5 Year Monthly Real Estate Coaching Series by Greg Pinneo

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A sustainable real estate career isn’t built in weekend sprints. It’s forged over years—through cycles, deals, mistakes, and wins—guided by a mentor who has lived it. The 5 Year Monthly Real Estate Coaching Series by Greg Pinneo offers exactly that: a structured, long-horizon curriculum that compounds your skills month after month, so your judgment, deal flow, and life design grow together.

Overview this course

This is a five-year, $1,800 program built around monthly, deep-dive audio sessions. Each month, Greg Pinneo selects an investing topic—finance, risk, legal tools, negotiations, deal structure, tax strategy, or mindset—and explores it thoroughly. The result is a living library that meets you at every stage of your journey, from your first single-family offer to complex multiplex due diligence, creative finance, equity sharing, options, notes, and tax-efficient exits.

The format is intentionally simple: listen, reflect, apply. Put the sessions on during your commute or while walking properties. Revisit each module annually. The repetition is the point: the same concept, heard at different levels of experience, reveals new layers. Students often report that things “click” on the second or third pass because Greg doesn’t skim—he dissects.

What you’re getting is more than tactics. It’s a way of thinking: how to frame risk, evaluate time, negotiate from strength, and design a portfolio that fits your life, not the other way around. For additional momentum, you’re encouraged to attend Greg’s live events; the audios lay the foundation, and in-person training sharpens the edge.

Why should you choose this course?

Depth over hype. Many programs promise quick wins. This series builds durable competence—deal by deal, year by year—so you can operate with confidence across markets.

One mentor, consistent philosophy. You’ll follow a coherent playbook instead of piecing together conflicting advice from random sources. That consistency reduces decision fatigue and speeds execution.

Monthly cadence = compounding mastery. A manageable, recurring learning rhythm ensures you’re always improving—without sacrificing your business or family time.

Breadth that matches real life. Real estate is multidisciplinary. A typical year here spans negotiations, due diligence, small multifamily, 1031 exchanges, lending, options, raw land, specialty leasing, condo conversions, notes, green building, and more—plus the inner game: mindset, time management, and leadership.

Audio-first flexibility. Because the lessons are delivered as audios, you can learn while driving, traveling, or walking a property—no need to block out full days for study.

From philosophy to fieldwork. The series ties timeless principles (risk, leverage, substitution of collateral, balanced success) directly to practical walkthroughs (single-family and multiplex pre-purchase, agent relationships, attorney review), so nothing stays abstract for long.

What You’ll Learn

Across five years of monthly sessions, you’ll build a toolbox that’s both broad and sharp. Below is a snapshot of the ground you’ll cover, organized thematically to keep your SEO-friendly overview easy to scan.

Foundations that Never Expire

• Time, focus, and operating cadence: Pin down a time-management system that actually survives deal season.

• Risk literacy: Understand substitution of security, buffers, and downside planning; learn to structure deals that protect your future self.

• Capital mindset: “Show me the money” becomes a process—who funds what, why they say yes, and how to present your ask credibly in minutes, not hours.

• Two ledgers of life: The habit stack that keeps health, relationships, and wealth compounding together.

Acquisition & Due Diligence

• Offer architecture: Write offers subject to feasibility; sequence contingencies to uncover truth early; use options when speed or uncertainty is high.

• Walkthroughs that matter: Single-family and multiplex pre-purchase frameworks—what to touch, test, and photograph; how to rank red flags.

• Working with agents: Turn agents into partners, not gatekeepers; scripts for clarity, speed, and professional respect.

• Attorney review: Build an annual legal tune-up; know when to escalate and how to prep counsel efficiently.

Property Types & Playbooks

• Small multifamily: Why 2–20 units is the “skill-building sweet spot” for many operators.

• Condos & conversions: Where value is created (or destroyed) in the docs, budgets, and boards.

• Raw land: Utilities, access, zoning, and “work backward from exit” underwriting.

