Best Jay Winston Podcasts (2025)

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How to Start and Grow a 7-Figure Peach Stand Business | Shannon Houchin (MU Classic) 44:14

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1h ago44:14

44:14

#728 What if you could flip fruit into a seven-figure business? In this episode hosted by Brien Gearin, Shannon Houchin, founder of Roadside Republic, shares how she turned a humble $200 peach stand into a booming operation with dozens of stands and a powerful community impact. We dive into everything from sourcing farm-fresh peaches, negotiating w…

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How to Use AI and Other Tools to Hire Your Next Employee I Jessica Miller-Merrell (MU Classic) 56:15

1d ago56:15

56:15

#727 Are you overlooking the best places to find top talent? In this episode hosted by Kirsten Tyrrel, we’re joined by Jessica Miller-Merrell, a trailblazer in digital recruiting who’s been using social media and blogs to source candidates since the early 2000s. Jessica breaks down exactly how business owners can leverage their existing digital ass…

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Building a Calligraphy Brand: From Custom Work to Online Courses | Shinah Chang 51:34

1d ago51:34

51:34

#726 Former corporate lawyer turned creative entrepreneur, Shinah Chang shares the real (and refreshingly honest) journey of building a business that actually feels aligned. In this episode hosted by Kirsten Tyrrel, Shinah breaks down how she went from a risk-averse, straight-line “traditional success” path to bootstrapping a calligraphy brand — fi…

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Episode 312 - College Football Playoffs, Advent Part 4 - Joseph and Mary, and the Immaculate Reception 57:15

2d ago57:15

57:15

join the conversation as Matt and John talk college football, Joseph and Mary, and the Immaculate reception.By Matt Harmon and John Sloat

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Want More Conversions Without More Traffic? Here's How to Fix Your Website | Matthew Stafford 42:26

3d ago42:26

42:26

#725 What if the fastest way to grow your e-commerce revenue isn’t more traffic — but fixing what happens after customers land on your site? In this episode, host Kirsten Tyrrel sits down with Matthew Stafford, founder of Build Grow Scale, to unpack why most e-commerce businesses don’t actually have a traffic problem — they have a conversion proble…

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Posting on LinkedIn Might Be the Fastest Way to Build Your B2B Pipeline | Shamus Madan 40:04

4d ago40:04

40:04

#724 LinkedIn isn’t just a “nice to have” anymore — it might be the fastest way to build real B2B pipeline if you know how to play the game! In this episode, host Brien Gearin sits down with Shamus Madan, founder of Dealroom Media, to break down how his team helps founders go viral on LinkedIn and turn content into sales conversations. Shamus share…

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Gus Van Sant | Club Random with Bill Maher 1:37:55

4d ago1:37:55

1:37:55

Filmmaker Gus Van Sant joins Bill Maher for a candid conversation that pulls back the curtain on what it really takes to survive in Hollywood. Van Sant opens up about the scrappy, crowdfunded reality behind Dead Man’s Wire, studio politics, and why critics may have saved his career. The two dig into his iconic films (Drugstore Cowboy, My Own Privat…

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How to Stop Being the Bottleneck in Your Business and Break the 6-Figure Ceiling | Jason Moss (MU Classic) 51:09

5d ago51:09

51:09

#723 Are you grinding away in your business but still not seeing the income you want? In this powerful episode hosted by Kirsten Tyrrel, business coach Jason Moss breaks down why working harder isn’t the answer — and what to do instead. Jason shares how shifting your identity from operator to CEO can unlock real leverage, freedom, and income growth…

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Why Your Sales Page Isn’t Converting (And It’s Not Your Offer) | Martin Cris (MU Classic) 41:50

6d ago41:50

41:50

#722 If your sales page isn’t converting, it might not be your offer — it might be your presentation! In this episode hosted by Kirsten Tyrrel, web designer Martin Cris shares the formula behind high-converting landing pages, drawing on over 15 years of experience helping founders, creators, and course sellers increase their online revenue. Martin …

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How Web Hosting Can Be the Ultimate Recurring Revenue Business | Dylan Bost 47:14

7d ago47:14

47:14

#721 What if you could build a simple, high-demand business that prints predictable monthly revenue — while solving one of the biggest frustrations business owners have with their websites? In this episode, host Brien Gearin sits down with Dylan Bost, founder of Sunny HQ, to break down how to start a web hosting business built on recurring revenue.…

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Want to Build an App Around Your Passion? How Limon Is Changing Travel | Ramon and Lili Montes 48:30

8d ago48:30

48:30

#720 What if your next favorite travel recommendation came from a 60-second voice note instead of a blog post? In this episode, host Kirsten Tyrrel sits down with sibling co-founders Ramon and Lili Montes to unpack how they’re building Limon — a social, short-form audio app that captures the “photo album storytelling” experience for travel, with a …

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Nikki Glaser | Club Random Classics with Bill Maher 1:33:12

8d ago1:33:12

1:33:12

On this month’s Club Random Classics, Bill Maher sits down with comedian Nikki Glaser for a wide-ranging conversation about social media and self-image, Instagram perfection, how partners really see each other, the appeal of dating a celebrity, the value of couples therapy, and the art of a killer opening joke – plus why Nikki attended 18 Taylor Sw…

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Turn Your eComm Data into Pure Profit | Adam Callinan (MU Classic) 47:41

9d ago47:41

47:41

#719 If you've ever wondered how a SaaS business gets off the ground — or how math and spreadsheets can evolve into a powerful, profit-driving platform — this episode is for you! Host Brien Gearin sits down with Adam Callinan, founder of Pentane and host of the Growth Mavericks podcast, who shares his journey from building a multi-million dollar be…

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Episode 311 - TTUN Dumpster Fire, Advent Part 3 - The Magi and Herod, and Jameis Winston 54:14

9d ago54:14

54:14

Join the conversation as Matt and John talk about college football (Michigan's dumpster fire), the amgi and Herod, this day in sports history, and one thing they liked 0:00 Intro 4:40 Sports Roundup - college and pro football 23:48 Advent Part 3 - The Magi and Herod 42:03 This Day in Sports History 47:41 One Thing We Liked…

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How a Simplified Approach to Quilting Is Generating 7-Figures | Mike O'Dell 40:31

10d ago40:31

40:31

#718 Quilting might not sound like a “high-growth” business at first glance — until you meet Mike O'Dell, founder of Legit Kits, a company turning quilt patterns into ready-to-sew works of art! In this episode, host Kirsten Tyrrel sits down with Mike to unpack how he went from working as a certified registered nurse anesthetist to building a fast-s…

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Reclaim Your Time with AI: How Business Owners Are Freeing Up Hours Each Week | Corey Ganim 40:25

11d ago40:25

40:25

#717 Corey Ganim is back with a brand-new mission: helping small business owners reclaim their time through AI! In this episode hosted by Brien Gearin, Corey shares why he walked away from a wildly successful Amazon and e-commerce career to launch Return My Time — a company dedicated to identifying operational bottlenecks and prescribing simple, lo…

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Barry Levinson | Club Random with Bill Maher 1:36:56

11d ago1:36:56

1:36:56

Bill Maher sits down with Oscar-winning director Barry Levinson for a fast and funny masterclass in storytelling. Levinson revisits the Diner years and the “controlled chaos” of getting real performances – why loose, actor-driven rhythm can beat perfect dialogue, and how ensemble films changed the game. From there, it’s a hop through Hollywood hist…

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How to Build a 7-Figure Agency That Runs Without You | Jay Owen (MU Classic) 52:58

12d ago52:58

52:58

#716 What if your origin story isn’t what wins clients — but your ability to solve their problems is? In this episode hosted by Brien Gearin, Jay Owen, founder of Business Builders and host of Building a Business That Lasts, shares how he turned a teenage side hustle into a thriving multimillion-dollar agency that now runs mostly without him. Jay o…

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They Turned Their Voices into a 6-Figure Business — Here’s How | Dominick and Nicole Draper (MU Classic) 55:41

13d ago55:41

55:41

#715 What if your voice could become your most valuable asset? In this episode hosted by Kirsten Tyrrel, we sit down with Dominick and Nicole Draper — aka The Voiceover Couple — who turned a side hustle on Fiverr into a thriving voiceover business earning five-figure contracts. From recording commercials for major brands like Nike and Yahoo Sportsb…

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Entrepreneurs Who Scale Fast Do THIS with Masterminds | Cliff Ravenscraft (MU Classic) 1:06:45

14d ago1:06:45

1:06:45

#714 Ever wonder how some entrepreneurs skyrocket their growth while others stay stuck for years? In this episode hosted by Kirsten Tyrrel, we’re joined by Cliff Ravenscraft, a pioneer in the podcasting world who has helped over 40,000 people launch their shows and generated millions through online courses, coaching, and live events. Cliff shares h…

