The Sugar Daddy Podcast
Ready to normalize talking about money? Then welcome to The Sugar Daddy Podcast. Every episode will get you one step closer to your financial goals. Whether that is learning how to invest, budget, save, retire early or simply make better money choices, Jess & Brandon have got you covered in a way that's easy to understand, and easy to implement. Tune in as they demystify the realm of dollars, so it all makes cents, while giving you a glimpse into their relationship with money and each other.
Brandon is an award winning licensed financial planner, and owner of Oak City Financial, with over a decade of experience and millions of dollars managed for his clients all over the United States.
New episodes published the first three Wednesdays of every month.
Episodes
109 episodes
96: Spencer Howard on Unlocking Luxury Travel Through Credit Card Strategy
What if luxury travel wasn’t just for the 1%? In this episode, travel rewards expert Spencer Howard reveals how everyday spending can unlock first-class flights, champagne service, and global adventures—without going into debt.You’ll lea...
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Season 4
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Episode 95
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54:01
95: How to Build and Defend Your Credit Like a Pro
Think your credit score is just a number? Think again. In this episode, Jess and Brandon break down the five key components of your FICO score—and why they matter more than you think.Learn how to:Boost your score with smart, ...
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Season 4
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Episode 95
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29:04
94: Is Putting Medical Bills on a Credit Card a Mistake?
Medical debt affects over 100 million Americans, but many don't realize the financial consequences of how they choose to pay it. In this episode, Jessica and Brandon break down why using a credit card for medical expenses can turn a manageable ...
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Season 4
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Episode 94
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29:16
93: Writing Our Own Rules: Details of our Post-Nuptial Agreement
Most couples unknowingly agree to their state’s version of a prenup when they sign a marriage license. But what if you could rewrite the rules to actually reflect your values?In this episode, Jess & Brandon share why they created a p...
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Season 4
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Episode 93
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43:47
92: From Undocumented to Financially Free: Charly Stoever’s Money Journey
*This episode contains profanity and may not be suited for children under age 13 Charly Stoever has worn many hats—undocumented immigrant, stockbroker, money coach, and global adventurer. In this raw and inspiring conversation, the...
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Season 4
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Episode 92
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46:30
91: APR, APY, WTF? The Jargon That’s Keeping You Broke
Financial jargon isn’t just annoying—it’s expensive. Banks bank on the fact that most people don’t really know what terms like APR, APY, and amortization actually mean. That confusion? It could be costing you thousands.This epis...
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Season 4
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Episode 91
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33:07
90: Rewriting Your Money Story with Financial Therapist Wendy Wright
Your money story isn’t just about numbers—it’s about emotions. In this powerful episode, financial therapist Wendy Wright unpacks why 80–90% of our financial decisions are emotionally driven—and how your earliest money memor...
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Season 4
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Episode 90
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54:42
89: Money and Mental Health: How Finances can Affect Your Wellbeing
May is Mental Health Awareness Month—and Jess and Brandon are talking about one of the biggest, most ignored triggers of anxiety and depression: money stress. Financial pressure doesn’t just hurt your bank account—it hijacks your sleep, your se...
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Season 4
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Episode 89
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34:42
88: How Financial Advisors Help With Real Life—Not Just Your Portfolio
Think financial advisors just pick stocks? Think again. In this episode, Jess and Brandon unpack what really makes an advisor invaluable—hint: it’s not yelling into phones like Wolf of Wall Street.From planning maternity leave and budget...
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Season 4
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Episode 88
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20:45
87: Why Waiting to Invest Is Keeping You Broke
Think you need to be debt-free or have a fat savings account before you invest? That myth is keeping you broke. In this episode, Jess and Brandon break down why starting now—even with just $5—is more powerful than waiting for the "perf...
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Season 4
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Episode 87
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32:25
86: Rethinking Your 6 Month Emergency Fund
Layoffs, inflation, and rising costs are rewriting the rules of emergency savings. In this episode, Jess & Brandon break down why the old "3-month cushion" no longer cuts it—and what you actually need instead.You’ll learn:
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Season 4
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Episode 86
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29:34
85: Building a Seven-Figure Hands Off Business with Trina Julian
What do free lunch money, a horse, and a seven-figure landscaping company have in common? Trina Julian.In this episode, Jess and Brandon dive into how Trina built Country Girl Gardens from a $10K side hustle into a seven-figure ...
