The Sugar Daddy Podcast
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© 2026 The Sugar Daddy Podcast
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Ready to feel confident and in control of your money?
Welcome to The Sugar Daddy Podcast, the podcast that helps you build a clear financial plan so you can feel confident and in control of your money.
This show is for people who make “good money” but feel disorganized and unsure what steps to take next. Each episode is designed to help you turn a solid income into a real plan; one you actually understand and can act on.
Whether you’re working toward financial independence, trying to get organized, or learning how to make smarter decisions around saving, investing, budgeting, or talking about money with your partner, hosts Jess and Brandon break it all down in a way that’s simple, practical, and easy to implement.
Brandon is an award-winning, licensed financial planner and owner of Oak City Financial, with over a decade of experience helping clients across the U.S. build clear, confident financial plans.
New episodes every Wednesday.
140 Episodes
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Send a text Life insurance is one of the most misunderstood parts of financial planning. In this episode, Jessica and Brandon break down what life insurance is actually meant to do and why most people think about it the wrong way. Instead of treating life insurance like an investment, it should be viewed as income protection. If your income disappeared tomorrow, would your family still be financially secure? We cover: • Who actually needs life insurance • Why term life insurance works f...
Send a text Most emergencies cost more than $1,000. In this episode, Jessica and Brandon break down what a properly funded emergency fund actually looks like and why it’s one of the first steps in any financial plan. We cover: What counts as a true emergencyHow to calculate 6 to 12 months of expensesWhy expenses matter more than incomeWhere to keep your emergency fundWhy you shouldn’t invest itHow to automate your savingsWhat to do if you feel behindWhether you’re in a volatile industry, a du...
Send a text Tax season is here, and if you're getting a refund, this episode is for you. Jessica and Brandon break down how to use your tax refund strategically instead of treating it like random bonus money. They unpack the “free loan to the government” debate, explain why some people intentionally aim for a large refund, and walk through practical ways to put that money to work. Inside this episode: How to think about tax refunds the right wayEmergency funds and debt payoff prioritiesPlanni...
Send a text We’ve all done it. Chosen the cheapest option and told ourselves we were being smart. But sometimes cheap ends up being expensive. In this episode, Jessica and Brandon break down the difference between price and value and why understanding that distinction can completely change the way you spend, save, and invest. We share real-life examples, including: When “budget” services backfireThe hidden cost of uninvested retirement accountsWhy professional expertise often pays for itselfH...
Send a text If you feel like homeownership is out of reach, you’re not imagining it. In this episode, we break down why buying a home today is drastically harder than it was for previous generations and why this has nothing to do with lattes, avocado toast, or bad budgeting. We walk through real numbers, personal experiences, and the structural changes that reshaped the housing market after 2008. We talk about: How home prices have outpaced incomeWhy this isn’t a personal finance failureThe r...
Send a text If you've ever been confused about mutual funds, ETFs, and individual stocks, this episode is your beginner-friendly breakdown. Jessica and Brandon cut through the noise to explain what each investment type really is, how they work, and how to choose what’s right for your goals. From 401(k)s to robo-advisors to picking your own stocks, this episode helps you avoid costly mistakes and invest with clarity. You’ll learn: The pros and cons of mutual funds, ETFs, and stocksHow fees and...
Send a text A woman finds out she’s still the beneficiary on her ex-husband’s life insurance policy, years after their divorce. He’s since remarried and had a child. When he passes away unexpectedly, she’s notified she’ll receive $100,000. Now the new wife is asking for the money… for their child. In this episode, Jessica and Brandon break down the emotional, financial, and legal sides of this viral dilemma. You’ll hear: Why updating your beneficiaries is crucialWhether it’s morally wrong to ...
Send a text Are you managing money together, or living in two separate financial worlds? In this episode, Jessica and Brandon get real about a problem nearly every couple faces: one partner handling finances while the other stays out of the loop. That disconnect causes confusion, stress, and even resentment. We break down: Why this common imbalance happensThe hidden risks of not sharing financial insightHow Monarch Money can change the way you see and plan your money togetherReal life wins an...
Send a text Financial planning isn’t a one-size-fits-all game. Life happens in seasons, and your money should move with them. In this episode, Jessica and Brandon break down the 4 major financial seasons, Building, Stability, Stretch, and Harvest, and help you identify which one you’re in right now. We’re talking real-life money shifts, mindset changes, and how to give yourself grace when your financial plan needs to adapt. Whether you're stacking cash, raising kids, recovering from setbacks,...
