Best Straight Up Chicago Investor Podcasts (2025)

1
Episode 386: How to Invest in DuPage County with Katie and Rob Hayes 1:06:44

5d ago1:06:44

1:06:44

Properties for Sale on the North Side? We want to buy them. Email: [email protected] Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow…

1
Episode 385: What is a Demand Letter and How to Handle Receipt of a Demand Letter 16:24

7d ago16:24

16:24

Properties for Sale on the North Side? We want to buy them. Email: [email protected] Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow…

1
Episode 384: From Cold Calling to Billions of Dollars in Loans Originated with Jake Clopton 54:10

12d ago54:10

54:10

Properties for Sale on the North Side? We want to buy them. Email: [email protected] Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow…

1
Episode 383: From Chemist to Chicago’s “Bow Tie” Attorney w/Mahmoud Faisal Elkhatib 1:01:32

19d ago1:01:32

1:01:32

Properties for Sale on the North Side? We want to buy them. Email: [email protected] Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow…

1
🔥Our Season Finale: You Think You’ve Heard It All? Think Again.🔥 11:23

21d ago11:23

11:23

Text For Some Good Game Sadly, This Is Our Season Finale. This week’s episode is not for the faint of heart. Just when you thought the stories couldn’t get wilder… they did. When 2/3s of the questions come straight from the voicemail section of letmepullyourcoat.com, you know it’s about to get real. From family betrayal to street-level confessions,…

1
Episode 382: What Investors Need to Know About Built to Rent Opportunities in Chicago 16:47

21d ago16:47

16:47

Properties for Sale on the North Side? We want to buy them. Email: [email protected] Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow…

1
🔥 TRAILER: You Think You’ve Heard It All? Think Again. 🔥 2:06

26d ago2:06

2:06

Text For Some Good Game (LOW LIT BLUES LICENSE CODE: YRTWXMAPPI6QY8BW) 🔥SEASON FINALE🔥 This week, 2/3s of the wildest questions came straight from the voicemail box at LetMePullYourCoat.com. And the heat? Unmatched. 🎤 A man just found out his ex-girlfriend was abusing his mother — and now he's on the edge of doing something that could cost him his …

1
Episode 381: How Chicago’s Powerhouse Lender Renovo Financial Was Built with Kevin Werner 1:11:05

26d ago1:11:05

1:11:05

Properties for Sale on the North Side? We want to buy them. Email: [email protected] Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow…

1
He Couldn’t Handle a Real Woman — So He Tried to Break Her 9:55

28d ago9:55

9:55

Text For Some Good Game NEW WEBSITE:WWW.LETMEPULLYOURCOAT.COM This week, it's all about the ladies and it's WOMEN ONLY. It’s all China Doll — raw, real, and straight with no chaser. She’s breaking down what too many women know too well: the pain of loving a man who can’t handle your power. From toxic relationships to fake “alpha males,” insecure lo…

1
Preview For "He Couldn’t Handle a Real Woman — So He Tried to Break Her" 1:30

1M ago1:30

1:30

Text For Some Good Game 🔥 In this episode, China Doll pulls the coat on: * Loving a man who hates your independence * Why insecure men chase powerful women * Friends who envy your growth but wear smiles * Co-parenting with a narcissist * What to do when you’ve outgrown your circle * Being loyal to a man who never deserved you Get ready for laughter…

1
Episode 380: Innovation in Modular Housing With Rory Rubin 33:25

1M ago33:25

33:25

Properties for Sale on the North Side? We want to buy them. Email: [email protected] Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow…

1
Family Will F*k You Up If You Let 'Em 12:14

1M ago12:14

12:14

Text For Some Good Game License Code For 'Low Lit Blues' :FNRKQCFVJMPDTVOE This week on Let Me Pull Your Coat: The Unfiltered World of Master Silk, China Doll dives deep into the dark truth families don’t want exposed. Because sometimes, the most dangerous betrayal comes from the people sitting at your own table. We’re pulling coats on: Mothers who…

1
Episode 379: Preparing Your Property To Add an ADU 12:25

1M ago12:25

12:25

Properties for Sale on the North Side? We want to buy them. Email: [email protected] Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow…

1
Preview for 'Family Will 'F' You Up, If You Let Them' 1:59

1M ago1:59

1:59

Text For Some Good Game LICENSE CODE FOR 'LOW LIT BLUES': KSU3MCDZNZBXW28K CORRECTION: I SAID "JUNE 9TH" BUT I MEANT JUNE 10TH This week on Let Me Pull Your Coat: The Unfiltered World of Master Silk, China Doll dives deep into the dark truth families don’t want exposed. Because sometimes, the most dangerous betrayal comes from the people sitting at…

