Jesse Cramer » Contributors: Expert Voices On Baby Boomer Life & Legacy

15 Questions for Scared Investors Right Now

Before the article, here’s what’s happening this week on our podcast, Personal Finance for Long-Term Investors:Editor’s Note: I published this article on April 9, about 45 minut…

Before the article, …

Before the article, here’s what’s happening this week on our podcast, Personal Finance for Long-Term Investors:Editor’s Note: I published this article on April 9, about 45 minutes before President Trump announced a 90-day pause on tariffs, sending the market **rocketing** skyward. I’ll be surprised if this is the last of the tariff tantrum, and I stand by every question below. Happy reading!I want to float these punchy, Socratic questions out there and let them sit. I want you to pause and think.I don’t want to tell you any of my answers or any “be…

Jesse Cramer April 9, 2025

Let Them Trade Stocks

Historians doubt Marie Antoinette ever said, “Let them eat cake.” The apocryphal tale is that upon hearing that French peasants had no bread, she coldly suggested they eat brioche instead – a…

Historians doubt Mar…

Historians doubt Marie Antoinette ever said, “Let them eat cake.” The apocryphal tale is that upon hearing that French peasants had no bread, she coldly suggested they eat brioche instead – a richer, more expensive pastry. Shame on you, Marie!But historians doubt she ever said it. The quote likely originated decades earlier and was used to criticize out-of-touch aristocrats. Still, the myth stuck, fueling the image of a clueless queen and symbolizing elite indifference during the French Revolution.Fast forward to modern times: I’ve been reading account after account of …

Jesse Cramer April 8, 2025

The 15 Tariff Questions I’ve Heard Most

My blog inbox and my professional inbox exploded last week with tariff questions.At first, I thought, “Everyone’s already talking about it…do I really need to add my voice to the fray?”…

My blog inbox and my…

My blog inbox and my professional inbox exploded last week with tariff questions.At first, I thought, “Everyone’s already talking about it…do I really need to add my voice to the fray?”But the questions kept coming. And after two terrible red days on Thursday April 3 and Friday April 4, the futures market looks glum heading into Monday April 7. So, like it or not, here are my two cents.I wrote this Q&A. My goal is to make it rapid-fire and easy to consume. If you’re sick of tariff talk, skip it. If you know everything already, skip it. But if you want a simple-yet-th…

Jesse Cramer April 6, 2025

Pedal to the Metal?

Comedian George Carlin joked,“Have you ever noticed that anybody driving slower than you is an idiot, and anyone going faster than you is a maniac?”What’s your driving style?Th…

Comedian George Carl…

Comedian George Carlin joked,“Have you ever noticed that anybody driving slower than you is an idiot, and anyone going faster than you is a maniac?”What’s your driving style?The Bullet floors it in the left lane, weaving through traffic like Richard Petty, convinced speed limits are merely suggestions.The Oblivious Cruiser plants themselves in the middle lane at precisely 47 mph, blissfully unaware of the mile-long parade of frustrated drivers behind them.The Wildcard alternates between tailgating, sudden braking, and last-second exits, as if being chased by an …

Jesse Cramer April 2, 2025

The “Asset Location” Dilemma: Tax Strategy or Tax Trap?

Before the article, here’s what’s happening this week on our podcast, Personal Finance for Long-Term Investors:The world of financial planning comprises many strategies and tactic…

Before the article, …

Before the article, here’s what’s happening this week on our podcast, Personal Finance for Long-Term Investors:The world of financial planning comprises many strategies and tactics, some big and some small. Dollar-cost averaging, sequence of returns, tax-loss harvesting, and the list goes on.Depending on who you ask, the process known as “asset location” could be one of the more impactful arrows in your financial planning quiver…or it could be a total waste of time.So which is it? Does asset location matter in the long run? And if so, can we quantify it?…

Jesse Cramer March 25, 2025

35 Lessons from 35 Years

Before the article, here’s what’s happening this week on our podcast, Personal Finance for Long-Term Investors:I originally wrote this in 2021 (31 lessons in 31 years). But here i…

Before the article, …

Before the article, here’s what’s happening this week on our podcast, Personal Finance for Long-Term Investors:I originally wrote this in 2021 (31 lessons in 31 years). But here in 2025, I’ve had a crazy busy week and not enough time to write a brand-new article. Perfect timing though! My birthday is Saturday, so let’s just update this post for 35 years!Last year, I wrote about the amazing Growth that can occur in a single decade. Here’s that article: A Lot Can Change in Ten Years.But for this 35st birthday, I went back and considered 35 valuable lessons tha…

Jesse Cramer March 18, 2025

Should I “Reset” Retirement Withdrawals in Bad Markets?

