Best Jackie Cummings Koski Podcasts (2025)

1
When the Job Crumbles: Preparing for Life's Surprises (SB1646) 1:04:50

2d ago1:04:50

1:04:50

Ever experienced the gut-wrenching moment of losing a job—or worried about what you’d do if it happened? Today, we tackle how to prepare, what to do immediately, and the smartest moves to protect your finances if your job ever disappears. From building an emergency fund to making the most of employer benefits, we’ll walk you through the steps to ke…

1
Innovation, XBox and Your Financial Plan (SB1645) 1:22:58

4d ago1:22:58

1:22:58

Feeling stuck in your financial plan—or maybe just in life in general? Whether it’s your money, career, or day-to-day habits, a little innovation can go a long way. Today, we’re breaking down how to rethink and restructure your approach to financial planning and work-life balance using lessons from Microsoft (yes, the Xbox folks). Dean Carignan and…

1
Banishing The Burden of Student Loan Debt | Travis Hornsby | 122 1:07:26

4d ago1:07:26

1:07:26

We're pulling back the curtain on student loans with expert and founder of Student Loan Planner, Travis Hornsby. Initially impacting younger borrowers, the student loan crisis now affects those in their 40s, 50s, and even 60s. The balances are getting bigger, lasting longer and rules are becoming more complex! It can be confusing, but this episode …

151
How Does a Money Nerd Think About "Romance"? (SB1644) 59:54

7d ago59:54

59:54

Love is in the air—and so are overpriced flowers, extravagant dinners, and some serious credit card regrets. In today’s episode, we tackle the financial pressure of Valentine’s Day and show you how to keep the romance alive without setting your wallet on fire. Joining us are financial pros Jesse Cramer, Sarah Catherine Gutierrez, and Len Penzo, who…

1
Spending Experiments: Learn What Purchases Make You Happy | E160 Carl Jensen 55:52

8d ago55:52

55:52

Struggling to spend money? Same here. Honestly, I never thought this would be a problem as I got closer to financial independence. I mean, isn’t the goal to save up enough so we can finally spend on the things we want? Turns out, after 15 years of working hard to build wealth, it’s not so easy to let go. Add in some good old financial insecurities,…

1
Wall Street Creates (Yet Another) Hilariously Bad Investment Product (SB1643) 1:12:09

9d ago1:12:09

1:12:09

Just when you thought Wall Street had run out of ways to package up risky investments and slap a shiny label on them—here we go again. Today, Joe and OG break down yet another overcomplicated, high-fee, and completely unnecessary financial product. Whether it’s preying on investor fears, promising market-proof returns, or just outright nonsense, we…

1
Are You On Speaking Terms With Your Wallet? (SB1642) 1:17:32

11d ago1:17:32

1:17:32

Swipe right on financial stability or get ghosted by your savings? While Joe's mom yells upstairs about who left the empty milk carton in the fridge (seriously, who does that?), we’re diving into the messy, complicated, and sometimes hilarious world of your relationship with money. Are you in a stable, long-term commitment with your finances, or ar…

1
Attorney Spilling all the Legal Tea on Estate Planning | Jenny Rozelle | 121 1:03:39

11d ago1:03:39

1:03:39

Attorney Jennifer (Jenny) Rozelle joins us to unravel the complexities of estate planning and help you get your estate plans in order. In this episode she covers the essentials- healthcare directives, probate, wills, beneficiaries, trusts and more. She's a lawyer with a sense of humor and sprinkles in her special blend of wit and wisdom to liven up…

1
How To Use Our #1 Key To Money Management Success (SB1641) 1:08:34

14d ago1:08:34

1:08:34

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 membe…

1
Yet Another Insurance To Avoid (SB1640) 55:40

16d ago55:40

55:40

What do scammers, fancy doors, and Twinkies have in common? Turns out, more than you think! Today, Joe, OG, and Doug take you on a wild ride through financial scams, fraud prevention, tax implications of dual residency, and... the surprising link between door quality and financial stability. (Yeah, we didn’t see that one coming either.) What’s Insi…

1
Redefining Retirement with Benjamin Brandt (SB1639) 1:11:05

18d ago1:11:05

1:11:05

Retirement planning isn’t about waiting until 65—it’s about setting yourself up for a life you love starting right now! Today, Certified Financial Planner Benjamin Brant joins us to challenge traditional retirement thinking. What We Cover: ✅ Retirement planning starts now, not later – Why waiting to plan is the biggest mistake you can make. ✅ Dream…

1
"Mama, Are We Poor?”: a Single Mom's Millionaire Mindset | Monica Scudieri | 120 52:42

19d ago52:42

52:42

Monica Scudieri started late on her financial independence journey but finished early. Her financial watershed moment was when she discovered she had $257,000 in debt. She was in serious financial despair but managed to slowly dig out. The progress she made was impressive and just ten years later, she reached financial independence. In this episode…

