Scaling Station Podcast

Will Rodosky
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Scaling Station Podcast features conversations with founders, operators, and leaders rethinking how the built world works. Host Will Rodosky explores the intersection of real estate, technology, and entrepreneurship — uncovering the strategies, setbacks, and stories behind scaling businesses that shape our communities.

  1. 11/18/2025

    Leasing NYC: How Relm Is Rewriting Apartment Search in the Big Apple

    New episode of the Scaling Station podcast by Orza Growth Partners is live!! This week, I sat down with Jackson Reiter, co-founder of Relm, the AI platform cutting underwriting to minutes and redefining how the industry discovers space. It’s a killer conversation: grit, systems thinking, and a vision that’s pushing dealmaking into the future.

    27 min

  2. 11/13/2025

    From DJ Booth to Cutting CRE Lease Times by 90% | Rafael Weiss, Sytes

    Sytes (sytescre.com) is changing how leasing gets done in commercial real estate by putting tenants in the driver’s seat.  Instead of searching through listings, tenants outline exactly where they want to be and what they need. Landlords and developers then match those requirements with real opportunities, creating a cleaner and faster path to deals. In this conversation, Rafael Weiss breaks down how Sytes acts as a true matchmaker in the market. Tenants bring demand. Landlords bring supply. Sytes connects the two with real time criteria and removes the noise that slows leasing down.  The result is a more transparent and efficient process for everyone involved. We also talk about Rafael’s journey from music and DJing into building software for commercial real estate. His perspective as both a founder and investor shapes how he builds tools that solve real problems and streamline decisions in a traditionally slow industry. #commercialrealestate #proptech #creleasing

    37 min

  3. 11/04/2025

    How Agents Prove Their Value After Zillow | Eric Ellis, LookBookLink | Scaling Station Podcast

    What do you do when the old gatekeepers of listings are gone and buyers can find everything on their phone?  In this episode, Will Rodosky sits down with Eric Ellis — a photographer-turned-founder who built Lookbook Link after paying $2,500 for a site and realizing Linktree wasn’t enough. Eric reveals the small product decisions that solve a massive problem for agents: a lightweight, branded personal business site that combines photos, videos and documents, syncs across teams, and costs just $50/year.  He explains why hyperlocal content — think dog‑park guides and mortgage primers — beats generic property searches and how a live team feed keeps every agent on message. Key moments: • The $2,500 website that birthed a better idea • Why Linktree failed him — and what replaced it • Team feeds that push updates instantly to every agent • A dog‑park playbook that converts leads into clients • The danger of feature bloat — simplicity as strategy Eric also shares a negotiating mindset (Yes, he reads Never Split the Difference) and a closing plea to agents: use tech to strengthen relationships, not replace them. Ready to stop sending “one-off” emails and start leaving a professional, bookmarkable business book behind? Watch, take notes, and act. #PropTech #RealEstateMarketing #LookbookLink #AgentTools #Brokerage #PersonalBrand #LeadGen #Hyperlocal #ScalingStation #Entrepreneur

    17 min

  4. 10/28/2025

    Why CRE pros are switching from ChatGPT to Propaya

    What happens when a family's side hustle becomes the blueprint to fix decades of paperwork chaos in commercial property deals? On this episode of Scaling Station, host Will Rodosky sits down with Reader Wang — CEO and Co-Founder of Propaya (YC S24) — who translated his family’s experience in property management into a product that reads, organizes, and explains leases in minutes. From his mother’s shift into property management to a 70-unit portfolio tracked on shaky spreadsheets, Reader recounts the exact moment he decided: documents should do the work, not people. He reveals how a novel, zero-shot approach turns dense legal contracts into traceable data and a conversational assistant that remembers your entire portfolio. Key moments you’ll watch for: • The “take-a-photo-of-a-lease” idea that sparked the company • Why missed clauses can cost hundreds of thousands • How Propaya cites sources so humans can verify fast • The product demo: chat with a document, then chat with your whole portfolio Takeaway: Use technology to automate facts — spend your time winning relationships. Try Propaya or connect with Reader Wang on LinkedIn. Don’t just listen — act: extract one lease today and reclaim the hours you spend on paperwork. #PropTech #LeaseAbstraction #Propaya #RealEstateTech #CRE #DocumentAI #Founders #Scaling #PropertyManagement

    20 min

  5. 10/16/2025

    Digitizing Real Estate: The Hidden Value Inside Buildings | Matthew Schneider, Building | Scaling Station Podcast

