The Massimo Show

Hosted by Rod Santomassimo

BusinessInterviews guests

Website RSS feed

Episodes

100

Latest episode

Apr 2026

Language

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.

Listen to episodes

60 recent

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.

January 2, 2026Episode 10119 min

Episode 101 – From Broker to Dominator: How Reid Bennett Transformed His Career with the Massimo Methods

Host: Rod Santomassimo Guest: Reid Bennett, National Council Chair – SVN Multifamily | Massimo Group Coach | 7-Figure CRE Producer 🎙️ In this milestone episode of The Massimo Show, Rod reconnects with longtime client-turned-coach Reid Bennett to reveal how he went from being a solid multifamily broker to a nationally recognized leader, team-builder, and seven-figure producer. If you're an established commercial real estate professional feeling stuck on the transactional treadmill—or trying to figure out what's next—this one's for you. Reid shares his raw, behind-the-scenes journey from chaos to clarity: How after 18 years in the business, he still felt like he was guessing on who to call next Why he finally invested in coaching, despite already being a top producer The specific systems and cadence he implemented that quadrupled his income How he broke through inconsistent revenue cycles and built a practice that delivers consistent 7-figure years His transition from broker to investor and mentor for brokers nationwide PLUS: Rod and Reid break down the power of the "What's New, What's Next, and How Can I Help?" approach—a simple framework that helped Reid land a 440-unit deal during COVID from a cold, dormant lead. 🚀 What You'll Learn in Episode 101: How top brokers eliminate the income rollercoaster (hint: systems) Why every high-level broker needs coaching—even the veterans The secrets to scaling a team while maintaining control and quality Reid's mindset shift from chasing commissions to building wealth The ripple effect of coaching: why teaching others sharpens your own skills 🧠 Who This Episode Is For: ✅ CRE brokers earning $300K+ who are stuck and want exponential growth ✅ Team leaders seeking a roadmap to scale without burnout ✅ Multifamily specialists looking to transition into leadership or investment roles ✅ Any broker who wants to dominate their niche and build a business—and life—they love About Reid Bennett: Reid Bennett is the National Council Chair of SVN's Multifamily Division, overseeing a national network of brokers. With over two decades of experience, Reid transformed his own practice through the Massimo Group's coaching—and now coaches other brokers to do the same. He's an active investor, elite producer, and coach who believes in building wealth with intention and helping others rise. 🎧 Listen now and discover what happens when a broker stops winging it and starts running it like a business.

April 29, 2025Episode 9726 min

Episode 97: Nick Huber – Get Rich Doing Boring Things

On this episode of the Massimo Show What if we told you the road to wealth isn't lined with apps, funding rounds, or viral ideas… but instead with dust, sweat, and a whole lot of cardboard boxes? In this eye-opening Episode 97 of The Massimo Show, Rod welcomes one of the most talked-about entrepreneurs on the internet today - Nick Huber, the man behind The Sweaty Startup movement. You've seen his tweets, you've heard the opinions, and now it's time to get the full story from Nick himself — raw, unfiltered, and rich with insight. Nick's Journey: From Dorm Rooms to Boardrooms Nick didn't dream of being an entrepreneur — he became one out of necessity and curiosity. Raised in southern Indiana by a middle-class family — his dad in real estate development, his mom a school nurse — Nick learned the value of work early. At Cornell University, he wasn't reading books on startups or idolizing Silicon Valley founders. Instead, he was hauling boxes, renting trucks, and building Storage Squad, a college student storage company that scaled to 25 campuses nationwide. That "boring" business was just the beginning. Fast-forward a few years and Nick is now the co-founder of Bolt Storage, a self-storage empire managing over 2 million square feet across 68 locations — with assets valued north of $100 million. Oh, and he's not done yet. He also acquired a controlling stake in Somewhere.com, an online hiring marketplace. Oh yeah… and he's got nearly 800,000 social media followers tuning in for his blunt, refreshing takes on business, wealth, and life. Key Themes Covered in This Episode: The beauty of boring businesses: Why low-glamour, high-demand services offer more freedom and upside than trend-chasing startups From sweaty work to scalable systems: How Nick transitioned from hauling boxes to managing hundreds of employees Momentum is everything: Nick breaks down how small steps (and sweaty ones) led to massive success Work-life alignment, not balance: His take on how to build a business that supports your life, not consumes it Social media with a mission: How Nick uses Twitter and podcasting to teach, build brand equity, and source deal flow Why VC-backed startups aren't for everyone (or even most people) — and what the mainstream startup culture gets completely wrong Building a $100M+ portfolio without big capital to start: The true power of leverage, partnerships, and grit Why young brokers and business owners should skip the sexy ideas and focus on real pain points Grab Nick's new book: The Sweaty Startup: How to Get Rich Doing Boring Things — a blueprint for building freedom through simplicity, hard work, and smart systems. If you're tired of being reactive, constantly chasing shiny objects, or just stuck on the transactional treadmill — this episode will challenge your thinking and energize your vision. Listen now to learn how to build wealth, impact, and a life you actually love — the boring way. Want to grow your brokerage business fast? Book a free strategy call at https://massimo-group.com/ www.sweatystartup.com www.nickhuber.com www.sweatystartupbook.com www.somewhere.com/nick www.boltstorage.com www.recostseg.com www.adrhino.com www.spidexx.com www.boldseo.com www.webrun.com www.titanrisk.com www.recruitjet.com www.hubermethod.com www.x.com/sweatystartup www.instagram.com/sweatystartup www.linkedin.com/in/sweatystartup www.youtube.com/sweatystartupwww.tiktok.com/sweatystartup www.threads.net/@sweatystartup.com https://podcasts.apple.com/us/podcast/the-nick-huber-show/id1576120606 https://podcasts.apple.com/us/podcast/the-sweaty-startup/id1445260221 Link to buy the book on Amazon: https://amzn.to/4bLazjW Link to buy the book in the UK: https://bit.ly/422njPW

