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/

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/