PODCAST · business
The Orita Podcast
by Aaron Schwartz
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.
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76
Absolute Advantage: Building an Agency That Outlasts Every Platform
In this episode of The Orita Podcast, Aaron Schwartz sits down with Roman Yoffe, Founder & CEO of Absolute Web, for a candid, unfiltered conversation about what it really takes to build and scale a long-lasting ecommerce agency, from the early days of Yellow Pages to powering modern Shopify brands.Roman’s journey started as a 19-year-old immigrant with no roadmap, no experience, and no backup plan, just curiosity, grit, and a willingness to learn the hard way. Decades later, Absolute Web has become one of the most respected technical agencies in ecommerce, known for deep engineering expertise, long-term client relationships, and a strong internal culture that actually translates into better work.Together, they dive into:• From Soviet Union to startup: how Roman built Absolute Web from scratch• Why starting with “A” in the Yellow Pages was his first growth hack• The painful Magento era and why those scars became a competitive advantage• Why Shopify felt like a breath of fresh air and what it changed• The real edge of great agencies: engineering depth, not just design or strategy• Hiring philosophy: why “kind people” outperform everything else long-term• The hidden truth about agency-client relationships: alignment vs execution• Why some brands fail to get value... even with great partners• Building Triple Whale… no wait, Triple E: a brand-first, no-BS ecommerce event• How to create real community in an industry full of transactional networking• AI in ecommerce: hype vs reality and why humility still matters most• Roman’s core principle: “Promise less. Deliver more.”• The surprisingly honest coping mechanism behind agency stress (hint: cookies)This episode is equal parts operator wisdom, agency reality, and founder mindset. If you’re working with agencies, running one, or trying to build something that actually lasts in ecommerce, this conversation will hit.👥 Meet the guestRoman Yoffe, Founder & CEO at Absolute Web🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters[00:00] From Soviet Roots to Shopify Powerhouse: Roman Yoffe’s Origin Story[04:28] From “Anything for Anyone” to E-commerce Specialists: The Absolute Web Pivot[08:50] Why Kind Teams Win (and Scale Better Than Cutthroat Ones)[12:51] The Real Reason Agency-Client Relationships Break (Hint: It’s Not Execution)[17:03] AI, Hype, and Reality: What Actually Matters Right Now[21:02] Inside Great Partnerships: Alignment, Expectations, and What Brands Get Wrong🌐 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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75
Uncorking Real Retention: A CRM playbook from Sephora to the Wine Biz
In this episode of The Orita Podcast, Aaron Schwartz sits down with Amy Carr, Co-Founder of Wine by hOurs. Amy is a former CMO & CDO at ThirdLove, ex-Sephora and Gap Inc. who blends operator experience, financial discipline, and a deeply human approach to building brands.Amy’s career isn’t a ladder, it’s “a jungle gym across multiple playgrounds,” spanning finance, ecommerce, CRM, and brand-building at some of the most iconic companies in retail. That perspective leads to a clear point of view: great marketing isn’t just creative, it’s accountable, measurable, and rooted in understanding both the customer and the P&L.Together, they dive into:• Why a financial background can make you a better marketer and why most overlook it• The balance between creativity and profitability in modern marketing• Why “sometimes you need to slow down to speed up” and the power of career resets• How to actually do customer discovery: journey mapping, segmentation, and clarity of message• The three pillars of marketing budgets: brand, performance, and retention and why they rarely align• Why retention is getting harder and why performance dollars are creeping into it• The real role of loyalty: not just rewards, but data, community, and identity• Why most brands overcomplicate their tech stacks and how to keep it simple• AI’s real impact: better analytics, faster creative, and a massive unlock for mid-market brands• Why authentic, human creative will become more valuable (not less) in an AI world• The shift from SEO to AEO (agent engine optimization) and what it means for discovery• How ecommerce is changing: fewer websites, more aggregators, and AI-driven shopping journeys• Why the next generation of marketers must be AI-native and what that means for hiringThis episode is part operator playbook, part career philosophy, and part look into the future of commerce. If you’re building a brand, leading a team, or trying to make sense of how marketing is evolving in the age of AI, Amy brings clarity, honesty, and real-world experience.👥 Meet the guestAmy Carr, Founder of Wine by hOurs🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters[00:00] From Accountant to CMO: Amy Carr’s Unconventional Career Path[03:32] Why Great Marketers Think Like CFOs (and Most Don’t)[06:19] “Slow Down to Speed Up”: The Career Move Nobody Talks About[09:11] The Real Fight: Performance vs. Retention (and Who Wins)[12:07] How Top Brands Actually Understand Customers (Not Guess)[15:16] The Truth About Marketing Budgets: Brand vs. Performance vs. Reality[18:24] Why Cutting Brand Spend Will Haunt You Later[19:58] Loyalty Isn’t Dead—You’re Just Doing It Wrong[22:58] Your Tech Stack Is Probably Overbuilt (Here’s the Fix)[26:07] AI Is Changing Marketing Fast—But Not How You Think[28:54] The Death of Traditional Ecommerce (What Replaces It)[31:56] Amy’s Hard-Won Advice: Build a Career That Actually Matters🌐 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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74
Electric Eye on Shopify: Systems, Conversion, and What Comes Next
In this episode of The Orita Podcast, Aaron Schwartz sits down with Chase Clymer, Co-Founder of Electric Eye and host of Honest Ecommerce, to break down a truth most brands ignore: optimization isn’t about pretty pages, it’s about getting closer to the money.Chase didn’t start in ecommerce with some grand strategy. From touring in a pop-punk band to hacking together early Shopify projects, his journey into building one of the most respected optimization-focused agencies came from doing the work, breaking things, and learning what actually drives revenue.Over time, Electric Eye evolved from a full-service agency into something much sharper: an optimization machine focused on helping brands turn traffic into more revenue, not just better-looking websites.Together, they dive into:• Why optimizing your homepage is usually a waste of time and where to start instead• The real CRO mindset: eliminate fear, uncertainty, and doubt at every step of the journey• Why most brands know they should test… but never actually do it• How to use customer data (surveys, heatmaps, support tickets) to generate winning ideas• The difference between optimizing for conversion rate vs. optimizing for revenue per session• Why subscriptions aren’t always the answer and how memberships are quietly winning instead• The hidden bottleneck: founders drowning in tasks instead of focusing on experimentation• Shopify migrations: what goes wrong, what matters, and why most brands underestimate the complexity• AI, AEO, and SEO: what’s changing and what still matters• The biggest mistake brands make: solving for “busy work” instead of solving for customersThis episode is a masterclass in cutting through ecommerce noise and focusing on what actually drives growth. If you’re spending time debating homepage tweaks instead of fixing checkout, PDPs, or customer friction, this one will hit.👥 Meet the guestChase Clymer, Co-Founder at Electric Eye & Host of Honest Ecommerce🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters[00:00] From Pop Punk to Ecommerce: Chase Clymer’s Unlikely Path[03:28] Why Electric Eye Killed Services to Focus on One Thing: Optimization[06:17] The Truth About Shopify Migrations and Why Most Go Wrong[09:29] The Hidden Landmines That Break Ecommerce Replatforms[12:16] The Only Tech Stack That Actually Matters and What to Skip[15:29] Stop Guessing: How Smart Brands Actually Optimize for Revenue[18:28] Why Most Brands Don’t Test and How It’s Costing Them Millions[24:39] Forget the Homepage: Optimize Checkout First[32:09] The Perfect PDP: What Makes People Actually Buy[37:23] Shopper Behavior Is Changing Fast, Most Brands Aren’t Ready[42:14] Subscription Fatigue Is Real, What Works Now Instead🌐 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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73
Stop Emailing the Wrong People: Building Orita’s Intent Engine
In this episode of The Orita Podcast, Aaron Schwartz sits down with Daniel Brady, Co-Founder & Co-CEO of Orita.ai, for a rare inside look at how a neuroscientist accidentally became a startup operator and why the future of marketing belongs to teams who understand data, not just dashboards.Daniel didn’t set out to build in ecommerce. He started in neurobiology at Harvard, studying how the brain works, before realizing academia was too slow and startups were where real-time learning happens. That shift led to a core thesis: machine learning shouldn’t support the product, it should be the product.What followed was a journey from consulting to productizing one of the most counterintuitive ideas in marketing: sending fewer emails can actually make you more money.Together, they dive into:• From neuroscience to startups: why Daniel left academia to build faster, real-world systems• The founding insight behind Orita: machine learning as the product, not a feature• The “product-market fit pull” moment that changed everything overnight• Why most brands are solving the wrong problem and optimizing the wrong metrics• The hidden truth about email: more sends ≠ more revenue• Deliverability, demystified: what’s really happening behind the inbox• Why clicks (not opens) are the only metric that truly matters• The real role of machine learning: handling customer variability, not just scale• Why CDPs fail without the right team and how data becomes useless without action• The difference between AI vs. ML and why most “AI” tools can’t actually solve targeting• Bots, list decay, and the invisible forces quietly killing your performance• Why most marketing strategies are just “last month + last year” and how to break that cycle• The shift from static segments to predictive systems that adapt in real time• What changes as inboxes evolve with AI and why relevance will matter more than everThis episode is equal parts origin story, operator playbook, and technical breakdown. If you’ve ever wondered how modern brands should actually use data, what machine learning is really good for, or why your email strategy might be holding you back, this one will change how you think.👥 Meet the guestDaniel Brady, Co-Founder & Co-CEO at Orita.ai🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters[00:00] From Neuroscience to Startups...By Accident[02:07] Leaving Academia: Why Speed Won[03:25] Stumbling Into Startups and Getting Hooked[04:25] The Original Vision: ML as the Product[06:39] Why They Chose Commerce, Not Healthcare[08:01] The “Aha” Moment: Solving Marketing Waste[10:04] The First Product: Send Less, Make More[12:12] Finding Product-Market Fit...Fast[15:46] When Machine Learning Actually Matters for Brands[20:43] AI vs ML: What’s Real vs Hype[31:35] Convincing Brands to Email Fewer People[46:17] The Future: AI, Inboxes, and Changing Signals🌐 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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72
From Checkout to Doorstep: Marketing ShipBob’s Fulfillment Engine
In this episode of The Orita Podcast, Aaron Schwartz sits down with Casey Armstrong, CMO at ShipBob, for a deep dive into one of the most overlooked but mission-critical parts of ecommerce: fulfillment, logistics, and the systems that quietly determine whether a brand actually works.Casey brings a rare perspective, having operated on both sides of the table: helping scale a high-AOV DTC brand and now leading marketing and partnerships at one of the largest global 3PL platforms. His view is simple: fulfillment isn’t a back-office function. It’s a core growth lever, and a breaking point for most brands.Together, they discuss:• Casey’s path from running a luxury watch brand to leading growth at ShipBob• Why fulfillment is not a “nice to have”… it’s the business itself• The hidden mistakes brands make when they try to handle logistics too long• Why “we don’t need to be your first partner, we want to be your last” is the real goal• How customer feedback directly shaped ShipBob’s biggest product bets like global expansion and WMS• The rise of hybrid fulfillment: brands owning part of the stack while outsourcing the rest• Why most founders should not treat logistics as their differentiator• The reality of modern ecommerce: tariffs, carrier chaos, and constant macro shocks• How infrastructure, not tactics, is what actually protects brands during volatility• AI in logistics: smarter inventory placement, better packaging decisions, and faster iteration• The biggest unlock right now: small teams scaling massive brands through leverage, not headcountThis episode is a must-listen for founders and operators who want to understand what really drives customer experience after the “buy” button, and why the brands that win aren’t just good at marketing, they’re operationally ruthless.👥 Meet the guestCasey Armstrong, CMO at ShipBob🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters[01:17] From Luxury Watches to Global Logistics: Casey’s Path[04:10] $6K Orders, Broken Fulfillment: The Hard Lessons[06:41] Why Customer Obsession Wins, Even in Logistics[10:19] When to Outsource Fulfillment, And When Not To[14:03] “Powered By” Explained: The Future of Fulfillment Infrastructure[15:35] How Casey Actually Understands the Product...Hint: Not from Slides[17:23] Partnerships Are the Real Growth Engine[19:11] Serving Everyone from Startups to Billion-Dollar Brands[20:08] Fulfillment Expectations Are Rising Fast (Here’s Why)[20:30] Tariffs, Chaos, and Survival: What Brands Are Facing Now[24:30] Cash Flow Is Back (And It’s Everything)[27:43] Building a Fulfillment System That Doesn’t Break[29:33] Why Educating the Market Is Half the Battle[32:35] AI Is Quietly Rewriting Fulfillment[36:57] Build Faster or Die: The New Product Playbook🌐 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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71
Revenue Rocket Science: Retention Systems from Klaviyo to Shopify
