The AI Edge Podcast: CRE & AI

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

Most business owners think rising healthcare costs and payroll taxes are just part of the game. Dr. Sean Wilson says that’s wrong. In this episode, he breaks down the silent tax leak quietly draining cash from organizations every pay period, and explains how companies can improve employee benefits, reduce payroll tax burden, and keep more money in the business without slashing headcount or spending more.

What if your business is overpaying payroll taxes every single pay period and you do not even realize it?

In this episode of The AI Edge Podcast, Louis Fernandes sits down with Dr. Sean Wilson, founder of Manoah Consulting, to unpack what he calls the silent tax leak, the hidden dollars many organizations lose through outdated payroll and benefits structures.

Sean explains how companies can redesign their benefits strategy to improve employee healthcare access, reduce payroll tax expense, and increase take-home pay for employees, often without increasing total spend.

This conversation is especially valuable for:

• business owners
• CFOs
• HR leaders
• nonprofit executives
• school systems
• municipalities
• operators trying to control rising healthcare costs without hurting people

Sean also shares:

• the most common myths leaders believe about payroll taxes and benefits
• why smart organizations still miss these savings
• how benefits impact trust, retention, and employee morale
• where AI and automation are already improving enrollment, access, and communication
• what great leaders do differently when margins get tight

If you are squeezed by healthcare costs, payroll tax burden, and pressure to do more with less, this episode is worth your time.

Connect with Dr. Sean Wilson:
Website: thesavings.manoahconsulting.com
Phone: 817-271-7766

Guest Introduction
Today’s guest is Dr. Sean Wilson, founder of Manoah Consulting. Sean helps organizations uncover what he calls the silent tax leak, hidden payroll tax dollars that quietly drain margin year after year.

He works with business leaders, nonprofits, municipalities, and schools to redesign benefits in a way that improves employee healthcare access while lowering costs for the employer.

If you have ever felt trapped between rising benefits expense and taking care of your people, this conversation is going to hit home.

Most real estate sponsors make the same fatal mistake when pitching investors.

They only talk about the upside.

But according to acquisitions and capital markets expert Eitan Holder, the fastest way to lose investor trust is pretending there’s no downside.

In this episode of The AI Edge Podcast, Louis Fernandes sits down with Eitan Holder to break down the real mindset behind winning deals, raising capital, and underwriting commercial real estate with conviction.

Most sponsors focus on selling the upside.

The best operators earn trust by being honest about the risks.

In this episode of The AI Edge Podcast, Louis Fernandes speaks with Eitan Holder, a commercial real estate acquisitions and capital markets operator responsible for sourcing deals, raising capital, and managing assets across retail and industrial properties in major U.S. markets.

Eitan recently helped close Lakeshore Plaza in West Palm Beach, and in this conversation he breaks down what actually separates operators who win deals from those who simply analyze them.

This discussion covers underwriting discipline, certainty of close, investor psychology, and how AI may reshape acquisitions over the next few years.

Key topics include:

• The mindset required to win competitive deals
• How conviction shows up in negotiations with sellers
• Why sophisticated LP investors care most about track record
• The biggest mistakes sponsors make when presenting deals
• Why retail visibility doesn’t always equal customers
• How underwriting discipline creates certainty of close
• The role AI may play in acquisitions and deal analytics

If you’re a commercial real estate operator, investor, or capital allocator, this episode offers a rare look at how disciplined dealmakers actually think.

About the Guest

Eitan Holder is a commercial real estate acquisitions and capital markets professional focused on sourcing deals, raising investor capital, and supervising asset management across retail and industrial assets in major U.S. markets.

He recently helped close Lakeshore Plaza in West Palm Beach, and specializes in connecting institutional-quality opportunities with investor capital while applying deep underwriting discipline and market analysis.

Eitan is known for his operator-first perspective on acquisitions, conviction in deal structuring, and transparency with investors around both upside and risk.

Connect with Eitan Holder on LinkedIn. https://www.linkedin.com/in/eitan-holder/

What actually separates operators who survive hard markets from those who disappear?

In this episode, John Crossman breaks down the leadership habits, resilience, discipline, and people-first mindset that matter most in commercial real estate, especially when markets get uncertain.

What does it really take to lead through uncertainty in commercial real estate?

In this episode of The AI Edge Podcast, Louis Fernandes sits down with John Crossman, President of Crossman Services, speaker, author, mentor, and longtime CRE operator, for a powerful conversation on leadership, resilience, disciplined decision making, market cycles, team building, mental health, and long-term success in commercial real estate.

John shares how he got started in CRE, the hard lessons that shaped him, what resilience really looks like in down markets, how great leaders think under pressure, where the real opportunities are today, and why relationships, empathy, and showing up still matter more than ever.

This is not just a conversation about deals. It is a conversation about how to lead, grow, and finish well.

In this episode, we cover:

• How John got started in commercial real estate
• The mindset that helped him survive brutal market cycles
• Why resilience matters for every CRE operator
• The leadership mistakes executives make
• How great investors evaluate risk
• What younger investors are getting wrong today
• Where the real opportunities are in the current market
• Why relationships still drive real estate success
• How AI can help in CRE without replacing the human side
• The career advice that helped shape John’s success

If you are a commercial real estate operator, investor, broker, founder, or leader trying to grow through uncertainty, this episode is for you.

Guest intro

John Crossman is the President of Crossman Services, a commercial real estate advisory, brokerage, and investment firm based in Central Florida.

He has spent more than three decades in commercial real estate, building teams, advising clients, navigating multiple market cycles, and mentoring the next generation of industry leaders. Beyond real estate, John is also a speaker, author, leadership coach, and host of The Crossman Conversation.

Most people think land deals are simple. Bill Eshenbaugh explains why they can take years, why sellers still refuse to cut prices, and what actually kills deals before they close.

Bill Eshenbaugh has spent decades in Florida land brokerage, through boom cycles, crashes, government slowdowns, and complex entitlement battles. In this episode, he breaks down what really moves land deals and what most investors still get wrong.

In this episode of The AI Edge Podcast, Louis Fernandes sits down with Bill Eshenbaugh, founder and senior advisor at Eshenbaugh Land Company, to unpack the real-world complexity behind land brokerage, entitlements, market cycles, and long-hold seller psychology in Florida.

Bill has spent decades at the center of major land deals in the Tampa Bay market and has seen what happens when liquidity disappears, regulations tighten, insurance costs rise, and development timelines stretch from months into years.

This conversation goes deep into what actually drives value in land, why so many deals stall, what hidden risks most buyers miss, and why relationships still matter more than ever in a world rushing toward automation.

They also discuss Florida growth, infrastructure pressure, transportation, insurance, political risk, legacy projects like hospitals and history centers, and how technology and AI may help the land business without replacing the human judgment it still requires.

If you are a land investor, developer, broker, builder, or operator trying to understand where the Florida market is really headed, this episode is packed with hard-earned insight.

• Why Florida land deals can take 24 to 36 months
• Why sellers still resist major price reductions
• The hidden deal killers buyers often miss
• How entitlement, zoning, title, and environmental issues delay closings
• What Bill learned from the RTC era and past market crashes
• Why relationships still drive land brokerage
• How to think about roads, utilities, and future value
• What AI can and cannot replace in land deals
• Why Florida cattle country and development are more connected than people think

Today’s guest is Bill Eshenbaugh, founder and senior advisor at Eshenbaugh Land Company, one of the most respected land brokerage and advisory firms in the Tampa Bay market.

Bill holds both the CCIM and ALC designations, has worked through multiple market cycles, served during the RTC era, and has been involved in major land transactions and legacy projects across Florida for decades. He also recently released his historical novel, Up to Shenandoah.

• Email: [email protected]
• Book: Up to Shenandoah, available on Amazon

If you enjoyed this episode, subscribe to The AI Edge Podcast, like the video, and share it with an operator, investor, or developer who wants the real truth about land cycles and getting deals done.

• Bill Eshenbaugh
• Florida land deals
• Florida land investing
• land brokerage
• land entitlement
• Tampa real estate
• Tampa land broker
• land development Florida
• commercial real estate Florida
• Florida development
• entitlement process
• zoning and land use
• market cycles real estate

#CommercialRealEstate #LandDevelopment #FloridaRealEstate #LandBrokerage #AIEdgePodcast

Most CEOs do not fail because they lack vision.
They get stuck because the business starts growing faster than the systems behind it.

In this episode, Carol Schultz breaks down why founders become the bottleneck, why delegation often fails, and how the right Chief of Staff model can help CEOs reclaim leverage, reduce chaos, and get back to leading the company instead of drowning in it.

What happens when the CEO becomes the bottleneck?

In this episode of The AI Edge Podcast, Louis Fernandes sits down with Carol Schultz, Founder and CEO of Vertical Elevation, bestselling author of Powered by People, and host of the Evolving Your Workplace Podcast.

Carol helps CEOs escape operational overwhelm through her Chief of Staff Scaffold System, a model designed to help founders step out of the weeds, regain leverage, and build companies that can grow without everything depending on them.

This conversation goes deep into the real reasons delegation breaks down, why so many leaders stay trapped in meetings and people management, and how blind spots inside the business keep CEOs from scaling effectively.

You’ll also hear Carol’s perspective on founder syndrome, executive coaching, leadership development, talent strategy, AI risk, and what separates companies that thrive from companies that stall.

If you are a founder, CEO, or operator who feels like the business cannot move without you, this episode will hit home.

• Why CEOs become the bottleneck
• Early warning signs a founder is trapped in the business
• Why delegation breaks down
• The difference between an Executive Assistant, Chief of Staff, and COO
• Carol’s Chief of Staff Scaffold System
• The hidden 20 to 25 percent CEOs cannot see from the outside
• How to build a culture of feedback
• What strong operators do differently
• Where AI helps leaders, and where it becomes dangerous

Connect with Carol Schultz at VerticalElevation.com and on LinkedIn.

If you enjoyed this episode, subscribe to The AI Edge Podcast, share it with a founder or operator, and stay tuned for more conversations on leadership, systems, AI, and operational growth.

Today’s guest is Carol Schultz, Founder and CEO of Vertical Elevation, bestselling author of Powered by People, and host of the Evolving Your Workplace Podcast.

Carol has spent more than three decades working with startups, founders, and executive teams, helping leaders build stronger companies through better talent strategy, leadership development, and operational clarity.

Her work today centers on helping CEOs reclaim leverage through her Chief of Staff Scaffold System, a structured model that helps founders get out of the weeds, reduce chaos, and scale without becoming the bottleneck.