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The Stacking Benjamins Show

How To Use Our #1 Key To Money Management Success (SB1641)

Feb 7, 2025   •   1 HOUR 7 MIN
Is automating your finances the key to effortless money management, or a one-way ticket to financial autopilot disaster? Paula Pant, Jesse Cramer, and Doc G join us to navigate the fine line between automation genius and accidental money mayhem. Done right, automation saves you time and stress. Done wrong? You might be funding a forgotten gym membership for the next five years. 😬 What’s Inside This Episode? 💰 The Power of Automation – How strategic automation can make your financial life simpler, more efficient, and stress-free. 🤖 What to Automate & What to Keep Manual – Should you set bills to auto-pay, or will that lead to mysterious charges on your credit card? 📊 High-Tech Money Tools: Are They Worth It? – Todoist, Notion, and other techy automation tricks—are they game-changers or just digital clutter? 💡 Personal Automation Hacks – How the panel automates their finances like pros (without losing control of their money). 🎭 The Dark Side of Automation – Horror stories of overdraft surprises, vanishing paychecks, and auto-pay regret. 📢 Stacker Debate: Should You Automate Everything? – The great automation showdown—when automation helps and when it hurts. ✨ Special Bonus: The Worst Things to Automate – Some things should NEVER be on autopilot. Find out what financial automation fails made our list. Takeaways for Smart Stackers: ✅ Automation = Freedom (When Used Wisely). The right balance saves you time while keeping you in control. ✅ Auto-pay is great—until it isn’t. Track subscriptions and bills so you don’t end up paying for things you don’t use. ✅ Manual check-ins keep you financially sharp. Even with automation, you need to review your money regularly. ✅ Tech tools can help—but they’re not magic. The best system is the one you actually use. 🎧 Hit play now and rethink your approach to automation before it outsmarts you! Learn more about your ad choices. Visit podcastchoices.com/adchoices

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The Stacking Benjamins Show

How Pros Build Motivation Into an Effective Financial Plan (SB1659)

Ever wonder why some people crush their financial goals while others keep hitting snooze? Today, we’re talking about the secret sauce behind sticking to a financial plan—and no, it’s not just “wanting it more” (though that helps). Joining Joe in the basement is OG, alongside personal finance expert Jesse Kramer from The Best Interest and CFP Dana Anspach from Sensible Money. Together, they’ll break down why staying financially motivated is harder than it looks—and how to actually keep yourself on track, even when life (or a killer sale on Amazon) tries to derail you. We’ll explore why people resist financial planning (hint: it’s not always laziness), how goal-setting psychology plays into money habits, and why tracking your finances can be as powerful as tracking your fitness. Dana shares the surprising link between logging your retirement balance and saving more, while OG and Jesse tackle the age-old debate: should financial advisors be more like sports agents—pushing, coaching, and sometimes delivering the tough love? Plus, we dig into why writing things down actually works (seriously, it’s science) and how a simple mindset shift can help you finally take action. And of course, what’s a Friday without Doug’s trivia? This week, Doug takes us back to the boxing ring with a question about the legendary Joe Louis—and the sucker punch that is junk fees. ? Our roundtable throws their best guesses into the ring, but who will come out on top? Play along and see if you can take home the trivia belt! This was a great finish to a week of talking motivation and drive! From the seven steps to dynamic drive to sports agent Molly Fletcher on Wednesday and this discussion, it's a well-rounded week that should help you get up and go...even if you think YOUR get up and go got up and went. FULL SHOW NOTES: https://stackingbenjamins.com/motivation-habits-and-planning-1659 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

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The Stacking Benjamins Show

Climb Out of Your Rut: Molly Fletcher on Creating Sustainable Motivation (SB1658)

Ever feel like you're stuck in a rut, spinning your wheels, or just running low on motivation? Today, we crack the code on sustaining drive and avoiding complacency with former sports agent Molly Fletcher, who’s worked with some of the biggest names in sports and has been dubbed the female Jerry Maguire. She breaks down the fine line between contentment and coasting, plus shares keys to staying at the top of your game—from managing energy to embracing adversity like a pro. But wait, there’s more! Len Penzo (yes, of LenPenzo dot com fame!) joins us as guest co-host, bringing his usual mix of wisdom, dry wit, and probably a few thoughts on sandwich prices. And if you think motivation is tough, try navigating the world of credit—because while ambition is great, bad credit can still trip you up. From student loan pitfalls to practical credit repair tips, we cover what younger folks (and honestly, all of us) need to know about keeping those numbers in check. In this episode: Molly Fletcher on Peak Performance – Lessons from a top sports agent on how to stay motivated without burning out. Complacency vs. Contentment – Are you stuck or simply satisfied? Molly breaks it down. Managing Energy Like a Pro – Tom Izzo swears by it, and so should you. Credit Crash Course – What happens when student loans go delinquent, and how to fix the damage. The Living Without Credit Debate – Is a debt-free life possible, or just a financial myth? Doug & OG’s Ski Slope Disaster – A story of poor decisions, gravity, and bruised egos (hilarious in retrospect). Len Penzo's Tips for Improving Credit Scores – Because nobody budgets quite like Len. Whether you need a motivation boost, a credit check-up, or just a good laugh at Doug’s expense, this episode has you covered. 🎧 Tune in for wisdom, financial hacks, and some après-ski storytelling you won’t want to miss! FULL SHOW NOTES: Add show notes url here. Be sure to please include https://www at the beginning of the show notes url that makes it clickable on YouTube Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

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The Stacking Benjamins Show

How to Use Process to Create Sustainable Drive (SB1657)

Ever start a new financial goal feeling unstoppable, only to lose momentum when life gets in the way? Staying motivated isn’t just about working harder—it’s about working smarter. Today, Joe and OG take a deep dive into Dynamic Drive, the key to keeping your financial momentum going without burnout. We’ll break down the seven essential pillars—mindset, energy, discipline, curiosity, resilience, connection, and confidence—so you’re ready to hit the ground running when we welcome former sports agent Molly Fletcher on Wednesday. 💰 In this episode: Why motivation fizzles out—and how to make it last The seven keys to Dynamic Drive (and how to apply them to your finances) How milestones and energy management keep you on track Tax strategies for selling shares—FIFO, LIFO, or average cost? Which method helps you keep more of your hard-earned Benjamins? What cowboy fencing teaches us about peak performance (yes, that’s a thing) Plus, Doug serves up a sports trivia challenge—because what’s financial motivation without a little fun? 👉 Listen in now and get fired up—without burning out! FULL SHOW NOTES: https://stackingbenjamins.com/how-to-create-a-sustainable-drive-1657 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

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