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The Non-Dual Heart of Christianity with Jory Pryor 1:03:22

13d ago1:03:22

1:03:22

In this episode, Winston is joined by Jory Pryor author of Becoming All Light: The Nondual Heart of Christianity and host of the Methods podcast. Together they explore the rich terrain of non-duality, Advaita Vedanta, and Christian mysticism, asking what it means to speak of God, self, and reality in a way that goes beyond the familiar dualities of…

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Want to Make Money as an Introvert? High-Income Side Hustles for "Anti-Influencers" | Megan Spencer 48:11

14d ago48:11

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#713 What if you could make multiple 5-figures from “introvert side hustles” without ever becoming an influencer? In this episode, host Kirsten Tyrrel sits down with Megan Spencer (“Meg the Creator”), a small-town, introverted mom who helps people build high-income side hustles through UGC, Amazon onsite commissions, TikTok Shop, and freelancing — …

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He Quit Drinking… Then Built a $10M Non-Alcoholic Beer Brand | Joe Chura (MU Classic) 47:26

15d ago47:26

47:26

#712 When Joe Chura quit drinking during the 75 Hard challenge, he didn’t just transform his health — he found his next business! In this episode hosted by Brien Gearin, Joe shares how that personal decision sparked the launch of Go Brewing, a non-alcoholic beer company built from his garage that’s now on track to hit $10 million in revenue. With a…

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How a Simple "Buy 1, Get 2 Free" Offer Turned into a $30M Eyewear Brand | Jonathan Strauss (MU Classic) 47:53

16d ago47:53

47:53

#711 What happens when you flip a jet ski, lose a $500 pair of sunglasses, and decide to build a better solution? You create one of the fastest-growing independent eyewear brands in the country! In this episode hosted by Brien Gearin, Jon Strauss, founder of Neven Eyewear, shares how that frustrating experience sparked a journey that led to a $30 m…

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Optimizing Google and Facebook Ad Performance in the AI Era | Ryan Burch 45:00

16d ago45:00

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#710 What happens when AI completely rewrites the rules of Google and Facebook ads — and most businesses don’t even realize it yet? In this episode, host Brien Gearin sits down with Ryan Burch, founder of the Tobie Group, to break down how Google and Facebook ads are changing in the age of AI. Ryan shares his journey from print advertising to runni…

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Episode 310 - OSU loses, Advent 2 - Shepherds, and Jay Berwanger 48:34

16d ago48:34

48:34

join the conversation as Matt and John talk about football, advent, and Jay Berwanger 0:00- intro 5:45-sports 20:38- advent 37:54-today in sports 42:07- one thingBy Matt Harmon and John Sloat

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He Turned Golf Gloves into a 6-Figure Business?! | Randall Pulfer (MU Classic) 56:03

17d ago56:03

56:03

#709 What if your next big business idea was hiding in plain sight — like on your golf glove? In this episode hosted by Brien Gearin, we sit down with Randall Pulfer, co-founder of Chipp Golf Co, a company reinventing the golf glove with bold designs and premium materials. Randall shares how he and his college friend went from brainstorming dorm ro…

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From Solo Painter to 6 Crews — How He Did It | Joshua Douglas (MU Classic) 52:44

17d ago52:44

52:44

#708 From solo painter to full-scale CEO, Josh Douglas has scaled A Painter’s Touch into a thriving multi-service business with six crews and multiple DBAs under one brand. In this episode hosted by Kirsten Tyrrel, Josh shares how he transitioned from doing all the work himself to building teams of subcontractors, expanding into services like floor…

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Love Satisfying, Repeatable Work? How Striping Parking Lots Yields Quick Cash Flow | Cinco Winston 45:37

18d ago45:37

45:37

#707 Want a business that turns fresh asphalt into a “blank canvas” — and pays well for satisfying, repeatable work? In this episode, host Kirsten Tyrrel talks with Cinco Winston, founder of Trueline Striping in Central Texas, about how he left a stable construction career, skipped the franchise route, and bootstrapped his own parking lot striping …

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Ana Kasparian | Club Random with Bill Maher 1:39:37

18d ago1:39:37

1:39:37

Ana Kasparian joins Bill Maher for a wild Club Random ride that swerves from Armenian moms with rolling pins and post-coital crossword puzzles to explosive debates on Israel-Gaza, trans rights, and California chaos. They spar thoughtfully on the AI job apocalypse and crime reforms gone wrong, Ana gets personal about her pandemic marriage, leaving t…