In this episode of The Orita Podcast, Aaron Schwartz sits down with Zak Cassady-Dorion, Founder & CEO of ECD Digital, to talk about what it really takes to drive revenue in modern ecommerce and why most brands are still leaving money on the table.Zak’s path to building a 30+ person agency wasn’t traditional: from running a mountain bike tour company in Costa Rica, to sailing across the ocean, to helping legalize equity crowdfunding in the U.S., to finally building one of the most performance-driven ecommerce agencies in the space. That journey shaped a simple but ruthless philosophy: if it doesn’t drive revenue, it doesn’t matter.Together, they dive into:• Why the only metric that matters is simple: “Are we making the client more money?”• The biggest mistake brands make: optimizing metrics that aren’t even real (hello, bot clicks)• How to audit a $10M+ brand and instantly find hidden revenue opportunities• Why most Klaviyo accounts are broken and where the fastest wins actually are• The overlooked growth channel: direct mail and how to make it measurable• Why segmentation is still the hardest (and most valuable) part of retention• The shift happening right now: execution is dying, strategy is the only moat• How AI is accelerating great operators and exposing weak ones• What’s changing in ecommerce workflows as tools get faster, cheaper, and easier• The real unlock: freeing teams from manual work so they can think strategically• Why “learning and testing everything” is now table stakes in marketingIf you’re running an ecommerce brand and feel like your marketing is busy but not actually moving revenue, this episode will force you to rethink how you prioritize, measure, and execute.👥 Meet the guestZak Cassady-Dorion, Founder & CEO at ECD Digital🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters[00:00] From Costa Rica Tours to Ecommerce Operator[03:29] How ECD Digital Was Actually Born and Why It Works[06:17] The Only Rule: Make Clients More Money[09:19] The Revenue Audit Playbook: Finding Hidden Millions[12:24] Why Klaviyo + Postpilot = Untapped Revenue[15:16] Direct Mail Is Back And Now It Prints Money[23:17] The Overlooked Retention Channel Nobody Uses Enough[24:19] Most Brands Track the Wrong Metrics (Here’s the Fix)[27:13] The Email Stack That Actually Drives Revenue[29:03] AI Isn’t a Tool Anymore, It’s Changing the Game[34:18] Execution Is Dead. Strategy Is the Moat[36:53] Why He Finally Started a Podcast (After Years of Waiting)[42:15] Building a New Ecommerce Brand from Scratch🌐 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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70
Thread Count: What Moves the Needle in DTC
In this episode of The Orita Podcast, Aaron Schwartz sits down with Taylor Holiday, Founder & CEO of Common Thread Collective, to talk about the hardest and most important shift in ecommerce right now: moving from chasing growth at all costs to engineering profitable, predictable outcomes.Taylor has spent 14+ years inside ecommerce, watching the industry swing from “spend more to grow” to “every dollar needs a return.” Now, through CTC, he’s helping brands rebuild their entire operating system, starting not with ads, but with finance, cash flow, and truth.Together, they dive into:• Why great marketing is built on financial planning (not the other way around)• The biggest mistake brands make: accepting unprofitable media as “normal”• Why most teams run on workflows (“send emails every Friday”) instead of outcomes• The real constraint: capital allocation and how to decide where your next dollar goes• Why attribution (especially in email) is still broken and inflates false confidence• Incentive design: how bad KPIs create bad behavior across entire teams• The shift from agency “execution” to owning the definition of success• Why most ecommerce brands don’t understand their own costs (and how that kills them)• The evolution of pricing: from % of spend to fixed fees to outcome-based models• AI’s real impact: turning “company as people” into “company as code”• Why the future operator is a “profit engineer” sitting on top of AI systems• The harsh truth: most brands don’t know what they actually want and it shows in their dataIf you’ve ever felt like your growth is disconnected from your P&L, your team is optimizing the wrong metrics, or your marketing is just “doing things” instead of driving outcomes, this episode will hit hard.👥 Meet the guestTaylor Holiday, Founder & CEO at Common Thread Collective🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters[00:00] Profit Engineering: Why “Growth at All Costs” Is Dead[02:10] The System That Turns Marketing Into Predictable Profit[05:13] Stop Guessing: How Real Brands Actually Use Data[08:15] The Hard Truth: Growth Requires Short-Term Pain[11:00] Turning Ideas Into Execution (Without Relying on People)[13:43] Clients Want the Wrong Metrics: Here’s the Problem[16:34] The Ecommerce Business Model Is Breaking (And Evolving)[19:17] Pay for Results or Don’t Pay at All?[23:27] Ecommerce Has a Data Problem No One Wants to Admit[25:27] Why Most Founders Make Bad Business Decisions[26:19] The Silent Killer: Losing Money on Media (And Calling It Growth)[29:36] Stop “Doing Tasks.” Start Driving Outcomes.[30:51] Email Metrics Are Lying to You[34:43] Your Incentives Are Broken (That’s Why Nothing Works)[39:05] Why the Real Opportunity Is Sub-$5M Brands[41:14] The Amazon Playbook: Win by Giving Away Value[45:32] The Only Metrics That Matter (And Why You’re Using the Wrong Ones)🌐 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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69
Brief Encounters: Tommy John x Rivo on CX-Led Retention
In this episode of The Orita Podcast, Aaron Schwartz sits down with Max Wallace (Senior Director of Customer Experience at Tommy John) and Jamie Smith (Account Executive at Rivo) to unpack a side of ecommerce most brands say they care about but rarely prioritize… retention.Max has spent over a decade building CX at Tommy John, helping scale the brand from early startup days to a category leader. Jamie has lived every side of the ecosystem, from brand builder to retention tech operator. Together, they share a candid, operator-level view on what it really takes to create experiences customers come back for and tell their friends about.They dive into:• Why “everyone focuses on acquisition, but no one focuses on retention”• How great customer experience quietly becomes your most powerful (and free) acquisition channel• The reality of CX at scale: a small in-house team, a trusted BPO, and staying obsessively close to the front lines• Turning a “mountain of feedback” into actual product, policy, and experience improvements• Why empowering support teams (not scripting them) leads to better outcomes and higher retention• The fine line between policy and empathy and why “don’t split hairs” is often the right call• Loyalty programs: why they fail, when they actually make sense, and what’s changed• The smartest referral strategy most brands aren’t using: turning customers into affiliates• Building a modern retention stack: loyalty, referrals, accounts, and personalization working together• AI in practice: from speeding up product development to making sense of overwhelming customer data• The shift toward segmentation and truly individualized customer journeys (because there is no “average customer”)From CX philosophy and team design to loyalty strategy, referrals, and AI, this episode is packed with practical insights for operators trying to build brands that don’t just acquire customers, but keep them.👥 Meet the guestsMax Wallace, Senior Director of Customer Experience at Tommy JohnJamie Smith, Account Executive at Rivo🎙️ Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters[00:00] Meet the Operators Behind CX, Retention, and Brand Growth[05:33] How Max Helped Scale Tommy John’s Customer Experience for 12 Years[11:11] Jamie’s Wild Path: Mechanic to Coffee to Fashion to Ecommerce[16:26] Why Most Brands Get Customer Experience Completely Wrong[22:03] Retention vs Acquisition: Why Loyalty Programs Usually Fail[26:21] Cut the Noise: Simplifying Your Brand Strategy to What Actually Works[27:20] The Referral Flywheel: Turn Customers Into Your Best Growth Channel[28:41] Inside a Brand Operator’s Brain: How Tech Decisions Actually Get Made[31:45] The Hidden Profit Killer: Returns Fraud and What to Do About It[36:20] Building a Brand That Lasts 100 Years, not Just the Next Quarter[38:38] From Data Chaos to Clarity: Making CX Insights Actually Actionable[40:28] AI Is Rewriting Ecommerce (Faster Than Most Brands Realize)[43:55] Final Takeaways: Retention, Empathy, and Playing the Long Game🌐 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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68
Deploy the Agents: AI agents for Omnichannel Retention
In this episode of The Orita Podcast, Aaron Schwartz sits down with Stephen Campbell, Co-Founder & CEO of Revamp AI, to talk about what happens to marketing, software, and entire industries when AI stops being a tool and starts being the system.Stephen has been building in AI since he was 14, from self-driving go-karts to YC-backed startups. Now, through Revamp and the AI Collective, he’s operating at the intersection of technology, community, and a fast-changing economic reality where data is the moat, SaaS is under pressure, and agents are replacing workflows.Together, they dive into:• Why “data is the new moat” and what that means for brands today• The shift from SaaS tools to self-improving AI agents and who wins• How Revamp uses agents to power true 1:1 lifecycle marketing at scale• Why generic AI outputs fail and why brand-specific data changes everything• The rise of “vibe coding” and what happens when non-technical teams build their own tools• How lifecycle marketing became the best training ground for AI systems• The real unlock: more “at-bats” vs. better conversion and why you need both• Why pricing in AI is still broken and where it might go next• What brand operators should actually do with AI right now, not theory, real workflows• The bigger picture: how AI could reshape institutions, careers, and economic systemsIf you’re trying to figure out where AI fits in your business, or what happens when it rewrites the rules entirely, this episode will push your thinking forward.👥 Meet the guestStephen Campbell, Co-Founder & CEO at Revamp & Founder of the AI Collective🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters[00:00] Meet Stephen Campbell: Building at the Edge of AI[01:24] From Self-Driving Go-Karts to AI Founder[02:35] Early Hustles: Tech, Startups, and Finding the Path[03:29] Why He Left Entrepreneurship...and Came Back Stronger[04:45] Inside Revamp + The AI Collective Origin Story[05:15] The AI Collective: 250K Members and Growing Fast[08:02] The Big Idea Behind Revamp[08:59] What “AI Agents” Actually Mean, Not the Buzzword Version[10:04] The Real Problems Agents Are Solving Right Now[11:54] Why Revamp Works When Generic AI Doesn’t[13:31] Self-Improving Systems: The Future of Marketing[13:56] Data Is the Moat: What Most Brands Miss[16:04] Turning AI Into Leverage for Your Team[17:42] The Tradeoff: More Revenue vs. Better Experience[20:03] Founder Reality: Cycles, Hype, and What’s Actually Changing[22:12] Pricing Is Broken: What Comes After SaaS[25:23] The Only AI Advice Brand Operators Need Right Now[26:30] Where to Find Stephen, and Why You Should🌐 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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67
SuperAngel Signals: Picking Commerce Winners Before the Crowd
In this episode of The Orita Podcast, Aaron Schwartz sits down with Ben Zises, Founder and GP of SuperAngel.Fund, to unpack what it really takes to win in modern commerce from the earliest angel check to building billion-dollar brands.Ben shares how he went from hustling DJ gigs and running a water cooler business in college to becoming one of the most active and respected early-stage investors in consumer and commerce tech. He breaks down his investing philosophy, why he bets on founders over everything else, and how he built a flywheel between brands and software that gives him a unique edge in the ecosystem.Together, they dive into:• Why Ben tries to “write the first check” and what he looks for before there’s product or traction• The real strategy behind investing: singles, doubles, and letting home runs take care of themselves• Why the best founders often have a trail of failures and why that’s a positive signal• The power of investing in both brands and commerce tech (and how it creates a flywheel)• What actually makes a brand venture-backable today: IP + distribution or nothing• Why operational excellence, not just marketing, is the real differentiator now• The underrated skill that filters 90% of deals: clear, concise communication• How AI is reshaping teams, headcount, and what “efficient” looks like for brands• Why optimizing for LLM discovery (not just Google) is the next big unlock👥 Meet the guestBen Zises, Founder & GP at SuperAngel.Fund🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters[00:00] Meet Ben Zises: The Investor Behind the Brands[01:09] Hustling Early: DJ Gigs, Side Businesses, and Making Money Young[02:32] The First Startup: Real Estate Pain to PropTech Bet[04:42] The $10K Bet That Started It All (Quip)[08:22] Inside Ben’s Playbook: How He Actually Invests[09:29] The Real Job: Air Traffic Control for Founders[11:05] 50 Angel Checks Later… What Works (and What Doesn’t)[12:32] How to Spot a Brand That Can 10x (or 100x)[13:58] The Commerce Flywheel: Why Brands + Tech Win Together[17:35] The New Bar: What Makes a Brand Investable Today[21:40] Distribution or Die: The Real Differentiator[24:10] Why Most Pitch Decks Fail in 30 Seconds[25:05] AI Is Rewriting Commerce: Here’s What Matters[27:40] How to Reach Ben (and Why You Should)🌐 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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66
Treats, Tech, and Tactics: CRM Lessons from BARK
In this episode of The Orita Podcast, Aaron Schwartz sits down with Ivory Razor, Director of CRM at BARK, for a deep dive into what modern retention really looks like when you stop thinking in channels and start thinking in systems.Ivory has built across fashion, subscription, ecommerce, marketplace, and now pet, with stops at Calvin Klein, Dressbarn, Gwynnie Bee, littleBits, Scentbird, Resident, Angie, and BARK. That range gives her a rare perspective: great CRM isn’t just about email or SMS. It’s about understanding the full customer journey, the data behind it, and the business case for every move you make.Together, they discuss:• Ivory’s path from fashion marketing into CRM, and how curiosity shaped every career move• What she learned moving across DTC, subscription, ecommerce, marketplace, and consumer brands• Why the best retention leaders think about the full system, not just one campaign• The “Infinity Stones” of CRM: project management, creativity, analytics, and cross-functional fluency• Why data literacy is a true superpower for retention marketers and how it changes your influence across the org• How to think about acquisition and retention together so you’re not just filling a leaky bucket• The danger of over-segmentation vs. sending in broad slabs and how to find the middle ground• How to prioritize CRM work using impact, confidence, and efficiency instead of opinions• What platform choice really means across Iterable, Klaviyo, Attentive, and Postscript• Where AI can actually help CRM teams today, and why RCS could become a meaningful new channel for the right brandsThis one is packed with practical frameworks for CRM leaders, retention marketers, and operators trying to drive real business outcomes, not just campaign metrics. If you want a smarter way to think about retention, Ivory brings the playbook.👥 Meet the guestIvory Razor, CRM leader at BARK🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters[09:59] Retention Isn’t a Channel Problem. It’s a Systems Problem[16:51] The Smartest Retention Teams Know Why Customers Show Up[22:36] How Great CRM Leaders Handle Pressure From Every Side[23:03] Why Data Is the Real Superpower in Retention[26:17] The Retention Playbook: What Actually Moves the Needle[27:01] The Biggest Retention Mistakes Brands Still Make[31:04] Easy CRM Wins: How to Reuse What Already Works[33:44] Which AI Tools Are Worth It for CRM Teams?[39:20] RCS Is Coming Fast. Here’s Why It Matters🌐 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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65
