Best Chris Jolly Podcasts (2025)

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Paul Rieckhoff: The Dangerous New Normal 49:01

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19m ago49:01

49:01

Charlie Sykes is joined by Iraq War veteran and Independent Americans host Paul Rieckhoff for a sobering conversation on the U.S. bombing campaign against Iran and the implications of Donald Trump’s unilateral decision to launch it. They unpack the erosion of guardrails around war powers, the growing risks of domestic instability, and the unnerving…

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The State of New York Baseball (with Jolly Olive and Will Warren) | 1244 38:52

1h ago38:52

38:52

Our Live Event at Fanatics Fest with Jolly Olive and Will Warren! Timestamps: 0:00 Yankees and Mets Mindsets 8:10 What Trade Can the Yankees & Mets Make? 13:27 Will Warren Joins the Show! 28:37 Best New York RosterBy Jomboy, Talkin' Jake, Jolly Olive, Will Warren

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1225. #TFCP - Entrepreneur in Overdrive: When Pivoting Becomes the Game Plan! 49:45

1h ago49:45

49:45

Today, our first guest for the week, Garrett Bowers of Bowers Trucking, explains the significance of face-to-face networking and its role in building relationships within the transportation industry! Garrett highlights how crucial it is to create a personal connection with potential clients, build systems for business development, prospect consiste…

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From Burnout to Buyout: How Chris Gist Built & Sold a Service Business in 3 years 27:30

44m ago27:30

27:30

Show Information Episode Number: 93 Date: July 23, 2025 Duration: 27:29 Host Contact Information Host: Justin Deese Website: JustinDeese.com Contact: [email protected] Guest Contact Information Guest: Chris Gist Company: Paradise Home Services Guest Website: www.ParadiseHomeServices.com Guest Email: [email protected] Summary …

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710 Weird and Wonderful Stories from Ancient Greece and Rome (with Paul Chrystal) | A BIG ANNOUNCEMENT | Two Listeners Follow Their Dream (And Create Something Amazing) 1:00:09

21h ago1:00:09

1:00:09

It's another action-packed episode! First, Jacke relays the story of a long-time listener who worked some mundane jobs before becoming an artistic bookmaker. Then Jacke talks to author Paul Chrystal about his work diving into lesser-known ancient texts for his book Miracula: Weird and Wonderful Stories of Ancient Greece and Rome. And in between, Ja…

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Clarke Schmidt Almost Throws No-Hitter & Jazz Saves the Yankees! | 1243 1:32:04

24h ago1:32:04

1:32:04

Use code YANKS2025 for 10% off your next SeatGeek order*: https://seatgeek.onelink.me/RrnK/YANKS2025. Sponsored by SeatGeek. *Restrictions apply. Max $20 discount Check out Olipop and buy any 2 cans of Olipop in store, and they’ll pay you back for one. Learn more at https://drinkolipop.com/YANKS Score your own grooming goals with American crew and …

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1224. #TFCP - Policy Overload: How Tariffs and Politics Are Reshaping Freight! 34:59

2d ago34:59

34:59

Dive into our last guest this week, Ed Burns from Burns Logistics, discussing the latest trends in freight and the impact of tariffs and politics on the industry! Ed shares the importance of operational resilience and effective cost management in the current market downturn, a platform to improve contract freight opportunities for shippers and carr…

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Yankees End the Losing Streak!!! (But Got Embarrassed by the Angels) | 1242 1:17:51

4d ago1:17:51

1:17:51

Follow all of our content on https://jomboymedia.com Use code YANKS2025 for 10% off your next SeatGeek order*: https://seatgeek.onelink.me/RrnK/YANKS2025. Sponsored by SeatGeek. *Restrictions apply. Max $20 discount Presented by Your Local Ford Stores. See highlights of the Ford Bronco® lineup: https://ford.com/bronco Use code JOMBOY15 at http://fa…

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1223. #TFCP - From Machine Vision to Margin Gains: The Business Case for Safer Fleets! 31:52

3d ago31:52

31:52

Today, Velocitor Solution’s Rudy Nemeth talks about the evolution of fleet technology from digitizing basic processes to integrated platforms that enhance safety and efficiency! Rudy highlights how utilizing AI in fleet management helps identify safety issues, existing data challenges in logistics companies, cash flow constraints faced by small bus…

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Olivia Troye: Fear as a Feature 58:09

4d ago58:09

58:09

Olivia Troye, former Homeland Security advisor to Mike Pence, joins Charlie Sykes to share her firsthand experience observing immigration court and the chilling tactics now being employed by ICE. They discuss the erosion of due process, the rise of politically motivated enforcement, and the broader consequences of fear-based governance under Donald…

