The Orita Podcast

Aaron Schwartz
  • 5.0 (3)
  • Marketing
  • Updated Weekly

Each week, I'm sitting down with the most interesting people in eCommerce - founders, investors, marketers, and agency leaders who are actually doing the work. We're skipping past the highlight reels and getting into the real stories that shaped their success.

  1. 6d ago

    Tailored Growth: Building Modern Citizen Without the Startup Script

    In this episode of The Orita Podcast, Aaron Schwartz sits down with Jessica Lee. Jessica started Modern Citizen with a small friends and family round, never raised again, and just celebrated ten years in business. Most of the funded brands from her era are gone. She has a theory about why. • The Gap Inc. training that most fashion founders never get: rotating through merchandising, inventory, production, and strategy before ever starting a brand • Why she believes CAC should be positive from the first transaction, and why betting on LTV never made sense to her in apparel • Not a workwear brand, but a brand for women who work: the psychographic positioning that has mothers and daughters shopping together • The white blazer of April 2020 and how a sub-fifteen-person team pivoted an entire fall assortment while big retail watched inventory arrive on boats • Sublease first, sign later: the real estate strategy that let a bootstrapped brand open stores in the two most expensive markets in America • Her reframe that stopped Aaron mid-sentence: retention is not a metric, it is whether you are delivering on the brand promise 👥 Meet the guest Jessica Lee, Founder and CEO at Modern Citizen 🎙 Hosted by Aaron Schwartz, Co-Founder and Co-CEO at Orita.ai 🎧 Chapters [00:00] Jessica Lee: Ten Years of Modern Citizen [00:37] The Gap Inc. Rotational Program: Learning the Business of Fashion [03:22] From Product Functions to the Strategy Group [06:00] Working M&A and Watching DTC Get Coined [08:00] Something Specific for Someone: The Modern Citizen Thesis [09:38] Building With a Business Partner and No Institutional Money [11:54] Ten Years In, Closer to the Brand Promise Than Ever [13:30] Psychographic Over Demographic: Mothers and Daughters Shopping Together [15:11] Why She Never Raised: Control, Discipline, and Product Market Fit [19:13] Coming From Retail: Knowing the Margin Structure From Day One [20:51] CAC Positive From the First Transaction [21:28] Two Years of Word of Mouth, Then the First Marketing Budget [23:52] Consistency Is the Superpower: We Thought You Were Huge [26:04] The First Thousand-Unit Bet and Learning to Take Risks [29:46] One Big Bet at a Time: Managing Founder Energy Through Four Kids [31:19] COVID: The White Blazer That Never Had a Chance [33:43] Showrooms, Subleases, and Re-Entering Stores in 2024 [37:57] Retention Is Whether You Deliver on the Brand Promise [40:25] Claude, Chat Walrus, and Freeing a Small Team From Admin Work 🌐 Check out Orita.ai for more episodes of The Orita Podcast, where we sit down with the most interesting operators, marketers, and founders in e-commerce to talk about what’s working right now. Hosted by the Orita team. Orita uses machine learning to help brands send smarter, more profitable marketing, by figuring out who actually wants to hear from you and when. 🚀 Get your free email audit from Orita, turn segments into superpowers: https://orita.ai 🎧 Listen on Spotify & Apple 📩 Subscribe for more founder‑grade retention intel

