Best Straight Up Chicago Investor Podcasts (2025)

1
Episode 397: When Should You File an Insurance Claim and What Are the "Do's" and "Don'ts" When Filing an Insurance Claim on Your Property? 21:14

8h ago21:14

21:14

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
Earn While You Scroll: Inside Mode Mobile’s Business Model with Dan Novaes 31:43

9h ago31:43

31:43

Right About Now with Ryan Alford Join media personality and marketing expert Ryan Alford as he dives into dynamic conversations with top entrepreneurs, marketers, and influencers. "Right About Now" brings you actionable insights on business, marketing, and personal branding, helping you stay ahead in today's fast-paced digital world. Whether it's e…

1
Trailer: Behind the Velvet Rope: China & Master Silk Answer It All 1:41

3d ago1:41

1:41

Text For Some Good Game 🎙️This week, Master Silk and China Doll go all in—no question off limits. From sex positions, guilty pleasures, and wildest places to deep fears, family truths, and money moves—this episode strips it down raw. What you’ll hear: * China’s favorite sexual position & Silk’s balcony adventures * Our wildest places, foods, and fa…

1
Under The Oak: Neurodiversity's Impact on Creativity & Technology with Veronica Shelton 34:26

4d ago34:26

34:26

Right About Now with Ryan Alford Join media personality and marketing expert Ryan Alford as he dives into dynamic conversations with top entrepreneurs, marketers, and influencers. "Right About Now" brings you actionable insights on business, marketing, and personal branding, helping you stay ahead in today's fast-paced digital world. Whether it's e…

1
Episode 396: Buying, Building, and Adding Value in Self Storage with Fernando Angelucci 1:08:56

5d ago1:08:56

1:08:56

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
Why Generation Alpha and the Age of AI Will Change Everything with Matt Britton 35:11

7d ago35:11

35:11

Right About Now with Ryan Alford Join media personality and marketing expert Ryan Alford as he dives into dynamic conversations with top entrepreneurs, marketers, and influencers. "Right About Now" brings you actionable insights on business, marketing, and personal branding, helping you stay ahead in today's fast-paced digital world. Whether it's e…

1
Pain Don't Pause Purpose: Master Silk's Most Vulnerable Episode 6:31

7d ago6:31

6:31

Text For Some Good Game Life knocked me down hard this week. Family losses. Two sons in the hospital. Ten days that stretched into what felt like a lifetime of pain. I wasn't even planning to record today—was ready to step back, take a much-needed break, and just deal with the weight crushing down on me. Then something happened that changed everyth…

1
🎙️ Pain Don't Pause Purpose: Master Silk's Most Vulnerable Episode; Trailer 1:28

11d ago1:28

1:28

Text For Some Good Game I wasn’t even planning to drop a podcast this week… but real life had other plans. Loss, pain, and setbacks tried to knock me down—but the mic called me back. 🔥 Hit play on this trailer. Hear the truth. Feel the gratitude. 👉 Full episode drops August 26th, on Let Me Pull Your Coat: The Unfiltered World of Master Silk Life ha…

1
Micro Habits, Big Impact on BRAIN.ONE with Thoryn Stephens 35:41

11d ago35:41

35:41

Right About Now with Ryan Alford Join media personality and marketing expert Ryan Alford as he dives into dynamic conversations with top entrepreneurs, marketers, and influencers. "Right About Now" brings you actionable insights on business, marketing, and personal branding, helping you stay ahead in today's fast-paced digital world. Whether it's e…

1
Episode 395: Chicago Property Management and Leasing Best Practices with Max Motew 1:07:14

12d ago1:07:14

1:07:14

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 394: The Legal Nuances of Different Real Estate Partnership Structures 13:19

14d ago13:19

13:19

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 Filters to Failures: IG Hype vs. Real-Life Lessons 11:40

14d ago11:40

11:40

Text For Some Good Game Wise Man license Code: OQP95OFH4SOHMPIB Master Silk doesn't mince words as he exposes the dangerous fantasy world social media sells to young people. Drawing from decades of street wisdom, he systematically dismantles the illusion of "easy money" and "soft life" narratives that have trapped countless youth in cycles of explo…

1
Fields to Fortune: Moses Heredia’s Rise 35:50

14d ago35:50

35:50

Right About Now with Ryan Alford Join media personality and marketing expert Ryan Alford as he dives into dynamic conversations with top entrepreneurs, marketers, and influencers. "Right About Now" brings you actionable insights on business, marketing, and personal branding, helping you stay ahead in today's fast-paced digital world. Whether it's e…

1
Right About Now Evolves: New Formats, More Guests, and the Launch of Collectibles on SI 17:36

18d ago17:36

17:36

SUMMARY In this special episode, Ryan Alford announces major updates to the Right About Now podcast, including a shift to more frequent guest interviews and the launch of a new “Now in Ten” quick-interview format. He also unveils his upcoming show, Collectibles on SI, created with Sports Illustrated, which will explore the collectibles industry alo…