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1222. #TFCP - The Real Sales Edge In Freight & What Shippers Look For! 30:56

4d ago30:56

30:56

In this episode, you’ll hear an analysis of what shippers look for when selecting freight providers, their sentiments and challenges, and how to build long-term relationships with them effectively. Tune in so you won’t miss another discussion that will help you stand out as a freight broker! 2025 Shipper Pulse Report: https://shorturl.at/Eixz9 📊📉 D…

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Poker Sheds and Above-Ground Pools: Unconventional Wins in STR Investing with Taylor Jolly 28:12

5d ago28:12

28:12

On this week’s episode, Avery is joined by Taylor Jolly, founder of Roam Free Vacation Home Rentals, to discuss how he transitioned from construction project management to profitable real estate investing. Taylor shares how he’s made co-living and large short-term rentals cash flow in expensive markets like Austin, leveraging creative strategies li…

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1221. #TFCP - From Hustle to Influence: Redefining Success in Freight Brokerage! 35:47

5d ago35:47

35:47

Today, we’re joined by incredible women in transportation, Lacey Olson and Amanda Haire - the co-founders of Transport Express! Despite coming from different industries, Lacey and Amanda share how they got into the freight business and continue to thrive, their challenges due to changing market conditions, and their focus on promoting a work-life b…

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Our Biggest Concerns for the Yankees (and Devers is Gone) | 1241 58:26

7d ago58:26

58:26

Use code YANKS2025 for 10% off your next SeatGeek order*: https://seatgeek.onelink.me/RrnK/YANKS2025. Sponsored by SeatGeek. *Restrictions apply. Max $20 discount Upgrade your skincare routine at https://CalderaLab.com/YANKS and use code YANKS at checkout for 15% off your first order. Shop SKIMS Mens at https://www.skims.com/yanks #skimspartner Dow…

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Ryan Lizza: Ten Years of Donald Trump 1:01:39

6d ago1:01:39

1:01:39

On the 10th anniversary of Trump’s infamous escalator ride, Charlie Sykes and Ryan Lizza reflect on a decade that has radically transformed American politics, media, and civic norms. From the reshaping of both political parties to the growing threat of political violence and institutional collapse, they explore how the Trump era has become the grav…

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1220. #TFCP - The Freight Forecast: Policy Pressure and a Cooling Market?! 31:31

6d ago31:31

31:31

Tune in and be updated today on the current transportation industry, with significant capacity and challenges in customer relationships, regional freight trends, insights on the impact of upcoming NMFC code changes, and the significance of continuous business development in a competitive market! References/Resources https://www.joc.com/article/us-t…

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92 | Beyond the Buzzwords: Real Talk on Tariffs, Recession, and Home Services with Jimmy Speyer 33:52

8d ago33:52

33:52

Show Information Episode Number: 92 Date: June 16, 2025 Duration: 33:25 Host Contact Information Host: Justin Deese Website: JustinDeese.com Contact: [email protected] Guest Contact Information Guest: Jimmy Speyer Company: Glass House Guest Website: GlassHouse.biz Summary In this episode, Justin Deese and Jimmy Speyer discuss the current econo…

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709 Black American Humor (with Damon Young) | The Greatest American Joke Ever Told? 1:31:52

8d ago1:31:52

1:31:52

DAMON YOUNG (⁠What Doesn't Kill You Makes You Blacker: A Memoir in Essays⁠) is a Pittsburgh writer and humorist. In this episode, Jacke talks to Damon about his work editing and writing an introduction for That's How They Get You: An Unruly Anthology of Black American Humor, which emphasizes how and why Black American humor is uniquely transfixing.…

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Yankees Swept in Boston. | 1240 1:15:28

9d ago1:15:28

1:15:28

Follow all of our content on https://jomboymedia.com Use code YANKS2025 for 10% off your next SeatGeek order*: https://seatgeek.onelink.me/RrnK/YANKS2025. Sponsored by SeatGeek. *Restrictions apply. Max $20 discount Check out Olipop and buy any 2 cans of Olipop in store, and they’ll pay you back for one. Learn more at https://drinkolipop.com/YANKS …

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Tom Nichols: Radicalization of the Armed Forces 34:39

9d ago34:39

34:39

Charlie Sykes welcomes Atlantic writer Tom Nichols for a fiery, wide-ranging conversation on a week that felt pulled from a dystopian novel. From a U.S. Senator being manhandled at a press conference to Trump’s military parade dreams and the radicalization of the armed forces, Nichols warns of authoritarian drift masked as political theater. They a…

