The Massimo Show

Hosted by Rod Santomassimo

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100

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Oct 2026

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About the show

Over the last 10 plus years, the Massimo Group has had the privilege of working with thousands of professional entrepreneurs and solopreneurs most of whom wish to attain either more margin in their life or financial margin in their future. More money and less time. The objective of the Massimo Show is not only to provide insights from top producers across the globe, but also to share personal and professional success trends from authors, thought leaders, and the like. Ideas to help you grow your personal practice. Welcome to The Massimo Show.

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60 recent

November 11, 2026Episode 12024 min

Episode 120 - Ultimate CRE Broker Business Plan

Overview Most CRE brokers set vague income goals with no idea how to reverse-engineer the daily activity required to hit them. Rod Santomassimo walks through a complete, math-driven business plan framework — starting with your income goal and working backwards through every conversion ratio until you land on a single, non-negotiable number: how many dials you need to make every week. Everything else flows from there. Key Takeaways Start with your income goal and work backwards — every target is derived from the math Average deal size is the most overlooked lever — bigger deals = fewer needed = better service Know your actual conversion ratios; guessing them is the most common planning mistake Time-compress your pipeline: meetings must happen early enough for deals to close by year-end 2–3 presence meetings per week with influencers is the highest-leverage activity in the plan Every dial is worth ~$260 — a voicemail isn't failure, it's part of the math The complete plan: income goal → deal size + commission + transactions → exclusives → meetings → conversations → dials

November 4, 2026Episode 1188 min

Episode 119 - The 4 Fears

Overview From brand-new agents to seven-figure producers, Rod Santomassimo has worked with thousands of CRE brokers across North America — and every single one faces the exact same four fears. In this episode, Rod names each fear, diagnoses why it holds brokers back, and delivers the cure: not willpower, not courage, but frameworks, systems, and clarity. Key Takeaways Every CRE broker — beginner to seven figures — faces these exact four fears Rejection is a filter, not a reflection of your worth or ability An empty pipeline creates the fear of prospecting — fill it with systems, not motivation Clients are loyal to expertise and insight, not to relationships alone Plateau is the sneakiest fear — it hits top performers hardest The cure for all four fears is the same: clarity, frameworks, and systems

October 28, 2026Episode 1188 min

Episode 118 - Qualifying Prospects

Overview Most CRE brokers have bloated pipelines full of low-quality deals that drain their time and degrade their service. Rod Santomassimo argues that the path to higher income isn't more deals — it's better deals. In this episode, he walks through a 9-point qualification checklist that top producers use to decide which clients and opportunities are worth their resources, and which ones to walk away from. Key Takeaways A bloated pipeline full of bad deals is worse than a lean pipeline of good ones Set a minimum commission threshold — and actually enforce it Every deal either builds your brand reputation or dilutes it — choose accordingly Cooperation and transparency from the client in discovery predicts how they'll behave at closing Know your service capacity and don't exceed it — quality of service drives referrals Apply this checklist to every deal currently in your pipeline — not just new ones

October 21, 2026Episode 11710 min

Episode 117 - Presence Pyramid

Overview Invisibility is a fate worse than failure in CRE. If your market doesn't know you exist, no amount of cold calling will ever be as efficient as it could be. The Presence Pyramid is a three-tier framework for building market awareness — from high-impact personal meetings at the top, to consistent physical marketing in the middle, to daily digital content at the foundation. Presence doesn't replace prospecting. It makes prospecting dramatically easier. Key Takeaways Invisibility is the enemy — being known in your market is a prerequisite, not a bonus Presence and prospecting are separate activities — both are required; neither replaces the other Tier 1 (personal meetings) has the highest impact per touch — protect those 2 slots per week Tier 2 (physical to top 100) creates monthly reminders that digital content cannot replicate Tier 3 (daily digital) is the foundation — it can and should be delegated at scale Content must always serve your audience, never promote yourself — the moment it becomes about you, it stops working Never assume you're posting too much — silence is the only thing that guarantees you stay invisible Ask every day: Who do I serve? How do I serve them? Let the answers drive every presence decision

