First ever review

[jboss]

Hi Guys, first time member/poster. I've been looking for a resource like this for a long time. I am the type of person who refuses to pay financial planners, stock brokers, etc,. as my personality is one where I feel like I can learn to do everything as good as others (for better or worst). As a result, I've virtually had zero guidance ever since I started investing around age 20 (in 2008 I felt there was no way to lose). It wasn't much, but it helped us buy our first house. I was very conservative initially when I didn't have much money, but ever since passing ~500k I've been taking some huge risks (more on this later). I read a lot on the Internet and watch market news, but thats about it for expertise. My theory for a while (6-7 years ago) was that investing in established companies who pay dividends was a pretty solid strategy, but I convinced myself I needed to take more risk.

Since about 23 I started my own contracting business in IT security (mostly contracting). Over the course, my wife and I have saved about 1 million in our various retirements accounts and taxable brokerage. I took quite a bit of heat early (first 2-3 years of biz) when working the 14 hour days and neglecting our early marriage but I told her it would pay off and that I'd rather work hard when we have no children and be able to ease off the gas to enjoy life when we do. She agreed, but it was not easy, this was never possible without her support. I also wanted to capitalize on a young person's ability to really burn the oil (sleep ~5 hours/night over and over again), I knew it wasn't sustainable.

I recently turned 30, we both work and have no children + mortgage, but kids are coming up very soon (next year). We have been maxing out any possible retirement plan for a while now, her roth 401k, my SEP IRA, 529 college savings plans (pay for kids college someday), HSA (been maxing that for close to 7 years and never touched it). All of my extra savings goes straight into my taxable brokerage account while I keep some on-hand cash (~70k) in a money market account for emergencies. I'm self employed and need some cash buffer. We have some real old IRA's before we passed the income restriction, not much in there. We are in the 40% tax bracket now + I pay the self employment tax, so I do literally anything to sock money away and avoid taxes at this stage in our life.

If I counted up our homeowner equity, cars, assets we are probably closer to 1.5 million net worth but I'd rather not count anything that isn't liquid. With the exception of my wive's firm-sponsored 401k, all of our savings is in stocks and I mean everything. I'm a big risk taker, after having some success with early consulting biz I did a startup which is bordering on failure now (currently in talks to potentially sell but its unlikely). I lost about 40k and thousand hours in time (when you are a consulting time is $$). I also lost about 50k in the stock market in last 2-3 years from a bad bet on an IT company and the melt down of oil stocks (which I originally thought were safe 10 years ago). Like I've said, I've become addicted to taking larger risks now that I have more money. As a result, I own nearly 100k in Amazon stock. I made a lot of money early on through that but now it looks insane to even say. I just bought equifax stock yesterday. Some of it is my personality, but I also think I have become numb to losing money if my bets don't pay off.

All of my current holdings are picked stocks, mostly large companies, 50% of which pay dividends, the rest are essentially tech stocks (microsoft, apple, tesla, amazon). I believe tech is the future for all industries so I don't necessarily view this as not diversified. I am also heavy on pharma and robotics. I also felt that true diversification was too low risk. I don't trust myself to pick stocks much anymore except large entities that have a low likelihood of failing. I don't really know how much I've made on my holdings over the years because I hardly sell when anything is up, I have an impulse to hold on to everything forever. But it's fair to say that through a failed startup and some bad stock pics I've probably lost 100k in the last 4-5 years. Granted, I've probably made over 100k in returns as well but I have not realized/sold (thank you NextEra/Amazon).

My question is, am I being too wreckless? I'm starting to feel like I've taken "enough" risks at this point in my life and should start coasting to preserve. If I lose a ton of money I will be severely depressed and lately I have become afraid of losing what I worked so hard for. I recently debated municipal bonds and selling a lot of my stocks in favor of index ETFs so that I can simply stop worrying. I'm at the point now that I am personally managing so much money that I feel like I should get some help, but I also don't trust brokers who make money off of my money. We have also had some lifestyle creep, range rover-style creep which has scared me quite a bit. I've realized it and trying to prohibit. Although, part of me likes to keep throwing the bone out further and if that means I need to buy something to keep motivating myself then I'll do it. Regardless, I know its not a smart choice. I somewhat refuse to pay financial planners because I think I know more than them (stubborn).

Is it safe to say I should scale back after having taken so many risks already? startups, big stock pick bets failed, etc. OR should I keep the pedal to the metal? I was a big believe in no pain no gain, must take risks to "get ahead" and avoid regrets BUT at some point when is enough enough?

I don't want to retire anytime soon, I mostly work from home and contract. I could do this forever since it is basically my own schedule. I love what I do and it's not work. I figure that about 1 million invested @ age 30 is almost enough to throw the towel in already and easily retire around 50 max, but that is not my style.

Thoughts:

1. Should I move some retirement out of stocks and into ETFs or something safer? Is 100% stocks sane for our net worth?

2. Any investment vehicles I am missing here? We are in the top tax bracket + about another 15% self employment, its insane. I pay more than 130k in taxes.

3. Should I try to avoid dividend stocks in my taxable brokerage account? I was moving dividends to nontaxable because of how high our tax rate was, it was pissing me off to pay income tax and unqualified dividends and lose our on full compounding due to paying cap gains. Are holding all dividend stocks in retirement still a sound strategy or is that an old fools game from 20-30 years ago?

4. Am I crazy to hold so much tech? I like risks and this is one bet I am confident in but I don't want to destroy our life. If Amazon goes bankrupt and shuts down tomorrow I'll be in a ball in a corner.

5. Is some lifestyle creep good for motivation? Or should it all be killed with fire? We moved out of our old house and bought something about double the price which is much nicer, drive nice cars, etc. Part of me thinks you need to walk the walk to run with certain crowds, e.g., biz partner comes over for dinner your house should be nice to rationalize your pay, but another part is depressed about the waste. Should I be reaping rewards from our success or push that off to 50? What if we die early? I started to become afraid of working ALL the time these days and telling my wife "we will enjoy life later" because you just don't know what can happen before "later" comes. I feel like we should enjoy some sucess but also feel stupid spending money our us when we don't even have children yet nor do we know what complication may lay ahead. I'm a huge car guy and I have a very expensive toy but it makes me feel guilty to own at this age.

6. If you were me, would you go into conservation mode provided the risks already taken? We plan to have ~3 children and my wife will stop working soon. I don't think I can afford to take many more big risks nor will I feel comfortable post-children.

Thanks all! Apologies for the length and rambling.

[athena53]

It sounds like you're off to a really solid start. At your age, being overloaded in equities isn't necessarily bad but you need to learn to deal with downturns in the market without panicking or else put more into boring stuff like bonds. In the last meltdown I lost over $500K- on paper. I was working at the time, so adding new money and buying at bargain-basement prices. If you have quality holdings, they recover. (If you don't- well, as Warren Buffet is fond of saying, "When the tide goes out you see who's been swimming naked".)

I'm one of the heretics here who has an advisor. Yes, I know what I'm paying him and I'm happy with the returns on my portfolio. He knows more about the market than I do, which is saying a lot since I've been investing since I was 19. I find his "macro" perspective of the market useful. They're not all evil, especially if you've got the experience and the smarts to sort out the annuity salesmen and the penny stock dealers. I decided I wanted one when the pile got big enough that I didn't want to make any major mistakes, especially since the time frame to retirement was getting shorter. (I'm 64, retired at 61.) Having said that- if I were to start over I might just go to a mix of ETFs and periodically readjust the allocation.

Spending- I was never much for spending to keep up appearances. I spent on what I enjoyed. I did have a work wardrobe of tailored suits and separates, made to measure, in the USA. I still wear them when I need to look respectable. I drive a mediocre car- always have, not a big priority. My late husband and I lived modestly in many ways but travel was our passion. Every dime we spent on travel was worth it and since his death last year I've visited Iceland, Greenland, Costa Rica and Panama. We downsized two years ago- a nice house, but smaller, and it's great to have lower carrying costs. More for plane tickets! So, yes, enjoy some of the fruits of your labor along the way.

[jboss]

Quote:

Originally Posted by athena53 It sounds like you're off to a really solid start. At your age, being overloaded in equities isn't necessarily bad but you need to learn to deal with downturns in the market without panicking or else put more into boring stuff like bonds. In the last meltdown I lost over $500K- on paper. I was working at the time, so adding new money and buying at bargain-basement prices. If you have quality holdings, they recover. (If you don't- well, as Warren Buffet is fond of saying, "When the tide goes out you see who's been swimming naked".) I'm one of the heretics here who has an advisor. Yes, I know what I'm paying him and I'm happy with the returns on my portfolio. He knows more about the market than I do, which is saying a lot since I've been investing since I was 19. I find his "macro" perspective of the market useful. They're not all evil, especially if you've got the experience and the smarts to sort out the annuity salesmen and the penny stock dealers. I decided I wanted one when the pile got big enough that I didn't want to make any major mistakes, especially since the time frame to retirement was getting shorter. (I'm 64, retired at 61.) Having said that- if I were to start over I might just go to a mix of ETFs and periodically readjust the allocation.

