107: Avoid Money Drama: How Early Should Finances Come Up in Dating

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 plan.Learn how taxes, income levels, and long-term growth factor into the decision, and why the right choice could save you thousands down the road.We cover: – How Roth and Traditional IRAs actually work – Which one fits different income brackets – Tax implications now vs later – Real-life scenarios to help you decide – Common myths and costly mistakesWhether you're just getting started or rethinking your retirement strategy, this episode gives you the clarity to move forward with confidence.Head over to our YouTube channel to catch this episode in full video form.Apply to be a guest on the show.You can also email us at: [email protected] with us on InstagramWe’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 Jess, The Sugar Daddy Podcast breaks down how to build wealth, unpack old money beliefs, and have real conversations about love and finances. Our mission? To help couples and individuals grow rich in every sense of the word: emotionally, relationally and financially.

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, and explore real‐life stories about financial expectations, backgrounds, and values. Whether you're in your 20s, 30s, or beyond, you’ll get tools to help you be curious, open, and intentional in your relationships.What You’ll Learn:How early is “too early” vs. “too late” to talk about things like debt, financial goals, and spending styles.Simple conversation starters that don’t feel intimidating.How upbringing & past financial habits influence what you expect (and need) in a partner.What to do if your partner resists having the money talk.Questions we answer:Should you ask about money on date one, date two, or after you get more serious?What clues about a person’s financial mindset can you pick up in subtle ways?When is it okay to split bills 50/50 vs. proportionally?If you’ve navigated this conversation well, or struggled badly, share your stories with us! We love hearing what works (and what doesn’t) in real life.        Head over to our YouTube channel to catch this episode in full video form.Apply to be a guest on the show.You can also email us at: [email protected] with us on InstagramWe’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 Jess, The Sugar Daddy Podcast breaks down how to build wealth, unpack old money beliefs, and have real conversations about love and finances. Our mission? To help couples and individuals grow rich in every sense of the word: emotionally, relationally and financially.

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 financial reset plan that shows you exactly how to take control of your money, no matter where you're starting. They’ll walk you through:The first step everyone skips (but shouldn't): Getting crystal clear on where your money is goingThe tools that simplify your entire money flow (yes, we’re talking Monarch Money)How to build an emergency fund without feeling brokeDebt payoff strategies that actually match your personality (Snowball vs Avalanche)How automation becomes your secret weaponAnd why small, consistent wins are the key to long-term wealthIf your bank account isn’t reflecting the life you want, this episode gives you the roadmap to change that. In just six months, you can go from overwhelmed and disorganized to confident and in control.Hit play and learn the exact steps to finally reset your finances, for good.Watch the video version on YouTube:  http://www.youtube.com/@TheSugarDaddyPodcast                                     Head over to our channel to catch this episode in full video form.Apply to be a guest on the show!: https://www.thesugardaddypodcast.com/guests/intake/You can also email us at: [email protected] with us on Instagram We’re most active over at @thesugardaddypodcast: https://www.instagram.com/thesugardaddypodcastChat with Brandon Want to work together? Learn more about Brandon: https://www.oakcityfinancial.us/ Book a free 30-min call to see if it's a fit:  https://calendly.com/oakcityfinancial/introconvoShow us some love, hit subscribe, leave a five star rating, and drop a quick review!Notes from the show:Monarch MoneyAlly BankBankrate Credit Card Payoff CalculatorMoney, relationships, and the mindset to master both. Hosted by financial advisor Brandon and his wife Jess, The Sugar Daddy Podcast breaks down how to build wealth, unpack old money beliefs, and have real conversations about love and finances. Our mission? To help couples and individuals grow rich in every sense of the word: emotionally, relationally and financially.

