The David Greene Show – Episode 91
Title: Seeing Greene with Wyatt Wolff
Date: October 23, 2025
Host: David Greene
Guest: Wyatt Wolff, Loan Officer at The One Brokerage
Episode Overview
In this episode, David Greene shifts gears from his usual “Seeing Greene” format to interview Wyatt Wolff, a key team member at The One Brokerage. Instead of diving into property ownership, David and Wyatt offer an unvarnished look at what it’s like to work in the real estate industry, focusing especially on service roles such as agents, brokers, loan officers, and contractors. Together, they delve into career-building advice, reveal the often-misunderstood differences between retail and brokerage lending, and explore the mindset required to thrive in the 1099 world versus the W2 mold. The conversation is packed with practical insights about work ethic, opportunity, responsibility, and the path to truly leveling up your real estate game—on or off the ownership side.
Main Themes:
- Career opportunities in real estate beyond investing
- The grind mentality vs. comfort-seeking
- Transitioning from W2 to 1099 and building real skills
- Choosing between bank and brokerage careers
- Investing in yourself and “embracing the suck”
Key Discussion Points & Insights
1. Wyatt’s Work Story – From College Dropout to Loan Officer
[02:30–06:40]
- Wyatt shares how he intentionally avoided student loan debt, choosing to work full-time through community college.
- Noted that he was “making more than my professor” and realized the value of working hard in blue-collar production roles.
- Jumped into real estate thanks to a friend in mortgages—and was drawn in by a curiosity for the “sausage-making” behind-the-scenes.
- Maintained multiple jobs for years: “For years I actually worked two jobs. I worked at night at the distribution center and I worked mortgages during the day... Thankfully I didn’t [quit] because mortgages fell off a cliff.” [04:42]
- Advice for young listeners: “Put your, your, your head down and just grind. Take the jobs that people don’t want to take. Work hard and make the money.” [05:18]
Notable Quote:
“Opportunity lies where responsibility has been abdicated.” — Wyatt, [05:18] (citing Jordan Peterson)
2. Bank vs. Brokerage: The Loan Officer’s Perspective
[08:09–13:24]
- Banks operate with a narrow “buy box”; fewer programs, less creativity:
“If you don’t come back next year. And that’s pretty much the only lever that they can pull to make things work.” — Wyatt, [08:59]
- Brokers can shop multiple lenders and programs, seeking creative solutions:
“I don’t think we have lost a deal yet for something that was just impossible to do. There’s always a way to do it.” — Wyatt, [08:59] David recounts frustration with traditional banks and his “aha moment” discovering the broker model:
“I hated loan officers, I hated bankers... Then I learned about this brokerage idea, where they would take my information and go do the shopping for me.” — David, [09:16]
3. Who Should Jump into Brokerage?
[13:24–16:34]
- Wyatt: The best path depends on personality.
- Brokerage: For those “who want to jump off a cliff and build an airplane on the way down,” who thrive on information and rapid learning.
- Bank/Retail: Suits people looking for structure, routine, and regimented training.
- David: Brokers tend to attract those hungry for information (i.e., likely podcast listeners).
Summary:
If you crave structure, go retail. If you want aggressive growth, pursue the broker path.
4. The W2 Mindset vs. the 1099 World
[16:34–24:20]
- David: “W2 is the biggest scam in the history of the world in the favor of the person working the W2. Because you can camp out... and do the bare minimum work... In this world, it’s not like that. The people who work harder, who get after it, make more.” [16:34]
- Most real estate agents (and many investors) fail because they expect to be rewarded for merely “existing in a workspace.”
- The comfort-profit spectrum: “You can’t try to pick the best from every single strategy and throw them all into the one super deal, which is what a lot of people work.” — David, [17:18]
- Real estate, like house hacking, is a balancing act between comfort and profit—the more discomfort you’re willing to accept, the more profit you unlock.
5. Embracing Responsibility, Not Running from It
[24:20–28:24]
- David observes people constantly chase the “easy button” in real estate: from cash flow, to BRRRR, to short/mid term rentals, to creative finance—always seeking the next shortcut.
“Everybody is usually rushing to what they perceive as the easiest way to make the most money.” — David, [24:25]
- Easy strategies rarely last; lasting opportunity lies where others won’t take responsibility.
- Broader point: This habit isn’t just in real estate—responsibility aversion is why society avoids marriage, children, or any hard path.