April 14, 2025Episode 9631 min

E 96: Matt McGregor - Cold Calling is Dead… Or Is It?

On this episode of the Massimo Show In Episode 96 of The Massimo Show, Rod sits down once again with one of the most downloaded guests in show history — Matt McGregor of Colliers International and a Massimo Master Broker. Matt and Rod go deep into what they call the evolution of cold calling. Spoiler: they don't believe in "ice cold" calls anymore — and they've got the stats to back it up. They reveal: Why 92% of calls now go straight to voicemail—and what to do about it How to turn a cold call into a warm one using tech, timing, and tactics The specific multi-touch sequences Matt uses (emails, DMs, text, and mailers) Why bots, AI, and campaign automation are changing the game for prospecting The launch of WarmCaller, Matt's new patented tech that ranks and feeds you personalized, real-time prospecting insights How brokers can finally stop sounding like "just another sales pitch" and start making calls that truly resonate Rod and Matt even share real conversion stats from their own sales teams — over 5,900+ calls tracked — to expose what works (and what doesn't) in today's CRE environment. If you're still dialing blind and hoping for the best, this episode will shift your mindset and your results. For more info or to request a demo of WarmCaller, visit warmcaller.com Want to grow your brokerage business fast? Book a free strategy call at https://massimo-group.com/

September 27, 2024Episode 9531 min

E 95: Skylar Romines- Breaking Down Barriers: Mastering Commercial Real Estate Insurance

On this episode of the Massimo Show Rod sits down with Skylar Romines, founder and owner of ATW Advisors in Orange County, California. Skylar is an expert in commercial real estate insurance with 15 years experience in the insurance industry. She passionately advocates on behalf of business owners, helping them secure better insurance terms and control over their programs. Skylar described herself as a late bloomer who struggled socially in high school, but found her footing later in life. During college, she started working at Nordstrom, but later transitioned to insurance after receiving advice from a family member. She unexpectedly found success in the insurance industry while earning her psychology degree. Skylar discusses the challenges and changes within the insurance industry, particularly in the current hard market cycle, where there are fewer options and insurance premiums are increasing significantly. She advises investors to be proactive, working closely with their brokers to avoid pitfalls, such as shopping multiple brokers and delaying insurance considerations. One of the key points Skylar made was that real estate investors should engage their insurance brokers early during the acquisition process to ensure accurate quotes, avoiding any surprises with coverage costs, and to fully understand any associated risks. Investors should focus on maintaining property conditions, as insurance costs often reflect the risk associated with property age, systems, and geographical factors. Skylar shared her recent success and expereience using social media platforms, like Twitter and LinkedIn, to connect with professionals and grow her network in the real estate industry. She notes how Twitter (X) can foster a sense of community and engagement across industries, unlike LinkedIn, which is more formal. Additionally, Skylar mentions her upcoming book relesased this July, So She Did: Stories, Stats & Strategies to Help Women Win, which focuses on the underrepresentation of women in high-paying roles in the insurance and real estate industries. Drawing from dozens of interviews, she shares compelling statistics, actionable advice, and the collective wisdom of women who are challenging norms and inspiring women to claim their own seats at the table of leadership, ownership, and equity. Skyler hopes to empower women to rise, thrive, and lead in their own unique and inspiring ways. Overall, the episode provides insights into Skylar's journey from a college student with a side job to a successful commercial insurance expert. It also touches on broader themes in commercial real estate, the state of the insurance industry, and the importance of networking in business. Note: These highlights are designed to provide an overview of this episode's content. Listeners are encouraged to tune in to the full episode for a comprehensive understanding of the topics covered. At the Massimo Group we have 15 years of experience helping the most dedicated brokers, like you, build the CRE business and life they have always desired. If you'd like to learn more visit https://massimo-group.com/

