The David Greene Show with Jeremy Hunter | Episode 97

Date: November 14, 2025
Podcast: Real Talk Real Estate with David Greene
Guest: Jeremy Hunter (Property Manager, Colorado)

Episode Overview

David Greene welcomes Jeremy Hunter, a longtime real estate professional with experience as an agent, investor, and property manager in both Hawaii and Colorado. Together, they candidly unpack the realities of building a real estate business, how conference culture and mentorship have evolved, navigating market downturns and personal setbacks, the generational mindset shift in work ethic, and the sometimes uncomfortable truths about building real wealth over time.

The episode aims to demystify what it takes to succeed in real estate today—not through quick wins or viral social media strategies, but via thoughtful risk-taking, resilience in tough markets, practical advice for evaluating partners, and a grounded philosophy of “slow and steady” wealth-building.

Key Discussion Points & Insights

The Value of Real Estate Conferences & Education

• Conferences as Motivation, Not Revelation
  • Jeremy and David agree that while new investors are often overwhelmed with fresh info at conferences, experienced professionals usually find them repetitive—more about networking and recharging than learning something truly new.
  • David: “Real estate conferences are the Halloween costumes of the world… you get to dress however you want. No one’s going to judge you because it’s a costume, right?” (02:13)
• Rise of Free Content and Information Overload
  • The explosion of podcasts and online courses means you can get “conference-level” info all the time, but filtering good from bad is harder.
  • Jeremy: “Anyone can record a video or audio…and claim they know what they’re talking about and they don’t. So that’s scary.” (13:28)

Getting Started: From Humble Beginnings to Real Estate

• Jeremy’s interest in real estate began at age ten, noting the lifestyle difference between renters and owners:
  • “There was this kid down the street… I’m like, my landlord’s over… And he said, ‘Oh, no, my parents… they own their house.’…wow, they have nicer cars. They go on vacation… Maybe there’s something to this owning real estate thing.” (03:28)
• His professional path: auto mechanic → service advisor (meeting wealthy realtors at a Jaguar/Ferrari dealership in Honolulu) → real estate sales → property management.
• Early critical lesson: seeing that almost all wealthy clients owned real estate.

The Realities of Building Wealth with Real Estate

• Real Estate vs. Other Assets
  • Real estate’s unique edge: long-term inflation protection, ability to leverage via loans, and the chance to improve/value-add.
  • David: “Gold doesn’t pay you rent, and you can’t use loans to buy gold as easily as real estate, and you can’t improve gold. So real estate ends up being the thing for creative people.” (06:32)
• Surviving Downturns
  • Only a minority lost homes during the 2008 crash, but patience and responsible leverage pay off over the long run.
  • Jeremy: “At the peak… only about 5% of properties got foreclosed on… We don’t hear about all the people that bought… and 10, 15, 20 years later they’re golden—because they were patient and they were responsible.” (07:22)

Lessons from Painful Setbacks

• Financial Crisis and Personal Regrets
  • Jeremy’s candid about making big money young, lacking financial discipline, and the consequences in ’08-’09:
    • “When you take someone in their mid-20s who has never had money and doesn’t have a lot of financial literacy and starts making six figures, a lot of good—not a lot of good decisions are made.” (12:49)
    • After a short sale following an ARM reset: “I wasn’t being stupid. I just wasn’t educated, wasn’t prepared… By that time, I was doing a lot of things right...but you gotta keep more powder dry than you think sometimes.” (31:21, 32:16)
• Proactive but Powerless: Dealing with Banks
  • Jeremy details the infuriating bureaucracy trying to get a loan modification before falling behind:
    • “I’m like, hey, can we extend the rate? What are the options?… Well, until you’re 60 days behind on your mortgage, we can’t do anything for you... So totally against everything I believe…I stopped paying the mortgage for two months.” (35:03)
    • Ultimately, banks refused help, worse off than those who simply waited out the crisis or “camped” in the home without paying.

Advice on Picking the Right People to Learn From

• “I look at where they’re at and what they’ve accomplished… Who’s your property manager? Do they own properties? How do they manage theirs compared to yours?” (14:07)
• Property managers who are also investors themselves tend to “anticipate things going wrong, have solutions, already have the vendors…” vs. those who just build a business to rack up doors.

The Cost of Chasing Cheap Services

• Both in real estate sales and property management, “you get what you pay for.”
  • Hiring for lowest commission often yields subpar results—bad photos, little effort, poor marketing—ultimately costing far more.
  • David: “To save 1%, $7k, to lose $40k–50k, it doesn’t make sense.” (21:24)
  • Property management fee structures differ; beware of low-percentage fees offset by nickel-and-dime add-ons.

