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How to Money

The Case for a ‘Good Enough’ Financial Plan w/ Jesse Cramer #1145

How to Money

iHeartPodcasts

Education, Business, Investing

4.63.2K Ratings

🗓️ 27 May 2026

⏱️ 57 minutes

🧾️ Download transcript

Summary

Optimization is everywhere in the personal finance world. If we just invest perfectly, we’ll get where we want to go, faster… What's not to love?! Well, retirement planning might be a lot more like horseshoes and hand grenades, where getting close enough is actually good enough. And chasing perfection? That can come with some real downsides. Our guest today is a dear friend who brings clarity to the world of personal finance. Jesse Cramer began his career as a mechanical and aerospace engineer designing telescopes, and now brings that same precision (plus a genuine desire to help people) into the way he thinks about money. He writes over at The Best Interest, hosts his podcast Personal Finance For Long-Term Investors, and today we discuss:

  • Choosing to not max Roth IRAs
  • How to know if you’re Coast FIRE
  • Striking the balance between optimizing your finances and enjoying life
  • Reversion to the mean and this year’s stock market returns
  • The crushing cost of conservative retirement planning
  • Alternative investments
  • Does retiring earlier mean living longer
  • Aligning your money with your life
  • And much more!

 

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Transcript

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0:00.0

This is an IHeart podcast.

0:33.5

Guaranteed Human. Welcome to How to Money. I'm Joel. And today I'm talking the case for a good enough financial plan with Jesse Kramer. Okay. I'm gonna Okay, so optimization is everywhere in the personal finance world.

0:36.6

If we just invest perfectly, we'll get where we want to go faster.

0:37.7

What's not to love?

0:42.4

Well, retirement planning might be a lot more like horseshoes and hand grenades. We're getting close enough is actually good enough. And chasing perfection, well, that can come with some

0:46.9

real downsides. My guest today is one of my favorite humans in the personal finance space.

0:51.7

He's a former engineer who designed satellite telescopes. He brings that same precision, plus a genuine desire to help people into the way he thinks about money. Jesse Kramer, thanks for coming back on How to Money. Well, that's very nice to you, Joel. Very nice introduction. It's fun to be here. And I really like this topic, this idea for this episode that you put together,

1:34.1

because I've got some, I think I've got some good thoughts that hopefully the audience will like. I think so too. That's why I wanted to have you on the chat about this. But first question, first, what's your craft beer equivalent these days? What are you spending more money on than most people think is normal? But hey, it's okay because you're still being smart and thinking and investing for the future. The truthful answer there is stuff related to our two children. We've got a two-year-old,

1:39.2

she'll be two in June, and a one-month-old, both girls, two daughters. So just diapers,

1:43.7

the craft beer equivalent. But the fun answer, and maybe like the selfish answer, if it's spending on me,

2:01.7

last time I talked about racket sports. I really like racket sports. And this time I'm going to talk about hiking gear. I like hiking. I like the mountains. I like camping. So I've got a nice assortment of like more expensive than most people would ever spend on a tent. I've got that tent. So that's my answer today. So at one point,

2:17.7

we had John Mackie, the former CEO of Whole Foods on, and he talked about the, and it's so true, like when more backpacking you do, the longer distances, the more the weight matters. Like if you're going for a short couple day hikes or whatever, it's not that big of a deal. But like, if you're backpacking in the woods for weeks.

2:20.0

You need lightweight stuff.

2:36.8

And so he was like, man, I'll spend $100 to shave one ounce. And I thought that was impressive. Isn't it incredible? You're, well, it is. The Appalachian Trail starts near you in, that's right. It's in North Georgia. And if you look at the Appalachian Trail, like subreddit, you will see people talking in grams.

2:52.2

Yeah, it's really cool. It's really cool. Because otherwise, you're just like breaking your back for no reason. Okay. So I saw you, you were chatting with Andy Hill, mutual friend recently. And you, we're talking about reaching CoastFi. A lot of how to money listeners know what that means, but can you offer some details about what it looks like to achieve CoastFi? And in your

2:58.6

opinion, does it feel like just a ton of sacrifice in order to hit that goal? Yeah. Okay. Let me,

3:04.0

let me take that question in two parts. So kind of what does it look like to reach

3:09.0

Coast FI or maybe like how do I even know that I've reached Coast FI? Yeah. I guess the way that,

3:14.7

you know, my wife and I looked at it was we looked at our investable assets today, you know,

3:19.9

as we sit here at 2026 and I'm 36 years old, right? And so I say, well, if I assume a reasonable

3:26.8

rate of return on what I already have, and then I just, I take that rate of return out into

3:32.7

the future until maybe I'm 50 or 55 or 60, will I have enough money to retire two or three

...

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