Unfiltered takes on the biggest shifts in marketing technology. We spotlight what matters, who's leading (or lagging), and what's next. In Martech, clarity is power — and we're here to deliver it.
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Every week, Helen Guo interviews successful acquisition entrepreneurs, independent sponsors, and investors who have acquired businesses. Learn how to buy a business rather than starting one from scratch from those who have done it themselves.
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"What do the best online stores know that you don’t?" - If you sell online, run a DTC brand, or plan to launch — this podcast reveals the strategies top ecommerce operators are using right now to grow sales. Discover what’s working in 2026 to sell across Amazon, Shopify, and beyond, with insights on MarTech, D2C, B2B, social media, paid ads, AI, dropshipping, and more. Hear how successful ecommerce marketers think, test, and scale fast — and get the insider marketing & sales tactics to grow ...
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The AI Edge podcast is where AI pop culture meets marketing and technology. Hosted by trusted educators in the space: Shiv Gupta, founder of U of Digital, and Myles Younger, ad tech veteran, the show breaks down what’s actually happening in AI and what it means for marketers, agencies, and leaders focused on tech. Each week, Shiv and Myles cover the latest AI news, and dive deep with a guest into topics like the future of work with AI or how marketers should think about building their AI tec ...
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Join us each week to hear real-world advice and insights from senior marketing, growth and product leaders who are driving growth at the world's fastest growing companies.
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How to stand out with brokers and win competitive deals with Alejandra Barrera
1:06:49
1:06:49
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1:06:49You've probably done this… You found a listing you liked. You sent the NDA. Maybe you even fired off a quick note about your background and the things you’d like to learn. Then... nothing. A week later, the deal’s under LOI. No call back, no response to your request. Here's what you didn't see: That listing probably got 65 inquiries in the first fe…
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Battle of the Bots with Mariska Calabrese, beehiiv & Jakub Alexa, Omnivery
55:39
55:39
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55:39Email feels free, but the economics are brutal: zero-cost sending makes abuse infinitely scalable. In this episode, Jacqueline sits down with Mariska and Jakub to unpack the "bot layer" that's quietly wrecking modern email: security scanners, crawlers, and malicious automation that inflate clicks, poison dashboards, and trigger the wrong automation…
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How To Launch A Clothing Brand In 2026 With Zero Inventory — Paul Yu | How To Build A Clothing Brand Without Minimum Order Quantity, Why MOQs Kill Brands, How To Source Without Risk, Why Niche Selection ...
23:42
23:42
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23:42In this episode, we explore how to launch a fashion brand without the risk of buying huge amounts of inventory upfront. Paul Yu, Founder and CEO of eProlo, explains how modern supply chains allow sellers to start small and test products before committing to large orders. He shares how his platform helps over 1.6 million sellers use custom branding …
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Ep 6. AMA Episode: Agency Jobs, Sycophant AI, and Data Snake Oil
24:06
24:06
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24:06No guest this week, just Shiv and Myles answering listener questions in their first-ever mailbag episode. And the questions got deep. Will agency jobs disappear or are we headed back to a Mad Men era? What does a fully AI-enabled agency actually look like (and which ones are about to fail)? How do you trust AI to build client profiles when ChatGPT …
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Farewell, 2025 — what a year. It marked the revival of Making Sense of Martech, and we owe it all to you and the incredible guests who took a chance on us. Here are a few standout moments. Wishing you happy holidays and a brilliant new year! Connect & Subscribe Subscribe to Making Sense of Martech wherever you get your podcasts. Engage with the com…
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Merry everything and more. Here's your very own present from us to you! Connect & Subscribe Subscribe to Making Sense of Martech wherever you get your podcasts. Engage with the community on Reddit and follow Making Sense of Martech on LinkedIn, and don't forget to like and subscribe on YouTube. Leave a review, share with your team, and send us your…
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Ep 5. The AI Platform Wars Are Over, featuring Simon Poulton of Tinuiti
46:25
46:25
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46:25Simon Poulton searched for toilets in Google's AI Mode and saw his first AI-generated ad. That moment confirmed what he's been saying for months: Google's already won the AI platform wars, and OpenAI has 12 months to prove otherwise. This week, hosts Shiv Gupta and Myles Younger sit down with Simon Poulton, EVP of Innovation & Growth at Tinuiti, to…
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How These 2 Partners Met on Craigslist & Ended Up Buying 15 Companies Together | Joe Van Deman and Colin King
1:05:54
1:05:54
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1:05:54This week's episode starts with a horror story. Joe and Colin from Circle City Capital Group bought their first business together in 2018. After meeting on Craigslist (yes, seriously) They bought an overnight delivery route business specializing in auto parts. They started with 5 routes and put in less than $100k to acquire the business. But on the…
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How To Start A Profitable Ecommerce Business In 2026 — Ben Knegendorf | How To Launch In 30 Days, How To Find High-Ticket Products, Why The Buyer Comes First, Why Google Shopping Works Best, Why Passionate ...
25:29
25:29
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25:29In this episode, we discuss how to start a profitable e-commerce business in 2026 without wasting money or burning yourself out. Ben Knegendorf, Co-Founder at dropshipbreakthru.com, shares why most new sellers fail early, what makes high-ticket dropshipping safer and more profitable, and the essential steps to take in your first 30 days. Topics dis…
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2026 Predictions: Agents, AI Decisioning, & The Techstack
29:38
29:38
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29:38As 2025 closes out, Juan and Jacqueline team up with Keanu Taylor, The Martech Weekly's Head of Research, to read the tea leaves on what 2026 has in store for marketing technology. Their forecast is a "make or break" year in which the winners won't be the loudest early adopters, but the teams whose data and operating habits are clean enough for AI …
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Ep 4. The Great Agentic Commerce Discussion, featuring Andrew Lipsman
38:34
38:34
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38:34Myles wrote a piece saying agentic commerce is coming fast. Andrew Lipsman rebutted, calling it a "collective hallucination." The discussion got interesting, so we brought it to the podcast. This week, hosts Shiv Gupta and Myles Younger sit down with Andrew Lipsman, Independent Analyst & Consultant in Retail Media, to hash out whether AI agents sho…
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What Really Makes Shoppers Buy (Discount Code Study) — Cara Marin | The Discount That Drives The Most Sales, How To Scale Shopify Promotions, Why Unique Codes Stop Leaks, How Big Brands Scale Discounts ...
19:34
19:34
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19:34In this episode, we tackle the problem almost every Shopify merchant knows: discount codes. Cara Marin from Seguno shares the learnings from their massive benchmark report on 162,000 real discount campaigns. She reveals how top brands scale promotions the smart way, using unique, personalized discount codes to avoid leaks, prevent shrinking margins…
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This MLB Player Acquired A Street Sweeping Company With $0 Down And Grew It By 5x In 13 Months
40:12
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40:12By Helen Guo
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Make Martech Cool Again: A Conversation with Jason Lyman, Customer.io's CMO
28:36
28:36
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28:36"Marketing to marketers is the dream job, but it makes everything that much more high stakes." – Jacqueline In this Hot Seat episode, Jacqueline sits down with Jason, CMO at Customer.io, to ask a simple question: what would it actually take to make martech cool again? Drawing on stints at Dropbox, BetterCloud, and Microsoft, he unpacks how brand st…
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Ep 3. The AdTech and MarTech Divide Is Dead, featuring Heather Macaulay, President, MadConnect
35:21
35:21
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35:21Black Friday 2025 was the inflection point: AI shoppers converted at double the rate, AI traffic surged 805%, and brands finally learned that if AI can't see you, you don't exist. This week, hosts Shiv Gupta and Myles Younger are joined by Heather Macaulay, President of MadConnect, to break down what the Black Friday data actually means, unpack Sco…
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How Your Work Group Chat Is Quietly Ruining Your Business — Guy Weiss | Why An Always-on Culture Drains Teams, Why Mixed Chats Risk Company Data, How Your Business Data Gets Lost, How Smart Integrations ...
25:45
25:45
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25:45In this episode, we dive into the silent killer of e-commerce team productivity: using personal chat apps for work. Guy Weiss, CEO and founder of ZenZap, shares how relying on apps like WhatsApp can quietly harm your business through security risks, employee burnout, and lost data. He reveals the "hidden cost" of the "always on" culture and explain…
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[Greatest Hits] How This Big Law Partner Rolled Up 3 MarTech SaaS Companies In 20 Months And Sold to PE
1:05:10
1:05:10
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1:05:10Join me as I interview Brian Wolfe, a lawyer, small business investor, and PE and search fund professor. Brian founded Funded Ventures, which partners with builders to buy and build small businesses. Their first platform which was formed to acquire SaaS companies in the martech space successfully exited to Alpine Investors after 3 completed acquisi…
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How I Built a 480-Episode Business Podcast — Claus Lauter | How The Show Became A Full-time Business, Why Most Podcasts Fade, What Makes Podcast Growth Slow, How The Show Makes Money, How Listeners Can ...
10:52
10:52
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10:52In this episode, Claus Lauter, host of the Ecommerce Coffee Break Podcast, dives into his journey of building the show. He gives a recap of 2025, shares lessons learned from growing a slow social channel, and explains how the podcast evolved from a side project into a full-time, monetized business. He also highlights the growing impact of AI on onl…
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Adobe's Semrush Gamble, BFCM Enters the Upside Down, & AI-Washed Earnings
50:59
50:59
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50:59"Adobe didn't just buy an SEO tool – it bought a negotiating position with the AI overlords of discovery." – Juan Jacqueline and Juan unpack what "more human" marketing actually looks like when AI is mediating everything from search to Black Friday deals. They break down Adobe's acquisition of Semrush, quarterly Martech earnings, the Black Friday/C…
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He's acquired 50+ online businesses making $200k+ / month. (Here's how he does it) | Jacky Chou
40:33
40:33
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40:33In this week’s episode, we're diving into the world of online business acquisitions with Jacky Chou. He's built a portfolio of 50+ online businesses over the last 10 years. And today, he runs ~20 revenue-generating assets doing around $200K/month. And he shares all of it publicly online… But here's what makes this episode fascinating: Jackie doesn'…
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Is Your Inbox Insured? Deliverability is The Ultimate Insurance Policy with Matt McFee, CEO of Inbox Monster
34:14
34:14
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34:14"If you're not treating deliverability as revenue insurance, you're already losing money." — Matt This Hot Seat episode puts Matt McFee, an email veteran and founder of Inbox Monster, under the microscope. Jacqueline digs into how he went from Wall Street and Yahoo to co-founding BriteVerify, acquired by Validity, and why he thinks most brands are …
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Friendly Fraud: The Silent Killer Putting Your Ecommerce Margins At Risk — Simon Wijckmans | How To Stop Friendly Fraud, Why It Kills Your Margins, How To Prevent Chargebacks, What A 0.5% Fraud Rate Really ...
20:21
20:21
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20:21In this episode, we dive into the silent profit killer known as friendly fraud and chargebacks. Simon Wijckmans, Founder and CEO of cside, shares how these false chargebacks risk your margins and payment accounts. He explains what friendly fraud is, why it's so hard to fight, and how client-side security intelligence, combined with new programs lik…
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STOP Losing Money: How to Implement Profit First — Karl O'Brien | How To Find Your Hidden Cash Cows, What “Profit First” Means, How To Use Contribution Margin, Why Discounting Harms LTV, And Why Acquiring ...
24:21
24:21
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24:21In this archive episode, we dive into the concept of “Profit First” E-commerce and why focusing solely on revenue can lead to big surprises. Karl O'Brien, Co-Founder of Store Hero, an e-commerce analytics tool, shares how their system helps store owners avoid common financial pitfalls by shifting their focus from top-line sales to bottom-line profi…
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[Greatest Hits] He owns 4 gyms but he's never been to any of them. (Here's How) | Bill Haig
55:29
55:29
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55:29This week’s episode with Bill Haig is one of the most impressive absentee owner stories we’ve featured. Bill owns 4 gym locations in Northern Virginia…. But he’s never been inside any of them. That’s a lot of first time business buyers’ dream. A ‘passive business’. But how did he get here? Bill was an Army officer who bought his first gym with zero…
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Privacy by Design & Ethical AI with David Joosten, Cofounder of GrowthLoop
40:09
40:09
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40:09"Zero party data reflects what customers say they want; first party data reveals what they actually do." – David In this Hot Seat episode, Jacqueline sits down with David Joosten, co-founder of GrowthLoop and coauthor of First-Party Data Activation, to unpack why so many brands are "doing" first-party data yet still serving generic experiences. The…
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Ep 2. Synthetic Audiences and the $50B Question, featuring Chad Reynolds, CEO Vurvey Labs
42:57
42:57
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42:57The big questions: Are we teaching AI to tell us what we want to hear? If AI only knows the past, who discovers the future? And what happens to the $50 billion market research industry? This week, Shiv Gupta and Myles Younger dive into the biggest AI announcements shaking up advertising right now, including the Amazon vs. Google AI agent wars and w…
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How to Win Meta Ads with UGC (Finally) — Donatas Smailys | Why UGC Volume Wins, What Meta's Andromeda Algorithm Loves, Why Authentic Beats Polished AI, Why Trust Becomes Key, What Human-First AI Means ...