October 14, 2026Episode 1169 min

Episode 116 - Pipeline Cheat Code

Overview Most CRE brokers manage their pipeline as a simple list — deals are either in or out. Rod Santomassimo introduces the Massimo Opportunity Matrix: a four-quadrant system that categorizes every deal by its stage AND your honest gut-level assessment of its likelihood to close. The result is a pipeline that tells you exactly what action to take on every deal, every week — and stops you from wasting energy on opportunities that will never pay out. Key Takeaways Every CRE broker — beginner to seven figures — faces these exact four fears Rejection is a filter, not a reflection of your worth or ability An empty pipeline creates the fear of prospecting — fill it with systems, not motivation Clients are loyal to expertise and insight, not to relationships alone Plateau is the sneakiest fear — it hits top performers hardest The cure for all four fears is the same: clarity, frameworks, and systems

October 7, 2026Episode 11514 min

Episode 115 - Massimo Matrix

Commodity brokers walk into a pitch and talk about themselves. Elite brokers walk in already understanding the full landscape of who makes the decision, who influences it, what issues are in play, and what the stakes are for every person at the table. The Massimo Matrix is the proprietary discovery framework that makes that possible — and it's the reason Massimo-trained brokers win exclusives that other brokers never see coming.

September 30, 2026Episode 11421 min

Episode 114 - Inactive Clients

The #1 source of income for CRE brokers is the phone call. The #2 source — and the one most brokers almost entirely ignore — is inactive clients. In this live workshop session, Rod Santomassimo breaks down why "past clients" don't exist, how commission leakage silently bleeds your income every year, and the simple three-question system that re-activates dormant relationships. During the recording, participants made live calls — and deals were uncovered in real time.

September 23, 2026Episode 11331 min

Episode 113 - CRE Broker Business Plan

Most CRE brokers set an income goal and then just work harder. The Massimo Business Plan framework does the opposite — it reverse-engineers from your financial goal down to the exact number of dials you need to make every single day. Once you understand this math, you stop guessing and start executing with precision. Everything comes down to a few key numbers, your ratios, and the discipline to protect your activity time. Key Takeaways Start with your income goal, average deal size, and commission rate — those three numbers tell you how many deals you need Work backwards through your conversion ratios to arrive at the exact number of dials per day you need to make If you don't track your ratios, you're guessing — and guessing is not a business plan Meeting-to-exclusive conversion below 25% means your pitch or offer isn't strong enough — fix that first Every dial is worth real money; knowing the dollar value of each activity changes your relationship with prospecting Presence activities (2–3 meetings/week, weekly top-100 marketing, daily social) aren't optional — they're the multiplier Never prospect without a presence; cold calls into a cold market are the hardest path The math doesn't lie — if you do the activity, the income follows

September 16, 2026Episode 1126 min

Episode 112 - The Four Ways

Every CRE broker has faced it — an owner who wants to sell or lease at a price completely disconnected from the market. Walk away and lose the opportunity. Take the listing and waste months going nowhere. Or use one of four specific strategies to bring them back to reality, win the exclusive, and ultimately create a commission opportunity while serving the owner's best interests. Your role is not to sell the property — it's to help the owner make the best possible decision for themselves. That's the educator mindset. Key Takeaways Determine sanity vs. vanity pricing before choosing your approach — emotional decisions need empathy first, data second Ask how they arrived at their price and how long they'll wait — motivation and timeline are your real leverage A short-term test period lets the market make your argument for you — and earns you a higher fee for the extra work Acknowledging the emotional investment before presenting data is what separates great brokers from commodity brokers Know your market numbers cold: days on market, number of offers, your exclusive track record — bring them to every conversation Cash flow projections at multiple price points make the cost of an unrealistic price tangible and personal Your job is to educate, not capitulate — the advisor mindset creates more commissions and better client outcomes

September 9, 2026Episode 11141 min

Episode 111 - 7 Days to Your Best CRE Year Yet

This is a live workshop session built around the Massimo Group's "7 Days" workbook — a structured year-end planning system every CRE broker should complete before January 1st. Over seven focused sessions, brokers review transactions, activities, clients, and mindset; identify what held them back; set financial and business goals; and lock in a refined plan going into the new year. The system works when you work the system. Key Takeaways Complete all 7 days before January 1st — reflection without a deadline is just wishful thinking Your conversion ratios tell you exactly where your business is leaking — fix the leak, not the symptom Inactive clients are not lost — they're uneducated; they need a reason to re-engage Name the specific mindset or discipline issue that held you back — vague restrictions never get fixed Your most productive activity should get more calendar, not less; your least productive should be cut Financial goals should be "smart but reach" — credible to you, ambitious enough to require real growth Your avatar defines everything — if your messaging speaks to everyone, it converts no one Qualification filters are non-negotiable; taking the wrong deal costs far more than the commission it pays