Podcast Summary: Real Estate Investing School Podcast

Episode 119: Knocking Doors to Own Doors with Zach Winter

Release Date: January 1, 2024
Host: Joe Jensen
Guest: Zach Winter

Episode Overview

In this episode, Joe Jensen talks with real estate investor and door-to-door salesman Zach Winter about his transition from sales into building a real estate portfolio of 16 properties in just a few years. Zach shares the mindset shifts, disciplined habits, and actionable strategies that allowed him to move from learning to execution—plus candid, hard-learned lessons along the way, including expensive missteps and the reality behind taking legal action. The conversation is practical, encouraging, and offers a detailed look at how consistency and clarity lead to investing success.

Key Discussion Points & Insights

1. How Door-to-Door Sales Led to Real Estate Investing

• Personal Growth in Sales: Zach credits the door-to-door industry not just for financial opportunity, but for encouraging personal and financial growth outside the job. Seminars and coaching led him to explore how others were growing their income.
• Real Estate as a Tangible Path: Unlike stocks or 401ks, Zach was drawn to real estate because it offered something "real, physical, tangible" and felt safer and more reliable.
  • Quote: "People are always going to rent, especially right now, and it's something you buy that you can actually go see, touch, feel. For me, that always made sense." – Zach (02:25)

2. Safety, Scalability, and Customization in Real Estate

• Both Joe and Zach highlight the safety of buy-and-hold real estate ("landlording stuff"), comparing it favorably against the volatility of stock markets.
• Real estate offers scalable risk—investors can choose their comfort level and ramp up as their portfolios and experience grow.
  • Quote: "You can really choose where you want to be. I'll lean towards the lower risk long term, but if I get an itch to do a little more, higher return, higher risk deal, it's definitely available." – Zach (05:47)

3. From Learning to Execution: The First Investment

• Zach learned about real estate in 2015, but didn't buy his first property until 2019, despite having set up a dedicated savings account and consuming books and seminars.
  • He’d put 30% of every paycheck into a real estate fund for years before pulling the trigger.
• The main barrier? Execution.
  • Quote: "Execution is a skill set and it has to be practiced and learned." – Zach (08:38)
• Trigger to Take Action: After a record income year left him unfulfilled, Zach realized he needed assets to show for his work—this drove him to finally invest.
  • Quote: "What do I have to show for it?...I don't want to trade another year of my life just to recreate that." – Zach (10:12)

4. Systems and Habits: Setting Up for Success

• Budgeting Method: Zach splits his income into designated bank accounts: expenses, taxes, real estate, rainy day fund, and even a ‘toy’ account for discretionary/luxury spending.
  • He stresses the importance of automatic, intentional allocation:
    • Quote: "If the money's not already allocated before it hits your account...the money's gonna get spent." – Zach (13:49)
  • This allows him to always be ready for the next deal: "I look at my bank account every day...When can I get that next property?" (12:23)

5. Buying Out of State & Building a Portfolio

• Zach's first purchase was in Tulsa, Oklahoma, while living in Texas, via an agent/property manager recommended by a trusted friend.
• After the first deal, rapid "rinse and repeat" growth followed—he emphasizes the momentum gained from the initial execution:
  • Quote: "Once you execute once, the floodgates open. Then, momentum is key." – Zach (18:01)
• Most deals were similar turnkey out-of-state single-family rentals.

6. Analysis Paralysis and Learning by Doing

• Zach admits to being "slightly analytical," often over-analyzing before his first deal. Now, he learns by action, not fearing to ask basic questions after closing a deal.
  • Quote: "90% of all the knowledge I have on real estate has come by just doing it." – Zach (19:28)
• Joe emphasizes: "Just not being afraid to look stupid. That's how you're gonna learn." (20:30)

7. Deal Analysis: Zach's "Buy Box"

• Zach’s goal is currently cash flow, not equity or appreciation. He seeks properties with 10%+ cash-on-cash return in decent locations; long-term appreciation is a bonus, not the focus.
  • Quote: "For me, I want liquid, usable money right now in order to continue to buy." – Zach (25:10)
• Stresses the importance of focus and clear personal goals—what Joe calls "blinders"—to avoid analysis paralysis.