Building a Property Management Business: Jeremy’s Story

• Pivoted from sales to management in Hawaii, scaling from 0 to 500 doors in several years with a partner/mentor.
• Key drivers of growth:
  • Early adoption and deep use of property management software (“using every aspect of the software, not just scratching the surface”).
  • Building a referral reputation backed by refusing to poach sales clients from referring agents—even tagging them in the system.
  • Proactive business-building via local networking and offering real value estimates to sales agents (“Would you be interested in what this would rent for?”).

Mindset & Generational Work Ethic

• Both hosts reflect on changing times:
  • Previously, public service jobs (police, fire) were highly competitive; now cities “are begging” for applicants.
  • Skilled trades and mechanical work are stressed as lucrative, stable options for young adults willing to do hard work.
  • Today’s culture often fixates on “comfort first,” remote work, or seeking the highest pay for the least effort.
  • David: “You typically don’t find successful people that are addicted to comfort… Successful people are addicted to challenge.” (49:22)

Philosophies on Wealth, Risk, and Success

• No Easy Button: Wealth Is Slow and Boring
  • The repeated, sometimes “crotchety old man” message: Wealth comes from consistent, unsexy discipline—working hard, spending less than you make, investing the difference, and being patient.
  • Jeremy: “There’s no easy button anywhere. It doesn’t exist.” (76:04)
• Focus energy on the fundamentals, leverage the unique opportunities of youth and compound interest, and avoid getting caught up in hype around “the latest strategy.”
• Goal Setting and Knowing Yourself
  • Don’t just “wish” for results—decide what you actually want, make a specific plan, and hold yourself accountable.
  • Not everyone is wired to build massive enterprises like a Brandon Turner—consistent “base hits” over time can be a winning strategy.

The Changing Landscape: Technology, AI, and Trust

• Grassroots, referral-based networks remain powerful (“relationships… are always going to be important”), but online marketing skills do matter as well.
• As self-serve, automated, or AI-driven systems proliferate, authentic human connection—calling someone, sending a handwritten note—becomes a powerful differentiator (even causing people to question if a real phone call is a scam!).
• Jeremy: “Technology is a tool, not a replacement.” (66:07)

Notable Quotes & Memorable Moments

• “If you came to Vegas with me this last trip, you think Vegas is the funnest place in the world. I’ve been to Vegas a lot. That’s not normal. I feel like real estate is kind of the same for people that saw it five years ago. They think that’s just the way it is, and it’s not. That was the lucky night in Vegas. You may not see one again in your lifetime.”
  — Jeremy Hunter (09:34)

• “The best people I found were word of mouth referrals. The best contractors—someone’s like, hey man, I’m gonna whisper this name...this guy’s great.”
  — David Greene (61:30)

• "How wealthy you want to get depends on, well, how hard are you willing to work and how much are you willing to give up lifestyle for future benefit?"
  — Jeremy Hunter (75:12)

• “You gotta work, you gotta make money. If you want to get ahead, you gotta spend less money than you make, and you gotta invest the difference… then you gotta have patience and be smart with it over time.”
  — Jeremy Hunter (75:12)

• “If you want to be really successful, you’d be getting up early, working the two jobs, on the phone all the time. What most people actually want is to find a way to make a bunch of money without having to work hard…the number of people that come to me and say ‘I want to be successful’ vs. the people that actually do the work, even in my own company, is wildly different.”
  — David Greene (73:35–74:30)

Important Timestamps

• Conference Culture & Value: 00:46–03:28
• Jeremy’s Origin Story & Early Lessons: 03:28–08:35
• Real Estate Wealth: How/Why It Works: 06:32–10:53
• First Big Career Mistakes & the Financial Crisis: 11:14–33:34
• Advice on Vetting Agents/Managers: 14:07–21:24
• Building a PM Business—Growth Strategies: 56:07–61:30
• Mindset Shifts: Work Ethic Then and Now: 43:51–49:49
• Comfort vs. Challenge in Building Wealth: 49:22–76:05
• The Reality: No Easy Button, No Get-Rich-Quick: 75:12–76:51
• Using Tech to Enhance, not Replace, Relationships: 61:38–67:48

Closing Advice & Contact Info

• Jeremy’s Takeaway: “There’s no easy task. You’ve gotta do the things.” (79:23)
• Find Jeremy: ipmgj.com (includes links to his Instagram and more on property management).
• David’s Wrap-Up: Steady, consistent action outpaces get-rich-quick; aim to build a financial “fortress,” not chase the next trend.

If you want advice, real stories (not just the wins), or practical warnings about real estate, this episode is a must-listen. Both David and Jeremy keep the tone candid, occasionally irreverent, and always focused on what actually creates wealth and satisfaction in real estate long term.