I Date Money: Own Your Money • Build Cash Flow • Multiply Wealth

Lisa Drennon

Multi-passionate female entrepreneurs who've built real income and assets but still feel scattered with money need the Money Multiplier System™ to organize cash flow, pay themselves consistently, and turn income into lasting wealth, not another budget. Welcome to iDateMoney®️ with Lisa Drennon, Wealth Activator, author, and founder of the iDateMoney® brand. If you're running multiple income streams, own assets, and work hard for your money but can't see where it's actually going or make confident financial decisions, this podcast is for you. Here, we skip the generic budgeting advice and dive into: ✓ The ABCs of Wealth framework (Activate • Build • Cash Flow) ✓ The Money Multiplier System™ for organizing personal money ✓ The Calm Cash Flow Strategy that pays you consistently ✓ Practical tools to eliminate hidden money leaks and build lasting wealth Each episode teaches you how to OWN Your Money with the confidence and clarity you deserve. Your money challenge isn't about earning more. It's about having a system you trust. Get ready to multiply your wealth; because it doesn't matter how much money you have-it's what you do with it.🗝️🌬️💖💰

  1. 4d ago

    Faith, Finances & Building a Business That Lasts with Elaine Lankford

    Save $500–$2,000 in hidden money leaks, organize your cash flow, and create a money system that actually works with the Money Hunt found inside the Smell of Money Community.  Join here: https://www.skool.com/the-smell-of-money/about What if the biggest thing holding your business back isn't your marketing, it's your relationship with money? In this episode of iDateMoney®, Lisa Drennon sits down with Christian business coach Elaine Lankford to explore the mindset shifts every woman entrepreneur needs to build a profitable business with confidence. Elaine shares her powerful journey from a successful nursing career that unexpectedly ended to rebuilding her life and business through faith, resilience, and strategic action. Together, Lisa and Elaine unpack the money beliefs that quietly keep women stuck and reveal practical ways to create both financial confidence and lasting wealth. If you've ever struggled with inconsistent income, shiny object syndrome, fear of investing in yourself, or wondering if you're truly equipped to succeed, this conversation is for you. In This Episode You'll Learn:Why separating your business and personal finances is one of the first steps toward financial confidence.The difference between having revenue and building real wealth.How scarcity thinking keeps entrepreneurs stuck—and how to replace it with an abundance mindset.Why every successful entrepreneur needs a written financial and business plan.How comparison and imposter syndrome quietly impact your income.The importance of surrounding yourself with mentors and people who think differently about money.Why taking calculated risks is necessary for growth.How to build confidence one consistent step at a time.A healthier perspective on retirement, wealth, and creating a life you truly enjoy.Why money is simply a tool—and how stewarding it well creates greater impact.Memorable Quotes"Money isn't the problem. It's what we believe about money that shapes the decisions we make." "Consistency builds confidence." "You don't need more information—you need a simple plan you can actually follow." "It doesn't matter how much money you have. It's what you do with it." Connect with Elaine LankfordWebsite: https://shestepsforwardcoaching.com Email: Elaine@shestepsforwardcoaching.com Ready to Organize Your Money?If you're making money but still wondering where it all goes, it's time to build a system that gives every dollar a purpose. Inside The Smell of Money™ Community, you'll learn how to: Organize your cash flowEliminate debt strategicallyBuild lasting wealth with confidenceCalm your nervous system around moneyMake financial decisions without second-guessing yourself Join the community and start building wealth with confidence. Thank you for tuning into this week’s episode of I Date Money! Remember, it doesn't matter how much money you make; it's what you do with it🗝️🌬️💖💸 Intro/Outro music "IDM" by Christa Lily

    Faith, Finances & Building 
a Business That Lasts 
with Elaine Lankford
  2. 6d ago

    Your Business Should Serve Your Life with Suzanne Castle

    Save $500–$2,000 in hidden money leaks, organize your cash flow, and create a money system that actually works with the Money Hunt found inside the Smell of Money Community.  Join here: https://www.skool.com/the-smell-of-money/about Is your business supporting the life you want or consuming it? In this episode of iDateMoney®, Lisa Drennon sits down with Suzanne Castle, Chief Sparkle Officer, visionary strategist, award-winning speaker, and modern fairy godmother of business. Suzanne helps ambitious women trade “beige success” for a business filled with energy, expansion, and ease. She shares how a career-ending fall took her from the theater stage into entrepreneurship and how saying yes to one speaking opportunity eventually helped her build a successful business. Lisa and Suzanne discuss why multi-passionate female entrepreneurs often become overwhelmed, burn out, or want to burn everything down. The problem isn’t always the business itself. It may be conflicting advice, shiny-object syndrome, unclear systems, or never giving one strategy enough time to work. In this episode, you’ll discover: Why your business should serve your life—not the other way aroundHow changing strategies too quickly keeps you from gathering useful dataWhy Suzanne plans and tests her business decisions in 90-day cyclesThe difference between honoring your feelings and allowing them to run your businessWhy you should understand every part of your business before delegating itHow to recognize when it’s time to hire supportWhy rest, me time, and vacations are essential business strategiesWhat falls apart when you step away—and what that reveals about your systemsHow separating your business and personal money creates a stronger financial foundationSuzanne’s unexpected recommendation for regaining control? Take a real vacation, including a vacation from email and notifications. Giving your brain space to breathe can reveal what’s working, what needs a better system, and what you’re ready to release. Your money move after listening: schedule time away from your business and notice what you believe will fall apart without you. That answer may reveal the system or support you need next. Connect with Suzanne Castle: SuzanneCastle.com Thank you for tuning into this week’s episode of I Date Money! Remember, it doesn't matter how much money you make; it's what you do with it🗝️🌬️💖💸 Intro/Outro music "IDM" by Christa Lily

    Your Business Should Serve Your Life with Suzanne Castle
  3. Jul 18

    Playbook for Scaling Without Burning Out Featuring Michelle Puccinelli

    Save $500–$2,000 in hidden money leaks, organize your cash flow, and create a money system that actually works with the Money Hunt found inside the Smell of Money Community. Join here: https://www.skool.com/the-smell-of-money/about In this episode of iDateMoney, Michelle Puccinelli joins Lisa Drennon to talk about the entrepreneurial journey most people don't show you: the mindset shifts, the money mistakes, and the systems that actually build a sustainable business. Michelle breaks down the real difference between marketing and sales, where AI belongs in your business (and where it doesn't), and how to know when it's time to bring in support instead of doing it all yourself. If your money feels messy right now, this conversation gives you a clear next step. Key Topics Mindset shifts from scarcity to abundanceBuilding a profitable and sustainable businessEffective marketing and sales strategiesUsing AI to enhance business operations without losing authenticityFinding and delegating to the right virtual support Chapters 00:00 Introduction to Messy Money01:49 Michelle's Entrepreneurial Journey04:52 The Role of Virtual Assistants07:58 Money Mindset and Overcoming Scarcity10:26 Marketing vs. Sales: Understanding the Difference15:51 Implementing Business Strategies for Success19:02 AI vs. Human Support in Business24:38 Finding the Right Virtual Assistant26:40 Best Financial Advice for Entrepreneurs Connect with Michelle Instagram: https://www.instagram.com/michellepuccinelli/Virtual Work Studio: https://virtualworkstudio.com Thank you for tuning into this week’s episode of I Date Money! Remember, it doesn't matter how much money you make; it's what you do with it🗝️🌬️💖💸 Intro/Outro music "IDM" by Christa Lily

    Playbook for Scaling 
Without Burning Out 
Featuring Michelle Puccinelli
  4. Jul 14

    The Wealth You’re Chasing Won’t Make You Happy with Mike Wood

    Save $500–$2,000 in hidden money leaks, organize your cash flow, and create a money system that actually works with the Money Hunt found inside the Smell of Money Community.  Join here: https://www.skool.com/the-smell-of-money/about Have you ever felt like you're doing everything "right" making more money, building your business, checking all the boxes yet still feel anxious, overwhelmed, or like something is missing? In this episode of iDateMoney®, Lisa Drennon sits down with Mike Wood, creator of Learn to Love Being You, to explore the powerful connection between mindset, gratitude, nervous system regulation, and wealth. Mike shares the personal story of reaching every financial milestone he thought would finally make him happy only to discover the real work began within. Together, Lisa and Mike discuss: Why chasing money never creates lasting fulfillmentHow gratitude changes your brain chemistryThe surprising connection between cortisol, fear, and financial decisionsWhy entrepreneurs struggle with burnoutThe importance of being present instead of constantly strivingHow negative thinking literally limits your ability to see opportunitiesPractical tools to calm anxiety and regain clarityWhy wealth is an internal state before it becomes a financial oneIf you've ever felt overwhelmed by your finances, anxious about your future, or stuck in survival mode, this conversation will help you breathe a little deeper—and think a little differently. Key Takeaways✔ Wealth starts with your relationship with yourself. ✔ Gratitude shifts your nervous system from survival into possibility. ✔ Fear narms creativity and decision-making. ✔ Money isn't the destination—it's simply a tool. ✔ Presence is one of the greatest gifts you can give yourself and others. ✔ Your thoughts create the reality you experience. Resources MentionedMike Wood Learn to Love Being YouFree first lesson and guided breathwork exercises: mwoodmindset.com/idatemoney Memorable Quote"It doesn't matter how much money you have—it's what you do with it." — Lisa Drennon Thank you for tuning into this week’s episode of I Date Money!Remember, it doesn't matter how much money you make; it's what you do with it 🗝️🌬️💖💸 Intro/Outro music "IDM" by Christa Lily

    The Wealth You’re Chasing Won’t Make You Happy with Mike Wood
  5. Jul 9

    How I Paid Off $100,000 of Debt in Six Months

    Save $500–$2,000 in hidden money leaks, organize your cash flow, and create a money system that actually works with the Money Hunt found inside the Smell of Money Community.  Join here: https://www.skool.com/the-smell-of-money/about What if your biggest money problem isn't your income? What if it's the relationship you have with money? In this deeply personal episode, I'm sharing the story I've never told in this much detail from filing bankruptcy at 22 as a single mom to paying off over $100,000 of debt in just six months and retiring from my 30-year career with the Social Security Administration two and a half years early. For years, I believed I wasn't good with money. I worked multiple jobs. I taught personal finance. I helped others manage their money. Yet I was trapped in a cycle of debt that kept repeating itself. Everything changed when I stopped trying to fix my finances and started healing my relationship with money. In this episode you'll discover: • Why earning more money didn't solve my financial stress • The hidden emotional patterns that kept me recreating debt • How my Money Multiplier System™ was born • Why restrictive budgets never worked for me • The simple Money Map that finally gave every dollar a purpose • How aromatherapy and nervous system work accelerated my financial transformation • The debt payoff strategy that helped me eliminate $100,000 in six months • Why confidence—not income—is the foundation of wealth If you're making good money but still wondering where it all goes... If you're tired of feeling guilty every time you spend... If you've ever thought, "I'm just not good with money"... This episode is for you. Thank you for tuning into this week’s episode of I Date Money! Remember, it doesn't matter how much money you make; it's what you do with it🗝️🌬️💖💸 Intro/Outro music "IDM" by Christa Lily

    How I Paid Off $100,000 of 
Debt in Six Months
  6. Jul 7

    Making More Money Won't Fix Your Finances Until You Do This One Thing

    The Smell of Money is where multi-passionate female entrepreneurs learn to stop avoiding their numbers, organize their cash flow, and build a healthier relationship with money without shame, confusion, or overwhelm. Inside, you’ll learn how to give every dollar a job, understand what your money is telling you, and create calm, confident cash flow that supports your business, your life, and your future wealth. It's time to OWN Your Money: https://www.skool.com/the-smell-of-money/about?ref=96c634a120914b7b90466c17b957e4f2 🗝️🌬️💖💰 Making more money online doesn't automatically create wealth. Financial confidence does. If you've ever looked at your business and wondered, "Where did all my money go?" this episode is for you. Too many women entrepreneurs are generating revenue, signing new clients, and building multiple income streams, yet they still feel financially stressed. The problem isn't a lack of income. It's the lack of a clear cash flow system. In this solo episode of iDateMoney®, Lisa Drennon shares why chasing more revenue without a financial plan only creates more pressure. She opens up about her own journey from bankruptcy to paying off $100,000 of debt in six months, retiring two and a half years early, and creating the Money Multiplier System™ that helped her transform her relationship with money. You'll discover why profit is more important than revenue, how emotional spending quietly steals your wealth, and why giving every dollar a purpose is the fastest path to financial confidence. Instead of relying on your bank balance to make decisions, you'll learn how to build a simple cash flow system that helps you know exactly what you can spend, save, invest, and enjoy without guilt. In this episode, you'll learn:• Why revenue and profit are two completely different numbers • The biggest reason successful entrepreneurs still feel broke • How hidden money leaks quietly drain thousands of dollars every year • Why making more money won't solve financial stress • The emotional patterns that keep women stuck in overspending and avoidance • How to stop running your business like a hobby and start leading it like a CEO • The power of giving every dollar a specific job • How the Money Map creates calm, confident cash flow Timestamped Chapters00:00 Busy or profitable? 01:30 Why making more money isn't the answer 03:30 Revenue vs. profit explained 04:45 The biggest cash flow mistakes entrepreneurs make 06:00 Setting a real profit goal 07:00 Why your relationship with money matters more than budgeting 09:00 Lisa's bankruptcy story and financial wake-up call 11:00 Why hustling harder isn't creating wealth 13:30 Every dollar needs a job 14:15 The Money Multiplier System™ 15:45 Building your Money Map 17:30 How intentional spending creates financial confidence 18:45 Invitation to the Calm Cash Flow Workshop Resources➡️ Register for the Calm Cash Flow Workshop: https://workshop.idatemoney.com/calm-cash-flow-workshop Thank you for tuning into this week's episode of iDateMoney! Remember, it doesn't matter how much money you make; it's what you do with it 🗝️🌬️💖💸 Intro/Outro music "IDM" by Christa Lily

  7. Jul 1

    How Alignment Creates Financial Confidence with Kristan Swan

    The Smell of Money is where multi-passionate female entrepreneurs learn to stop avoiding their numbers, organize their cash flow, and build a healthier relationship with money without shame, confusion, or overwhelm. Inside, you'll learn how to give every dollar a job, understand what your money is telling you, and create calm, confident cash flow that supports your business, your life, and your future wealth. It's time to OWN Your Money: https://www.skool.com/the-smell-of-money/about?ref=96c634a120914b7b90466c17b957e4f2 If you're making money but still feel scattered, overwhelmed, or afraid to trust yourself, your money story may be running your business more than you realize. In this episode of iDateMoney®️, Lisa Drennon sits down with former business coach turned life and spiritual guide Kristan Swan for an honest conversation about the hidden beliefs that quietly shape our financial decisions. They explore how childhood scarcity, people-pleasing, fear of judgment, and misalignment can keep entrepreneurs working harder while moving further away from the life they truly want. Kristan shares how she transitioned from business coaching into helping people reconnect with themselves through intentional reflection, journaling, and values-based living. Together, she and Lisa discuss why success begins with awareness, how slowing down can actually accelerate your growth, and why building wealth starts by understanding the stories you tell yourself about money. About our guest: Kristan Swan is a former business coach turned life and spiritual guide who helps people discover their truth, clarify their values, and cultivate a more intentional way of living. Through guided journals, workshops, and retreats, she empowers people to create aligned lives built on self-awareness instead of fear. Connect with Kristan at KristanSwan.com. In this episode, you'll learn: Why your money story influences every financial decision you make How childhood scarcity patterns continue to affect entrepreneurs today Why working harder isn't always the solution to financial stress The power of journaling and brain dumps for creating clarity How people-pleasing keeps women financially and emotionally exhausted Why alignment creates more sustainable success than hustle Practical ways to pause, reflect, and reconnect with what truly matters How community and simple daily practices help build lasting confidence Timestamped Key Moments 00:00 Why entrepreneurs panic when unexpected tax bills arrive 02:20 Meet Kristan Swan and her journey from business coach to spiritual guide 05:00 Growing up with scarcity and how inherited money beliefs shape adulthood 10:00 Why awareness is the foundation for both business and personal growth 13:20 The power of slowing down instead of pushing harder 15:00 Brain dumps, journaling, and uncovering hidden money patterns 18:30 Community, accountability, and taking small aligned actions 20:15 Why women struggle to prioritize themselves without guilt 23:15 The biggest mistake Kristan made when changing careers 27:50 How to connect with Kristan and begin your own alignment journey Thank you for tuning into this week's episode of iDateMoney®️! Remember, it doesn't matter how much money you make; it's what you do with it 🗝️🌬️💖💸 Intro/Outro music "IDM" by Christa Lily

    How Alignment Creates Financial Confidence with Kristan Swan
  8. Jun 25

    Making More Money Won’t Fix Messy Money with Stephanie Peirolo

    The Smell of Money is where multi-passionate female entrepreneurs learn to stop avoiding their numbers, organize their cash flow, and build a healthier relationship with money without shame, confusion, or overwhelm. Inside, you’ll learn how to give every dollar a job, understand what your money is telling you, and create calm, confident cash flow that supports your business, your life, and your future wealth. It's time to OWN Your Money: https://www.skool.com/the-smell-of-money/about?ref=96c634a120914b7b90466c17b957e4f2 Making more money online will not create wealth if your money decisions are still being driven by fear, stress, old money stories, and survival mode. In this episode of iDateMoney®️, Lisa sits down with executive coach and author Stephanie Peirolo for a powerful conversation about money stories, decision-making, divorce, debt, burnout, and what it really takes to build financial stability as a woman. Stephanie shares how childhood scarcity, gender roles, single motherhood, and financial shame shaped her relationship with money, and how she eventually rebuilt financial security while learning to make decisions from alignment instead of panic. Together, Lisa and Stephanie unpack why messy money is rarely just a math problem. It is often tied to the stories we inherited about work, worth, success, and what women are allowed to have. They also talk about the pressure to overwork, the cost of financial instability after divorce, and why women need to stop sacrificing their own financial well-being to rescue everyone else. About our guest: Stephanie Peirolo is a board-certified executive coach, author of The Saint and the Drunk, and host of The Bad Boss Brief. She helps leaders make intentional decisions, lead with clarity, and build lives that align with their values. Connect with Stephanie at spayrolo.com In this episode, you’ll learn:Why messy money is often a relationship problem, not just a budgeting problemHow childhood scarcity and family money stories shape adult financial decisionsThe hidden financial impact of divorce, caregiving, and being a single motherWhy more income does not automatically create peace, profit, or stabilityHow women can stop over-giving financially and protect their own futureWhy decision-making gets easier when you understand your values, responsibilities, and realityHow to define wealth on your own terms instead of chasing someone else’s numberTimestamped key moments00:00 Messy money, money shame, and why women avoid their numbers 02:00 Stephanie’s book The Saint and the Drunk and decision-making with intention 04:00 Money narratives, inherited scarcity, and cultural conditioning 07:00 Divorce, single motherhood, and financial survival mode 11:00 Career choices, writing dreams, and making practical money decisions 13:45 Shame, systemic barriers, and forgiving yourself for past money struggles 15:40 How Stephanie got out of debt and built financial security 19:25 What women need to stop doing with money immediately 20:00 Redefining success and choosing your own wealth number 22:00 Stephanie’s shift into executive coaching and intentional leadership 24:40 Where to connect with Stephanie and get the book Thank you for tuning into this week’s episode of I Date Money! Remember, it doesn't matter how much money you make; it's what you do with it 🗝️🌬️💖💸

    Making More Money Won’t Fix Messy Money with 
Stephanie Peirolo
5
out of 5
5 Ratings

About

Multi-passionate female entrepreneurs who've built real income and assets but still feel scattered with money need the Money Multiplier System™ to organize cash flow, pay themselves consistently, and turn income into lasting wealth, not another budget. Welcome to iDateMoney®️ with Lisa Drennon, Wealth Activator, author, and founder of the iDateMoney® brand. If you're running multiple income streams, own assets, and work hard for your money but can't see where it's actually going or make confident financial decisions, this podcast is for you. Here, we skip the generic budgeting advice and dive into: ✓ The ABCs of Wealth framework (Activate • Build • Cash Flow) ✓ The Money Multiplier System™ for organizing personal money ✓ The Calm Cash Flow Strategy that pays you consistently ✓ Practical tools to eliminate hidden money leaks and build lasting wealth Each episode teaches you how to OWN Your Money with the confidence and clarity you deserve. Your money challenge isn't about earning more. It's about having a system you trust. Get ready to multiply your wealth; because it doesn't matter how much money you have-it's what you do with it.🗝️🌬️💖💰

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