got out of all three OK.

  • I over-spent on upgrades for a home I recently flipped. Rehab budget was $80K, but we went overboard finishing the basement and more, and spent over $100K. The damage: I made $16k profit rather than the $40K or so we hoped for.
  • I bought a home with hidden structural problems. We chose to forego a pre-purchase inspection and closed quickly to get a better deal. We later spent $10 or $12K on basement wall repairs. The damage: We still made over $20,000 in profit.
  • I once fell in love with a charming Cape Cod in need of significant upgrades. I didn’t know the area well (this was 2001 and I was new at this), and the resale was far less than I’d hoped. The damage: We lost about $3,000 on it.

Do you see the trend here? Even when speculating in real estate, the underlying value of the asset sometimes mitigates losses. I made over $30,000 in total profit on these three speculative mistakes.

Speculating in stocks or precious metals or startups or oil and gas rarely fares so well.

I’ve invested in gold and silver three times in my life, and I lost tens of thousands. I invested $92,000 in a tech startup that didn’t work. I invested $75,000 in an oil and gas deal that came up dry. (My petroleum engineering degree didn’t help there.) Real estate investing has been better for me and most people I know.

3. Timing

You can speculate on timing. All real estate is local. So I wouldn’t say, “The real estate market is in a bubble.” I may say, “The San Francisco market is in a bubble.” It is possible to speculate by buying too high in the wrong market.

My friend Mike made his first foray into rental real estate after college in the late ’80s. He and his three friends went in on a Bay Area house that had doubled (or tripled?) in price over the previous years. Five bedrooms for $500,000 sounds cheap for San Fran today; however, that was pricey three decades ago. But they felt secure in knowing how fast prices were climbing.

Then the bottom dropped out.

My friend and his partners lost their money and their home.

I bought my first home in metro Detroit about that same time for $50,000 and sold it a few years later for $55,000. I was happy with my 10 percent, especially after hearing Mike’s story.

Thoughtful hopeful African American employee looking at computer laptop screen, waiting hoping, person holding hands in praying position, expecting trouble solution, positive result, close up portrait

Related: Expecting Appreciation is a Game For Speculators, Not Long-Term Investors

4. Speculative Development

Real estate developers are among the wealthiest folks on the planet. Or perhaps I should say, “Some of the wealthiest folks on the planet are real estate developers.” Some of the brokest are, too. (Is that a word? It should be.)

While many developers are uber-successful, there are probably many more who have gone broke and have moved on to higher paying jobs now, like delivering pizza. And many developers who succeeded wildly in one market cycle lost all that and more in the next.

Do you want to be a developer? Go for it. I’ll cheer you on. But realize that the stakes are very high, and you’ve left the safety zone of many other real estate investments. You’ve definitely entered the speculation zone. (It’s like The Twilight Zone, but it’s even scarier.)

You may protest: “Paul, didn’t you say you made a 55 percent profit on your subdivision?”

Yes, that’s true. But I’m going to be honest and tell you that I didn’t really calculate the significant risk I was bearing. I almost lost my shirt in that deal, and I could have easily landed in bankruptcy court. I would never knowingly take on that level of risk again—not for me and especially not for my investors.


Sometimes you only see your path clearly in the rear view mirror. I am currently involved in one of the safest, most stable, profitable real estate classes on the planet—syndicated commercial multifamily investing. And I look pretty wise to the young guys in my sphere of influence. (Don’t show them this article. They think I’m pretty smart.)

But my path was riddled with mistakes and risks and miscalculations. I spent years thinking I was investing, while I might as well have been pulling the handle on a slot machine. I plan to never confuse speculation for investing again. Especially when I am handling other people’s money. And mine. And my children’s and future grandchildren’s.

You don’t have to make the mistakes I made. You can stand on my shoulders, renounce speculation, and invest wisely to create a multi-generational wealth-creating real estate empire.

Have you ever confused speculating with investing? Do you see this happen amongst inexperienced investors in your market?

Let me know your experiences with a comment!