Before the article, here’s what’s happening this week on our podcast, Personal Finance for Long-Term Investors:Jesse – I’m confused about how “the 4% rule” and other “s…

Before the article, …

Before the article, here’s what’s happening this week on our podcast, Personal Finance for Long-Term Investors:Jesse – I’m confused about how “the 4% rule” and other “safe withdrawal rates” can change so rapidly in such a short period of time. If someone had retired in the middle of 2022 (a bear market), their “safe” withdrawal amount might be artificially low. Whereas if they had retired a mere ~6 months earlier, their safe withdrawal amount would be much higher. And this SWR is supposed to apply for life! How can a 6-month difference in retirem…

Jesse Cramer March 11, 2025

Are You Not Entertained?!

Before the article, here’s what’s happening this week on our podcast, Personal Finance for Long-Term Investors:Do you know that scene in Gladiator where Russell Crowe’s characte…

Before the article, …

Before the article, here’s what’s happening this week on our podcast, Personal Finance for Long-Term Investors:Do you know that scene in Gladiator where Russell Crowe’s character, Maximus, yells to the crowd, “Are you not entertained?!” Yeah, this scene.I’m more interested in Maximus’s next line: “Is this not why you are here?!”You see, the audience came to see violence and death. Specifically, the plan was for a bunch of local gladiators (heavily armored, fully armed) to kill some foreign slaves (including Maximus). But because Maximus is the…

Jesse Cramer March 6, 2025

Is ‘Benefits Hacking’ Genius? Or Immoral?

Most readers of The Best Interest do not come here to learn about Ice-T. But here we are.Perhaps you know him best as “Fin” – a mean-mugging detective on Law and Order: SVU.He’s not …

Most readers of The …

Most readers of The Best Interest do not come here to learn about Ice-T. But here we are.Perhaps you know him best as “Fin” – a mean-mugging detective on Law and Order: SVU.He’s not happy…Or, maybe you remember his West Coast hip-hop days from the 80s and 90s.The fair question to ask right now is, “Jesse…nothing against Ice-T, but where’s the transition to personal finance? Is Ice-T a new client or something?”We’re getting there.I just learned that Ice-T is credited with creating the phrase “don’t hate the player, hate the game,” which he…

Jesse Cramer February 25, 2025

The Man Who Never Looked Up

Before the article, here’s what’s happening this week on our podcast, Personal Finance for Long-Term Investors:I’m reading Morgan Housel’s recent book, Same as Ever, right no…

Before the article, …

Before the article, here’s what’s happening this week on our podcast, Personal Finance for Long-Term Investors:I’m reading Morgan Housel’s recent book, Same as Ever, right now. One of the chapters is called “Best Story Wins.” [While I’m not sure it’s word-for-word the same, this chapter can be read (for free) via Morgan’s blog: https://collabfund.com/blog/story/]Housel’s idea is fascinating – and probably makes sense to us all. The takeaway is that humans promote or discount particular ideas simply because of the story told around that id…

Jesse Cramer February 19, 2025

Buffett’s Way vs. Index Funds

Before the article, here’s what’s happening this week on our podcast, Personal Finance for Long-Term Investors:Reader Phil wrote in last weeKJesse – I appreciate everything …

Before the article, …

Before the article, here’s what’s happening this week on our podcast, Personal Finance for Long-Term Investors:Reader Phil wrote in last weeKJesse – I appreciate everything you have to say on stock Investing and low-cost, diversified index funds. I also love all the Warren Buffett Wisdom you share. But, at least when it comes to investing, isn’t Buffett a counter-example to diversified indexing? How do you square that circle? PhilThis question is like a young dad placing a baseball nicely on a tee so that little Timmy (that’s me) can step up with his $29 W…

Jesse Cramer February 13, 2025

Baby Maeve and the Ovarian Lottery

Before the article, here’s what’s happening this week on The Best Interest Podcast:My daughter, Maeve, is about to turn 8 months old. She’s chunky, smiley, and effortlessly sits…

Before the article, …

Before the article, here’s what’s happening this week on The Best Interest Podcast:My daughter, Maeve, is about to turn 8 months old. She’s chunky, smiley, and effortlessly sits like Buddha while playing with her toys. No crawling or walking yet. She did recently learn to wave (…flail her arm) to say hi to people. It’s pretty cute.And I’m sorry…we’re trying hard not to plaster pictures of Maeve all over the Internet, so you’ll have to take my word on it.But parenting isn’t a cake walk. Kelly and I have put a lot of time and resources into pro…

Jesse Cramer February 6, 2025

The Eye of the Beholder

Before the article, here’s what’s happening this week on The Best Interest Podcast:Do you know someone who cheers for a particular sports team simply “because?” They usually h…