  2. Sep 14

    The Second Order Effect: Why the First Sale Is the Least Important One

    In this episode of The Orita Podcast, Aaron Schwartz sits down with Thomas Lalas. Thomas ran an AI startup that died the way most startups die: great at acquiring customers, terrible at keeping them. He has spent the last eight years making sure nobody he works with repeats that mistake. • The 90-day thesis: why the first three months after purchase decide almost everything about LTV, and what the best brands do inside that window • The subscription-only study: what 160 supplement brands revealed about buy box design, from OTP-first to the AG1 model to no one-time option at all • The Tidal effect: how accidental renewals inflate month-two retention and quietly destroy month twelve • Reading the retention curve like a diagnosis, including the call where Thomas guessed a brand's vertical from the shape of the curve alone • His LTV to CAC framework and the Goldilocks zone between 3.5 and 4 where brands can start stealing market share • The question neither Thomas nor Aaron can answer: why brands have unlimited budgets for acquisition and capped budgets for keeping the customers they already paid for 👥 Meet the guest Thomas Lalas, Director of Retention and Loyalty at Dose and author of Retention Economics 🎙 Hosted by Aaron Schwartz, Co-Founder and Co-CEO at Orita.ai 🎧 Chapters [00:00] Thomas Lalas: Retention Systems for Eight and Nine Figure Brands [02:14] The AI Startup That Died From Bad Retention [04:30] Why LTV Is Where the Money Is, Not ROAS [07:40] Email and SMS First: Prove the Economics Before Adding Channels [10:19] Why You Cannot Accelerate Retention Data [12:17] What It Takes to Work With Thomas: Risk, Patience, Speed [17:09] The First Thing He Audits: OTP to Subscription Ratio [19:39] The 160 Supplement Brand Study: Subscription Only Wins [22:14] The Tidal Effect: Accidental Renewals and the Month Two Trap [24:49] Guessing the Vertical From the Shape of the Curve [26:12] Every Brand Can Lift Retention Ten Percent [27:30] The LTV to CAC Goldilocks Zone: 3.5 to 4 [31:18] Retention Starts at the Ad, Not the Purchase [33:30] Do Not Hire Us First: When Post-Purchase Systems Cannot Save You [34:37] The Question Neither of Them Can Answer [37:52] Why He Wrote Retention Economics and Why Recharge Made It Required Reading [41:06] The People Worth Following in Retention 🌐 Check out Orita.ai for more episodes of The Orita Podcast, where we sit down with the most interesting operators, marketers, and founders in e-commerce to talk about what’s working right now. Hosted by the Orita team. Orita uses machine learning to help brands send smarter, more profitable marketing, by figuring out who actually wants to hear from you and when. 🚀 Get your free email audit from Orita, turn segments into superpowers: https://orita.ai 🎧 Listen on Spotify & Apple 📩 Subscribe for more founder‑grade retention intel

  3. Sep 14

    Special Delivery: Michael Epstein on Bringing Digital Precision to Physical Mail

    In this episode of The Orita Podcast, Aaron Schwartz sits down with Michael Epstein. Michael spent 25 years in ecommerce fixing what he calls nine-figure brands losing eight figures. The tool that kept working when nothing else did was the postcard. • Why turnarounds taught him that most struggling brands do not need magic, they need blocking, tackling, and a culture where people actually understand the numbers • The thesis behind PostPilot: every digital channel gets more crowded and expensive over time, while the mailbox gets emptier and postage stays capped • Two years of people laughing at direct mail, and the iOS 14 moment that changed everything • The acquisition AI story: an identity graph covering essentially every US household, and why data beats the old data-broker model • The biggest testing mistake brands still make, and why Black Friday is the worst possible time to try a new channel • Aaron on the subscriber fallacy: why being on your email list does not mean email is what moves someone to buy 👥 Meet the guest Michael Epstein, Co-Founder and Co-CEO at PostPilot 🎙 Hosted by Aaron Schwartz, Co-Founder and Co-CEO at Orita.ai 🎧 Chapters [00:00] Michael Epstein: 25 Years in Ecommerce, Two Co-CEOs [01:19] Nine-Figure Brands Losing Eight Figures: The Turnaround Years [02:20] The Spreadsheet Problem That Sparked Klaviyo for Direct Mail [03:55] Most Broken Brands Just Need Blocking and Tackling [08:54] Walking Every Employee Through the P&L [11:01] OKRs: Imperfect, Necessary, and Better Than Rowing in Circles [12:47] What Michael Misses About the Brand Side and What He Does Not [15:03] We Are the Customer: How Empathy Built PostPilot [17:29] The Law of S****y Click-Throughs and the Capped-Cost Mailbox [19:31] Two Years of Being Laughed At, Then iOS 14 Hit [21:24] Shopify and Klaviyo: The Integrations That Changed the Channel [22:33] Do Not Test Direct Mail on Black Friday [26:19] Why Brands Test Meta Seriously and Direct Mail With Pocket Change [29:04] Acquisition AI: An Identity Graph of Every US Household [32:08] What Is Next for Direct Mail [35:43] The Subscriber Fallacy: Email Signup Does Not Mean Email Converts [38:46] Take Off the Marketer Hat, Put On the Consumer Hat 🌐 Check out Orita.ai for more episodes of The Orita Podcast, where we sit down with the most interesting operators, marketers, and founders in e-commerce to talk about what’s working right now. Hosted by the Orita team. Orita uses machine learning to help brands send smarter, more profitable marketing, by figuring out who actually wants to hear from you and when. 🚀 Get your free email audit from Orita, turn segments into superpowers: https://orita.ai 🎧 Listen on Spotify & Apple 📩 Subscribe for more founder‑grade retention intel

  4. Aug 19

    Stay a While: Turning Subscriptions Into a Channel, Not a Checkbox

    In this episode of The Orita Podcast, Aaron Schwartz sits down with Gina Perrelli. Gina learned retention marketing driving a Mini Cooper for Red Bull, where the cans had to be chilled for two hours and could never be dented. That obsession with every touchpoint now runs Stay AI. • From Red Bull wings team to a Chapter 11 ski resort turnaround, and the consultant from that project who became her co-founder • Why the Shopify subscription API changed everything: subscription apps stopped being payment processors and became marketing tools • The breakup analogy for cancellation flows, and why a pre-survey screen is the leg up most brands are skipping • Why Stay refuses to build loyalty and stays laser focused on being the best at subscription, including the widget-based portal that lets every partner app plug in • The nine-month data warehouse bet that became Stalien, and the churn question it answered in 30 seconds that would have taken a human hours • Her hot takes: set up the pre-survey screen, add at least one upsell, and start using Claude before it blows past you 👥 Meet the guest Gina Perrelli, Co-Founder and CEO at Stay AI 🎙 Hosted by Aaron Schwartz, Co-Founder and Co-CEO at Orita.ai 🎧 Chapters [00:00] Gina Perrelli: Aaron's Favorite Thinkfluencer Joins the Pod [00:45] Red Bull Wings Team: Retention Marketing 101 in a Mini Cooper [03:42] Chilled Cans and No Ripped Jeans: What Premium Actually Means [08:19] Turning Down Red Bull, Burning the Suits, Finding the Ski Resort [09:31] Trial by Fire: Running Retention Through a Chapter 11 [10:23] Meeting Pearson: The Consultant Who Became Her Co-Founder [12:47] Conned Into Lunar Solar: It's Gonna Be Super Chill [14:49] NoCommerce: Everything You Shouldn't Do When Spinning Out an App [17:05] The Shopify Subscription API Moment That Sparked Stay [18:10] Denied at 3AM: What Gina Got Wrong About Building [20:28] Why Shopify Plus Is the Only Market That Makes Sense [22:00] The Series A Deck vs Reality: Saying No to Everything [25:41] Why Stay Will Never Build Loyalty [28:19] The Customer Portal Rebuild: Widgets From Every Partner [29:48] Subscription as a Performance Channel: Two Hours vs 20K on Meta [31:52] The Breakup Analogy: Pre-Survey Screens and Cancellation Flows [34:38] The Nine-Month Bet That Became Stalien [36:45] The Price Increase Question Stalien Answered in 30 Seconds [40:25] Universal Segments and the Personalized Portal Future [44:00] Gina's Hot Takes: Pre-Survey Screens, Upsells, and Claude 🌐 Check out Orita.ai for more episodes of The Orita Podcast, where we sit down with the most interesting operators, marketers, and founders in e-commerce to talk about what’s working right now. Hosted by the Orita team. Orita uses machine learning to help brands send smarter, more profitable marketing, by figuring out who actually wants to hear from you and when. 🚀 Get your free email audit from Orita, turn segments into superpowers: https://orita.ai 🎧 Listen on Spotify & Apple 📩 Subscribe for more founder‑grade retention intel

  5. Aug 18

    Retention by Design: Building Arcady Media and making AI useful for ecommerce

    In this episode of The Orita Podcast, Aaron Schwartz sits down with Tarun Kamath, Founder and CEO at Arcady Media. Tarun sold paper airplanes in grade two, got banned from PayPal at 14, and founded Arcady Media at 18. Three years later he runs a 35-person agency that Shopify named one of its most recommended. • Why Arcady treats email and SMS as a lever for cash conversion and liquidity, not just another marketing channel • The bottleneck analysis framework: find the one variable that matters, whiteboard everything that affects it, test aggressively on that alone • Inside Arcadia Intelligence, the internal tool that stores every campaign hypothesis and checks whether it did what the team intended • How winning a Stripe, Lovable, and Klaviyo hackathon became the first agentic tool on Klaviyo's app platform • The $250 bouquet story: how one flower brand emailed its way out of a guaranteed Valentine's Day sale • Aaron on rescue revenue, the $40 million found in dead contacts, and why SMS proves itself in a month while email takes three 👥 Meet the guest Tarun Kamath, Founder and CEO at Arcady Media 🎙 Hosted by Aaron Schwartz, Co-Founder and Co-CEO at Orita.ai 🎧 Chapters [00:00] Tarun Kamath: Founder of Arcady on His Fourth Coffee [01:57] Email as a Business Lever, Not a Marketing Channel [02:08] The Ecommerce Growth Formula: Furniture vs CPG [10:00] Slowing Down to Speed Up: How Both Companies Learned to Sell [11:50] Who Uses Orita Best: Business Fundamentals Over Attribution Gold [13:19] Build vs Buy: Anticipating Shopify and Klaviyo's Next Moves [15:30] Inside Arcadia Intelligence: Every Campaign Gets a Hypothesis [18:57] The Bottleneck Analysis: Lazy Marketing Done Right [20:42] The When Company and the What Company [22:08] The $250 Bouquet That Got Away [23:17] SMS Proves It in a Month. Email Takes Three. [25:09] The Frequency Distribution Problem Every Big Brand Has [29:48] Paper Airplanes, Roblox Trading, and a Lifetime PayPal Ban [31:00] From Casino Job at 15 to Founding Arcady at 18 [33:39] What Consumers Expect Now: Personalization or Unsubscribe [35:00] Custom Emails From Shopify Session Data: The Hackathon Winner [37:00] Why Agility Beats Pattern Recognition Right Now 🌐 Check out Orita.ai for more episodes of The Orita Podcast, where we sit down with the most interesting operators, marketers, and founders in e-commerce to talk about what’s working right now. Hosted by the Orita team. Orita uses machine learning to help brands send smarter, more profitable marketing, by figuring out who actually wants to hear from you and when. 🚀 Get your free email audit from Orita, turn segments into superpowers: https://orita.ai 🎧 Listen on Spotify & Apple 📩 Subscribe for more founder‑grade retention intel

  6. Aug 17

    How Did You Hear About Us: Matt Bahr on Post-Purchase Insights and AI

    In this episode of The Orita Podcast, Aaron Schwartz and Daniel Brady sit down with Matt Bahr, Co-Founder and CEO at Fairing. Matt has spent seven years answering one question: what actually drove that purchase? The answer is rarely what your attribution model says. • How a customer's $40K influencer gifting problem became Fairing, built in two weeks as a side project that outgrew the main business • Why influencers are the most underutilized channel right now, including brands over $20M in GMV that spend nothing on Meta • The four questions every brand should ask post-purchase, and the CRO question that saved brands tens of millions • Why Fairing wants marketers to never touch their attribution survey again, and the methodology bias most brands introduce without knowing • What tens of millions of monthly responses reveal about AI-driven purchases, and why nobody is using Claude for product discovery • Aaron and DB on why sending more makes less, and the hardest question Aaron asks on every sales call 👥 Meet the guest Matt Bahr, Co-Founder and CEO at Fairing 🎙 Hosted by Aaron Schwartz, Co-Founder and Co-CEO at Orita.ai Daniel Brady, Co-Founder and Co-CEO at Orita.ai 🎧 Chapters [00:00] Matt Bahr: The Man Who Introduced Aaron and DB [01:57] Cold Calls at Yext to First Hire at Master & Dynamic [06:03] The $40K Gifting Problem That Became Fairing [07:50] Built in Two Weeks: The Side Project That Won [09:55] What Fairing Actually Solves: The Top of Funnel Problem [13:37] Building Where the Lampposts Are: DB's Measurement Theory [15:33] Influencers: The Most Underutilized Channel in Commerce [17:31] TV Is the Hardest Channel to Crack. Here's the Nuance. [19:18] New vs Returning: Splitting the Survey Questions [22:37] The 30% Response Rate Holy Grail and How to Hit It [25:07] The Four Questions Every Brand Should Be Asking [27:59] Why Marketers Should Never Touch Their Attribution Survey [31:30] What Tens of Millions of Responses Say About AI Shopping [33:23] Should Brands Sprint Toward AEO Right Now [35:06] MCP Servers and the Agentic Future of Commerce Data [44:18] Matt's Email Gripe: Sending More Makes More. Until It Doesn't. [49:42] The Hardest Question Aaron Asks on Every Sales Call 🌐 Check out Orita.ai for more episodes of The Orita Podcast, where we sit down with the most interesting operators, marketers, and founders in e-commerce to talk about what’s working right now. Hosted by the Orita team. Orita uses machine learning to help brands send smarter, more profitable marketing, by figuring out who actually wants to hear from you and when. 🚀 Get your free email audit from Orita, turn segments into superpowers: https://orita.ai 🎧 Listen on Spotify & Apple 📩 Subscribe for more founder‑grade retention intel

  7. Aug 5

    Chief of Stack: Shopify, Smarter Operations, and What Comes After the Search Box

    In this episode of The Orita Podcast, Aaron Schwartz sits down with Matt Cohn, Technical Chief of Staff at Shopify. Matt started on the brand side figuring out how to get Paw Patrol toys into kids hands digitally. Now he sits in the Office of the President at Shopify reporting to Harley Finkelstein and watching three million merchants navigate the fastest-moving period in commerce history. The merchant empathy he built at Spin Master is still the thing he relies on most. • Why the CSM role has fundamentally changed and what it means that the Venn diagrams between AE, SE, and CSM are converging • The great data cleanup: what every brand needs to get right in the next 12 months so they show up correctly in ChatGPT, Perplexity, and Google AI Mode • How Shopify thinks about Universal Commerce Protocol and why structured product data is now a competitive moat not a back-office chore • What Mattel and Barnes & Noble got right about modernizing without losing what made their brands matter in the first place • Why coding agents are a bigger leap forward from LLM chat than LLM chat was from traditional search • The tension both Aaron and Matt see in the ecosystem right now: everyone says they do what the best tools do, almost nobody does it as well 👥 Meet the guest Matt Cohn, Technical Chief of Staff at Shopify 🎙 Hosted by Aaron Schwartz, Co-Founder and Co-CEO at Orita.ai 🎧 Chapters [00:00] Paw Patrol to Shopifys Office of the President [01:46] What Spin Master Taught Matt About Merchant Empathy [03:35] The Toy Verticals Dirty Secret: Child Consumes Parent Purchases [05:17] Omnichannel Before It Had a Name: Spin Master in 2017 [07:38] Why Matt Left Brands for Merchant Success at Shopify [09:44] How the MSM Role Has Fundamentally Changed [12:25] AI Lowered the Bar for Information Now What Is a CSM Worth [14:18] Working in Harleys Office: What the Job Actually Looks Like [16:29] 150 Product Updates: How Matt Actually Keeps Up [17:46] Rewriting the AI Guide for 2026: What Moved to the Top [21:04] Sidekick and the Internal Operations Opportunity [23:08] Iterate First: The Habit That Separates Fast Builders [27:40] Personalization Is Everywhere Now and Mostly the Same [29:16] AI Shopping Discovery: How to Show Up in ChatGPT and Perplexity [34:38] Mattel Adults and Barnes & Noble: What Legacy Brands Got Right [40:28] Why Aaron Screwed Up His Brand and What He Would Do Differently 🌐 Check out Orita.ai for more episodes of The Orita Podcast, where we sit down with the most interesting operators, marketers, and founders in e-commerce to talk about what’s working right now. Hosted by the Orita team. Orita uses machine learning to help brands send smarter, more profitable marketing, by figuring out who actually wants to hear from you and when. 🚀 Get your free email audit from Orita, turn segments into superpowers: https://orita.ai 🎧 Listen on Spotify & Apple 📩 Subscribe for more founder‑grade retention intel

  8. Jul 24

    Behind the Metric: How Hark Turns Customer Stories Into Growth Signals

    In this episode of The Orita Podcast, Aaron Schwartz sits down with Fran Brzyski, Co-Founder & CEO at Hark and Lisa Eng, Head of Marketing at Hark. Fran and Lisa went to college together. Fran ended up on Lisa's couch a lot. Now she runs marketing at the company he founded. That context actually matters for how they talk about Hark. The argument they make together is a simple one: retention marketers are drowning in metrics and barely talk to their customers. Hark is trying to fix that, not by aggregating your existing reviews and support tickets, but by going out and getting net new zero-party data at specific moments in the customer journey. Fran has a line that stuck with me. An insight is not an observation. An insight is when you thought a cohort would behave one way and they behaved another. Most feedback tools give you observations. Hark is trying to give you the other thing. Lisa spent 13 years on the brand side at Spanx, TAR Cosmetics, and Shutterfly before joining. She calls it the dark side. She means it affectionately. Mostly. 👥 Meet the guests Fran Brzyski, CEO at Hark Lisa Eng, Head of Marketing at Hark 🎙 Hosted by Aaron Schwartz, Co-Founder and Co-CEO at Orita.ai 🎧 Chapters [00:00] Two Guests One Podcast: Fran and Lisa From Hark [00:36] Lisa Eng: 13 Years on the Brand Side Then the Dark Side [01:34] Fran Brzyski: JP Morgan Six Months Then Never Again [03:35] What Hark Actually Does and Why Surveys Are Broken [04:46] Walk Me Through It: What Happens When a Brand Signs On [07:28] Feedback Is Still Batch and Blast: Lisas Lifecycle Framing [09:27] The Aha Moment: When Clients See the First Responses Roll In [11:04] Is There Still a Place for Surveys [13:37] How Gen AI Changed Harks Product Vision [15:46] Who Actually Buys Hark and Who Feels the Pain First [18:35] Why DTC and Not Every Industry at Once [20:25] From Brand Side to Vendor Side: What Lisa Had to Unlearn [22:43] Where to Drop Hark First in the Customer Journey [25:18] When Feedback Cuts Out the AB Test Entirely [28:36] What Brands Should Not Be Actioning on Feedback [33:19] The One Unique Asset Every Brand Is Sitting On and Ignoring 🌐 Check out Orita.ai for more episodes of The Orita Podcast, where we sit down with the most interesting operators, marketers, and founders in e-commerce to talk about what’s working right now. Hosted by the Orita team. Orita uses machine learning to help brands send smarter, more profitable marketing, by figuring out who actually wants to hear from you and when. 🚀 Get your free email audit from Orita, turn segments into superpowers: https://orita.ai 🎧 Listen on Spotify & Apple 📩 Subscribe for more founder‑grade retention intel

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Ratings & Reviews

5
out of 5
3 Ratings

About

Each week, I'm sitting down with the most interesting people in eCommerce - founders, investors, marketers, and agency leaders who are actually doing the work. We're skipping past the highlight reels and getting into the real stories that shaped their success.

Information

  • Creator
    Aaron Schwartz
  • Years Active
    2025 - 2026
  • Episodes
    101
  • Rating
    Explicit
  • Copyright
    © Aaron Schwartz
  • Show Website
    The Orita Podcast