Our guest on this episode is personal finance writer J.D. Roth who started his blog, Get Rich Slowly in the early days of the internet- back in 2006! It’s grown to be one of the most well-respected personal finance sites around thanks to his honesty, superb writing, and desire to serve his readers. We hear all about J.D.’s history with money, whether politics belong in personal finance, the different stages of financial freedom, as well as the intersection of depression and money. And let’s not forget- we snuck in some conversation about Taylor Swift and J.D.’s lifelong devotion to his hometown soccer team!

During this episode we enjoyed a Gold by St. Archer Brewing Co- thanks to our friends at St. Archer for donating these beers to the show! And if you enjoyed this episode, be sure to subscribe and give us a quick review in Apple Podcasts or wherever you get your podcasts. Help us to spread the word to get more people doing smart things with their money!

Best friends out!

 Learn more about your ad-choices at https://www.iheartpodcastnetwork.com

Our guest on this episode is personal finance writer J.D. Roth who started his blog, Get Rich Slowly in the early days of the internet- back in 2006! It’s grown to be one of the most well-respected personal finance sites around thanks to his honesty, superb writing, and desire to serve his readers. We hear all about J.D.’s history with money, whether politics belong in personal finance, the different stages of financial freedom, as well as the intersection of depression and money. And let’s not forget- we snuck in some conversation about Taylor Swift and J.D.’s lifelong devotion to his hometown soccer team!During this episode we enjoyed a Gold by St. Archer Brewing Co- thanks to our friends at St. Archer for donating these beers to the show! And if you enjoyed this episode, be sure to subscribe and give us a quick review in <a href="https://podcasts.apple.com/us/podcast/how-to-money/id1337718773?mt=2">Apple Podcasts</a> or wherever you get your podcasts. Help us to spread the word to get more people doing smart things with their money!Best friends out! Learn more about your ad-choices at <a href="https://www.iheartpodcastnetwork.com">https://www.iheartpodcastnetwork.com</a>

Best friends Joel and Matt are the co-hosts of How to Money which is all about providing the knowledge & tools that normal folks need to thrive in areas like debt payoff, DIY investing, and crucial money tricks that will provide continuous help along your journey. We believe that access to unbiased and jargon-free personal finance guidance is more necessary than ever before. When you handle your money in a purposeful, thoughtful way that works for your lifestyle, you can really start living a rich life.

How to Money

Getting Rich Slowly & Combating Money Anxiety with J.D. Roth #138

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/79eb98b0-53e0-481a-967c-ae32003a0cf8/transcript

Time for a Friday Flight- our little sampling of the week’s best financial news and what it means for your personal finances. There are a lot of headlines out there, but we boil them down to specific takeaways that will allow you to kick off the weekend informed and help you to get ahead with your money. In this episode we explain some relevant and helpful stories like:
AI toothbrush
Car insurance competition (and divident payments!)
A time to invest
“Early” retirement increasing
Ghost jobs
Passive income dreams
HOA horrors
Living back with mom and dad
Tough sledding for realtors (Bc who actually needs a realtor?!)
Vaca thanks to AI

Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
YouTube: You thought you’d never see it… the How To Money channel over on YouTube - LIKE and SUBSCRIBE!
Credit card perks: Check out our favorite credit cards that we use to maximize rewards and optimize our spending.
Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group!
Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical.
Money Gears: knowing what to do with your money is crucial to your personal finance journey.
MG7: and maybe you’re well on your way to financial independence but you’re looking for some financial reassurance, that’s when heading over to HowToMoney.com/Advisor and getting matched with a highly vetted financial advisor makes sense.

And please help us to spread the word by letting friends and family know about How to Money! Hit the share button, subscribe if you’re not already a regular listener, and give us a quick review in Apple Podcasts or wherever you get your podcasts. Help us to change the conversation around personal finance and get more people doing smart things with their money!

 

Best friends out!