After graduating with an engineering degree and then an MBA from Ohio State, Paul started on the management development track at Ford Motor Company in Detroit. After five years, he departed to star...
Read more
    Replied about 3 years ago
    Thanks for the post and thanks for being honest about your \”education\”. Sometimes I think everybody on Bigger Pockets is a friggin genius or just plain lucky. Glad to know others have had a real world experience. After corporate America I tried a few things (including currency trading. Only lost $1000 and I feel lucky). I settled on real estate and have been doing it since 2002. I buy a few houses a year, fix them up, rent them out, sometimes I \”flip\” them, but usually hold. NOw, I have 42 doors, all cash flow positive. I bought property in 2007 at the peak of the bubble. Guess What Guys: You only lose when you sell. I took these two houses, rented them out at positive cash flow, sold one of them for a profit and still have one of the houses I bought at the peak. I could sell it for a decent profit, but I am holding it. Two big mistakes: I invested a 6 figure amount with a developer who promised me a 12% return. Turns out he was very over leveraged and I lost the entire investment. Now, I am a control freak that checks everything out 1000% before I invest and to date, I only invest in my projects. Easy money is never easy. When I turn 80, I am going to have to buy notes or something because I will done with landlording, but for now, I want to completely control what I own. 2nd mistake, maybe even bigger. I should have bought more property during the downturn. 3 bedroom brick ranch houses were selling for $35,000 4 and 5 years back. They needed work, but they made great rentals and flips. My contractor was only able to rehab houses every 3 months. I should have found an additional guy, but breaking in a new contractor is very tough. I wish I would have bought 10 more houses. Investors are now paying 3 times as much for the same house. The rental amount is maybe 100 bucks more a month, so the cash flow has declined. Still looking for decent deals. They are out there, but the supply of basically free houses is going away fast. Thanks Paul for your post.
    Paul Moore Investor from Lynchburg, VA
    Replied about 3 years ago
    Gary, Thanks for your excellent comments. I completely agree. I have lost most money when I handed it to others to manage. I’m glad I’m not alone. I wish I would have been in tune with rental housing at the bottom of the recession. Instead I was just trying to survive. (I will be writing about that experience soon.) I am glad you are doing well, and I wish you continued success! Thanks, Paul
    Mike Dymski Investor from Greenville, SC
    Replied about 3 years ago
    Great article Paul and great reply Gary. The school of hard knocks can lead to great wealth and, more importantly, the confidence and ability to deal with any challenge in life.
    JL Hut Investor from Greenville, Michigan
    Replied about 3 years ago
    Great one Paul, thanks for sharing. I have been there and done most of that, the good and the bad. The best investment is Real estate bought low and held forever with positive cash flow. It has held me up above water for 34 years.
    Paul Moore Investor from Lynchburg, VA
    Replied about 3 years ago
    Thanks JL. I was just telling one of my business partners that I wish I would have held so many of the properties we flipped over the years. I would have amazing cash flow. I think you are right.
    Audrey Ezeh Real Estate Investor from Las Cruces, New Mexico
    Replied about 3 years ago
    Thank you Paul!
    Paul Moore Investor from Lynchburg, VA
    Replied about 3 years ago
    Thank you, Audrey!
    John C. Investor from New York, NY
    Replied about 3 years ago
    Thanks for your honesty and humility, Paul. And thanks for the free book! We hear about the success stories on BP way too often. We rarely hear of the ugly side of REI and other investments. This serves to keep things in check.
    Paul Moore Investor from Lynchburg, VA
    Replied about 3 years ago
    Thanks so much, John! My wife thinks I’m crazy to pull back the curtain like this, but I really want to tell people how important it is to do proper due diligence. I appreciate your kind words.
    Tim Boehm Investor from Tillamook, Oregon
    Replied about 3 years ago
    My hat is off to you Paul! I’m a small fry, only own 7 SFR and like you wish I had bought more during the crash. Sitting on all the cash we have hasn’t done anything, the interest on a million dollars today won’t hardly pay your light bill.
    Paul Moore Investor from Lynchburg, VA
    Replied about 3 years ago
    I hear you, Tim! It is better to have it invested and get the benefit of the lower interest rates rather than being the one subject to them, right?
    Sonia Spangenberg from Manassas, VA
    Replied about 3 years ago
    Thanks for the great share and honesty. My company with a partner is only two years old. We haven’t necessarily lost any thing and ended up holding what was supposed to be a flip to avoid losses. It is cash flowing and has appreciated a bit, and rents are starting to rise. But, I can see where we should have stuck to our original offer price and risked loosing the deal. We have become more aware of the need to walk away rather than worry about acquiring an asset when the numbers indicate. Trusting instinct rather than be pressured against the estimates. We are in the midst of purchasing our 5th property and needed the reminder to stay focused on the analysis and not the excitement of the potential. Thanks for the free lessons.
    Paul Moore Investor from Lynchburg, VA
    Replied about 3 years ago