1
Episode 393: Chicago Veterans’ Guide to Real Estate Success with DuBois Toy 1:01:28

19d ago1:01:28

1:01:28

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
Business Power Moves: Navigating High-Stakes Entrepreneurship with Amrinder Kamboj 44:30

21d ago44:30

44:30

Right About Now with Ryan Alford Join media personality and marketing expert Ryan Alford as he dives into dynamic conversations with top entrepreneurs, marketers, and influencers. "Right About Now" brings you actionable insights on business, marketing, and personal branding, helping you stay ahead in today's fast-paced digital world. Whether it's e…

1
Daughters in Danger: Navigating Online Manipulation 15:59

21d ago15:59

15:59

Text For Some Good Game From Likes to Lies: When IG Fantasy Turns Daughters Against Their Parents This week on Let Me Pull Your Coat: The Unfiltered World of Master Silk, Silk and China Doll go deep into one of the most painful realities parents face today — daughters walking away from school, home, and family because of the glamorous lies they see…

1
BIG BADASSES IN BUSINESS 34:48

26d ago34:48

34:48

SUMMARY In this episode, host Ryan Alford brings together an all-star lineup of influential guests from diverse industries — including creative marketer Kyle Creek, legendary UFC announcer Bruce Buffer, Crumbl Cookies co-founder Sawyer Hemsley, former NFL star Shawne Merriman, and fitness entrepreneur Howard Panes. Each guest opens up with personal…

1
Episode 392: Cost Seg Kev Explains How Chicago Rehabbers Can Be Saving Tens Of Thousands Dollars 51:16

26d ago51:16

51:16

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 Reebok to Syntilay: Footwear Innovation with Joe Foster & Ben Weiss 36:00

28d ago36:00

36:00

Right About Now with Ryan Alford Join media personality and marketing expert Ryan Alford as he dives into dynamic conversations with top entrepreneurs, marketers, and influencers. "Right About Now" brings you actionable insights on business, marketing, and personal branding, helping you stay ahead in today's fast-paced digital world. Whether it's e…

1
Episode 391: Do You Have a Business Continuation Plan? 9:08

28d ago9:08

9:08

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
Sis… You Lied, Gaslit, Cheated, and Still Think You Deserve a King? 10:33

28d ago10:33

10:33

Text For Some Good Game This week, China Doll grabs the mic solo, so this week it's The China Doll Podcast. Silk requested that China pull the coats of delusional, entitled, gaslighting, and narcissistic women who keep leaving broken hearts—and broken trust—behind. With raw stories and personal heat, China answers men’s questions with unfiltered fi…

1
Business News: Railroads Merge, Prebiotic Pepsi Pops Off, Real Estate Investors Surge, and Chicago's Sports Collectors Convention Heats Up 19:02

1M ago19:02

19:02

SUMMARY Ryan Alford breaks down 8 major stories shaping business and marketing—from Shopify’s AI assistant and a historic railroad merger to PepsiCo’s prebiotic cola and Nike’s rapid sneaker lab. Plus: TikTok’s 60-minute videos, Sprite x Jalen Hurts, and more. TAKEAWAYS Shopify's introduction of the AI assistant Sidekick and its impact on e-commerc…

1
Episode 390: What Not To Do When Disaster Strikes: Mitch Schoeneman on Insurance Claims 58:58

1M ago58:58

58:58

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
Innercise: John Assaraf is Helping Rewire Minds for Unstoppable Success 42:44

1M ago42:44

42:44

Right About Now with Ryan Alford Join media personality and marketing expert Ryan Alford as he dives into dynamic conversations with top entrepreneurs, marketers, and influencers. "Right About Now" brings you actionable insights on business, marketing, and personal branding, helping you stay ahead in today's fast-paced digital world. Whether it's e…

1
No Filter, No Favors: We Said What We Said 10:42

1M ago10:42

10:42

Text For Some Good Game Master Silk and China Doll deliver raw, unfiltered advice on street betrayal, workplace manipulation, relationship deception, and establishing boundaries. We tackle real-life situations from Ghana to Australia, offering no-nonsense perspectives on family betrayal, corporate power plays, side piece dynamics, fake flexing, and…

1
Secrets to Influencer Marketing & Brand Engagement 30:05

1M ago30:05

30:05

In this Right About Now compilation, host Ryan Alford is joined by top voices in marketing and entrepreneurship—Gary Vee, Mike and Kass, Mark Kohler, Steve Pratt, Dani Lynn Robinson, and Ishveen Jolly—to break down what it really takes to stand out in today’s crowded content landscape. From the decline of traditional media to the rise of digital-fi…

1
Episode 389: Different Approach To Short Term Investing In Chicago With Sebastian Mysliwiec 1:02:15

1M ago1:02:15

1:02:15

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
Boundaries, Betrayal, and Building Better Circles 10:50

1M ago10:50

10:50

Text For Some Good Game Master Silk and China have returned with sharper minds, bigger accomplishments, and absolutely zero tolerance for users and fakers. While many podcasters apologize for breaks, we've been busy elevating - acquiring business stakes, flipping properties, organizing investment groups, and strategically reducing our circles to in…

