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
147 episodes
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...
132: Why Debt Hits Harder After 35 (And What To Do About It)
Debt in your 20s felt manageable. Now it's competing with your mortgage, your kids, your aging parents, and your retirement clock and it's winning. In this episode, Jessica and Brandon unpack why debt feels so much heavier in your l...
131: Pack Extra Underwear And Get A Postnup
Your spouse just found out they're inheriting money, and now they want a postnup. Do you panic, or do you see it for what it actually is?In this episode, Jessica and Brandon break down the real purpose of prenups and postnups, share why ...
130: Trump Accounts Explained: What Every Parent Needs to Know Before They Open One
Trump Accounts are making headlines, but do they actually benefit your child, or are they just political noise? In this episode, Jessica and Brandon break down everything you need to know about the proposed Trump Accounts: who qualifies, how th...
129: Why You Should Stop Using Your Debit Card
If you’re using a debit card for everyday spending, this episode is a must-listen.Jessica and Brandon break down a real-life fraud situation and explain why the outcome would have been very different if a debit card had been used instead...
128: The 1 RSVP Mistake Parents Make That Costs Birthday Hosts Hundreds
A simple birthday party question turned into a bigger conversation about boundaries, assumptions, and modern parenting etiquette.What should you do when parents RSVP kids who weren’t invited?In this episode, Jessica and Brandon ta...
127: The Life Insurance Mistake Almost Everyone Makes
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 tr...
126: How to Build an Emergency Fund That Actually Protects Your Family
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 c...
125: What to Do With Your Tax Refund (Before You Waste It)
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 governm...
124: Price vs Value: Why Cheap Decisions Cost You More
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 unders...
123: Buying a Home Is Almost Impossible Now (And It’s Not Your Fault)
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...
122: Mutual Funds vs ETFs vs Stocks: What You Need to Know Before Investing
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 h...
121: Would You Give $100K to Your Ex’s New Family?
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...
120: Monarch Money: The Easiest Way to Manage Your Money as a Couple
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 disc...
119: 4 Money Seasons Most People Misunderstand (And Pay For Later)
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
118: Start 2026 Broke or Building? 5 Must-Do Money Moves
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 payof...
117: The 2025 Financial Audit You Can’t Afford to Skip (Before It’s Too Late)
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 feel...
116: Five Signs You Need Financial Therapy
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 o...
115: Five Money Mistakes That Break Couples and How to Avoid Them
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… a...
114: Why Most Women Are Financially Blind and How to Fix It
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 dang...
113: $50K Teacher Salary to 800+ Rental Units: How He Did It
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 ...
112: Broke, Divorced & a $1,200 Stimulus Check — to Multi‑Million Dollar Business
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 for...
111: Most People Blow Inheritance Money — Here’s the 5-Step Fix
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 lifestyl...
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...