Most real estate deals don’t fail because of the deal.

They fail because of capital, structure, and what no one sees behind the scenes.

In this episode, Steven Stein breaks down:

• why deals collapse late
• what lenders actually care about
• and the hidden rules that separate closers from everyone else

If you’re raising capital, structuring deals, or scaling in CRE…

👉 this is the part of the game nobody teaches.

What really determines whether a commercial real estate deal closes… or dies?

In this episode of The AI Edge Podcast, Louis sits down with Steven Stein, President of Capital Markets at Tauro Capital Advisors, to break down what actually happens behind the scenes of debt and equity in today’s market.

Steven has spent decades in commercial real estate across multiple cycles, working on thousands of transactions. His perspective is simple but powerful:

👉 Capital doesn’t just fund deals. It determines whether they survive.

We go deep on:

• Why most deals fall apart late in the process
• The truth about interest rates vs. what actually matters
• How lenders think (and what sponsors miss)
• The hidden risks inside loan covenants
• Why AI helps speed, but not solve, real estate deals
• What separates sponsors who get capital from those who don’t

If you’re an operator, investor, or capital raiser…

This episode will change how you think about deals.

Steven Stein is the President of Capital Markets at Tauro Capital Advisors, a national commercial real estate advisory firm specializing in structured debt and equity across all asset classes.

With a career spanning multiple market cycles and thousands of transactions, Steven has worked across investment sales, leadership, and capital markets. His approach is deeply execution-driven, relationship-led, and focused on solving complex capital challenges for sponsors nationwide.

At Tauro, Steven and his team focus on simplifying capital markets, creating competition among lenders, and structuring solutions that help clients close deals in any market condition.

📌 Connect with Steven Stein
LinkedIn: https://www.linkedin.com/in/stephen-d-stein/

📌 Tauro Capital Advisors
Website: https://www.taurocapital.com

📌 Connect with Louis Fernandes
LinkedIn: https://www.linkedin.com/in/louis-fernandes-011860286/

📌 Book a Discovery Call (AI Systems for Operators)
https://calendly.com/edgepartnersai/ai-edge-podcast

📌 Subscribe to The AI Edge Podcast
YouTube: https://youtube.com/@theaiedgepodcast

Most real estate deals don’t fail because of bad opportunities…

They fail because the system behind the deal breaks.

In this conversation, Matt Hagar exposes where deals actually slow down, why most brokers never scale, and how AI is quietly reshaping the future of commercial real estate faster than the industry can keep up.

Just wrapped a powerful conversation with Matt Hagar, co-founder of AI CRE Partners, on what’s really happening behind the scenes in commercial real estate.

This isn’t surface-level.

This is how deals actually get done… and where they fall apart.

We break down:

• Where deals actually die in the process (it’s not where you think)
• The difference between working in the business vs on the business
• Why most brokers hit a ceiling and can’t scale
• The hidden inefficiencies slowing down deal flow
• How AI is giving smaller, faster operators an edge over legacy firms

If you’re an operator, investor, or building in CRE, this is a conversation you need to hear.

🎧 Watch now and rethink how deals really get done.

Matt Hagar is the Co-Founder and Managing Partner of AI CRE Partners.

With over 15 years in commercial brokerage, Matt has been a top producer, scaled regional brokerage operations, and now leads a platform focused on how AI and systems are reshaping how deals get done.

His edge comes from a non-traditional path, combining deep operational experience with a systems-first mindset that challenges how the industry has always operated.

Connect with Matt Hagar

• LinkedIn: https://www.linkedin.com/in/matt-hagar-sior-ccim-msre-8375a51b/
• Company: AI CRE Partners

Connect with Louis Fernandes

• LinkedIn: https://www.linkedin.com/in/louis-fernandes-011860286/
• Podcast: https://youtube.com/@theaiedgepodcast

Want to optimize your deal flow with AI?
→ Book a call: https://calendly.com/edgepartnersai/ai-edge-podcast

Most people think real estate deals fall apart because of financing…

But right now, deals are dying for a completely different reason…

Insurance.

And if this keeps going… it’s going to reshape the entire housing market.

What if the biggest threat to real estate right now… isn’t interest rates… but insurance?

In this episode of The AI Edge Podcast, Louis sits down with Robert Feldman, CEO and Co-Founder of WoW’s Insurance Services, who has spent nearly three decades in high-risk property insurance.

This conversation goes deeper than insurance.

It exposes a system-level problem affecting:

• Homeowners
• Investors
• Brokers
• Entire real estate transactions

Inside this episode:

• Why insurance is becoming the #1 deal killer in real estate
• How rising premiums are destroying affordability
• The hidden reason property values are starting to drop
• What “fire hardening” is and why it’s becoming mandatory
• Why some homes are becoming completely uninsurable

Robert breaks down what’s actually happening behind the scenes…

and why most operators aren’t prepared for what’s coming next.

If you’re involved in real estate in any way… this is something you need to understand.

LinkedIn: https://www.linkedin.com/in/robertfeldman1/
Company: WoW’s Insurance Services
Website: wowsinsurance.com

YouTube: https://youtube.com/@theaiedgepodcast
Apple: https://podcasts.apple.com/us/podcast/the-ai-edge-podcast-cre-ai/id1867613089
Spotify: https://open.spotify.com/show/1S0tOQ0G68MCoBKbs6xemA
Amazon: https://music.amazon.com/podcasts/1eb1bc13-3a3b-4706-8147-473a0a2ac62b/the-ai-edge-podcast-cre-ai
iHeartRadio: https://iheart.com/podcast/320656102/
Deezer: https://link.deezer.com/s/32pb138lB41qTj51V1F1B
Website: https://theaiedgepodcastcreai.riverside.com/

Today I’ve got Robert Feldman with me, CEO and Co-Founder of WoW’s Insurance Services.

Robert has spent nearly three decades in the insurance world, specializing in high-risk properties and fire zones across the Western United States.

What makes this conversation especially important is this…

When insurance breaks… real estate breaks.

Transactions slow down, financing becomes harder, and property values start getting impacted.

Robert is right in the middle of that shift, helping brokers, homeowners, and investors navigate a market that’s becoming increasingly difficult to insure.

Robert, welcome to the show.

Most real estate deals don’t die because they’re bad…
they die because capital and execution are completely out of sync.

Today’s guest is solving that at a $3.5 trillion level…
and what he’s building could completely change how real estate gets owned.

What if the biggest problem in commercial real estate isn’t deal flow… but broken capital flow?

In this episode of The AI Edge Podcast, Louis sits down with Alex Bell, Founder & CEO of AVKI, who is building the infrastructure layer for tokenized real estate at an institutional level.

This isn’t another crypto conversation.

This is about:

• Why deals fall apart even when they should close
• The disconnect between capital, timing, and execution
• How banks and asset managers will offer fractional real estate ownership
• What “tokenization” actually means in the real world
• Why this shift could impact a $3.5 trillion private CRE market

Alex breaks down how his platform is creating the rails for ownership, liquidity, and access, while staying compliant and aligned with regulators.

If you’re an operator, investor, or developer, this conversation will change how you think about capital, scale, and the future of real estate.

Today I’ve got Alex Bell with me, Founder and CEO, building the infrastructure layer for tokenized real estate at an institutional level.

We’re not talking about hype or marketplaces.

We’re talking about the actual rails, the legal, technical, and compliance systems that allow banks, asset managers, and financial platforms to offer real ownership in real assets.

Alex is focused on solving one of the biggest problems in commercial real estate…

the disconnect between capital and execution.

Alex, welcome to the show.