Bad Content Is a Tax: Shopify, Operators, and AI-era Growth
In this episode of The Orita Podcast, Aaron Schwartz sits down with Aaron Orendorff, Chief Content Officer at The Operators Network, for a conversation about what great content still requires in the age of AI: judgment, taste, reps, and a point of view.Aaron has spent more than a decade writing, editing, and shaping ecommerce content at the highest level, from Shopify Plus to Common Thread Collective to one of the most influential operator communities in the space today. And his perspective is clear: AI can make content faster, but it cannot make weak thinking strong.Together, they discuss:• Aaron’s path from freelance writer to one of ecommerce’s sharpest content minds• How he broke into major publications by studying what was already working and adding a real point of view• Why the best content is original, useful, and backed up• The real content playbook: create one great thing, then repurpose it relentlessly• Why people don’t remember your posts nearly as much as you think they do• AI as multiplier, not magic and why bad inputs still produce bad content, just faster• Why taste, discernment, and subject matter depth matter more now, not less• How to use Claude projects, content libraries, and persona-based prompts without losing authenticity• Why short-form video and carousels are the next frontier even for B2B brands• The biggest content lesson of all: the worst-performing content is the content you never publishThis one is packed with practical advice for founders, marketers, and operators trying to stand out without drowning in content noise. If you care about content that earns attention and compounds over time, Aaron gives a real playbook for how to do it.👥 Meet the guestAaron Orendorff, Chief Content Officer at The Operators Network🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters[08:27] What Separates Great Content From Generic Noise[11:04] Why the Best Content Operators Build Networks, Not Audiences[14:02] The 3 Ingredients of Great Content: Original, Useful, Proven[16:31] Create Once, Distribute Ruthlessly[19:35] Why Editorial Pressure Kills Good Content[22:08] How to Refresh Old Content Without Reinventing It[24:54] The Best Content Starts With One Question: What Do People Want?[27:58] Why Engagement Is the Best Content Brief[29:27] The Tools Aaron Uses to Spot Content Winners[30:15] AI Won’t Save Bad Content, It Just Scales It[31:23] How to Build Taste, Judgment, and a Real Point of View[32:43] How to Use AI Without Losing Authenticity[35:01] Why Short-Form Video Is the Next Big Content Unlock[37:46] Sales First, Marketing Second: The B2B Content Reality[42:57] The Career Bet That Changed Everything🌐 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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64
One Site Per Customer: Marko Bon on Domaine’s Experience-First Shopify Scale Machine
In this episode of The Orita Podcast, Aaron Schwartz sits down with Marko Bon, President & Co-Founder of Domaine, for a wide-ranging conversation about what it takes to build modern commerce experiences at enterprise depth, without losing speed, clarity, or common sense.Marko spent nearly two decades on the brand side before launching a Shopify agency in 2018 with a simple but powerful thesis: bring enterprise rigor, documentation, and operational discipline into an ecosystem that was still early, fast, and wildly underbuilt for complex brands. That thesis became Domaine.Together, they discuss:• Marko’s path from creative to ecommerce operator, with stops at Ralph Lauren, Brooks Brothers, Theory, and The Line• Why Salesforce Commerce Cloud lost momentum, and why Shopify became the obvious next move• What it looked like to bring true enterprise process and complexity into the Shopify ecosystem early• How Tomorrow and Half Helix merged to form Domaine, and what it really takes to merge teams, cultures, and operating models• Why cross-functional collaboration is still a major competitive advantage for modern brands• The case for shared KPIs, customer-centric teams, and treating partners as real growth levers• Why Shopify may be moving faster than anyone can comfortably keep up with and why that’s still the better side to be on• AI in commerce: what’s real, what’s noise, and how agencies can help brands separate signal from hype• The rise of ACO, GEO, and AI-driven discovery, and why brands need to start thinking about owning the customer relationship inside emerging AI channels• Why most brands shouldn’t try to become technology companies, and how to stay focused on what actually differentiates the brandThis one is full of operator wisdom, strategic nuance, and deeply earned perspective from someone who has been on both sides of the table. If you’re building, migrating, or scaling a Shopify brand and trying to stay grounded while the entire commerce stack keeps shifting, this conversation will give you a lot to think about.👥 Meet the guestMarko Bon, President & Co-Founder at Domaine🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters[03:28] What It Really Takes to Merge Two Agencies[08:03] Shopify Is Moving Fast, Can Brands Keep Up?[12:05] ACO, UCP, and the New Rules of Discoverability[16:35] AI in Ecommerce: What’s Real and What’s Just Noise[21:24] Why Gemini Might Matter More Than Brands Realize[22:37] Inside Domaine’s AI Commerce Playbook[25:36] How Smart Brands Cut Through the AI Tool Chaos[28:17] Why a Designer’s Mindset Still Wins in Commerce[31:08] The Playbook for Scaling Modern Brands[37:04] Why the Best Brands Treat Partnerships Like Growth Engines🌐 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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63
The Partnership Era: Building Strategic Alliances That Unlock Growth Worldwide
In this episode of The Orita Podcast, Aaron Schwartz sits down with Sara Pereda, Global Head of Partnerships at Rivo, for a candid conversation about what great partnerships look like when budgets are tighter, expectations are higher, and “good vibes” alone don’t move revenue.Sara’s background is anything but typical: entertainment, nonprofit, finance, HR, agency, SaaS. But that unusual path made her exceptional at one thing modern commerce desperately needs: building systems, relationships, and communities that scale.Together, they unpack:• Sara’s unconventional path from entertainment and finance into ecommerce partnerships• The through-lines that made her effective across every role: organization, communication, and seeing the bigger picture• Why the best partnerships are always a two-way street and why “checking the box” kills value• The real goal of partnerships: revenue first, relationship through value• Sara’s rule of the Three I’s: introduction, information, invitation• Why partner people need to stop obsessing over logos and start creating measurable outcomes• How Smarter Ships grew into one of ecommerce’s most trusted communities• The tools she uses to scale, from PRMs to Crossbeam to AI-powered workflows• Why the old partnership playbook is breaking and what operators need to do differently nowThis one is packed with hard-won lessons for anyone building in ecommerce, especially if you work in partnerships, SaaS, agency growth, or ecosystem strategy. Sara doesn’t just talk about community and value. She’s built both.👥 Meet the guestSara Pereda, Global Head of Partnerships at Rivo | Founder of Smarterships🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters[00:00] What Great Partnership Operators Do Differently[05:25] Why One-Way Partnerships Always Break[08:03] Partnerships That Don’t Drive Revenue Aren’t Partnerships[10:49] The Tool Stack Sara Uses to Scale Partnerships[13:55] How Smarter Ships Became Ecommerce’s Most Trusted Community[19:40] What’s Next for Smarter Ships[25:36] Why the Best Networkers Always Win[27:15] Not Every Partner Deserves the Same Playbook[30:07] How to Build a Partnership Function From Scratch[33:03] The Systems Behind High-Performing Partnerships[34:09] Why Rivo Is Shopify’s Best-Kept Secret[38:47] How Sara Enables Partners Without Wasting Their Time[43:06] The Old Partnerships Playbook Is Dead🌐 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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62
Family Threads: How The Normal Brand Blends Legacy, Loyalty, and Leading-Edge Tech
In this episode of The Orita Podcast, Aaron Schwartz sits down with Jimmy Sansone and Conrad Sansone, co-owners of The Normal Brand, to unpack how a personal product need turned into a real omnichannel apparel business built the old-school way: action first, learn fast, and stay obsessive about contribution margin.They break down:• Growing up as two of ten kids and why a “team mindset” shaped how they lead• The early days shipping orders from a basement and learning the hard parts (tech packs, MOQs, wholesale) the messy way• Why they went omnichannel by necessity: wholesale first, retail later, ecommerce always• How they think about stores: human experience, brand immersion, and the details you can’t replicate online• The lens they use to vet new tech: incrementality, contribution margin, and partners who speak their language• What they’re focused on now: first-to-second purchase velocity, flow optimization, and creative that moves across Meta, PDPs, and CRM• Why they’re bullish on “software-enabled agencies” that blend outcomes, tooling, and real operator supportThis one is packed with founder honesty, tactical lessons, and a refreshingly grounded view on scaling without chasing hype.👥 Meet the guestsJimmy Sansone: Co-Owner at The Normal BrandConrad Sansone: Co-Owner at The Normal Brand🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO, Orita.ai🎧 Chapters[00:00] Meet The Normal Brand: Brothers, Builders, Operators[02:00] Raised Entrepreneurial: 10 Kids, One Team Mentality[05:33] Basement-to-Brand: The Messy Mistakes That Made Them Better[10:44] How Two Brothers Split Leadership Without Stepping On Toes[12:38] Omnichannel on Purpose: Retail + Wholesale + DTC, Done Right[20:44] Wholesale as a Growth Engine: Retailers as Partners, Not Channels[22:11] Why They Send Less Email and Make More Money[26:42] From First Buy to Repeat: The 60-Day Retention Playbook[36:00] What They’re Building Next: New Product, Bigger Bets, Same Discipline🌐 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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61
Designing E-Commerce Success: John Surdakowski's Journey from Freelancer to Founder
In this episode of The Orita Podcast, Aaron Schwartz sits down with John Surdakowski, Founder & CEO of Avex, to talk about what happens after a brand “wins” acquisition, then realizes the site, stack, and customer journey aren’t built to sustain the next stage.John built Avex into one of the most trusted Shopify agencies for mid-market and enterprise brands, and he has a rare ability to cut through ecommerce noise.Together, they discuss:• Why most fast-growing brands hit $50–100M on duct tape (and what breaks next)• Stabilization before optimization: fixing the tech stack so teams can move again• Testing culture as a growth engine: roadmaps, hypotheses, and why losing tests still win• Omnichannel reality: when Shopify becomes the hub for DTC + B2B + retail• AI in ecommerce: where it’s already making teams faster (and where it’s still just noise)• Agentic commerce + AI discovery: what to watch, and what not to obsess over yet• The headless lesson: why 99% of brands shouldn’t over-engineer their way into painIf you’re scaling a Shopify brand and feeling the gap between “we’re growing” and “we’re set up to keep growing,” this one is for you.👥 Meet the guestJohn Surdakowski, Founder & CEO, Avex🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO, Orita.ai🎧 Chapters[00:00] Who Avex Is Built For (and Why “Mid-Market” Isn’t a Revenue Number)[04:02] What Great Agencies Do Not Do (and How Partnerships Should Work)[06:50] Redesigns Don’t Fail Because of Design, They Fail Without Exec Buy-In[09:30] Unified Commerce Isn’t a Buzzword, It’s the Only Way Retail Scales[12:14] Shopify Drops 50 New Things a Year: Here’s How to Tell What Matters[15:04] AI Didn’t Change the Goal, It Changed the Speed (and the Bar)[17:44] The Brands That Win Don’t Guess, They Test (Relentlessly)[20:46] CRO Tool Stack: What’s Worth Using to Test, Personalize, and Learn[23:25] All-in-One vs Best-in-Class: The Real Reason Brands Consolidate[26:07] $100M Brand Problem: When Your Site Is Held Together With Duct Tape[29:00] Retention Isn’t Email, It’s the Whole Post-Purchase Relationship[31:27] Agentic Commerce: Are We Building for Humans… or Bots?[34:08] Don’t Turn Your Brand Into a Tech Company (Learn From Headless)🌐 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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60
Inbox Alchemy: Turning EMEA Email Programs into Predictable Revenue
In this episode of The Orita Podcast, Aaron Schwartz sits down with Daniel Höhnke, General Manager of EMEA at Andzen, for a candid conversation about what it really takes to scale ecommerce across borders.From launching one of Germany’s earliest online furniture experiments to leading CRM strategy across global brands, Daniel shares what he’s learned moving from merchant to agency life and why international growth is far more nuanced than most U.S. brands expect.Together, they unpack:• Why Germany, France, Spain, and the UK behave like completely different markets, not one region• The biggest mistake U.S. brands make when expanding to Europe (hint: English isn’t enough)• How GDPR changed the game and why it’s no longer the real barrier• Why personalization maturity in the UK still outpaces much of mainland Europe• The hidden complexity of Shopify Markets + Klaviyo in multi-country setups (and what finally got easier)• What an “AI-first” CRM agency really looks like internally and how that mindset compounds client results• How empathy, segmentation, and regional nuance unlock real growth across EMEAThis episode is a masterclass in international expansion, CRM strategy, and why deep customer understanding still beats tool obsession.If you’re a U.S. brand eyeing Europe, or a European brand scaling globally, this one will sharpen your thinking fast.👥 Meet the guestDaniel Höhnke, GM EMEA at Andzen🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters[00:00] Meet Daniel Höhnke: From Magento 0.6 to Global CRM Leader[02:34] Why I Left the Brand Side for Agency Life (No Regrets)[04:59] The German Ecommerce Bubble and Why It Stayed Closed[07:37] AI-First Ecommerce: What That Actually Means in 2026[10:11] Martech Overload: How Brands Choose the Wrong Tools[12:47] Europe Is Not a Market (And That’s Your Advantage)[15:25] US Brands Expanding to Europe: Do This First[17:41] GDPR Panic vs. Reality: What Actually Matters Now[20:29] The International Playbook: Scaling Smart Across EMEA🌐 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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59