1
The Case Against Early Retirement (SB1638) 1:02:01

21d ago1:02:01

1:02:01

Ever dreamt of quitting your job early and sipping piña coladas on a beach? Before you tell your boss what to do with that job and start booking your one-way ticket to paradise, today’s roundtable might make you think twice. Join Jesse Cramer from The Best Interest, Paula Pant from Afford Anything, and our own OG as they break down the case against…

1
Fast-Track Your 2025 Money Goals Using These Strategies | E159 Justin Brown-Woods 42:53

22d ago42:53

42:53

It’s the start of a new year, and you’ve set some financial goals like paying off student loans, saving for a down payment, or maxing out your IRA. Whatever your goal, how awesome would it feel if you could fast-track your progress? It’ll take focus and dedication, but with the right strategies, you can turbocharge your cash flow and get there fast…

1
Unpacking a Rare Vanguard Target Date Fund Problem (SB1637) 59:36

23d ago59:36

59:36

Ever wondered if you’re better off building your own target date fund instead of relying on a one-size-fits-all option? We’re diving into whether crafting your own investment mix is worth the effort, potentially saving you fees and giving you more control over your portfolio. But even the pros get it wrong sometimes—just ask Vanguard. We’re coverin…

1
Is Your Brain Blocking Your Financial Goals? (with Jessica Moorhouse) SB1636 1:14:36

25d ago1:14:36

1:14:36

What’s really standing between you and your financial goals? In today’s mentor, Jessica Moorhouse—financial counselor, podcast host, and author of Everything But Money—joins Joe to dive into the mental and emotional side of managing money. Jessica shares her journey with therapy, how relationships shape our financial habits, and the role of self-ta…

1
Leaning Out: Cracking the Burnout Code | Dawn Baker | 119 53:34

26d ago53:34

53:34

Ever felt burnout creeping into your life? Then join us for this discussion about tackling the widespread issue of burnout with Dr. Dawn Baker, author of the book 'Lean Out'. Discover practical advice for high-powered professionals struggling with exhaustion, cynicism, and lack of motivation. Whether you're an overworked physician, a stressed corpo…

1
These Are Our Community's Biggest Money Monsters (SB1635) 1:09:48

28d ago1:09:48

1:09:48

Do financial boogeymen haunt your dreams? You’re not alone. Today, we’re diving into the worries that keep even the most seasoned finance nerds up at night. From concerns about index fund concentration to the fear of market manipulation and obsession with asset allocation, this episode tackles it all with insight and a healthy dose of perspective. …

1
Taking it to the Streets: Best Pro Tips for Late Starters | FinCon Attendees | 118 12:09

30d ago12:09

12:09

In this episode, we're taking it to the streets of Atlanta, GA where the 2024 FinCon took place. FinCon is the largest (and funnest) conference for independent content creators in the personal finance space. We wish you could have been there but since we couldn't bring our audience to FinCon, we're bringing a little FinCon to you. We chatted with s…

1
Can You Find More Cheddar By Navigating Volatile Markets? (SB1634) 54:32

1M ago54:32

54:32

Feeling like the stock market is a high-stakes game of pinball lately? Not sure how to steady your hand when it comes to retirement accounts? In this episode, we tackle the rollercoaster of market volatility with actionable strategies to keep your retirement plans on track. Learn how to create an Investment Policy Statement, whether a Roth IRA stil…

1
Navigating Debt, Crypto Scams, and Social Media's Wild West (with Natalia Brown) SB1633 SB 1:06:25

1M ago1:06:25

1:06:25

Feeling overwhelmed by debt or unsure how to navigate the fast-paced world of financial advice online? We’ve got you covered! This episode features Debt Relief Advocate Natalia Brown from National Debt Relief, who shares practical tips to climb out of financial trouble and steer clear of predatory practices. But that’s not all—we dive into the Wild…

1
Retirement Remix: Crafting Financial Futures with Purpose | Christine Benz | 117 46:13

1M ago46:13

46:13

In this episode we welcome back Christine Benz, director of personal finance and retirement planning for Morningstar. Christine is one of the most respected thought leaders on the topic of retirement and shares insights from her new book, 'How to Retire'. We discuss the importance of preparing for retirement well in advance, building social network…

1
Our Magic 8 Ball Predicts Our Financial Future (SB1632) 1:31:53

1M ago1:31:53

1:31:53

Ready to ring in the new year with a twist? On this episode of Stacking Benjamins, we consult the one and only Magic 8-Ball to make our bold predictions for 2025. Will the stock market be riding high, or is it headed for a tumble? What’s next for Bitcoin, and can Taylor Swift’s love life predict the future? Join Joe, OG, Len Penzo, and Mindy Jensen…

