Episodes

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 worked with attorney Aaron Thomas to build a post-nup that protects th...

*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 “aha moment” in a simple stock market chart—leading to a career...

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 fair prenups that help couples plan for a healthy fina...

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: How to spot hidden money patterns rooted in childhood A simple reframe that helps couples stop fighting about "money" Why debt often triggers shame—and what to do about it How to start healing your relat...

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 you’ve ever avoided your account balance or felt like you’re f...

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 you it’s okay to spend the money you’ve saved. If you want peace...

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 weapon, and exactly how to start investing—even if you're overwhelmed or ...

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: Why experts now recommend a 12-month emergency fund How to separate wants vs. needs when calculating your savings target Why investments ≠ emergency savings (and what to do instead) 5 practical strategies to build your fund faster—without burnout How to turn a daunting ...

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 business kept thriving—thanks to her standard operating procedures...

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 what you can do to stretch your dollar Visit prenups.com/sugardaddy to lea...

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 money lessons, to running her first business and the lessons in between that helped sha...

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.com/sugardaddy to learn more about fair prenups that help couples plan for a healthy financial...

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 how taxation actually works. Whether you're early in your career or an establishe...

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 protections and considerations for SAHMs -Side hustles and per...

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 spending insights • How comprehensive financial planning differs from simple inve...

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 career advice to help you level up at any stage. What you’ll learn abou...

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 unexpected - Examining family dynamics and financial planning - Sharing their perspecti...

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 of understanding DE&I as a framework that benefits everyone, while urging personal reflection on inherent biases. Brandon also challenges the men who are resisting financial advising, when their spouses are clearly asking for help and looking for support. Las...

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 shares the often-unseen challenges of unpaid labor in relationships. The discussion reveals the significant emotional and cognitive burdens women face as the typically designated caregivers and home managers, underlining the need for equitable partnership ...

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 into the complexities of the student loan debt landscape and its emotional toll on borrowers. From navigating federal, private and Parent PLUS loans, to strategies for finding relief through repayment options and bankruptcy, this episode is packed with expert in...

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 Ultimate Guide for a Young Investor" and the founder of the Wealthy Kids Investment Club. Her popular Instagram account @teach.kids.money inspires parents to raise financially independent kids. This episode is packed with practical strategies for engaging discus...

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 layoffs, understanding severance packages, job searching strategies, and the importance of networking. Jessica and Brandon dive into: • Sharing Jessica's layoff experience and emotional response • Importance of understanding severance packages and your finances •...

This episode dives deep into understanding your 401K and retirement options through employers, emphasizing the importance of maximizing contributions, especially around employer matches. Key topics include auto-enrollment processes, investment options, Roth vs. pre-tax contributions, and what to do when changing jobs or needing to access funds. • Importance of understanding employer matches • Differences in auto enrollment versus manual enrollment • Contribution percentages and how to adjust th...

In this episode, Jess and Brandon unveil their D.R.E.A.M framework for couples, designed to facilitate meaningful discussions about money by focusing on emotional connections rather than just numbers. They explore the importance of diving into personal money histories, reflecting on their impact, engaging in shared goals, taking action, and ongoing management to foster strong financial partnerships. If you’re ready to have better conversations about money with your partner in 2025, then this ep...