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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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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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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It Starts With a Prompt. It Ends With a Point of View: How to Create Great Copy
32:46
32:46
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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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Send 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
11:54
11:54
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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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Why the 1% Rule Will Make You Go Broke in Real Estate
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6:34Send 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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I Lost My Job as a Pilot — Here’s How I Survived (and What I’d Do Differently)
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8:55Send 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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Why I Rent While Owning Millions in Real Estate
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8:10Send 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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How I Got Paid $125,000 to Buy a 4-Unit Rental With $0 Down
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6:29Send 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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Why I Haven’t Quit My Job (Even with 60 Rental Units)
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13:37
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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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13:28
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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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14:41
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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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How Im Investing In Real Estate Right Now (Despite High Prices)
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8:25
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8:25Send 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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I Hate Sales - But I Got My Real Estate License Anyway
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8:39Send 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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Flying Jets By Day... Living In My Moms Basement By Night
9:08
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9:08Send 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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I Own $5M In Real Estate... But I Still Rent
6:42
6:42
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6:42Send 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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My Rental Property Burned Down - I Still Made $100K +
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7:17Send 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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You Don't Need A $4,000 Course To Buy Rentals!!
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6:09
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6:09Send 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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Why Relationships Matter More Than Money (long term)
8:44
8:44
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8:44Send 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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My Best Rental Property of 2024 Made $13,926 (27% Return!)
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3:24Send 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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The Paradox of Playing It Safe: Why Inaction Is Riskier Than Failure
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3:49Send 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
27:13
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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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Your Down Payment's Best Friend: Measuring Real Estate Success
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5:38
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5:38Send 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 Simple Messaging Beats Clever Campaigns
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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 salespeople 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 clever campaig…
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A “Numbers First” Engineering Approach to Marketing Growth
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31:44
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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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44:55
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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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38:47
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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
1:06:32
1:06:32
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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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The Evolution of Demand Generation in B2B Marketing
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47:00In this episode of the Tailwind Marketing Podcast, host Carlos Corredor chats with John Vinson, Marketing Director at V-Soft Consulting, about the evolution of demand generation in B2B marketing and how it has evolved from what he calls the “wild west of digital marketing.” John shares insights on bridging the gap between marketing and sales, the r…
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How Agility in Search Marketing Strategy Can Give You the Edge
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40:05In this episode of the Tailwind Marketing Podcast, host Carlos Corredor speaks with Prasanna Dhungel, co-founder of GrowByData, on adapting to Google’s evolving SERPs and the role of AI in search. Prasanna shares how brands can stay competitive by experimenting with diverse content, monitoring the share of voice, and leveraging data signals. Listen…
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No Secret Sauce: The Real Recipe Behind Marketing Evolution
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21:47
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21:47In this episode of the Tailwind Marketing Podcast, host Carlos Corredor sits down with Rafael Moiseev, the VP of global marketing at Customertimes. They explore the shift from traditional siloed marketing to agile, integrated teams, the crucial role of orchestration in meeting modern marketing demands, and the impact of marketing intelligence on dr…
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The Spiderweb Content Approach To Improve SEO
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46:14Wade Poezyn is a Senior Digital and Demand Generation Marketing Manager at Transact Campus, a technology company simplifying campus payments and commerce for higher education institutions. With over nine years of experience, Wade has become an expert in fintech, digital transformation, AI, and B2B, B2C, and B2B2C marketing. He is passionate about h…
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Chiala Marvici is a fractional director with extensive experience spanning multiple industries. With over two decades in this profession, Chiala has made significant contributions to leading companies through digital transformations, particularly in the beauty, real estate, and IT services sectors. Beginning her career in the beauty industry, she h…
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Old-School Sales Tactics in Today's IT World
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36:11Bijan Abrahim is a Senior Sales and Marketing Officer at theITSupportCenter, which provides 24/7, immediate, expert IT help desk support for end users of Fortune 500 organizations. An enterprise sales professional with over a decade of industry experience, Bijan specializes in optimizing sales processes, driving marketing initiatives, and enhancing…
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Inga Finneke is the Marketing Director at Codal, which specializes in cutting-edge, data-driven strategies and solutions for enterprise brands and technology providers. With over a decade of experience in event management, branding, product marketing, and PR, Inga has a track record of designing strategic marketing programs and spearheading initiat…
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Ben Ryan is the Marketing Manager at Transact Campus, which simplifies campus payments and commerce for higher education institutions, offering products ranging from mobile ordering to NFC wallets. Focused on marketing directly to students, faculty, and parents, Ben brings a fresh perspective to B2B and B2B marketing with a solid grasp of both worl…
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An Entrepreneurial Approach to IT Marketing
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43:07Clay Tuten is the CMO at KeyMark, a leading business process automation software provider for major enterprises. With 27 years in the creative and marketing field, Clay has a diverse background, encompassing sports, apparel, construction, events, and technology through both digital and traditional marketing avenues. Recognized for his entrepreneuri…
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Eric Herzog is the Chief Marketing Officer at Infinidat, an enterprise data storage solutions provider. With a 40-year career in IT marketing focused on enterprise storage, Eric has held several executive roles spanning from product management to marketing. He has a track record of exceeding P&L targets and has worked at Fortune 500 companies like …
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