Many of us grew up hearing, “Winners never quit, and quitters never win.” But when it comes to a toxic job or bad investment, quitting can be the absolute best choice — as long as you do it right. Former professional poker player Annie Duke built her career on knowing when to hold and when to fold. She joins us to talk about why it’s so crucial for us to be able to cut our losses, and how we can make that decision with confidence. In Mailbag, we discuss the best ways to stash our savings.

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Tax day is just around the corner, and we’ve got tax expert Robbin Caruso here to answer all of your biggest questions. We hear from one listener who’s wondering whether state stimulus checks count as taxable income, and another who isn’t sure if she needs to pay quarterly taxes. We also tackle questions about changing your filing status on your W-4, and tax strategies to keep in mind when using a 529 college savings plan.

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Since the start of the pandemic, a record number of people have undergone a “great money reset” — they’ve quit their jobs, changed careers, retired early, or started new businesses. So, how do we make these changes happen financially? CBS News business analyst Jill Schlesinger joins us to break down how you can do your own great money reset by analyzing your money, curbing your spending, and throwing financial assumptions out the window. In Mailbag, we answer questions about estate planning and working as an independent contractor. In Thrive, the secret money habits of super savers.

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We all assume that our money is safe in our bank accounts, but what happens when it’s not? Peter Polson, CEO of budgeting spreadsheet company Tiller Money — which had almost all of its funds stored at Silicon Valley Bank — joins us to talk about his experience navigating the recent crisis. Plus, he shares the top lessons individuals should take from the bank’s failure, including ways we can all better protect ourselves from financial instability.

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Have you ever thought about what you might regret at the end of your life? What if there was a way to know what those regrets are right now? Hospice doctor Jordan Grumet has heard firsthand from his patients about what they wish they’d done differently, and he’s published those insights in his book, “Taking Stock.” Jordan joins us to talk about how we can all achieve a fulfilling and regret-free life, and how we can use money as a tool to help us get there. In Mailbag, we answer questions about organizing financial documents and finding a financial advisor. In Thrive, free tax tips for 2023.

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Pets are a part of our families — but they can also be expensive. That’s why we’re here to answer all your questions about budgeting for your furry friends, and we’ve got a pet expert on board to help us. Rob Jackson is the founder and “Chief Pet Protector” at Healthy Paws, a pet insurance plan, and he’s also the creator of the Healthy Paws Foundation. Rob and Jean tackle questions about how to determine a pet’s temperament before you adopt, whether you should set aside savings in advance for unexpected treatments, how pet insurance works for older animals, and more.

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In this episode, we’re tackling personal finance for Gen Z, a generation that’s new to the working world and getting ready to shake up the economy. Gen Z financial adovocate Taylor Price joins us to break down the biggest money challenges facing her generation (hello, crypto and FOMO), and she also shares her tips for gaining financial knowledge and independence. In Mailbag, we answer questions about investing in crypto and the best way to pay for a car. In Thrive, how to invest in your health.

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No, money conversations aren’t always easy — but they are always important. On this week’s episode we’re talking about all things friendship and money — which are two very complicated topics that get even more complicated when we throw them together. Jen Smith and Jill Sirianni, co-hosts of the Frugal Friends Podcast, break down how we can talk money with our BFFs, and why we should be doing more of it. In mailbag, we cover backdoor Roths and RMDs, and in Thrive, how to sell your stuff for cash. 

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We’re officially in the middle of tax season, and this year's filing deadline of Tuesday, April 18th will be here before we know it. Tax expert and CPA Robbin Caruso of Prager Metis International joins us to discuss the biggest changes to the tax code over the past year, the most common mistakes she sees people make on their returns, and strategies to make your tax prep as successful and stress-free as possible.

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We’re joined by an expert in hard work and endurance — Paralympian Oksana Masters, who has competed (and won) against the best of the best in rowing, cross-country skiing, cycling, and the biathlon. The 17-time Paralympic medalist shares her journey to becoming one of the world’s leading athletes, the obstacles she’s encountered along the way, and her advice for how all of us can build resilience in our own careers. In Mailbag, we read a note from an audiologist on the importance of hearing health and answer a question about solo 401(k)s. In Thrive, everything you need to know as a first-time homebuyer.

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