Time for a Friday Flight- our little sampling of the week&rsquo;s best financial news and what it means for your personal finances. There are a lot of headlines out there, but we boil them down to specific takeaways that will allow you to kick off the weekend informed and help you to get ahead with your money. In this episode we explain some relevant and helpful stories like:
<ul>
<li aria-level="1"><a href="https://www.bloomberg.com/news/articles/2026-09-01/dyson-announces-499-camerajet-smart-toothbrush-with-ai-built-in-camera?cmpid=090126_morningamer&amp;utm_campaign=morningamer&amp;utm_medium=email&amp;utm_source=newsletter&amp;utm_term=260901&amp;utm_content=8391">AI toothbrush</a></li>
<li aria-level="1"><a href="https://www.wsj.com/finance/auto-insurance-premiums-have-room-to-keep-falling-93243754?st=C6uPD3">Car insurance competition</a> (<a href="https://newsroom.statefarm.com/state-farm-mutual-begins-issuing-dividend-payments/">and divident payments!</a>)</li>
<li aria-level="1"><a href="https://finance.yahoo.com/economy/article/market-jitters-have-more-people-hitting-pause-on-investing-121732780.html?.tsrc=372&amp;ncid=crm_-2166470-20260625-1--A&amp;bt_user_id=MRUSO5r/zUCN1rWi+9LimNqgMQ/BxlT7sEuMUa/wm1KaNE+ZJiAwslmc2xV1KTSWNsuT2l1fzdNWYWEykZVQYHjqK8XJyfkMqFybWh76ovKr9ho9utEV9KW0LJnZ0GzH&amp;bt_ts=1782383916813">A time to invest</a></li>
<li aria-level="1"><a href="https://www.wsj.com/livecoverage/stock-market-today-dow-sp-500-nasdaq-08-11-2026/card/the-great-401-k-early-retirement-party-RuBReyc8KT8Cp8CR4LwE">&ldquo;Early&rdquo; retirement increasing</a></li>
<li aria-level="1"><a href="https://www.wsj.com/lifestyle/careers/ghost-job-ads-are-getting-so-bad-that-lawmakers-want-to-ban-them-2580bc3e?st=5cc9gT">Ghost jobs</a></li>
<li aria-level="1"><a href="https://www.wsj.com/lifestyle/careers/passive-income-dreams-2e67ee5c?st=Lyasmj&amp;reflink=desktopwebshare_permalink">Passive income dreams</a></li>
<li aria-level="1"><a href="https://finance.yahoo.com/real-estate/article/the-market-for-older-condos-is-cratering-as-buyers-shun-rising-hoa-fees-172954085.html?.tsrc=372&amp;ncid=crm_-2252049-20260817-1--A&amp;bt_user_id=VB+nmVF3TYSAbSjnLLLx5ncZ1YptsKAErkbYhnNrWmIPPVeMoonAT8oGM/giJ/H5f0ZzNmQ3vBkLS7eODw6ymyvdO5mKpPROehPoEKgdjbyNIw7+XbBku98kCyn5mEMP&amp;bt_ts=1786960996652">HOA horrors</a></li>
<li aria-level="1"><a href="https://www.usatoday.com/story/money/personal-finance/2026/08/16/college-graduates-living-with-parents/91292634007/">Living back with mom and dad</a></li>
<li aria-level="1"><a href="https://www.wsj.com/real-estate/real-estate-agents-are-quitting-the-slow-housing-market-d95fc524?st=51FCtb&amp;reflink=desktopwebshare_permalink">Tough sledding for realtors</a> (<a href="https://www.nytimes.com/2026/05/28/technology/sell-house-with-ai-no-realtor.html">Bc who actually needs a realtor?!</a>)</li>
<li aria-level="1"><a href="https://www.nytimes.com/2026/08/10/travel/ai-travel-savings.html">Vaca thanks to AI</a></li>
</ul>
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
<ul>
<li aria-level="1">YouTube: You thought you&rsquo;d never see it&hellip; the <a href="https://www.youtube.com/@HowToMoneyPod">How To Money channel over on YouTube</a> - LIKE and SUBSCRIBE!</li>
<li aria-level="1">Credit card perks: Check out <a href="https://go.nextcard.com/tkfe5ek-htmpodcast">our favorite credit cards</a> that we use to maximize rewards and optimize our spending.</li>
<li aria-level="1">Other money nerds: Find a thriving community of fellow money nerds by joining the <a href="https://www.facebook.com/groups/1623670287732189">HTM Facebook group!</a></li>
<li aria-level="1">Newsletter: Sign up for the weekly <a href="https://www.howtomoney.com/newsletter/">HTM newsletter</a>. It&rsquo;s fun, free, &amp; practical.</li>
<li aria-level="1">Money Gears: knowing <a href="https://www.howtomoney.com/start-here/">what to do with your money</a> is crucial to your personal finance journey.</li>
<ul>
<li aria-level="2">MG7: and maybe you&rsquo;re well on your way to financial independence but you&rsquo;re looking for some financial reassurance, that&rsquo;s when heading over to <a href="http://www.howtomoney.com/advisor">HowToMoney.com/Advisor</a> and getting matched with a highly vetted financial advisor makes sense.</li>
</ul>
</ul>
And please help us to spread the word by letting friends and family know about How to Money! Hit the share button, subscribe if you&rsquo;re not already a regular listener, and <a href="https://podcasts.apple.com/us/podcast/how-to-money/id1337718773?mt=2">give us a quick review in Apple Podcasts</a> or wherever you get your podcasts. Help us to change the conversation around personal finance and get more people doing smart things with their money!
&nbsp;
Best friends out!

