On today's show we're taking your letters, but first, we're talking to Hannah Rounds, our favorite tax software reviewer, who gives us the lowdown on the good, bad and ugly of tax software. She'll tell us which brands to avoid, which are her favorites, and which packages are surprising. Whether you're willing to pay for your tax support or are looking for the best software package for free, we'll dive into all of the brands to help make your filing season easier.

We're happy that the government shutdown is over for now, but what if it happens again in three weeks? We'll talk to Lacey Langford from the Mil Money Movement podcast about the fallout from the shutdown. If people are trying to duct tape together their financial picture until the receive their first paycheck after the shutdown, what do they do? We'll discuss resources, advice, what NOT to do, and more.

Later on, we'll throw out the Haven Life Line to Pete, who wants to know if he should invest some of his extra cash into a short-term bond fund. He has a large cash reserve, and with interest rates being very low on savings accounts, he wonders whether it'd be worth the time to spike up the interest rate possibilities a little.

And don't worry... we'll still take some time for Doug's trivia.

Thanks to the Murder Book Podcast for supporting StackingBenjamins. Check out Michael Connelly's new Murder Book podcast wherever you get your podcasts, or at MurderBookPodcast.com.

Thanks to LinkedIn for supporting Stacking Benjamins.  Go to LinkedIn.com/sb and get a $50 credit toward your first job post.

What does it really mean to be poor? We're not talking about poverty...that's a whole different issue, when compared to one article we're discussing today, which covers the difference between people who are "poor" but own lots of stuff and people who are "rich" and own very little. What do we mean? We'll dive in to this topic today with our roundtable group of bloggers and podcasters, including Cody Berman, co-host of the FI Show; Len Penzo of LenPenzo.com; and from our own Stacking Benjamins podcast, OG. Plus, we'll take a call from Tyler, who has some stock market questions about 2019. Can the Magic 8 Ball possibly help him with his issue? And, if that isn't enough, we'll also answer a question from the mailbag!

Halfway through the show we'll take a break and talk tax prep with Katherine Pomerantz of The Bookkeeping Artist. Katherine brings some great information on how to get your books organized for this year's tax season, and some advice that'll hopefully keep a bit of your hair on your head through April's filing season. ...and of course, we'll still have time for Doug's trivia.

Thanks to OnDeck for sponsoring the show. For a free consultation with one of their US-based loan specialists, go to OnDeck.com/SB.

Thanks to Skillshare for sponsoring the show. Start your two months of unlimited access to Skillshare by visiting SkillShare.com/SB.

Learn more about your ad choices. Visit podcastchoices.com/adchoices

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

What does it really mean to be poor? We're not talking about poverty...that's a whole different issue, when compared to one article we're discussing today, which covers the difference between people who are "poor" but own lots of stuff and people who are "rich" and own very little. What do we mean? We'll dive in to this topic today with our roundtable group of bloggers and podcasters, including Cody Berman, co-host of the FI Show; Len Penzo of LenPenzo.com; and from our own Stacking Benjamins podcast, OG. Plus, we'll take a call from Tyler, who has some stock market questions about 2019. Can the Magic 8 Ball possibly help him with his issue? And, if that isn't enough, we'll also answer a question from the mailbag!

Halfway through the show we'll take a break and talk tax prep with Katherine Pomerantz of The Bookkeeping Artist. Katherine brings some great information on how to get your books organized for this year's tax season, and some advice that'll hopefully keep a bit of your hair on your head through April's filing season. ...and of course, we'll still have time for Doug's trivia.

Thanks to OnDeck for sponsoring the show. For a free consultation with one of their US-based loan specialists, go to OnDeck.com/SB.

Thanks to Skillshare for sponsoring the show. Start your two months of unlimited access to Skillshare by visiting SkillShare.com/SB.

With all of the news dominated lately by the government shutdown and Washington politics, it's easy to focus on things outside of your control. But if you're going to become a millionaire, it's time today to refocus your energy on YOU and what you need to do personally to find your way toward financial success. The perfect person to talk to about personal responsibility comes down to the basement today, Chris Hogan. We'll dispel some of the myths around who's a millionaire and help you set up your plan of attack to join the ranks yourself....sooner rather than later.