Send a text Start the new year off right with a clear, actionable financial plan. In this episode, Jessica and Brandon walk you through five key money moves to make in January, from setting financial goals and reviewing your budget to building a debt payoff strategy and automating your savings. Whether you're managing money solo or with a partner, this episode is packed with practical advice to help you take control of your finances and build wealth in 2026. What You'll Learn: How to set meas...
Send a text Before you set another New Year’s resolution or budget goal, hit pause and reflect. In this episode, Jessica and Brandon walk you through the exact steps to do a personal money audit that sets you up to win in 2026. Whether you're feeling behind or just want a clearer plan, this episode is your financial reset. We cover: How to review your income, expenses, debt, and savings from 2025The 6 key money numbers you need to knowTools and automations that make your financial life easier...
Send a text Most people think their money problems come from a lack of budgeting. But what if the real issue is emotional? In this powerful episode, Jessica and Brandon sit down with Aja Evans, LMHC, a licensed financial therapist and author of Feel Good Finance, to break down 5 surprising signs you might need financial therapy. We talk about: The link between money trauma and poor financial decisionsWhy budgeting alone doesn’t break bad habitsHow emotional avoidance shows up in your bank acc...
Send a text Most couples don’t break up because of infidelity — they break up over money. And worse? They never saw it coming. In this episode, we’re breaking down the 5 biggest money mistakes that silently sabotage relationships… and how to actually fix them. We’re joined by Heather and Douglas Bonaparth, the real-life couple behind the new book Money Together: How to Find Fairness in Your Relationship and Become an Unstoppable Financial Team. From navigating breadwinner role shifts, to rec...
Send a text Are you walking blind when it comes to your finances? In this episode, Jessica and Brandon are going back to basics because too many people are waking up to financial realities way too late. They're breaking down why it’s so dangerous not to know where your money is, how your bills are being paid, or even what accounts exist. Whether you're married, partnered, or handling things solo, this episode will give you the tools and mindset shift to take back control. We cover: The hidden...
Send a text Ever wonder how someone with a full-time job builds serious wealth on the side? In this episode, we meet Ray Tran, a Brooklyn-based middle school teacher who has built a real estate portfolio of 583 units—all while still teaching financial literacy. We dive into: The mindset shift that led Ray from saving to investingHow he started with just one property and scaled upThe truth about passive income (and what most people get wrong)How he teaches financial literacy to middle schooler...
Send a text What would you do with a $1,200 stimulus check? In 2020, Ellie was broke, newly divorced, and raising four kids out of her mom’s house, when she made one powerful decision — to invest her $1200 stimulus check into herself. Fast forward: she’s built a multi-million dollar business empire, helped 60,000+ women, and started a new life in Senegal, where she’s continuing her entrepreneurial journey as a cafe and co-working space owner and real estate investor. In this episode, we...
Send a text Most people blow through inheritance money in just a few months. In this episode, Jessica and Brandon break down the 5-step plan to make sure a $50K windfall actually improves your life, instead of disappearing into lifestyle creep, bad investments, or impulsive spending. ✅ What to do in the first 90 days ✅ How to protect and grow sudden money ✅ Why most people get windfalls wrong ✅ Common traps with taxes, family, and fake friends Whether you inherited $50K, got a surprise bonus...
Send a text Health insurance costs are climbing, and this year’s open enrollment feels tougher than ever. Premiums are up, deductibles are higher, and plans seem designed to confuse you. In this episode, Jess and Brandon walk through how to actually compare your options by looking at total yearly cost, not just the monthly premium. You’ll learn how to plan for high-cost years with surgeries or pregnancies versus lower-cost preventive years, and how to understand how network changes, pre...
Send a text In this powerful episode, Jess and Brandon sit down with Ange Matthews, a first-generation investor and founder of The Happy Happy Method, who went from making $40K a year and battling six-figure debt to building seven-figure passive wealth. No trust fund, no finance degree, just side hustles, value investing, and mindset shifts that changed everything. You’ll learn: How Ange invested while still in debt, and why she doesn’t believe in being debt-free before building wealthWhat th...
Send a text Confused about Roth vs Traditional IRAs? You're not alone. In this episode, Jess and Brandon break down the pros, cons, and real-world impact of choosing a Roth IRA versus a Traditional IRA for your retirement game plan. Learn how taxes, income levels, and long-term growth factor into the decision, and why the right choice could save you thousands down the road. We cover: – How Roth and Traditional IRAs actually work – Which one fits different income brackets – Tax implications...
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