The Sugar Daddy Podcast

Hosted by The Sugar Daddy Podcast

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Episodes

153

Latest episode

Jun 2026

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EN-US

About the show

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.

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60 recent

June 10, 2026Episode 14027 min

140: College Funds, Ultimatums, and $13K Monthly Bills: Social Media Posts That Got Us Talking

Send us Fan MailWhat 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 mistakeIf 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 flightsGet 50% off of Monarch Money for one year with this linkSubscribe to The Sugar Daddy Podcast newsletterExplore 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.comConnect with us on Instagram We’re most active over at @thesugardaddypodcastChat with BrandonWant to work together? Learn more about BrandonBook 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...

June 3, 2026Episode 13939 min

139: We're Skipping Summer Camp and Spending a Month in Europe Instead

Send us Fan MailWhat 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 flightsGet 50% off of Monarch Money for one year with this linkSubscribe to The Sugar Daddy Podcast newsletterExplore 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.comConnect with us on Instagram We’re most active over at @thesugardaddypodcastChat with BrandonWant to work together? Learn more about BrandonBook 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...

May 27, 2026Episode 13837 min

138: The 20% Raise You're Not Getting by Staying at Your Job

Send us Fan MailThe 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 wealthHow to use competing offers to negotiate with your current employer without quittingThe right and wrong reasons to make a lateral moveVesting schedules, RSUs, and benefits you should never leave on the tableThe 15–20% rule: the number that makes a job switch worth the disruptionWhy interviewing is a skill you must keep sharp — even when you're happyHow to build a network that works for you before you need itWhat a client negotiated by simply asking ($30K base increase + doubled equity)Beyond salary: education stipends, PTO, remote work, fertility benefits, and moreClosed 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 flightsGet 50% off of Monarch Money for one year with this linkSubscribe to The Sugar Daddy Podcast newsletterExplore 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.comConnect with us on Instagram We’re most active over at @thesugardaddypodcastChat with BrandonWant to work together? Learn more about BrandonBook 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...

May 20, 2026Episode 13716 min

137: My Mom Gifted Me a $400K Property and Won't Include My Boyfriend. Am I the A-hole?

Send us Fan MailA 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 and use the money toward a bigger place for them both. When she explained her mom's conditions, he packed a bag and moved in with a friend.In this episode, Jessica and Brandon break down why the mom's conditions are not just reasonable, they are smart. They also dig into what the boyfriend's reaction actually reveals about his character, why inheritance and asset protection are conversations every couple should be having, and what their own postnuptial agreement says about inherited wealth.Their verdict? Take the property. And seriously reconsider the relationship.Get a $5 month for Point.Me our favorite way to find the best flightsGet 50% off of Monarch Money for one year with this linkSubscribe to The Sugar Daddy Podcast newsletterExplore 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.comConnect with us on Instagram We’re most active over at @thesugardaddypodcastChat with BrandonWant to work together? Learn more about BrandonBook 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...

May 13, 2026Episode 13644 min

136: The Fight Behind the Fight: How Couples Argue About Money Without Saying It

Send us Fan MailYou 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, and once you learn to spot it, you can't unsee it.In this episode, Jessica and Brandon break down how couples argue about money without ever actually talking about money. They share their own real-life examples, including Jessica's recent "I want to save $100,000" moment (and what was really underneath it), the time Brandon left Jessica's stocking empty on Christmas, and how they finally got on the same page about paying for their kids' college.You'll also learn the DREAM framework, their 5-step approach to decoding what your money arguments are really about and having the conversations that actually fix them.What you'll learn:Why fights about Target runs, utility bills, and vacation planning are rarely about the moneyHow scarcity mindsets and childhood money memories show up in your relationship right nowThe exact phrase that helps you peel back what a money argument is really aboutWhen to pause mid-fight and how to schedule a money date that actually worksHow tools like Monarch Money can eliminate the visibility gaps that fuel conflictFree resource: Grab their Dream Money Conversations guideGet a $5 month for Point.Me our favorite way to find the best flightsGet 50% off of Monarch Money for one year with this linkSubscribe to The Sugar Daddy Podcast newsletterExplore 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.comConnect with us on Instagram We’re most active over at @thesugardaddypodcastChat with BrandonWant to work together? Learn more about BrandonBook 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...

