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 talk about money with your partner, Jess & Brandon have 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 every Wednesday.
Episodes
123 episodes
110: How to Maximize Your Employee Benefits When Premiums Keep Rising
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 act...
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Season 4
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Episode 110
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44:17
109: Six-Figure Debt to Seven- Figure Wealth with Ange Matthews
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...
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Season 4
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Episode 109
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1:01:42
108: Which IRA Is Best for You? Roth vs Traditional Explained Simply
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 pl...
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Season 4
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Episode 108
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36:05
107: Avoid Money Drama: How Early Should Finances Come Up in Dating
In this episode, Jessica and Brandon dive into a tricky but essential question: How soon should you bring up money when you're dating?They unpack why money often feels taboo, share tips to start the conversation without tension, a...
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Season 4
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Episode 107
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31:00
106: Your Six Month Money Makeover
What If You Could Completely Transform Your Finances in Just 180 Days?Forget overnight success stories and overwhelming budgets, this episode is about real, lasting change. Jess and Brandon are breaking down a six-month financ...
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Season 4
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Episode 106
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34:52
105: Investing Made Simple with Chloé Daniels
Feel like investing is only for finance bros and math nerds? You’re not alone and this episode is about to change that.This week, Jess and Brandon are joined by Chloé Daniels, the powerhouse behind Clo Bare Money, who’s helped ove...
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Season 4
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Episode 105
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1:01:12
104: No More GoFundMe Funerals | The Life Insurance Talk You Can’t Afford to Skip
GoFundMe should never be your family’s financial plan.In this episode Jess & Brandon break down why life insurance is a non-negotiable part of smart financial planning, no matter your age, income, or relationship status.
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Season 4
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Episode 104
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27:05
103: Stay-at-Home Parenting: The Privileges and Financial Risks
For many families, the decision to become a stay-at-home parent isn’t really a choice, it’s the result of America’s broken childcare system. Daycare costs can swallow an entire paycheck, but leaving the workforce carries hidden financial risks ...
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Season 4
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Episode 103
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31:09
102: Empowering Women with Money: Bola Sokunbi of Clever Girl Finance
What does true financial freedom look like for women?Bola Sokunbi, founder of Clever Girl Finance, shares her journey from witnessing women in crisis—arriving at her family’s doorstep with nothing but suitcases, to buildi...
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Season 4
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Episode 102
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1:02:27
101: Rip & Rant | The Truth About Taxes, Corporate Greed & Crypto in your 401(k)
In this episode, Jess and Brandon tackle the misconception of taxes, corporate greed and the new twist in retirement planning: cryptocurrency in your 401(k).The path to financial security lies in addressing the real economic challenges: ...
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Season 4
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Episode 100
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21:27
100: The One Number That Determines Your Financial Future
Your income and investment returns matter—but nothing predicts your financial freedom more than your savings rate. Yet, most Americans save only 3–5% of their income, a level that almost guarantees they’ll have to work far longer than th...
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Season 4
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Episode 100
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24:42
99: Follow the Money in Your Marriage with Forensic Accountant Tracy Coenen
Money secrets can wreck marriages—and cost you everything in divorce. In this episode, Forensic Accountant, Tracy Coenen, reveals how spouses hide assets (think offshore accounts, hidden income, even billionaires fighting over private jets) and...
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Season 4
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Episode 99
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46:10
98: Rip & Rant: Insider Trades, Tone-Deaf Tips & Financial Gaslighting
Ever wonder how politicians like Nancy Pelosi and Marjorie Taylor Greene grow millionaire-level wealth while you're getting hit with overdraft fees? In this episode, Jess and Brandon expose the shady world of insider stock trades, slap-on-the-w...
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Season 4
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Episode 98
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35:52
97: How to Pick a Credit Card That Actually Works for You
Still swiping your debit card? You could be earning serious rewards instead. In this episode, Jessica and Brandon unpack how they use credit cards as intentional tools to build value—whether that’s free travel, cashback, or everyday perks that ...
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Season 4
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Episode 95
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20:15
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