Beyond CRO: The Growth Experiment Mindset
In this episode of The Orita Podcast, Aaron Schwartz sits down with Drew Marconi, Co-Founder & CEO of Intelligems, to talk about the most under-discussed lever in ecommerce: how you price, promote, and merchandise profit on purpose, not by vibes.Drew built dynamic pricing systems in ride share, then brought that same experimentation mindset to Shopify brands. The result: a platform (and a philosophy) that treats your storefront like a living sales machine and forces teams to stop making “local” decisions that quietly fight each other.Together, they dive into:• Why “the right price” isn’t a number, it’s a strategy that changes with timing and cohorts• How to test pricing without freaking out your customers (or your support team)• The hidden truth: your site has a dozen “pricing” levers beyond the product price• Why most brands test too small and how to build a roadmap that breaks real constraints• The segmentation starting point that matters most: new vs returning (then source)• Shipping thresholds, discounts, and offers: why you can’t optimize them in isolation• Personalization that rhymes: matching the promise in the email/ad to the on-site experience• How the best brands think in LTV first and won’t debate decisions without it• The role agencies play in making experimentation real (and scalable)• What’s next: APIs, MCP-style building blocks, and storefronts that get more dynamic fastIf you’ve ever watched your team argue over pricing, CRO, shipping, and promos like they’re separate worlds, then this one will make those dots connect.👥 Meet the guestDrew Marconi, Co-Founder & CEO at Intelligems🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters[00:00] From McKinsey to Ride Share to Shopify: Why Drew Built Intelligems[03:07] “Cost-Plus Is a Lie”: The New Rules of Pricing[07:43] Price Testing Without Starting a Customer Riot[09:58] Personalization That Pays (Not Just “Hi {FirstName}”)[13:09] Your Site Is Frankensteined: Making Offers, Shipping, and UX Work Together[14:58] Retention Math: Stop Optimizing Orders, Start Optimizing LTV[17:24] The Shift Back to Growth, But With Guardrails[19:57] CRO Isn’t Enough: Test the Business Model, Not Button Colors[22:54] The Only Segmentation Question That Matters First[25:56] Find Your “Money Segments” Before You Overcomplicate Everything[29:40] How to Build a Real Experimentation Culture (Without Getting Fired)[33:29] A Brand Went Full Mad Scientist and It Worked[36:58] Why Agencies Win: The Secret Growth Engine Behind the Best Tests[40:43] What Intelligems Is Building Next: Dynamic Storefronts + APIs + AI🌐 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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58
Entertain to Retain: Humor, AI & Customer Loyalty
In this episode of The Orita Podcast, Aaron Schwartz sits down with Zach Scheimer, Senior Retention Marketing Manager at Criquet Shirts, for a masterclass in modern retention, where data meets brand, and CRM is more than just sending emails.Zach’s path to retention isn’t typical. From NFL mascot to stand-up comic to deeply technical email architect, he brings a rare blend of analytics, humor, and systems thinking to the craft. And it shows.Together, they unpack:• From mascot to marketer, how an unconventional background shaped Zach’s retention mindset• Data over opinions, why “the numbers are telling you something” is his core philosophy• Beyond email, how retention now spans SMS, direct mail, onsite experience, loyalty, and returns• The micro vs. macro lens, why customer service and retention are solving the same problem• Creative as the overlap, how brand voice fuels both performance and retention• Loyalty & exclusivity, why your best customers want to feel “in the club”• AI on-site, how product comparison agents could reshape customer experience• SMS & RCS, why richer mobile messaging is the next unlock• The hidden risk of over sending, and how channel fatigue quietly kills long-term valueIf you care about customer lifetime value, cross-channel alignment, or building a retention engine that actually respects the customer, this one’s for you.👥 Meet the guestZach Scheimer, Senior Retention Marketing Manager at Criquet Shirts🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters[05:32] Retention’s Secret Weapon: Technical Skills Most Marketers Don’t Have[08:24] Why Your Emails “Underperform”[11:11] The Naming System That Turns Your CRM Into a Money Dashboard[14:00] How Criquet’s Brand Voice Makes Customers Feel Like Insiders[16:46] Personalization Without Being Creepy: The Line Every Brand Crosses[17:40] Retention Isn’t Email Anymore: The New Tool Stack (and New Rules)[20:29] Loyalty That Works: Exclusivity vs. Points[22:11] The Customer Journey Isn’t Linear: Here’s How Criquet Designs It[24:48] Performance vs. Retention Is a False War (Creative Is the Bridge)[27:42] Stop Retargeting Recent Buyers: The Simple Fix Most Brands Miss[30:41] Gmail AI Summaries + RCS: The Next Wave Coming for CRM[34:34] Marketing + CX: The Teams That Don’t Talk Are Bleeding Revenue[37:03] AI on Your Site: The Shopping Assistant That Could Replace “Where Do I Click?”🌐 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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57
Founders Who Deliver: The Package That Sparked a Unicorn
In this episode of The Orita Podcast, Aaron Schwartz talks to Itamar Zur, Co-Founder & CEO of Veho, to unpack why delivery isn’t just logistics: it’s brand, loyalty, and growth hiding in plain sight.Ita didn’t set out to build a logistics company. He set out to fix broken customer experiences. From bad doorstep deliveries to stolen packages, Veho was born from a simple obsession: make the post-purchase experience feel as intentional as the product itself. That obsession took Veho from an MBA idea to a nationwide network powering last-mile delivery for brands like Sephora and Lululemon.Together, they dive into:• Why customer experience, not speed alone, is the real last-mile advantage• How Veho scaled from zero to unicorn without copying UPS or FedEx• The co-founder breakup that almost killed the company and what saved it• Building culture and principles that scale past the founding team• Hiring mistakes, leadership evolution, and when to trust your gut• Why last-mile delivery directly impacts LTV, conversion, and repeat purchase• How AI is reshaping logistics, decision-making, and internal leverage• Veho’s vision to own the entire post-purchase journey, not just delivery👥 Meet the guestItamar Zur, Co-Founder & CEO at Veho🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters[00:00] From Lawyer to Logistics Founder[07:47] Zero to “This Might Work”: Building Veho from Nothing[10:39] Co-Founder Breakups, Hard Pivots, and Finding the Right Partner[13:31] Scaling Whiplash: How Leadership Has to Change[16:10] Hiring Without Regrets: The Rules (and Mistakes) That Matter[19:27] How You Build a Customer-Obsessed Company (on Purpose)[30:23] Why “If It’s Not Written, It’s Not Decided” Wins[32:39] AI as a Force Multiplier: Where It’s Already Paying Off[37:21] Culture That Scales: Principles Over Heroics[41:50] What Veho Borrowed (and Didn’t) from UPS, FedEx, Amazon, Uber[45:16] Delivery = Brand: The Hidden Driver of LTV[49:49] Beyond the Box: The Post-Purchase Platform Future🌐 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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56
Crossing Borders, Cracking Logistics: Inside the Shipping Wars
In this episode of The Orita Podcast, Aaron Schwartz sits down with Alex Yancher, Co-Founder & CEO of Passport, to go deep on the part of ecommerce most people underestimate until it breaks: international expansion.Alex has seen it all...investment banking during the financial crisis, early Facebook, building and selling companies, and then spending the last decade living in the messy reality of cross-border logistics. He shares what it really takes to help brands unlock global growth, why Passport leaned into M&A as a strategic weapon, and how the next wave of commerce will be defined by who can move fast across operations, regulation, and customer experience.Together, they dive into:• Alex’s path from Morgan Stanley to Facebook to entrepreneurship• The early “warehouse in Delaware” era that taught him cross-border the hard way• Why Passport made two key acquisitions and how to integrate without breaking the org• When brands should stay cross-border vs. go in-country with local inventory• The hidden complexity: importer of record, compliance, taxes, labeling, and marketplaces• Why TikTok Shop and marketplace rules are forcing new global playbooks• How Passport reduces “Where’s my package?” pain by owning the tracking and support layer• What AI is changing inside Passport from call recording culture to semantic search and analytics• Why international is a growth lever and a risk hedge for brands too dependent on the US👥 Meet the guestAlex Yancher, Co-Founder & CEO at Passport🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters[00:00] Meet Alex Yancher: The “Build + Buy” Playbook Behind Passport[05:40] From Wall Street to Startups: The Skills That Still Pay Off[09:54] Why Most Founders Ignore M&A (And Why Alex Didn’t)[15:32] How to Buy Companies Without Breaking Yours: Lessons From the Trenches[20:11] Going In-Country: The Hidden Mess Behind “Local Fulfillment”[25:33] When You Become the Buyer Everyone Calls: Passport’s M&A Flywheel[31:57] Why Brands Pick Passport: The Real Differentiator (It’s Not Just Shipping)[38:39] How Passport Uses AI: Internal Leverage, Faster Decisions, Better Ops[44:09] Scaling to 230 People: CEO Lessons, Bottlenecks, and Staying Aligned🌐 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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55
Killing the Popup: What 2,000+ Shopify Brands Taught Me About Conversion
In this episode of The Orita Podcast, Aaron Schwartz sits down with Shaan Arora, Co-Founder & CEO of Alia, to unpack how a scrappy team of college friends turned a simple idea, making ecommerce popups work better, into one of the fastest-growing tools in the Shopify ecosystem.Shaan shares why “ownership” has been his north star since day one, how the founding team built trust (and staying power) early, and the unconventional growth moves, building in public, betting on partners, and obsessing over support, that helped Alia scale to real momentum.Together, they dive into:• Why Shaan cared more about ownership than a traditional career path (and how his parents shaped that mindset)• How Alia’s founding team formed and the “hot dog stand” promise that kept them locked in through pivots• The real competitive edge: shameless scrappiness, relentless ops, and world-class technical execution• Shaan’s boldest sales story and why “doing the most” can win the deal• What Alia does differently: smarter timing, smarter testing, and popups personalized by shopper behavior• Why “data moat + speed” is the formula for beating incumbents• Building in public as a free growth channel and why revenue posts work (even when they feel weird)• The underrated growth lever: elite support + customer success as reputation engine• Shaan’s take on SaaS: beware companies that market harder than they build• Founder lessons on focus, letting fires burn, and not becoming the bottleneck as you scale👥 Meet the guestShaan Arora, Co-Founder & CEO at Alia🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters[00:00] Meet Shaan: From CS Kid to Shopify Power Player[02:47] Why Ownership Beat the “Safe Job” Path[05:32] Co-Founders: The Real Moat Nobody Talks About[08:24] How to Build a Team That Doesn’t Need Hand-Holding[10:52] “Be Shameless”: The Sales Moves That Close Deals[13:40] Hiring Filters That Save You From Bad Fits[16:19] The Startup Test: Are You Obsessed Enough?[19:10] What Alia Does (And Why Popups Are Still Underrated)[21:58] Popups, But Smarter: Timing, Targeting, and Auto A/B Tests[24:34] Building in Public: The Free Growth Channel That Works[27:21] Posting Revenue: Why It Converts (And When It Backfires)[30:04] Customer Success = The Flywheel (Not a Department)[32:38] SaaS Advice: Don’t Buy Hype, Buy Proof[35:25] Leadership Level-Up: Stop Being the Bottleneck🌐 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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54
Community Over Competition: Inside the $10B Disruptor Economy
In this episode of The Orita Podcast, Aaron Schwartz sits down with Max Starkman, Founder of DTConnect and Beanstalk co-founder, to talk about the commerce ecosystem from a perspective very few people have: agency roots, brand-side operator experience, and now a front-row seat to the best founders and executives in the space. Max shares how he (reluctantly) found his way back into commerce, what he learned helping build and support brands at scale, and why the next era of ecommerce belongs to the teams who can create trust, cut through noise, and build real relationships online and offline.Together, they dive into:• Growing up “born into” the Shopify world and trying to run away from it• What Max learned building with Agora Brands and working with elite operators• Why the best brands aren’t just good at marketing, they’re good at building trust• The origin story of Commerce Summit, Beanstalk, and why curation beats content overload• The idea behind DTConnect: fixing the broken “vendor ↔ brand” relationship• What’s changing in acquisition, retention, and community and where brands are finding leverage• The hidden superpower of great operators: speed, clarity, and ruthless focus• Why moving past transactional networking is the real unlock for the ecosystem👥 Meet the guestMax Starkman, Co-Founder at DTConnect & Beanstalk🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters[00:00] Meet Max: The Shopify Kid Who Tried to Escape Commerce[02:45] Agora Brands: The DTC Aggregator Play (Without the Financial Engineering)[05:39] What the Best Brands Have That Everyone Else Fakes[08:30] “Value First” Isn’t a Slogan, It’s a Growth Strategy[11:12] How Commerce Summit Became Beanstalk (and Why It Works)[14:12] DT Connect: Fixing the Broken Brand ↔ Tech Relationship[23:46] Why Focus Wins: One Clear Problem vs Ten Vague Features[26:43] Partnerships That Matter (and 95% That Don’t)[28:22] Events, Dinners, Experiments: Finding the Real ROI[38:31] CAC is Brutal: What Smart Brands Do When Ads Stop Printing Money[43:51] Brands Want SaaS. SaaS Wants Brands. Who’s Right?🌐 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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53
From Jets to Unicorns: The Architect Behind Billion-Dollar Brands
In this episode of The Orita Podcast, Aaron Schwartz sits down with Lolita Petrossov, Founder & CEO of Evestar, to unpack her rare journey from co-founding a high-profile private jet-share startup to building one of ecommerce’s most respected full-service agencies. Lolita shares how her experience scaling JetSmarter shaped her perspective on growth, marketing, and leadership and why she chose a quieter, more customer-obsessed path with Evestar. Along the way, they explore how ecommerce, agencies, and AI are evolving faster than ever.Together, they dive into:• Lolita’s path from professional tennis to tech founder to agency CEO• What she learned scaling JetSmarter and why she deliberately chose a different model next• How Evestar built a true full-service ecommerce offering as the industry exploded• Why content is the most important competitive advantage in modern DTC• How AI is reshaping creative, media buying, and agency operations• Evestar’s in-house AI product, and when services businesses should build software• What brands are underestimating about speed, focus, and execution today👥 Meet the guestLolita Petrossov, Founder & CEO at Evestar🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters[00:00] Meet Lolita: From Private Jets to Ecommerce Powerhouse[03:15] Why She Left JetSmarter to Build Evestar[10:23] How DTC Marketing Changed (and Why It’s Harder Now)[19:11] AI Is Rewriting Marketing Faster Than Anyone Expected[24:29] What Brands Need to Do Next + Where to Find Evestar🌐 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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52
Schlep Happens: How Hulken Rolled Its Way to 8-Figures
In this episode of The Orita Podcast, Aaron Schwartz sits down with Alex Schinasi (Co-Founder of Hulken) and Lee Rotenberg (CRO of Hulken) for a wide-ranging conversation on building, pivoting, and scaling across both venture-backed SaaS and a wildly successful consumer brand. From startup war stories in the NFX days to turning an “accidental business” into a $50M+ brand with a seven-person team, Alex and Lee share the kind of operator wisdom you only get after doing it multiple times.Together, they dive into:• The pivots that shaped Ivy and what they learned from exits• Why Alex & Lee love the 0→1 stage and how that founder energy shows up in consumer• How Hulken became a viral, new-category product with an organic social flywheel• The power of “pro” niches (thrifters, makeup artists, stylists) in driving brand adoption• Going premium on purpose: partnerships, positioning, and resisting “utility brand” gravity• Retail expansion lessons from Container Store to Target • Inventory planning, scarcity, and what happens when demand keeps surprising you• The modern Shopify tool stack: what works, what’s noisy, and why consolidation is coming• Where ecommerce is heading next 👥 Meet the guestsAlex Schinasi, Co-Founder at HulkenLee Rotenberg, CRO at Hulken🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters[00:00] Meet Lee & Alex: Serial Founders Behind Hulken[01:49] SaaS to Consumer: Why They Switched (and Why It’s Rare)[03:56] 3 Pivots + 2 Exits: The Ivy & Clay Origin Story[09:05] Hulken Was “Accidental”… Then It Took Off[13:35] The Viral Flywheel: How Hulken Grew Without Forcing It[18:05] Ops Reality Check: Inventory, Retail, and Scaling Lean[22:56] What’s Next: AI Shopping, Ecommerce Shifts, and Hulken’s Playbook[27:45] Founder Advice: Move Fast, Don’t Lie to Yourself🌐 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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51
Off Topic to On Target: Leadership, D2C’s Evolution & the Creator Economy
In this episode of The Orita Podcast, Aaron Schwartz sits down with Tetsuro Miyatake, CEO of Off Topic, one of Japan’s top tech podcasts, and investor at Harizury, for a global view of what’s next in commerce, content, and consumer tech.Together, they unpack:• Why Japan’s retail landscape may hold the key to DTC’s future and why most U.S. brands fail to break in• The "attention + trust" equation: how AI is flooding the content market, and why effort and intimacy are the new creative currency• What creators get wrong about building brands and how smart founders are hiring creators instead• From Anchor to IRL pop-ups: how Tetsuro’s side project turned into a media powerhouse, and what U.S. brands can learn from Off Topic’s rise• The Harizury playbook: what Tetsuro looks for when investing in early-stage software and DTC startups across both sides of the Pacific👥 Meet the guestTetsuro Miyatake, CEO of Off Topic & Investment Manager at Harizury🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai[00:00] How Orita Met Off Topic: When Founders and Podcasts Collide[02:42] From Side Hustle to Media Powerhouse: Off Topic’s Unlikely Rise[05:29] Why U.S. Brands Flop in Japan (and How to Get It Right)[08:07] Inside a VC’s Head: What Actually Gets Funded[11:01] Founders That Win: The Traits Investors Actually Bet On[13:48] Attention ≠ Impact: Why Marketing Is Broken (and How to Fix It)[16:21] AI Is Flooding the Feed, What Comes After Cheap Content[19:06] The New Gold Standard: Attention + Trust = Brand Equity[22:04] Creators over Celebrities: The New Face of Authentic Growth[24:59] From Clicks to Community: How IRL Builds Loyalty in 2026[27:27] Startup Gaps Nobody’s Solving (Yet)[30:02] Cracking Japan: How to Actually Enter a Hyper-Savvy Market🌐 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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50
Swipe, Buy, Ghost: Fixing Post-BFCM Churn Before It Starts
In this episode of The Orita Podcast, Aaron Schwartz brings together two of the sharpest retention minds in e-commerce, Gabrielle Pitman (Client Strategy Director, eBusinessPros) and Josh Behr (Founder, A&B Interactive), for a no-nonsense deep dive on email, SMS, and what really drives profitable lifecycle marketing in 2025 and beyond.They unpack:• Inbox reality check, how Gmail/Yahoo changes have killed “batch & blast” and why engagement, not volume, now decides whether you inbox or disappear• Retention math that works, shortening the window from first to second purchase, boosting LTV, and using post-purchase flows to drive cashflow (not just vibes)• Sending less to make more, when cutting 30–50% of campaign volume increases revenue per recipient, and how to defend that strategy to a “send more” CEO• Segmentation vs. spray & pray, how tools like AI-driven send logic and dynamic content can quietly prune dead weight, protect deliverability, and still hit revenue targets• Personalization that isn’t creepy, using behavior, reviews, and real customer stories (not just first name tags) to create “luxury touch at scale”• BFCM hangovers & ghost buyers, what to do with first-time Black Friday discount shoppers, and how gift cards, GWPs, and smarter offers turn a deal hunter into a repeat buyer• Flows vs. campaigns, why most brands over-invest in blasts, under-invest in flows, and how to fix your first 14 days after purchase so customers want to come back• Profitability over vanity, understanding net conversion (orders – returns + exchanges), discount conditioning, and why “more sends” is not a long-term strategyIf you’re a lifecycle marketer, agency operator, or founder staring at soft post-BFCM numbers, worried about unsubscribes, or trying to do more with less while keeping Google happy, this episode is your retention playbook.👥 Meet the guestsGabrielle Pitman: Client Strategy Director at eBusinessPros, a lifecycle agency focused on email, SMS, and direct mail for deeper personalization and retentionJosh Behr: Founder at A&B Interactive, an email & SMS agency built by ex-in-house operators obsessed with margins, deliverability, and customer LTV🎙️ Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters[00:00] Meet the Retention Heavyweights: Who’s Behind the Strategies[02:48] Email Isn’t Dead, You’re Just Using It Wrong[05:45] From “Hi First Name” to Actually Personal[08:48] The Tech Stack That Makes Customers Want to Click[11:36] Why They Buy, Why They Bounce, and How to Keep Them[14:28] Designing a Customer Journey They Don’t Want to Leave[17:37] Teach Before You Sell: Product Education That Prints Money[20:24] Turning Buyers Into Believers: How Real Brands Build Community[23:11] Your Secret Weapon: What CX Teams Know That Marketers Don’t[26:27] Rapid-Fire Lessons: What Today’s Best Retention Marketers All Share[28:13] Story vs. Discount: Brand Narratives That Outperform Promo Codes[36:43] Don’t Waste the First Purchase: How to Win the Second One Faster[40:30] After the Sale: Smart Plays That Keep Customers Coming Back[50:16] Beyond BFCM: How to Future-Proof Retention Going Into 2026🌐 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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49
Cutting Through the Noise: UX, ROI, and a Straight Razor
In this episode of The Orita Podcast, Amanda Vogt Peer (Chief Digital Officer at V’s Barbershop) and Jamie Schreter (Founder & Agency Director at DigitalJAS) break down how a 65-location, franchise barbershop brand is turning a nostalgic in-chair experience into a modern, omnichannel growth engine, without losing its soul.They discuss• Classic chair, modern stack: How V’s uses Shopify, Klaviyo, and booking tools to make an old-school service business feel seamless online• One brand, many paths: Appointments, products, franchise leads, content: building a UX that lets every visitor “convert” the way they want• Data from the chair: Connecting POS, walk-ins, and web so barbershop visits fuel smarter marketing instead of messy spreadsheets• Retention over rush: Why recurring services and trust beat BFCM blasts and discount addiction in a service-led business• Education as edge: Using “Groom U” content, product pages, and post-cut emails to become the default men’s grooming authority• AI with boundaries: Where automation helps (cleaner data, smarter segmentation, accessibility) and where human creativity still leads• Franchise without chaos: How a tiny HQ team keeps 65+ locations on-brand while giving owners room to win locally• What’s next for 2026: Live shopping, social-first barbers, and the men’s grooming boom that’s reshaping expectations for male consumersFrom appointment flows and first-haircut memories to data architecture and AI tooling, this episode is packed with practical ideas for operators juggling physical locations, e-commerce, and franchising, especially if you’re trying to modernize a legacy experience without breaking what made it special.👥 Meet the guestsAmanda Vogt Peer: Chief Digital Officer at V’s BarbershopJamie Schreter: Founder & Agency Director at DigitalJAS🎙️ Hosted byAaron Schwartz, Co-founder & Co-CEO at Orita.ai🎧 Chapters[00:00] From One Shop to 65+ Locations: How V’s Turned Old-School Cuts into a Digital Machine[04:24] E-Comm Meets the Barbershop Chair: Making Omnichannel Actually Work[10:10] Text, Tap, Trim: Designing a Frictionless Grooming Experience Online & In-Store[16:44] Not Just “Buy This Gel”: How V’s Uses Education to Sell Smarter (and Keep Trust)[21:16] The Data Mess Behind the Chair: Wrestling POS, Walk-Ins, and Web into One View[27:33] AI in a Human-Centered Business: Where Automation Helps (and Where It Doesn’t)[31:26] From 2-in-1 to Rituals: Why Men’s Grooming Is Exploding (and What’s Changed)[32:52] Marketing to the New Grooming Guy: What Actually Lands with Gen Z & Beyond[34:05] TikTok Meets the Barbershop: Will Live Social Shopping Be the New QVC for Men?[36:02] Beyond the Fade: Turning Barber–Client Moments into Lifelong Relationships[39:48] When Everyone Sells “Premium”: How V’s Wins on Retention, Not Just Acquisition[42:44] More Than “Book Now”: Building Engagement Before, During, and After the Cut[48:47] Authentic, Not Stuck-in-the-Past: Modernizing a Legacy Brand Without Losing Its Soul🌐 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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48
Bootstrapping a Billion-Dollar CRM: Growth, Guts & the Power of Owning Your Data
In this episode of The Orita Podcast, Aaron Schwartz sits down with Ed Hallen, Co-Founder and Chief Strategy Officer at Klaviyo, to talk about Ed's incredible journey from bootstrapping Klaviyo in the early days to powering some of the world’s fastest-growing e-commerce companies today. Ed shares rare, inside-the-room insights on scaling, strategy, and customer obsession.Together, they dive into:• Why Ed believes the founder’s mindset never goes away• Klaviyo’s early bet on data, how it shaped their approach to product• The real role of AI in product and marketing• Why Klaviyo invests so deeply in partners, and what makes those partnerships thrive• What brands are getting right, where they’re struggling, and how smart software gives them an edge• Ed’s long view: Why the real goal isn’t going public, it’s empowering people to build things that matter👥 Meet the guestEd Hallen, Co-Founder & Chief Strategy Officer at Klaviyo🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters[00:00] From Code to Klaviyo: Meet Ed Hallen[02:39] “Chief Strategy Officer”...But What Does That Actually Mean?[07:16] Customer Experience Is Everything: Here’s Why Ed Still Answers Support Tickets[09:49] How Klaviyo Stays Fast While Scaling to the Moon[15:06] AI at Work: What’s Helping, What’s Hype, What’s Next[19:21] Solving More Problems, Not Just Adding More Features[20:31] The Case for Building Around Your Customer, Not Yourself[23:44] The Partnership Flywheel: Why Ecosystems Drive Growth[27:51] The ROI of Real Customer Value and What It Takes to Deliver It[30:39] Modern Brand Survival Kit: What’s Changed, What Hasn’t[36:36] The Entrepreneur Era: Why the Next Wave of Founders Look Different[39:03] Klaviyo’s Legacy: Empowering Builders at Every Scale[40:44] Two Rules for Founders: Obsess Over the Problem, Break the Playbook🌐 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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47
The Flywheel Strategy: How to Turn AI into ROI for DTC Brands
