The David Greene Show — Episode 109 Summary

From Fast Growth to Total Crash: A Real Estate Comeback Story

Podcast: The David Greene Show
Host: David Greene
Guest: Amy Dills, Minnesota Broker
Date: January 18, 2026

Episode Overview

This episode dives into the roller-coaster career of Amy Dills, a Minnesota real estate broker whose journey spans rapid early success, a business-killing crash, and a resilient comeback. Amy and David strip away the fluff, candidly exploring building wealth, creating momentum, managing risk, the realities of brokerages and teams, and how partnerships and mentorships work in the industry.

Key Discussion Points & Insights

1. Amy’s Entry Into Real Estate

• Amy recounts graduating in 2010, pregnant, uninsured, and motivated by the $8,000 Obama-era tax credit for first-time homebuyers.
• Early bad experiences with agents prompted her to get licensed:

  “If that dinkus can do it, so can I. And that owning where you live is the single most important foundation to wealth building.” (Amy, 03:11)

• Bought a fixer HUD home with an FHA 203k, learned on her feet, pocketed $13,000 when selling after three years—more than she’d ever had.

2. The Importance of Homeownership for Wealth

• Amy and David agree that owning your residence builds financial control, equity, and steady confidence through DIY projects and repairs.
• Emotional benefits: each completed task builds “mastery and ownership.” (Amy, 06:51)
• David ties this to a broader principle:

  “You’re supposed to suck. You don’t know anything when you start... Your goal is to build momentum and confidence.” (David, 08:38)

3. Investing vs. Agent Work: False Dichotomy

• Amy cautions investors not to get licensed just for MLS access—market knowledge and deal flow are the true edge.
• “If you’re just like, I just want to get the MLS and save myself on commissions, I think you’re going to ultimately end up not getting your home sold as effectively and efficiently.” (Amy, 13:40)
• Both agree that specialization yields better returns—and that professionals should expect to pay for expertise.

4. Rapid Growth: The Thrill and the Pitfalls

• Amy built a successful solo practice, then her own brokerage, which ballooned to 20+ agents during the pandemic.
• Highlight of leading, learning, and winning together:

  “Some of my favorite years in real estate… it’s not giving me that thrill of the chase that I was getting before. I found for myself that I get that more when I get to see my agents winning.” (Amy, 20:08)

• But as growth compounded, problems did too: cliques, COVID disrupting in-person culture, and Amy getting overextended with multiple major projects.

5. The Crash: Overextension and Market Shift

• 2022–2023: Rising rates, project delays, and lender pullouts caused a perfect storm; Amy's business, finances, and even personal home projects were all threatened.

• “I cannot do everything well at the same time… it was like the biggest, best learning thing that has ever happened to me.” (Amy, 22:23)

• Lessons learned: necessity of reserves, focusing on fewer projects, and preparing mentally/financially for sudden market shifts.

[Key Segment: The Crash Begins: 22:00–29:20]

6. Rebuilding: Cautious Growth and Partnerships

• Having “burned it down,” Amy focused on stabilizing her finances, then shifted toward partnership models—both in investing and on her real estate team.
• Amy now prioritizes collaboration and leverage, learning that shared risk and support is more sustainable and rewarding.

7. Partnerships and Mentorships: Winning Formulas

For the Junior Partner:

• Show up, follow through, ask for help—don't expect trust or leads by default.
• Trust builds through small, reliable actions:

  “You have to be the person that shows up. What can I do? …And then you actually go do it.” (Amy, 33:40)

For the Senior/Alpha Partner:

• Expect only a minority of agents to truly commit—so pour energy into those who take initiative.
• Meet new agents where they are, not where you want them to be.

• “Let’s see where you are… one little thing to work on until you got it. Then we add it up. It’s the same as that stacking small wins with homeownership.” (Amy, 50:39)

8. Market Realities & Agent Mindsets

• David criticizes “body shop” brokerages that sell the dream but offer little true support, fueling entitlement and churn.
• Agents and teams, both say, must face the work honestly:
  • “Go find the business, serve your clients well, and sharpen the ax—and do them all, every week, to win.” (Amy, 40:15)
• Both host and guest are blunt about the poor outcomes for agents acting entitled or relying on handouts rather than skill-building and genuine service.

Notable Quotes & Memorable Moments

• Momentum & Confidence:
  • “You’re supposed to suck... Your goal is to build momentum and confidence.” (David, 08:38)
• On Overextension:
  • “While I can do anything, I cannot do everything well at the same time.” (Amy, 22:31)
• Reality Check for New Agents:
  • “You have three jobs as a real estate agent… find the business, serve well, sharpen the ax.” (Amy, 40:15)
• Partnership Wisdom:
  • “If you expect that 30% of real estate agents are never going to do anything... it gets easier because you’re just like, ‘oh, okay, you’re in the 30%.’” (Amy, 46:05)
• Mentoring and Loyalty:
  • “It’s that unscalable, human—be a person—thing… the more you can lift people up with you, the rising tide lifts all the boats.” (Amy, 54:00)

Timestamps: Important Segments

| Timestamp | Topic / Moment | |-----------|--------------------------------------------------| | 02:40 | Amy’s first home purchase story | | 05:27 | Emotional impact and empowerment via ownership | | 10:20 | Getting into sales—building momentum | | 13:01 | Investor vs. Agent roles | | 17:55 | Working with (and outsmarting) undertrained agents | | 19:29 | Building a team and the thrill of leadership | | 22:23 | The crash: overextension and market turn | | 25:45 | Market psychology and how everything crashed | | 33:35 | Partnership roles and establishing trust | | 40:06 | Reality of real estate work and expectations | | 46:05 | Leading a team—understanding agent ratios | | 54:00 | The “unscalable human thing” builds loyalty | | 57:49 | Jocko’s decentralized command & practical mentoring | | 59:03 | Where to find Amy and her brokerage (Brick & Banister) |

Summary: Takeaways for Listeners

• Growth is nonlinear: Success often gives a false sense of security; market shifts are sudden and unforgiving.
• Specialize, but collaborate: Being an expert, working with pros, and leveraging partnerships bring better results than going it alone.
• Momentum generates confidence: Each small win—owning your home, closing a deal, helping a team member—fuels your climb.
• Reality beats fantasy: Cut through the “passive income” hype; winning in real estate takes relentless activity, skill-building, and serving others.
• Mentorship and community matter: True learning happens in relationship—meet people where they are, help them rise, and loyalty will follow.

Connect with Amy Dills

• Website: brickandbanister.com
• Instagram: @amy_renae
  (“Usually digging in the dirt, playing with poultry, or running my mouth.”)

A must-listen for agents, investors, or anyone determined to build wealth or a business—full of practical, hard-earned wisdom.