Let's talk about Social Security. More than music, clothing, or even political views, Social Security might be the single biggest generational fault line in America right now. Boomers are thrilled to finally be collecting on a promise decades in the making while Millennials and Gen Z are quietly wondering if there'll be anything left by the time we get there. And honestly? That concern isn't crazy! Social Security almost certainly isn't going away entirely, but it's probably not going to look exactly the same as it does today either. Mike Piper, CPA and Social Security expert, joins the show today to explore the future of Social Security, optimal claiming strategies, and how to plan for retirement amid uncertain benefits. Specifically covered: 
What happens when the trust fund is gone?!
Downsides of overly conservative financial plans 
Claiming strategies when we’re living longer
Adjusting plans after a health diagnosis
The Open Social Security strategy calculator
Taking opportunity cost into account
Early retirement considerations
Common mistakes with DIY investors
… and plenty more!

Can’t get enough How To Money? Here are some additional ways to get ahead with your personal finances:
Mike Piper: Head over to Mike’s site, Oblivious Investor for his latest writings and Open Social Security for his free open-source strategy calculator.
Credit card perks: Check out our favorite credit cards that we use to maximize rewards and optimize our spending.
Money Gears: Knowing what to do with your money is crucial to your personal finance journey.
Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical.
Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group!

 

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!

Let's talk about Social Security. More than music, clothing, or even political views, Social Security might be the single biggest generational fault line in America right now. Boomers are thrilled to finally be collecting on a promise decades in the making while Millennials and Gen Z are quietly wondering if there'll be anything left by the time we get there. And honestly? That concern isn't crazy! Social Security almost certainly isn't going away entirely, but it's probably not going to look exactly the same as it does today either. Mike Piper, CPA and Social Security expert, joins the show today to explore the future of Social Security, optimal claiming strategies, and how to plan for retirement amid uncertain benefits. Specifically covered:&nbsp;
<ul>
<li aria-level="1">What happens when the trust fund is gone?!</li>
<li aria-level="1">Downsides of overly conservative financial plans&nbsp;</li>
<li aria-level="1">Claiming strategies when we&rsquo;re living longer</li>
<li aria-level="1">Adjusting plans after a health diagnosis</li>
<li aria-level="1">The Open Social Security strategy calculator</li>
<li aria-level="1">Taking opportunity cost into account</li>
<li aria-level="1">Early retirement considerations</li>
<li aria-level="1">Common mistakes with DIY investors</li>
<li aria-level="1">&hellip; and plenty more!</li>
</ul>
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">Mike Piper: Head over to Mike&rsquo;s site, <a href="https://obliviousinvestor.com/">Oblivious Investor</a> for his latest writings and <a href="https://opensocialsecurity.com/">Open Social Security</a> for his free open-source strategy calculator.</li>
<li aria-level="1">Credit card perks: Check out <a href="https://go.nextcard.com/shau19-htmomny">our favorite credit cards</a> that we use to maximize rewards and optimize our spending.</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>
<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">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>
</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!

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

Can Millennials Count on Social Security? w/ Mike Piper #1127

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/25773be9-ea1c-4c38-b100-b4040159b004/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:
Rent reductions
Escrow shortages
Home equity sharing
EV fees
Charity parity
Prediction market bans
Financial crunch impulse buys
Everything’s a subscription
Healthcare price hikes
Rx drug deals

 

Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
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.businessinsider.com/lower-rent-prices-landlords-tenants-homebuying-apocalypse-apartment-glut-2026-5?">Rent reductions</a></li>
<li aria-level="1"><a href="https://www.cnbc.com/2026/05/17/mortgage-escrow-shortages.html">Escrow shortages</a></li>
<li aria-level="1"><a href="https://www.cnbc.com/select/what-is-home-equity-sharing/">Home equity sharing</a></li>
<li aria-level="1"><a href="https://www.wsj.com/business/autos/driving-an-electric-vehicle-could-cost-you-an-extra-130-a-year-027f25a1?mod=hp_lead_pos10">EV fees</a></li>
<li aria-level="1"><a href="https://www.cnbc.com/2026/05/18/401k-charitable-donations.html">Charity parity</a></li>
<li aria-level="1"><a href="https://www.npr.org/2026/05/19/nx-s1-5821265/minnesota-ban-prediction-markets?">Prediction market bans</a></li>
<li aria-level="1"><a href="https://www.usatoday.com/story/shopping/deals/2026/05/10/impulse-buying-tight-budgets/89959952007/">Financial crunch impulse buys</a></li>
<li aria-level="1"><a href="https://www.nytimes.com/2026/05/12/business/subscriptions-products-services.html?">Everything&rsquo;s a subscription</a></li>
<li aria-level="1"><a href="https://www.nytimes.com/2026/05/01/business/obamacare-enrollment-decline.html?smid=em-share">Healthcare price hikes</a></li>
<li aria-level="1"><a href="https://apnews.com/article/trump-trumprx-drug-prices-health-2e4d20b1b785bbc25d3c9e5d9d4b3946?">Rx drug deals</a></li>
</ul>
&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">Credit card perks: Check out <a href="https://go.nextcard.com/shau19-htmomny">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>
<li aria-level="1">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>
&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!

Friday Flight - Rent Reductions, Charity Parity, & Home Equity Sharing #1146

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/bed911b5-dd6c-46a9-88a4-b45801328687/transcript

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!

 

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!

Optimization is everywhere in the personal finance world. If we just invest perfectly, we&rsquo;ll get where we want to go, faster&hellip; 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 <a href="https://bestinterest.blog/">The Best Interest</a>, hosts his podcast <a href="https://bestinterest.blog/personal-finance-for-long-term-investors/">Personal Finance For Long-Term Investors</a>, and today we discuss:
<ul>
<li aria-level="1">Choosing to not max Roth IRAs</li>
<li aria-level="1">How to know if you&rsquo;re Coast FIRE</li>
<li aria-level="1">Striking the balance between optimizing your finances and enjoying life</li>
<li aria-level="1">Reversion to the mean and this year&rsquo;s stock market returns</li>
<li aria-level="1">The crushing cost of conservative retirement planning</li>
<li aria-level="1">Alternative investments</li>
<li aria-level="1">Does retiring earlier mean living longer</li>
<li aria-level="1">Aligning your money with your life</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/shau19-htmomny">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!

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

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/6b805930-4645-493c-b193-b433014d2a38/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 - Pet insurance: As I’m expecting some big vet expenses, should I continue to pay for insurance for my dog?

2 - Roth vs 529: Should we save for our son’s college in a Roth since it gives us more flexibility?

3 - HSA: Can I backfill my health savings account to invest, after I pay for an expensive medical procedure?

4 - Cashless kid: What’s the best way for my 14 year old to pay for expenses while at a cashless summer camp?

5 - 0% balance transfer: Are there good balance transfer cards that have good cashback as well?

 

Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
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 Grapefruit Substance by Bissell Brothers! 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 - Pet insurance: As I&rsquo;m expecting some big vet expenses, should I continue to pay for insurance for my dog?
2 - Roth vs 529: Should we save for our son&rsquo;s college in a Roth since it gives us more flexibility?
3 - HSA: Can I backfill my health savings account to invest, after I pay for an expensive medical procedure?
4 - Cashless kid: What&rsquo;s the best way for my 14 year old to pay for expenses while at a cashless summer camp?
5 - 0% balance transfer: Are there good balance transfer cards that have good cashback as well?
&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">Credit card perks: Check out <a href="https://go.nextcard.com/shau19-htmomny">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;
During this episode we enjoyed a Grapefruit Substance by Bissell Brothers! 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!

Ask HTM – Sinking Fund or Pet Insurance, Balance Transfer Card Bonus, & Backfilling an HSA #1144

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/0e4780b8-56e8-493c-aeb1-b43c01547a6e/transcript

Can Millennials Count on Social Security? w/ Mike Piper #1127

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