• Specialty uses: From Beds-for-Meds to shared spaces—align operations with demand drivers, not decor.

Finance & Deal Structure

• Creative finance: All-inclusive trust deeds, substitutions, seller carry, wraps—how to align incentives so everyone sleeps at night.

• Options & equitable interests: Secure control without overcommitting capital; manage reputational risk with professional follow-through.

• Note buying & private lending: Become the bank; discount logic, collateral assessment, and servicing realities.

• 1031 exchanges: Timelines, identification strategies, and pitfalls that trip up first-timers.

Operating, Scaling & Systems

• Marketing for results: Relationship-driven lead gen; why consistent follow-up outperforms sporadic blitzes.

• Client/tenant experience: The simple seven for retention and referrals; when to hire help (and what to hand off first).

• Cash-flow levers: Expense discipline, rent strategy, and maintenance calendars that prevent “surprise” CapEx.

• Data and taxes: Coordinate with your CPA; make your taxes easier through smarter record-keeping and entity hygiene.

Mindset, Leadership & Longevity

• Balanced success: Keep the portfolio growing without shrinking your life.

• Confidence & courage: How to be daring yet disciplined; lessons from mentors and case studies that anchor conviction.

• Adversity & resets: When markets shift, how to reframe, retool, and move—without panic.

• Passing the baton: Build teams, partners, and successors so your results outlive your calendar.

Representative Monthly Topics You’ll Encounter

• Time management, buy-and-flip vs. keep-and-refi, CPA insights, small multifamily, risk, substitution of security.

• All-inclusive trust deeds, feasibility studies, partnerships, changing-market opportunities, short sales, options, out-of-state buying.

• 1031 exchanges, attorney review, equity sharing, marketing with intent, specialty leasing, note buying, raw land, green building.

• Mortgage world, working with agents, condo conversions, the three-plan formula, beds-for-meds, retirement planning, perspective from the peak.

(Over the full five years you’ll access dozens of these deep dives; a handful of historical volumes are noted as damaged in the original archive, but the breadth remains extensive.)

How to Get the Most from the Series

• Listen with purpose: Treat each month like a mini-semester. Capture three takeaways and one action per session.

• Build a deal lab: Apply one tool (e.g., feasibility addendum, option, or broker briefing) to a real opportunity within 30 days.

• Stack your support: Share your notes with your CPA, attorney, or agent to tighten your execution loop.

• Revisit annually: Concepts like risk, leverage, and offer structure mature as your portfolio grows—expect different insights on pass two and three.

• Pair with live training: When possible, attend a live event to workshop nuances, expand your network, and accelerate implementation.

Who Should Take This Course?

1. Serious beginners who want a grounded, multi-year education instead of piecemeal hacks.

2. Intermediate investors ready to evolve from “deal chaser” to disciplined operator—especially in small multifamily and creative finance.

3. Busy professionals (physicians, executives, military, entrepreneurs) who need an audio-first format that fits real schedules.

4. Out-of-state buyers who require systems for agent management, underwriting discipline, and remote due diligence.

5. DIY landlords turning pro who want to graduate from transactional thinking to portfolio strategy.

6. Lenders and note buyers seeking a street-level view of collateral, risk, and repayment behavior.

7. Lifelong learners who appreciate philosophy with their spreadsheets—because how you think determines how you deal.

If you value clarity, consistency, and compounding skill, this series is engineered for you.

Conclusion

Real estate rewards the prepared—the investor who understands risk, frames offers intelligently, nurtures relationships, and keeps improving through cycles. The 5 Year Monthly Real Estate Coaching Series by Greg Pinneo is your long-form operating system: one mentor, one philosophy, delivered in monthly, digestible masterclasses that sharpen your edge and widen your opportunity set. If you’re ready to trade scattered tactics for a coherent, multi-year path, this is a smart, time-tested choice.

Make the next five years count—start listening this month, take one meaningful action per session, and let steady mastery compound into better deals, better decisions, and a better life.