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1219. #TFCP - The Ops Overhaul: Rewriting the Rules for Modern Teams! 33:53

10d ago33:53

33:53

Let’s end this week with more business growth strategies with today’s guest, John Marienau of Valey, sharing his real industry experience! John highlights the challenges and successes of entrepreneurship in freight, the importance of consistent daily effort and sustainable work practices, Valey’s comprehensive staffing solutions, and his goal to pr…

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Yankees SWEEP Royals AGAIN | 1239 1:16:38

11d ago1:16:38

1:16:38

Use code YANKS2025 for 10% off your next SeatGeek order*: https://seatgeek.onelink.me/RrnK/YANKS2025. Sponsored by SeatGeek. *Restrictions apply. Max $20 discount Presented by Your Local Ford Stores. See highlights of the Ford Bronco® lineup: https://ford.com/bronco Use code JOMBOY15 at http://fanaticsfest.com/tickets for 15% off tickets to Fanatic…

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1218. #TFCP - The Roadmap to Operational Excellence in Logistics! 31:28

11d ago31:28

31:28

If you’re looking for more strategies to operate and manage your freight business efficiently, look no further and listen to our guest, Kyle Lintner! Kyle emphasizes improving cash flow and profitability, key business assessment processes, the importance of automation, balancing technology and human interaction, and leveraging AI tools for various …

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Harry Litman: Trump, the Troops, and the Threat to Democracy 51:02

11d ago51:02

51:02

Charlie Sykes is joined by legal analyst and Talking Feds host Harry Litman for a sobering conversation about Donald Trump's latest maneuvers to militarize immigration enforcement—and what it signals for the future of American democracy. From the potential invocation of the Insurrection Act to the silence of military leadership, the two explore how…

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708 Science Fact and Science Fiction (with Keith Cooper) | AI Discovers a Work of Ancient Philosophy and Dreams Up a Reading List 1:11:01

12d ago1:11:01

1:11:01

For decades, writers and filmmakers have imagined worlds where characters can do things like watch a double sunset (on Tatooine, of course), or stand among the sand dunes of Arrakis, or gaze at the gas-giant planet Polyphemus from the moon Pandora. But even as works like Star Wars, Dune, and Avatar have enticed us with their fictional renditions of…

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1217. #TFCP - Surge or Illusion? What Tariffs Are Really Doing to Freight in 2025! 33:43

12d ago33:43

33:43

In this episode, we’ve got another incredible guest, Sean Dehan from Truckstop! Sean talks about the importance of adapting to challenging market dynamics, longer sales cycles post-COVID, Truckstop’s strategy for building long-term relationships and effective communication, future development plans, and more that you shouldn’t miss! About Sean Deha…

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Depreciation, Documentation, and Dodging Mistakes with Brandon Hall and Nathan Sosa 41:04

13d ago41:04

41:04

On this week’s episode, Avery is joined by Brandon Hall and Nathan Sosa of Hall CPA to dive deep into the short-term rental tax loophole and how investors can legitimately use it to offset W2 and business income. They discuss the origins of the loophole, how to qualify through material participation tests, and what documentation is necessary to sur…

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1216. #TFCP - How Can Brokers Prepare For The NMFC Code Changes!?! 30:05

12d ago30:05

30:05

Whether you’re an aspiring or experienced freight broker, listen to this episode with our returning guest from Rocket Shipping, Gabe Pankonin, as he shares his expert insights on upcoming NMFC code changes! Gabe explains how the NMFC changes could represent a significant shift in transportation, the opportunities for brokers to provide proactive an…

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Aaron Boone Explains How Giancarlo Stanton Will Fit in the Lineup | 1238 42:20

14d ago42:20

42:20

Use code YANKS2025 for 10% off your next SeatGeek order*: https://seatgeek.onelink.me/RrnK/YANKS2025. Sponsored by SeatGeek. *Restrictions apply. Max $20 discount Get the best 5G coverage in the game at https://t-mobile.com/Network Get your Jomboy Media All-Star Game Event Tickets at https://shop.jomboymedia.com This episode is sponsored by BetterH…

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Brian Klaas: Why Are There So Many Psychopaths in Politics? 46:27

13d ago46:27

46:27

Charlie Sykes is joined by political scientist and author Brian Klaas for a sobering look at how modern politics has come to attract the worst kinds of personalities—and why that’s no accident. They unpack the structural rot that fuels a rise in psychopathy, narcissism, and performative extremism among elected officials, and discuss the acceleratin…

