How to Unwind a Complicated Investment Portfolio

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Today we'll discuss how to move from a complicated portfolio to a very simple investment portfolio.

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ABOUT ME

While still working as a trial attorney in the securities field, I started writing about personal finance and investing In 2007. In 2013 I started the Doughroller Money Podcast, which has been downloaded millions of times. Today I'm the Deputy Editor of Forbes Advisor, managing a growing team of editors and writers that produce content to help readers make the most of their money.

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DISCLAIMER: I am not a financial adviser. These videos are for educational purposes only. Investing of any kind involves risk. Your investment and other financial decisions are solely your responsibility. It is imperative that you conduct your own research and seek professional advice as necessary. I am merely sharing my opinions.

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I transferred all of my IRA from my advisor to managing it myself. BEST decision ever! It was scary at first but now I enjoy researching what I want to invest in.

karenscookingkorner
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Rob - good stuff as always. You are the best free advisor!!!!

kw
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I converted away from a 1% anum several years ago. They were buying individual stocks rolling there own MF. Luckily this was all in an IRA so I had them sell and send cash. The lesson I learned was give them time to clear all positions, I jumped the gun and moved everything before they were ready. Took about a month before I got it all moved. Even this was relatively painless, hurry up and wait!

oriewall
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Rob I had a the exact situation. I took over from my advisor and the market was down. Inside of two traditional IRAs and two Roth IRA‘s. I moved everything into the three fund portfolio I was working towards. 15:48 15:48 account was very large, but the market was down so I was able to realize a ton of losses and then gains not to exceed those losses so that I would have no taxes. I then moved all that cash into my three fund model. With all that said, I still have a lot left mostly in stocks with some still and some mutual funds I want to get out of. Right now I’m doing a ton of Roth conversions so I’m still managing that issue and cannot Realize any more gains at this time without an insane tax bill. So I’m doing the best I can will see what the future allows. I keep watching for any losses or any situation that might allow me to convert more of what I have in my taxable to the model I want to be.

jackcapone
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Regarding avoiding capital gains in a taxable account: I currently have 30% of my portfolio in AAPL. (I bought 150 shares in 1995, so almost all my current AAPL value is unrealized gains.) I'm working on selling this down, but am spreading the process out over many years. The idea here is to keep under the (2022) $550K limit for taxes on LTCG's. If you stay under that, you pay 15%; if you go over that, you pay 20%.

KeithRollin
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Exactly what I did. I took half from a 2% advisor. Then two years later I took the other half. Cheers

ianwhitehead
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Thank you, Mr. Berger for your continued support.

johnpawlak
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Hi Rob, For dealing with single stock portfolio concentration, there is another option. In kind transfer to exchange funds. Down side is relatively large minimums and fees.

NarenMalayath
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only thing with taking just some out of ira acct from managed to self directed, is then the brokerage won't talk to you because you have a private client (but only on some) but JPM blocks you from working with the brokerage advice only lets you make your own decisions. Then your PC won't talk to you as you have some in self directed

sandyparis
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The point about options is probably about writing ITM covered calls. It wouldnt reduce taxes, but would generate some income with which to pay the taxes. The income from the calls would also be taxed, so not sure this would help much in the long run.

johnnyfive
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I’m 60 and want to retire in 6 months. I have a $170K savings plus a 401k depleted to $200K of money that I’m not sure what I can do with at this point. My retirement plans seem to be out the window. Is it a good idea to get professional help?

PurvisTwiggs
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Vanguard's patent expired May 16th 2023. The problem though is that a lot of fund providers already have both funds and ETFs that are separate. They'd need to combine them to take advantage of Vanguard's patented process.

joelcorley
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What an amazing video. You are exposing them financial industry 😮 and their 60 holding portfolios… Great information. Well done 👍!!

ltmsimply
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Hey Rob I don't why people should be so worried to take a week or two to transfer over they're complicated investment. They should close their eyes for a moment and know that the very thing they're doing outweighs any amount of loss they could have in two weeks. It just creates more worry. the whole idea behind the three fund portfolio is to reduce that worry and live your life to the fullest while your fund is doing all the work ;) zen

dmsoundcollective
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Wow! This spoke right to me! My taxable portfolio is handcuffed in gains with a concentration in tech, 35% of portfolio. I offset this with SCHD, 30% of portfolio. Should I further offset tech exposure and large cap value etf with small cap value etf? Thanks Rob!

Steven-vinb
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What about putting it in FBALX OR WELLINGTON. Having cash in a money market for 2-3 years of expenses. Good years take from fund bad years take from money market.
Replenish when MM is below baseline.

timc
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What if they're in individual stocks? I want to sell them so them go to the three fund portfolio.

michaelkeaton
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We are moving away from our financial advisor who has us in more than a 100 positions in our taxable accounts. I would like to know how to identify which of each positions has a gain or loss and weather it is a less than a year gain (short-term) or long term gain. The assets are in a Schwab account, so it would be helpful to know how to do this on the Schwab platform.

denbarproperties
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I prefer etfs as they are portable across brokers. For my small monthly contribution to taxable, I plan to go with funds at Vanguard that I will convert to etfs once a year. That is because I don't want to worry about spreads and market/limit orders buying etfs for frequent small transactions. Also if there is a day like 1987 when stocks are down rapidly I want the flexibility to sell a part of my investments during retirement

herozero
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For me I inherited a traditional IRA and taxable brokerage accounts with 2 different brokerage firms. Self directed by my brother and I had no choice in the individual stocks I inherited. I sold 4 loser stocks for a small capital loss. Trimmed the top 3 stocks that were 24% of the entire portfolio across all accounts. In taxable accounts I own 44 individual stocks, 8 ETFs (some sector, some covered call ETFs, Franklin Income fund (been around since 1947) 17 ETFs in my Roth IRA some sector, some covered call ETFs.

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