6. Life Lessons: The Hard Way Is the Easy Way
[28:24–30:02]
-
Wyatt: “One of the things I’ve learned as I’ve gotten older is the hard way is actually the easy way. Everybody spends so much energy trying to find...what’s the easiest way...? They try and over-optimize. When in reality...you just need to be effective.” [28:54]
Notable Quote:
“The hard way is actually the easy way, and people just kind of forgot that.” — Wyatt, [28:56] -
David: “Choose your hard.” There’s always a hard—now or later.
7. What Actually Creates Value? The Myth of Niceness vs. Effectiveness
[34:00–39:09]
- Valuable employees and partners are those who own problems and take responsibility, even if it means being “not nice” to get things done.
- David’s orthopedic surgery parable: society rewards “nice,” but skill and effectiveness matter most when the stakes are real.
“That doctor was more useful to society at large as a jerk than the nice person was that was comfortable.” — David, [34:55]
- Wyatt: There's a difference between being nice/kind and being effective:
“If you’re super polite...but you have the effectiveness of a wet noodle, that doesn’t help anybody.” — Wyatt, [36:18]
- True leadership: Give your team credit for victories, but take full responsibility for mistakes.
8. The Growth Mindset: Become the Person That Opportunity Seeks
[49:00–53:37]
- Don’t chase results. Chase being the kind of person worth results.
“Focus more on being the type of person that gets paid a lot because they’re so effective—not, ‘I want to make a lot of money.’ There’s a difference.” — Wyatt, [49:00]
- Wyatt’s marriage/relationship and career advice:
- “Faith is doing the work and just knowing that the result will come. Focus on the work, not the result. If you just put one foot in front of the other, eventually you’ll get where you need to go.” — Wyatt, [53:10]
- The same principle applies to learning loan programs, fitness, etc.
9. Invest in Yourself First; The Universe Will Respond
[58:24–60:28]
- Wyatt invests in coaching (out-of-pocket), seeing it as “an investment, not a cost.”
- The best opportunities—jobs, relationships, clients—come when you are already valuable.
- David: “Why should David invest in me if I don’t invest in me? ... You have to start that. You have to be the one that takes yourself seriously.” [60:10]
10. Real-World Examples & Takeaways
[60:28–67:51]
- Both David and Wyatt share stories of “doing the hard work nobody wanted,” which paradoxically led to promotions, opportunities, and relationships.
- David: "I wanted to work for free all the time. And then I just learned more than everyone else did. And then I had a lot of confidence...” [63:05]
Notable Quotes & Memorable Moments
On Embracing Hard Things
“The work is working on you just as much as you are working on it.” — Wyatt, [64:33]
On Skill & Effectiveness
“Be the type of person that deserves those things because you put the work in…” — Wyatt, [51:00]
On Opportunity
“Opportunity lies where responsibility has been abdicated.” — Wyatt (citing Jordan Peterson), [05:18]
On Why Most Don’t Succeed
“Most agents…do not succeed because they have the W2 mindset.” — David, [17:18]
On True Leadership & Accountability
“If my team messes something up, I’m responsible. If I mess something up, I’m responsible. If something good happens, my team is responsible.” — Wyatt, [37:29]
On Getting Results
“You’ll learn more from 2 months of action than you will from 2 years of listening.” — Wyatt, [66:43]
Timestamps for Key Segments
| Timestamp | Discussion Topic | |-----------|-----------------------------| | [02:00] | Wyatt’s career background & entering real estate | | [04:42] | Working multiple jobs, lessons for young workers | | [08:09] | Bank vs. brokerage roles | | [14:57] | Who should work at a bank vs. broker | | [17:18] | The W2 mindset’s dangers in real estate | | [24:20] | Responsibility as the source of true opportunity | | [28:54] | “The hard way is the easy way” message | | [36:18] | The myth of niceness vs. real value | | [49:00] | Personal growth: become the person, not just seek reward | | [58:28] | Investing in yourself: coaching and learning | | [64:33] | Final advice: embrace the suck, work is working on you |
Final Practical Advice
- Start now: “The best time to start was yesterday. The next-best time is now.” — Wyatt, [65:11]
- Embrace discomfort: “The harder the work, the more you’re going to get out of it.”
- Invest in yourself: Training, education, and curiosity always pay back even if it feels slow at first.
- Seek responsibility: When others shy away, lean in—opportunity grows in the hard places.
- Don’t chase leads or results—chase becoming the person who naturally attracts them.
How to Connect with Wyatt
“Shoot me an email: wyatt@theonebrokerage.com. That’s Wyatt with two t’s—W Y A T T at the one brokerage dot com (one is spelled out).” — Wyatt, [67:51]
For more, check out future episodes with Wyatt on The David Greene Show.
Want to work at The One Brokerage or explore a real estate career? Visit: davidgreene24.com
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