The Power of Time and Tax Advantaged Accounts

Here is a list of things I wish I knew earlier in my career!

Time

Assuming you are 20 and it takes 40 years to hit retirement, your annual investment returns 7% with a mix of stocks, bonds and real estate.

● Every $100 you invest in your 20’s is worth $1497

● Every $100 you invest in your 30’s is worth $761

● Every $100 you invest in your 40’s is worth $387

● Every $100 you invest in your 50’s is worth $197

While we generally earn much less money early in life, the extra time makes these dollars a lot more powerful. Do not underestimate the power of compounding on even small dollar amounts!

Tax

Assuming $100,000 per year.

● Every extra $100 we earn, we only get to keep $70 after federal and NY state taxes

● Every $100 we earn that is tax free, it is actually worth $143

Tax advantaged accounts must be prioritized, it is impossible to beat their true rate of return.

Company Benefits – Pre-Tax Dollars

Allocate as much as you need. You are getting at least a 70% discount on everything!

● Health Care FSA – up to $3200* pre-tax for Medical Expenses (co-pays, sunscreen, braces, ortho-k, etc)

● Dependent Care FSA – up to $5000* (day care, care for elderly, summer camp)

● Transit – up to $315* per month for transit and an extra $315* a month for parking

*as of 2024

Company Benefits – Free Money

● Child care – free child care or tutoring for your children

● Food – snacks, lunches, dinners. Take advantage of these

● Gym memberships – many companies offer gym perks and benefits

● Mobile reimbursement – some companies offer to subsidize all or part of your phone bills

Investments

Backtesting Tool: https://www.portfoliovisualizer.com/

Warren Buffet vs S&P 500

Cathie Wood vs S&P 500

Fact – 90% of the fund managers can not beat S&P 500 over various time periods.

● It is easy to buy TSLA, NVDA, Bitcoin and make quick money

● It is much, much harder to hold these types of investments all the way up to higher dollar values and weather the massive market swings

● Investing in Stock and Bond Index funds on a regular schedule is the most consistent, stress-free way of building net assets

● Don’t try to time the market, it always wins in the end!

Stock vs Bond – How Much Do I Need?

The classic formula is 100 – age. At age 20 you should have 80% stocks, age 30 you should have 70%, age 40 you should have 60% and so on. This is too conservative once you have good savings.

Bond’s only purpose is in the event of unemployment AND stock market crash, it protects you from having to sell stocks at low prices. Depending on whether you have dual income, how much passive income you are generating from real estate and dividends, you should try to keep stock allocation as high as possible. Calculate how much your family really needs per year, subtract passive income, and you can decide for yourself how many years of living expenses you need to keep in bonds. Find something you are comfortable with and stick to it, ignoring the overall account balance.

Make sure your cash is in the money market, short-term treasury bills or CD’s! 2024 interest rates are over 5%!

US vs Rest of the World

There are two schools of thoughts on this:

● S&P 500 companies already get half of their revenue from overseas, so having the S&P 500 alone gives you enough international coverage

● International stocks, historically, performed similar to their domestic counterparts. From 2012 to 2024, thanks to the strong dollar, the gap between America and the rest of the world is ultra wide, this will not last forever and the gap will close. Therefore now is the best time to add international index funds. I personally believe in Option 1.

My Personal Allocation

Track monthly income, expense, cash flow, and asset allocation across all of your accounts. You can use several free websites or you can create your own Excel sheet. I have my own excel sheet because no app will know exactly how to track everything and how I want it tracked.

● I keep 3 months of living expenses in cash, money market and CD’s

401K, IRA, Roth

Max tax-advantaged accounts at all costs. If you need the money, it is only a 10% penalty. A very small price to pay. When you need money from retirement accounts before retirement, you are probably unemployed and in a lower tax bracket which easily makes up for the 10% penalty. You can also borrow $50,000 from your own 401K for home purchase, you pay interest to yourself!

● 401K and IRA are pre-tax contributions, 401K has a $23,000 limit for 2024. At 30% federal/state tax, the government basically lends you $6,900 free money to invest, you get to pocket 70% of the gains, always max this, not just the company match

● Roth IRA backdoor is $7000 per year per person, permanent tax-free gains, it is a must-have

● Consider Roth 401K and Roth IRA conversion when you are in low tax brackets early in your career or during unemployed years

Vanguard Roth IRA Backdoor:

https://investor.vanguard.com/investor-resources-education/iras/ira-roth-conversion

Fidelity Roth IRA Backdoor:

https://www.fidelity.com/learning-center/personal-finance/backdoor-roth-ira

529

Start a 529 as soon as you have a child and choose your own allocation.

529 is basically an extra Roth IRA with no contribution limit. We can give $17,000 per year per child without reporting gifts to the IRS. We can give more with paper work, it will count as part of the lifetime gifts we can give out, currently $5 million lifetime without estate tax.

$5 million sounds like a ridiculous amount of money, but by the time we pass away, with inflation it is totally possible for us to exceed that. Giving money to our children ahead of time in a tax-advantaged account is a great idea.

There are so many ways to cash this out:

● Covers private school even before college ($10,000 a year)

● Covers college, which as it stands today, is $400K for 4 years of private college including room and board

● Covers master, MBA, PHD, medical school and law school

● Can be transferred to other siblings, even grand children

● Can be rolled into Roth IRA ($35K)

None of us will qualify for financial aid, 529 does not affect scholarship. College is a business. If you don’t need financial assistance, the chance of acceptance goes up. 

Target funds are way too conservative. Go for a standard index fund such as the Vanguard S&P 500.

HSA

It is basically a Roth IRA for health care.

It is much more valuable than an FSA because it never expires and can be invested like a Roth IRA.

Personal Property – The Greatest Tax Advantage of Them All!

You don’t need a very expensive place. A one bedroom apartment will last you until you have a child

● Rent, the biggest living expense (until kids), becomes equity investment

● Property taxes and mortgage interest are both tax deductible

Credit Card

Do not underestimate the value of credit cards, as all sign-up bonuses, points, miles, and cash rewards are tax-free.

Pick up sign-up bonuses when you have major expenses coming up (travel, hardware, etc.) is a great strategy. Remember you and your spouse can each get different cards! Amex typically gives the highest sign-up bonuses.

For Day-to-Day Spend:

● Chase Sapphire + Freedom for points conversion to Hyatt, airlines and/or portal redemption (only recommend this for Sapphire Reserve, still recommend point transfer game if you use Chase at all). Chase cards can be rotated for repeated sign-up bonuses. This is ideal if you often travel solo or duo.

● US Bank Reserve card for 4.5% cash back on travel and mobile payment (covers dining, grocery, offline shopping, and much more), and any 2% cashback card for everything else.

● Bank of America Custom Cash Rewards gives you 5.25% and BOA Unlimited Cash Rewards gives you 2.625% if you have more than $100K across all of their accounts, including their Merrill Edge brokerage account. This is ideal if you travel as a family. 

Passing Money Down to Children

Give them enough money so that they can do anything they want, but not too much where they don’t have to do anything in their life. It is my belief that passing down lots of money to your heirs is not wise. Enough for health, education, housing is enough. People need a sense of drive and grit in order to manifest a purpose greater than themselves in their life.

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