    Sonia, Yes, that is so true. There is a gut instinct that you can learn to trust. Something that will tell you to walk away. (Sometimes in the voice of my wife!) It has taken me years to learn this, but I am learning. Hopefully you have this down pat now and will not make the mistakes I’ve made.
    Dani Sung Rental Property Investor from San Diego, CA
    Replied about 3 years ago
    Thanks for sharing your wisdom! This is really good information!
    Paul Moore Investor from Lynchburg, VA
    Replied about 3 years ago
    Thanks Dani!
    Scott S. Investor from Minnetonka, Minnesota
    Replied about 3 years ago
    Spot-on. In the past I gave $25k to “experts” to invest for me in the stock market and was “happy” to see $12k of it returned. In contrast, my own real estate investments have done very well. If I can’t find deals of my own then I’ll invest in other people’s REI deals to keep growing.
    Paul Moore Investor from Lynchburg, VA
    Replied about 3 years ago
    Thanks Scott. I have heard that more times than I care to recall. We all learn these lessons over time.
    Jerome Kaidor Investor from Hayward, California
    Replied about 3 years ago
    Let no one tell you that you can’t lose money in RE! I bought a 20 unit building at the top of the market in 2006. We were going to fix it and flip it. Instead, we wound up keeping it for ten years, bleeding $3K to $5K a month, until we had chewed the loan far enough down – and property values had come back up enough – for us to sell it for the amount of the loan. ….It can be hard to attract and keep good tenants when there’s gunfire on the street… Location, location, location. Actually, there was a positive – when I bought that building, I refinanced another complex to get part of the down payment. In 2006, the multifamily loan business was competitive, and I got a VERY good loan. That loan saved me a great deal of money – in fact, it saved me just as much money as I was losing on the turkey. I sold the turkey at a tremendous loss, and the next investor got a good deal. If he manages it well, he will make money. I am accumulating cash, waiting for the next down cycle.
    Adam D. Investor from Castle Rock, Colorado
    Replied over 2 years ago
    If it doesn’t cash flow at minimum $200 on closing day, we don’t buy! Resist the urge to buy just to get a deal done.
    Paul Moore Investor from Lynchburg, VA
    Replied about 3 years ago
    Jerome, That is so true. But I will tell you that I have never lost 100% of my money in a RE deal. I have in many others. Of course it is possible to do that. But I love the way real estate debt is backed by a hard asset.
    Jared Paul from Latham, New York
    Replied about 3 years ago
    Paul, Great post. I am actually in the process of researching and setting up some syndicate deals. Do you have any recommendations from your experience in the syndicate side of things? Do’s and don’ts? Deal structure, etc? Any advice would be greatly appreciated! Thanks again. Jared
    Paul Moore Investor from Lynchburg, VA
    Replied about 3 years ago
    Thank you, Jared. Great talking with you the other day. I wish you the best as you seek out wise counsel on this.
    Hung Nguyen from Greenville, SC
    Replied about 3 years ago
    Great insight. This reminds me that some REI strategies are mostly speculation. Also, it is important to focus on the numbers in any market. However, how do you feel about property management? Is it better to take on the load yourself, or set up pm early and have them take care of things?
    Paul Moore Investor from Lynchburg, VA
    Replied about 3 years ago
    Thank you, Hung. That is true. I always counsel people to get a good Property Manager. I believe the PM and the market account for about 2/3rds of your success in any project. If you plan to grow an REI business, I would never recommend managing even one unit without a property manager. Because the hassles you could have by managing even one unit could cause you so much stress that you may quit. The cost of a PM is significant, but it will pay off if you want to stay in the business and grow a lot. And keep your sanity.
    Elizabeth A
    Replied about 3 years ago
    Thank you for sharing, Paul
    Paul Moore Investor from Lynchburg, VA
    Replied about 3 years ago
    Thanks Elizabeth.
    Krista Riggs Real Estate Investor from Orlando, Florida
    Replied about 3 years ago
    Great post, it seems like speculation is gaining steam again so it’s nice to see articles like this.
    Paul Moore Investor from Lynchburg, VA
    Replied about 3 years ago
    You’re right. And I hope we have all learned from the last downturn. Thanks Krista.
    Ethan LaVigne Investor from Linden, Michigan
    Replied about 3 years ago
    Great stuff Paul! Thanks for the article!
    Paul Moore Investor from Lynchburg, VA
    Replied about 3 years ago
    Thanks a lot, Ethan. Look forward to working together.
    Adam D. Investor from Castle Rock, Colorado
    Replied over 2 years ago
    Paul, you have enough information here to fill at least 3 different posts! I had to reread this whole thing. Please post more often with a little less weight to your articles. It was great and I learned a lot! But, I really had to focus and go over everything again. So, I see you have tons of experience in the real estate and landlording game. I learned a lot from your article, but if you could please, post more times with less info in each post. I look forward to your next post.
    Paul Moore Investor from Lynchburg, VA
    Replied over 2 years ago
    Thanks for reading and commenting, Adam. Good thoughts. I thought they would give me extra credit for long posts… maybe I was wrong. 🙂 Here is a link to all of my posts: