Let me share with you how to make a lot of money in the stock market and STILL feel bad. The stock market really has a way of humbling us all at some point.
On May 5, 2013 I wrote an article called, “Should I Invest In China? A Top Down And Bottoms Up Perspective.” My simple thesis was that with the Yen depreciating to 100+ due to Abenomics coupled with strong world markets, China must inevitably catch up in a risk-on environment.
I then identified the Chinese internet space as the most laggard sector where investors should consider putting money to work. Chinese internet stocks have been going straight down for two years. Stock picks included BIDU, SINA, and RENN.
So what happened with the stock picks since then? And more importantly, did I put my money where my mouth is or was I just pontificating like some useless Wall St. research analyst does with Neutral/Hold/Wait And See ratings? I hope you know by now that I don't like wasting time writing about things I don't know or care to act upon. Of course I invested in my thesis. I just didn't invest enough.
The Stocks Shot Higher
Almost like magic, every single name ramped higher by 15-25% within three weeks after publication while the broader markets climbed 2%. It was almost as if someone got a hold of my article and forwarded it around, causing a buying frenzy. If there's a chance this is true, is there any wonder why hedge funds keep their holdings as close to their chests as possible?
Since publishing my post on China, my IRA grew by roughly $40,000. Sounds OK right? Not really since I started off with $400,000 at the end of April. I will usually take a 10% gain for the full year any day. However, a 10% gain is a 5-15% underperformance of my stock picks, equating to roughly $20,000 to $60,000 in money left on the table.
So what the hell happened to cause such a leakage in performance you ask? Ill-timed accumulation and exiting of positions as well as FEAR. Remember, I am the King of bad trades.
The below chart shows the value of my IRA portfolio today. The pending activity is pending cash as a result of $209,913 worth of stock sales as I'm continuously worried about a market correction. I already sold $168,006 worth of stock several days earlier.
At the same time, I'm not willing to place massive short bets either because the market is being artificially propped up by the Fed.
MY IRA PORTFOLIO BEFORE THE BAD TRADES
You might be thinking I'm being greedy for being disappointed with a $40,000 gain within a month. And you're right. I have made similar amounts of money trading in the past so $40,000 is not that unusual, even in this short time period. It's all relative at the end of the day.
What really gets to me is leaving so much money on the table. With $20,000 – $60,000 I could go around the world on a luxury cruise for three months. I could get 13 year old Moose some fresh new tires and spark plugs.
If I wanted to cheat on Moose, I could get a nice new 2013 Nissan Sentra for $20,000 or wait to get the 2014 BMW 335i couple coming out this fall for $60,000. I could even treat myself to some fresh ramen noodles instead of always buying the $2 instant stuff I've been eating as punishment for being unemployed.
Here's another kick in the nuts. My portfolio was over $450,000 just a couple weeks ago! The high was actually closer to $455,000 but I failed to take a snapshot that one fine day. The fact that the markets have moved up over the past two weeks while I proceeded to lose ~$15,000 from the top is maddening.
As you can tell from my positions, I take very concentrated positions with Apple at one point accounting for $178,366 or 40% of my entire portfolio.
SO WHAT THE HELL HAPPENED?
So what on earth made me bleed $15,000 of profits in a couple weeks? I want to share with you in as visceral a writing style as possible an inside look on how a neurotic trader's mind works.
Apple scared me stupid. Apple has had quite a rebound after hitting a low of $385 before announcing their 2Q results. I went relatively huge in Apple in the low 400s by buying around $160,000 worth of stock. When the stock was at $457 as you can see in the chart above, I was thinking, “Who were the idiots selling at $400 or below? I'm riding this thing to at least $500 baby! New product cycle in 2H2013 and 2014 for sure!”
Then one day news reports came out saying that Julian Robertson and David Tepper, two hedge fund giants exited or lightened up significantly in 1Q2013 causing the stock to plummet to $420 from $460 in just three days.
I was then thinking to myself, “What kind of idiot starts selling after these hedge fund giants sell after the stock has collapsed by 40%? Are people really that stupid to sell based on after the fact information? Getting these two giants out is actually a positive because that means there's less stock for them to sell!“
Related: A Stock Split Doesn't Change Fundamentals, But Could Boost Share Price
Wanted To Buy More Stock But Couldn't
I wanted to buy more stock at $420, but was I really supposed to build a $200,000+ position in Apple out of a portfolio size of only $400,000? Besides, I already have an Apple structured note that is either going to lose me $10,000 on June 17 or make me $1,400. It felt irresponsible to accumulate more, and I was also too scared to pull the trigger. One thing I thought about during the Apple crash to $420 was that I can't fight stupid. It's like playing poker. It's very hard to bluff an idiot because they don't think in multi-level scenarios.
When Apple rebounded to around $435, I began to sell a total of around $115,000 worth of stock like a coward. I was in the process of discovering my risk tolerance, something no investor really knows until they put real money on the table.
Not being able to completely relax when I was in Hawaii for two weeks was annoying. 40% of my portfolio in one stock was too gut-wrenching. I've come to realize that 20% of my portfolio in one stock is probably the maximum level where I'll be able to relax. Suboptimal trading led to $3,000 less profits.
Then Baidu Missed Estimates
Baidu actually rallied around 9% into their latest quarter results in April and I was feeling like a champ. When they missed, the stock plummeted from $92 all the way down to $83 again, wiping out all my gains. I shouldn't have been so greedy with a 9% move in one week, yet I was fearful the company would blowout earnings and surge after results.
I cursed myself for not selling while I had a chance and promised that if the stock ever rebound back to $92 or higher that I would take my 15% and run like Forest. “What the hell is wrong with Baidu's cost structure?” was my biggest concern.
Not only did the stock rebound to $92, but the stock hit $100! I began to think, “Who the hell was selling at $83 just the other week? Those fools! Thank goodness I didn't capitulate.” I ended up selling my entire position at an average price of $95, leaving roughly $5,000 on the table.
What's more concerning is that I won't be able to get back in because I think Baidu could go to $115 this year. Here's another case of selling too soon due to volatility. I should have at least kept a token $25,000 position and see what happens.
As soon as I bought half my desired position in RenRen at $2.75, the stock began surging to $3.20 for a 13% gain on 6X average volume in a matter of two days. It was as if the penny stock traders of the world got a hold of my article and all piled in.
As a result, I bought the other half of my position, about 11,000 shares at a less than ideal price of $2.90. The company then reported uninspiring results and guided on the low end for the upcoming quarter. The stock fell down to around $3 and steadily kept going lower back down to $2.8, wiping out about $5,000 worth of gains. I was pissed.
What was annoying was that I had about a $30,000 order sitting on the bid at $2.85 for three hours and didn't get filled. “God damn market makers manipulating the markets again! How the hell can I not get filled when RENN is trading on multiple times average volume? What a bunch of crooks.“
When the stock inexplicably ramped higher on 5/20 to $3.10, I got the hell out at an average price of $3.08 because I have no time for difficult executions. Of course the stock continued to rally higher to around $3.12 after I sold, but it eventually came back down to below my selling price. Renren's costs are out of control and lacks focus.
The CEO actually sounded scared on the conference call when talking about Tencent, its largest competitor. Renren was my punt stock, and I walked away with a gain. If the stock gets back down to $2.80 or less, I will be back in. Not selling at $3.20 cost me around $2,500 in profits lost.
SINA Has Done Great
I actually bought the majority of my Sina position before Alibaba announced its acquisition of a minority stake in Weibo, the Chinese Twitter. Sorry, I can't tell you all my trades beforehand. Alibaba's purchase values Sina at roughly $60 a share on my own calculations. As a result, I sold 70% of my Sina stake at $61 a share and will just let my remaining 300 shares ride, or will I?
