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The Sugar Daddy Podcast

The Sugar Daddy Podcast

By: 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.

© 2026 The Sugar Daddy Podcast
Economics Leadership Management & Leadership Personal Finance
Episodes
  • 140: College Funds, Ultimatums, and $13K Monthly Bills: Social Media Posts That Got Us Talking
    Jun 10 2026

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    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 who demanded $10,000 from his wife's daughter's medical school fund to buy a truck, and threatened divorce when she said no. Then: a grieving father who wants to give his late daughter's college fund to her best friend instead of a blood relative, dividing the comments. And finally: a gut-punch of an article about families moving aging parents to Mexico because $13,000-a-month memory care facilities in the US are financially impossible for most people.

    Topics covered in this episode:
    • Why financial entitlement is one of the loudest red flags in a relationship
    • How to protect dedicated savings in blended families (prenups, post-nups, separate accounts)
    • When it's your money, it's your call, the limits of family obligation
    • The long-term care crisis quietly threatening the retirement plans of sandwich-generation millennials
    • Why most people have no idea what their parents' finances actually look like, and what that costs them
    • Long-term care policies: who needs them, when to get them, and why waiting is the most expensive mistake

    If you've been avoiding the money conversation with your aging parents, this episode is the sign to stop waiting.

    Get a $5 month for Point.Me our favorite way to find the best flights

    Get 50% off of Monarch Money for one year with this link

    Subscribe to The Sugar Daddy Podcast newsletter

    Explore The Sugar Daddy Podcast Stan Store — Downloadables, tools, and more to level up your money game together!

    Head over to our YouTube channel to catch this episode in full video form.

    You can also email us at: hello@thesugardaddypodcast.com

    Connect with us on Instagram
    We’re most active over at @thesugardaddypodcast

    Chat with Brandon
    Want to work together? Learn more about Brandon

    Book a free 30-min call to see if it's a fit.

    Show us some love, hit subscribe, leave a five star rating, and drop a quick review!

    Money, relationships, and the mindset to master both. Hosted by financial advisor Brandon and his wife Jessica, The Sugar Daddy Podcast breaks down how to build wealth, unpack old money beliefs, and have real conversations...

    Show More Show Less
    28 mins
  • 139: We're Skipping Summer Camp and Spending a Month in Europe Instead
    Jun 3 2026

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    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 stalking flight portals for months to find 120,000 points worth of flights across four countries, to building a five-tab spreadsheet to keep every confirmation number, address, and ticket organized, this episode is the full behind-the-scenes of planning an international family trip.

    They cover the tools they actually use: Point.me for finding the best points and miles deals, Airbnbs with washers, dryers, and AC over hotels, bulk public transit passes, and the free Smart Traveler Enrollment Program that sends real-time safety alerts from the nearest US embassy. They also get into the stuff that catches travelers off guard, like booking major attraction tickets weeks in advance before they sell out, spotting scam sites that mimic official museum pages, ordering foreign currency from your home bank before you leave, and knowing which credit cards to carry internationally and why.

    If you are planning a big international trip and want to know how to actually prepare for it, this one is worth a listen.

    Get a $5 month for Point.Me our favorite way to find the best flights

    Get 50% off of Monarch Money for one year with this link

    Subscribe to The Sugar Daddy Podcast newsletter

    Explore The Sugar Daddy Podcast Stan Store — Downloadables, tools, and more to level up your money game together!

    Head over to our YouTube channel to catch this episode in full video form.

    You can also email us at: hello@thesugardaddypodcast.com

    Connect with us on Instagram
    We’re most active over at @thesugardaddypodcast

    Chat with Brandon
    Want to work together? Learn more about Brandon

    Book a free 30-min call to see if it's a fit.

    Show us some love, hit subscribe, leave a five star rating, and drop a quick review!

    Money, relationships, and the mindset to master both. Hosted by financial advisor Brandon and his wife Jessica, The Sugar Daddy Podcast breaks down how to build wealth, unpack old money beliefs, and have real conversations...

    Show More Show Less
    40 mins
  • 138: The 20% Raise You're Not Getting by Staying at Your Job
    May 27 2026

    Send us Fan Mail

    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 and Brandon get real about the job hopping vs. loyalty debate. They share firsthand experience navigating layoffs, negotiate their way through six-figure compensation packages, and break down the framework listeners can use to make career decisions that actually build wealth.

    Topics covered:

    • Why piddly 1.5–3% annual raises are costing you serious long-term wealth
    • How to use competing offers to negotiate with your current employer without quitting
    • The right and wrong reasons to make a lateral move
    • Vesting schedules, RSUs, and benefits you should never leave on the table
    • The 15–20% rule: the number that makes a job switch worth the disruption
    • Why interviewing is a skill you must keep sharp — even when you're happy
    • How to build a network that works for you before you need it
    • What a client negotiated by simply asking ($30K base increase + doubled equity)
    • Beyond salary: education stipends, PTO, remote work, fertility benefits, and more

    Closed mouths don't get fed. This episode gives you the tools to start asking.

    Get a $5 month for Point.Me our favorite way to find the best flights

    Get 50% off of Monarch Money for one year with this link

    Subscribe to The Sugar Daddy Podcast newsletter

    Explore The Sugar Daddy Podcast Stan Store — Downloadables, tools, and more to level up your money game together!

    Head over to our YouTube channel to catch this episode in full video form.

    You can also email us at: hello@thesugardaddypodcast.com

    Connect with us on Instagram
    We’re most active over at @thesugardaddypodcast

    Chat with Brandon
    Want to work together? Learn more about Brandon

    Book a free 30-min call to see if it's a fit.

    Show us some love, hit subscribe, leave a five star rating, and drop a quick review!

    Money, relationships, and the mindset to master both. Hosted by financial advisor Brandon and his wife Jessica, The Sugar Daddy Podcast breaks down how to build wealth, unpack old money beliefs, and have real conversations...

    Show More Show Less
    37 mins
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