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The Role of Luck in Long-Term Investing, and When To Stop Playing The Game

I am re-reading a series called “Investing for Adults” by William Bernstein. By “Investing for Adults”, Bernstein means that he assumes that you already know the basics of investing and that he can skip to more advanced insights. There are four parts:

A commonly-cited part of the first book The Ages of the Investor is the question “Once you have won the game, why keep playing?”. If you have enough money to buy a set of safe assets like inflation-adjusted annuities, delayed (and thus increased) Social Security payments, and a TIPS ladder to create an income stream for life, you should seriously considering selling your risky assets and do exactly that. (You can keep investing any excess funds in risky assets, if you wish.)

A wrinkle to this plan is that you won’t know exactly when the stock market will help make that happen. Before you reach your “number”, you’ll most likely be buying stocks and hoping they grow in value. Let’s say you saved 20% of your salary and invested it in the S&P 500*. How long would it take you to “win the game”?

Historically, it could be as little at 19 years or as long as 37. That’s nearly a two-decade difference in retirement dates! Same savings rate, different outcomes.

This paradigm rests on too many faulty assumptions to list, but it still illustrates a valid point: You just don’t know when you’re going to achieve your LMP, and when you do, it’s best to act.

If you don’t act, the market might drop and it could take years to get back to your number again. This is one of the reasons why some people should not be holding a lot of stocks as they near retirement. Some people might need the stock exposure because the upside is better than the downside (they don’t have enough money unless stocks do well, or longevity risk), but for others the downside is worse than the upside (they DO have enough money unless stocks do poorly, or unnecessary market risk).

I find the concept of a risk-free liability-matching portfolio much harder to apply to early retirement, as it is nearly impossible to create a truly guaranteed inflation-adjusted lifetime income stream that far into the future. Inflation-adjusted annuities are rare, expensive, and you’re betting that the insurer also lasts for another 50+ years if you’re 40 years old now. Social Security is subject to political risk and may become subject to means-testing. TIPS currently have negative real yields across the entire curve, and only go out to 30 years. (As Bernstein explores in future books, you’ll also have to avoid wars, prolonged deflation, confiscation, and other “deep risk” events.)

* Here are the details behind the chart:

As a small thought experiment, I posited imaginary annual cohorts who began work on January 1 of each calendar year, and who then on each December 31 invested 20% of their annual salary in the real return series of the S&P 500. I then measured how long it took each annual cohort, starting with the one that began work in 1925, to reach a portfolio size of 20 years of salary (which constitutes 25 years of their living expenses, since presumably they were able to live on 80% of their salary). Figure 11 shows how long it took each cohort beginning work from 1925 to 1980 to reach that retirement goal.

Chase Sapphire Preferred and Sapphire Reserve: Helpful New COVID-19 Benefits (Up to 7.5% Back on Groceries)

The Chase Sapphire Preferred card and Chase Sapphire Reserve card have been very popular for their generous travel and dining perks, but right now travel and dining aren’t really happening. Chase has wisely adjusted their rewards program for this new environment, in addition to the recently-added Doordash benefits. I will definitely be taking advantage of these new earning perks, although I’m still leaning slightly towards keeping my points to redeem toward a Hyatt hotel vacation one day…

Chase Sapphire Preferred new changes:

  • 3x points at grocery stores. Earn 3x total points on grocery store purchases from May 1 to June 30, 2020, on up to $1,500 each calendar month. No activation required. Includes Instacart.
  • Redeem Ultimate Rewards points at 1.25 cents per points towards grocery store, dining, and home improvement purchases. (Previously only travel through their portal.) “With the Pay Yourself BackSM tool, your Ultimate Rewards® points are worth 25% more when you redeem them for statement credits against purchases in our current categories: grocery stores, dining (including restaurants, takeout, and eligible delivery services), and home improvement stores such as Home Depot® and Lowes®. Just choose an eligible purchase you made in the past 90 days, apply points for all or part of the purchase, and you’ll get a statement credit. Take advantage of this promotion through September 30, 2020.1”

Since you can earn at 3 points per dollar spent and redeem at 1.25 cents per point at the grocery store, this is effectively makes the Sapphire Preferred a 3.75% cash back card towards groceries (up to $1,500 in purchase each month until 6/30/20). Keep in mind that you can buy many types of gift cards at grocery stores as well, including Amazon.