Thank you for your response.

I can certainty understand the piece of mind using an advisor after you reach a certain sum. I became the same way with tax folks, I couldn't trust myself anymore. I may look into at least finding someone who can review my portfolio periodically. I just want to stay away from active management by someone else.

That is an excellent Buffet quote, I agree. The problem is that a lot of the risky stocks are generally driven up by speculation and not something that survives downturns (imo) because there are no fundamentals :/. When I look at the ETF returns / index returns its amazing that it seems to beat most of my stocks, especially once you add in the losses. This is what has really changed my mind about holding so many stocks. I was on-board with Mark Cuban's "diversification is for idiots" early on, I can see how you need to take big risks and when you don't have money you cant diversify much to do that. BUT after a certain point, how much do I want to lose from my hard work. I don't even have the time to research my current holdings and really think much about it, this is why I never sell at a gain. I feel to do that you need a lot of insight into the company. If I can't get to that point because of work schedule, should I move to ETFs?

To be honest, when I think of retiring I don't think of not doing anything and just relaxing. Mostly because I enjoy what I do. I would rather be "retired" and working "when I want". I would like to pull back my hours to maybe 20/week around 40 but make enough to pay expenses with little savings. I probably wouldn't be pulling from savings until at least 50 assuming I can have 2+ million by then and a 5% dividend can do the trick.

[38Chevy454]

See answers below in red text

Quote:

Originally Posted by jboss 1. Should I move some retirement out of stocks and into ETFs or something safer? Is 100% stocks sane for our net worth? I think you need more diversification, so a broad index-type fund is good way to do this. Can certainly be more than one fund. If you want to stay in tech or oil or whatever, you can investigate sector funds. At least sector funds have more diversification than single company. As you state, the problem with single company is you can hit home run or strike out, diversification is kind of like a steadying and moderation effect. 2. Any investment vehicles I am missing here? We are in the top tax bracket + about another 15% self employment, its insane. I pay more than 100k in taxes. With your high tax bracket, anything you can do to make that less is good. Only thing I can think of with your self-employed business is consider having more business deductions. 3. Should I try to avoid dividend stocks in my taxable brokerage account? I was moving dividends to nontaxable because of how high our tax rate was, it was pissing me off to pay income tax and short term dividends. Dividends should be taxed at lower rate than your income, I think? But you can move to non-dividend paying, and then you just have to deal with long term capital gains when you sell, which LTCG are taxed at 15% 4. Am I crazy to hold so much tech? I like risks and this is one bet I am confident in but I don't want to destroy our life. If Amazon goes bankrupt and shuts down tomorrow I'll be in a ball in a corner. See answer #1, more diversification is suggested 5. Is some lifestyle creep good for motivation? Or should it all be killed with fire? We moved out of our old house and bought something about double the price which is much nicer, drive nice cars, etc. Part of me thinks you need to walk the walk to run with certain crowds, e.g., biz partner comes over for dinner your house should be nice to rationalize your pay, but another part is depressed about the waste. Should I be reaping rewards from our success or push that off to 50? What if we die early? I started to become afraid of working ALL the time these days and telling my wife "we will enjoy life later" because you just don't know what can happen before "later" comes. I feel like we should enjoy some sucess but also feel stupid spending money our us when we don't even have children yet nor do we know what complication may lay ahead. I'm a huge car guy and I have a very expensive toy but it makes me feel guilty to own at this age. Life is about trades, any more savings you can do now means less to spend, but also less years to work until you retire. You state that you like your work, so maybe having a reduced work schedule is way to enjoy the successes so far? As I am sure you know, your budget is controlled by you. I understand the image with customers concern. I have always had several cars, so I am not a good one to say don't have the big toys. 6. If you were me, would you go into conservation mode provided the risks already taken? We plan to have ~3 children and my wife will stop working soon. I don't think I can afford to take many more big risks nor will I feel comfortable post-children. Never hurts to be more conservative, although it sounds like your wife's work is pure extra and you will be fine on your salary alone, even with additional kid expenses. I think the general diversification of your equities is what is needed. I have always been high on equities, being 100% all the way up to about 50 years age and only changing a few years ago, although I still target higher than most on here at around 70-80% equities. Thanks all! Apologies for the length and rambling.

[jboss]

Quote:

Originally Posted by 38Chevy454 See answers below in red text

With a name like Chevy454, I can see you have the itch. Congrats on the retirement!

I agree, equity diversification is likely needed. In regards to the dividend stocks, I was referring to unqualified dividends that are taxed at income level. I recently started moving dividends to nontaxable accounts to allow further compounding instead of paying tax on them (even qualified tax) today.

This is correct, income from my wife is just extra right now. But once she is no longer earning it will put more stress on me and my start/stop consulting biz, but I feel that if I had a conservative nest egg that would potentially help relieve.

Any thoughts on never selling well performing stocks? I have a bad habit of never cashing in when I should, I just assume that if I hold everything for 10+ years it will work out better. Seems the only things I sell are poor performers. Is playing around like that wise for retirement or set/forget ideal and focus on macro?

In regards to the increasing biz expenses, I am trying my best. I have a "company" car that I lease. I don't know how much more I can do before things start to look a bit questionable to the IRS. But that is definitely a fair suggestion. If anyone knows of more self-employed biz expense tricks I'm all open. I do the home office, write off just about any electronic device I buy, cell phone, car, insurance, etc. I recently got a tax lady, before that I thought my college accounting degree would do the trick but I was really just an audit risk.

[DrRoy]

You are more aggressive than I would be comfortable with. I have never been 100% stocks. Even when at your age I think I was max 85% or so. I also have totally passed on individual stocks. As you said, they are not performing for you as well as some index ETF's. I am now all indexed for equities - mostly SPY or equivalents, and some VTI. On advisors, I had one for several years after I passed $1M, but my own return performance was better than his (before fees) so I fired him.

[athena53]

Quote:

Originally Posted by jboss Any thoughts on never selling well performing stocks? I have a bad habit of never cashing in when I should, I just assume that if I hold everything for 10+ years it will work out better. Seems the only things I sell are poor performers. Is playing around like that wise for retirement or set/forget ideal and focus on macro?

I've got large chunks of Berkshire and Apple with huge unrealized gains. Nothing wrong with hanging onto good stocks although Jim Cramer would advocate taking some money off the table after a big runup. My question is whether you'd find anything better to buy if you did.

One concern I have is that you say you don't have time to do a lot of work researching investments. There are some good shortcuts- I like to use the Analyst consensus on the Fidelity site, which shows the recommendation of individual analysts and then weights them according to their analysts' track records. I don't buy unless the consensus is good; I get concerned and do more research when the opinions worsen. You do need to be aware of what's happening even with your best-performers in case there are reasons to get out. How many individual stocks do you own? You may be better off cutting back the number and going to ETFs. There are tax consequences, of course and maybe you just transition into this is you sell other holdings. Caveat: I am neither a tax expert nor a financial advisor.

[NgineER]

Congratulations on your success!

You can remain 100% equities if you want to, I don't see a big issue with that at your age. What you need however, is a plan. It would probably benefit you to sit down with your wife to talk to a fee only advisor to set up such a plan. A good advisor would ask questions about your wants for the future, family and time horizon, life insurance, college plans for kids etc. It would make you pause and reflect about what is important.
Prior to having kids myself, I saw myself as immortal pretty much. Seeing an infant child makes you realize how vulnerable we are and how little we know about most things.

The benefit of not being a 100% equities is that when the stock market falls, you'll be buying more equities (on sale) and when the market is increasing, you'll put your monthly contributions into fixed income.

You need to have a plan that works in all situations, it might be boring, but it will help you with important decisions.

[jboss]

Quote:

Originally Posted by NgineER Congratulations on your success! You can remain 100% equities if you want to, I don't see a big issue with that at your age. What you need however, is a plan. It would probably benefit you to sit down with your wife to talk to a fee only advisor to set up such a plan. A good advisor would ask questions about your wants for the future, family and time horizon, life insurance, college plans for kids etc. It would make you pause and reflect about what is important. Prior to having kids myself, I saw myself as immortal pretty much. Seeing an infant child makes you realize how vulnerable we are and how little we know about most things. The benefit of not being a 100% equities is that when the stock market falls, you'll be buying more equities (on sale) and when the market is increasing, you'll put your monthly contributions into fixed income. You need to have a plan that works in all situations, it might be boring, but it will help you with important decisions.