LinkedIn: https://www.linkedin.com/in/vostretti/
Website: https://www.av-ki.com

Company: AVKI

YouTube: https://youtube.com/@theaiedgepodcast
Apple: https://podcasts.apple.com/us/podcast/the-ai-edge-podcast-cre-ai/id1867613089
Spotify: https://open.spotify.com/show/1S0tOQ0G68MCoBKbs6xemA
Amazon: https://music.amazon.com/podcasts/1eb1bc13-3a3b-4706-8147-473a0a2ac62b/the-ai-edge-podcast-cre-ai
iHeartRadio: https://iheart.com/podcast/320656102/
Deezer: https://link.deezer.com/s/32pb138lB41qTj51V1F1B
Website: https://theaiedgepodcastcreai.riverside.com/

Most real estate deals don’t fail because they’re bad deals…
they fail because capital never shows up.

In this episode, we break down what actually moves money…
and why most operators are getting this completely wrong.

Just wrapped a powerful conversation with Linda Holtz, a real estate development and finance operator with experience across institutional capital, underwriting, and large-scale project execution.

We went deep into what’s actually happening behind the scenes in real estate deals, from capital raising and equity structuring to why so many opportunities never make it across the finish line.

This is not theory. This is how deals actually get done.

If you’re an operator, investor, or builder trying to scale, this conversation will change how you think about capital, execution, and growth.

In this episode, we break down:

• What really determines whether a deal gets funded
• Where most operators lose capital without realizing it
• The hidden bottlenecks in development and deal execution
• How institutional players evaluate risk and opportunity
• Why capital flow, not deal flow, is the real constraint

The AI Edge Podcast is where operators, founders, and investors share how they actually build, scale, and execute in the real world.

🎙 Hosted by Louis Fernandes, Co-Founder of Edge Partners AI

Linda Holtz is a real estate development and finance professional with deep experience across capital structuring, underwriting, and large-scale project execution.

She is the Founder of Save The Chat Group, where she advises developers, family offices, and institutional capital partners on acquisitions, financial structuring, and development strategy.

Linda has worked across hundreds of millions in transactions, including multifamily, student housing, medical office, and mixed-use developments, and has played a key role in underwriting, capital formation, and deal execution at scale.

Her background includes institutional-level underwriting, asset management, and capital markets strategy, giving her a unique perspective on what actually drives successful real estate deals.

https://married2realestate.com/
https://www.linkedin.com/in/linda-holtz-1493495a/

Most founders think hiring is a people problem. It's not. It's a systems problem. And if you're still posting jobs and praying somebody great applies, you're already behind.

Today's guest has placed talent inside startups, PE-backed companies, and scaling operators, and he's here to tell you exactly where most founders get it wrong before they even post the job.

In this episode of the AI Edge Podcast, Louis sits down with Justin Dixon, founder of Hire Tomorrow, to break down what most founders completely get wrong about talent, and why those mistakes compound fast.

Justin has spent his career placing people inside startups, private equity portfolio companies, and scaling operators. He's seen what separates the teams that scale from the ones that stall, and it almost always comes back to hiring decisions made too fast, too late, or with the wrong criteria.

In this conversation, Louis and Justin get into:

• Why trying to hire one person to fill three roles is quietly killing your growth
• The real cost of a bad hire in a startup versus a large company
• How PE-backed operators approach talent differently from everyone else
• What "key man risk" is and why it tanks your valuation at exit
• Where AI is actually helping in recruiting and where it's just hype
• The fake applicant problem flooding job postings right now
• Why your first sales leader hire might be the most important decision you make

If you're a founder, operator, or investor thinking about scaling, this episode will change how you think about people as a business asset.

Subscribe for new episodes every week featuring operators, investors, and founders who are actually building.

GUEST INTRO SECTION

About Justin Dixon

Justin Dixon is the founder of Hire Tomorrow, a boutique recruiting firm that works with startups, private equity firms, and scaling operators to solve one of the hardest problems in business, finding the right people at the right stage.

With nearly two decades of experience across large corporations like Comcast, early-stage startups, and M&A advisory shops, Justin brings an operator's lens to talent strategy. He specializes in helping founders build repeatable hiring systems, navigate PE-backed growth, and think about succession before they need to.

He also hosts the Growth Capital Podcast, where he covers business building, capital, and growth.

Connect with Justin: LinkedIn: https://www.linkedin.com/in/jmdixon15/

Podcast: Growth Capital Podcast (available on all major podcast platforms)

Company: Hire Tomorrow

Most companies don’t fail because of bad tools.
They fail because their processes never evolve.

I’ve seen organizations spend hundreds of thousands of dollars on software that changes nothing.

In this episode, we break down why that happens, and what actually needs to be fixed first.

Most companies think their problem is tools.

It’s not.

It’s process.

In this episode of The AI Edge Podcast, Louis Fernandes sits down with Santiago Cortés, Founder and CEO of Lab Cortex, to break down why organizations waste tens to hundreds of thousands of dollars on software that never delivers results.

This conversation goes deep into what actually breaks inside growing companies:

• Why adding more people stops working
• How poor process design destroys efficiency
• Where automation fails without clear ownership
• Why compliance should speed you up, not slow you down
• The real role of AI in regulated and complex environments

If you’re scaling a business, managing operations, or thinking about AI, this episode will challenge how you think about systems.

AI is not magic.

It’s leverage, but only if the foundation is right.

• Tools don’t fix broken processes
• Hiring more people is not a scalable solution
• Lack of adoption kills most tech investments
• Compliance, done right, accelerates execution
• AI without structure creates risk, not efficiency

LinkedIn: https://www.linkedin.com/in/santiago-cortes/
Website: https://labcortex.com

The AI Edge Podcast features real conversations with operators, founders, and investors building businesses using systems, AI, and execution.

No hype. No theory. Just what actually works.

Santiago Cortés is the Founder and CEO of Lab Cortex, where he helps regulated and mission-driven organizations design process-first systems that scale with clarity, compliance, and control.

With a background in mortgage servicing and operations, Santiago specializes in identifying inefficiencies, restructuring workflows, and implementing automation and AI in a way that actually works in the real world.

His approach is simple:

Start with the process.

Then apply the tools.

What if the real estate crisis never went away, it was just hidden?

In this episode, distressed debt investor Bill Bymel breaks down why banks have been masking real stress in mortgages, how “extend and pretend” has delayed the pain, and why both homeowners and commercial real estate operators may be walking into the next wave blind.

If you care about housing, private credit, commercial real estate, or protecting capital in a shaky market, this conversation will change how you see the cycle.

What’s really happening in mortgages, distressed debt, and commercial real estate right now?

In this episode of The AI Edge Podcast, Louis Fernandes sits down with Bill Bymel, Founder and CEO of First Lien Capital, distressed debt investor, special situations advisor, host of the Debt Doctor Podcast, and author focused on the secondary mortgage market.

Bill pulls back the curtain on what most investors, operators, and even the media are missing:

• Why low default rates may be hiding the real stress in the market
• How “extend and pretend” became the system’s way of delaying pain
• Why lenders avoid foreclosure even when loans are clearly broken
• What actually causes loans to fail in commercial real estate
• How borrowers can create better outcomes before it’s too late
• Where AI can help in servicing, loss mitigation, and decision-making
• Why the next 12 to 24 months may reshape how investors think about risk

This is not a surface-level conversation. It is a real look at how debt markets function when pressure builds, and what smart investors should be watching now.

If you are an operator, lender, investor, or anyone trying to understand where real estate risk is actually building, this episode is for you.

Guest: Bill Bymel
Founder & CEO, First Lien Capital
Host, Debt Doctor Podcast

Subscribe for more conversations with operators, founders, and investors building in real markets.

#RealEstate #DistressedDebt #CommercialRealEstate #MortgageMarket #PrivateCredit #Investing #BillBymel #TheAIEdgePodcast

Today’s guest is Bill Bymel, Founder and CEO of First Lien Capital, a distressed mortgage investment platform focused on acquiring and resolving sub-performing and non-performing mortgages across residential and commercial real estate.