My biggest regret with Sina was not going bigger. I only had a $58,000 position (13% of my portfolio) in the name as I bet on the wrong horse, Apple. If I was smart, I would have built a $160,000 position instead which could have turned into more than a $40,000 gain. My greatest fear is that I won't be able to rebuild a chunky position as the market discovers the name and the Twitter IPO hype resumes. The mistake of not going bigger realistically cost me over $20,000 in lost profits.
Shorting The Market
Due to my fear of a pullback, I decided to short ~23% of my portfolio by buying $48,000 worth of SDS. SDS is a double short ETF, so the short value at risk is closer to $96,000 instead ($96,000/$440,000). The idea is to short a frothy market and outperform with individual stock picks.
The markets have continously moved higher in May to my surprise and I ended up losing around $2,500 in this hedge trade which I quickly covered. If I didn't sell my SDS when I did, I would have lost another $2,000, so I guess that's somewhat of a win in my book.
The reality is, I should have gone double long instead of short. “The market wants to go crazy and I'm being an absolute idiot by going against the Fed! I guess it really is true that everybody is making lots of money and employed again except for my stupid self! To the moon baby!” I facetiously thought.
SDS will continue to be my imperfect hedge of choice and I'm considering putting on a new trade with the shares at $38.XX. Right now I'm assuming that everything I've sold will continue to go up and never let me back in at a lower price.
I hate the feeling of missing out, but I've also got to balance the horrible feeling of round-tripping a stock or losing money. With gas at $4.50, the 10-year yield at 2.03% and the summer doldrums here, what could go wrong with stocks shooting to the moon? Only time will tell!
You Might Lose Your Mind Investing
As you can see from my writing, consistently making market winning trades is difficult. You can make a lot of money in the stock market and still feel bad.
Instead of the $40,000 in profits I made in May so far, I'm thinking about the realistic $20,000 – $60,000 more in profits I could have made! Greed is bad! Investing is a very emotional process that quickly finds out what you're really made of. This is why I get annoyed at folks who say that investing is so easy. They make me feel worse by being so scared and stupid.
Further, the difficult of making big money in the stock market is why I prefer real estate. Not only is real estate a tangible asset that is less volatile and provides income, real estate is also tax advantageous. Don't underestimate real estate's tax-free profits of $250,000 / $500,000 for singles and married couples.
What's even more frustrating about so much lost profit is that I wasn't thorough enough in my research on Chinese internet stocks. I never believe one should fail due to a lack of effort, and I failed BIG TIME in May for not being diligent enough.
More Stock Misses
Dang Dang (DANG), the “Amazon of China” is up a whopping 80% in May alone. If I had a stronger work ethic, or if I was simply just a little bit smarter I would have discovered Dang Dang and invested probably $50,000 into the name.
My investment would have then gone up by $40,000 for potentially a $100,000 additional gain in May to $540,000 instead of just $440,000. Suddenly, $40,000 in one month is like pocket change. My goal is to build my IRA into a significant enough amount of money where I can enact Rule 72(t) to withdraw money penalty free before I'm 45.
There is always a bull market somewhere. Remember this line. It's up to all of us to put in the EFFORT to find hidden gems. If I decided to sleep in until 8am one Saturday morning instead of write my Chinese investment article, I never would have invested in anything. At most I would have made maybe $8,000 (2%) in my IRA if I dumped everything into an S&P 500 ETF like SPY. But I don't think I would have because of my short-term bearish view on the overall market as evidenced by my ill-timed SDS purchase.
Slow And Steady Investing
The temptation to buy growth stocks for capital appreciation is great, especially when there is maximum FOMO as we are experiencing today. If you're still early in your financial journey (<40 years old), you should invest in growth stocks.
As you get wealthier and older, you can invest more in dividend stocks. I'd much rather make money the slow, boring, easy way and just buy and hold forever. Making 20%+ through my long term structured products investments since June 2012 is much more enjoyable because I haven't had to think.
Yes it's taken 12 months to make slightly more than I made in the past three weeks, but it's worth waiting. Having a downside buffer and knowing that I'm locked in for two to four years never felt so good.