In this episode of The Orita Podcast, Aaron Schwartz sits down with Kate MacCabe and Alexis Hurewitz of Flywheel Strategy for a behind-the-scenes look at how real customer-centric brands operationalize marketing, make AI useful (not scary), and actually get things done. From billion-dollar fashion houses to fast-growing DTC brands, Kate and Alexis break down what separates teams that ship great work on time from the ones drowning in Slack messages, last-minute “quick asks,” and AI buzzwords.They unpack:• Ops before AI, why messy workflows, scattered briefs, and unclear owners make AI less effective (and how to fix that first)• How great teams really work, the operating rhythms, intake systems, and “pace-setters” that keep marketing, creative, and product moving in sync• Creative + AI, not creative vs. AI, where AI can safely write, summarize, or structure content… and where human taste and storytelling are still non-negotiable• Flows vs. campaigns, why most brands over-invest in campaigns, under-invest in lifecycle flows, and what a healthier balance looks like• Risk without drama, how to build a culture where anyone can flag risks, without blame, and how to turn that into better decisions instead of bottlenecks• Alignment as a performance lever, the questions Flywheel asks in the first hour with a brand to surface real goals, pain points, and systemic issues• Preparing for 2026, how to plan headcount, tools, and AI usage so you don’t “get too lean” and accidentally lose your brand’s soulIf you’re a CMO, VP, or marketing/creative ops leader trying to scale campaigns, adopt AI without chaos, and keep your team sane while you do it, this episode is a blueprint.👥 Meet the guestsKate MacCabe: Founder of Flywheel Strategy | Kate helps growth-stage and enterprise brands design the operating systems, cross-functional structures, and tech strategies that actually unlock “magic” between data, design, and engineering.Alexis Hurewitz: Marketing & Creative Operations leader at Flywheel Strategy | Alexis specializes in request intake, trafficking, timelines, and campaign execution across print, digital, and in-store, so big ideas turn into on-time launches instead of burnout and chaos.🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO, Orita.ai🎧 Chapters[00:00] From Big Brands to Flywheel: Why This Team Exists[02:45] Before AI, Fix This: The Hidden Power of Ops Foundations[05:35] Silo Wars: Getting Marketing, Creative & Product to Play Nice[08:19] Stuck or Scaling? How to Spot Real Bottlenecks in Your Business[11:07] AI Hype vs. Reality: Where It Actually Belongs in Your Marketing[13:59] No Blame, Just Better: Building a Culture Where Risks Are Safe to Surface[16:39] Do More With Less: Using AI to Kill Busywork (Not Creativity)[19:29] Everyone Rowing the Same Way: Aligning Goals, Teams & Timelines[22:26] Email & SMS That Don’t Annoy People: Smarter Sending, Bigger LTV[25:21] Don’t Lose the Soul of Your Brand: Using AI Without Becoming Generic🌐 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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46
Sticky Strategies: Secrets to Customer Retention and DTC Growth
In this episode of The Orita Podcast, Aaron Schwartz sits down with Nikki Tooman, co-founder of Sticky Digital and one of the most respected operators in retention marketing, for a candid, tactical masterclass on what it really takes to build a high-performing lifecycle engine in 2025. From RFM models to subscription strategy to messaging discipline, Nikki breaks down why most brands over-message, under-segment, and overwhelm customers and how elite retention teams flip that script.Together, they unpack:• Less sends, more revenue, why scaling back campaigns often increases profit, and how to diagnose over-messaging• Retention flywheel strategy, how Nikki ties email, SMS, loyalty, and subscription into one cohesive, data-backed customer journey• RFM modeling that works, what first-time vs. returning customers convert on (spoiler: they’re NOT the same)• Loyalty 2.0, why points are dead and how punch cards, perks, and product-driven value create real repeat behavior• Subscription done right, how to integrate Recharge, Skio, or Ordergroove without fragmenting your data or your experience• Tech stacks that scale, the tools Nikki loves (Klaviyo, Postscript, Replo, Rebuy, Revo, Hiro Analytics) and the red flags she sees when agencies push “rip-and-replace”• SMS reality check, why brands waste thousands texting disengaged customers and how to rebuild high-intent cohorts post-BFCM• 2026 predictions, from CDP-powered retention to wallet passes, push-like messaging, and next-gen customer journeysIf you’re a DTC founder, CRM manager, or lifecycle marketer trying to maximize profit without burning your list, or you simply want to understand what great retention looks like, this episode is your blueprint.👥 Meet the guestNikki Tooman, Co-founder of Sticky Digital, a 28-woman retention agency focused exclusively on lifecycle, loyalty, subscription, and driving profitable repeat revenue for modern e-commerce brands.🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters[00:00] How Nikki Tooman Became a Retention Powerhouse[01:38] Why Retention Beats Acquisition Every Time[04:44] Stop Over-Messaging: The Real Key to Customer Engagement[07:23] Building a Retention Flywheel That Prints Revenue[10:33] The Retention Stack: Tools Top Brands Actually Use[13:14] Loyalty 2.0: Punch Cards, Perks & Programs That Work[15:54] What’s Next in Retention: 2026 Trends You Can’t Ignore[19:00] Tactical Advice Every Brand Should Follow Post-BFCM[21:52] Where to Find Nikki + How Sticky Digital Helps Brands Win🌐 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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45
Beyond the Funnel: Building Smarter DTC Brands
In this episode of The Orita Podcast, Aaron Schwartz goes international with Jason Anderson (COO, Andzen) and David Visser (CEO, Zyber) for an honest look at what it really takes to run a high-performing agency in 2025, from the APAC POV where budgets are tighter, brands move faster, and the bar for strategy is way higher.They break down:• The real reason APAC brands outpace the U.S. on innovation (and why “you can’t phone it in” down under)• How great agencies audit CRM, UX, data, deliverability, tech stacks, and customer journeys and the shocking misses they still see• Shopify + Klaviyo ecosystems: the tools they love, the ones they avoid, and the ones brands misuse the most• What makes a world-class retention or lifecycle program and why most brands are leaving millions in unused data• The truth about AI: what agencies should automate, what they never should, and how MCP access unlocks a new era of hybrid strategy• Why the future of agencies isn’t hours, it’s outcomes, IP, community, and leverageThis one is packed with candid stories, tactical frameworks, and real-world examples from two leaders who’ve seen hundreds of brands up close. Whether you run an agency, hire one, or are trying to scale a brand with fewer people and more impact, this is a masterclass in how to stay sharp in an increasingly crowded ecosystem.👥 Meet the guestsJason Anderson: COO at Andzen | CRM, personalization & loyalty expert | Klaviyo Elite Master PartnerDavid Visser: CEO at Zyber | Shopify Premier Partner & Klaviyo Master Platinum Partner | Community builder at Unlocked🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO, Orita.ai🎧 Chapters[00:00] Going Global: Why APAC Brands Play a Different Game[03:57] The Power of Niching Down: Why Agencies Went All-In on E-com[06:55] Agency Life Unfiltered: Chaos, Opportunity, and the Dark Side[10:00] “You Think You Know the Problem… But You Don’t”[11:56] Data Over Opinions: How Retail Brands Win Faster[18:27] 10,000 Data Points an Hour: The Magic of E-com Behavior[19:08] The $10M Brand Audit: Where CRM Breaks (and How Pros Fix It)[20:01] Deliverability, Infrastructure & List Health: The Hidden Revenue Leaks[21:29] Email Benchmarks That Don’t Lie: What Top Brands Do Differently[22:47] Your Tools Don’t Matter… Unless They Talk to Each Other[23:50] Reviews, Loyalty, Quizzes: Picking Tools That Make You Money[24:44] The App Graveyard: Cutting the 70 Tools You Don’t Need[28:58] The Shopify Deep Dive: How Elite Teams Audit a Storefront[33:16] Shiny Tools vs. Real Impact: How Experts Vet New Tech[38:09] Building Big Brands in Small Markets: The NZ Playbook[39:40] Stop Sending Flyers via Email: What Modern Retention Really Requires[41:04] Why Products Fail Without People (and People Fail Without Strategy)[42:03] Agencies in 2026: Less Headcount, More Impact[43:04] AI at Work: What to Automate, What to Never Automate[51:11] Requests for Startups: The Problems Begging to Be Solved🌐 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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44
From Pop-Ups to IPO: Jake Cohen on Klaviyo’s Rise and What’s Next for Commerce
In this episode of The Orita Podcast, Aaron Schwartz sits down with Jake Cohen, 10-year Klaviyo veteran, Partner at Vinyl.vc, and co-founder of Privy, for a wide-ranging conversation on what really drives durable revenue, great products, and fundable companies in 2025. From pop-ups to a billion dollars in BFCM revenue in a single day, Jake unpacks the patterns he’s seen across thousands of brands and dozens of early-stage startups.Together, they unpack:• The Privy pivot, how an “anti-Groupon” for restaurants accidentally became a must-have e-commerce growth tool• Vertical vs. horizontal SaaS, when to go deep in a niche, when to go broad, and why you should build generically but market specifically• The “fierce nerd” founder, the personality profile Vinyl looks for and why being both obsessive and insanely competitive is almost a requirement• Inside Klaviyo, steep-slope hiring, small autonomous teams, and why velocity matters more than being right 100% of the time• Durable vs. desperate revenue, how to set goals with competing metrics so you don’t grow top-line while quietly wrecking your margins and brand• AI as a power tool, not a god, what LLMs are great at today (ideas, copy, strategy scaffolding) — and where Jake draws a hard line on “agentic commerce” hype• Requests for startups, the next wave of infra: turning multi-person, multi-day workflows in marketing, personalization, and supply chain into a single button👥 Meet the guestJake Cohen, SVP at Klaviyo & Partner at Vinyl.vc; Co-founder of Privy🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters[00:00] Why This Episode Matters & Why Jake Cohen Is A Get[02:58] From Prada Stores to Product Manager: Jake’s Leap into Tech[05:45] Privy’s Plot Twist: How a Local Biz Tool Became an E-com Growth Engine[08:11] From Privy to Klaviyo: What Jake Learned About Relationships That Print Revenue[11:07] Vertical vs. Horizontal: How to Choose the Right Strategy Without Guessing[13:57] Build Generic, Sell Specific: The Hidden Art of Product Architecture[16:41] Inside Klaviyo’s Brain: Primitives, Data, and Adapting to Any Market[19:16] Interning for Your Customers: The Radical Empathy Behind Great Product[22:05] The “Fierce Nerd” Founder: How Jake Evaluates Who Deserves Venture Dollars[24:41] Craft Over Chaos: How Klaviyo Thinks About Product and Quality[27:05] Hiring on Slope: Why Curiosity Beats Credentials Every Time[32:46] Culture as an Operating System: How to Keep a Fast Company from Breaking[35:47] What Jake Sees in E-commerce Now (That Most Operators Miss)[42:38] AI as a Power Tool, Not a God: How to Use It Without Losing the Plot[46:40] Requests for Startups: Where the Next Wave of Commerce Innovation Will Come From🌐 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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43
The Agency Whisperer: Rachel Jacobs on Building Community & the Future of Agencies
In this episode of The Orita Podcast, Aaron Schwartz sits down with Rachel Jacobs “the e-commerce agency whisperer” and founder, of Ecommerce Agency Growth & Ecommerce Partnerships, for a brutally honest look at what it really takes to build, scale, and sell an e-commerce agency. From retainers and operations to M&A and partnerships, Rachel pulls back the curtain on how the best agencies run and why most never get there. Together, they unpack: • Retainer-first models, how agencies move from one-off projects to durable, scalable recurring revenue • Tacticians vs. operators, why so many founders become the bottleneck and how to build the layer that frees them • Agency consolidation, what’s driving niche rollups, service “amputations,” and the coming wipeout of low-value shops • Niching with intent, how to move from “all things to all people” to a focused offer that commands premium pricing • Partnerships that work, why tech–agency relationships fail, and how to become the partner everyone wants to bet on • Choosing tech & AI, how smart agencies evaluate tools, turn data into real strategic insight, and avoid the hype cycle • Community as a moat, how Rachel built a 20,000+ strong agency network and why “rising tide lifts all ships” is a business strategy If you’re an agency founder, e-commerce leader, or SaaS operator trying to navigate a crowded ecosystem, understand where to focus, and build a business that’s sellable (not just busy), this episode is your playbook. 👥 Meet the guest Rachel Jacobs, Founder of Ecommerce Agency Growth & Ecommerce Partnerships, advisor, community builder, and “agency mother” to thousands of e-commerce shops worldwide 🎙 Hosted by Aaron Schwartz, Co-Founder & Co-CEO at Orita.ai 🎧 Chapters 00:00 Rachel Jacobs: From Brand-Side Burnout to “Agency Whisperer” 02:47 Reinventing Agency Consulting: What Actually Works Now 05:18 Retainers That Stick: How Smart Agencies Build Predictable Revenue 07:57 From Lonely Founder to Global Tribe: The Power of Agency Community 10:38 Agency Extinction or Evolution? Surviving Consolidation & Market Chaos 13:21 Specialize or Stall: Why Generic Agencies Get Left Behind 16:08 Knowing When to Quit: Cutting Services, Clients, and Dead Weight 18:56 What’s Next for Agencies: Rachel’s Forecast for the Next 3–5 Years 19:10 Operator, Builder, or Innovator? The 3 Types of Agency Owners 20:58 Owning Your Niche: How Category-Leading Agencies Think 23:13 The Pivot: Moving from “We Do Everything” to “We’re the Best at This” 23:40 What Great Brands Expect from Great Agencies 25:17 No More “Throw It Over the Fence”: Fixing Sales-to-Delivery Misalignment 26:13 Drowning in Tools: How Agencies Navigate a Saturated Tech Stack 28:01 Spotting the 1%: How to Identify True Innovators vs. Copycats 30:26 Partnerships That Print Money (Instead of Waste Time) 32:27 Intentional or Transactional? The Real Difference in Winning Partnerships 35:07 Simplicity v Chaos: How to Make Real Progress in Your Agency Business 🌐 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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42
Retention, Reimagined: Data, AI, and Building Brand Loyalty
In this episode of The Orita Podcast, Aaron Schwartz sits down with Zac Cherin (Partner at Simplistic, Founder at Hiro) and Max Sturtevant (Founder at WellCopy) to dissect what the best retention agencies are really doing and what most brands are still getting wrong.They break down:• Pop-up psychology, mystery discounts, and why most forms kill conversions• Offer-first thinking, and how creative testing beats personalization for 99% of brands• Signal disruption, from plain text emails to refund lotteries and gifting funnels that actually work• Tech that matters, and what AI tools they’re watching (or avoiding) going into 2026• Rethinking BFCM, and why owning your own holiday might beat chasing Black Friday hypeThis one is full of hard-won tactics, honest advice, and actual data from hundreds of brands. Whether you run a lifecycle team or hire one, this is a must-listen on doing more with less and keeping your edge in a noisy, copy-paste world.👥 Meet the guestsZac Cherin: Partner at Simplistic | Founder of Hiro | Lifecycle & tech strategy leaderMax Sturtevant: Founder, WellCopy | Retention agency scaling 100+ brands with pure email performance🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO, Orita.ai🎧 Chapters[00:00] How Two Top Retention Agencies Actually Work Behind the Curtain[02:40] Content That Converts: What Still Works and What’s Dead[05:33] What Makes a Real Retention Agency (Not Just Another Klaviyo Shop)[08:26] Why Most Agencies Just Copy-Paste, And How to Be the Exception[11:00] Personalization Myths: When “Relevant” Becomes Irrelevant[13:40] Email Isn’t Dead, It’s Just Been Boring (Until Now)[16:32] Pop-Ups That Don’t Suck: Offers, Triggers, and Tactics That Work[19:22] Retention v Performance: How to Make Them Work Together[24:51] 2026 or Bust: The New Rules of Agency Positioning[27:01] Why Brand CMOs Are Taking the Wheel[30:02] Retention in Recession: What’s Actually Working in a Tight Market[32:47] Signal Disruption: The Anti-Trend That’s Driving Results[36:51] The AI We Use and the Tools We’ve Stopped Believing In[39:52] Stop Reporting Fluff: The Metrics That Actually Matter43:53] How to Keep BFCM Customers From Ghosting in January🌐 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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41