May 17, 2024Episode 9435 min

E 94: Ken Ashley - The CRE Prescription

On this episode of the Massimo Show Rod sits down with Ken Ashley, CCIM, MCR, SIOR, Executive Director of Cushman & Wakefield and Founder of CREI, Commercial Real Estate Influencer. Ken is a successful Atlanta broker with nearly 30 years experience with tenant representation and sales in the commercial real estate industry. They discuss the importance of building a personal brand and using social media effectively in the commercial real estate industry. Ken shares his strategies for engaging with prospects, valuing your time, and creating a strong online presence. He emphasizes the need to focus on the other person and provide value in order to build trust and influence. Ken also announces the upcoming CREI Summit, a conference dedicated to helping commercial real estate professionals build their brands and increase their influence. Note: These highlights are designed to provide an overview of this episode's content. Listeners are encouraged to tune in to the full episode for a comprehensive understanding of the topics covered. At the Massimo Group we have 15 years of experience helping the most dedicated brokers, like you, build the CRE business and life they have always desired. If you'd like to learn more visit https://massimo-group.com/

February 23, 2024Episode 9329 min

E 93: Ron Koenigsberg - Power Broker: How to Succeed In Life And Business

On this episode of the Massimo Show Rod sits down with Ron Koenigsberg, Founder & President at American Investment Properties, a successful Long Island Broker with 30 years experience in the commercial real estate brokerage industry. As Ron recalled the pathway to his start in commercial real estate he stated that he "[wished] everything was a straight path… but there are lessons to be learned that are probably never in a straight path, and you certainly have to have a little bit of resilience along the way." Ron describes his journey from growing up in Long Island and watching his father survey buildings and construction sites, through his time in college, first jobs, and the eventual decision to establish his own firm, American Investment Properties. Rod goes on to ask Ron what's the one common thread that allowed him to not only succeed, but thrive during the market cycles over the years? Ron responded that he attributes his success to two factors, his call counts and his coaching from The Massimo Group. Ron recounts a time in his career when he was scared, he was making a lot of calls, but business had come to a halt. After seeing an advertisement for The Massimo Group, Ron encountered James Nelson and asked him if The Massimo Group was really worth it, since it was expensive! Ron was a successful broker, "but [he didn't] know what [he didn't] know." After 10 years with The Massimo Group, Ron stated that "It changed my life. Within five years, I went from really losing money or just getting by to… Broker of The Year… and I won the MVP (The Massimo Group's Most Valuable Producer award) bat on the back of my book." Rod then goes on to ask Ron what the foundations to his success are? Ron immediately replied with relationships, daily phone calls, and reaching out to his prospects, especially through face to face communication and active listening. Ron notes that while social media is important, it's also a double edged sword. 93% of the essential parts of how we communicate, per an FBI study in the 1970s and 1980s, never come through with the use of technology. Lastly, they discuss Ron's new book, Power Broker: How to Succeed In Life And Business. This is an essential mindset book for any broker on how to attack everyday, especially if you're feeling stuck, questioning what to do, or are plateaued. It details 9 skills that Ron believes are essential for making people successful. You can find Ron's book on Amazon, Audible or at www.RonKoenigsberg.com. Note: These highlights are designed to provide an overview of this episode's content. Listeners are encouraged to tune in to the full episode for a comprehensive understanding of the topics covered. At the Massimo Group we have 15 years of experience helping the most dedicated brokers, like you, build the CRE business and life they have always desired. If you'd like to learn more visit https://massimo-group.com/

