The Richest Real Estate Agent Podcast

Ben Oosterveld

Interviewing the top influencers and leaders in the real estate and mindset space. This podcast explores the emotional intelligence and marketing needed to be a top agent year after year while managing the pressures of success on their lifestyle, family, and mental health. The real estate industry is obsessed with the "next sale", but rarely talks about what to do when the next sale is NOT the biggest problem anymore. This podcast helps agents get clear on what they want, how to get out of their own ways and shift from being a high-service grinder to an energized, self-aware business owner.

  1. The Problem With Traditional Business Planning

    Mar 27

    The Problem With Traditional Business Planning

    In this episode, Ben explains why most business plans push agents toward burnout, and how to flip the process so your business actually supports the life you want. Instead of planning for more deals, Ben shows you how to design your life first, then build a business that funds it. You'll learn: Why most agents are solving the wrong problem in their business Why making more money doesn't always make you happier The four life areas that should guide every business plan How to reverse-engineer your income around the life you want Why systems and energy matter more than hustle If you've ever felt like your business is running your life instead of supporting it, this episode will change the way you think about business planning. Because the real goal isn't just a bigger business. It's a business that gives you freedom, time, and a life you actually enjoy.   Connect with Ben: https://benoosterveld.com   PLEASE LEAVE A REVIEW and SHARE this episode! It really helps the show. Listen to previous episodes on Apple Podcasts, Spotify, or wherever you get your podcasts.

    1h 26m
  2. Kiri-Maree Moore - The System Behind Life-Changing Decisions Without Regret

    Mar 25

    Kiri-Maree Moore - The System Behind Life-Changing Decisions Without Regret

    Most people think big success comes from big moments. But most of the time… it actually comes from small decisions. In this episode, Ben sits down with Kiri-Maree Moore to talk about something most people never slow down to think about. The decisions we make every day. And how those choices quietly shape the direction of our life, our business, and even our relationships. Kiri-Maree shares her idea of Return on Decision. A simple way to look at the cost and value behind the choices we make. Is this decision moving you toward the life you want… or pulling you away from it? She also walks through a simple framework that helps you see things more clearly. What in your life is draining you. What is a no-brainer that you should be doing more of. And what sits in the middle that needs a better decision. It sounds simple. But when you actually start using it, things change. Because when you start making better decisions on purpose… your time, your energy, and your business start moving in a very different direction. This episode is about clarity. And learning how to make decisions that actually move your life forward. Connect with Kiri-Maree: https://kiri-maree.com Connect with Ben: https://benoosterveld.com   PLEASE LEAVE A REVIEW and SHARE this episode! It really helps the show. Listen to previous episodes on Apple Podcasts, Spotify, or wherever you get your podcasts.

    40 min
  3. The Cost of Doing Everything Yourself - Delegating Masterclass

    Mar 23

    The Cost of Doing Everything Yourself - Delegating Masterclass

    Most agents do way too much on their own. And after a while, it starts costing them. In this episode, Ben breaks down why delegation matters so much if you want to grow your business without burning yourself out. He talks about the low-value tasks that eat up your time, drain your energy, and pull you away from the work that actually moves the needle. But this is not just about hiring help. It is about knowing what to delegate, when to do it, and why so many agents stay stuck doing everything themselves. Ben also gets into the real reason delegation feels hard for a lot of people. Control, trust, perfectionism, fear of conflict, all of it. This episode gives you a simple starting point. Rookie-level delegation stuff, but honestly, that is the point. You do not need to wait until your business is bigger. You can start now. And when you do, your business, your energy, and your life can start to open up in a whole different way. Connect with Ben: https://benoosterveld.com   PLEASE LEAVE A REVIEW and SHARE this episode! It really helps the show. Listen to previous episodes on Apple Podcasts, Spotify, or wherever you get your podcasts.

    56 min

  4. Mar 20

    The Old Real Estate Model Is Broken

    Most agents are not running a business. They are stuck in a cycle of prospecting, servicing, burning out, and starting over. In this live training, Ben breaks down why the traditional real estate model keeps even good agents exhausted and inconsistent. He shares his own story, from addiction and early success to nearly losing his marriage, and explains how that wake-up call reshaped the way he builds businesses today. Connect with Ben: https://benoosterveld.com PLEASE LEAVE A REVIEW and SHARE this episode! It really helps the show. Listen to previous episodes on Apple Podcasts, Spotify, or wherever you get your podcasts.

    2h 30m

  5. Mar 18

    Philip McKernan - Resentment Is Bad Fuel

    Resentment can be powerful. It can push you to work harder, prove people wrong, and build something extraordinary. But what if the very fuel that helped you succeed is also quietly costing you? In this episode, Ben sits down with Philip McKernan for a deeply honest conversation about anger, identity, and the hidden stories we carry. If you have ever been driven by something you cannot quite name, this episode will challenge you to look at what is really underneath it and decide whether it is time to let it go. Connect with Philip: https://philipmckernan.com/ Connect with Ben: https://benoosterveld.com   PLEASE LEAVE A REVIEW and SHARE this episode! It really helps the show. Listen to previous episodes on Apple Podcasts, Spotify, or wherever you get your podcasts.

