This is Tailwind Marketing podcast, where we talk to other B2B marketing leaders and agency executives about how to grow our businesses profitably.
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Tailwind Talks is a podcast for high-performing professionals who want to build serious real estate portfolios without leaving their careers. Hosted by an airline and military pilot turned investor, it dives into actionable strategies for scaling your real estate portfolio while balancing the demands of a full-time job.
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A collection of short form audio updates weekly (The Tailwind Digital Minute) and longer episodic podcasts (The Tailwind Twenty) from the minds at Tailwind in Tempe, AZ. Get the latest updates in digital marketing trends, technologies and more.
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Welcome to an aviation podcast that caters to all aviation enthusiasts, ranging from pilots to airplane spotters. Our show covers a wide range of topics, including private pilot training, airline operations, and the latest aviation news. Our knowledgeable host, an experienced airline pilot with eight years of flying under his belt, is thrilled to share his own experiences and offer valuable advice to help you pursue your aviation dreams. We are here to support you on your journey, constantly ...
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Turning Events Into Real Revenue
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38:07COVID crushed events. Then AI, automation, and inbox spam made everyone forget how to talk to people. In this episode, Jocelyn Sexton and Carlos break down what’s actually working with events, and why the ROI isn’t in the booth. From “just go to the bar” tactics to how to avoid webinar fatigue, they show how to make people care, follow up like a hu…
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If Clicks Closed Deals, We’d All be Rich
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39:10The buyer’s journey has changed and so should your marketing. In this episode, Jeff Bradburry and Carlos Corredor talk through how the shift to digital has changed what marketing needs to focus on. It’s no longer about pushing content or chasing clicks, but about creating qualified opportunities that lead to real pipeline. They challenge the idea o…
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Person-to-person beats Company-to-persona
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40:40There’s something about B2B that makes marketers want to sound like robots. Brian Krenzer’s not here for it. In this episode, he and Carlos break down what B2B marketers can steal from consumer brands—and what they still get wrong. From defining your ICP to fixing the planning phase, Brian’s take is practical, punchy, and grounded in math. Not vibe…
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Growth by Acquisition. Scale by Marketing
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27:16Marketing isn’t about cranking out perfect, timeless content anymore—it’s about moving fast when nothing sits still. In this episode, Kate Bitely joins Carlos to talk about the messy reality of marketing through hyper-growth, mergers, and running lean. Forget “evergreen.” Think AI as your extra teammate, there for speed and sparks. And here’s the t…
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The Ultimate Top Funnel Play: Community Building
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41:22What if everything you’re doing to “build” a community is driving it away? Jason Baum’s journey into community-building started in unexpected places—before it became a B2B buzzword. In this episode, he and Carlos unpack what most brands get wrong about building a community: it’s not a channel, it’s not a forum, and it’s definitely not a short-term …
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Why I Just Bought 3 Duplexes — Even at 6.75% Rates | Real Estate Market Is Shifting
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15:05Send us a text Ever wondered when the real estate market would finally shift in favor of buyers? That moment has arrived, and I'm seizing the opportunities. Despite mortgage rates hovering around 6.75%, I've purchased more properties in recent months than I had in years. This past week alone, I closed on three duplexes (six units total) - including…
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Send us a text Your monthly rent check is powering a sophisticated wealth-building engine for your landlord that goes far beyond simple cash flow. Speaking from the unique perspective of both a rental property owner and someone paying $2,000 monthly rent, this breakdown reveals the complete financial picture that most tenants never see. While cash …
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How I’m Buying over $1,000,000 in Rentals with No Cash Down
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17:08Send us a text How do you keep growing your real estate portfolio when interest rates make traditional cash-out refinancing impractical? The answer might lie in creative loan structuring and relationship banking. Cole, balancing careers as both an airline pilot and real estate investor, walks us through his innovative approach to expanding his port…
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June Rental Portfolio Breakdown – The REAL Income & Expenses from 60 Units
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18:42Send us a text Ever wondered what real estate investing actually looks like behind the gloss of social media success stories? Drawing back the curtain on my 60-unit rental portfolio, I'm sharing every dollar that came in and went out during the month of June—something I wish someone had done for me when I was starting out. The numbers tell a story …
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This Deal Looks Good But Will Bankrupt You | Real Estate Rookie Mistakes
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13:19Send us a text Navigating the world of real estate investing can be treacherous for beginners, especially when sellers disguise money-losing properties as profitable opportunities. In this analytical breakdown, Cole—a part-time real estate investor, airline pilot, and military instructor—dissects a misleading 14-unit Milwaukee apartment listing tha…
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I Funded This $60K Rental Property in Just 31 Minutes
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11:11Send us a text Ever wonder how some investors seem to close deals overnight while others struggle for months? The secret isn't luck or connections—it's preparation and relationships. I recently transformed an ordinary text message into a fully-funded real estate deal in just 35 minutes. This wasn't through some complex strategy or inside connection…