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Season 4
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Episode 85
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58:05
84: Six Figures and Still Struggling: The $250K Middle Class Trap
Money that once supported entire families now barely covers daycare costs, leaving many six-figure earners wondering: Is $250,000 the new middle class? Jess and Brandon are tackling this financial reality shift head-on, exploring why high incom...
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Season 4
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Episode 84
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33:10
83: How to Handle Money with Kia Commodore
In this episode, you’ll get to meet Kia Commodore, the 26-year-old financial literacy powerhouse who's changing how young people in the UK think about money. As founder of Pennies to Pounds and author of "How to Handle Money" (HarperCollins), K...
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Season 4
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Episode 83
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47:15
82: How to Make Your Kids Millionaires
In this episode, Jess and Brandon dive into strategies to build significant wealth for your children through early and consistent investing, leveraging the incredible power of compound interest. In this episode we discuss:• Educ...
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Season 4
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Episode 82
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35:27
REWIND: How Your Income Actually Gets Taxed
In this episode, Brandon and Jess break down the mechanics of tax brackets and discuss how the progressive tax system is widely misunderstood, often leading to make costly financial mistakes. If you've ever worried about taking a raise because ...
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Season 4
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12:04
81: Money Moves for Stay at Home Moms with Jenni Sisson
Jessica and Brandon sit down with finance writer and stay at home mom, Jenni Sisson. They discuss her journey from being a stay-at-home mom to personal finance writer while explaining how mothers can build wealth, protect their financial future...
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Season 4
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Episode 81
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55:02
80: Should You Trust AI to Replace Your Financial Advisor?
Financial planners and AI tools can coexist to provide better service, with each bringing different strengths to the financial planning process. In this episode Jess and Brandon discuss the rise of robo-advisors and how they compare (and don’t)...
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Season 4
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Episode 80
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47:12
79: A Fast-Track To Your PMP: 30 Days to Certification with Tamara McLemore
Discover how to fast track your career by obtaining the PMP certification in weeks, instead of the traditional 6-8 months, with Tamara McLemore's innovative Boot Camp. In this episode, Jess and Brandon dive into the importance of this credentia...
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Season 4
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Episode 79
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45:02
78: Why We Decided on a Post-Nuptial Agreement
After almost nine years of marriage, Jess and Brandon decided to get a postnuptial agreement. In this episode, they dive into the process of creating their post-nuptial agreement, their experience, and the crucial conversations every couple sho...
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Season 4
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Episode 78
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27:38
77: Rip & Rant on DE&I, Relationship Disconnects and Etiquette
In this episode, Jess and Brandon tackle the critical issue of diversity, equity, and inclusion (DE&I) in the current socio-political climate, debunking myths and misconceptions surrounding these initiatives. They emphasize the importance o...
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Season 4
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Episode 77
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42:51
76: Eve Rodsky on Rebalancing Equity and the Price of Unpaid Labor in your Home
Ever found yourself buried under household tasks, wondering why the balance feels so off? In this episode, Jess and Brandon unravel the complexities of invisible work with Eve Rodsky, author of "Fair Play" and "Find Your Unicorn Space," as she ...
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Season 4
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Episode 76
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1:17:32
75: How to Navigate Student Loan Debt with Attorney Stanley Tate
Known for his practical and accessible guidance, Stanley Tate, an expert attorney in student loan law, has become an indispensable resource for student loan borrowers of diverse backgrounds. In this conversation, Jessica and Brandon dive ...
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Season 4
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Episode 75
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1:03:35
74: Practical Tips for Raising Financially Confident Kids with Maya Corbic
This episode explores the critical theme of teaching children financial literacy and responsibility, framed through the experiences of Maya Corbic. Maya is a Canadian based CPA and author of a kids’ book "From Piggy Banks to Stocks: The U...
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Season 4
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Episode 74
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53:28
73: How to Successfully Navigate a Layoff: Jessica's Personal Story
In this episode, Jessica shares her personal journey of being laid off from a Fortune 100 tech company and the steps she took to navigate this transition with strategy & resilience. The conversation delves into managing emotions during layo...
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Season 4
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Episode 73
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54:01