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He Was Broke… Until Laundry Made Him a Millionaire | Dave Menz (Part 2) (MU Classic) 46:33

19d ago46:33

46:33

#706 In part two of our masterclass with Dave Menz, the Laundromat Millionaire, we shift from customer experience to the operational engine that drives a truly scalable business. Dave reveals how documented systems, strong SOPs, and empowered employees are the foundation of long-term success — not just in laundromats, but in any service-based busin…

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He Was Broke… Until Laundry Made Him a Millionaire | Dave Menz (Part 1) (MU Classic) 49:09

20d ago49:09

49:09

#705 What if you could build wealth by revitalizing one of the most overlooked industries in America? In this episode hosted by Kirsten Tyrrel, we sit down with Dave Menz, the Laundromat Millionaire, who turned a failing, run-down laundromat into a multimillion-dollar empire by focusing on one key principle: serve your community better than anyone …

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How to Make YouTube Titles That Go Viral in 2025 l Jake Thomas (MU Classic) 53:19

21d ago53:19

53:19

#704 Have you ever wondered why some YouTube videos skyrocket while others flop? In this episode, host Kirsten Tyrrel is joined by Jake Thomas, expert YouTube title strategist and founder of Creator Hooks, to break down the psychology behind clickworthy titles and why the right 10 words could literally change your business. He explains the three co…

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Want to Scale Your Business via Franchising? How Diva Dance Grew to 50+ Locations | Jami Stigliano 51:26

21d ago51:26

51:26

#703 Thinking about turning your passion into a franchise or buying into a proven brand? In this episode, host Brien Gearin sits down with Jami Stigliano, founder of Diva Dance — a fun, confidence-building dance concept for adults with 50+ franchise locations across North America. Jami shares how a disappointing dance class in New York City led her…

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AI Is Reshaping the Creator Economy — Will Your Content Business Survive It? | Susie Bulloch 47:05

22d ago47:05

47:05

#702 What if the future of content creation depends less on algorithms and more on real human connection? In this episode, host Brien Gearin talks with Susie Bulloch — founder of Hey Grill, Hey — about how she grew a $35 WordPress site into a thriving barbecue brand with viral recipes, national retail products, and a deeply loyal community. Susie b…

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How Alex Neist Turned Mouth Tape into $40M in 2 Years | Alex Neist (MU Classic) 57:19

23d ago57:19

57:19

#701 What if better sleep could change your life — and build a booming business? In this episode, host Brien Gearin sits down with Alex Neist, former Arena League football quarterback and founder of Hostage Tape — the world’s largest mouth tape brand. Alex shares how poor sleep and snoring nearly derailed his health and marriage… until one life-cha…

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Psychology, Personality, Energy — Try These Unconventional Team Building Strategies | Larry Walshe 53:57

23d ago53:57

53:57

#700 What if the secret to building an unstoppable creative team has nothing to do with resumes — and everything to do with psychology, personality, and energy? Larry Walshe — founder of the globally renowned Larry Walshe Studios — joins host Brien Gearin to break down how he recruits and builds high-performance teams in the creative industry. Larr…

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Episode 309 - OSU beats TTUN, Advent 1 - Zechariah and Elizabeth, and Steve Scott 50:40

23d ago50:40

50:40

Join the conversation as Matt and John talk about OSU and the Jets winning, Advent, and Steve Scott. 0:00- intro 3:08-sports 20:45-advent 40:48- today in sports 45:58- one thingBy Matt Harmon and John Sloat

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Adapt Your Bookkeeping Business to Thrive in the Age of AI | Kate Johnson 35:25

24d ago35:25

35:25

#699 Bookkeeping might feel like an industry “at risk” in the age of AI — but according to returning guest Kate Johnson, it’s actually positioned for major growth! In this episode hosted by Kirsten Tyrrel, Kate shares how the accounting landscape is evolving, why AI-enabled bookkeepers will thrive, and how to ethically use new tools to speed up wor…

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He Buys Land Sight Unseen — And Profits Big | Seth Williams (MU Classic) 56:03

25d ago56:03

56:03

#698 What if your next big real estate win didn’t involve tenants, renovations, or even seeing the property in person? In this episode hosted by Kirsten Tyrrel, we’re joined by Seth Williams, founder of REtipster.com, who reveals how he built a thriving business flipping vacant land — often sight unseen. Seth shares the exact strategies he used to …