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 over 300,000 people ditch financial fear and start investing the lazy way. Chloe’s journey is all-too-relatable: from believing “girls are bad with money” to loaning a now ex $50K, she’s made the mistakes so you don’t have to.She breaks down investing in a way that actually makes sense—no jargon, no shame. You’ll learn how to: • Automate your investments with zero stress • Use tools like robo-advisors or target date funds • Stop overcomplicating wealth-building (seriously, it’s easier than you think) • Rewire old money beliefs holding you backPlus, Chloé gets real about prenups, financial red flags in relationships, and why loving someone doesn’t mean going broke for them.If you’ve ever thought, “I want to invest but have no idea where to start,” this is your starting line. Hit play and get ready to feel empowered, not overwhelmed.Watch this episode in video form on YouTubeTo apply to be a guest on the showYou can email us at: [email protected] sure to connect with us on socials @thesugardaddypodcast we are most active on InstagramLearn more about Brandon and schedule a free 30-minute introductory call with him Please remember to subscribe, rate, and review.Notes from the show:Clo Bare Money CoachEnroll in The Lazy Investor's CourseFollow Clo Bare Money Coach on TikTokFollow Clo Bare Money Coach on InstagramFollow Chloé Daniels on XSubscribe on YouTubeFollow Chloe on LinkedInBook your free 30 min prenup consult with Prenups.comMoney, relationships, and the mindset to master both. Hosted by financial advisor Brandon and his wife Jess, The Sugar Daddy Podcast breaks down how to build wealth, unpack old money beliefs, and have real conversations about love and finances. Our mission? To help couples and individuals grow rich in every sense of the word: emotionally, relationally and financially.

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.They share a powerful, heartbreaking story of a brilliant friend who passed away at 38, leaving behind a wife and young child with no coverage, and no financial protection. It’s a harsh wake-up call and a reminder that life can change in an instant.Here’s what you’ll learn:Why everyone needs life insurance, even if you're single or child-freeWhy employer-provided coverage is usually not enoughHow your health and age impact coverage cost (and why timing matters)How to set up beneficiaries correctly for estate planningWhy life insurance isn’t about fear, it’s about love and legacyThis episode isn’t just informative, it’s personal. Whether you're building wealth or just starting your financial journey, this conversation could be the most important one you hear all year.Watch this episode in video form on YouTubeTo apply to be a guest on the showYou can email us at: [email protected] sure to connect with us on socials @thesugardaddypodcast we are most active on InstagramLearn more about Brandon and schedule a free 30-minute introductory call with him Please remember to subscribe, rate, and review.Notes from the show:Episode 59: Wills & Trusts: Essential Estate Planning Tips from Attorney, Nicola Rochester RobinsonEpisode 7: Protection Planning: Why You Need Life and Disability InsuranceMoney, relationships, and the mindset to master both. Hosted by financial advisor Brandon and his wife Jess, The Sugar Daddy Podcast breaks down how to build wealth, unpack old money beliefs, and have real conversations about love and finances. Our mission? To help couples and individuals grow rich in every sense of the word: emotionally, relationally and financially.

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 that can last for decades.In this episode, Jess & Brandon explore:How career gaps impact your resume and earning powerWhy retirement savings and Social Security shrink when you’re out of the workforceThe power imbalances that can emerge in single-income householdsWhy divorce hits stay-at-home parents especially hardStrategies to safeguard your financial future, from spousal IRAs to postnuptial agreementsIf you’re weighing the decision to stay home, or are already living it, this honest conversation will help you navigate the intersection of parenting, money, and identity.Watch this episode in video form on YouTubeTo apply to be a guest on the showYou can email us at: [email protected] sure to connect with us on socials @thesugardaddypodcast we are most active on InstagramLearn more about Brandon and schedule a free 30-minute introductory call with him Please remember to subscribe, rate, and review.Money, relationships, and the mindset to master both. Hosted by financial advisor Brandon and his wife Jess, The Sugar Daddy Podcast breaks down how to build wealth, unpack old money beliefs, and have real conversations about love and finances. Our mission? To help couples and individuals grow rich in every sense of the word: emotionally, relationally and financially.