1
What Happens After I Reach FIRE? Withdrawal Strategy, Spending Changes, & Finding Meaning | E158 Jeremy Schneider 51:31

1M ago51:31

51:31

Since discovering financial independence, I have focused on wealth-building: choosing the right accounts, investing wisely, and cutting expenses to save more. But now that I’m approaching my FIRE number, a new question has emerged—what happens after I reach financial independence? On one hand, there’s the technical side: What’s the best way to with…

1
Live For Today? Lessons from Oversavers (SB1631) 1:07:51

1M ago1:07:51

1:07:51

Can you save too much? Spoiler alert: absolutely. On today’s episode, Joe, OG, and Neighbor Doug tackle a financial pitfall many Stackers don’t think about—oversaving. Yes, socking away cash for the future is important, but at what cost? People often work extra hours, miss family dinners, skip vacations, and end up with regret instead of memories. …

1
Taking Control of Your Life and Finances (with Anthony O'Neal) SB1630 1:19:07

1M ago1:19:07

1:19:07

Feeling like life’s demands have you tied up in knots while your financial future seems like a moving target? Time to take charge! Today in the basement, Anthony O'Neill pulls up a chair and shows you how to claim the head seat at your own table. He breaks down the power of having a personal vision, making intentional decisions that align with your…

1
Value-Based Spending: The Latte Chronicles | Jen Smith & Jill Sirianni | 116 56:46

1M ago56:46

56:46

In this episode, we talk with Jen and Jill from the Frugal Friends Podcast and authors of the new book Buy What You Love Without Going Broke. They believe the secret to saving money isn’t in coupons and sales, it’s in identifying what you value and pursuing it unapologetically. We chat about how value-based spending can meet higher emotional and ps…

1
Avoid These Financial Blunders in 2025 with Smart Money Moves (SB1629) 1:02:23

1M ago1:02:23

1:02:23

Feeling a little queasy about your financial plans for 2025? Fear not! Today, Joe steps out of the cozy basement and straight into the bustling chaos of Manhattan to bring you top-tier advice from some of the brightest financial minds. Joined by Paula Pant from Afford Anything, Nick Magiulli, author of the Of Dollars and Data blog, and Doc G from t…

1
Finding Little P Purpose: A Conversation with Dr. Jordan Grumet (SB1628) 1:18:42

1M ago1:18:42

1:18:42

Does finding purpose in life feel overwhelming? What if you didn’t need a “grand” purpose to find meaning? Today, Dr. Jordan Grumet (AKA Doc G) joins us to explore the concept of “little P” purpose—those smaller, everyday moments that bring joy and fulfillment. From Julia Child’s journey to surprising stories of purpose in unexpected places, this e…

1
How to Buy What You Love Without Going Broke in 2025 (SB1627) 1:14:12

2M ago1:14:12

1:14:12

What if you could spend guilt-free on what you love and keep your finances on track? In this episode, we’re joined by Jen and Jill from the Frugal Friends podcast to break down how to live frugally without crossing the line into being cheap. Frugal living isn’t about deprivation—it’s about prioritizing your spending on what truly lights you up whil…

1
The pURPOSE Code | Jordan Grumet | 115 57:13

2M ago57:13

57:13

In this episode we are joined by the multi-talented Jordan Grumet, a hospice doctor, storyteller, and the host of the award-winning 'Earn & Invest' podcast. Jordan shares insights from his latest book, 'The Purpose Code', diving deep into the nuances of Big 'P' vs Little 'p' purpose, legacy, and finding true happiness. From his personal journey fro…

1
How To Make $100M Dollars in 2025 - Part 2 (with Alex Hormozi) SB1626 1:11:45

2M ago1:11:45

1:11:45

What’s the secret to growing your income? In part two of our conversation with business dynamo Alex Hormozi, we explore the mindset shifts, skill-building tactics, and high-impact strategies that can take your earning potential to the next level. Whether you’re an entrepreneur or climbing the corporate ladder, this episode is packed with actionable…

1
Anxiety-Free Purpose: Framework for Creating Purpose in Your Life | E157 Jordan Grumet 46:38

2M ago46:38

46:38

Why save and invest? It’s a rhetorical question, but let’s think it through. When you save and invest, you’re sharing financial resources with your future self. This means your future self won’t have to worry about earning money. With that financial freedom, you gain time—the time you would’ve spent working. And with more time, you have more freedo…

1
How To Make $100M Dollars in 2025 (with Alex Hormozi) SB1625 1:12:03

2M ago1:12:03

1:12:03

What would you do with $100 million a year? Today, we unpack Joe’s insightful conversation with business mogul Alex Hormozi, who breaks down the steps to massively increasing your income. Spoiler alert: It’s not about clipping coupons—it’s about thinking bigger, stacking the right skills, and taking strategic risks. Whether you’re an entrepreneur o…