May 6, 2026Episode 13540 min

135: One Injury Away From Financial Ruin: Disability Insurance Explained

Send us Fan MailYour 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 employer's policy probably isn't enough, and how to plug the gaps before something happens.You'll learn:The difference between short-term and long-term disability, and why most people confuse themWhy 60% of your base salary sounds fine until you do the mathThe critical policy feature that determines whether you can actually collect (own occupation vs. any occupation)How the underwriting process works, and why your medical records matter more than you thinkWhy disability insurance may be more important than life insuranceThe future increase rider that lets you grow your coverage without going through medical underwriting againIf you have income and people who depend on it, this episode is non-negotiable.🎙️ New episodes every Wednesday on Apple Podcasts, Spotify & YouTubeGet a $5 month for Point.Me our favorite way to find the best flightsGet 50% off of Monarch Money for one year with this linkSubscribe to The Sugar Daddy Podcast newsletterExplore 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.comConnect with us on Instagram We’re most active over at @thesugardaddypodcastChat with BrandonWant to work together? Learn more about BrandonBook 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...

April 29, 2026Episode 13451 min

134: Red Flags Your Job Is At Risk (And What To Do Now)

Send us Fan MailNo 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, what to do financially before a layoff happens, and how to navigate the first critical days after it does.Listeners will learn:How to spot the organizational and role-specific signs that a layoff may be comingWhy great performance reviews offer no protection How to size and build a properly funded emergency fund What to look for in a severance package before signing anything How to approach networking and resume maintenance year-round Why treating a layoff as a business decision, not a personal failure, is the first step toward getting back on your feetA practical, honest conversation for anyone who is currently employed, recently laid off, or simply paying attention to what is happening in the workforce right now.💰 Monarch Money (50% off)Get a $5 month for Point.Me our favorite way to find the best flightsGet 50% off of Monarch Money for one year with this linkSubscribe to The Sugar Daddy Podcast newsletterExplore 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.comConnect with us on Instagram We’re most active over at @thesugardaddypodcastChat with BrandonWant to work together? Learn more about BrandonBook 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...

April 22, 2026Episode 13326 min

133: She Wanted $50K to Have His Baby. Was She Wrong?

Send us Fan MailA 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 and Brandon break down a viral Reddit thread about financial compensation for pregnancy, and why this woman's "crazy" demand is actually one of the smartest financial moves an unmarried woman can make. They cover the motherhood tax, why spiritually married is just legally roommates, and the money conversations couples should be having before a baby ever enters the picture.If you're in a relationship and thinking about kids, this episode is required listening.Show Notes:Episode 93: Writing Our Own Rules: Details of our Post-Nuptial AgreementGet a $5 month for Point.Me our favorite way to find the best flightsGet 50% off of Monarch Money for one year with this linkSubscribe to The Sugar Daddy Podcast newsletterExplore 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.comConnect with us on Instagram We’re most active over at @thesugardaddypodcastChat with BrandonWant to work together? Learn more about BrandonBook 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...

April 15, 2026Episode 13232 min

132: Why Debt Hits Harder After 35 (And What To Do About It)

Send us Fan MailDebt 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 late 30s and 40s, why making more money didn't fix it, and what to actually do now. They discuss the “invest vs. pay off debt” debate, the identity shift you need before any strategy will stick, and the one action item that will bring immediate clarity. Real talk from two elder millennials who get it.🔗 Free 6-Month Money Makeover Guide💰 Monarch Money (50% off)Get a $5 month for Point.Me our favorite way to find the best flightsGet 50% off of Monarch Money for one year with this linkSubscribe to The Sugar Daddy Podcast newsletterExplore 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.comConnect with us on Instagram We’re most active over at @thesugardaddypodcastChat with BrandonWant to work together? Learn more about BrandonBook 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...

April 8, 2026Episode 13122 min

131: Pack Extra Underwear And Get A Postnup

Send us Fan MailYour 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 they got one after almost a decade of marriage, and explain why the stigma around these agreements is costing couples more than they realize. Spoiler: your state already wrote your prenup. You just don't know what it says.They cover what to actually include in a postnup (inheritance, kids' accounts, mortgages, debt), why you don't divorce the same person you married, and why building these protections while love is high is the smartest financial move a couple can make.Think of it as love insurance, you hope you never need it, but you'll be grateful it's there.Get a $5 month for Point.Me our favorite way to find the best flightsGet 50% off of Monarch Money for one year with this linkSubscribe to The Sugar Daddy Podcast newsletterExplore 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.comConnect with us on Instagram We’re most active over at @thesugardaddypodcastChat with BrandonWant to work together? Learn more about BrandonBook 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...