Before the article, …

Before the article, here’s what’s happening this week on The Best Interest Podcast:Do you know someone who cheers for a particular sports team simply “because?” They usually have a mundane reason, like “I just liked their logo when I was a kid…so I started cheering for them” or “my dog was named Viking, so I cheered for the Vikings.” Fast forward 30 years and they are still diehard fans despite having no other connections to the team.I know one fellow Rochestarian – I’ll call him Patrick for the sake of anonymity – and he’s “that fan” for …

Jesse Cramer January 28, 2025

Tricky Dick’s Essential Retirement Advice

Richard Nixon remains one of the more fascinating and complex figures in American history, embodying well-known deep flaws in parallel with acts of brilliance. His most infamous role was as t…

Richard Nixon remain…

Richard Nixon remains one of the more fascinating and complex figures in American history, embodying well-known deep flaws in parallel with acts of brilliance. His most infamous role was as the puppet master behind the Watergate scandal, ultimately leading to his resignation from the Presidency and scarring his Legacy. Some historians point to Watergate as the watershed (ha!) moment beginning the decades-long slippery slide (ha! ha!) of anti-government paranoia leading to today. However, Nixon’s career also exhibited sharp intellect, strategic political thinking, and an ability…

Jesse Cramer January 22, 2025

Do Not Zoom in On Monthly Returns

I’ve had a few clients reach out to me over the past couple weeks (the last week of December 2024 & first week of 2025) with similar concerns:“How and why did my account go down at the end o…

I’ve had a few cli…

I’ve had a few clients reach out to me over the past couple weeks (the last week of December 2024 & first week of 2025) with similar concerns:“How and why did my account go down at the end of 2024?!”The short answer: accounts are down because the market is down, and the market is down due to inflation and interest rate fears that were stoked by the December 17/18th Federal Reserve meeting.But that’s not what I want to focus on today.Instead, I want to focus on the true genesis of the question: these clients noticed a 1% to 2% drop in December, and that was cause fo…

Jesse Cramer January 8, 2025

The Oldest Bad Joke on Wall Street

Have you heard this year’s version of Wall Street’s favorite joke?“We’re going to predict how the stock market does this year!“Woof. Yikes. Why?!1-year stock predictions are…

Have you heard this …

Have you heard this year’s version of Wall Street’s favorite joke?“We’re going to predict how the stock market does this year!“Woof. Yikes. Why?!1-year stock predictions are pointless. We’d all be better off accepting that fact.Risk, Reward, Timelines, and MoreTime and again, I want to ensure every long-term investor understands the relationship between risk and reward.A guarantee – a.k.a. zero risk – comes with the least reward. That “zero risk asset” is a short-duration US treasury note or a high-yield bank account.As we seek out more re…

Jesse Cramer January 3, 2025

Confession: I Leased a Car (?!)

Most personal finance experts would tell you that cars are a terrible investment. Cars are a “necessary evil,” a steep price to get from Point A to Point B. You’re leaking Money on a depreciatin…

Most personal financ…

Most personal finance experts would tell you that cars are a terrible investment. Cars are a “necessary evil,” a steep price to get from Point A to Point B. You’re leaking money on a depreciating asset.They’d tell you to avoid debt a car as best you can. Owning a depreciating asset is one thing, but it’s far worse to borrow money against that asset.And they’d tell you that leasing a car might be even worse because you won’t even own it at the end of the day! You’ve got all the negatives of purchasing or borrowing, but without the benefit of, you know, owning the car. …

Jesse Cramer December 31, 2024

It’s Not Rocket Science

Friend-of-the-blog Christian has done something remarkable. He’s lost ~85 pounds over the past 7 months, dropping from ~280 pounds to ~195. Kudos, Christian!Inspired by Christian’s success, my…

Friend-of-the-blog C…

Friend-of-the-blog Christian has done something remarkable. He’s lost ~85 pounds over the past 7 months, dropping from ~280 pounds to ~195. Kudos, Christian!Inspired by Christian’s success, my own health has sharpened into focus. I have the data to support this – I’ve gained 8 pounds over that same period that Christian’s lost 85. I’ve gone from “slightly overweight” to “assuredly overweight.”I’m heavier than I’d like. Slowly but surely, I’ve been moving in the wrong direction. I used to be in much better shape, and Christian asked me at the gym this morning, …

Jesse Cramer December 18, 2024

The Worst Cost I’ve Seen from Bad Financial Advice

I met with a family a few weeks ago for an introductory conversation. I’m always interested to learn about people’s history with money. It’s an open-ended question that allows for a multitude of…

I met with a family …

I met with a family a few weeks ago for an introductory conversation. I’m always interested to learn about people’s history with money. It’s an open-ended question that allows for a multitude of interesting answers.This family explained that ~20 years ago, they received a significant lump sum payment. They reached out to a financial professional (a stock broker, e.g. Merrill Lynch or Morgan Stanley) in their town and entrusted him with their new-found money.That advisor recommended a single “hot stock.” You probably know where this is going.Within a couple months of…

Jesse Cramer December 12, 2024

Taylor Swift or Cristiano Ronaldo? And Their Hidden Investing Lesson

Here’s a fun question from friend-of-the-blog CJ:“I was hanging out with family and friends around Thanksgiving, and I wanted to gauge their opinion on something interesting:Who is more f…

Here’s a fun quest…

Here’s a fun question from friend-of-the-blog CJ:“I was hanging out with family and friends around Thanksgiving, and I wanted to gauge their opinion on something interesting:Who is more famous globally: Taylor Swift or Cristiano Ronaldo?Almost everyone I asked [for reference, readers: CJ is about 30-years old and lives near me in Western NY] quickly said, “Taylor Swift.”…but I’m not so sure. Because when I pressed them Why?, the answer usually came down to, “Because she’s more famous to me.”Hmmm. Very interesting!What do you think, reader? Who is m…

Jesse Cramer November 29, 2024

5 Year-End Financial Planning Tips

The end of the year flies by. One day, you’re eating turkey and pecan pie and taking a well-deserved nap. Next thing you know (or so it seems), you’re counting down the New Year’s clock to welco…

The end of the year …

The end of the year flies by. One day, you’re eating turkey and pecan pie and taking a well-deserved nap. Next thing you know (or so it seems), you’re counting down the New Year’s clock to welcome 2025.If you’re not careful, the holiday season will fly by (in a sleigh?) before you can do these 5 intelligent things in your financial plan.Conduct a Year-End Financial ReviewEvery year, I run a year-end financial review. A year-end financial review looks back and summarizes seven important areas:Spending (including Unexpected Expenses)IncomeSavingNet Wort…

Jesse Cramer November 21, 2024

What Long-Term Stock Returns Should I Assume in My Plan?

“If all you have is a hammer, everything looks like a nail.”We’ve all heard that phrase, alongside the concept of having “the right tool for the job.”I submit that many people in the…

“If all you have i…

“If all you have is a hammer, everything looks like a nail.”We’ve all heard that phrase, alongside the concept of having “the right tool for the job.”I submit that many people in the Retirement Planning community (especially online in DIYer circles) do not have the right tools or mental models for including long-term stock market returns in their financial plans.Example 1:I saw this question on Reddit this week:Howdy! Currently 26, I can FIRE at 45 if I get 8% returns. What percent returns for the stock market do you guys use planning for 20+ years out? The …

Jesse Cramer November 9, 2024

You Received a Windfall: Now What?

There are a few broad categories that trigger people to reach out to me.Retirement planning is biggest. Major life changes (marriage, divorce, having kids) is a common reason, too.Another one…

There are a few broa…

There are a few broad categories that trigger people to reach out to me.Retirement planning is biggest. Major life changes (marriage, divorce, having kids) is a common reason, too.Another one, albeit slightly more unique: “I have a good handle on our finances, but I want to get you involved because my spouse needs someone trustworthy. If I get hit by a bus, I want you already involved to fully take the reins.”But somewhere in the Top 5 most common reasons is the rationale for today’s article:“I received a BIG sum of money…and I have no idea what to do next!”…

Jesse Cramer October 30, 2024

Is the “4% Rule” Too Risky?

Much ink has been spilled on the 4% rule, including here on The Best Interest.The short and sweet definition? The 4% rule is a retirement strategy that suggests withdrawing 4% of your portfolio�…

Much ink has been sp…

Much ink has been spilled on the 4% rule, including here on The Best Interest.The short and sweet definition? The 4% rule is a retirement strategy that suggests withdrawing 4% of your portfolio’s value annually, adjusted for inflation, to ensure your savings last for a 30-year retirement.If you’d like to dive deeper on some nuance of the rule, read this: Updated Trinity Study and the 4% Rule.And if you’d like to avoid the common mistakes of using the 4% rule, read this: You’re Probably Using the 4% Rule All WrongToday, though, I want to show you some compelling data…

Jesse Cramer October 24, 2024

“An Unmarked Bag of Puzzle Pieces”

‘Twas the night before Christmas, etc. etc., and you’re jazzed. Christmas is great! Morning comes, you let the dog out to pee and fix yourself some coffee. Fresh cinnamon buns! Soon it’ll be tim…

‘Twas the night be…

‘Twas the night before Christmas, etc. etc., and you’re jazzed. Christmas is great! Morning comes, you let the dog out to pee and fix yourself some coffee. Fresh cinnamon buns! Soon it’ll be time to open presents.You bend down low by the Christmas tree, and there, behind the nicely wrapped boxes and doo-dads, you see…a plain bag full of puzzle pieces? …With YOUR name on it?!I think you’d immediately face three burning questions: The first and most obvious: What the hell?! Whose sick idea is this?Second, once you’ve accepted this strange reality: Are you s…