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 building one of the largest personal finance platforms for women in the U.S.Raised in Nigeria, Bola absorbed early money lessons from her parents and watched her mother’s determination change the trajectory of their family. After being dismissed by a financial advisor who questioned her success, she set out to educate herself and ultimately millions of women about money.In this conversation, Bola opens up about financial independence, cultural pressures, and finding her voice in male-dominated spaces. Her message is clear: financial security isn’t just about money,it’s about options, freedom, and the power to walk away when life demands it.Ready to create more choices in your own life? Bola shares practical steps to get started today.Watch this episode in video form on YouTubeTo apply to be a guest on the showYou can email us at: [email protected] sure to connect with us on socials @thesugardaddypodcast we are most active on InstagramLearn more about Brandon and schedule a free 30-minute introductory call with him Please remember to subscribe, rate, and review.Notes from the show:Clever Girl FinanceClever Girls Know! PodcastFollow Clever Girl Finance on TikTokFollow Clever Girl Finance and Bola on Instagram Subscribe on YouTube Follow Bola on LinkedInMoney, relationships, and the mindset to master both. Hosted by financial advisor Brandon and his wife Jess, The Sugar Daddy Podcast breaks down how to build wealth, unpack old money beliefs, and have real conversations about love and finances. Our mission? To help couples and individuals grow rich in every sense of the word: emotionally, relationally and financially.

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: demanding fair compensation, understanding the true value of your work, and sticking with sound, proven financial principles. If you want to stop falling behind and start building real financial security, this episode is your wake-up call.Watch this episode in video form on YouTubeTo apply to be a guest on the showYou can email us at: [email protected] sure to connect with us on socials @thesugardaddypodcast we are most active on InstagramLearn more about Brandon and schedule a free 30-minute introductory call with him Please remember to subscribe, rate, and review.Money, relationships, and the mindset to master both. Hosted by financial advisor Brandon and his wife Jess, The Sugar Daddy Podcast breaks down how to build wealth, unpack old money beliefs, and have real conversations about love and finances. Our mission? To help couples and individuals grow rich in every sense of the word: emotionally, relationally and financially.

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 they’d like.In this episode, Jess & Brandon reveal why your savings rate is the true driver of wealth and how it works regardless of income level. They share real examples of modest earners who retired as millionaires—and why high-income professionals often fall behind due to lifestyle inflation.You’ll discover:How to calculate your personal savings rateThe percentage you need to hit for retirement security and early financial independencePractical steps to increase your savings without feeling restrictedHow to set up automation so you save consistently and effortlesslyThey’ll also challenge you with a simple, two-step plan to make saving non-negotiable and start shaping the future you actually want.Watch this episode in video form on YouTubeTo apply to be a guest on the showYou can email us at: [email protected] sure to connect with us on socials @thesugardaddypodcast we are most active on InstagramLearn more about Brandon and schedule a free 30-minute introductory call with him Please remember to subscribe, rate, and review.Money, relationships, and the mindset to master both. Hosted by financial advisor Brandon and his wife Jess, The Sugar Daddy Podcast breaks down how to build wealth, unpack old money beliefs, and have real conversations about love and finances. Our mission? To help couples and individuals grow rich in every sense of the word: emotionally, relationally and financially.

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 how she uncovers the truth.Tracy’s 25+ year career as a forensic accountant gives her a unique lens into corporate fraud, white-collar crime, and high-stakes divorce battles. In this episode she shares:How to spot signs your partner might be hiding moneySteps to protect yourself and your moneyHow to have open, non-defensive money conversations in a healthy marriageEven if you’re not headed for divorce, Tracy explains why financial transparency and independence are essential safeguards for every relationship.Listen now to learn how to protect your finances, your future, and your peace of mind.Watch this episode in video form on YouTubeTo apply to be a guest on the showYou can email us at: [email protected] sure to connect with us on socials @thesugardaddypodcast we are most active on InstagramLearn more about Brandon and schedule a free 30-minute introductory call with him Please remember to subscribe, rate, and review.Notes from the show:Divorce Money Guide Divorce Money Guide Podcast Follow Tracy on TikTokFollow Tracy on Instagram Subscribe on YouTube Follow Tracy on LinkedInMoney, relationships, and the mindset to master both. Hosted by financial advisor Brandon and his wife Jess, The Sugar Daddy Podcast breaks down how to build wealth, unpack old money beliefs, and have real conversations about love and finances. Our mission? To help couples and individuals grow rich in every sense of the word: emotionally, relationally and financially.