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
134 episodes
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...
•
Season 5
•
Episode 121
•
8:36
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...
•
Season 5
•
Episode 120
•
26:23
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
•
Season 5
•
Episode 119
•
38:30
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...
•
Season 5
•
Episode 118
•
27:26
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...
•
Season 4
•
Episode 117
•
42:00
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...
•
Season 4
•
Episode 116
•
49:32
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...
•
Season 4
•
Episode 115
•
52:43
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...
•
Season 4
•
Episode 114
•
29:52
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 ...
•
Season 4
•
Episode 113
•
51:17
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...
•
Season 4
•
Episode 112
•
50:35
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...
•
Season 4
•
Episode 111
•
29:16
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...
•
Season 4
•
Episode 110
•
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...
•
Season 4
•
Episode 109
•
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...
•
Season 4
•
Episode 108
•
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...
•
Season 4
•
Episode 107
•
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...
•
Season 4
•
Episode 106
•
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...
•
Season 4
•
Episode 105
•
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.
•
Season 4
•
Episode 104
•
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 ...
•
Season 4
•
Episode 103
•
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...
•
Season 4
•
Episode 102
•
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: ...
•
Season 4
•
Episode 100
•
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...
•
Season 4
•
Episode 100
•
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...
•
Season 4
•
Episode 99
•
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...
•
Season 4
•
Episode 98
•
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 ...
•
Season 4
•
Episode 95
•
20:15