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Attract, Train, and Retain a High-Performing Team in Any Industry | Samantha Irwin 42:20

25d ago42:20

42:20

#697 Want to build a team that sticks with you, performs at a high level, and actually loves coming to work? Samantha Irwin — owner of Kaizen Coaching and Consulting and longtime friend of the show — returns for a deep dive into the art and science of employee retention! In this episode hosted by Brien Gearin, she shares her journey from middle-sch…

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John Malkovich | Club Random with Bill Maher 1:17:49

25d ago1:17:49

1:17:49

Bill Maher kicks back with John Malkovich for a candid conversation that jumps from Death of a Salesman and his new series Bad Monkey to his unexpected love of classical-music collaborations—and why so much theater ends up “a misery.” Malkovich opens up about his Leave-It-to-Beaver childhood, his 82nd Airborne environmentalist father, getting beate…

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The AI Hack That Helps You Buy a Business in 2025 | Nik Hulewsky (MU Classic) 48:19

26d ago48:19

48:19

#696 What if you could tap into an AI-powered business coach — one that’s available 24/7, never forgets a conversation, and helps you find, evaluate, and negotiate your next business acquisition? In this episode hosted by Brien Gearin, serial entrepreneur and podcast host Nik Hulewsky returns to the show to break down how he’s leveraging AI to find…

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She Outsourced Everything… and Still Made Bank Selling Sweatshirts on Etsy | Christina Umerez (MU Classic) 52:58

27d ago52:58

52:58

#695 What if your creative side hustle could fund your freedom and run itself while you explore the world? In this episode hosted by Kirsten Tyrrel, we’re joined by Christina Umerez, a digital nomad who built a successful Etsy print-on-demand business that now supports her travel-filled lifestyle. Christina shares how she went from custom pet portr…

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How to Kill It in the Restaurant Business | Ryan Gromfin (MU Classic) 53:40

28d ago53:40

53:40

#694 If you think a busy restaurant automatically means a profitable one — think again! In this episode hosted by Kirsten Tyrrel, we sit down with Ryan Gromfin, aka The Restaurant Boss, who pulls back the curtain on the flawed traditional restaurant business model. From his early days as a 15-year-old working in a five-star kitchen to building and …

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The Future of Church with Cathie Caimano 1:00:43

28d ago1:00:43

1:00:43

In this episode, Winston is joined by Rev. Cathie Caimano — Episcopal priest, writer, runner, and founder of Free Range Priest, Trexo: A Gym for Your Soul, and Substack Seminary, a new 12-month program helping clergy reclaim their ministry identity and build sustainable models of spiritual leadership. Winston and Cathie explore: her 25-year journey…

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How to Start a Gutter Installation, Repair, and Cleaning Business That Wows Customers | Aleks Krylov 43:26

28d ago43:26

43:26

#693 How did a Wall Street finance pro turn a simple gutter repair problem into New Jersey’s only white-glove gutter service? In this episode, host Brien Gearin sits down with Aleks Krylov, founder of Stern Gutters, to break down how to start a profitable gutter installation, repair, and cleaning business. Aleks shares his journey from Wall Street …

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Leverage Your Brain's "Operating System" to Ensure Success in Life and Business | John Assaraf 48:19

29d ago48:19

48:19

#692 Unlock the science behind your success with this fascinating deep-dive into how your brain drives every result you create! In this episode, host Kirsten Tyrrel sits down with behavioral neuroscience expert and bestselling author John Assaraf, who shares how understanding the brain’s “operating system” transformed his life from troubled teen to…

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Can One Guy Disrupt the Way We Learn? How Chad Fife, Founder of Revy School, Teaches Marketing, Sales, and Client Success Using Mentorship and Simulation | Chad Fife (MU Classic) 42:24

30d ago42:24

42:24

#691 What if you could launch a global education platform, inspire students across continents, and reinvent your career — all at once? In this episode hosted by Brien Gearin, we’re joined by Chad Fife, founder of Revy School, an online education platform that teaches marketing, sales, and client success through real-world simulations and mentorship…

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Launching a Customer-First Merch Company with No Industry Experience | Ethan Dowie 43:17

1M ago43:17

43:17

#690 Ready for a masterclass in grit, customer service, and unconventional scaling — all from a founder who built a booming merch company from scratch? In this episode, host Brien Gearin chats with Ethan Dowie, founder of Indigo Promotions, who went from making 400+ cold calls with zero traction to landing Zappos as one of his very first clients. E…