He is also the founder of First Lien Resolutions, a special situations advisory group serving banks and private lenders, host of the Debt Doctor Podcast, and author of Win Revolution, an insider’s guide to investing in the secondary mortgage market.

Bill brings nearly two decades of experience in distressed debt, workouts, servicing, and special situations, with a perspective that cuts through headlines and gets to what is actually happening beneath the surface of the market.

What if you could create $400,000 in value… before you even buy the property?

No renovation. No construction. No risk-heavy development.

Today’s guest has built over $100 million in real estate using one principle:

The money isn’t in the deal…

it’s in the structure.

Most real estate investors are chasing deals.

Cherif Medawar built a $100M+ portfolio by doing something different…

He creates value before he buys.

In this episode of the AI Edge Podcast, Cherif breaks down:

• How he turned a $600K property into $1M instantly
• The exact strategy behind single-tenant triple net deals
• Why most investors struggle with capital raising
• The real difference between syndications vs funds
• How structure creates generational wealth
• The biggest mistakes investors make (and how to avoid them)

This is not theory.

This is real-world deal mechanics from someone who has done it for 35+ years.

If you’re an investor, operator, or builder…

This episode will change how you think about real estate.

🎯 Key Takeaway:

The deal doesn’t make you wealthy.

The structure does.

Cherif Medawar is a commercial real estate investor, fund manager, and educator with over 35 years of experience.

He has:

• Built a portfolio exceeding $100M in real estate
• Launched SEC-filed investment funds
• Trained thousands of investors worldwide
• Specialized in deal structuring, capital raising, and scaling portfolios

Cherif is widely known for his philosophy:

👉 “The money is in the structure.”

🌐 Website: https://www.cmrei.com
📺 YouTube: Search “Cherif Medawar”
📸 Instagram: https://www.instagram.com/cherifmedawar

▶️ YouTube: https://youtube.com/@theaiedgepodcast
🍎 Apple: https://podcasts.apple.com/us/podcast/the-ai-edge-podcast-cre-ai/id1867613089
🎧 Spotify: https://open.spotify.com/show/1S0tOQ0G68MCoBKbs6xemA

Most people think they have an outreach problem.

They don’t.

They have a broken system behind it.

In this episode, we break down how one simple shift took conversion rates from 3% to 21%… without burning trust or spamming people.

Most outreach doesn’t fail because of effort.

It fails because the system behind it is broken.

In this episode of The AI Edge Podcast, Louis Fernandes sits down with Troy Hipolito, founder of Troy Agency and creator of Skoop, to break down how relationship-driven systems outperform brute force outreach every time.

This is not about scripts, hacks, or sending more messages.

It’s about structure, timing, and building a system that creates a buying environment instead of forcing a sale.

Inside this conversation:

• Why “more outreach” actually kills conversions
• The 3% → 21% conversion shift using simple video + context
• How to build multi-channel systems that work together
• Why most founders are selling the wrong thing (and don’t realize it)
• The difference between automation that scales vs. automation that destroys trust
• How to turn content, email, events, and DMs into one unified pipeline

If you’re a founder, operator, or sales leader trying to scale without burning your market, this episode will change how you think about outreach, systems, and conversion.

🎯 This is for people who want real results, not noise.

Guest: Troy Hipolito

Founder of Troy Agency and creator of Skoop, Troy specializes in building multi-channel relationship systems that help founders and operators scale outreach without sacrificing trust.

With a background in systems, gamification, and software development, Troy has helped businesses move from inconsistent deal flow to predictable, relationship-driven pipelines.

His approach focuses on structure, human connection, and transformation, not just tools or tactics.

🔗 Connect with Troy on LinkedIn:
https://www.linkedin.com/in/troyhipolito/

🌐 Learn more about Skoop:
https://skoopapp.com