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How I’m Managing $5.9M in Real Estate
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17:38Send us a text Unlocking the hidden power of real estate equity could be the key to exponential portfolio growth—yet so many investors leave millions in potential wealth sitting idle. As a part-time real estate investor juggling careers as both an airline pilot and military instructor, I've built a portfolio valued at nearly $5.9 million with appro…
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Inside My 60-Unit Real Estate Portfolio: What I Actually Make Each Month
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11:54Send us a text A rare glimpse behind the curtain of real estate investing reveals what actually works—and it's probably not what you've been told. Cole, a part-time real estate investor balancing a full-time airline career and military instructor role, shares the unvarnished truth about his 60-unit portfolio generating $55,000 monthly in gross inco…
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Send us a text The real estate investing world is full of so-called "rules" that promise success, but few are as potentially destructive as the popular 1% rule. As someone who balances being a legacy airline pilot, military instructor, and property investor, I've seen firsthand how this oversimplified formula leads well-meaning investors straight t…
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Send us a text Imagine going from the cockpit of a commercial jet to facing unemployment overnight. That's exactly what happened when COVID-19 devastated the aviation industry and left me questioning everything I'd built. This raw, honest conversation explores the harsh reality of career vulnerability and the steps I took to rebuild financial secur…
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Send us a text Challenging conventional wisdom can be difficult, but sometimes the numbers tell a story that can't be ignored. As a successful real estate investor managing a multi-million-dollar portfolio, I've made the counterintuitive choice to rent my personal residence rather than own it—and today, I'm sharing the eye-opening math behind this …
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Send us a text Ever wonder how ordinary people create extraordinary wealth through real estate? The answer might be simpler than you think. Imagine purchasing a multi-unit property, living there at a fraction of market rent, and walking away with a six-figure profit – all without spending a dime from your savings. This isn't some get-rich-quick sch…
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Can You Really Buy Real Estate With No Money? The Truth About Hard Money
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15:46Send us a text Diving deep into the world of high-leverage real estate investing, this candid exploration of hard money lending reveals both its immense potential and serious pitfalls. Drawing from personal experience—including costly mistakes—I break down exactly how these loans work and when they make sense for investors at different stages. Hard…
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It Starts With a Prompt. It Ends With a Point of View: How to Create Great Copy
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32:46The robots can write. That’s not the problem. The problem is they can’t sound like you. And if your content doesn’t sound like you, it might as well be invisible. This episode covers copywriting in the AI era—where prompts meet point of view, sales teams drop blog ideas into Slack, and marketers try to rank on Google without losing their soul. Carl…
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Why I Haven’t Quit My Job (Even with 60 Rental Units)
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13:37Send us a text Ever wondered why someone with 60 rental units would keep their day job? I'm breaking down exactly why I've chosen to maintain my career as a legacy airline pilot and military instructor while building my real estate portfolio. The foundation of successful real estate investing isn't about quitting your job—it's about leveraging it. …
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6 Things I Look For Before Buying Rental Property
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13:28Send us a text Wondering how successful real estate investors evaluate potential rental properties? In this transparent, no-nonsense breakdown, Cole—a part-time real estate investor balancing a career as both a commercial airline pilot and military instructor pilot—reveals his six-point property evaluation system built from years of hands-on experi…
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The #1 Real Estate Investing Tip I Wish I Knew Earlier | Why Partnerships Are a Superpower
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14:41Send us a text Ever wondered why some real estate investors seem to scale their portfolios so quickly while others struggle for years to add a second property? The secret might be simpler than you think—strategic partnerships. Drawing from my experience as a part-time real estate investor juggling careers as both a legacy airline pilot and military…
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Closed on a Duplex & Single-Family with Hard Money | My Path to 100 Units
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12:07Send us a text Stepping closer to my goal of owning 100 rental units, today marks another milestone as I close on two new properties—bringing my portfolio to 60 units after some recent sales and acquisitions. These seemingly ordinary properties reveal extraordinary lessons about creative real estate financing and spotting long-term value in today's…
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The Housing Market is Broken – And It's Still Going Up
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13:45Send us a text Ever wonder why housing prices keep climbing despite 7% interest rates and affordability at a 40-year low? You're not alone. The housing market continues to confound conventional wisdom, with properties selling well above asking price even as monthly mortgage payments have skyrocketed 90% since 2020. The mystery deepens when you cons…
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Why Quitting Too Early Will Kill Your Real Estate Dreams
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11:50Send us a text The dream of quitting your 9-to-5 to pursue real estate full-time tempts many new investors. But is rushing to leave your job actually sabotaging your long-term success? Drawing from a decade of experience balancing property investing with careers as both an airline pilot and military instructor, this candid discussion reveals why yo…
