The Massimo Show

Hosted by Rod Santomassimo

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100

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Aug 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

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

September 2, 2026Episode 11014 min

Episode 110 - Pain In The Ass

Most CRE brokers are afraid of being too persistent. Rod Santomassimo flips that fear on its head: if no one has ever called you a pain in the ass, you haven't come close to your potential. This episode breaks down the presence pyramid, the difference between marketing and prospecting, and why building a relentless personal brand in your market is the most reliable path to inbound business. Key Takeaways Marketing gets you known; prospecting gets you deals — you need both Identify your top 100 market influencers and get known by them systematically Use all three levels of the presence pyramid — personal, events, and digital Monthly physical touches (market reports, newsletters) to your top 100 are non-negotiable Build YOUR personal brand — not just your company's brand Post daily on social, email 2–3x per week, and always provide genuine value Being called a PITA isn't a failure — it's proof you're showing up more than everyone else

August 26, 2026Episode 11410 min

Episode 109 - Eight Asks

Most CRE brokers prospect in silos — they make calls, or they send emails, or they post on LinkedIn. Rod Santomassimo argues that single-channel prospecting is why most brokers plateau. The Eight Asks framework is a multi-touchpoint campaign system where every channel reinforces the others. The magic isn't in any one ask — it's in the campaign. Key Takeaways No single channel is a prospecting strategy — the campaign is the strategy Phone calls remain the #1 income driver for top CRE brokers, full stop Different asks work better for different demographics — know your audience You need 100 A-prospects and 300 B-prospects minimum to run a real campaign Outsource list research — never do $5/hour work yourself Combine all eight asks and your conversion ratios compound across every channel

August 19, 2026Episode 10614 min

Episode 108 - Easy Ways to Find Business

Finding business isn't hard — but finding the right business consistently requires two things most brokers never nail down: a crystal-clear picture of who they serve, and a specific, defensible answer to how they serve them. Rod Santomassimo walks through the three-part framework for finding business and shows how specificity in your positioning is the difference between struggling to get meetings and having prospects seek you out. Key Takeaways Every easy way to find business starts with knowing exactly who you're looking for Generic positioning kills deals before they start — specificity is your edge Demographics + psychographics + situation + stories = a complete avatar Know your clients' goals, fears, and frustrations before you walk in the door Use AI tools to research prospects and sharpen your avatar continuously Once you know who you serve and how, finding, attracting, and prospecting all get easier

August 12, 2026Episode 1076 min

Episode 107 - CRE Results Guarantee

Most CRE brokers ask for an exclusive and hope for the best. The Massimo Results Guarantee flips that dynamic — it's a specific, articulable guarantee you offer clients upfront that addresses their deepest concerns about hiring a broker: Will this work? What if it doesn't? In 17 years of coaching thousands of brokers, Rod has seen this one strategy increase conversion rates by 24–25%. The guarantee isn't just a sales tactic — it's a commitment you make to yourself first. It works when you do the work. Key Takeaways A results guarantee increases client conversion rates by 24–25% — it's one of the highest-leverage changes a broker can make The guarantee structure addresses promise, risk, fee, and urgency in a single sentence Offering a guarantee doesn't lower your fee — it justifies charging a marketing retainer on top of your commission The marketing retainer is refundable if the result isn't hit — this removes the client's fear and signals your confidence Build your guarantee from your real track record — it must be specific and genuinely deliverable Present your guarantee at every new client meeting using a consistent checklist The guarantee works when you do the work — it's a commitment to yourself as much as to the client

August 5, 2026Episode 1067 min

Episode 106 - Brokerage Benchmarks

Rod Santomassimo walks through the critical performance benchmarks every commercial real estate broker needs to know — and measure. Most brokers track closings and commissions but ignore the upstream activity metrics that actually predict results. In this episode, Rod lays out the full pipeline conversion framework, from first calls to closed deals, with specific targets at each stage. Key Takeaways If you're not measuring conversations and meetings, you're flying blind A weak pitch win rate is almost always a discovery problem, not a closing problem Your value proposition on the phone determines whether you even get to the meeting Discipline and execution — not market conditions — drive your conversion rates Know your numbers at every stage: the broker who tracks wins

July 29, 2026Episode 1056 min

Episode 105 - The Aikido Approach

Rod Santomassimo breaks down a counterintuitive framework for handling the toughest objections in commercial real estate — one borrowed from the martial art of Aikido. Instead of pushing back against resistance, the Aikido approach teaches brokers to redirect the energy : acknowledge the objection, validate the prospect's position, and pivot to curiosity. The result is a conversation that never turns adversarial and always moves forward. Key Takeaways Objections are not roadblocks — they are redirectable energy Always acknowledge and validate before pivoting Questions beat arguments every time — curiosity keeps the conversation alive Market uncertainty is a prospecting opportunity for brokers who are prepared Have a scripted, rehearsed response for every common objection before you pick up the phone