1
Episode 388: NBOA 2025 Summer Soiree Update 14:38

1M ago14:38

14:38

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
Turning Followers into Brand Ambassadors with Luke Yarnton 34:41

1M ago34:41

34:41

Right About Now with Ryan Alford Join media personality and marketing expert Ryan Alford as he dives into dynamic conversations with top entrepreneurs, marketers, and influencers. "Right About Now" brings you actionable insights on business, marketing, and personal branding, helping you stay ahead in today's fast-paced digital world. Whether it's e…

1
Business News: Stripe Bypasses IPO, Amazon’s Dark Pattern Debacle, MLB Tests AI Umpires, Microsoft’s Surprising Ad Surge 18:02

2M ago18:02

18:02

SUMMARY In this episode of "Right About Now with Ryan Alford," Ryan breaks down seven major business stories shaping the week. Topics include MLB’s new automated umpire system, Microsoft’s surge in AI-driven ad revenue, Stripe’s $3B employee tender offer and IPO delay, Amazon’s FTC lawsuit over Prime’s “dark patterns,” TikTok Shop’s rapid trend shi…

1
Episode 387: This Is How You Make Money In Chicago In Your Early 20s with Alex Diaz 48:43

2M ago48:43

48:43

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
B-Sides: Flavor, Sustainability & Profit with Yousuf Ahmed 40:54

2M ago40:54

40:54

Right About Now with Ryan Alford Join media personality and marketing expert Ryan Alford as he dives into dynamic conversations with top entrepreneurs, marketers, and influencers. "Right About Now" brings you actionable insights on business, marketing, and personal branding, helping you stay ahead in today's fast-paced digital world. Whether it's e…

1
Business News: Tariff Tidal Wave - GPT-5 Changes the Game - Meta Recruits Top AI Talent - Prime Day Goes Bigger Than Ever - Frozen Fed Rates 11:15

2M ago11:15

11:15

On this episode of "Right About Now with Ryan Alford," Ryan covers five major business stories, including looming 25% tariffs on tech imports from China and South Korea, the anticipated launch of OpenAI’s GPT-5 and its impact on the AI industry, and insights from guest Matt Britton on AI-driven changes in hardware, creativity, and coding. The episo…

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

2M 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

2M 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
From Finance to Netflix "Million Dollar Secret" with Chris Allen 34:25

2M ago34:25

34:25

Right About Now with Ryan Alford Join media personality and marketing expert Ryan Alford as he dives into dynamic conversations with top entrepreneurs, marketers, and influencers. "Right About Now" brings you actionable insights on business, marketing, and personal branding, helping you stay ahead in today's fast-paced digital world. Whether it's e…

1
Stars, Stripes & Bottom Lines—No BS Business News From the Houseboat 10:40

2M ago10:40

10:40

Join Ryan Alford on this special 4th of July episode of “Right About Now”! He’s got you covered with all the latest business news and holiday cheer. From record-breaking travel to rising consumer spending, fireworks tariffs, and the S&P 500’s strong performance, Ryan’s got you covered. He’ll also share some fun pop culture moments and remind us to …

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

2M 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
Unlocking Passive Income: Secrets to Real Estate Success with Dani Lynn Robison 36:42

2M ago36:42

36:42

Right About Now with Ryan Alford Join media personality and marketing expert Ryan Alford as he dives into dynamic conversations with top entrepreneurs, marketers, and influencers. "Right About Now" brings you actionable insights on business, marketing, and personal branding, helping you stay ahead in today's fast-paced digital world. Whether it's e…

1
No BS Weekly Business News: Interest Rates, Mega Merger, Bezos Playing Monopoly, Elon Musk Touting Robo Taxi While Tesla Burns 13:58

2M ago13:58

13:58

Right About Now with Ryan Alford Join media personality and marketing expert Ryan Alford as he dives into dynamic conversations with top entrepreneurs, marketers, and influencers. "Right About Now" brings you actionable insights on business, marketing, and personal branding, helping you stay ahead in today's fast-paced digital world. Whether it's e…

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

2M 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

2M 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

2M 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
Creating his own Breaks - The Booming Hobby Series w/ Jason Koonce 39:08

2M ago39:08

39:08

Right About Now with Ryan Alford Join media personality and marketing expert Ryan Alford as he dives into dynamic conversations with top entrepreneurs, marketers, and influencers. "Right About Now" brings you actionable insights on business, marketing, and personal branding, helping you stay ahead in today's fast-paced digital world. Whether it's e…

1
Business News: Amazon’s Fuel-Cell Fleet, Fast-Food Price Wars, Sky-High Shipping, AI Guardrails, and Ikea Micro-Stores 19:02

2M ago19:02

19:02

SUMMARY In this episode of "Right About Now," host Ryan Alford recaps major business news of the week. Topics include Amazon’s shift to AI-driven job replacements and hydrogen fuel cell trucks, the return of dollar menus at fast food chains, Walmart’s rollout of drone delivery, new international AI safety regulations, expanding right-to-repair laws…

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

3M 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

3M 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

3M 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…

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Straight Up Chicago Investor Podcasts

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