Not having to experience fear or greed is the reason why real estate is my favorite asset class. There's no choice but to hold on due baffling monopolistic commission rates!
Dangers Of Buy And Hold
The only problem with buy and hold is that I've seen too many violent corrections in the markets: the Asian crisis in 1997, the Ruble crisis in 1998, the dotcom implosion in 2000, the housing market correction in 2006, and financial Armageddon in 2008-2009. Then of course there is the ongoing global pandemic.
All these corrections make me uncomfortable in setting and forgetting large sums of money in the market and hoping for the best. Companies have life cycles and corrections always happen.
Here is my 2022 stock market forecast and 2022 housing market forecast in case you're interested. I'm much more bullish on housing than I am on stocks.
Important Disclaimer: Please do your own research when investing in stocks and don't follow my advice because my portfolio positions are changing on an almost daily basis. I've used my trades to help show you how you can make suboptimal trades as an investor due to emotions. My IRA portfolio is my trading portfolio where I take aggressive positions which are NOT recommended for folks who depend on their portfolio for retirement purposes. I've got other long term index fund focused portfolios that are earmarked for retirement and multiple passive income streams to survive.
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About the Author:
Sam began investing his own money ever since he opened an online brokerage account online in 1995. Sam loved investing so much that he decided to make a career out of investing by spending the next 13 years after college working at Goldman Sachs and Credit Suisse Group. During this time, Sam received his MBA from UC Berkeley with a focus on finance and real estate.
In 2012, Sam was able to retire at the age of 34 largely due to his investments that now generate roughly $250,000 a year in passive income. He's very focused on investing his money in real estate crowdfunding to arbitrage the lower valuations in the heartland of America. He spends time playing tennis, hanging out with family, consulting for leading fintech companies, and writing online to help others achieve financial freedom.
Updated for 2022 and beyond. All the Chinese stocks went up massively and then got crushed again.
42 thoughts on “How To Make A Lot Of Money In The Stock Market And Still Feel Bad”
Hey Sam, Trust me when I say it’s way better to sell early for a gain then to get greedy and hold on for more, only to get slaughtered. You’ll never go broke making money on trades. You will go broke(and insane) continually chasing that last penny. Be happy with your 40k trade, that’s more then most people make in a year.
Oh I trust you alright! Round tripping is the worst! Fighting greed is hard though, especially when this is my Punt Portfolio. I don’t know why I’m still fearful and greedy.
All of this analysis makes my head hurt, FS! It reminds me of the bad old days when some of my friends day-traded. They were always nervous wrecks, even when they DID make money.
If/when I seriously get into stocks, I’ll probably just go for the Vanguard 500. That is, once I figure out why there are 2 funds, an ETF and a “regular” one. Any idea what that means and which one is “better” or more appropriate?
Indeed. Tis why day traders and professional poker players don’t last long if they don’t have a huge bank roll! Zero sum game.
Thanks for the update. I am bad with optimal trading too. Its tough to accept loss, but am glad that you managed profits.
I’d be interested in an investment forum as well.
So have you read my post on stops and how I love to use trailing stops ? :) Seriously though, you can’t beat yourself on bad moves. We have all had them and will have them again. The worse thing you can do with a bad move is to let it interfear (intentional misspelling) with your future investment activities!
Nice to see you’re human Sam. We’re all emotional, especially when it comes to money. I had a punt portfolio. Let’s just say it got punted! I know leaving money on the table isn’t fun, but at least you managed profits. My frustration with my some of my moves is if I had done nothing, kept it in the bank, or followed the S&P I would have been better off than eating losses. An investing forum would be fun and educational. Sounds like a great idea!
Google to $1,000! The Bay Area economy needs more wealth influx!
Funny thing is that I’ve had 5 Google employees submit applications for my rental this week. The money really does flow over to the rest of us.
Thanks for the update! I got a few shares of apple when it hit $400, but sold too early at $430… I’m terrible at optimal trading too. I’m finding out that I’d rather just buy and hold. It’s much easier than sitting on cash or trying to time trade. It’s stressful and I don’t need it.
