{"podcast":{"title":"Between Two Chairs - Demystifying Commercial Real Estate","slug":"between-two-chairs-demystifying-commercial-real-estate-6318176","podcast_index_feed_id":6318176,"rss_url":"https://media.rss.com/betweentwochairs/feed.xml","website_url":"https://rss.com/podcasts/betweentwochairs","image_url":"https://media.rss.com/betweentwochairs/20230419_060438_94a75ad4f123d520c6011d748ba0d6eb.jpg","author":"Fernando Arencibia, Jr. and Jennifer Wollmann","episode_count":163,"summary":"Welcome to Between Two Chairs: Demystifying Commercial Real Estate, the podcast that brings you the latest insights and trends from the Miami commercial real estate industry. Co-hosts Fernando Arencibia Jr. and Jennifer Wollmann, both former Chairman of the Board for the largest local real estate association in the Country, the Miami Association of Realtors, bring a wealth of experience and knowledge to every conversation. In each episode, we dive deep into the world of commercial real estate in Miami, speaking with market leaders, exploring the latest trends, and breaking down complex concepts to make them accessible for everyone. Whether you're a seasoned real estate professional, a curious investor, or just interested in the Miami market in general, Between Two Chairs is the podcast for you. So sit back, relax, and join us as we demystify the world of commercial real estate in Miami.","last_synced_at":null,"page_url":"https://stenobird.com/podcast/between-two-chairs-demystifying-commercial-real-estate-6318176"},"episode":{"title":"Founder, Founder, Founder: Bob Gillespie on PropTech, AI, and What Actually Wins in Commercial Real Estate","slug":"founder-founder-founder-bob-gillespie-on-proptech-ai-and-what-actually-wins-in-commercial-real-estate","published_at":"2026-05-21T19:05:00+00:00","page_url":"https://stenobird.com/podcast/between-two-chairs-demystifying-commercial-real-estate-6318176/founder-founder-founder-bob-gillespie-on-proptech-ai-and-what-actually-wins-in-commercial-real-estate","show_page_url":"https://stenobird.com/podcast/between-two-chairs-demystifying-commercial-real-estate-6318176","url":"https://rss.com/podcasts/betweentwochairs/2840878","audio_url":"https://content.rss.com/episodes/204235/2840878/betweentwochairs/2026_05_19_18_12_29_9526a095-c6b3-4f87-a88b-a5801a23608c.mp3","summary":"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.","meta_description":"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 Se…","key_points":[],"chapters":[],"topics":[],"duration_seconds":3253,"processing_state":"not_requested","actions":[{"name":"request_transcript","method":"POST","url":"https://stenobird.com/v1/public/podcasts/between-two-chairs-demystifying-commercial-real-estate-6318176/episodes/founder-founder-founder-bob-gillespie-on-proptech-ai-and-what-actually-wins-in-commercial-real-estate/transcription-requests","description":"Idempotently request low-priority transcript generation for this episode."},{"name":"read_markdown","method":"GET","url":"https://stenobird.com/podcast/between-two-chairs-demystifying-commercial-real-estate-6318176/founder-founder-founder-bob-gillespie-on-proptech-ai-and-what-actually-wins-in-commercial-real-estate.md","description":"Read the agent-friendly Markdown representation of this episode resource."}]}}