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Send us a text Ever feel like you've done everything right in your career but still can't afford the home you want? You're not alone. As a commercial airline pilot, military instructor, and real estate investor, even I'm feeling the squeeze of today's housing market—so much that I'm currently renting an apartment while owning multiple rental proper…
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Send us a text Forget everything you thought you knew about real estate licenses - they're not just for salespeople. My journey getting licensed eight years ago wasn't driven by a desire to chase commissions or become the next real estate mogul. It was a strategic move to understand the rental property business from the inside out, granting me acce…
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Send us a text The path to real estate wealth rarely looks like the glamorous stories we see online. Sometimes, it means making the uncomfortable choice to live with your parents well into adulthood or finding roommates to slash your biggest expense. That's exactly what I did – working as an airline pilot, flying military missions part-time, and gr…
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Send us a text Challenging conventional wisdom, I take you through my controversial but pragmatic approach to real estate. Despite owning millions in rental properties, I've made the strategic choice to rent my own home—and there's solid financial logic behind this decision. The current real estate market presents a perfect storm of challenges: sky…
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Send us a text The unexpected call every property investor dreads finally came my way—a complete fire loss at one of my rental properties. Standing in the charred remains, the acrid smell of smoke overwhelming my senses, I faced the sobering reality that despite owning multiple properties, I had absolutely no experience navigating insurance claims.…
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Send us a text Ready for some hard truth about real estate investing? You don't need to spend $4,000 on a guru's course to learn how to buy rental properties. This episode cuts through the hype and exposes the predatory practices of high-priced real estate "education" programs that target hopeful investors with limited resources. We break down a tr…
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Send us a text Ever wonder if you can build a real estate portfolio while working a demanding full-time job? Cole proves it's not just possible—it's happening right now. Fresh off his morning flight as an airline pilot, Cole closed not one but two profitable Milwaukee properties by afternoon, showcasing the power of preparation and strong industry …
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Send us a text When a seemingly solid brick duplex turned into a financial disaster, I learned an expensive lesson about the hidden costs lurking beneath investment properties. This candid breakdown reveals how my worst property of 2024 generated $17,803 in annual income while racking up a staggering $50,425 in expenses – creating a negative cash f…
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Send us a text Turning $50,000 into a 27% annual return might sound like an investment fantasy, but that's exactly what happened with my best-performing property of 2024. Join me, Cole – airline pilot, military instructor, and part-time real estate investor – as I pull back the curtain on a four-unit brick building that's defying expectations and g…
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Send us a text Mortality is the great equalizer—and realizing this simple truth can transform how we approach life's challenges and opportunities. Have you ever found yourself paralyzed by fear when considering a new venture? Whether it's investing in real estate, applying to flight school, or starting a YouTube channel, many of us get trapped in e…
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Start Real Estate in 2025 with Just $5K (and what I wish I would have done) Tailwind Talks 002
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27:13Send us a text Breaking into real estate investing can feel impossible when you're starting with minimal capital. The barrier to entry seems insurmountable with rising property values, high interest rates, and fierce competition. But what if you could launch your real estate journey with just $5,000? This raw, practical guide cuts through the noise…
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Send us a text Ever wondered what separates successful real estate investors from those constantly feeding money into their properties? The answer might be simpler than you think. Cash on cash return stands as the ultimate metric for measuring real estate investment success. It cuts through the noise of speculative appreciation and trendy market pr…
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Send us a text Ever feel like you're drowning in spreadsheets and second-guessing your real estate investment decisions? What if analyzing a property could be as simple as glancing at your watch? Today, I'm pulling back the curtain on my actual process for evaluating potential investment properties in under five minutes. As a full-time pilot and pa…
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Building a $5.5 Million Portfolio While Working Full-Time as a Pilot (Tailwind Talks 001)
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12:04Send us a text Ever wonder how to build substantial real estate wealth while keeping your day job? Meet Cole, a full-time airline pilot, part-time military helicopter pilot, and real estate investor who's built a $5.5 million portfolio spanning 63 units—all without quitting his aviation career. Cole's journey began humbly washing dishes as a teenag…
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Why Likable is Better Than Clever
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47:02In this episode of the Tailwind Marketing Podcast, Carlos Corredor speaks with Brett Carnali, VP of Sales and Marketing at Stone Door Group, about what most sales and marketing people miss: empathy. They dig into why detaching from the outcome leads to better deals, how overthinking your funnel kills momentum, and why simple, honest messaging beats…
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A “Numbers First” Engineering Approach to Marketing Growth
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31:44In this episode of the Tailwind Marketing Podcast, Carlos Corredor speaks with Charudhi Pankaj, Head of Growth at Top Flight, about applying engineering thinking to marketing—starting with numbers and auditing before planning. They break down common mistakes like building personas around what you can sell instead of what customers actually need. Th…
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If Your Brand Went on a Date with Your Audience… Would There Be a Second One?