24:13
24:13
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24:13In this episode, we dive into how AI is accelerating the shift in user-generated content for advertising. Donatas Smailys, Co-founder and CEO of Billo, shares why social algorithms now demand high-volume content, his view on using AI as a scaling tool for real human creators (not for generating fake humans), and the crucial role of authenticity and…
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-$350k → $13M/Yr: From failed acquisition to HVAC rollup | Nathan Lenahan
53:57
53:57
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53:57Your first business acquisition wipes out your life savings. Your brother has to sell his house to cover the debt. You sell a property just to get back to zero. Most people would never touch a business deal again. Nathan Lenahan bought 4 more and built a $13M/year HVAC business. His story involves 5 acquisitions, 1 catastrophic failure, and 4 wins …
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AI's Report Card, The BFCM Machine, & Why Attribution Sucks
52:36
52:36
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52:36"92% of enterprises say AI is a priority, and 78% also say they can't integrate it." — Juan In this Office Hours episode, Jacqueline Freedman and Juan Mendoza unpack the biggest Martech realities of the season: record-breaking BFCM performance and the widening "AI hype gap." From $10.8 billion in U.S. online spending (69% on mobile) to reports reve…
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You're Asking For Reviews WRONG! (The Easiest Way To Get 5 Stars) — Daan Vaneker | How To Get A Quick Review Boost, What Makes Reviews Real, Why Negative Reviews Help, How To Respond To Bad Reviews, What ...
23:11
23:11
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23:11In this archive episode, we dive into the power of social proof and why trust building is essential for e-commerce success. Dan Vaneker, CEO and founder of trustprofile.com, shares his insights on how web shops can enhance trustworthiness through customer reviews and trust pages. He explains why customers rely on reviews before buying, how small sh…
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Ep 1. AI Edge: Where AI Meets Pop Culture, featuring guest Krish Raja
32:43
32:43
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32:43Welcome to Episode 1 of The AI Edge Podcast! Hosts Shiv Gupta and Myles Younger kick off the show with guest Krish Raja, AI expert and founder of AI Literacy, to break down the biggest AI stories shaking up marketing and advertising right now. This week: Coca-Cola doubles down on their controversial AI-generated holiday ad (yes, the one with the sl…
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STOP Sending Bad Emails! The $10K Segmentation Secret — Andriy Boychuk | How To Grow Your Email List Fast, The Four Key Segments To Target, What Segmentation Does For Revenue, Why Automations Drive Sales ...
24:50
24:50
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24:50In this archive episode, we dive into email marketing strategy and how e-commerce merchants can maximize its potential. Andriy Boychuk, founder at flowium.com, an email marketing agency for e-commerce, shares strategies for improving your setup, metrics, and overall performance. He explains how to effectively grow your email list before major sales…
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$50k → $5M buying declining healthcare businesses (here's how) | Devin Fitzgerald
51:27
51:27
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51:27Devin Fitzgerald acquired 2 declining home healthcare businesses in the Boston area over the last few years and successfully turned them around. He did it with some of the most creative financing we’ve seen on the show. And he’s already working on acquisition #3 (which is 4x bigger than all of his current businesses combined). At some points his st…
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Don't Get Catfished By AI with Brian Minick, COO of ZeroBounce
46:03
46:03
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46:03"Curiosity is the number one trait I'm looking for when hiring." — Brian Minick Jacqueline and Brian Minick, COO of ZeroBounce, get practical about AI's impact on hiring, email deliverability, and Martech operations. They unpack how AI is reshaping hiring, from candidates using copilots during interviews to the ethical implications of automation in…
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Agentic Commerce Explained: How AI Search is Reshaping eCommerce — Erik Wikander | Why Old SEO Is Dead, How Small Brands Can Win, How to Win in AI Search, How to Optimize Products for AI, What Is Agentic ...
33:43
33:43
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33:43In this episode, we dive into the massive shift impacting online sellers as shoppers use ChatGPT and other AI search tools for product discovery. Erik Wikander, CEO and co-founder of Wilgot.ai, unpacks the concept of agentic commerce — where AI completes the end-to-end purchase for the user. He shares what this revolution means for D2C brands, why …
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AI Kills SEO: Master GEO For Ecommerce — Claus Lauter | Why AI Is The New Search, What Generative Engine Optimization (GEO) Means, How To Use GEO, How ChatGPT’s New Checkout Changes Marketing, How To Optimize ...
14:02
14:02
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14:02In this episode, Claus Lauter, host of the Ecommerce Coffee Break Podcast, breaks down how AI is reshaping Q4 e-commerce strategy. He explains the rise of Generative Engine Optimization (GEO) — the new way to stay visible in AI-driven search — and shares practical tips on managing high ad spend while keeping profits strong. Claus also talks about t…
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Adios Ohana, AWS Meltdown, & Overcoming Analysis Paralysis
41:23
41:23
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41:23"You're supposed to be your customer relationship management platform of the era, and you're not listening to your very own customers." — Jacqueline Freedman Jacqueline and Juan dissect Salesforce's Dreamforce rebranding of all major products to Agentforce, the erosion of its once-strong Ohana culture, and Benioff's billionaire behavior. They unpac…
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Black Friday Marketing Tips — Nathan Ho | How To Run BFCM Deals, Why To Prep Early For Black Friday, Why Free Gifts Boost Cart Size, How Gifts Help Launch New Products, Why Tiered Promos Boost AOV, How ...
13:05
13:05
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13:05In this episode, we dive into how to run the best promotions for Black Friday and Cyber Monday (BFCM). Nathan Ho, Product Manager of EasyGift, shares his experience and advice on structuring promotions, using tiered spending to increase average order value, and the power of free gifts. He also discusses different marketing strategies like scheduled…
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The Hidden Post-Purchase Tool That Boosts Revenue 10% | Why Bad Tracking Hurts CX, How Tracking Upsells Boost Sales, How Smart Tracking Emails Drive Revenue, What Basic Tweaks Add 3%, Why Full Optimization ...
18:54
18:54
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18:54In this episode, we dive into how to turn order tracking from a common customer service headache into a powerful engine for repeat sales and revenue growth. Andrey, founder of parcelous.com, shares the major mistakes online sellers make after an order is placed and how a branded tracking page can solve customer frustration while simultaneously gene…
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Martech Avengers Assemble with Neha Dadbhawala, Head of Martech at SEEK
31:05
31:05
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31:05"Marketing engineers are the lovechild of marketers, product managers, and software engineers — they're the Avengers of your Martech stack." - Neha Dadbhawala Join Jacqueline and Neha, Head of Martech at SEEK, to unpack how the role of the marketing engineer is reshaping the future of digital transformation. Neha shares her insights on bridging str…
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How Retailers Can Unlock Growth With AI — Ravi Achanta | How To Grow Your Sales With AI, How AI Turns Your Store Data Into Growth, Why You Should Trust Data, How AI Boosts Customer Loyalty, How AI Saves ...
32:39
32:39
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32:39In this episode, we dive into the challenge faced by independent retailers in competing with giants like Walmart. Ravi Achanta, CEO and Co-founder of RSA America, shares how AI is leveling the playing field. He explains how small retailers can use the data they already have to drive growth, boost customer loyalty, and uncover new revenue, making po…
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How Small Sellers Can Compete With Giants — Nahar Geva | New Data-driven Strategies For Ecommerce Growth, How To Beat Big Brands, What Makes A Product A Winner, Systems And Habits You Need To Master Data ...