Friday Flight - Car Insurance Competition, Early Retirement Increasing, & HOA Horrors #1188

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/1268a4a4-aba3-4c2f-aeac-b4ba00128889/transcript

Anyone else a little tired of hearing about ‘retirement?’ It can feel like this vague, far-off finish line that we're told to obsess over for decades. But here's the thing: when you look at the research, a surprising number of people who are retired—or about to retire—are anxious. They've got regrets. Some of those regrets are financial. But many have nothing to do with money at all. So if we're going to spend years working toward retirement, we should probably make sure we're aiming for one we'll actually enjoy. Joel has known Wes Moss for a long time. They worked at the same radio station for well over a decade. He's still there because, believe it or not, terrestrial radio is still alive and well. His show, Money Matters, has helped countless listeners make smarter decisions about their money, their investments, and, yes, their retirement. Wes has a new book out that challenges a lot of conventional thinking about what makes retirement successful, and today we're diving into the financial and non-financial choices that can help you avoid the regrets so many retirees have. Today we discuss:
Why his new research updates his earlier work on happiest retirees rather than replacing it entirely.
Fear around retirement is often amplified by nonstop media coverage.
Wes says more money alone does not erase anxiety, even for people with $3 million or more.
Wes defines happiness in a more Aristotelian way, focusing on fulfillment and purpose rather than pure pleasure.
He introduces “money green zones” for investable assets, income, and years left on a mortgage, arguing that happiness rises when retirees land in those ranges.
A major theme is core pursuits, which Wes describes as hobbies on steroids. The happy retiree group tends to have 5 or more, and they spend about 20 hours a week on them versus about 13 for less happy retirees.
Wes warns that purpose does not just appear in retirement. It has to be built intentionally well before leaving work.
They talk about the “friendship recession” and how it gets harder to make close friends with every decade, making community a key retirement asset.
The conversation also covers the emotional power of being able to say you could retire now, even if you choose not to. Wes says that confidence correlates with a 21% jump in happiness.
On the financial side, Wes explains why a retirement plan, safe assets, and a flexible withdrawal strategy can reduce fear and improve spending confidence.
They discuss Social Security timing, with Wes leaning toward using it sooner if doing so helps someone retire a year or two earlier and live better.
How much of a remaining mortgage leads to higher levels of happiness
And much more!

 

Can’t get enough How To Money? Here are some additional ways to get ahead with your personal finances:
Cashback credit cards: Check out our favorite credit cards that we use to maximize rewards and optimize our spending.
Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group!
Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical.
Money Gears: knowing what to do with your money is crucial to your personal finance journey.
MG7: and maybe you’re well on your way to financial independence but you’re looking for some financial reassurance, that’s when heading over to HowToMoney.com/Advisor and getting matched with a highly vetted financial advisor makes sense.

 

And please help us to spread the word by letting friends and family know about How to Money! Hit the share button, subscribe if you’re not already a regular listener, and give us a quick review in Apple Podcasts or wherever you get your podcasts. Help us to change the conversation around personal finance and get more people doing smart things with their money!

 

Best friends out!