Thank you for this information. I like the strategy for market up/down using fixed income. Since my bracket is high I was looking at municipal bonds. I got into the market for the first time in 2008 and realized the benefits of having cash during a downturn. I often debate keeping cash on the sidelines for a downturn in the market but in the last year its hard to tell when that will even come. At which point, I've sidelined cash for a year with minor returns. I constantly debate that.

Regardless, I agree, I need a plan. The last few years I've just been socking the money and assuming "it will work for me" with little guidance. I've started to rethink that after taking a few baths on poor stock picks and getting cocky. I can already feel my life perspective changing once a child comes, to the point where it may scare me into grabbing an industry job with a dependable wage. I assume by "fee only" planner this is essentially a consultation. I will look around. Good advice, thanks.

[pb4uski]

Quote:

Originally Posted by jboss ....1. Should I move some retirement out of stocks and into ETFs or something safer? Is 100% stocks sane for our net worth? 2. Any investment vehicles I am missing here? We are in the top tax bracket + about another 15% self employment, its insane. I pay more than 130k in taxes. 3. Should I try to avoid dividend stocks in my taxable brokerage account? I was moving dividends to nontaxable because of how high our tax rate was, it was pissing me off to pay income tax and unqualified dividends and lose our on full compounding due to paying cap gains. Are holding all dividend stocks in retirement still a sound strategy or is that an old fools game from 20-30 years ago? 4. Am I crazy to hold so much tech? I like risks and this is one bet I am confident in but I don't want to destroy our life. If Amazon goes bankrupt and shuts down tomorrow I'll be in a ball in a corner. 5. Is some lifestyle creep good for motivation? Or should it all be killed with fire? We moved out of our old house and bought something about double the price which is much nicer, drive nice cars, etc. Part of me thinks you need to walk the walk to run with certain crowds, e.g., biz partner comes over for dinner your house should be nice to rationalize your pay, but another part is depressed about the waste. Should I be reaping rewards from our success or push that off to 50? What if we die early? I started to become afraid of working ALL the time these days and telling my wife "we will enjoy life later" because you just don't know what can happen before "later" comes. I feel like we should enjoy some sucess but also feel stupid spending money our us when we don't even have children yet nor do we know what complication may lay ahead. I'm a huge car guy and I have a very expensive toy but it makes me feel guilty to own at this age. 6. If you were me, would you go into conservation mode provided the risks already taken? We plan to have ~3 children and my wife will stop working soon. I don't think I can afford to take many more big risks nor will I feel comfortable post-children. Thanks all! Apologies for the length and rambling.

1. Don't confuse ETFs with not being stocks... there are many equity based ETFs out there that give you exposure to stocks since the underlying investments are stocks. I don't see stocks being a problem for you... but rather the lack of diversification and making big bets. You could consider migrating your equities to 80% total stock and 20% tech sector if you want a tech tilt.

100% stocks is not unusual for someone your age and working since you have good cash flow to live on. You may want to start putting a little new money in muni-bonds or a muni-bond fund.

2. Muni bonds are a good choice for someone in your high tax bracket.

3. I think dividends and capital gains are your friend. Even in your high tax bracket the tax rate on qualified dividends and LTCG is "only" 20%. If/when you retire and no longer have earned income then the tax rate on qualified dividends and LTCG is much lower.... in some cases (like mine) even 0%.

4. Put on a little tech tilt if it makes you happy... but I would do it with ETFs or funds rather than individual stocks.

5. It is hard to find a life-style balance.... I always had nice cars... but not as nice as what my BILs and other peers drove... but I've been retired for 6 years and they are still working. Similarly, we lived in a nice house but definitely lesser than what we could have afforded on our income.

6. I've been content with earning what the markets give and not trying to hit home runs on individual stocks or making big sector tilts.

YMMV.

[CoolRich59]

Quote:

Originally Posted by jboss Since about 23 I started my own contracting business in IT security (mostly contracting).

Just in case you're interested, I *think* Equifax may be hiring.