Active Ingredients: How U Beauty Blends Luxury Storytelling with Data-Driven Growth
In this episode of The Orita Podcast, AJ Patel (SVP of Growth) and Shelly Nghiem (Director of E-commerce) from U Beauty peel back the curtain on how a luxury skincare brand scales sustainably without chasing trends, over-discounting, or bloating the tech stack.They discuss:• Luxury in the age of Amazon. Why U Beauty embraces omni-channel while protecting its premium identity• Subscriptions that stick. How segmentation, perks, and cancel-flow insights power retention• Flows, not flukes. Why testing never stops on email• Gen AI with guardrails. What U Beauty avoids and where they see future upside for high-touch personalization• Agility vs. enterprise. Lessons AJ brings from Unilever Prestige to a nimble, fast-moving team• “Ultra hard mode” marketing. Why doubling down on core products beats over-rotation in luxury DTCFrom first-party insights to hands-on retention tips, this one’s packed with strategic and tactical gold for marketers and operators building premium brands in a crowded ecosystem.👥 Meet the guestsAJ Patel, SVP of Growth at U BeautyShelly Nghiem, Director of E-commerce at U Beauty🎙️ Hosted byAaron Schwartz, Co-founder & Co-CEO at Orita.ai🎧 Chapters[00:00] Inside U Beauty: Meet the Leaders Behind the Luxe[05:58] Subscription Gold: How U Beauty Keeps Customers Hooked[09:05] From Unilever to U Beauty: Big Brand Tactics for Nimble Teams[12:01] Email That Converts: Real Testing Wins (and Surprises)[14:58] Flows That Work: The Secret Sauce Behind U Beauty’s Retention[17:58] Paid + AI: Smart Performance Tactics That Actually Scale[20:59] Luxury on Amazon? Why It’s Not a Trade-Off Anymore[23:58] Beyond DTC: What’s Next in Omni-Channel for Premium Brands[26:56] What Every Brand Needs to Hear Before 2026 Hits🌐 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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40
Growing Up CPG: Lucas Ballasy on Scaling Brands and Barrel
In this episode of The Orita Podcast, Aaron Schwartz talks to Lucas Ballasy, CEO of Barrel, a digital partner helping omnichannel CPG brands build meaningful, connected experiences across every channel. From shaping enterprise CPG ecosystems to elevating fast-growing consumer brands, Lucas brings a rare mix of design roots, human-first leadership, and real-world operator wisdom.They discuss:• AI search (AEO/GEO): the future of discoverability and why CPG brands must shift from keyword hacks to solving real customer jobs-to-be-done• Your digital flagship: Why a CPG brand’s website anchors the entire omnichannel ecosystem (DTC, retail, POS, B2B, marketplaces)• Talking to customers: The lost art that unlocks product, messaging, and brand education across all channels• Human-first leadership: How culture, clarity, and communication shape modern agency teams• Marketplaces that matter: How CPGs can win on Amazon without undermining their owned digital presence• Subscription + loyalty for CPG: When to bundle, when to specialize, and how to create programs customers actually value• What’s next for CPG brands: Crafting connected digital-to-retail journeys that drive growth, retention, and brand loveIf you’ve ever wondered how top CPG brands stay loved and scalable in 2025’s chaos, this one’s for you.👥 Meet the guestLucas Ballasy, CEO, Barrel🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO, Orita.ai🎧 Chapters[00:00] Meet Barrel: The Agency Powering Today’s Top CPG Brands[02:35] Lucas’ Leadership Playbook: How to Build Humans-First Teams[05:09] Inside Barrel’s CPG Blueprint: What Winning Brands Do Differently[07:31] Why Talking to Your Customers Is a Growth Superpower[10:42] Amazon, DTC, Retail: Crafting a Marketplace Strategy That Works[14:15] Unboxing Matters: How Packaging Shapes the Customer Experience[17:58] Subscriptions & Loyalty: The Programs That Actually Build Retention[19:37] Let the Data Speak: Smarter Decisions, Better Brands[22:36] AI Search Is Here: How AEO Changes Everything[26:38] Lucas’ Closing Advice for CPG Founders & Operators🌐 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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39
Retention Royalty: Two Experts Turning Email and SMS Into Revenue Machines
In this episode of The Orita Podcast, Aaron Schwartz sits down with Mya Gupta (VP of Client Services, 1r) and Kelsey Carstens (Director of Email & SMS, Bad Marketing) for an unfiltered look at what it really takes to build unified, retention-first commerce in 2025.From agency partnerships to AI hype, they unpack what makes great customer experiences scalable and what still can’t be automated.They discuss:• Retention over reach, why keeping customers is cheaper, smarter, and still misunderstood• Bold brands win, how entertainment, personality, and risk drive loyalty• Bundle vs. Best-in-class, when to simplify your stack vs. go deep on data• Deliverability drama, why inbox placement, segmentation, and sunset policies now decide LTV• Unified commerce, connecting online, offline, and AI-assisted touchpoints into one seamless journey• AI as the start, not the finish, where automation saves time and where human creativity still wins👥 Meet the guestsMya Gupta, VP of Client Services, 1rKelsey Carstens, Director of Email & SMS, Bad Marketing🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO, Orita.ai🎧 Chapters[00:00] Meet Mya & Kelsey: Two Operators Who Tell It Like It Is[03:27] Disruptive Marketing: Why Playing Safe Is Losing[07:12] How to Build Partnerships Brands Actually Love[10:48] First Look Under the Hood: How They Audit a Brand[15:49] Retention Is Rising: Where Spend Is Really Shifting[20:01] Unified Commerce: Winning Across Every Touchpoint[22:37] Tech Stack Truths: When to Bundle vs. Go Deep[24:14] Rewards That Work: Turning Value Into Loyalty[26:37] Why Clean, Simple Stacks Outperform Complicated Ones[28:16] Retention Simplified: Remove Friction, Keep Customers[29:54] The New Mix: Acquisition vs. Retention in 2025[33:51] Authenticity Wins: How Brands Actually Build Trust[36:37] AI in the Wild: What Helps and What’s Still Hype[44:04] What Lasts: Loyalty, Experience, and Brand Strategy🌐 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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38
The Guy Big Brands Call: Rick Watson on What He’s Learned Advising the DTC 1%
In this episode of The Orita Podcast, Aaron Schwartz sits down with Rick Watson, Founder & CEO of RMW Commerce, for a deep dive into the real state of e-commerce, where omnichannel meets reality, and where growth meets gravity.Together, they unpack:• Breaking the legacy mold, how big brands modernize without losing what made them great• The DTC ceiling, why even the best Shopify brands plateau at $100–150 M and what to do next• Amazon vs. Walmart, who’s truly positioned to win the next decade of marketplace wars• Omnichannel math, how to balance wholesale, retail, and DTC without killing your margins• The enterprise trap, why many SaaS companies stall between $15K and $75K ACV• The Renaissance CFO, how finance leaders quietly shape the new operator playbook• AI & agents in commerce, what’s hype, what’s here, and how it will reshape service, marketing, and supply chainIf you’ve ever wondered how modern retail actually works, and what separates the brands that adapt from the ones that fade, this episode is your roadmap.👥 Meet the guestRick Watson, Founder & CEO, RMW Commerce Consulting🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters[00:00] Meet Rick Watson: The Guy Who’s Seen Every E-Commerce Playbook[02:34] Why Most “Growth Strategies” Fail Before They Start[05:21] The Hardest Shift in Commerce: From Legacy to Modern[07:56] The DTC Ceiling: Why $150M Is Where Most Brands Stall[10:27] Omnichannel Without Chaos: How Smart Brands Scale Profitably[12:56] Amazon, Walmart & the Marketplace Power Struggle[15:35] Retail Media Networks: The Hidden Goldmine in Commerce[18:12] Shopify’s Next Chapter and the Risks No One Talks About[25:26] Why Enterprise Brands Still Don’t Get Shopify (Yet)[27:20] The Rise of the Renaissance CFO: From Gatekeeper to Growth Partner[34:25] AI’s Real Role in Commerce: Beyond the Buzzwords[38:29] How Personalization Actually Builds Retention[42:42] The Two Currencies of Retail: Price vs. Trust[45:37] Final Thoughts and What’s Next for E-Commerce Operators🌐 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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37
House Slippers to Household Name: Bianca Gates on Building Birdies
In this episode of The Orita Podcast, Aaron Schwartz sits down with Bianca Gates, Co-Founder & CEO of Birdies, to unpack what it really takes to build a beloved consumer brand, from the early scrappy days to leading a post-acquisition company without losing your spark.They tackle:• The “pick your seat” mindset, the childhood lesson that shaped Bianca’s entire career• Sales as a superpower, why storytelling and persuasion matter more than design degrees• Pivoting with purpose, how Birdies turned customer complaints into its biggest growth moment• The emotional toll of feedback, staying resilient when your DMs turn into public reviews• Omnichannel vs. DTC, when it’s time to leave the comfort of e-commerce and expand IRL• AI & quality, why the future of consumer brands belongs to those who obsess over reviewsIf you’ve ever wondered how great founders turn landmines into lessons, this one’s for you.👥 Meet the guestBianca Gates, Co-Founder & CEO, Birdies🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO, Orita.ai🎧 Chapters[00:00] Meet Bianca Gates: From Curiosity to CEO[02:33] How Sales Taught Her Everything About Leadership[05:27] Birdies: The Side Hustle That Took Flight[08:12] The Pivot That Changed Everything[11:13] Building Brand Love: Community Over Campaigns[13:59] Turning Complaints Into Growth Fuel[17:00] Resilience 101: Handling Hate and Staying Human[22:56] Life After the Exit: What Really Changes[26:26] Omnichannel vs. DTC: The Real Playbook[28:40] The Only Marketing That Matters: Great Product + Reviews[30:41] AI in the Trenches: How Birdies Uses It to Listen Smarter[33:47] Outsource or Own It? The New Brand Equation[38:19] What’s Next for Birdies (and Bianca)[40:25] Her Hard-Won Advice for Founders Everywhere🌐 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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36
AI-Driven Retention: The Next Era of Lifecycle Marketing
In this episode of The Orita Podcast, Aaron Schwartz sits down with Omar Lovert (Polaris Growth; Klaviyo Legend, Co-host, Klaviyo Geeks) and Bogdan Mihalache (Founder, Email Kong; Co-host, Klaviyo Geeks) for a masterclass on email, retention, and the art of sending more without losing your soul.Together, they unpack:• Flow timing myths, why “wait 24 hours” is bad advice and how to capture intent while it’s hot• Segmentation traps, the engagement segments that quietly kill 75 % of your list (and your LTV)• Deliverability 101, how to get out of spam, live happily in Promotions, and stay in the inbox• AI vs. Operators, when machine-generated copy helps, when it hurts, and how to use GPT as a thought partner• Profit, not vanity, the metric most founders obsess over that isn’t the right measure of retention health• BFCM sanity check, how to prep early, send more, and build loyalty instead of discount addictionStick around for Klaviyo tips, wild deliverability hacks, and the kind of straight talk that only comes from two operators who’ve seen every email mistake in the book, and fixed them.👥 Meet the guestsOmar Lovert: Co-Founder & Managing Director, Polaris Growth | Klaviyo Legend | CRO & CRM expertBogdan Mihalache: Founder, Email Kong | Retention & Automation specialist🎙 Hosted byAaron Schwartz, Co-founder & Co-CEO, Orita.ai🎧 Chapters[00:00] Meet the Klaviyo Legends: Omar & Bogdan Take the Mic[03:28] From Building Sites in ’98 to Email Empires in 2025[06:26] Email Showdown: When Strategy Meets Gut Feel[09:35] Two Geeks, One Goal: Sharpening Each Other’s Game[11:43] Think Like Your Customer (Before You Hit Send)[15:20] Where Great Brands Focus, And Where They Waste Time[16:37] Hidden Gold in Klaviyo: The Workflows Everyone Misses[21:51] Stop Over-Segmenting: Why Your List Is Smaller Than You Think[28:28] Spam, Promotions, or Primary? The Deliverability Truth[30:30] AI in Email: Hype, Hope, and Real Use Cases That Work[44:34] Smarter Than Templates: Using AI for Real Optimization[52:09] BFCM Survival Mode: Send More, Stress Less🌐 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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35
Rescue, Revive & Thrive: How Fan Bi Turns Around Overlooked Brands
In this episode of The Orita Podcast, Aaron Schwartz sits down with Fan Bi, operator, investor, and founder of Blank Label (acquired) and The Hedgehog Company, for an honest look at what happens when growth at all costs collides with the laws of profitability.Together, they unpack:• Zombie brands 101, how to spot when common equity is out of the money (and may never be again)• The real multiple, why sub-$50M brands trade on profit, not fantasy revenue numbers• Platform myths, why shared ops, shared customer lists, and “synergy” rarely pencil out• The operator’s playbook, margin targets, repeat behavior, and cutting operational complexity• Resetting expectations, how to turn a not-yet-profitable brand into a durable business• AI as a thought partner, how real operators are using (and mistrusting) chat models in 2025• BFCM prep for mortals, what to do if your Q4 plan misses, and how to protect your liquidity👥 Meet the guestFan Bi, Co-Founder & Managing Partner at The Hedgehog Company🎙 Hosted byAaron Schwartz, Co-founder & Co-CEO at Orita.ai🎧 Chapters[00:00] When Founders Stop Pretending: Welcome to The Orita Podcast[01:50] How Fan Bi Went from Custom Shirts to Capital Stacks[03:09] From Blink Label to Hedgehog: The Operator Becomes the Investor[05:07] The Harsh Truth About Valuations (and Why Profit Still Wins)[07:42] The Real Checklist: Margins, Repeat Buys, and Operational Chaos[10:16] Inside the P&L: Common Founder Blind Spots That Kill Profit[12:52] Retention Over Reach: Why Growth Isn’t Always the Goal[15:21] The Market Doesn’t Care About Your Slide Deck (and That’s Good)[16:59] The Platform Mirage: Why “Synergy” Rarely Pays the Bills[19:35] Zombie Brands: When Founders Don’t Know They’re Already Gone[21:22] The Emotional Hangover of Building (and Letting Go)[23:05] AI in E-Commerce: Overhyped, Under-Delivered, Still Inevitable[25:41] If We Started a Brand Today… Here’s the Playbook[28:09] Revenue Quality to Growth Rate: The Quiet Moat No One Talks About[30:41] Omnichannel Dreams vs. Operational Nightmares[33:08] Black Friday Forecast: How to Survive a Soft Season[34:29] Where to Find Fan Bi (and Why You’ll Want to)🌐 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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34
