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

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

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

In this episode, host Will Rodosky sits down with Harold Hofer, Co-Founder & CEO of Alture Funds, a Newport Beach-based platform giving everyday investors access to large-scale alternative investments.

Harold shares the story of launching Rich Uncles in 2012, taking it public (now Motive, NYSE: MDIV), and why the Jobs Act and digital platforms changed everything.

We dive into:

• Why traditional wealth managers are losing ground to self-directed investors
• How Alture Funds partners with legacy sponsors like Blue Rock
• The rise of private credit and real estate funds accessible with as little as $2,500
• Why the direct-to-consumer market for alternatives could grow from $80B today to $200B+ by 2035
• Lessons learned from disrupting one industry and doing it all over again

👉 Learn more about Alture Funds: https://www.alturefunds.com
👉 Connect with Harold on LinkedIn: https://www.linkedin.com/in/haroldhofer/
👉 Follow Scaling Station: https://www.linkedin.com/company/scalingst...

If you enjoy this conversation, make sure to like, comment, and subscribe for more episodes with the founders and innovators shaping the future of real estate and investments.

#ScalingStation #PropTech #AlternativeInvesting #PrivateCredit #RealEstateInvesting #FinTech

🚀 In this episode of The Scaling Station Pod, we sit down with Kal Merhi, Founder & CEO of iROOMit, the platform transforming how people find safe, affordable housing and roommates worldwide.

From starting in Canada with just $2 to building one of the fastest-growing roommate platforms, Kal shares his journey, the challenges in today’s rental market, and how iROOMit uses AI and strict verification to eliminate scams and create a trusted community.

🌍 With iROOMit already expanding across multiple countries, Kal’s mission is clear: make finding a home as seamless, safe, and empowering as booking a trip on Airbnb.

👉 Tune in to hear how iROOMit is scaling globally, why culture and care drive their success, and what’s next for the platform changing the future of co-living.

What if your dream vacation home no longer meant a lifetime of upkeep, guilt, and empty weeks?

Adam Capes, Founder and CEO at Go Forth, pulls back the curtain on how fractional home ownership being reinvented—so you keep the memories without owning the headache.

From running a magazine to building destination clubs, Adam traces the moment a Danish model changed everything and forced a pivot: availability is the real luxury. In this episode of Scaling Station he reveals the tactics that solve it—matching owners by dates, limiting ownership stakes, and even guaranteeing peak holiday weeks.

Highlights you can’t miss:

🧭 The Danish idea that inspired a simpler, fairer split—and why 4 owners beats 21
🔒 The Peak-Date Guarantee that eliminates booking fights
💸 How branded residences can jump 50–100% in value during construction
🔁 Why fractional ownership can generate recurring rental revenue and portfolio access
✈️ The NetJets analogy for second homes—when sharing makes more sense than buying solo

Want to stop overpaying for underused homes and actually use the places you love? Visit goforthglobal.com to explore discovery calls and trips. Don’t just watch—rethink how you own memories.

#FractionalRealEstate #SecondHome #PropTech #GoForth #ScalingStation #BrandedResidences #TravelSmart #VacationOwnership

Robert Dell’Osso, President of MasterKey Property Management, joins Scaling Station to share how he grew the firm from 35 doors to over 500.

We dive into the power of community-driven property management, why local expertise beats national brands, and what investors need to know about scaling smart in North Carolina’s Triangle market.

🔗 Learn more about MasterKey PM: masterkeypm.com
📌 Connect with Robert on LinkedIn: https://www.linkedin.com/in/robertdellosso/

If you’re an investor or landlord looking to scale with the right partner, this episode is packed with insights you won’t want to miss.

In this episode of the Scaling Station Podcast, I sit down with Pedro Chiesa, CEO of Dedalabs (https://www.dedalabs.com), to explore how AI is transforming customer communication in real estate.

We discuss:

• Why silence is the biggest killer of customer trust
• How virtual agents can create 24/7 customer engagement
• The future of AI adoption in real estate and property management
• Pedro’s journey building Dedalabs and lessons for founders

These AI-powered virtual agents truly help real estate companies handle more interactions while improving client satisfaction + reducing costs.

🔗 Learn more about Dedalabs: https://www.dedalabs.com and follow Pedro's LinkedIn: https://www.linkedin.com/in/pedroichiesa/

🎙️ Follow the Scaling Station Podcast for more conversations with PropTech & real estate leaders.

📌 Connect with me on LinkedIn: https://www.linkedin.com/in/willrodosky/

#RealEstate #PropTech #AI #ScalingStationPodcast