The Julian Castle Show

In this episode, Jordan Santiago breaks down how he went from googling “how to make $1M a year” to building a remote wholesaling machine with no college degree, no rich family, and no Wall Street job.

We get into:

• Why he quit baseball, dropped out, and fell into a dark, directionless period

• The “meant for more” feeling and how he used it instead of numbing it

• His first $2,000 wholesale check from a Craigslist JV (and why it felt like $2M)

• Pivoting out of brutal NYC deals into New Jersey and hitting his first $14k assignment

• How he bootstrapped SMS marketing by literally cashing cans for ad money

• The exact years he made $0, $7.5k, $5k… then finally cracked six figures

• Losing over $100k on bad multifamily buys and rebuilding from the damage

• How he does deals remotely today and what he’d do if he had to start over

If you’re a wholesaler, agent, or just a restless 9–5er who feels “meant for more,” this one will hit home.

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Connect with Jordan Santiago:

Instagram: ⁠https://www.instagram.com/thejordansantiago/?hl=en⁠

X: ⁠https://x.com/TheJSantiago?lang=en⁠

YouTube: ⁠https://www.youtube.com/@TheJordanSantiago_⁠

Facebook: ⁠https://www.facebook.com/jordan.santiago.731/⁠

CONNECT WITH JULIAN:

• Facebook: ⁠⁠https://www.facebook.com/juliancastlex/⁠⁠

• Instagram: ⁠⁠https://www.instagram.com/juliancastlex/⁠⁠

• TikTok: ⁠⁠https://vm.tiktok.com/ZSNdd8Trr/⁠⁠

• Twitter/X: ⁠⁠https://x.com/juliancastlex⁠⁠

• LinkedIn: ⁠⁠https://www.linkedin.com/in/juliancastle/⁠⁠

Business Inquiries: ⁠⁠[email protected]⁠

If you're doing distressed real estate and every deal feels like a coin flip, you have no idea if it will actually close, or you constantly find yourself walking away from a "messy" deal because the title is clouded, the insurance claim was denied, or the seller's situation feels way too complicated—this episode is for you.

In this episode, we break down:

• Eliminate the Guesswork: A reliable framework to see exactly what is driving each distressed deal so you are never blindsided at the closing table.
• The 3-Step Situation Audit: How to evaluate complex roadblocks (bad title, insurance denials, looming foreclosure, and family disputes) before you ever put an offer in writing.
• Hidden Profit Centers: Spot liens, botched probate/successions, and denied claims that most competitors run away from—and turn those exact problems into major spreads.
• Creative Underwriting: A practical approach to structuring terms that directly expands the pool of deals you can actually fund and close.
• Real-World Case Studies: Transparent numbers from three of my own deals, including how I kept a $150,000 promise alive straight through a government shutdown.
• The 3 Deal Filters: Simple rules of thumb you can apply to your next lead to capture overlooked equity and avoid getting burned by bad files.

If you are ready to stop treating distressed investing like a gamble, tune in to master the mechanics behind closing complex, high-profit real estate deals.

CONNECT WITH JULIAN:

• Facebook: https://www.facebook.com/juliancastlex/
• Instagram: https://www.instagram.com/juliancastlex/
• TikTok: https://vm.tiktok.com/ZSNdd8Trr/
• Twitter/X: https://x.com/juliancastlex
• LinkedIn: https://www.linkedin.com/in/juliancastle/

Business Inquiries: [email protected]

If you want to build real wealth, you need to know how to stop chasing hype and start thinking like an operator.

And that’s what you’ll be learning in this video.

Today, I break down the mindset and skills that helped me go from flipping Jordans to working on distressed real estate deals and building businesses that can operate without me.

You’ll understand:

- The most important things to know when starting out

- How to spot underpriced opportunities

- How to identify spreads, negotiate better deals, and develop skills that can be applied across different industries and asset classes

- The risks associated with jumping from one business model to another

- How to create and compound more value and opportunities using what you already have instead of always chasing the next big idea

- My complete “whole deal method” and everything I learned from the most difficult periods of my journey

- The five key components for rescuing deals that appear to be dead and creating better outcomes for everyone involved

You’ll also understand how to turn your skills into systems and systems into machines that keep you from being the person who has to personally make everything happen.

Watch till the end if you want to learn how to identify hidden opportunities, develop valuable skills, solve bigger problems, build repeatable systems, and create the foundation for wealth that can compound over time.

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Business Email: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠[email protected]⁠⁠

In this episode, we go deep into how Tim Serpe turned City Atlas into a dispo machine and how the new version of SellSide is helping his team analyze and move deals faster than ever.

Tim reveals:

• How SellSide’s new AI + deal analyzers work across wholesale, novation, fix & flip, BRRRR, turnkey, creative, and buy & hold

• How his reps underwrite deals before the call and tailor the pitch to three buyer avatars: retail, investor, institutional

• Why his acquisitions reps now own the deal from first call through closing (and how that fixed the “he said / she said” chaos between Acq and Dispo)

• How they’re doing 95% novations, 5% wholesale in a flattening market

• The exact handoff from “contract signed” to “seller welcome call” to MLS / dispo

• Why most wholesalers’ contract-to-close is shrinking, and what to change so more of your signed contracts actually fund

If you’re wholesaling, doing novations, or trying to close more of the deals you already have, this is a complete dispo playbook you can implement immediately.

Resources & Links:

• SellSide: https://sellside.io (Use code JULIANCASTLE20 at checkout for 20% off)

• Get a Cash Offer on Your Property: https://www.goldenkeyoffer.com

  
  

Connect with Tim Serpe:

• Website: https://citiatlas.com (also check https://cityatlas.com)

• Instagram: https://www.instagram.com/timserpe/

• LinkedIn: https://www.linkedin.com/in/timserpe

• Facebook: https://www.facebook.com/share/1GLBpHEdBq/

  
  

Connect with Julian Castle:

• YouTube: https://youtube.com/@juliancastlex

• Instagram: https://www.instagram.com/juliancastlex

• Facebook: https://www.facebook.com/share/17xfN7YPrL/

In this episode, I talk with Alessandro Lima, a commercial real estate broker in Miami.

Alessandro shares how he:
• Failed the real estate exam 7 times before passing.
• Sold cars and motorcycles before ever getting into commercial real estate.
• Went from an $897 paycheck to closing a $1.5 million deal with a bank.
• Uses owner lists and cold calls to find mobile home parks and other properties.
• Structures his day around working out and calling property owners.

If you work in residential real estate (wholesaling, flips, rentals) and want to see what the real life of someone selling commercial properties in Miami looks like, this episode shows you the truth.

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Connect with Alessandro Lima
LinkedIn: https://www.linkedin.com/in/alessandro-lima-52b322117
Instagram: https://www.instagram.com/isellbuildings/
Facebook: https://www.facebook.com/share/1EGqwJc4g1/

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Connect with Julian:
Instagram: https://www.instagram.com/juliancastlex
Facebook: https://www.facebook.com/share/17xfN7YPrL/
YouTube: https://youtube.com/@juliancastlex

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Subscribe for more conversations on real estate, money, and operator‑level execution.

If you’re trying to scale into bigger commercial real estate deals but you’re guessing what lenders want, this episode is your shortcut.

Rachel Garcia is a former corporate banking executive (Bank of America, Wells Fargo, JPMorgan) who left to start her own commercial loan brokerage, CRE Capital Investments, and then built CRE Capital Finders: AI software that underwrites your deal, scores funding probability, and matches you to 15,000+ lenders in seconds.

In this conversation, we cover:
• Why most banks automatically decline the deals investors actually want
• How Rachel’s software analyzes DSCR, LTV, sponsor strength, and market risk in minutes
• The biggest mistakes residential loan officers make when they jump into commercial
• How investors, brokers, and realtors can use AI underwriting to stop wasting months on dead deals
• Where Rachel sees real opportunity in today’s commercial market

If you want to stop wasting months chasing lenders who were never going to fund your deal, watch this episode and learn how to evaluate your commercial real estate deals like a banker, increase your chances of approval, and find the right lenders before you submit a single application.

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CRE Capital Finders (AI Underwriting & Lender Matching):
https://app.crecapitalfinders.com/

CRE Capital Finders Community & Coaching:
https://tools.crecapitalfinders.com/residential/

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Connect with Rachel Garcia:
• Website: https://crecapitalinvestments.com/
• LinkedIn: https://www.linkedin.com/in/rachel-garcia-83695564/
• Instagram: https://www.instagram.com/cre_capital/

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Connect with Julian:
• Instagram: https://www.instagram.com/juliancastlex/
• Facebook: https://www.facebook.com/juliancastlex/
• TikTok: https://www.tiktok.com/@juliancastlex
• Twitter / X: https://twitter.com/juliancastlex
• LinkedIn: https://www.linkedin.com/in/juliancastle/
• Business Email: [email protected]

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Subscribe for more conversations on real estate, money, and operator‑level execution.

If you think “affordable housing” means bad returns or slumlord tactics, this episode will change your mind.

Leo Young went from an immigrant kid who starved himself to buy toys… to the #1 Tesla salesperson… to operating 600+ manufactured housing units across 8 states as founder of Cornell Communities.

In this conversation, Leo joins me to break down exactly how he finds and fixes neglected mobile home parks, upgrades infrastructure, keeps rents reasonable, and still delivers strong risk‑adjusted returns to investors.

In this episode, you will understand:
• Why mom‑and‑pop owners let parks rot and how Leo fixes what they ignored
• The first 3 upgrades he makes in every community (before touching rents)
• How he underwrites CapEx, roads, utilities, and infill without blowing up returns
• The Tesla sales habits that turned an introvert into a top closer
• The one “spreadsheet move” he refuses to make, even though it boosts IRR

If you're an investor tired of choosing between "safe but boring" and "high returns but sketchy," this episode is a playbook for building wealth in an overlooked asset class the right way.

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Connect with Leo Young (Cornell Communities):
• Website: https://leoyoungrealestate.com/
• LinkedIn: https://www.linkedin.com/in/leo-young/
• Instagram: https://www.instagram.com/leoyoungrealestate/

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Connect with Julian:
• YouTube: https://youtube.com/@juliancastlex
• Instagram: https://www.instagram.com/juliancastlex/
• Facebook: https://www.facebook.com/juliancastlex/
• TikTok: https://www.tiktok.com/@juliancastlex
• Twitter / X: https://twitter.com/juliancastlex
• LinkedIn: https://www.linkedin.com/in/juliancastle/
• Business Email: [email protected]

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Subscribe for more conversations on real estate, money, and operator‑level execution.

If you are only making money on deeply distressed sellers, you are leaving 91% of your leads on the table.

In this episode, Tim Serpe (founder of City Atlas & Sellside) breaks down how he did 250+ transactions in 16 months across 25 states using a system of three offers (cash, novation, and retail) plus a lean agent network and a pricing app that lets his reps lock deals on the first call.

In this episode you'll learn:
• How Tim survived 2008, discovered wholesaling, and built a portfolio of 24 creative deals before going nationwide.
• Why "cash offers" are now the most expensive option for sellers (a 30 to 50 percent haircut) and how he uses that truth in his script.
• The exact three offer framework he uses on every seller: cash, private client (novation), and retail buyer service.
• How to list properties without a license using entry only MLS services and a relocation/listing management fee.
• How Tim built a nationwide agent partner network and does dispo with almost no internal dispo team.
• The Sellside app: compressing underwriting from 3 calls to 1 and letting pure sales killers make offers without comping houses.
• Tim's controversial commission plan of 80 to 100 percent and lead success fee that lets part time reps make $40k to $90k.

If you're a wholesaler or novation operator who wants to monetize more of your leads and stop throwing away "not distressed enough" sellers, this episode is a playbook.

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Connect with Tim Serpe:
• Website: https://citiatlas.com/
• Instagram: https://www.instagram.com/timserpe/
• LinkedIn: https://www.linkedin.com/in/timserpe/
• Facebook: https://www.facebook.com/share/1GLBpHEdBq/

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Connect with Julian:
• YouTube: https://youtube.com/@juliancastlex
• Instagram: https://www.instagram.com/juliancastlex/
• Facebook: https://www.facebook.com/juliancastlex/
• TikTok: https://www.tiktok.com/@juliancastlex
• Twitter / X: https://twitter.com/juliancastlex
• LinkedIn: https://www.linkedin.com/in/juliancastle/
• Business Email: [email protected]

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Subscribe for more conversations on real estate, money, and operator‑level execution.