1
Episode 378: How Wonderful Togbey Built a 20-Unit Portfolio Against the Odds 56:57

1M ago56:57

56:57

Properties for Sale on the North Side? We want to buy them. Email: [email protected] Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow…

1
From 304s to CEOs: How Silk Made Bosses 12:55

1M ago12:55

12:55

Text For Some Good Game While Master Silk handles business overseas, China Doll steps up to host this week’s episode with a special guest: Rochelle — a longtime friend, former dancer and escort, and now a powerhouse entrepreneur. These two women owe their glow-up to Silk's guidance, and now they're giving the game back. From street smarts to boardr…

1
(PREVIEW) From 304s to CEOs: How Silk Made Bosses 2:01

1M ago2:01

2:01

Text For Some Good Game Podcast Trailer for June 3, 2025 Support the show DON'T FORGET TO FOLLOW MASTER SILK ON ALL SOCIAL MEDIA PLATFORMS. https://letmepullyourcoat.com https://www.youtube.com/@mastersilk7630 https://www.instagram.com/chi_towns_og_mastersilk/ https://www.tiktok.com/@silktaylor https://x.com/abc105060 https://bsky.app/profile/maste…

1
Episode 377: This is How Grit Can Take You Further in Chicago Real Estate with Daniel Baker 55:27

2M ago55:27

55:27

Properties for Sale on the North Side? We want to buy them. Email: [email protected] Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow…

1
Pimps, Paper & Payback: China Doll Ain’t Holding Back: THE ONE YOU'VE BEEN ASKING FOR. 17:22

2M ago17:22

17:22

Text For Some Good Game License Code For Song: Low Lit Blues: NBOZNWQI6JYBOV9Y Pimps, Paper & Payback: China Doll Ain’t Holding Back: THE ONE YOU'VE BEEN ASKING FOR. This Week, the mic belongs to the woman who went from stilettos to stocks. From cashin’ out on corners to cashing checks off corporations—China Doll is telling it all. We’re pulling co…

1
Episode 376: Buy Before You Sell; How To Write Offers Non-Contingent on The Sale of Your Existing Property 10:20

2M ago10:20

10:20

Properties for Sale on the North Side? We want to buy them. Email: [email protected] Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow…

1
Episode 375: Learn How To Build A Chicago Portfolio Without Quitting the W2 with Nate Fernandez 52:05

2M ago52:05

52:05

Properties for Sale on the North Side? We want to buy them. Email: [email protected] Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow…

1
(PREVIEW) Pimps, Paper & Payback: China Doll Ain’t Holding Back: THE ONE YOU'VE BEEN ASKING FOR. 1:54

2M ago1:54

1:54

Text For Some Good Game This is a PREVIEW for Pimps, Paper & Payback: China Doll Ain’t Holding Back: THE ONE YOU'VE BEEN ASKING FOR. It drops Tuesday, May 27th. On that day, the mic belongs to the woman who went from stilettos to stocks. From cashin’ out on corners to cashing checks off corporations—China Doll is telling it all. We’re pulling coats…

1
She Hustled Healed & Cashed Out — The China Doll Come Up 17:09

2M ago17:09

17:09

Text For Some Good Game This week’s special episode brings double the wisdom. Master Silk is joined by former street hustler turned investor, Vanessa AKA China Doll, to break down real business questions from around the globe. Together they tackle: * Jealous family members and fake loyalty * Building while dating * Real estate hustle from the sneak…

1
Episode 374: Taking On Opportunity In Chicago’s Toughest Neighborhoods with Corey Oliver 1:06:33

2M ago1:06:33

1:06:33

Properties for Sale on the North Side? We want to buy them. Email: [email protected] Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow…

1
Real Hustle. No Hype. The Business Game They Don’t Teach You 20:01

2M ago20:01

20:01

Text For Some Good Game This week on Let Me Pull Your Coat: The Unfiltered World of Master Silk, we’re going all-in on business. From starting with nothing to building brands, dodging broke partners, scaling smart, and keeping your mental game sharp through it all. From flipping bad decisions into good investments to understanding when to walk away…

1
Episode 373: A New Option to Fund Renovations For Chicago 2-4 Properties 10:09

2M ago10:09

10:09

Properties for Sale on the North Side? We want to buy them. Email: [email protected] Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow…

1
Episode 372: Having Limited Capital and Scaling In Chicago Big Time with Kevin Schnell 54:20

2M ago54:20

54:20

Properties for Sale on the North Side? We want to buy them. Email: [email protected] Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow…

1
Loyalty Is Rare — Flexin' Is Cheap — Karma Is Expensive 20:46

2M ago20:46

20:46

Text For Some Good Game This week, Let Me Pull Your Coat: The Unfiltered World of Master Silk goes global and deeper than ever. We’re talkin’: Fake loyalty from people who only show up when you shine Flash over substance: the broke folks wearing $2,000 worth of rented lies Confused relationships, entitlement, and toxic attachments The real conseque…

1
Episode 371: How To Break into Chicago Real Estate Investing in Your 20s with Michael Kaplan 54:20

3M ago54:20

54:20

Michael Kaplan is a real estate broker and investor who has grinded to become a top broker at 24 years of age! Michael starts by explaining how he realized that college was not for him and pivoted to an entrepreneurial route in real estate! He explains the mindset required to start real estate investing and how he was able to acquire a 4-unit prope…

1
Pimps, Partners, and Pretenders: Lessons from Both Sides 25:00

3M ago25:00

25:00

Text For Some Good Game Pimps, Partners, and Pretenders: Lessons from Both Sides From the corners of Kingston to the clubs of Miami, this episode dives deep into the duality of street life and success. Master Silk tackles: Dating someone who used to sell their body How to confront a cheating business partner Kids throwing away second chances Gettin…

1
Episode 370: How The Current 2025 Lending Market Differs From Previous Year 12:00

3M ago12:00

12:00

What's Different in Today's Lending Environment and How do Chicago Investors Capitalize? ============= If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content! Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: [email protected] Guest: Eric Workman…

1
Episode 369: This Is How You Get Freedom of Time As a Chicago Investor with Erik Swanson 54:49

3M ago54:49

54:49

Erik Swanson, owner of Fernweh Property Group, explains how he’s developed a track record with investors that has allowed him to build a Tap Room business and an impressive real estate portfolio! Erik starts with very cool stories about his days in the music industry including working alongside some legendary bands! He dives into his first couple r…

1
From Street Hustle to CEO Muscle: Master Silk Breaks It Down 14:52

3M ago14:52

14:52

Text For Some Good Game From the gritty corners of the hustle to polished office suites, Master Silk’s seen it all and lived to talk about it — unfiltered, unapologetic, and real as hell. In this week’s deep dive, Silk peels back the velvet curtain on what it really takes to go from street game to CEO. In this weeks episode, questions come in from …

1
Episode 368: Current Chicago Apartment Sales & Leasing Trends with Joe Smazal & Ann Reilly (NSBC Live Event) 40:42

3M ago40:42

40:42

Tom and Mark interview Joe Smazal of Interra Realty and Ann Reilly of Westward360 during NSBC’s Live Event! Conversations range from leasing trends to handling evictions and the state of the multifamily market in 2025. This show is full of valuable insights from two heavy hitters in the Chicago Multifamily Real Estate market! If you enjoy today’s e…

1
From Love Drama to Street Hustles Master Silk’s Raw Truths 19:44

3M ago19:44

19:44

Text For Some Good Game In this episode of Let Me Pull Your Coat: The Unfiltered World of Master Silk, we're diving deep into life's toughest questions. From Tokyo to Texas, Cape Town to Cleveland we're pulling coats on everything, From love and loyalty to business and self-growth, Master Silk pulls no punches, offering raw, real-life advice that's…

1
Episode 367: How to Get Out In Front of Renewals With Jeff Weinberg 6:41

3M ago6:41

6:41

How do I incentivize and optimize renewals? ============= If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content! Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: [email protected] Guest: Jeff Weinberg, Drexel Properties Link: Jeff Weinberg Shar…

1
Episode 366: Networking Leader from Creative Financing to Six-Figure Commission Checks with Jeffrey Ma 54:43

3M ago54:43

54:43

Jeffrey Ma joins us to share his experience as a real investor, broker, and wholesaler including various creatively structured deals! Jeffrey starts by discussing his upbringing, start in real estate, and how he established a focus on wholesaling. He dives deep into “creative” deals including one deal where he was able to close on a property minute…

1
Global Game & Hard Truths Money, Love, and Loyalty 16:01

3M ago16:01

16:01

Text For Some Good Game This week, we’re taking Let Me Pull Your Coat, GLOBAL ! We got questions coming in from Belgium, France, Canada, South Africa, The UK, Australia and of course, right here in the States. From shady breakups to bad business deals, from cheating partners to money mishaps—you already know I’m pulling coats and telling it like it…