In today's headlines: will the government shutdown impact this year's tax return season? Even with a partial recall of IRS employees, there's still plenty of potential issues if the agency doesn't return to full strength. We'll discuss one piece today that takes a look at all the possible problems for individuals and businesses alike.

Plus, we'll be throwing out the Haven Life Line to Matt, who is recently married. What are some resources available for newlyweds going through their first tax season? After that we'll take some time to answer a letter from Jon, who wonders if his wife should ditch her whole life policy for term life insurance, and invest the difference in a Roth.

And don't worry... we'll still have time for Doug's trivia.

Thanks to Skillshare for sponsoring the show. Start your two months of unlimited access to Skillshare by visiting SkillShare.com/SB.

Thanks to OnDeck for sponsoring the show. For a free consultation with one of their US-based loan specialists, go to OnDeck.com/SB.

Learn more about your ad choices. Visit podcastchoices.com/adchoices

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

With all of the news dominated lately by the government shutdown and Washington politics, it's easy to focus on things outside of your control. But if you're going to become a millionaire, it's time today to refocus your energy on YOU and what you need to do personally to find your way toward financial success. The perfect person to talk to about personal responsibility comes down to the basement today, Chris Hogan. We'll dispel some of the myths around who's a millionaire and help you set up your plan of attack to join the ranks yourself....sooner rather than later.

In today's headlines: will the government shutdown impact this year's tax return season? Even with a partial recall of IRS employees, there's still plenty of potential issues if the agency doesn't return to full strength. We'll discuss one piece today that takes a look at all the possible problems for individuals and businesses alike.

Plus, we'll be throwing out the Haven Life Line to Matt, who is recently married. What are some resources available for newlyweds going through their first tax season? After that we'll take some time to answer a letter from Jon, who wonders if his wife should ditch her whole life policy for term life insurance, and invest the difference in a Roth.

And don't worry... we'll still have time for Doug's trivia.

Thanks to Skillshare for sponsoring the show. Start your two months of unlimited access to Skillshare by visiting SkillShare.com/SB.

Thanks to OnDeck for sponsoring the show. For a free consultation with one of their US-based loan specialists, go to OnDeck.com/SB.

We're dedicating this episode to a very special guest: YOU. Our mailbag is overflowing, so today we realized it was time to devote a whole episode to answering your burning questions. Scott has cash left over after he pays bills and maxes out his regularly scheduled savings contributions... should he open up a Roth IRA? How should Laura prioritize her savings goals: pay down debt, add to retirement accounts, or build her emergency funds? Tyler has been recruited by his local Edward Jones agent. Should he begin his career with them?

In our headlines segment, one recent piece asks the question, "Is your debt the driving factor behind your savings discussions?" We'll tackle why that's an issue, and how it can harm your long term plans. In our second headline we'll look at some changes coming this year to health savings accounts (HSAs).

Later on, we'll throw out the Haven Life Line to John, who wants to know how to invest his lump sum. Should he dollar cost average over the next year or dump his stash of money into his account at one time?

And don't worry... we'll still take some time for Doug's trivia.

Thanks to MagnifyMoney.com for sponsoring Stacking Benjamins. MagnifyMoney.com saves users on average $450 when they compare, ditch, switch and save on credit cards, student loan refinancing, checking, savings and more. Check out MagnifyMoney.com for your savings.

Thanks to Grammarly for supporting Stacking Benjamins. For 20% off a Grammarly premium account, go to Grammarly.com/sb.

Learn more about your ad choices. Visit podcastchoices.com/adchoices

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

We're dedicating this episode to a very special guest: YOU. Our mailbag is overflowing, so today we realized it was time to devote a whole episode to answering your burning questions. Scott has cash left over after he pays bills and maxes out his regularly scheduled savings contributions... should he open up a Roth IRA? How should Laura prioritize her savings goals: pay down debt, add to retirement accounts, or build her emergency funds? Tyler has been recruited by his local Edward Jones agent. Should he begin his career with them?

In our headlines segment, one recent piece asks the question, "Is your debt the driving factor behind your savings discussions?" We'll tackle why that's an issue, and how it can harm your long term plans. In our second headline we'll look at some changes coming this year to health savings accounts (HSAs).