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1215. #TFCP - The Freight CEO’s Journey: Discipline, Grit, and Long-Term Thinking! 32:38

14d ago32:38

32:38

Today, Bob King of Sage Freight brings his over thirty years of experience in the transportation industry and the entrepreneurial mindset that keeps him thriving and growing! Bob emphasizes prioritizing revenue-generating activities, accepting personal liability impacts decision-making, and promoting long-term customer relationships. Tune in to unp…

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91 | Leading with Purpose: Discover Your Leadership Style with Justin Deese 20:16

15d ago20:16

20:16

Show Information Episode Number: 91 Date: June 9, 2025 Duration: 20:15 Host Contact Information Host: Justin Deese Website: JustinDeese.com Contact: [email protected] Summary In this episode of the Freedom Blueprint podcast, Justin Deese discusses the complexities of leadership, emphasizing the importance of understanding different leadership …

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Red Sox Beat Us. | 1237 1:26:50

15d ago1:26:50

1:26:50

Follow all of our content on https://jomboymedia.com Use code YANKS2025 for 10% off your next SeatGeek order*: https://seatgeek.onelink.me/RrnK/YANKS2025. Sponsored by SeatGeek. *Restrictions apply. Max $20 discount Control Body Odor ANYWHERE with @shop.mando and get 20% off + free shipping with promo code YANKS at shopmando.com! #mandopod Shop SKI…

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707 Emile Zola (with Robert Lethbridge) | Graham Greene's Only Ghost Story | My Last Book with Irina Mashinski 1:00:42

15d ago1:00:42

1:00:42

For years, listeners have been requesting an episode devoted to the French novelist, journalist, playwright, and public intellectual Émile Zola (1840-1902). In this episode, Jacke talks to author Robert Lethbridge, whose new book Émile Zola: A Determined Life presents a comprehensive exploration of the life, work, and times of the celebrated French…

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Sen. Angus King: The Fragility of American Democracy 28:17

15d ago28:17

28:17

Senator Angus King joins Charlie Sykes for a sobering conversation on the erosion of constitutional norms, the rise of authoritarianism, and Congress’s failure to defend its own power. Drawing lessons from history—including Margaret Chase Smith’s defiance of McCarthyism—King warns that America’s democratic experiment is more vulnerable than most re…

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1214. #TFCP - Cold Chain Command: Inside the World of Perishable Freight! 33:39

17d ago33:39

33:39

Want to learn more about refrigerated freight for the food and beverage industry? Listen to this week’s last guest, Michael Cherney, the co-founder and CEO of Cooler Logistics! Michael shares his shift from the financial services sector to founding Cooler Logistics, their company’s strategic focus on small to mid-sized customers, innovative operati…

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Talkin' Yankees vs. Red Sox & More with Katie Nolan | 1236 43:32

18d ago43:32

43:32

Follow all of our content on https://jomboymedia.com Use code YANKS2025 for 10% off your next SeatGeek order*: https://seatgeek.onelink.me/RrnK/YANKS2025. Sponsored by SeatGeek. *Restrictions apply. Max $20 discount Use code JOMBOY15 at http://fanaticsfest.com/tickets for 15% off tickets to Fanatics Fest from June 20th - 22nd!…

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Jazz Comes Back & Yankees Win ANOTHER Series vs. Guardians | 1235 1:28:41

18d ago1:28:41

1:28:41

Follow all of our content on https://jomboymedia.com Use code YANKS2025 for 10% off your next SeatGeek order*: https://seatgeek.onelink.me/RrnK/YANKS2025. Sponsored by SeatGeek. *Restrictions apply. Max $20 discount Presented by Your Local Ford Stores. See highlights of the Ford Bronco® lineup: https://ford.com/bronco Use code JOMBOY15 at http://fa…

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1213. #TFCP - Why the Freight Market Recovery Could Still Be a Long Way Off! 29:23

18d ago29:23

29:23

Today, you’ll hear more market trends within the trucking industry, sales prospecting strategies, implementing better financial planning, and leveraging AI for operational efficiency! Tune in so you won’t miss an episode that is valuable for your freight business! 📊📉 Don’t miss out on the latest market trends by subscribing to your TOP Transportati…

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Adam Kinzinger: The Billionaire Breakup 41:17

18d ago41:17

41:17

Charlie Sykes and Adam Kinzinger dig into the political fallout from Elon Musk's dramatic split with Donald Trump, examining what it means for MAGA loyalty, conservative orthodoxy, and the future of Republican messaging. They explore how the culture war has overtaken fiscal policy, the strategic shifts in the war in Ukraine, and the geopolitical im…