    What if the most valuable part of a property isn’t the land or the lease - it’s the invisible trail of data living inside it? Matthew Schneider, Founder & CEO of Building, joins Scaling Station to dig into how real estate is finally being digitized — and why most of what’s happening so far misses the point. Recorded amid travel, trades, and even a COVID battle, this episode pushes past buzzwords to show how tech can genuinely reduce risk and unlock liquidity. In this episode you'll hear: How Matthew pivoted from tokenized syndication to monetizing property dataWhy blockchain is about authenticity, not hypeThe real power of a digital twin: remote monitoring, predictive maintenance, investor confidenceHow certified, audited digital assets can command a premiumA step-by-step playbook: organize, verify, automateIf you invest in, build, or underwrite real estate, this is your roadmap to making assets smarter, more transparent, and more liquid. Connect: Matthew A. Schneider on LinkedIn | Listen to his podcast: Code & Concrete #PropTech #RealEstate #DigitalTwin #Tokenization #BuildingTech #AssetData

    32 min

  6. 10/07/2025

    Stop Chasing Parcels. Let Deals Find You | Dylan Goren, Pillar | Scaling Station Podcast

    What if an acquisition team could turn dusty public records and cold contacts into a repeatable pipeline — in weeks, not quarters? Dylan Goren, Co-founder and CEO of Pillar, sits down with Will on Scaling Station to reveal how software built for real estate is being rewired to automate the toughest part of development: landing the right site and opening the conversation with owners. From JLL tech to launching Pillar in Jan 2023, Dylan explains the quiet pivots, surprising customer requests, and the moment outreach became core to the product. Highlights: •  Why maps and layers aren’t enough — find underwriting signals earlier •  How verified contact data + contextual offers cut wasted outreach •  The playbook for hyper-personalized land outreach at scale •  Where AI actually helps small teams beat incumbents •  Dylan’s 12–18 month vision: bake underwriting logic into discovery This episode is for builders, developers, and operators who want a surgical approach to off-market opportunities. Watch, take notes, then act. Learn more: pillar.codes | Connect: Dylan Goren on LinkedIn #PropTech #LandAcquisition #RealEstateAI #Pillar #SiteSelection #OffMarket #DeveloperTech #SkipTracing #Underwriting

    24 min

  7. 10/06/2025

    How a Late-Night Bug Became a Growth Engine | Sam Chlebowski, Motion.io | Scaling Station Podcast

    What do you do when the thing that breaks your product becomes the thing that saves your company? Sam Chlebowski — Co-founder of Motion.io platform — joins Scaling Station to tell the behind-the-scenes story nobody expects: the chaotic night that exposed a flaw, the gut-wrenching decision to pivot, and the unlikely sequence that turned panic into purpose. You’ll ride the tense moments with Sam: • 🌙 The midnight incident that nearly shut everything down — and the moral choice that followed. • 🔧 The 48-hour hack that revealed a hidden user behavior no one studied. • 🚀 The counterintuitive playbook they used to turn breakdown into traction. Bold takeaway: product mistakes can be strategic signals if you know how to listen. This is a raw founder confession — filled with real metrics, cultural trade-offs, and the exact decisions that rewired growth strategy. Don’t just watch—learn the mindset that turns crisis into runway. Join us, apply one tactic this week, and report back. #startup #founderstories #growthhacking #productleadership #Motionio #entrepreneurship

    23 min

  8. 10/03/2025

    What Nobody is talking about in PropTech | Lilian Chen, Proptimal

    What if the playbook used by billion-dollar firms was suddenly accessible to a two-person shop? In this episode, Will sits down with Lilian Chen — Founder of Proptimal — who’s making institutional knowledge, tools, and resources available to everyday investors.  Lilian has advised on more than $10 billion in commercial real estate transactions across 200+ firms, from first-time buyers to institutions with billions under management. She shares the hard lessons, cultural influences, and career moves that led her to build Proptimal’s “10X Real Estate Analyst.” You’ll hear: 🔎 Why generative models are only as good as the data you feed them — and how to avoid hallucinations. ⚙️ How paid databases can become the secret ingredient for accurate AI summaries that save weeks of research. 🧭 The single career move that beats chasing every trend: specialize and own one strategy. 💡 Why software costs dropped and how “seed-strap” startups are reshaping fundraising and moats. This is a blueprint for operators who want institutional-grade rigor without the VC treadmill. Tune in, rethink your stack, and stop burning midnight hours on spreadsheets. Connect with Lilian on LinkedIn and explore Proptimal’s tools to change how deals get done. #RealEstate #AIForBusiness #CRE #FounderStory #Underwriting #Bootstrapping #DealMaking #ScalingStation #FounderAdvice

    28 min
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About

Scaling Station Podcast features conversations with founders, operators, and leaders rethinking how the built world works. Host Will Rodosky explores the intersection of real estate, technology, and entrepreneurship — uncovering the strategies, setbacks, and stories behind scaling businesses that shape our communities.

Information

  • Creator
    Will Rodosky
  • Years Active
    2K
  • Episodes
    13
  • Rating
    Clean
  • Copyright
    © 2025 Scaling Station Podcast
  • Show Website
    Scaling Station Podcast