Seeing Greene with Wyatt Wolff | Episode 91
The David Greene Show
David Greene
5 • 653 Ratings
🗓️ 23 October 2025
⏱️ 69 minutes
🧾️ Download transcript
Summary
On today’s show, we did something I’ve never done before. I’m joined by Wyatt Wolff, a loan officer, who breaks down his career working with real estate investors, agents, and home buyers helping them to buy real estate. Rather than the traditional interview model where we talk to investors, today’s show focuses on those who help investors. Wyatt shares his story about working two jobs where he would work in the warehouse of a distribution center during the day and closing loans for clients at night. Wyatt shares his journey as he moved from closing loans for a bank to working at a brokerage where he has hundreds of options for clients to choose from. The conversation moves from mindset and how the W2 perspective can ruin work ethic, to practical advice on how to be effective at your job during the day. The show goes deep into the changes people need to make in order to be successful in today’s economy. If you’ve ever wondered why some people succeed in RE while others don’t, you HAVE to listen to this show. Chapters 00:00 Introduction to Real Estate Careers 02:44 Wyatt's Journey into Real Estate 05:25 The Difference Between Banks and Brokerages 08:05 Understanding the Brokerage Model 10:53 Choosing Between Retail Lending and Brokerage 13:48 The W2 Mindset vs. 1099 Mindset 16:29 The Spectrum of Comfort and Profit 19:18 Responsibility and Opportunity in Real Estate 22:21 Lessons from the Hard Road 25:09 The Value of Skill Over Niceness 32:05 The Value of Tough Love in Professionalism 35:01 The Balance Between Kindness and Effectiveness 37:02 Taking Responsibility in Leadership 37:49 The Importance of Accountability in Teams 39:53 The Spectrum of Agency in Individuals 42:36 The Role of Tough Love in Personal Growth 46:16 Becoming the Right Fit for Success 49:46 Investing in Yourself for Future Gains 52:53 The Mindset Shift from Entitlement to Contribution
Transcript
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| 0:00.0 | What's going on, everyone. Welcome to Real Talk, Real Estate. I'm David Green, and this is the David Green Show. |
| 0:06.7 | And I've got an interesting show for everybody today. This is not going to be a seeing green. It's actually going to be a seeing Wyatt. |
| 0:14.6 | For years, I've wanted to do a show on what it's like to be a real estate professional, real estate agents, real estate |
| 0:21.2 | brokerage, loan officers, contractors, people that work in our space, but they don't necessarily |
| 0:26.8 | own the properties. And I think with the way that the market has shifted, you're really in a |
| 0:32.4 | better position if you hate your W2 to take a job within real estate rather than trying to live off the cash flow |
| 0:39.3 | from real estate. And I know that's a bit of a controversial take. I've ruffled quite a few feathers |
| 0:44.7 | over the years by making that statement, but I stand by it. For years, I told people, I think you |
| 0:49.3 | should keep your W2 unless you're absolutely crushing it, flipping houses houses or using the birth strategy to scale a |
| 0:57.8 | portfolio and the people that sell courses to try to get you out of the rat race don't like me saying |
| 1:03.2 | that well rather than going head to head with them and just being two goats ramming into each |
| 1:09.2 | other i thought i would bring you one of the employees |
| 1:11.5 | from the one brokerage. I'm joined today by Wyatt Wolf, who not only has a super cool name, |
| 1:16.7 | he's got a very cool story as well. And rather than talking about how somebody built up their |
| 1:21.0 | real estate portfolio, we're going to talk about how this person built up an income working in |
| 1:26.9 | real estate. And then we'll get into if they invest |
| 1:29.3 | some of that money into real estate and what their plans are in that regard i think this is giving |
| 1:34.0 | me an interesting show for anybody who's out there who's thought about what it would be like to work |
| 1:38.4 | in real estate rather than just invest in real estate maybe do both i cover this in my book better |
| 1:43.6 | than cash flow the 10 ways you make money in real estate and this is both. I cover this in my book, Better Than Cashflow, The Ten Ways You Make Money in Real Estate. And this is the bonus one. This is the 11th way. That's actually working in real estate. So if you guys would like to read what I think is the best book I've ever put together, you can find that one on Amazon. Now, Wyatt, welcome to the show. Thanks for having me. Yeah. Now, everyone should know, White had no idea that we were going to talk about this. We have another show we're going to record right afterwards about what he's doing at the one brokerage and ways that he's saving people money that you may not know about. I think that'll be really good. So if you like Wyatt's story, make sure you check out that episode also. But this would be a surprise to both he and I, because I don't know his origin |
| 2:18.6 | story. And he wasn't preparing to talk about it. So I kind of like this idea. It's a cool |
| 2:23.8 | show. Let's start off with talking about what you were doing before you were working in the loan |
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