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44:55In this episode of the Tailwind Marketing Podcast, Carlos Corredor talks with Brittany Dufin about understanding your customer to create marketing that hits the mark. Brittany shares how aligning marketing with project managers and sales teams—who talk directly to customers—helps produce more relevant content. While too much feedback can be overwhe…
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Running a Lean Marketing Team That Grows With Your Business
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38:47In this episode of the Tailwind Marketing Podcast, Carlos Corredor sits down with Matt Fiel, Executive VP at Penrod, to discuss how businesses can build great marketing teams even with limited resources. Matt shares his insights on how to allocate marketing budgets, the importance of knowing when to outsource specialized tasks, and how to structure…
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Using AI in Marketing Without Putting Your Company’s Data at Risk
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40:58In this episode of the Tailwind Marketing Podcast, host Carlos Corredor speaks with Scott McCollum, Director of Product Marketing at Blue Mantis. They discuss the unique challenges mid-market companies face in IT marketing and security. Scott shares how these companies often juggle limited resources while trying to address both marketing and cybers…
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Value Propositions That Stand Out for Tech Services Companies
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42:33In this episode of the Tailwind Marketing Podcast, Carlos Corredor talks with Paige Galley, Marketing Director at Prime Secure, about building a value proposition that stands out in a crowded IT market. Paige explains why being specific and measurable is key; instead of saying, "We have great people," she shows how to back it up with proof that bui…
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A Smarter Way to Run LinkedIn Ads: Get Targeting, Budget, Content and Creatives Right
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1:06:32In this episode of the Tailwind Marketing Podcast, host Carlos Corredor speaks with Tanner Stolte, Senior Customer Success Manager at LinkedIn. Tanner breaks down how to effectively use LinkedIn Ads to drive both awareness and lead generation. He highlights the importance of blending LinkedIn's high-quality leads with the volume from cheaper platfo…
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How to Create B2B Content That Shows Expertise and Sounds Human
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47:45In this episode of the Tailwind Marketing Podcast, host Carlos Corredor speaks with Ellie Behling, Content Director at Modus Create, about the key principles behind creating B2B content that truly connects with your audience. They explored the importance of aligning your content with both your audience's needs and your company's strengths. It’s not…
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The Three Pillars of IT Growth: Process, Automation, and Visibility
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34:36In this episode of the Tailwind Marketing Podcast, host Carlos Corredor talks with Michael Johnson, Director of Growth at Fast Slow Motion, to discuss the core principles of building scalable business systems using CRMs like Salesforce and HubSpot. Michael shares insights into the evolving role of CRM platforms, emphasizing the importance of proces…
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Making Sustainability Data Actionable in Marketing
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54:52In this episode of the Tailwind Marketing Podcast, host Carlos Corredor speaks with Jen Brown, Marketing Director at Worldly, about the evolving role of sustainability as a core business priority. Jen shares how businesses can use data to manage risk, deliver value, and build stronger supply chains. Listen in to discover how clear messaging, action…
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How Original Content is Changing ERP Marketing
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45:38In this episode of the Tailwind Marketing Podcast, host Carlos Corredor speaks with Dan Aldridge, Marketing Director at PCG, about the evolution of ERP marketing and the growing importance of education over selling. Dan shares how his experience as a consultant shapes his marketing approach, emphasizing the role of authenticity and content that tru…
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