34:16
34:16
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34:16In this episode, we dive into data-driven strategies that help small sellers spot winners, optimize listings, and scale their e-commerce business without wasting time. Nahar Geva, Founder and CEO of ZIK Analytics, explains why shifting your mindset and embracing data is key to beating big brands. He shares his story of founding ZIK Analytics from a…
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He broke ALL the rules of acquisition and still succeeded | Walker Yarbrough
1:06:11
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1:06:11I’m very excited to share this week’s interview with Walker Yarbrough. He started off with long hours in Investment Banking until he looked up at his bosses and he realized he didn’t want their job (at all). "Even once they'd climbed the ladder, they still just didn't have a lot of control of their own time…They were doing great by a lot of standar…
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Stop the Hype: Taylor Swift's Loyalty Playbook, Zeta & Marigold Merger, and Braze's AI
33:37
33:37
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33:37"Don't be the Taylor Swift of Martech." - Jacqueline Freedman Jacqueline and Juan break down three of the latest Martech moments: Braze's all-in AI decisioning push, Zeta Global's acquisition of Marigold, and what Taylor Swift's marketing playbook reveals about loyalty and fandom. Drawing from recent Martech World Forum events in London and San Fra…
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How To Hit $1M Months Selling Hard Gated Brands — Aaron O'Sullivan | Why New Amazon Stores Are Gated, How To Buy Aged Amazon Accounts, The Process Of Selling Amazon Stores, Why Multiple Stores Mitigate ...
27:45
27:45
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27:45In this episode, we dive into the challenges of selling on Amazon, including gated brands and slow cash flow. Aaron O'Sullivan, co-founder of Sellmyselleraccount.co and ecomstores.com, shares how acquiring aged Amazon seller accounts can provide instant access to restricted categories, speed up cash flow cycles, and mitigate the risk of account sus…
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How AI Is Changing The Way Amazon Is Managed — Jerry Vida | How AI Is Automating Amazon Optimization, Why Focusing On Profit Is Better Than On Revenue, Why Manual Amazon Tasks Hurt Business Growth, Why ...
21:54
21:54
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21:54In this episode, we dive into how AI is reshaping Amazon store management and the critical importance of focusing on profitability over just top-line revenue. Jerry Vida, Co-founder of Peak ROAS, shares how his agency helps seven- and eight-figure brands scale by leveraging AI to streamline time-consuming tasks like PPC and listing optimization. He…
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The Need to Ban "Inbox Placement" with Lauren Meyer, CMO of SocketLabs
37:40
37:40
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37:40"There's a big difference between consent and attention — you still have to earn the attention." - Lauren Meyer Lauren Meyer, CMO of SocketLabs, joins Jacqueline Freedman on The Hot Seat to discuss what marketers get wrong about email. She shares how to earn real engagement, why "inbox placement rate" is a lie, and how to prove email's value inside…
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How to Increase Shopify Revenue with Bundles and Bulk Discounts — Katie Keith | Why Stores Struggle With AOV, How Bundles Boost Sales and AOV, What Discount Pricing Psychology Works Best, Why B2B Versus ...
20:31
20:31
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20:31In this episode, we unpack bundles and bulk discounts and how they can nudge customers to buy more and boost revenue. Katie Keith, Founder and CEO of Barn2 Plugins, shares why most stores struggle to increase average order value and how her new Shopify app bridges the gap between different discount strategies. She also provides a masterclass on dis…
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From Laid Off & Mid-Divorce to a $1.3M / Year Business (with 100% Seller Financing) | Raj Kankaria
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49:11I’m very excited to share this week’s interview with Raj Kankaria. It is an absolute roller coaster involving layoffs, divorce, rappers, a quarter life crisis, and Raj buying a $1.3M / year business with 100% seller financing. Here’s a sneak peak: Raj was a former army vet who had gotten a job at Citi Bank as an investment banker. He had just been …
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Scaling to Billions: How to Design the Ideal Stack with Natalie Miles Fuerst of Grammarly
43:07
43:07
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43:07"No one's data is perfect. I think the biggest challenge though ends up being more people, because what often happens is that companies of a certain scale, marketing orgs of a certain scale, oftentimes we start adding on products or new verticals and we hire marketers to be in charge of those specific products or verticals, and they work in these s…
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