The Stacking Benjamins Show

Roundtable discussion with Kitty and Piggy from 'Bitches Get Riches' on money's role as a tool vs. status symbol. Trivia contest on Gilligan's Island. Balancing financial goals and self-care. Navigating money control and investment decisions. Exploring psychological roots of spending habits. Portfolio allocation strategy and debt paydown methods with humor.

Were so worried about the Benjamins, the job, the success ladder, and getting "the things" that sometimes we forget to live. Guy Kawasaki was in the room when the iconic Apple "Think Different" campaign was created. He believes that "Think Different" isn't enough today. In his words, "You can be different and still suck." It's time for a higher target, and that target is "remarkable." But how do you get there? We'll detail everyting from the findings of Carol Dweck to the work of Jane Goodall to parse what "remarkable" truly means. In Guy Kawasaki's world, it means surfing. It means questioning your beliefs. It means learning how to ask better questions.Before that we cover a disturbing headline: FinTech company Chime and company-with-a-reputation-of-dishonesty Robinhood are better regarded than products which compete against them offered by big names like Vanguard and Fidelity. Why are younger investors and savers trusting these names over the heavyweights? That's good news, right? Maybe. We'll share what we think this means and also what you should do about it when thinking about where to park your hard-won dollars.Of course, we'll also take a question from a Stacker in need AND share Doug's trivia question! On the back porch, we also announce some new meetup dates. Come out and join us!FULL SHOW NOTES: https://www.stackingbenjamins.com/how-to-live-your-best-life-best-self-guy-kawasaki-1486Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

So many new businesses start every year, only to fail weeks or months later. Sadly, many of the missteps these would-be business owners made could have been presented if they'd followed some fairly simple steps. CPA Michele Cagan not only owns her own small business, she counsels many business owners with their taxes and their business plans. She joins us today to share some of the most essential nuggets new business owners and side hustlers need to know, from her new book, Starting a Business 101.In our headline segment, Capital One has acquired Discover. What does this mean for Discover and Capital One cardholders and clients? We'll dive into all of the details and what experts are predicting will happen to the benefits cardholders of each company can expect. Good news no matter whether you're a Discover or Capital One customer...experts seem to believe things are looking up across the board.Of course, we'll also share a TikTok minute AND discuss backdoor Roth IRAs, mega-backdoor Roth IRAs (aka - "Doug's Mom IRAs"), and much, much more. Of course, we save time to wander out to the back porch and share our favorite films and television shows...and others we don't care for so much.FULL SHOW NOTES: https://www.stackingbenjamins.com/how-to-start-a-business-101-michele-cagan-1485Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

We round out Rewind Week with an episode from The Earn & Invest Podcast.This is a current events/community Thursday episode featuring an Earn & Invest community member Ian Kist. We are also joined by Joe Saul-Sehy from The Stacking Benjamins Podcast. Today we discuss current articles about Crypto and Indexing that seem to be diametrically opposed. Who is right?This show originally aired on January 25, 2024, so ignore any mention of current events. To see the original show notes, visit Community Episode: Crypto vs S&P 500 Index Smackdown — Earn & Invest (earnandinvest.com).Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Jason Tartick shares his journey from banker to pursuing what he loves. Fidelity's State of Retirement Planning survey results discussed. Financial confidence impacts due to the pandemic highlighted. Excess Roth IRA contribution question answered. Doug's amazing trivia rounds off the show.

We kick off our Rewind Week with an episode from our sister show, Stacking Deeds.Asking questions is the key to making connections, and today we connect with top Manhattan real estate broker Vickey Barron! She'll teach YOU how to ask the right questions to buy the right properties and build the right team. In our headlines, scams are on the rise....so what are some of the biggest real estate scams? We'll share. And speaking of share...I'll share some trivia that travels coast to coast.This show originally aired on August 15, 2023, so ignore any mention of current events. To see the original show notes, visit The Inquisitive Investor: Vicki Barron on How Asking Questions Elevates Your Real Estate Game (stackingdeeds.net).FULL SHOW NOTES: http://stackingbenjamins.com/sb-rewind-stacking-deeds-vickey-barron-1482Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Over the course of your life, would you prefer to feel special or happy? If you can only choose one in your life, which one would you choose and feel like you made the most of it? That's the topic for our roundtable discussion today. We're joined by our very special guest Dana Anspach, CFP®, RMA®, Kolbe Certified™ Consultant, and Founder & CEO of Sensible Money, LLC. She's joined by our in-house sourpuss OG and Len Penzo, creator of the award-winning blog lenpenzo.com.Our panel discusses whether achieving "happy" or "special" is necessarily an either/or decision, or if there's some middle ground between the two. Joe goes on to clarify that the author's definition of "special" centers around addiction to professional success: addicted to being hardworking, successful, and wealthy. We tackle why many success-focused people are actually "miserably rich." Do you have to sacrifice your happiness in order to achieve professional success, or is there a way to have the best of both worlds?In the second half of the discussion, sponsored by DepositAccounts.com, we dive into how to overcome workaholism, so you avoid being miserable and wealthy. Is shedding materialism in favor of simplicity the secret to maintaining a healthy balance between success and happiness?Stay tuned for Doug's amazing big-money question. Will Dana propel Paula into a 3-way tie for first place or will OG or Len take sole possession of the lead?FULL SHOW NOTES: https://www.stackingbenjamins.com/balancing-success-and-happiness-1481Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Learn the art of supercommunication with bestselling author Charles Duhigg. Dive into the evolving insurance industry, understanding dividends, and effective goal-setting in conversations. Join the hosts for engaging banter, tech challenges, vulnerability in communication, and exciting meetup plans.

Why aren't you making those big strides you're hoping for in your career, personal life, or with your money? Today we talk about the building blocks of success, which contrary to popular belief, isn't being "special" or taking a "big leap." It's getting the little things correct. Dr.'s Resa Lewiss and Adaira Landry join us to dive into tweaking some of the skills they've found can give you the largest boost with the least amount of effort, to increase your income, experience life more, and ultimately not just stack more Benjamins, but stack more worthwhile moments.Before that we share a headline that could save you thousands of dollars in taxes. One popular tax expert looks at the thousands of layoffs recently and finds some lemonade in the job-loss lemons of life. We explore one tax strategy we haven't discussed in a long, long time...and it could be your biggest tax break ever.Of course, we also share a great idea in the TikTok minute, Doug's amazing trivia, and more!FULL SHOW NOTES: https://www.stackingbenjamins.com/micro-changes-for-big-results-1479Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Have you heard about the new Apple Vision Pro that was recently launched? Are you an early adopter, or are you waiting for the price to be cut and the kinks to be worked out? Here to discuss the new world reality of augmented reality and virtual reality, we're joined by Certified Financial Coach and co-host of the hit couples' finance podcast For Better & Worth, Ericka Young. She is joined by Doc G of the Earn & Invest podcast and our very own OG.Is this amazing new technology worth its $3,500 price tag? Is there room in your budget for it? Or is it a justifiable "I'll figure it out later" type of expense? We discuss the pros and cons of being on the cutting edge, when it's acceptable (or not) to pull the trigger on a big, not-totally-necessary expense.Plus, stick around for our latest installment of Doug's year-long trivia game. Will Doc G make Len proud, will Ericka put Paula Pant on the board, or will OG take this week's prize?In the second half of the show, sponsored by DepositAccounts.com, we dive into why the fact that the Apple headset is so good it is actually a problem.FULL SHOW NOTES: https://www.stackingbenjamins.com/spend-or-save-priorities-ericka-young-1478Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices