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

Lisa Drennon
  • 4.9 (64)
  • Business

You work hard to make money. But are you keeping enough of it? iDateMoney® is the podcast for U.S.-based solopreneurs and couples running small businesses who want to take control of their cash flow, increase profitability, and build lasting wealth without restrictive budgets or sacrificing the life they love. Hosted by Lisa Drennon, Profit Strategist, Author, and Independent Insurance Broker, each episode features real conversations with successful entrepreneurs about the money decisions, challenges, and lessons behind building a business and creating financial freedom. Discover how to OWN Your Money: Organize cash flow, build Wealth, and Navigate financial decisions with clarity and confidence. Because it doesn't matter how much money you have—it's what you do with it that matters. 🗝️🌬️💖💸

  1. 5d ago

    Build Wealth with Rental Properties Without Being a Landlord

    What if you could build wealth through real estate without fixing toilets, managing tenants, or buying property in your own backyard? In this episode of iDateMoney®, Lisa Drennon sits down with real estate investor and author Adiel Gorel, who shares how he turned his Silicon Valley income into a portfolio of rental properties and helped investors purchase more than 10,000 homes across the United States. With 42 years of real estate investing experience, Adiel explains why earning more money isn't always the answer. It's what you do with the money you already earn that creates opportunities for long-term wealth. What You'll DiscoverWhy a big income doesn't guarantee wealth: How to turn the money you earn into assets instead of watching it disappear.Investing outside your hometown: Why buying rental properties in more affordable markets can make financial sense.You don't have to be a landlord: How professional property management can handle the day-to-day responsibilities.The power of a 30-year fixed-rate mortgage: How fixed principal and interest payments, inflation, and property appreciation can affect long-term wealth.Why Adiel prefers new single-family homes: His approach to choosing properties and markets.Start with one property: Why building confidence through experience may be more valuable than trying to buy an entire portfolio overnight.Stop saying "I can't afford it": Why understanding your numbers and exploring your options matters before making a financial decision.Can Rental Properties Help You Build Wealth?Adiel shares the story of an investor who purchased 19 rental homes, eventually sold four, and used the proceeds to pay off the remaining 15 mortgages. By age 55, that investor had retired from his Silicon Valley career. It's an example of what strategic real estate investing can accomplish, although every investment comes with risks, expenses, and different financial outcomes. Lisa brings the conversation back to an important principle: Know your numbers, understand your cash flow, and create a financial roadmap before making your next money move. Because investing isn't about following someone else's strategy. It's about knowing what works for your financial situation. 🔗 Connect with Adiel GorelWebsite: https://www.icgre.com Email: info@icgere.com Book: Remote Control Retirement Riches Ready to Date Your Money?You don't need another restrictive budget. You need to know where your money is going and what you want it to do for you. Join The Smell of Money and START HERE with iDateMoney®.: https://www.skool.com/the-smell-of-money/about?ref=3f83ec6aaacd4b21bdedb6f3b643eef8&utm_campaign=skool_link_direct_message&utm_content=7029c31a6d4048d2b68fdf659b17da62 You'll take a simple look at your cash flow, uncover money that's hiding in plain sight, and start giving your dollars a job that supports the life you're actually building.

    Build Wealth with Rental Properties Without Being a Landlord

  2. Oct 19

    Stop Neglecting Your Own Money (The Plumber's Leaky Toilet)

    Your business is bringing in money. Clients are paying. Revenue is growing. So why does your personal bank account tell a completely different story? You started your business to create financial independence, not another job that leaves you exhausted and wondering where all the money went! In this episode of iDateMoney®, I'm joined by Iyanna Vaughn, founder and CEO of Lovely Financial Groups, fractional CFO to talk about one of the biggest mistakes entrepreneurs make: building a business that generates revenue but doesn't consistently pay its owner. And Iyanna knows this struggle firsthand! While helping clients reach six- and seven-figure revenue milestones, she realized she was neglecting her OWN finances. Everything changed when she started dating her money, giving her personal and business finances the same attention she gave her clients. The result? She reached six figures in business revenue in 2019 and $250,000 in 2020! We're talking CEO pay, cash flow management, profitability, inherited-money beliefs, and why making MORE money isn't always the answer. Because your business revenue is NOT your personal income! 💰 What You'll Discover Why six-figure revenue doesn't guarantee financial security. How to determine your CEO pay BEFORE setting revenue goals. Why mixing business and personal finances creates costly problems. How childhood money stories influence your financial decisions. Why weekly money dates can transform your cash flow. How to reverse-engineer revenue goals based on the lifestyle YOU want. Why building a sustainable business requires systems, boundaries, and an exit strategy. ⏱️ Episode Highlights 00:00 — Where is your cash flow going? 02:39 — Childhood money stories and the hustle mentality 06:27 — From caregiving to entrepreneurship 08:48 — Helping seven-figure clients while neglecting her own money 11:05 — The danger of mixing business and personal finances 13:07 — Creating a percentage-based spending plan 17:55 — How much should you pay yourself as CEO? 19:23 — Reverse-engineering revenue and profit goals 24:15 — Building a business when life gets complicated 26:38 — Redesigning a business for flexibility 31:53 — Protecting your finances with checks and balances 💖 Connect With Iyanna Vaughn: lovelyfinancials.com Ready to Date Your Money? 💖💸 You don't need another restrictive budget. You need to know where your money is going and what you want it to do for you. Join The Smell of Money and START HERE with iDateMoney®: https://www.skool.com/the-smell-of-money/about?ref=3f83ec6aaacd4b21bdedb6f3b643eef8&utm_campaign=skool_link_direct_message&utm_content=7029c31a6d4048d2b68fdf659b17da62 You'll take a simple look at your cash flow, find money that's hiding in plain sight, and start giving your dollars a job that supports the life you're actually building. iDateMoney® is where you learn to OWN Your Money: O — Organize your cash flow W — Build Wealth N — Navigate your finances So you can find money leaks, reduce debt, build savings and wealth, and make confident decisions with your money. Because it doesn't matter how much money you have—It's what you do with it that matters. 🗝️🌬️💖💸 Intro/Outro music "IDM" by Christa Lily

    Stop Neglecting Your Own Money (The Plumber's Leaky Toilet)

  3. Oct 10

    The Hidden Cost of Playing by Someone Else’s Money Rules

    Ready to Date Your Money? You don't need another restrictive budget. You need to know where your money is going—and what you want it to do for you. Join The Smell of Money and START HERE with iDateMoney®: https://www.skool.com/the-smell-of-money/about?ref=b841fa9d675f452e8995cb3c0d4e18fd&utm_campaign=skool_link_direct_message&utm_content=cc5ec984cc5a4c8cb4aa956a5fd99925 You'll take a simple look at your cash flow, uncover money that's hiding in plain sight, and start giving your dollars a job that supports the life you're actually building. What if the rules you've been following about money, success, and your career were never yours to begin with? In this episode of iDateMoney®, I'm sitting down with Toni Will, General Manager and Governor of the Kalamazoo Wings, international speaker, coach, and author of Rebellious Success. We're talking about the money stories we inherit, the pressure to achieve, why making mistakes is part of building wealth, and what happens when you stop chasing someone else's definition of success. Toni shares how removing alcohol from her life gave her back approximately 800 hours a year, why she values mission over money, and how her six leadership pillars have helped her navigate everything from professional sports to entrepreneurship. We also get into a conversation many entrepreneurs need to hear: Just because you invest in your dream doesn't mean you should expect an immediate return. If you've ever questioned whether you're doing enough, earning enough, or building your business the "right" way, this conversation will challenge you to think differently. Because success isn't about following everybody else's rules. It's about deciding what matters to YOU and making intentional choices with your time, energy, and money. What You'll DiscoverWhy inherited money stories can keep you playing by rules that no longer serve you.Why keeping your nine-to-five while growing a business can be a strategic financial decision.The six leadership pillars that helped Toni transform a professional hockey organization.Episode Highlights00:00 Cash flow, intentional spending, and defining your lifestyle 02:19 Meet Toni Will and the evolution from Toni 1.0 to 2.0 03:47 Marriage, money management, and financial independence 06:08 Building a business without leaving a successful career 08:01 Toni's alcohol-free journey and reclaiming her time 10:59 The six leadership pillars 15:55 The financial realities of publishing a book 18:18 Managing expectations and evaluating ROI 21:02 Leading a major new arena project in Kalamazoo 24:55 The message behind Rebellious Success Whether you're building a business, paying off debt, publishing a book, or creating your next chapter, your money decisions should support the life YOU want to live.Connect With Toni Will: toniwill.comiDateMoney® is where you learn to OWN Your Money: O — Organize your cash flow W — Build Wealth N — Navigate your finances So you can uncover money leaks, reduce debt, build savings and wealth, and make confident decisions with your money. Because it doesn't matter how much money you have, it's what you do with it that matters. 🗝️🌬️💖💸 Intro/Outro music "IDM" by Christa Lily

    The Hidden Cost of Playing by Someone Else’s Money Rules

  4. Sep 29

    What Is Your Money Actually For?

    Ready to Date Your Money? 💖💸You don't need another restrictive budget. You need to know where your money is going and what you want it to do for you. Join The Smell of Money and START HERE with iDateMoney®: https://www.skool.com/the-smell-of-money/about You'll take a simple look at your cash flow, uncover money that's hiding in plain sight, and start giving your dollars a job that supports the life you're actually building. 👉 JOIN THE SMELL OF MONEY + START HERE: https://www.skool.com/the-smell-of-money/about How much money do you actually need to retire? $1 million? $2 million? More? The answer isn't that simple. In this episode of iDateMoney®, Lisa Drennon sits down with financial educator, author, speaker, and co-founder of Stonebriar Wealth Advisors, Gary Preisser, to challenge the idea that building wealth is simply about accumulating as much money as possible. Gary believes wealth isn't a trophy. It's a tool. And the value of that tool comes from what you're able to do with it. Together, Lisa and Gary talk about why cash flow—not an arbitrary retirement number—needs to be part of the conversation when you're trying to determine whether you can afford to retire. Two people can have the exact same amount saved and be in completely different financial situations based on their expenses, Social Security, pensions, income sources, debt and the life they actually want to live. That's why the question isn't simply: "How much money do I have?" It's also: "What do I need this money to do?" In this episode, you'll hear:Why there isn't one magic number you need to retireHow your current and future cash flow affect retirement readinessHow unintentional spending can quietly consume even a strong incomeIf you're not intentional about where your money goes, it has a way of disappearing into expenses that may not even matter to you. Your income can increase. Your investments can grow. Your net worth can climb. But if you don't know why you're building that wealth, you can spend decades accumulating money without ever allowing it to create the life you were building it for. And eventually, somebody is going to spend that money. Why shouldn't some of that somebody be you? Take the trip. Help your kids or grandkids if that's important to you. Create experiences. Give. Build something. Retire. Or simply create enough predictable cash flow that you don't have to worry every month. Your answer doesn't have to look like anyone else's. That's the point. Connect with GaryGary Preisser is a financial educator, author, speaker and co-founder of Stonebriar Wealth Advisors. https://www.stonebriarwealthadvisors.com/ About iDateMoney®iDateMoney® is where you learn to OWN Your Money: O — Organize your cash flow W — Build Wealth N — Navigate your finances So you can uncover money leaks, reduce debt, build savings and wealth, and make confident decisions with your money. Because it doesn't matter how much money you have— It's what you do with it that matters. 🗝️🌬️💖💸 Intro/Outro music "IDM" by Christa Lily

    What Is Your Money Actually For?

  5. Sep 18

    When Your Health Is Costing You Your Wealth

    Ready to make your next $25K without signing a single new client? Apply for your seat at The Profit Table: https://idatemoney.systeme.io/applied 🗝️🌬️💖💰 What happens when your health starts draining more than your energy? It can drain your time, your income, your savings, your ability to work, and even your confidence in the decisions you're making. In this episode of iDateMoney®, I sit down with Marla Chaffin, founder of Symptoms Make Sense, to talk about something we don't discuss enough: The connection between your health and your wealth. Marla spent years searching for answers after chronic pain and unexplained symptoms turned her life upside down. Her journey took her through doctors, hospitals, specialists, medications, lifestyle changes, and ultimately a completely different way of looking at her health. And as we talked, one thing became very clear: Health and money have a lot more in common than we realize. When something isn't working, we often want the fastest solution. A restrictive diet. A restrictive budget. Another supplement. Another program. Another financial strategy. But lasting change usually doesn't come from another quick fix. It comes from understanding what's actually happening, questioning the patterns you've been operating from, and taking small, intentional steps toward something different. In this episode, we talk about:Marla's four-year search for answers after her health suddenly declinedThe financial cost of chronic illness—including lost time, lost wages, travel, specialists, and treatmentWhy restriction can backfire in both health and moneyWhy quick fixes rarely create sustainable changeWhy understanding the root of a problem can change the decisions you makeHow health challenges can lead to debt when medical expenses and lost income collide You don't completely change decades of health habits overnight. And you don't completely change decades of money habits overnight either. You start paying attention. You ask better questions. You learn what works for you. And then you take the next step. Because whether we're talking about your health or your money, being intentional about your choices matters. Connect with MarlaMarla spends most of her time inside her free Skool community, Symptoms Make Sense: https://www.skool.com/symptoms-make-sense/about?ref=96c634a120914b7b90466c17b957e4f2 Ready to start looking at your money differently?Inside The Smell of Money, we're having the money conversations most people avoid. You'll learn how to organize your cash flow, identify where your money is actually going, make more intentional spending decisions, and give every dollar a job without putting yourself on another restrictive budget. Join here: https://www.skool.com/the-smell-of-money/about This episode shares personal experiences and educational discussion and is not a substitute for individualized medical advice. Talk with an appropriate healthcare professional before changing medications, supplements, or treatment.

    When Your Health Is Costing You Your Wealth

  6. Sep 11

    How to Find Your Next $25K Without Signing a New Client | The Profit Table

    Your next $25K isn't hiding in more clients. It's already moving through your business; you just haven't claimed it. Welcome to the debut of The Profit Table: a bi-monthly conversation for established women entrepreneurs who make good money but don't feel in control of it. One question runs the whole room: if you couldn't sign another client for 90 days, what would you change inside the business you already have to create your next $25K? No hot seats. No pressure to share private numbers. Just real money talk you can put to work the same day because it's not how much money you have, it's what you do with it. 🪑 Want a seat at the next table? It's by application: https://forms.gle/D4uxd6Vx9m9fQHbP9 💸 Come find your money inside The Smell of Money: https://www.skool.com/the-smell-of-money/about Hosted by Lisa Drennon — Wealth Activator, iDateMoney®

    How to Find Your Next $25K Without Signing a New Client | The Profit Table

  7. Sep 9

    How Your Money Mindset Affects Cash Flow, Business Debt & Profit

    How Your Money Mindset Affects Cash Flow, Business Debt & ProfitReady to make your next $25K without signing a single new client? Apply for your seat at The Profit Table: https://forms.gle/r6BavN4zASdsJv5u9 What if your biggest money problem isn’t actually the money? Your money mindset, cash flow habits, and beliefs about wealth can influence how you respond to business debt, slow revenue months, profit, and even how much money you allow yourself to keep. In this episode of iDateMoney, I sit down with Lisa Somers, CEO of Marketplace Superheroes, to talk about the side of entrepreneurship that doesn’t always make it onto social media. Lisa shares how she went from training to become a psychologist to helping build a multimillion-dollar online education company—and what happened when that successful business suddenly had to deal with more than $1 million in debt. And yes—they paid it off. But this conversation isn't just about debt payoff. It's about what happens between your ears when the numbers don't look the way you want them to. In This Episode, We Talk About:💸 How childhood and cultural beliefs about wealthy people can affect your ability to receive and keep money 💸 Why making more money doesn’t automatically eliminate your money fears 💸 The difference between a financial problem and the emotional story you attach to it 💸 How Lisa and her brother approached more than $1 million in business debt 💸 Why a multimillion-dollar business doesn't necessarily mean the owner has massive personal cash flow 💸 Separating business finances from personal finances 💸 Why entrepreneurship isn't supposed to feel amazing 100% of the time 💸 The danger of comparing your financial life to what another entrepreneur appears to have 💸 Why following a proven business model can shorten your learning curve 💸 Creating additional income streams without immediately quitting your 9-to-5 One of my favorite takeaways from this conversation: Revenue being down is financial information. It doesn't automatically mean your business is failing. It doesn't mean you're unsafe. And it doesn't mean everything is falling apart. The question becomes: What does the number tell you—and what action can you take next? That distinction can completely change the way you make money decisions. About Lisa SomersLisa Somers is the CEO of Marketplace Superheroes, an online education company that has helped more than 10,000 people build additional income streams through online business. After working across virtually every department in the company, Lisa now specializes in scaling education businesses, building high-performing remote teams, strategic partnerships, and direct-response marketing. Her own journey has included everything from learning entrepreneurship from scratch to helping navigate and eliminate more than $1 million in business debt. Resources MentionedMarketplace Superheroes: marketplacesuperheroes.com About iDateMoney®iDateMoney® is where women entrepreneurs learn to OWN Your Money: O — Organize your cash flow W — Build Wealth N — Navigate your finances So you can uncover money leaks, pay yourself consistently, reduce debt, build wealth, and make confident financial decisions. Because it doesn't matter how much money you make-It's what you do with it that matters.🗝️🌬️💖💸 Intro/Outro music "IDM" by Christa Lily

    How Your Money Mindset Affects Cash Flow, Business Debt & Profit

  8. Sep 1

    How to Turn Your Life Experience Into a Profitable Coaching Business

    Ready to make your next $25K without signing a single new client? Apply for your seat at The Profit Table: https://forms.gle/r6BavN4zASdsJv5u9 What if the experiences you've lived through could become the foundation of a profitable business? In this episode of iDateMoney®, Lisa Drennon sits down with Dr. Lisha Antiqua, founder of Your Own University and creator of the Amazing YOU Method, for a powerful conversation about identity, healing, expertise, entrepreneurship, and getting paid to be YOU. Dr. Lisha shares how her own experiences with trauma, healing, education, and entrepreneurship ultimately became part of her life's work, and why your lived experience can become valuable intellectual property when you learn how to turn it into a message, methodology, program, or business. We also get into an important conversation about coaching: When is your personal experience enough? When do you need additional education or certification? And why is staying within your expertise so important when you're responsible for helping someone else transform their life? You'll discover: How your lived experiences can become valuable expertiseWhy identity matters when building a business around YOUThe difference between coaching, mentoring, and teachingWhen education and certifications actually matterHow to turn your story into a message, methodology, or offerWhy authenticity can be more powerful than following someone else's marketing formulaHow to identify your zone of geniusWhy entrepreneurship requires a financial plan—not just a desire to make more moneyThe importance of setting a profit-margin goalWhy tenacity and purpose matter when business feels like a roller coasterHow to build a business that pays you for the wisdom you've already earnedAs Lisa explains, entrepreneurship isn't a shortcut to fast money. You need a business plan, a financial strategy, and a clear understanding of what you want your business to produce. Because you can make as much money as you want but if you don't know what to do with it, making more won't solve the problem. Connect with Dr. Lisha AntiquaVisit Your Own University: http://www.lishaantiqua.com/ and take the Soul Purpose Quiz to discover whether you're in the Rebuilding, Messenger, or Architect stage of turning your experience and expertise into a message, movement, and profitable business. About iDateMoney®iDateMoney® is where women entrepreneurs learn to OWN Your Money: O — Organize your cash flow W — Build Wealth N — Navigate your finances So you can uncover money leaks, pay yourself consistently, reduce debt, build wealth, and make confident financial decisions. Because it doesn't matter how much money you make-It's what you do with it that matters.🗝️🌬️💖💸

    How to Turn Your Life Experience Into a Profitable Coaching Business
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4.9
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You work hard to make money. But are you keeping enough of it? iDateMoney® is the podcast for U.S.-based solopreneurs and couples running small businesses who want to take control of their cash flow, increase profitability, and build lasting wealth without restrictive budgets or sacrificing the life they love. Hosted by Lisa Drennon, Profit Strategist, Author, and Independent Insurance Broker, each episode features real conversations with successful entrepreneurs about the money decisions, challenges, and lessons behind building a business and creating financial freedom. Discover how to OWN Your Money: Organize cash flow, build Wealth, and Navigate financial decisions with clarity and confidence. Because it doesn't matter how much money you have—it's what you do with it that matters. 🗝️🌬️💖💸

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