1
Episode 365: Building a $20 Million Portfolio Using BRRRR with Wyatt Simon 47:24

3M ago47:24

47:24

Wyatt Simon, owner of Full Circle Real Estate, discusses the successes and lessons learned in his journey to building a $20 million real estate portfolio! Wyatt starts by talking about how a successful BRRRR deal allowed him to gain momentum early on in his investing career. After a homerun deal, he shares lessons learned from a bad deal that invol…

1
Hustlers, Haters & Hard Truths—The Game Ain’t Free 12:17

4M ago12:17

12:17

Text For Some Good Game Welcome to Let Me Pull Your Coat: The Unfiltered World of Master Silk, where we talk real life, real money, and real consequences. Today, I’m pulling coats on everything from: Starting a business Investing like a boss Handling disrespectful kids who don’t respect their parents I’m even dropping some legal game Military Life …

1
Episode 364: Small Credit Items That Lead to Large Financial Impacts with Eric Workman 13:34

4M ago13:34

13:34

How does credit effect DSCR loans? ============= If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content! Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: [email protected] Guest: Eric Workman, Renovo Financial Link: Workman Lending Team - Renovo…

1
Episode 363: 168 Western Suburb units In Less Than 10 Years with John Warren 43:44

4M ago43:44

43:44

John discusses his start in real estate over a decade ago and reflects on missed opportunities, lessons learned, and success stories! He shares practical advice on simply structuring partnerships and talks about Forte Properties’ plan for growth in the western suburbs. John dives into starting a property management company along with building and r…

1
Bad Decisions & Broke Excuses 12:16

4M ago12:16

12:16

Text For Some Good Game This week, we talk about love, cheating, and why some of y’all are playing yourselves. This week we answer: Why do men get mad when women flip the script? Should you take a cheater back? Should you date a man for money? Why do nice guys finish last? Is dating your homeboy’s ex ever okay? Why are dudes crying over women with …

1
Episode 362: Free Money to Develop Affordable Housing? Learn How with Scott Henry 44:18

4M ago44:18

44:18

Scott Henry, Founder of Celadon Partners, joins to discuss the ins and outs of Affordable Housing Development including tax credits, grants, and construction considerations. Scott starts by sharing his experience working at JPMorgan’s Low Income Housing Tax Credit investment group and his transition to developing affordable housing! He provides a c…

1
Lifes Ups And Downs: We All Have Our Burdens 12:07

4M ago12:07

12:07

Text For Some Good Game In this episode, Master Silk breaks down: Why kids think they know more than their parents, How women flipped “he’s a trick” into “is he a good provider,” and The absurdity of women thinking a man owes them a five-star meal just because they washed their ass. Real talk on kids throwing away opportunities Parents struggling w…

1
Episode 361: What To Do Regarding the Northwest Side Preservation Ordinance 14:32

4M ago14:32

14:32

What actionable steps do I need to take for the Northwest Side Preservation Ordinance? ============= If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content! Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: [email protected] Guest: Brie Schmidt, …

1
Episode 360: Don’t Be Foolish, Protect Your Assets and This Is How with David Lanciotti and Del Denney 45:57

4M ago45:57

45:57

David Lanciotti and Del Denney of The Land Trust Company explain why all real estate investors should understand and consider utilizing Land Trusts! David and Del jump right in by explaining the basics and complexities associated with land trusts. They dive into the challenges that may arise when transferring properties into land trusts. The duo pr…

1
Love, Lies & The Hustle 10:20

4M ago10:20

10:20

Text For Some Good Game This week on Let Me Pull Your Coat: The Unfiltered World Of Master Silk, Master Silk keeps it all the way real: Is your girl cheating? Why do broke men have the best 'D' ? Are you in love with someone who doesn’t love you back? We're tackling all this and more with real, raw, and sometimes hilarious advice. Grab a drink and …

1
Episode 359: 2025 Cook County Evictions with Tom Raleigh 1:01:02

4M ago1:01:02

1:01:02

Tom Raleigh, Founding Attorney of Halsted Law Group, returns after being on Episode 40 to talk evictions! Tom jumps right in by breaking down the eviction process and the timelines in 2025. He gives great tips on getting ahead of the process and emphasizes the importance of staying on top of tenants and not waiting too long to file the eviction cas…

1
Used and Abused: Why They Take Advantage Of Your Love 9:27

4M ago9:27

9:27

Text For Some Good Game In this episode of Let Me Pull Your Coat: The Unfiltered World Of Master Silk, Master Silk breaks down one of the hardest truths in life—why the people you love the most are often the ones who use you the worst. Through personal stories of betrayal, heartbreak, and hard-earned wisdom, he exposes the narcissists, the entitled…

Podcasts Worth a Listen

Straight Up Chicago Investor Podcasts

Podcasts Worth a Listen

Quick Reference Guide