The Sugar Daddy Podcast
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.
Episodes
170 episodes
152: Informed vs. Intentional: 3 Steps to Finally Act on Your Money
How many money podcasts, books, and reels have you consumed this year? Now the harder question: how many of them actually changed what happens to your money on the first of the month?Jessica and Brandon unpack the gap between being info...
151: We Got an Email From a 21 Year Old Doing Money Better Than Most
Should you start investing if your job doesn't offer a 401k, or wait until life feels more stable?A 21 year old listener who graduated college at 19 wrote in with that exact question. On paper she's doing almost everything right, yet sh...
REWIND: 5 Open Enrollment Mistakes That Lock You In for a Year
You get a couple of weeks to make a decision you're stuck with for 12 months. So how do you know you're actually picking the right plan?Rewind: This episode originally aired in fall 2025. Plan details and limits change every year, but t...
150: The Trad Wife Trap Nobody Warns You About
The trad wife life looks lovely online. But what happens when the fantasy fizzles and you have no income, no credit, and no way out?Jessica and Brandon dig into the trad wife trend and the protections every stay at home spouse needs bef...
149: Emergency Fund Before Investing: Your First Financial Step
Everyone online talks about investing. Almost no one talks about the account that makes investing possible: the emergency fund.In this "back to basics" episode, Jessica and Brandon explain why a funded emergency fund comes before invest...
148: 5 Money Rules That Save You After Divorce
What happens to your money when a marriage ends? Divorce doesn't just end a marriage, it ends a financial plan, and most people have no idea what to do next.Jessica and Brandon break down rebuilding after divorce for all three sides: th...
147: Do You Actually Know What It Costs to Be You? Build a Budget That Finally Sticks
Before you can invest, pay off debt, buy the house, or book the trip, you need to know one number: what it actually costs to be you every month. Most people have a vibe, not a number. This week Jessica and Brandon go back to basics on cash flow...
146: How ADHD is Draining Your Bank Account
What if you were never "bad with money" at all? What if your brain is simply wired in a way that makes budgeting feel like swimming upstream?In this episode, Jessica and Brandon dig into the connection almost nobody in personal finance ...
145: We Took the Kids to Europe Instead of Summer Camp. Part 5 of 5: Nürnberg, Germany
What does it actually cost to take a family of four across four countries for a month in Europe? In the finale of their five part European series, Jessica and Brandon share the full breakdown and what a month abroad really added up to.T...
144: We Took the Kids to Europe Instead of Summer Camp. Part 4 of 5: Amsterdam
What does three nights in Amsterdam cost a family of four, and could you actually see yourself living there?In part four of their month in Europe, Jessica and Brandon skip the crowded city center for a storybook town twenty minutes out,...
143: We Took the Kids to Europe Instead of Summer Camp. Part 3 of 5: Disney Land Paris
Is Disneyland Paris worth it, or is it the one part of your Europe trip you can skip without regret?In Part 3 of the Europe travel series, Jessica and Brandon surprise their kids with three nights on property and reach a very honest ver...
142: We Took the Kids to Europe Instead of Summer Camp. Part 2 of 5: Paris
Is Paris actually worth the hype, or is it as rude, dirty, and overpriced as everyone warned? Jess and Brandon went to find out as a family of four, This is Part 2 of their five part series on a month in Europe, and it might be their favo...
141: We Took the Kids to Europe Instead of Summer Camp. Part 1 of 5: Barcelona
Four countries. Four weeks. A family of four, plus Brandon's mom. And it started because we didn't want to pay for six weeks of summer camp.This is Part 1 of a five-part series breaking down Jessica and Brandon's month in Europ...
SUMMER REWIND: He Gave His Brother $175K And Got Served A $310K Lawsuit
Summer Rewind: we are re releasing one of our most unforgettable listener stories while we travel through Europe, and this one still stops people in their tracks.In 2005, guest Ben took out $175,000 in private student loans that never p...
SUMMER REWIND: Why You Should Consider a Post-Nuptial Agreement
Summer Rewind: Brandon and Jessica are in Europe for the month. This one is worth revisiting.When you get married, your state automatically writes a financial agreement for you. Most couples have no idea. That reframe is what led Brando...
SUMMER REWIND: When Should You File for Bankruptcy?
Brandon and Jessica are traveling through Europe this month, so they're bringing back one of their most impactful episodes as part of their Summer Rewind series.Bankruptcy attorney Adrienne Hines joins the show to reframe everything most...
SUMMER REWIND: Five Money Moves to Kickstart Your Year
☀️ Summer Rewind! We're spending the month traveling Europe, so we're bringing back one of our most-listened-to episodes. The advice is fully evergreen and hits just as hard now as it did when it first dropped.If you've been meaning to g...
140: College Funds, Ultimatums, and $13K Monthly Bills: Social Media Posts That Got Us Talking
What happens when the internet gets honest about money, and people start showing their whole hand?This week's episode explores three viral social media posts as a jumping-off point for some real financial conversations. First: a husband...
139: We're Skipping Summer Camp and Spending a Month in Europe Instead
What if instead of summer camp, you just took your family to Europe for a month?Jessica and Brandon are taking their family to Europe for four weeks this summer, and in this episode they walk through exactly how they pulled it off. From ...
138: The 20% Raise You're Not Getting by Staying at Your Job
The data is clear: staying loyal to one employer rarely keeps pace with what strategic career moves can do for your income. But what does "smart" job hopping actually look like, and when does loyalty still win?In this episode, Jessica a...
137: My Mom Gifted Me a $400K Property and Won't Include My Boyfriend. Am I the A-hole?
A woman on Threads wrote that she is being gifted a $400,000 rental property by her mother, but only in her name, with a legal agreement keeping it separate from any future marriage. Her boyfriend of three years is furious. He wanted to sell it...
136: The Fight Behind the Fight: How Couples Argue About Money Without Saying It
You just had a fight about the dishwasher. Or the thermostat. Or the vacation your partner keeps putting off. Spoiler: it wasn't about any of those things.Most arguments couples have about money are actually about something much deeper,...
135: One Injury Away From Financial Ruin: Disability Insurance Explained
Your ability to earn money is your most valuable financial asset, and most people have zero protection for it.In this episode, Jessica and Brandon break down disability insurance from the ground up: what it actually covers, why your ...
134: Red Flags Your Job Is At Risk (And What To Do Now)
No performance issues. No warnings. Just a Monday morning calendar invite that ends your role. In this episode, Brandon and Jessica, a tech professional who has been laid off twice in two years, walk through the red flags most employees ignore,...
133: She Wanted $50K to Have His Baby. Was She Wrong?
A woman shows up to her partner with a 16-page binder, a proration schedule, and a request for up to $50,000 before agreeing to get pregnant. Her partner posts it to Reddit. The internet has thoughts. So do we.In this episode, Jessica an...