Jesse Cramer October 15, 2024

The Simple Secrets of Modest Millionaires

I started a great dialogue with “Carl” in August and immediately felt a kindred Lifestyle connection. Carl and his wife, “Colleen,” are about my age, with young children, and they earn a healt…

I started a great di…

I started a great dialogue with “Carl” in August and immediately felt a kindred lifestyle connection. Carl and his wife, “Colleen,” are about my age, with young children, and they earn a healthy-but-not-astronomical income ($160,000 pre-tax, which puts their family in the ~75th percentile). Carl reached out to share some exciting news: Their family surpassed $1M in net worth at age 35. They are millionaires. I prodded Carl and Colleen for the tips, tricks, hacks, and pitfalls on his path to millionaire status. Yes, he’s been reading and listening to The Best Interest for a …

Jesse Cramer October 9, 2024

Putting a Dollar Sign On Financial Planning

Whether you’re a dedicated DIYer or prefer to lean on professional guidance, the truth is clear: smart financial planning can save you a lot of money over time.Below, I’ll share some recent e…

Whether you’re a d…

Whether you’re a dedicated DIYer or prefer to lean on professional guidance, the truth is clear: smart financial planning can save you a lot of money over time.Below, I’ll share some recent examples of tactical planning moves I participated in, including how much money was saved.COVID PanicIn March 2020, you could be forgiven for thinking: “the world is ending, and I want to sell everything.”But with proper perspective and an investment policy statement – both hallmarks of sound financial planning – many investors stayed the course.They rode the stock mark…

Jesse Cramer September 22, 2024

Debt Interest: The Silent Killer

After a recent podcast episode, a listener asked me to expound on debt’s “silent assassination technique.” Debt is not a cobra that unexpectedly strikes from the undergrowth. It’s a python you…

After a recent podca…

After a recent podcast episode, a listener asked me to expound on debt’s “silent assassination technique.” Debt is not a cobra that unexpectedly strikes from the undergrowth. It’s a python you stupidly take out of the cage and allow to slither around your torso until you suddenly realize it’s squeezing harder than you can handle.In this post, you’ll find some simple math to show you how stifling debt interest can be.Of course, we need a disclaimer. Not all loans are the same. Some loans are perfectly acceptable to hold on your balance sheet. Namely, loans with low intere…

Jesse Cramer September 16, 2024

Don’t Panic: Some Questions Are More Important Than Others

It can be fun to ponder the details of your specific portfolio allocation. Should it be 70% stocks? 75%? Maybe even 80%?! We had a terrific question from reader “Vince” about just this idea:…

It can be fun to pon…

It can be fun to ponder the details of your specific portfolio allocation. Should it be 70% stocks? 75%? Maybe even 80%?! We had a terrific question from reader “Vince” about just this idea:Winning the Game: Retiring at 57 with $4.2MThose conversations move the needle and are essential to an overall financial plan.But there are far more critical portfolio questions to ask yourself. FAR more important. Namely questions like…How would you have acted on September 12, 2001?How about during March and April of 2020?What about during the depths of 2007 & 2008?…

Jesse Cramer September 13, 2024

Some Bets I’m Willing to Make

The bachelor party decided to go to the casino. I happily went along for the ride. The behavioral finance nerd in me was ready to witness fascinating behavior. Gambling can certainly be entertaining, …

The bachelor party d…

The bachelor party decided to go to the casino. I happily went along for the ride. The behavioral finance nerd in me was ready to witness fascinating behavior. Gambling can certainly be entertaining, but it’s not financially savvy. As long as you know that, you’ll be ok – albeit a little lighter in the wallet.This particular casino had an engaging “loss leader.”* They offered $15 in free casino credit to new gamblers. The scheme, of course, is cynical. They hope those free bets hook you, knowing that a regular gambler will surely lose back more than the free $15 over a long peri…

Jesse Cramer September 4, 2024

Foggy As It Ever Was

In August 1979, Warren Buffett wrote an article for Forbes attacking the herd instinct of investors. The late 1970s were tough for the American Economy, and the stock market reacted harshly.B…

In August 1979, Warr…

In August 1979, Warren Buffett wrote an article for Forbes attacking the herd instinct of investors. The late 1970s were tough for the American economy, and the stock market reacted harshly.Buffett wrote,“…the future is never clear; you pay a very high price in the stock market for a cheery consensus. Uncertainty actually, is the friend of the buyer of long-term values.” Warren BuffettThe future is never clear. Let Buffett’s wisdom sink in. Uncertainty surrounds us, like fog on the highway. Risk is omnipresent. Say it with me: risk is omnipresent. Only our perce…

Jesse Cramer August 28, 2024

How Well Do You Know Your “Frame?”