I’ll stick with it through the rest of this year and see how it goes.
I probably will go back to buy and hold for the long run. I’m really afraid of big corrections too. It’s tough when you don’t have income to buy more shares during the pull back.
I’m seriously waiting for a mega correction like Japan just experienced before I dive all in again. Maybe it will never come, but I’ve got 70% of my IRA in cash now waiting to pounce if it does.
I want to say (like they used to say in those old Westerns…) “WOAHH, NELLIE!!”
You are trying to time the market. Therefore you are buying yourself all the frustrations and anxieties that doing that kind of activity implies. You will lose money, guaranteed. Sometimes you will make money, guaranteed. Maybe sometimes your investments will hit it out of the park (would be nice, huh). But in no circumstances will you always make money, it is not possible with this style of investing.
So, if you like what you are doing and are willing to live with the variegated results, then fine, have a good time. If you like what you are doing but cannot tolerate the variegated results, then you have a problem that is either an indication you need to change your behavior, or you like theater.
Perhaps you are too impatient to buy for the long haul, for example by focusing on dividend investing. But it certainly an alternative to the nail biting and panic emotions of trying to time the market.
There are plenty of people who do the dividend route, it just does not get as much play in the popular press. For me, it removes the stress. I buy only high quality companies that have paid dividends for decades and have a strong track record. In fact, I dont mind when the stock price goes down, because it means I get more for my reinvested dividends.
This style of dividend investing might be considered old fuddy-duddy by the marketeers of Wall Street, but I sleep well at night.
I’m definitely impatient. Even with my IRA accounting for less than 10% of my net worth I get very amped when I trade because I’m so focused!
Sounds like you have the same issue that I do (I do some currency trading on occasion). It definitely takes a lot of guts and smarts about a person to be able to make the most of the situation. Just keep examining and perhaps diversify into something like bonds if you get too nervous.
I had a limit order to buy more Apple today at $435 as well but it didn’t get hit. I will build a large position again if Apple starts cratering again.
Ahh, missing out on double the gains is annoying as heck.
Lightening up positions is a good idea.
You’re right, investing is an emotional game! That’s why in the last 6 years, I’ve only invested in mutual funds, rather than individual stocks. As we all know, none of us are Warren Buffett. I’ll do the numbers on my mutual funds and post them on my blog one day soon. Right now all I can report is that I’ve been doing “pretty well”.
I look forward to reading your portfolio update. Shoot me a reminder when it’s published.
It can be so easy to get emotional when it comes to investing. Even with my written out plan on my desktop I still make stupid mistakes from time to time. My last one was on some AAPL options several months ago. I made a killing on them, and I am happy for that, but I got out too early and could’ve earned another couple thousand. You live and learn though and the key, I find, is to try and learn from those. That said, I am happy overall for the month & the year. I am up 3.5% on the month and just over 20% on the year. I totally think you should start an investing forum, I’d be interested at least.
Cool. I’ll count you as one of the first forum members! Together, we will blow this joint!
Definitely! The more the merrier.
I remember some investing advice I heard on the radio that seems to make sense. Never invest more than 5% of your portfolio in any one stock (company). Following 3 (foreign) stocks may be a bit too much too. Although I have some (5) individual stocks, I prefer mutual funds because they may the decisions for me.
Are you saying a 40% position in Apple was a bad idea?
It could be if you bought at $700! :) The 5% rule is intended to diversify your concentration in one stock.
True. As a trader, it would be too hard to manage 20 positions at a time. It would also be very expensive given the trading costs. The most number of stocks I would invest in at a time would be around 10.
I don’t think your trades on the Chinese stocks constitute “bad” trades. If you (or anyone else) knew the exact right time to buy and sell stocks, you’d be writing on FS from your own private island!
Investing is like poker in that you’re making decisions based on incomplete information. These trades equate to a situation where you see you could have gotten more value on your final bet after you’ve seen your opponents losing hand. It doesn’t make your play bad, it’s just a product of not being able to be 100% certain at the time you have to make the decision.