8. Execution as a Skill (MM:27:40)

• Zach views execution as a muscle built through small consistent actions (setting up accounts, directing automatic savings) rather than giant leaps.
  • Quote: "The art of execution is something that's...one bite at a time, little by little." – Zach (27:56)
• Opportunities become visible and actionable only when you’re prepared ("If you're ready, you'll open the door. If you're not, you won't even know someone's there." – Zach (31:40))

9. Real-World Challenges: Lawsuits & Losses

• Zach describes a year-long lawsuit when a seller attempted to back out of selling two out of five bundled properties, despite having accepted separate contracts for each due to inspection contingencies.
• Outcome: He received the properties but at a cost:
  • $38,000 in attorney fees with only $2,500 reimbursed.
  • Had to close at a much higher interest rate due to year-long delays (original 5.85% up to 8.125%).
  • Quote: "No one won. The attorneys won." – Zach (43:09)
  • Lesson: Litigation should be the absolute last resort; Zach would avoid it if possible in the future.

10. Expensive Mistakes & HOA Warnings

• Zach warns against ignoring HOA rules and over-improving in lower median areas:
  • Bought a $549K home in a Wichita, KS community above median value, with an HOA that prohibits all rentals.
  • Now sits empty, costing money with no chance to rent it out.
• Takeaway: Always read HOA CCNRs (Covenants, Conditions, Restrictions), never assume rental is allowed even after owner-occupancy, and avoid over-improving for the area.
  • Quote: "Read your HOA policies. It is not a joke." – Joe (54:26)

Notable Quotes

• "Execution is a skill set and it has to be practiced and learned." – Zach (08:38)
• "If the money's not already allocated before it hits your account...the money's gonna get spent." – Zach (13:49)
• "Once you execute once, the floodgates open. Then, momentum is key." – Zach (18:01)
• "The art of execution is something that's...one bite at a time, little by little." – Zach (27:56)
• "If you're ready, you'll open the door. If you're not, you won't even know someone's there." – Zach (31:40)
• “No one won. The attorneys won.” – Zach (43:09)

Memorable Moments & Timestamps

• [02:25] Zach’s epiphany about the tangibility and safety of real estate
• [10:12] Realization after a big income year: “What do I have to show for it?”
• [13:48–15:10] Zach’s detailed breakdown of his multiple account budgeting system
• [18:01] The power of momentum after the first deal
• [25:10–26:43] Deep dive into the importance of having a focused buy box and ignoring distractions
• [37:56–43:00] The real cost and emotional toll of a year-long real estate lawsuit
• [53:34–56:01] The story of buying above the median and HOA nightmare—expensive lessons

Final Four Questions – Zach’s Answers

1. Dream Deal ([46:38]): A 40+ unit apartment complex—Zach’s goal is to eventually scale up to large multifamily, inspired by Grant Cardone’s jump into bigger properties.
2. Most Pivotal Books ([47:59]):
   • The Slight Edge by Jeff Olson: Helped him internalize the power of small, consistent actions.
   • As a Man Thinketh by James Allen: For mindset and discipline.
3. Most Expensive/Interesting Mistake ([53:30–56:01]): Buying an over-improved home in a low-median area, only to be stuck because the HOA prohibits all renting. Emphasizes reading HOA policies.
4. Purpose of Life ([57:05]): To be the absolute best version of oneself in all areas—relationships, health, wisdom—not just material success.
   • Quote: “I think the most joy comes out of doing hard things.” – Zach (59:39)

Connect with Zach Winter

• Facebook: Zach Aaron Winter
• Instagram: @thezachwinter

Key Takeaways

• Start with small, executable actions; don’t wait for perfect knowledge.
• Have laser focus on your current real estate goal—blinders help you avoid inaction and distractions.
• Allocate investment funds intentionally and automatically before you get paid.
• Vet your team (especially out-of-state agents/property managers) and lean on referrals.
• Always read and understand HOA rules before buying.
• Litigation is costly; avoid lawsuits unless every other option is exhausted.
• Execution is the key differentiator—build the skill by practicing action in small steps.
• Success in real estate is about building your empire, not just someone else’s company.

This summary captures the essential lessons, real-world stories, and practical advice found in the episode. Whether you’re just getting started or want a behind-the-scenes look at the mindset and methods of a fast-scaling investor, Zach’s candid approach and Joe’s coaching insights make this a valuable listen or read.