Friend-of-the-blog Anthony is a personal friend who read my very first articles when I shared them on Facebook. He’s seen The Best Interest grow over time. A couple of years ago, I told him tha…

Friend-of-the-blog A…

Friend-of-the-blog Anthony is a personal friend who read my very first articles when I shared them on Facebook. He’s seen The Best Interest grow over time. A couple of years ago, I told him that The Best Interest wasn’t what I wanted it to be. I felt directionless at the time, and was considering hanging up my writing gloves for good. And, in fact, I did hang up my podcasting microphone for a couple years.He responded, “You know Jess…you can’t see the picture if you’re standing inside the frame. I’m outside the frame. So trust me when I say: You’ve got something sp…

Jesse Cramer August 22, 2024

How to Ensure Financial Misery

One of Charlie Munger’s famous speeches is “How to Live a Life of Misery.” Rather than tell graduates how to live happily, he delivered the opposite message. Because if you avoid life’s surefi…

One of Charlie Munge…

One of Charlie Munger’s famous speeches is “How to Live a Life of Misery.” Rather than tell graduates how to live happily, he delivered the opposite message. Because if you avoid life’s surefire miseries, what’s left but happiness? Right!?Munger was famous for quoting famous mathematician Carl Gustav Jacobi (as in, “Jacobians” in vector calculus) who said,“Invert. Always invert.” JacobiSome math problems, quite simply, are easier to solve if you turn them inside-out.Today we’ll do the same, but for personal finance and investing. What follows are my be…

Jesse Cramer August 14, 2024

Be Cool, Honey Bunny

I’m drafting this on August 5, 2024. The S&P 500 is down about 8.5% over the past three weeks. Headlines are screaming at us. CNBC is throwing a fit. Our bowling partner just posted an apocalyptic w…

I’m drafting this …

I’m drafting this on August 5, 2024. The S&P 500 is down about 8.5% over the past three weeks. Headlines are screaming at us. CNBC is throwing a fit. Our bowling partner just posted an apocalyptic warning on Facebook – stick to bowling, Frank!But the seasoned long-term investors remain cool as a cucumber. Or, as our critics would say, cool as a corpse. Are you guys really ignoring this one?!Yes, we are. We’re over here like Jules and “Pumpkin” in Pulp Fiction. There might be some chaos in the diner, but we’re imploring Honey Bunny to “stay cool.”And here’s…

Jesse Cramer August 8, 2024

Should I Use My 401(k) Without a Match?

Caleb writes in this week with a SPICY question. The answer surprised me. It might surprise you too.Jesse – I work for a small company that does not currently offer a 401(k) match. Do the numb…

Caleb writes in this…

Caleb writes in this week with a SPICY question. The answer surprised me. It might surprise you too.Jesse – I work for a small company that does not currently offer a 401(k) match. Do the numbers still suggest I should utilize it? CalebWhat Are We Comparing?We need a point of comparison. If Caleb doesn’t use his company 401(k), we’re going to assume he contributes money into a normal taxable brokerage.As you’ll see, I analyzed various “employer match” percentages (100%, 50%, 0%) and also looked at skipping the 401(k) to use a taxable brokerage.The Expectatio…

Jesse Cramer July 31, 2024

Willingness, Need, and Ability: How To Determine Your Appropriate Risk

You need to understand your willingness, need, and ability to take portfolio risks. It’s an idea that straddles the line between personal preference and objective truth.Let’s break down each …

You need to understa…

You need to understand your willingness, need, and ability to take portfolio risks. It’s an idea that straddles the line between personal preference and objective truth.Let’s break down each of the three constituents, then put it all together with an example.NeedYour need to take risks relates to the amount of objective investment growth required to meet your financial goals.Understanding need starts with a comprehensive financial plan showing your projected cash flow over the next 10 or 20 years. Money in, money out, and most pertinent to today’s topic, your projec…

Jesse Cramer July 29, 2024

How Much Life Insurance Do I Need?

Friend of the blog Matt sent in a great question this week:Hi Jesse – do you have any recommendations when it comes to life insurance? I know Term is the way to go, but that’s about all I go…

Friend of the blog M…

Friend of the blog Matt sent in a great question this week:Hi Jesse – do you have any recommendations when it comes to life insurance? I know Term is the way to go, but that’s about all I got…I scanned your blog posts and didn’t see anything too specific with it but if you have any guidelines for pricing or coverage recommendations, please let me know! MattMatt’s Right. We Want Term!Matt’s right. Term life insurance is the best option in 99.99% of cases.Other types of life insurance (Whole, Variable, Universal, etc.) are bloated products that are “pushed�…

Jesse Cramer July 23, 2024

The Market Reacts to An Assassination Attempt

If you told and asked the average American, “The former President and current presidential candidate was shot in the ear on Saturday in an attempt on his life. What will the stock market do on Mond…