Indeed. One thing to find a great idea, another thing to bet big with conviction. I constantly fail at holding onto conviction due to fear.
At least with poker, if I know I’m an 80% favorite I’m always pushing all I can knowing 20% of the time I will lose.
I’ve had to limit the amount of time and money I invest in stocks because it was too distracting for me and I got too stressed out. It’s a great feeling taking gains though! The thing with stock investing is to remember nobody gets it right 100% of the time. Not even the highest paid hedge fund manager can time every peak and trough at the max. Nice job putting yourself out there and taking the risks so you have the opportunity to get the rewards!
Yes, stock investing IS very distracting and addicting as well. Now that I have so much free time I can’t help but research ideas. I don’t think it’s healthy to be so involved over the long run so I’m going to keep my activities to under 2 hours a day for sure of investing. Maybe 1 hour is enough.
I guess I am a pretty conservative guy. I would not put that much of my entire portfolio in one stock. Not that Apple is Enron, but when will a company by Enron show up again, or GM or all the other single stocks that crashed. High risk, high reward. Congrats on your gains, best wishes for more.
Thanks, but my gain feels like a loss. If you’re a young guy (in your 20s), I would encourage you to take more risk, as there’s much less to lose. It’s one of my regrets now that I’m in my mid-30s. We have a lifetime to make money. Let’s just hope it doesn’t take working a lifetime….
What would you recommend now that I am in my mid 30’s with a family? I am moving some of my money in to peer-to-peer lending. The rest is primarily in retirement accounts.
How much of your net worth is in real estate? It’s seriously my favorite asset class for the long term until probably 50, when I definitely don’t want to manage property anymore and will just hire someone to manage for me.
The Real Estate Investor’s Mindset is worth a read.
Seconded – real estate is the way to go.
The question as I read the post is that you can’t look at a month in the rear view mirror or you’ll go nuts! Like if you are playing poker and you have 2 and 7 off suit. Just because the board says 2, 2, 7 doesn’t mean you should have stayed in.
As of today and at this time (5-23 and 11am) SINA is at $57 – how does that change your calcs?
Given I believe the Alibaba deal values SINA at $60 for now, I’m a buyer! Do you have a Punt Portfolio? How have you done this May?
My portfolio has changed a lot again. Bought back into BIDU, accumulated SINA, increased my Apple position by 65% this morning, and bought IEF as the 10-year bond yield over 2% is too attractive to resist. IEF is my summer hedge vs. straight up shorting the market. Any good trades you’re thinking about to share?
Anytime I get cute I get whooped by the market (last one was betting against LULU) so I am really just focusing on my boring boring dividend portfolio…but even that has most of my buys near 52 week highs.
What is a punt portfolio?
A portfolio where you take big risks outside your normal risk parameters. Speculative portfolio in other words.
Any good trades you’re thinking about?
Well Sam, look at it this way you are learning more and more every time you trade. Hell I would be grateful making 40k in a month but you have done it before so your expectations are set higher. Greed and fear move the market, i say this all the time. Even if the financials look good it doesn’t mean the stock wont tumble. its why its always good to take some profits off the top. Some of your ill-time trades are better then my best trades. LOL
Selling at a loss or selling at a profit is extremely difficult. It’s why it’s probably best to get out of positions in 2 or 3 tranches at a time. My problem is, once I sell more than half my position I get completely disinterested in the stock b/c I can no longer make the same type of money. It’s a weird psyche.
With the markets melting off… maybe my selling of Chinese internet stocks earlier in the week wasn’t so bad after all. Time to get back in!
Aren’t 2x ETF’s inherently going to lose money over any period of time compared to the asset because of how math works?
Eg you have 100 dollars of some underlying asset and which you’ve got a 2x etf and it loses 10%.
Looks right. But then say the next day it gains 11% so your 2x gains 22%
Do this enough times and it becomes a real difference.
All I know is that I should have KEPT my 5,300 shares of SDS yesterday as the markets began cratering! DAMNIT! Another ill-time trade :)