Anyone else a little tired of hearing about &lsquo;retirement?&rsquo; It can feel like this vague, far-off finish line that we're told to obsess over for decades. But here's the thing: when you look at the research, a surprising number of people who are retired&mdash;or about to retire&mdash;are anxious. They've got regrets. Some of those regrets are financial. But many have nothing to do with money at all. So if we're going to spend years working toward retirement, we should probably make sure we're aiming for one we'll actually enjoy. Joel has known Wes Moss for a long time. They worked at the same radio station for well over a decade. He's still there because, believe it or not, terrestrial radio is still alive and well. His show, Money Matters, has helped countless listeners make smarter decisions about their money, their investments, and, yes, their retirement. Wes has a new book out that challenges a lot of conventional thinking about what makes retirement successful, and today we're diving into the financial and non-financial choices that can help you avoid the regrets so many retirees have. Today we discuss:
<ul>
<li aria-level="1">Why his new research updates his earlier work on happiest retirees rather than replacing it entirely.</li>
<li aria-level="1">Fear around retirement is often amplified by nonstop media coverage.</li>
<li aria-level="1">Wes says more money alone does not erase anxiety, even for people with $3 million or more.</li>
<li aria-level="1">Wes defines happiness in a more Aristotelian way, focusing on fulfillment and purpose rather than pure pleasure.</li>
<li aria-level="1">He introduces &ldquo;money green zones&rdquo; for investable assets, income, and years left on a mortgage, arguing that happiness rises when retirees land in those ranges.</li>
<li aria-level="1">A major theme is core pursuits, which Wes describes as hobbies on steroids. The happy retiree group tends to have 5 or more, and they spend about 20 hours a week on them versus about 13 for less happy retirees.</li>
<li aria-level="1">Wes warns that purpose does not just appear in retirement. It has to be built intentionally well before leaving work.</li>
<li aria-level="1">They talk about the &ldquo;friendship recession&rdquo; and how it gets harder to make close friends with every decade, making community a key retirement asset.</li>
<li aria-level="1">The conversation also covers the emotional power of being able to say you could retire now, even if you choose not to. Wes says that confidence correlates with a 21% jump in happiness.</li>
<li aria-level="1">On the financial side, Wes explains why a retirement plan, safe assets, and a flexible withdrawal strategy can reduce fear and improve spending confidence.</li>
<li aria-level="1">They discuss Social Security timing, with Wes leaning toward using it sooner if doing so helps someone retire a year or two earlier and live better.</li>
<li aria-level="1">How much of a remaining mortgage leads to higher levels of happiness</li>
<li aria-level="1">And much more!</li>
</ul>
&nbsp;
Can&rsquo;t get enough How To Money? Here are some additional ways to get ahead with your personal finances:
<ul>
<li aria-level="1">Cashback credit cards: Check out <a href="https://go.nextcard.com/tkfe5ek-htmpodcast">our favorite credit cards</a> that we use to maximize rewards and optimize our spending.</li>
<li aria-level="1">Other money nerds: Find a thriving community of fellow money nerds by joining the <a href="https://www.facebook.com/groups/1623670287732189">HTM Facebook group!</a></li>
<li aria-level="1">Newsletter: Sign up for the weekly <a href="https://www.howtomoney.com/newsletter/">HTM newsletter</a>. It&rsquo;s fun, free, &amp; practical.</li>
<li aria-level="1">Money Gears: knowing <a href="https://www.howtomoney.com/start-here/">what to do with your money</a> is crucial to your personal finance journey.</li>
<ul>
<li aria-level="2">MG7: and maybe you&rsquo;re well on your way to financial independence but you&rsquo;re looking for some financial reassurance, that&rsquo;s when heading over to <a href="http://www.howtomoney.com/advisor">HowToMoney.com/Advisor</a> and getting matched with a highly vetted financial advisor makes sense.</li>
</ul>
</ul>
&nbsp;
And please help us to spread the word by letting friends and family know about How to Money! Hit the share button, subscribe if you&rsquo;re not already a regular listener, and <a href="https://podcasts.apple.com/us/podcast/how-to-money/id1337718773?mt=2">give us a quick review in Apple Podcasts</a> or wherever you get your podcasts. Help us to change the conversation around personal finance and get more people doing smart things with their money!
&nbsp;
Best friends out!

Build a Retirement You'll Actually Enjoy w/ Wes Moss #1187

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/bf2bdeb2-214f-45f5-b5b9-b4a301312916/transcript

We’re kicking off the week by answering your listener questions! And if you have a question that you’d like for us to answer on the show, we’d love for you to submit your own via HowToMoney.com/ask , send us your voice memo. Regardless of how random or bizarre you might think it is, we want to hear it!

 

1 - Extra cash: Should we use our savings to pay down a mortgage that’s at 2.8% for 30 years?

2 - Brokerage taxes: How do I prepare for paying taxes on dividends and could you explain ‘tax drag’?

3 - Credit card apps: Am I crazy for feeling hesitant to enter my credit card information into card maxing apps?

4 - Hot and tired: Our window units aren’t keeping up with the heat so is it OK to finance central air?

 

Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
YouTube: You thought you’d never see it… the How To Money channel over on YouTube - LIKE and SUBSCRIBE!
Credit card perks: Check out our favorite credit cards that we use to maximize rewards and optimize our spending.
Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group!
Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical.
Money Gears: knowing what to do with your money is crucial to your personal finance journey.
MG7: and maybe you’re well on your way to financial independence but you’re looking for some financial reassurance, that’s when heading over to HowToMoney.com/Advisor and getting matched with a highly vetted financial advisor makes sense.

During this episode we enjoyed a Forgotten Lake by Lake of the Woods Brewing… thank you David S for sending this one our way! And please help us to spread the word by letting friends and family know about How to Money! Hit the share button, subscribe if you’re not already a regular listener, and give us a quick review in Apple Podcasts or wherever you get your podcasts. Help us to change the conversation around personal finance and get more people doing smart things with their money!

 

Best friends out!

We&rsquo;re kicking off the week by answering your listener questions! And if you have a question that you&rsquo;d like for us to answer on the show, we&rsquo;d love for you to submit your own via <a href="https://www.howtomoney.com/ask/">HowToMoney.com/ask</a> , send us your voice memo. Regardless of how random or bizarre you might think it is, we want to hear it!
&nbsp;
1 - Extra cash: Should we use our savings to pay down a mortgage that&rsquo;s at 2.8% for 30 years?
2 - Brokerage taxes: How do I prepare for paying taxes on dividends and could you explain &lsquo;tax drag&rsquo;?
3 - Credit card apps: Am I crazy for feeling hesitant to enter my credit card information into card maxing apps?
4 - Hot and tired: Our window units aren&rsquo;t keeping up with the heat so is it OK to finance central air?
&nbsp;
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
<ul>
<li aria-level="1">YouTube: You thought you&rsquo;d never see it&hellip; the <a href="https://www.youtube.com/@HowToMoneyPod">How To Money channel over on YouTube</a> - LIKE and SUBSCRIBE!</li>
<li aria-level="1">Credit card perks: Check out <a href="https://go.nextcard.com/tkfe5ek-htmpodcast">our favorite credit cards</a> that we use to maximize rewards and optimize our spending.</li>
<li aria-level="1">Other money nerds: Find a thriving community of fellow money nerds by joining the <a href="https://www.facebook.com/groups/1623670287732189">HTM Facebook group!</a></li>
<li aria-level="1">Newsletter: Sign up for the weekly <a href="https://www.howtomoney.com/newsletter/">HTM newsletter</a>. It&rsquo;s fun, free, &amp; practical.</li>
<li aria-level="1">Money Gears: knowing <a href="https://www.howtomoney.com/start-here/">what to do with your money</a> is crucial to your personal finance journey.</li>
<ul>
<li aria-level="2">MG7: and maybe you&rsquo;re well on your way to financial independence but you&rsquo;re looking for some financial reassurance, that&rsquo;s when heading over to <a href="http://www.howtomoney.com/advisor">HowToMoney.com/Advisor</a> and getting matched with a highly vetted financial advisor makes sense.</li>
</ul>
</ul>
During this episode we enjoyed a Forgotten Lake by Lake of the Woods Brewing&hellip; thank you David S for sending this one our way! And please help us to spread the word by letting friends and family know about How to Money! Hit the share button, subscribe if you&rsquo;re not already a regular listener, and <a href="https://podcasts.apple.com/us/podcast/how-to-money/id1337718773?mt=2">give us a quick review in Apple Podcasts</a> or wherever you get your podcasts. Help us to change the conversation around personal finance and get more people doing smart things with their money!
&nbsp;
Best friends out!

Getting Rich Slowly & Combating Money Anxiety with J.D. Roth #138

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