If you told and aske…

If you told and asked the average American, “The former President and current presidential candidate was shot in the ear on Saturday in an attempt on his life. What will the stock market do on Monday?“Doug Mills, The New York TimesI doubt many people would answer, “Ehhh – basically nothing. The market won’t care.” But the market had an unnoteworthy, “basically nothing” day on Monday, July 15. It was up 0.28%. Whoop-dee-doo.Why?Most people misunderstand what the market cares about. While individuals are undoubtedly concerned about how this assassinati…

Jesse Cramer July 15, 2024

Income vs. Savings: A Giant Misconception

It’s breakfast time, you’re hungry, and I’m offering you two options:A healthy, adult henTwo dozen eggsYour first thought is probably: “Seriously? It’s just breakfast. I don�…

It’s breakfast tim…

It’s breakfast time, you’re hungry, and I’m offering you two options:A healthy, adult henTwo dozen eggsYour first thought is probably: “Seriously? It’s just breakfast. I don’t want a live chicken running around my house.”Forget that thought for now.If you’re like me, your mind next asks, “If I do choose the chicken, how many eggs can I expect over time? What’s the risk the chicken doesn’t get to two dozen eggs? Am I willing to wait for two dozen – or hopefully more – eggs to arrive?”When we know those answers, we can make a smart decisio…

Jesse Cramer July 12, 2024

NVIDIA’s Day in the Sun(flower)

Imagine you’re a gardener. You spend a weekend building a few raised beds, planting sunflowers and corn, etc. It’s a nice little hobby. Your first summer Gardening ends up successful and fulfillin…

Imagine you’re a g…

Imagine you’re a gardener. You spend a weekend building a few raised beds, planting sunflowers and corn, etc. It’s a nice little hobby. Your first summer gardening ends up successful and fulfilling.You come back for Year 2 with vigor! You want to expand. You spend a month preparing your beds and double the size of your garden. You plant new veggies and a few flowers, and all goes well.You rinse and repeat for a few more years. Not only is your garden blooming, but its size is blooming. After years of doubling in size, it occupies a couple acres in your side field (we’re putt…

Jesse Cramer July 4, 2024

Ice and Fire and Estate Planning

Who knew a lack of proper Estate planning would throw the entire realm into war? That’s the lesson I garner from HBO’s House of the Dragon. If you’re unfamiliar (as I was) with the series, here�…

Who knew a lack of p…

Who knew a lack of proper estate planning would throw the entire realm into war? That’s the lesson I garner from HBO’s House of the Dragon. If you’re unfamiliar (as I was) with the series, here’s an uber-quick primer to catch you up.[SPOILER ALERT!]It takes place in the same universe as Game of Thrones. Semi-medieval, very political, heavy on violence and sex. House of the Dragon is set roughly ~200 years before the Game of Thrones timelineThe show chronicles the early history of House Targaryen, focusing on the events leading up to and during the Targaryen Civil War (…

Jesse Cramer June 23, 2024

The Crushing Cost of Conservative Retirement Planning

I spent 6 years in college studying mechanical engineering, and then 7 years working at an aerospace contractor where my colleagues and I designed, built, tested, and launched satellite-based telescop…

I spent 6 years in c…

I spent 6 years in college studying mechanical engineering, and then 7 years working at an aerospace contractor where my colleagues and I designed, built, tested, and launched satellite-based telescope systems.One of the features of all engineering design is the concept of “factors of safety.” Simply put, factors of safety are margins built into designs to ensure the end product can withstand physical loads beyond the expected maximum and still survive.Some typical factors of safety might include:Material Properties: Variations in material properties due to manufacturing…

Jesse Cramer June 20, 2024

“Why Can’t I Take Social Security Early and Invest It?”

Friend of the blog DT wrote in and said:In regards to your recent “When to Take Social Security” article, you left something out. You can take Social Security early (say, age 62), then inves…

Friend of the blog D…

Friend of the blog DT wrote in and said:In regards to your recent “When to Take Social Security” article, you left something out. You can take Social Security early (say, age 62), then invest that money, and your investment will end up better than if you had waited on Social Security until age 67 or age 70.Interesting! But does the math work? Let’s dive in. Should you take Social Security early and invest it?What Kind of “Returns” Do You Get For Waiting on Social Security?Let’s start by looking at Social Security. What kind of “return on investment” do yo…

Jesse Cramer June 16, 2024

10 Simple “CFP Topics” You Want to Get Right

I’m now 30 months into my new career, and I’m loving every single day.As a lifelong learner, I find the nuanced topics of financial planning and investment management to be a limitless sandbo…

I’m now 30 months …

I’m now 30 months into my new career, and I’m loving every single day.As a lifelong learner, I find the nuanced topics of financial planning and investment management to be a limitless sandbox, or perhaps more like an underground cave system. Where’s the bottom?! Nobody knows!Despite that complexity, my colleagues and I help clients with many common issues that are not the strict domain of experts. These are topics you don’t need CFPs, CPAs, or attorneys to help you with. And that fact – that even experts focus on getting the basics correct – is an important lesson.…

Jesse Cramer June 6, 2024

Do You Have a “Deeper Yes?”