Later on, we'll throw out the Haven Life Line to John, who wants to know how to invest his lump sum. Should he dollar cost average over the next year or dump his stash of money into his account at one time?

And don't worry... we'll still take some time for Doug's trivia.

Thanks to MagnifyMoney.com for sponsoring Stacking Benjamins. MagnifyMoney.com saves users on average $450 when they compare, ditch, switch and save on credit cards, student loan refinancing, checking, savings and more. Check out MagnifyMoney.com for your savings.

Thanks to Grammarly for supporting Stacking Benjamins. For 20% off a Grammarly premium account, go to Grammarly.com/sb.

How do you put the brakes on spending so much money? ....... Our special guest today is Ashley Feinstein Gerstley, author of The Thirty Day Money Cleanse, and she's an expert in cleaning up your budget. We'll talk with her and our team about a recent Budgets Are Sexy blog post in which blogger J. Money lays out how he avoids spending money. What games do you play with yourself to distract yourself from spending money. Plus, two contributors you know and love, Len Penzo from the LenPenzo.com blog, and from Afford Anything, Paula Pant.

Halfway through the roundtable we'll take a break for our Friday Fintech segment and talk to DeAnn O'Donovan from AHP Servicing. AHP Servicing is a company that's setting out to help people who are struggling with their mortgages find ways to stay in their homes.

We'll also answer a MagnifyMoney.com question from Paul, who has the opportunity to buy shares of a new company. He's sure the price is going to jump up. Should he use he cash he has on hand to buy shares, or take out a loan to get even more shares?

And of course, we'll still have time for Doug's trivia.

Thanks to Masterworks for supporting Stacking Benjamins. Visit Masterworks.io and reserve your shares now. See disclaimer at Masterworks.io/disclaimer.

Learn more about your ad choices. Visit podcastchoices.com/adchoices

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

How do you put the brakes on spending so much money? ....... Our special guest today is Ashley Feinstein Gerstley, author of The Thirty Day Money Cleanse, and she's an expert in cleaning up your budget. We'll talk with her and our team about a recent Budgets Are Sexy blog post in which blogger J. Money lays out how he avoids spending money. What games do you play with yourself to distract yourself from spending money. Plus, two contributors you know and love, Len Penzo from the LenPenzo.com blog, and from Afford Anything, Paula Pant.

Halfway through the roundtable we'll take a break for our Friday Fintech segment and talk to DeAnn O'Donovan from AHP Servicing. AHP Servicing is a company that's setting out to help people who are struggling with their mortgages find ways to stay in their homes.

We'll also answer a MagnifyMoney.com question from Paul, who has the opportunity to buy shares of a new company. He's sure the price is going to jump up. Should he use he cash he has on hand to buy shares, or take out a loan to get even more shares?

And of course, we'll still have time for Doug's trivia.

Thanks to Masterworks for supporting Stacking Benjamins. Visit Masterworks.io and reserve your shares now. See disclaimer at Masterworks.io/disclaimer.

Could you go a few days without spending any money? A few weeks? How about a few months? Starving your wallet might be simpler than you've previously thought. Jen Smith, co-host of the Frugal Friends podcast, joins us today to talk about gifting yourself a "No Spend Challenge." How does it work? We'll cover her story of spending little to no money to cure her debt issues, and then how she refined the concept to create a plan worthy of talking about on our show and elsewhere!

And in our headlines segment of the podcast, some great news! Long term care benefits have been added to the new crop of Medicare Advantage plans. We'll invite Danielle Kunkle Roberts from Boomer Benefits over so we can all learn more. Plus, we'll take a look at recent changes in the annuity industry. Annuity providers are making a combined effort to bring the industry into the 21st century to speed up the exchange process from months to a week. What does that mean for you? We'll dive in more during our headlines segment.

Later on, we'll throw out the Haven Life Line to Sean, who's a minority stakeholder in a corporation. The majority stakeholder wants to buy him out... what questions should Sean be asking?

And don't worry... we'll still have time for Doug's trivia.

Thanks to Omax Health for supporting Stacking Benjamins. Visit TryOmax.com/sb for your free box of Omax3 Ultra-Pure with your first purchase.

Learn more about your ad choices. Visit podcastchoices.com/adchoices

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.