February 5, 2024Episode 9232 min

E 92: Jerry Anderson - Surviving Inflection Points in CRE Brokerage

On this episode of the Massimo Show Rod sits down with one of his mentors, Jerry Anderson, a veteran in the commercial real estate brokerage industry with over 50 years of experience. Jerry, currently a Corporate Advisor for eXp Commercial, has successfully run two international brokerage companies and is a pioneer in single point of contact and master franchise brokerage models. Jerry has succeeded and thrived through at least four economic downturns, otherwise known as inflection points in brokerage, throughout his career, so Rod begins the podcast by asking him about the current state of the market and how it differs from previous downturns he's experienced. At first glance, Jerry thought this downturn was similar to the 2008 financial crisis, but after watching some activity over the past few months, he said there are several differences, especially where things are heating up in the financial/lending industry, and "not in a good way." Jerry elaborates that the central dilemma for US brokers right now is that "Interest rate percentages have really been very, very low, in my opinion, for way too long. We have to reset all that. We have to get people accustomed to higher interest rates. If you own a property…at 3% or 4%, [we have to ask] why would you want to sell?... [and advise] All you're going to do is pay capital gains tax, move on, and have a higher interest rate." Jerry also points out that interest rates used to be higher, he remembers he "was pretty happy when interest rates [used to be] 12% and I was making money as a broker at 12%." With Jerry's lengthy expertise, Rod asks what advice he would give to brokers saying there's no velocity in the current market and there's "nothing I can do." Jerry suggests that interest rates are relative, brokers have "had it pretty easy for the last 10 years… the habits they gave up, they're going to have to reinsert… You have to be an advisor in this marketplace more than ever before because people don't need you… you have to help them figure out what they do need." "It's a beautiful time for you as a broker to make calls and say, let me share with you what's happening because we have our thumb on the heartbeat of the market." Jerry continues to explain that brokers have to refocus, understand where the market is and its impacts, and share that knowledge and awareness with property owners and buyers to put them "in a position to be successful…" Rod further emphasizes Jerry's points by adding that The Massimo Group encourages our clients to be an authority in the market versus a commodity, an advisor versus a facilitator. "...This is not a time to take your foot off the pedal. This is the time to jam that pedal to the floor [with] more calls, more effort, more work if you want to just maintain a sliver of market share…" Lastly, Rod enquires what Jerry feels are some of the greatest inflection points in brokerage history that have changed the way brokers work. Jerry recalled the Tax Reform Act of 1986, technology, particularly software and the internet, and the structure of brokerage companies. Jerry briefly discusses his white paper The Commercial Real Estate Brokerage Industry Is Broken For Both Brokers and Associates. Rod postulates if he feels brokerage was broken back then and it still is today, how can we fix it? Jerry details the strengths and weaknesses of some prior brokerage models, from the small shop to national and international brokerage companies, franchises, and now virtual models. Jerry believes the current model that eXp is experimenting with is the closest to having it figured out. Note: These highlights are designed to provide an overview of this episode's content. Listeners are encouraged to tune in to the full episode for a comprehensive understanding of the topics covered. At the Massimo Group we have 15 years of experience helping the most dedicated brokers, like you, build the CRE business and life they have always desired. If you'd like to learn more visit https://massimo-group.com/

December 28, 2023Episode 9122 min

E 91: Bobbie Mastracci - Secrets to Success In CRE

On this episode of the Massimo Show Rod sits down with Bobbie Mastracci, CCIM, SIOR and Principal of Phoenix West Commercial, LLC, also known as the "Go To Broker" for the West Valley of Phoenix Metro. Bobbie is a successful real estate broker and Massimo coach with 20 years of CRE experience. She works with corporate and small business clients, both locally and nationally, and prides herself on her faith, dedication, and ability to deliver unmatched customer service. Bobby shares her journey from her first job in high school, to being a hair color platform artist, and then entering the world of commercial real estate. Not to mention relocating from Pennsylvania to Arizona. She discusses the importance of education, setting goals, and having a strong work ethic. Bobby also addresses the misconception that it is harder for women to succeed in commercial real estate and emphasizes the importance of faith, discipline, persistence, and consistency to achieve success. Bobby advises, to those considering a career change, to be prepared for a slow start and to find a mentor or coach to guide them. She also talks about the benefits of embracing technology, including AI, in the industry. Overall, she encourages listeners to have a positive mindset, seek opportunities, and take action to achieve their goals. At the Massimo Group we have 15 years of experience helping the most dedicated brokers, like you, build the CRE business and life they have always desired. If you'd like to learn more visit https://massimo-group.com/ Note: These highlights are designed to provide an overview of this episode's content. Listeners are encouraged to tune in to the full episode for a comprehensive understanding of the topics covered.