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.
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 learn:
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:
Your credit score doesn’t define you—but it does impact...
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 bill into long-term financial damage.
You’ll learn:
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 post-nuptial agreement after nine years of marriage—not as a plan for divorce, but as a blueprint for how they handle money, co-parenting, and conflict with intention.
They walk through how they worke...
*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, they unpack how a childhood shaped by financial uncertainty led to a life of intentional wealth-building.
From a full ride to Wellesley to living on Peace Corps stipends, Charly eventually found their money ...
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 episode breaks down the alphabet soup of money terms that keep smart, successful people stuck.
No jargon. No fluff. Just the knowledge banks hope you never Google.
Visit prenups.com/sugardaddy to learn more about...
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 memories are likely still shaping your current habits.
You’ll learn:
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 self-worth, and your ability to think clearly.
In this episode, they unpack the debt-stress spiral, why even high earners aren’t immune, and how shame keeps so many people silently suffering. If...
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 budgeting for braces to navigating tough talks with aging parents, great advisors help you make money decisions that align with your life, not just your portfolio. And sometimes? Their job is reminding yo...
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 "perfect" moment.
They call out outdated advice that tells you to wait, and show you how to grow wealth while paying off debt. You’ll learn why index funds are your low-risk, high-impact secret we...
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:
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 business—all with one goal in mind: freedom. From day one, she designed her company to run without her, documenting every process, system, and role. So when a horseback riding accident sidelined her, the bus...
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 incomes don't stretch as far as they used to.
Ready to break free from the high-income trap? Tune in for an honest conversation about navigating today's complex financial landscape and wh...
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), Kia is tackling a startling reality: the average financial literacy age in the UK is just nine years old.
Join Jess and Brandon as they discuss Kia's journey from early mone...
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:
• Educational accounts like 529 plans
• Custodial investment accounts (UTMAs)
• Custodial Roth IRAs
• How business owners can employ their children for tax advantages
Visit prenups.co...
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 it’s going to push you into a "higher tax bracket" or assumed your entire income gets taxed at your highest rate, then this conversation will transform your understanding of ho...
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 futures, and find fulfillment both within and beyond their parenting roles.
In this episode we talk about about:
-The market value of a SAHMs unpaid labor and hidden opportunity costs
- Financial prot...
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) to comprehensive financial planning.
In this episode we discuss:
• How AI excels at portfolio management
• How budgeting apps use AI to categorize transactions and provide spen...
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 credential, how it can significantly increase your salary, and the experiences Tamara has gathered throughout her career. Whether you’re considering the PMP or not, this episode is filled with ca...
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 should have about their finances.
In this episode:
- Discussing the importance of post-nuptial agreements
- Unpacking insights from their attorney about preparing for the unex...
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
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