1
Building a Billion Dollar Empire with Ryan Serhant (SB1624) 1:20:08

2M ago1:20:08

1:20:08

How do you go from a struggling actor to the top of the real estate world? Rounding out our greatest hits week of epic shows, we time travel back to when Ryan Serhant, star of Million Dollar Listing New York and the new Netflix series Owning Manhattan, shared his journey from rock bottom to building a billion-dollar real estate empire. In this epis…

1
Weathering Financial Storms | Kristen Knapp | 114 1:04:29

2M ago1:04:29

1:04:29

After 28 years of playing the weather girl on TV, Kristen Knapp moved to part time work to follow her passion for travel planning for the financial independence (FI) community. She shares her fascinating backstory of growing up in poverty, dealing with childhood money trauma, becoming a successful broadcast meteorologist, and ultimately achieving F…

1
Paul Merriman Builds Your Million-Dollar Roadmap to Success (SB1623) 1:22:41

2M ago1:22:41

1:22:41

What’s the secret to turning small, consistent actions into million-dollar results? Legendary financial educator Paul Merriman joins the basement crew to share his powerful principles for building wealth, including the critical role of diversification and the magic of target date funds. Whether you’re just starting or refining your portfolio, Paul’…

1
Zoe Chance Shows You How Influence Is Your Superpower (SB1622) 1:19:27

2M ago1:19:27

1:19:27

For this next installment to this edition of our Greatest Hits Week, we throw it back to a conversation Joe had with Zoe Chance about how to make influence your superpower. Do you ever feel like you just don’t have much influence over others? Not in a negative way, but in a way where you wish people would truly hear you. Sometimes we just need to t…

1
FINCON Jeopardy | Justin Peters, Joel Larsgaard & Justin Brown-Woods | 113 1:01:37

2M ago1:01:37

1:01:37

We love games so today we're bringing you a podcast takeover and having some fun with 'Money Jeopardy'! This was recorded live at FinCon 2024 (a conference for personal finance content creators) with 'The Struggle is Real' podcast, hosted by our friend Justin Peters. He’s joined by Jackie Cummings Koski (your co-host on 'Catching Up to FI'), Joel L…

1
Beyond the Numbers: James Rhee's Recipe for Success through Kindness (SB1621) 1:17:29

2M ago1:17:29

1:17:29

How can kindness and a little math transform not just a company but an entire outlook on life? In this episode, we’re joined by James Rhee, who shares his remarkable journey from venture capitalist to CEO of a company dedicated to inclusivity and empowerment for plus-size Black women. James opens up about the values instilled by his Korean immigran…

1
Doug and the Three Ghosts: A Financial Holiday Tale (SB1620) 1:05:29

2M ago1:05:29

1:05:29

What happens when Doug gets visited by three ghosts in the basement? A classic holiday story gets a Stacking Benjamins twist in this special episode. Inspired by A Christmas Carol, we explore lessons from the past, present, and future to help you make smarter money moves. From learning to avoid past financial missteps to balancing life’s experience…

1
Balancing End of Year Cheer With Your Long Term Goals (SB1619) 1:18:26

2M ago1:18:26

1:18:26

The holiday season is here, and while it’s a time for celebration, it can also throw a curveball at your health and financial goals. In this episode, we’re joined by Angelo Poli from MetPro, who shares his no-nonsense approach to managing holiday indulgences without sacrificing all the progress you’ve made. Think of it as building a resilient portf…

1
Tactical Tips and Tripwires: The DIY Financial Planner's Guide | Cody Garrett | 112 1:05:39

2M ago1:05:39

1:05:39

Happy Holidays! Join us for this lighthearted chat with a longtime friend of the show, Cody Garrett, CFP. He shares his list of the 24 common DIY investment mistakes that might be hindering your path to financial independence and some tips on how to fix them. He steps us through the list which includes things like underutilizing employer benefits, …

1
Did 2024 Just Rewrite the Rules of Investing? (SB1618) 1:09:17

2M ago1:09:17

1:09:17

As 2024 winds down, we’re taking a look back at the year that was—its challenges, its surprises, and the financial lessons we’ve all had to learn (sometimes the hard way). Whether you’re strategizing for big goals in 2025, making sense of unpredictable markets, or just trying to stay one step ahead of inflation, this episode has you covered. We’ve …

1
Creative Frugality: How to Do A Lot With A Little | E156 Jill Sirianni 50:01

2M ago50:01

50:01

Who says you can’t have your cake and eat it too? With a little bit of creative frugality, I think it is possible to live below your means and buy the things that bring you joy. What do I mean by creative frugality? It is a two-part process. Number 1, identify the things you value and stop spending money on the things you don’t. That is what today’…

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Jackie Cummings Koski Podcasts

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