Founder, Founder, Founder: Bob Gillespie on PropTech, AI, and What Actually Wins in Commercial Real Estate

What Does It Take From A Logistics Perspective to Host the World Cup?

The World Cup starts today, June 11 and Miami [https://miamifwc26.com/] will host our first match on June 15. Planning for this event, that will put Miami on the world stage again - we just wrapped up F-1, started as soon as Miami was awarded the 2026 World Cup four years ago. From fan transportation [https://miamifwc26.com/miami-transportation/] to and from the games and events, to the logistics [https://www.gw-world.com/us/newsroom/world-cup-freight-capacity-logistics/] of moving players, equipment, food and beverage to the stadium and events, there are a lot moving parts. Luckily for Miami, a lot of the infrastructure projects including the airports, stadiums and roadwork, had already been underway due to the growth the region experienced during COVID. I am sure there will be some challenges,

Why Do So Few Commercial Real Estate Sellers Do 1031 Exchanges? A Conversation with Jon Hilley

What do Scrooge McDuck [https://youtu.be/p9d8l-Gkweg?si=fbn2px9LKVEw6EIk], The Square Grouper [https://squaregrouper.net/], Goldman Sachs, commercial real estate and taxes have in common? The answer is Jon Hilley [https://www.linkedin.com/in/jonathanhilley/], founder of 1031 Specialists [https://www.1031specialists.com/]. In this episode, we dive into why so few sellers do 1031 exchanges, what differentiates 1031 Specialists from other intermediaries and the Golden Strategy. Jon brings his wide range of experience, curiosity and his "Client Happiness Project" to elevate the 1031 experience. "We are in the joy business". FEA Economic Impact Studies of 1031 Exchanges [https://www.1031.org/assets/docs/FEA-1031_Impact_of_American_Families_Plan-Key_Findings_of_Studies.pdf]

Tourism, Tech & Tipping Points: What’s Fueling Miami Commercial Real Estate

What’s really driving Miami commercial real estate right now? In this episode, we break down the forces behind the market’s momentum—from record tourism and global events to tech growth, international investment, and shifting consumer demographics. Using the latest tourism trends and real-world examples, we explore how major demand drivers like Formula One [https://www.formula1.com/en/racing/2026/miami], the World Cup [https://fifaworldcup26.hospitality.fifa.com/en/venues/miami?utm_source=google&utm_medium=cpc&utm_campaign=hostcity_mia&xref=google_hostcity_mia&gad_source=1&gad_campaignid=22798176412&gbraid=0AAAAA-icCsH0ORhcXnNQZ6A1nxp8iCBC8&gclid=CjwKCAjwt7XQBhBkEiwAtStpp-7j_Hxpy-5phtO6x75_4Ay_-_Rc8GogIS1SJ0_Co2jNKpDvy5-dDhoC7ysQAvD_BwE], Art Basel [https://www.artbasel.com/miami-beach/at-the-show?lang=en], and eMerge Americas ripple through Miami’s commercial landscape. This isn’t just a hospitality story. It’s a conversation about how visitor growth fuels retail, industrial, office, mixed-use development, infrastructure, and the broader business ecosystem across South Florida. We also discuss how rising international travel patterns from regions like South America, Europe, Asia-Oceania, and Africa often become early signals for business expansion, capital inflows, and long-term investment activity. If you want to understand where the Miami commercial market may be heading next, this episode connects the dots between the numbers, the headlines, and the opportunities on the ground.

Founder, Founder, Founder: Bob Gillespie on PropTech, AI, and What Actually Wins in Commercial Real Estate

In real estate it is all about location, location, location... In this episode we sit down with Bob Gillespie, Managing Partner of REACH Commercial at Second Century Ventures, to talk about what really drives success in PropTech. Bob shares his journey from computer science and startup operations to venture investing, and explains how REACH Commercial identifies technologies that can make commercial real estate faster, smarter, and more profitable. The conversation explores why commercial real estate has historically lagged in technology adoption, what makes a startup investable, and why Bob believes the founder often matters more than the initial idea. He also breaks down the biggest reasons PropTech companies fail, why traction is everything, and how associations can play a meaningful role in fostering innovation rather than just reacting to it. Bob also offers a candid perspective on AI in commercial real estate—what excites him, what makes him cautious, and why defensibility, workflow integration, and real market demand matter far more than hype. Along the way, he shares examples from companies in the REACH portfolio and gives listeners a rare inside look at how venture investors think about scale, adoption, and long-term value creation.

Miami’s New Cycle: How Wealth Migration Is Repricing Office, Retail, Multifamily & Logistics

A practical, CRE-focused look at why wealth migration is reshaping South Florida’s office, multifamily, retail, and industrial markets—and what comes next. Miami isn’t just adding people—it’s absorbing capital, talent, and corporate gravity. In this episode, we break down the wealth migration into Miami and greater South Florida and what it signals for commercial real estate across the region.