    54 min

  6. Feb 5

    Why Most Real Estate Agents Stay Stuck in the Hustle Cycle

    Most agents are taught the exact same playbook when they start. Get your license. Post on social. Send mailers. Door knock. Hustle your face off. And look… it does work. Ben talks about that right away. You hustle, you pick up deals, pipeline starts filling up. You feel like you're finally getting traction. But then something else happens. You get busy servicing those clients… so you stop prospecting. A few months go by, and all of a sudden, the board is empty again. No deals coming in. Back into panic mode trying to refill it. That feast or famine cycle is really what Ben is breaking down in this conversation. He gets into why the traditional model is built around chasing clients… but not keeping them. No one really teaches agents how to hold relationships long-term. How to stay in touch without it feeling weird or forced. And the crazy part is that's where most of the money actually sits. He talks a lot about lifetime client value. Referrals. Repeat business. What one relationship is actually worth if you don't let it go cold after the transaction ends. There's also a big section where he walks through team structure. Why having a small, tight team can be more profitable than scaling big. How part-time support roles take pressure off without creating the risk of one full-time hire disappearing and blowing up your workflow. He even gets into the emotional side of it… like what it feels like from the client's perspective when you go from talking every day during a deal to not hearing from their agent again. Not because you didn't care. Just because you got busy. But perception matters. Overall, this episode is really about shifting from hustling deal to deal… into building something that keeps working in the background. Systems. Follow up. Nurture. Relationship equity. Stuff that doesn't feel flashy, but compounds hard over time. If you've ever felt like your business resets every time your pipeline clears out, you'll probably see yourself in this one.   Connect with Ben: https://benoosterveld.com   PLEASE LEAVE A REVIEW and SHARE this episode! It really helps the show. Listen to previous episodes on Apple Podcasts, Spotify, or wherever you get your podcasts.

    19 min

  7. Feb 2

    Three Million-Dollar Team Leaders Reveal Their Secrets

    This episode of The Richest Real Estate Agent Podcast is about what building a team actually looks like once you're in it. Ben sits down with Carson Beier, Ty Corsie, and Ron Dickson to talk through how their teams are set up, what worked, what didn't, and what they would do differently if they had to start again. They cover buyer agents, admins, support roles, and how teams change as the market shifts. But the conversation goes deeper than org charts. They talk about burnout, holding on to too much control, and the mistake of stepping away from selling too early. They also get into family life, time, and how easy it is to build something that looks great on paper but ends up costing you more than you expected. You'll hear different perspectives on leadership, hiring, and growth. Some of them even disagree, which is kind of the point. There isn't one "right" way to build a team. What works for one agent can fall apart for another if it doesn't fit who they are. They also share the systems that helped them move forward, from referral strategies to social media to client follow-up. Nothing flashy. Just things that actually fit into a busy agent's life. If you're building a team or thinking about it, this episode will help you see the trade-offs more clearly and make better decisions before you learn them the hard way.   Connect with Carson: https://www.instagram.com/thecarsonbeierteam/ Connect with Ty: https://tycorsie.com/ Connect with Ron: https://www.instagram.com/rondicksonyeg/?hl=en Connect with Ben: https://benoosterveld.com   PLEASE LEAVE A REVIEW and SHARE this episode! It really helps the show. Listen to previous episodes on Apple Podcasts, Spotify, or wherever you get your podcasts.

    25 min

  8. Jan 28

    How To Build A Thriving Real Estate Business Without Getting A Divorce

    This episode is for the agent who wants to build something big, but doesn't want to wake up one day and realize the cost was their family. Ben and Rene talk through what happens when ambition takes over. When the business is growing, the numbers look good, and from the outside, it all makes sense. But at home, the pressure never shuts off. Work follows you through the door. You're there, but you're not really there. They walk through Ben's path from survival mode into real estate, how that drive turned into control, and how "I'm doing this for us" slowly became the thing that pushed them apart. Rene shares what it's like being married to someone who never stops chasing the next win, and what changed when she finally stopped staying quiet. This is not about choosing family instead of success. It's about learning how to build a real estate business that doesn't require sacrificing the people you're doing it for. You'll hear about: The hidden pressure ambitious agents bring home without noticing Why more deals don't fix the feeling of never being done How unclear expectations wreck family life in commission businesses Why systems, hiring, and boundaries are not "nice to have" What it actually means to build a business that serves your life If you're driven, competitive, and used to pushing through everything, this episode might feel uncomfortably familiar. And useful.   Connect with Ben: https://benoosterveld.com PLEASE LEAVE A REVIEW and SHARE this episode! It really helps the show. Listen to previous episodes on Apple Podcasts, Spotify, or wherever you get your podcasts.

    53 min
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About

Interviewing the top influencers and leaders in the real estate and mindset space. This podcast explores the emotional intelligence and marketing needed to be a top agent year after year while managing the pressures of success on their lifestyle, family, and mental health. The real estate industry is obsessed with the "next sale", but rarely talks about what to do when the next sale is NOT the biggest problem anymore. This podcast helps agents get clear on what they want, how to get out of their own ways and shift from being a high-service grinder to an energized, self-aware business owner.

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