The Sugar Daddy Podcast

Hosted by The Sugar Daddy Podcast

Business Investing Education

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Episodes

172

Latest episode

Oct 2026

Language

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.

Listen to episodes

60 recent

October 21, 2026Episode 15427 min

154: Holiday Magic on a Budget: How to Celebrate Without the January Debt Hangover

Send us Fan Mail Why does December wreck the budget every year, even when you swore this year would be different? Jessica and Brandon unpack the guilt, tradition, and social pressure that push millions of families into holiday debt, and share how they rebuilt their own celebrations around time instead of stuff. You'll hear the Christmas morning moment that changed their approach to gifts and the simple traditions their kids now beg for months ahead. In this episode: When to actually start saving for the holidays Why adult gift swaps are just trading money Experience gifts and gifts that teach Free traditions kids remember How to tell family you're spending less 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...

October 14, 2026Episode 15329 min

153: Backdoor Roth, Mega Backdoor & Roth Conversions Explained

Send us Fan Mail Googled "backdoor Roth" late at night and closed the tab more confused than when you started? This one's for you. Jessica and Brandon go one step past the basic Roth IRA to unpack the backdoor Roth, the mega backdoor Roth, and Roth conversions. Jessica asks the questions you're already thinking (including why the IRS makes this so complicated), and Brandon explains the one rule social media almost never mentions, plus the move he uses with clients to get around it. In this episode: Who can't contribute to a Roth IRA directly, and what to do instead The backdoor Roth, step by step The pro rata rule and how to avoid a surprise tax bill The mega backdoor Roth and the two plan features you need Roth conversions: brackets, timing, and who pays the tax The five year rule on converted dollars EPISODE CORRECTIONS: Pro rata rule: a one time tax bill, NOT ongoing penalties. Ongoing penalty: 6% per year for over contributing to an IRA, until you remove the excess. RMDs now start at 73, or 75 if you were born in 1960 or later. Roth IRAs have no RMDs. 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...

October 7, 2026Episode 15228 min

152: Informed vs. Intentional: 3 Steps to Finally Act on Your Money

Send us Fan Mail 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 informed and being intentional. They dig into the information trap that makes research feel like progress, the myths that keep smart people stuck on the sidelines, and the simple framework they use to turn knowledge into moves that show up in your accounts. In this episode: • Why consuming money content can feel productive without moving the needle • The real cost of spending three weeks picking a savings account • Why "I'll plan when I make more" gets it backwards • What every spouse should know, even if the other one runs the money • The 3 Ds of intentional money management Pick one thing. Do it this week. Then tell Jessica and Brandon about it at! 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...

September 30, 2026Episode 15126 min

151: We Got an Email From a 21 Year Old Doing Money Better Than Most

Send us Fan Mail 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 she's stuck on what comes next. Jessica and Brandon walk through her numbers, give their honest take, and then zoom out to what every young adult should be doing to get ahead. In this episode: • Roth IRA now, or wait for a 401k? • Paying off student loans vs investing • The overlooked risk that can erase years of saving • Why your parents' money advice may not fit your life • A free finance book offer for listeners under 30 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...

September 23, 202643 min

REWIND: 5 Open Enrollment Mistakes That Lock You In for a Year

Send us Fan Mail 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 the process still works. After watching their own premiums jump 17%, Jessica and Brandon open up their family's open enrollment process. Brandon shares the first thing he checks before comparing any plan, why the most expensive option often isn't the smartest one, and what a surgeon's disability policy taught him about being underinsured. Plus, a real time discovery about their own coverage that caught Brandon completely off guard. In this episode: • Why last year's plan isn't a safe default • The one number to know before you choose • When a pricier plan is worth it • Disability insurance and the 60% gap • HSA, FSA, and dependent care FSA basics • Perks most people never use 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...

September 16, 2026Episode 15041 min

150: The Trad Wife Trap Nobody Warns You About

Send us Fan Mail 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 before giving up a paycheck. They cover why the influencers selling this life are quietly millionaires, what divorce really costs the non-earning partner, and the money rules that keep you from being left with nothing. In this episode: • Prenups, postnups, and the response that is a red flag • Building credit and holding assets in your own name • The spousal IRA a non-working partner can still fund • Life and disability insurance that go both ways • Full financial visibility at home • The 10 year Social Security rule most people miss Choose the life you want, just build a floor underneath it first. New episodes every Wednesday. Talk with our postnup attorney, Aaron Thomas. 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...

September 9, 2026Episode 14921 min

149: Emergency Fund Before Investing: Your First Financial Step

Send us Fan Mail 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 investing, and the one exception. They cover how much you actually need, where to keep it so inflation does not erode it, and why both a checking account and a brokerage account are the wrong home for it. They also share their own numbers, including the figure Jessica wanted after years in a volatile tech industry. In this episode: Why the emergency fund comes before investing How much to save for your situation The 5 year rule for saving versus investing Where to keep it, and where not to The one exception for employer retirement matches New episodes every Wednesday. Follow the show and share it with a friend. 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...

September 2, 2026Episode 14840 min

148: 5 Money Rules That Save You After Divorce

Send us Fan Mail 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: the one paying, the one receiving, and the spouse who walks away with almost nothing. They get into the parts nobody warns you about: how retirement accounts get split, why alimony no longer works in your favor at tax time, the credit hit from closing joint accounts, and the Social Security benefit you may be owed from an ex. Plus the 5 rules for getting back on solid ground. Whether divorce is on your radar, in progress, or years behind you, this is the playbook that protects what you built. New episodes every Wednesday. Follow so you never miss one. Show Notes: Interested in getting a prenup or postnup? Contact Aaron Thomas 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...

August 26, 2026Episode 14729 min

147: Do You Actually Know What It Costs to Be You? Build a Budget That Finally Sticks

Send us Fan Mail 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 and budgeting so you can finally see where your money goes and give every dollar a job. 👉🏽 The one number that drives every other money decision you make 👉🏽 The perception gap: why you're spending more than you think, and where it hides 👉🏽 The 3 bucket method: fixed, variable, and the periodic expenses that wreck most budgets 👉🏽 How to read your cash flow at a glance with Monarch Money 👉🏽 Pay yourself first, then automate everything so you never have to think about it 👉🏽 High-yield savings buckets that make saving actually doable 👉🏽 Why budgeting is not restriction, it is permission to live the life you want We also love Ally for high-yield savings buckets: https://www.ally.com/referral?code=4R3J2Q3N3K New episodes every Wednesday. Subscribe so you never miss one. 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...

August 19, 2026Episode 14651 min

146: How ADHD is Draining Your Bank Account

Send us Fan Mail 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 talks about: ADHD and money. They break down why executive function makes bills, budgets, and impulse control genuinely harder, and why the standard "just be more disciplined" advice sets neurodivergent brains up to fail. Jessica and Brandon also get into how ADHD shows up differently in men and women, the money patterns that quietly do the most damage (bill blindness even when the money is there, impulse spirals, feast-or-famine spending, analysis paralysis), and six systems you can build to work with your brain instead of against it, from automating everything to designing an environment that removes temptation before it starts. You are not broken. You are not alone. And there is a plan that fits how your brain actually works. New episodes every Wednesday. 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...

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