If you’re a wholesaler or active investor who wants guaranteed HUD-backed rent and long-term cash flow, this episode gives you Tom Cruz’s exact Section 8 playbook.

Tom went from selling $149/month WordPress sites in college… to wholesaling… to owning 819+ Section 8 units that net about $1.3M/month with no partners and no debt. In this conversation, he walks Julian step-by-step through how he’d build that portfolio again today.

In this episode, you will learn:
• How Tom stumbled into Section 8 by accident and realized vouchers beat wholesaling for long-term wealth
• The real math: why Section 8 checks often pay above market rent and how Tom consistently hits ~30% cash-on-cash returns
• The 3–5 unit “proof of concept” phase and how to use it to attract serious investor capital
• Exact terms from his early partnerships (including a $250K+ investor and a 92-unit deal) and how he later bought everyone out
• How to pick profitable markets (landlord-friendly states, FMRs, taxes, crime, insurance) and which ones to avoid
• Why he stopped caring about “buying under value” and focused on speed and rent roll instead
• The structure of his property management machine: 11 full-time PMs across 4 states and a simple weekly meeting rhythm
• How he creates his own “mini-portfolios” instead of buying giant mixed-quality packages
• The 4-6 week plan he gives mentees to go from zero to first Section 8 check
• How he adds ~$80K/month in profit just from optional amenities (washers/dryers, ceiling fans, landscaping, etc.)
• What separates his best students from the ones who never buy a single property
• Financing options from FHA and seller finance to DSCR and small local banks
• Why most people overcomplicate their first deal and how to avoid common Section 8 mistakes (tenant selection, old houses, bad layouts)
• Why he thinks you can compress what took him a decade into ~5 years if you use mentors, software, and AI instead of trial and error

If you’re serious about building a portfolio of government-backed, cash-flowing rentals, this episode is basically a free masterclass.

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Connect with Tom Cruz:
• Website & Mentorship: https://tomcruz.com/
• Instagram: https://www.instagram.com/tcruznc/

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Connect with Julian:
• YouTube: https://youtube.com/@juliancastlex
• Instagram: https://www.instagram.com/juliancastlex/
• Facebook: https://www.facebook.com/juliancastlex/
• TikTok: https://www.tiktok.com/@juliancastlex
• Twitter / X: https://twitter.com/juliancastlex
• LinkedIn: https://www.linkedin.com/in/juliancastle/
• Business Email: [email protected]

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If you got value from this, subscribe to The Julian Castle Show, drop a comment with your biggest takeaway, and share this with someone who needs a real, non-guru real estate game.

Ex-MMA Fighter To $70M Realtor: Tim Stout On Outworking Lazy Competition & Selling 100 Homes/YearToday’s guest went from getting punched in the face for a living to leading a $70M+ real estate machine while coaching agents to sell 100 homes a year.  Tim Stout is a retired pro MMA fighter, Brazilian Jiu jitsu black belt, real estate team leader, self-defense creator with a 1M+ audience, and author of “Forged in Fire” and “How to Sell 100 Homes a Year.”  In this episode, Tim joins me to break down: 

• How growing up poor in the Appalachian Mountains and fighting for everything shaped Tim’s work ethic 

• The moment he knew fighting couldn’t be the long-term plan 

• Going from 16 deals in 6 months to 100+ deals a year as a solo agent 

• The “pizza” framework he used to build a 300+ deals/year team 

• Time-blocking and prospecting from 9–12 that agents refuse to do 

• Why most agents never escape mediocrity (and the lies they tell themselves) 

• Building a 1M+ following teaching simple self-defense online 

• Masculinity, confidence, and why men need hard things and hard rooms 

• How to pick the right coach and actually use what you’re learning  If you’re in real estate, sales, or just tired of feeling behind, this conversation will punch you in the mouth (in a good way) and give you a clear playbook to outwork your competition.  

Connect with Tim Stout: 

Website: https://www.thetimstout.com/

Instagram: https://www.instagram.com/TheTimStout

Facebook: https://www.facebook.com/TheTimStout/

If this episode hit home, subscribe and share it with one person who needs to understand how lazy their competition is.

FOLLOW Julian:

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Business Email: ⁠⁠⁠⁠⁠⁠⁠⁠⁠[email protected]⁠⁠