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1212. #TFCP - Scan, Weigh, Save: The ROI of Automated Dimensioning! 33:02

19d ago33:02

33:02

Listen to our featured guest today, Scooter Sayers of Cubiscan, sharing their role in the logistics industry, their four decades of journey, and Cubiscan’s advanced automated dimensioning systems! Scooter delves into the upcoming National Motor Freight Classification (NMFC) changes, the importance of shippers understanding these changes to minimize…

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Why Every Short-Term Rental Investor Needs a Tax Strategy with Yonah Weiss 35:25

19d ago35:25

35:25

On this week's episode, Avery is joined by Yonah Weiss, an expert on cost segregation and a favorite among real estate investors. They break down what a cost segregation study is, how it allows short-term rental owners to accelerate depreciation and save on taxes, and who qualifies to benefit from this strategy. Yonah explains how to navigate bonus…

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1211. #TFCP - Beyond the Résumé: Identifying Talent in Logistics! 32:32

20d ago32:32

32:32

In this episode, we’ve invited a talent acquisition expert from Global Executive Solutions Group, Josiah DiPaolo, to discuss the intricacies of recruiting effective people within the transportation industry! Tune in to hear his insights on the job market, the demand for specific freight expertise, particularly in sales roles, and his advice for fre…

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Aaron Boone Explains the Luke Weaver Injury | 1234 49:31

21d ago49:31

49:31

Use code YANKS2025 for 10% off your next SeatGeek order*: https://seatgeek.onelink.me/RrnK/YANKS2025. Sponsored by SeatGeek. *Restrictions apply. Max $20 discount Get the best 5G coverage in the game at https://t-mobile.com/Network Score your own grooming goals with American crew and grab these products at https://tinyurl.com/yrckykrd. Style like a…

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Justin Wolfers: Tacos, Tariffs, and the Taquito Economy 46:10

20d ago46:10

46:10

Economist Justin Wolfers joins Charlie Sykes to unpack the economic whiplash of Donald Trump’s on-again, off-again trade wars, explaining why the president's tariff policies are more than just political theater—they’re rewriting the rules of international trade. In a lively, metaphor-rich conversation, they explore the constitutional implications o…

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1210. #TFCP - Keeping It Real: Transparency and Trust in Family-Run Freight! 33:13

21d ago33:13

33:13

What’s the key to maintaining a core competency in freight and succeeding for a multi-generational family-owned trucking business? Today, we’ve got an incredible guest, Pamela Polyak of Polyak Trucking, and hear her real-world experience, business strategies, and commitment to industry improvement! Some Takeaways From This Episode: Strategic Compan…

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90 | Live from the Power Profit Workshop: Rebranding Success: The Story of Jolly Goat Garage Doors 13:31

22d ago13:31

13:31

Show Information Episode Number: 90 Date: June 2, 2025 Duration: 13:31 Host Contact Information Host: Justin Deese Website: JustinDeese.com Contact: [email protected] Guest Contact Information Guest: Jeff Gabelsberg Company: Jolly Goat Garage Doors Guest Website: https://jollygoatgaragedoors.com/ Summary In this episode of the Freedom Blueprin…

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Two Awful Losses, One Good Win for Yankees vs. LA Dodgers | 1233 1:18:43

22d ago1:18:43

1:18:43

Follow all of our content on https://jomboymedia.com Use code YANKS2025 for 10% off your next SeatGeek order*: https://seatgeek.onelink.me/RrnK/YANKS2025. Sponsored by SeatGeek. *Restrictions apply. Max $20 discount Go to https://storyworth.com/YANKS to save $15 on your order! Go to kushydreams.com and use Promo Code JOMBOY at checkout to get 20% o…

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706 Living with Jane Austen (with Janet Todd) | A Listener Changes His Life | Bored Parents 1:12:23

22d ago1:12:23

1:12:23

It is a truth universally acknowledged, that Jane Austen's novels make us wish she was our friend. She wouldn't be just any old friend: she'd be the sharpest and wisest, the one we turn to in a crisis, the one who understands our flaws and helps us see our blind spots. As we navigate the perils of love and life, she'd be the friend who gently point…

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Julian Zelizer: The End of the Bromance 44:34

23d ago44:34

44:34

Historian Julian Zelizer joins Charlie Sykes to discuss Donald Trump’s growing hostility toward former allies—from the Federalist Society to Elon Musk—and what it signals about a second Trump term. They explore the erosion of institutional guardrails, the chilling effects on higher education, and the constitutional dangers of unchecked presidential…