I was recently listening to Michael Kitces and Carl Richards on their podcast, and they posed an amazing question:“What’s one thing that you do regularly that you’d like to stop doing?” …

I was recently liste…

I was recently listening to Michael Kitces and Carl Richards on their podcast, and they posed an amazing question:“What’s one thing that you do regularly that you’d like to stop doing?”What would you stop doing? Each of our answers will vary. It could be a destructive habit, a bad behavior, or the simple wasting of time.As their conversation continued, Carl posited this effective strategy: saying “no” becomes much easier when you have a “deeper yes.”Carl used the example of a client who chose not to pay for an expensive parking spot. Instead, that cli…

Jesse Cramer June 3, 2024

“When Should I Take Social Security?”

Thanks to reader Lynn, who wrote in this week with some specifics about her household’s situation and an overarching question: When should we start taking Social Security?I’ll provide backgrou…

Thanks to reader Lyn…

Thanks to reader Lynn, who wrote in this week with some specifics about her household’s situation and an overarching question: When should we start taking Social Security?I’ll provide background information below, and then we’ll discuss a few common “if –> then” heuristics to help you with your Social Security planning.Background – The Pros and Cons of Taking Social Security EarlySocial Security is a government program that provides financial support to individuals who are retired, disabled, or survivors of deceased workers, funded primarily through payroll taxes…

Jesse Cramer May 28, 2024

The Best Interest Podcast

"Is My 100% S&P 500 Portfolio Wrong?" | AMA with Jesse – E81

On today’s episode, we bring you something a little different. Jesse’s collected a series of questions from newsletter subscribers and will answer them in today’s AMA (Ask Me Anything). Jesse an…

On today’s episode…

On today’s episode, we bring you something a little different. Jesse’s collected a series of questions from newsletter subscribers and will answer them in today’s AMA (Ask Me Anything). Jesse answers into which accounts young people should be putting their money. Other questions answered are: Is getting to your “Coast FI” a good idea? How to balance which accounts you’re putting money into and how your goals might change that. How can you financially prepare for parenthood? Why you should diversify your investments, even if your lack of diversification is working for you. What are …

Listen · 37:43

Jesse Cramer May 21, 2024

The Value of Confidence

My friend Rocco works for a high-end tailor. A big part of their business model is the idea that a nice-fitting shirt, perfectly tailored pants, or an Italian silk suit will not only look good, but wi…

My friend Rocco work…

My friend Rocco works for a high-end tailor. A big part of their business model is the idea that a nice-fitting shirt, perfectly tailored pants, or an Italian silk suit will not only look good, but will objectively improve your life.But how?The engineer and humanist in me would balk at the idea. I have the same brain and heart in a Wal-Mart sweatsuit as I do in a Brioni. Judge me not!But when I look at the image below – same exact guy – and ask, “Which one has a better life?”…there’s a response from deep in my monkey brain. It’s Mr. Pinstripe!Of course, for…

Jesse Cramer May 21, 2024

Slam Dunk Financial Planning

I don’t watch many live sports these days. Life is busy. But I’ve caught a few quarters of NBA playoff basketball, and I’ll watch game replays while sipping morning coffee. If you’re unaw…

I don’t watch many…

I don’t watch many live sports these days. Life is busy. But I’ve caught a few quarters of NBA playoff basketball, and I’ll watch game replays while sipping morning coffee. If you’re unaware, the NBA has been revolutionized by “Moneyball” ideas over the past decade. The main “new idea” affects 3-point shots. The ratio of attempted 3-point shots has increased dramatically in recent years. Yet, despite the league’s new widespread emphasis on 3-point shots, one basketball maxim remains true: a wide-open layup or slam dunk is always worth taking. A guaranteed 2 point…

Jesse Cramer May 15, 2024

The Best Interest Podcast

Beware! Don’t Fall Into “The College Money Pit Trap!” | Evan Giokas – E80

Jesse starts this episode discussing his “50/50 rule” of college savings. Jesse also talks about 529-to-Roth conversions (why they’re overrated!), the FAFSA, and other financial tools at our dis…

Jesse starts this ep…

Jesse starts this episode discussing his “50/50 rule” of college savings. Jesse also talks about 529-to-Roth conversions (why they’re overrated!), the FAFSA, and other financial tools at our disposal for college planning. Evan Giokas then joins the show to dive deeper into a college admissions conversation. Evan is the founder of The College Confidence Coach, which helps students through their higher educational journey. Evan covers what a “conative assessment” is, how to be cost-conscious when preparing for college, how to start college conversations with your child, and the …

Listen · 1:11:34

Jesse Cramer May 7, 2024

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