Chase Sapphire Reserve new changes:

  • 5x points at grocery stores. Earn 5x total points on grocery store purchases from May 1 to June 30, 2020, on up to $1,500 each calendar month. No activation required. Includes Instacart.
  • Redeem Ultimate Rewards points at 1.5 cents per points towards grocery store, dining, and home improvement purchases. (Previously only travel through their portal.) “With the Pay Yourself BackSM tool, your Ultimate Rewards® points are worth 50% more when you redeem them for statement credits against purchases in our current categories: grocery stores, dining (including restaurants, takeout, and eligible delivery services), and home improvement stores such as Home Depot® and Lowes®. Just choose an eligible purchase you made in the past 90 days, apply points for all or part of the purchase, and you’ll get a statement credit. Take advantage of this promotion through September 30, 2020.”
  • $300 annual travel credit counts towards gas station and grocery store purchases. “Now enjoy more flexibility with your annual $300 Travel Credit. From June 1 through December 31, 2020, gas station and grocery store purchases will also count toward earning your Travel Credit. You’ll also earn points on these purchases (and, as always, after your first $300 in travel purchases, you’ll immediately start earning 3x points on travel).”
  • Annual fee renewal $100 discount. Sapphire Reserve annual fee renewals through the end of 2020 will be $450 instead of the normal $550. This is only for renewals, not new cardmembers.

Since you can earn at 5 points per dollar spent and redeem at 1.5 cents per point at the grocery store, this is effectively makes the Sapphire Reserve a 7.5% cash back card towards groceries (up to $1,500 in purchases each month until 6/30/20). Keep in mind that you can buy many types of gift cards at grocery stores as well, including Amazon.

Citibank $200/$400/$700 Checking Account Bonus 2020

Citibank has tiered $200, $400, and $700 bonus offers when you open a new eligible Citi checking account by 6/30/20 and deposit and maintain a certain balance for 60 to 150 days. There is also a $1,500 bonus if you have $200,000 to move over. … [Read the rest]

List of 529 Day (5/29) College Savings Plan Promotions

Promotions updated for 2020. 5/29 is "National 529 College Savings Plan Day" and certain state plans are offering promotions and/or giveaways. Some end on 5/29 and others end on 5/31, so that's why I'm posting this early. Many are simply … [Read the rest]

Creative Business Idea: Selling Baked Goods Online via Etsy

My family enjoys watching Kid's Baking Championship on Food Network, and I'm always impressed how many of these 8-13 year-old contestants have a side baking business! Last weekend, the WSJ article How Etsy Became America’s Unlikeliest Breadbasket … [Read the rest]

Chime Banking App Review: $50 Bonus via Referral

With rates drops everywhere and no end in sight, there are no high APY CDs to open, so I've been picking up various cash bonuses while stuck at home instead. Chime is a popular fintech bank app with a $50 cash bonus after a payroll direct deposit … [Read the rest]

M1 Finance Review: Custom Asset Allocation, Up to $1,500 Transfer Bonus

Updated. As noted in my post on best online brokers, my favorite option in the now-crowded "robo-advisor" category is now M1 Finance. Here's a quick rundown of what makes them different: Fully customizable. You pick your own target asset … [Read the rest]

Vanguard Digital Advisor Services (VDAS) Review: Only Slightly More Expensive Than Target Date Fund

Updated. Vanguard has increased the marketing and added some details about their new portfolio management service, Vanguard Digital Advisor Services (VDAS). Here is the new full PDF brochure. After reading through the entire brochure (again!), … [Read the rest]

Suze Orman’s Updated Financial Advice 2020

The NYT has a new Suze Orman comeback piece called Suze Orman Is Back to Help You Ride Out the Storm. I'm old enough to feel nostalgia over the peak Suze Orman years, and it was interesting to read how some of her advice as changed: Some of Ms. … [Read the rest]

Tastyworks Brokerage Bonus: 100 Free Shares, Worth $100 to $600

Free stock shares are the trendy bonus nowadays - WeBull, SoFi, Robinhood, Public, and more - but how about 100 free shares? Tastyworks wants your attention by offering 100 free shares of a randomly-picked stock valued between $1 and $6 per share. … [Read the rest]

Webull App: $0 Stock Trades, $0 Options Trading, 2 Free Shares Bonus

Updated offer details. Webull is a brokerage app (PC and web version also available) that has unlimited free stock trades with no platform fees, free real-time quotes, and no minimum balance requirement. As of March 2020, it has now added $0 … [Read the rest]

SoFi Money $75 Bank Bonus + $75 Stock Bonus Via Referral

Updated offer details. SoFi ("Social Finance") has expanded from students loans into a cash management and stock brokerage account. They've also updated their bonuses for trying them out, and if you have a spouse/partner, you can refer each other … [Read the rest]