Best Straight Up Chicago Investor Podcasts (2025)

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

1d 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
Business News: Railroads Merge, Prebiotic Pepsi Pops Off, Real Estate Investors Surge, and Chicago's Sports Collectors Convention Heats Up 18:32

4h ago18:32

18:32

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
Innercise: John Assaraf is Helping Rewire Minds for Unstoppable Success 42:14

4d ago42:14

42:14

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

5d 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 29:35

8d ago29:35

29:35

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

9d 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

12d 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

10d 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 34:11

11d ago34:11

34:11

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
Business News: Stripe Bypasses IPO, Amazon’s Dark Pattern Debacle, MLB Tests AI Umpires, Microsoft’s Surprising Ad Surge 17:32

15d ago17:32

17:32

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

16d 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 40:24

18d ago40:24

40:24

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

22d 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

23d 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

25d 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

25d 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

29d 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

1M 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

1M 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

1M 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

1M 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

1M 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

1M 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

1M 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

1M 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

1M 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

1M 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

2M 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
From Trading Cards to Connections: The Heart of the Industry with Matty Rich 37:10

2M ago37:10

37:10

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 Recap: Trump & Musk Peace Treaty - Interest Rates Need to Drop - Apple No Longer Ripe - Agent Store is new App Store 16:54

2M ago16:54

16:54

In this episode of "Right About Now," host Ryan Alford recaps major business news of the week. He delves into the resolution of the Elon Musk–Donald Trump feud, advocates for lower interest rates to stimulate economic growth, and critiques Apple’s stagnation in innovation. Additionally, he examines the pervasive impact of social media on consumer b…

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

2M 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

2M 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

2M 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

2M 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
The Hobby is Big Business - Introducing Vee Friends w/ Gary Vaynerchuk 29:37

2M ago29:37

29:37

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: Marketers Bet Big on Podcasts, Veo 3 Demos Next‑Gen Video, TikTok Shop Changes the Game, Prime Day Sparks Shopping Sprees 34:57

2M ago34:57

34:57

In this episode of Weekly Business News, host Ryan Alford recaps the latest business news and trends. He celebrates the book launch of entrepreneurs Mike and Kass Lazerow, discusses the effectiveness of podcast advertising, and shares insights on Google’s new video AI, TikTok’s updated ad policies, Amazon Prime Day, and Starbucks’ revamped rewards …

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

2M 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

2M 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

2M 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
SHOVELING SH*T: The Entrepreneur's Messy Path to Success with Mike & Kass Lazerow 38:12

2M ago38:12

38:12

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

2M 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
The Real Truth About AI & Jobs - LeBron James Brand Extension - Mark Cuban Pushing Cheap Drugs - Crypto Gets Another Push to Mainstream 17:59

2M ago17:59

17:59

SUMMARY In today’s Weekly Business News, host Ryan Alford delves into key business topics. He discusses the impact of AI on white-collar jobs, urging professionals to embrace and leverage AI technologies. Ryan highlights LeBron James's new grooming line, "The Shop," as a savvy blend of lifestyle branding and media. He also covers the surge in Bitco…

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
Trading Cards: The Fan Engagement Goldmine with Jeremy Aisenberg 38:28

2M ago38:28

38:28

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
Real American Business News: Print isn't Dead, Just ask Microsoft - Cord Cutting Gets Sharper - YouTube is the new TV - Your Eyes Just Got Even More Valuable 22:31

2M ago22:31

22:31

SUMMARY In this episode of Right About Now, host Ryan Alford breaks down the latest business trends shaping the future. He explores Microsoft’s strategic pivot from print to digital media, the NBA’s groundbreaking streaming partnership with Amazon, and the implications of Sam Altman’s eye-scanning technology. Special guest and entrepreneur Gary Vay…

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

3M 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…

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Straight Up Chicago Investor Podcasts

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