July 22, 2026Episode 1044 min

Episode 104 - "I Already Have a Broker"

Rod Santomassimo tackles one of the most common — and most mishandled — objections in CRE prospecting: "I already have a broker." Most brokers hear it and hang up. Rod reframes it entirely: this isn't a dead end, it's the beginning of a relationship. He lays out a clear three-step process for turning this objection into a long-term pipeline opportunity. Key Takeaways "I already have a broker" is a pipeline opportunity, not a rejection Asking what they value most reveals gaps and gives you powerful prospect intel Silence after your question is a feature, not a flaw — let them think Asking permission to follow up almost always gets a yes Consistent, relevant follow-up turns today's no into tomorrow's client

April 1, 2026Episode 10336 min

Episode 103 – Terri Sjodin "Presentation Ready"

Terri walks through how a background in competitive speech and debate evolved into a 30+ year career helping top performers—CEOs, brokers, sales teams, and even members of Congress—win more often by mastering persuasive communication. Her foundation is simple but powerful: communication is not about what you say—it's about what the listener hears, processes, and acts on. She shares how her early career "breaking territory" through cold calling and filling rooms from scratch shaped her philosophy: you must be both scrappy enough to earn attention and skilled enough to convert it . The core problem she sees today: experienced professionals rely on confidence instead of preparation, while newer professionals lack structure—so both default to "winging it." And that's costing deals. Her latest book, Presentation Ready , is built on a multi-phase research study identifying the 12 most common mistakes that cause professionals to lose opportunities—based on both self-reflection and buyer feedback. What You'll Learn (from Terri) Why "winging it" is the silent deal killer – Veterans rely on experience → leads to complacency – Newer professionals lack a repeatable structure – Result: inconsistent messaging and missed outcomes The real mistake: being informative instead of persuasive – Most professionals "data dump" instead of influencing decisions – Buyers don't reward information—they reward clarity and conviction The disconnect that's costing you deals – You think you're clear → your audience thinks you're boring – #1 feedback from buyers: "The presentation was boring" Why recording yourself is non-negotiable – You cannot fix what you don't recognize – Watching yourself exposes verbal habits, weak structure, and lack of impact The importance of scrimmaging (roleplay) – Top performers don't practice presentations—they rehearse outcomes – Like athletes, drills build specific skills that show up under pressure Why "scrappy + structured" wins in today's market – Scrappy gets you in the room – Skill gets you the deal About Terri Sjodin Terri Sjodin is the Founder of Sjodin Communications and one of the leading experts in persuasive presentations and sales communication. She is a New York Times best-selling author, Hall of Fame speaker (National Speakers Association), and has worked with Fortune 500 companies, national sales teams, and government leaders. Her latest book, Presentation Ready , is based on decades of real-world experience and a multi-phase research study on what actually causes professionals to win—or lose—opportunities.

February 4, 2026Episode 10227 min

Episode 102: Leveling Up - How Lev Mavashev Built a Dominant CRE Brokerage in the Most Competitive City in the World

Host: Rod Santomassimo Guest: Lev Mavashev (Principal, Alpha Realty, Ney York, NY) Lev Mavashev (Principal, Alpha Realty) walks through how a technical, numbers-driven background (CPA + Deloitte) turned into a long-term career in NYC multifamily brokerage —and why specialization is the reason he's been able to scale, survive disruption, and keep taking market share. Lev shares how he entered brokerage the old-school way: book + phone + cold calling —and even landed a seller on his first call , then had to ask the team what to do next. The bigger lesson: activity matters, but structure matters more. He explains that two years in, he invested in coaching, learned to value his time based on what he intends to earn (not last year's income), and made a bold move early: hired an assistant on his own dime , which he credits as a major accelerator. Lev also breaks down why he founded Alpha Realty in 2016, why Alpha is exclusively multifamily , and how he stayed steady through major headwinds—especially NYC's 2019 rent law changes and then COVID—by being the advisor clients could reach when others disappeared. What You'll Learn (from Lev) Why specializing (and staying there) beats chasing "whatever deal is available" How Lev used disruption (2019 rent laws + COVID) to deepen advisory relationships and gain share The mindset shift: valuing your time based on your goal income—and staffing accordingly How Alpha scaled to 14 total team members and is now restructuring into micro-specialists inside multifamily products Where Lev is using AI today: email triage, marketing support, OM/BOV drafts—while still testing the edge of AI calling Lev's Core Framework "Get on a team + find your niche + stay in your lane." He frames it as being a big fish in a small pond , instead of trying to win the whole ocean. About: Lev Mavashev Lev Mavashev is the Founder and Principal of Alpha Realty, a thriving real estate brokerage firm specializing in NYC Multifamily properties. Lev is among the industry's top tier professionals and considered one of the most active brokers and power deal makers in the investment-sales market.