Slice, Scale, Repeat: Inside Misen’s DTC Evolution
In this episode of The Orita Podcast, Michael Mahoney, CEO at Misen, and Katharine Azzolini, Senior Lifecycle Marketing Manager at Misen, walk us through how a 12-person cookware team balances profitability, creativity, and relentless product focus, without drowning in tools or distractions.They tackle:• Do less, better. How Misen drives $50M+ revenue with a small team and crystal-clear priorities• Ops meets ethos. Why spin-to-win doesn’t fit their brand, and how they simplify instead of chase trends• Lifecycle that works. How AI + segmentation help personalize flows, winbacks, and launches without spamming• Launching with loyalty. How Kickstarter fuels product validation and customer acquisition without cannibalizing DTC• CAC ≠ the problem. Why most brands over-index on ad tweaks and under-invest in product and positioning• Saying no to too much software. What tools Misen avoids, and why focus beats stack bloat every timeFrom pre-order playbooks to data-led storytelling, this episode is a must-listen for any marketer, operator, or founder trying to scale a durable, lean brand, without breaking their team or customer trust.👥 Meet the guestsMichael Mahoney, CEO at MisenKatharine Azzolini, Senior Lifecycle Marketing Manager at Misen🎙️ Hosted byAaron Schwartz, Co-founder & Co-CEO at Orita.ai🎧 Chapters[00:00] – From Kickstarter to Kitchen Counters: Misen’s Origin Story[02:48] – How a 12-Person Team Runs a $50M Brand[05:20] – The Lifecycle Strategy That Keeps Customers Coming Back[08:26] – Why Education Is Misen’s Secret Marketing Weapon[11:17] – Build What They Want: Customer-Back Product Development[13:44] – The AI Stack That Actually Works (and What Doesn’t)[16:41] – What Misen Really Thinks About Attribution Models[19:24] – Kickstarting Loyalty: Launch Tactics That Stick[23:20] – Gut vs. Data: How Misen Decides What’s Next[25:59] – Inside Misen’s Test-and-Learn Playbook[28:26] – Staying Nimble: How to Build Flexibility into Growth[30:35] – Rethinking Retail: What “Omnichannel” Looks Like in 2025[35:05] – AI in DTC: What’s Worth It, What’s Just Hype[37:24] – Automate Smarter: Misen’s Practical AI Use Cases[42:44] – Don’t Cannibalize Yourself: Launching New Products Without Losing Old Sales[45:37] – What Every Marketer Needs to Hear in 2025[47:23] – Bonus Round: Misen’s Fan-Favorite Products (and What’s Coming Next)🌐 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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33
Fresh Cuts, Bold Moves: How ButcherBox Blends Value, Data, and Loyalty
In this episode of The Orita Podcast, Aaron Schwartz sits down with Reba Hatcher, Chief Commercial Officer at ButcherBox, to unpack what it takes to build a mission-driven e-commerce brand that’s both profitable and personal.Together, they unpack:• Bootstrapped to $500M. How ButcherBox scaled sustainably while staying true to its values.• Retention is the job. Why "getting the box there frozen" beats any growth hack, and how to keep trust for the long haul.• Loyalty that listens. How Sizzle Society and 1:1 customer insights fuel personalization, perks, and retention.• AI that earns its keep. From cancel flows to custom deals, why ButcherBox uses AI with a human touch.• Do less, do better. How Reba’s ops background keeps the team scrappy, focused, and customer-obsessed.• Distribution without dilution. Expanding to Target, DoorDash, and retail, while keeping brand control.👥 Meet the guestReba Hatcher, Chief Commercial Officer at ButcherBox🎙️ Hosted byAaron Schwartz, Co-founder & Co-CEO at Orita.ai🌐 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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32
Unlocking the Ops Edge: Scaling DTC Through Smart Operations
In this episode of The Orita Podcast, Aaron sits down with two operators who’ve seen (and fixed) just about everything in e-commerce: Charles Cushing (Founder, StartOps) and Joe Gullo (SVP, Thursday Boot Company; ex-Glossier). We get into why ops is the quiet growth engine, and how the best brands turn constraints into velocity.They tackle:• Automation that actually ships: where AI + Sheets beat shiny SaaS for real ROI.• Own your data: why trusting a 3PL’s portal is like letting someone grade their own test.• Team design in 2025: fewer hires, more IC-style leaders, and the rise of fractional talent.• Tool stack sanity: when spreadsheets win, when to try new software, and how to make switching painless.• Ops x Retention: “get people what they ordered when you said you would” as the ultimate LTV unlock.• Community leverage: how StartOps crowdsources answers to the same hard problems across brands.Stick around for war stories (Jet.com hyperscale, packaging that shouldn’t pop like biscuit dough), practical tips you can steal this week, and a candid look at what’s next for ops-led growth.👥 Meet the guestsCharles Cushing: Founder, StartOps (community of 250+ senior ops leaders)Joe Gullo: SVP, Thursday Boot Company; Advisor, StartOps; former Head of Ops, Glossier🎙 Hosted by Aaron Schwartz, Co-founder, Orita.ai🎧 Chapters[00:00] How three operators met and why ops still matter.[03:00] StartOps Origins, building a no-vendors, operators-only community.[05:30] Jet.com hyperscale and the 500-Friend Warehouse[10:20] From Logistics to LTV, Aaron’s pivot from shipping chaos to smarter segmentation.[15:00] “It’s Not BS Anymore” Joe explains why automation finally works for ops.[18:20] Google Sheets to SaaS, How AI and scripts beat shiny platforms every time.[22:20] Death by Dim-Weight, The box-size problem that’s secretly eating your margins.[26:40] Speak CFO or Get Air-Freighted, Turning ops pain into financial fluency that CEOs hear.[36:40] Ops × Marketing: The Truce, Why packaging, forecasting, and timing decide customer joy.[44:40] Forecast or Ruin Christmas, Joe’s BFCM survival advice and what innovation really means in ops.🌐 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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31
From Sharp Edges to Soft Gels: Storytelling, Growth, and Longevity Marketing
In this episode of The Orita Podcast, Aaron Schwartz sits down with Dennis Bernstein, VP of Marketing & Growth at Serafina Therapeutics (Fatty 15), and a veteran of Procter & Gamble and Dollar Shave Club, for a masterclass in brand building.Together, they unpack:• From P&G to DTC. What 25 years of brand building taught Dennis about storytelling, innovation, and constraint.• Scrappy wins. Why small budgets spark better creativity, and how “underdog brands” can out-execute giants.• The Fatty 15 formula. How a single-product, science-backed supplement became a profitability case study.• Test-and-learn discipline. Why learning velocity beats channel sprawl, and how to align your exec team around risk.• Personalization without creep. Using data, surveys, and AI to teach, not chase, your customer.• Amazon on your terms. When to expand, how to keep education alive, and why every box should still feel human.If you’re a marketer, operator, or founder trying to build something durable in a world that changes fast, this conversation is your new playbook.👥 Meet the guestDennis Bernstein, VP of Marketing & Growth at Serafina Therapeutics (Fatty 15)🎙️ Hosted byAaron Schwartz, Co-founder & Co-CEO at Orita.ai🌐 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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30
Partners, Personalization & Performance: How Collaborations and Data Keep Brands Ahead of the Curve
In this episode of The Orita Podcast, Aaron Schwartz sits down with Aoife (eefa) Teague, PR-turned-partnerships pro at Octane AI, for a no-BS look at quizzes, zero-party data, and how to make partnerships actually ship revenue (not decks).Together, they unpack:• Stop guessing. Start asking. Why zero-party data beats “vibes” and how most brands still aren’t using it• Quizzes in minutes. Octane’s AI can spin up on-brand product finders from a prompt• Use it or lose it. The simple workflows to turn quiz answers into segmentation, personalization, and actual dollars• Partnerships that perform. Agency + tech tactics Aoife uses (templates, co-marketing, upkeep) so integrations drive outcomes• Better-together stack. Where Shopify, Klaviyo, and tools like Gorgias + Skio fit when you want retention that compounds• BFCM anxiety antidote. Make buying stupid-easy: optimized quiz flows, clear delivery expectations, and clean discount logic• When data surprises you. What happens when your audience isn’t who you thought, and how to pivot fastIf you’re a DTC operator, lifecycle lead, agency owner, or anyone still treating quizzes as a “nice to have,” this convo will upgrade your roadmap—or set it on fire (in a good way).👥 Meet the guestAoife Teague, Partnerships at Octane AI🎙️ Hosted byAaron Schwartz, Co-founder & Co-CEO at Orita.ai🎧 Chapters00:00 From PR to Product: Aoife’s Origin Story04:58 Why Partnerships? The Octane AI Pivot08:16 Quizzes in Minutes: Inside Octane’s AI Builder12:24 Zero-Party Data, Real-World Revenue16:56 Agency Alliances That Actually Move the Needle18:45 Turning Partnerships into Pipeline (and Proof)23:18 Your Customers Aren’t Who You Think29:03 The Playbook for High-Trust, High-ROI Partners30:33 Make Buying Easy: UX Tactics That Print Money🌐 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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29
Cookware, Capital & Contrarian Bets: Caraway’s Rise, Sticker’s Playbook, and the New Rules of Growth
In this episode of The Orita Podcast, Aaron Schwartz sits down with Jordan Nathan (Founder & CEO, Caraway) and Oren Charnoff (General Partner, Sticker Ventures; ex-founder of Fondue → acquired by Postscript) for a founder-meets-investor reality check on turning “cool brand” into a durable business: pricing, channels, AI, and the one metric VCs actually care about (hint: it’s not ROAS).Together, they unpack:• Caraway’s climb: From Teflon scare to non-toxic cookware brand — and why “newness” (drops, collabs, colors) fuels the whole funnel.• Omnichannel, done right: Sequencing DTC → retail → Amazon without whiplash, and choosing partners for lift, not ego.• Money moves: Price like you mean it, and why POAS + cash flow beat vibes and vanity.• Future playbook: AI that actually helps (CX bots, Slack data, “digital twins”) + retention tactics that go way beyond lazy segmentation.If you’re a DTC operator, brand founder, or investor who wants fewer “spray and pray” campaigns and more compounding advantage, this convo will either sharpen your roadmap—or torch the parts that need it. Either way, time to move.Meet the GuestsJordan Nathan, Founder & CEO at CarawayOren Charnoff, Co-Founder and General Partner at Sticker VenturesHosted by Aaron Schwartz, Co-CEO🎧 Chapters00:00 — Meet Jordan & Oren: From non-toxic cookware to no-nonsense investing04:21 — Caraway’s breakout: pricing high, launching smart, owning the shelf08:39 — Startup scars: what Jordan’s first venture got right (and wrong)13:00 — Investor X-ray: POAS v ROAS and the “creative, convincing, relentless” founder17:20 — Omnichannel, on purpose: DTC → retail → Amazon (without breaking the brand)20:39 — ROI or bust: sequencing bets, measuring lift, killing distractions21:23 — Channel moats: how timing + placement lock competitors out22:49 — Focus v FOMO: why doing one thing cold-bloodedly well wins24:05 — Timing the jump: launch now vs. five years from now (and why it matters)25:47 — Newness that moves revenue: drops, collabs, and press-worthy moments28:09 — AI at work: CX agents, self-serve data, and the “AI Jordan” twin30:47 — 1:1 at scale: personalization without the ick (email, SMS, onsite)33:08 — Play the long game: build for 10 years, not 10 weeks🌐 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
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28
Domaine Knowledge: Helping DTC’s Biggest Brands Future-proof with Shopify
In this episode of The Orita Podcast, Aaron Schwartz sits down with Domaine’s dynamic duo—Stacy Strom (Director of CRM & Lifecycle Marketing) and Kim Samuelsen (Director of Delivery & Head of Domaine Studio), to unpack how the world’s largest independent Shopify design and development team helps brands win right now. From enterprise re-platforms to founder-led up-and-comers, they break down AI-enabled personalization, cross-channel retention, and BFCM playbooks that don’t torch your list.They discuss:• Studio vs. Enterprise → how Domaine balances scrappy founder energy with enterprise-grade execution.• AI that actually helps → curated tools (XGen, Zowie, Tolstoy) that drive conversion and efficiency instead of chaos.• BFCM without burnout → early planning, site speed, code freezes, and contingency playbooks to stay sane.• Retention beyond the weekend → segmenting send tolerance, nurturing new BFCM cohorts, and turning returns/support into loyalty.👥 Meet the guestsStacy Strom: Director of CRM & Lifecycle Marketing, DomaineKim Samuelsen: Director of Delivery & Head of Studio, DomaineHost: Aaron Schwartz: Co-Founder & Co-CEO, Orita.ai🎧 Chapters02:50 — Domaine’s Glow-Up & Coopetition05:33 — Studio Mode: Scaling Scrappy Brands08:36 — The Stack That Actually Ships11:19 — AI: From Hype to How14:13 — BFCM Prep: Plan in June16:46 — Weekend Winners: Tactics That Work19:46 — Personalization Without the Creep22:37 — One Customer, Many Channels25:22 — What’s Next: 2026 Preview28:23 — Rapid-Fire Takeaways🌐 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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27
Hot Takes & Hard Truths in E-Comm
In this episode of The Orita Podcast, Megan Blissick (Director of Marketing & Partnerships at Orita) sits down with three powerhouse operators shaping retention and growth in e-commerce: Hannah Spicer (Founder, H. Spicer Consulting), Whitney Caldwell (Co-Founder, Code & Cart), and Kerri McDonald (Co-Founder, Greenhouse Agency).From launching careers on the brand side to building agencies that guide today’s fastest-growing Shopify brands, they share candid lessons on email, UX, and the future of retention.They tackle:• 📧 Email truths — why automations and smart segmentation drive more than batch-and-blast.• 🛍 BFCM in 2025 — how to prep without burning out your team or your list.• 🤖 AI, the good and the bad — efficiency boosters vs. chatbot horror stories.• 🧭 Retention redefined — why customer service, trust, and product quality matter more than clever hacks.• 🔑 Back to basics — what your site really needs to tell shoppers in 10 seconds.Stick around for hot takes on sustainability messaging, sweep-up campaigns, and the one piece of advice each guest thinks every founder should hear.👥 Meet the guestsHannah Spicer — Founder, H. Spicer ConsultingWhitney Caldwell — Co-Founder, Code & CartKerri McDonald — Co-Founder, Greenhouse Agency🎙 Hosted by Megan Blissick, Director of Marketing & Partnerships at Orita.ai 🎧 Chapters00:00 — Meet the Operators: From Brand-Side Grit to Agency Brains02:36 — Left Turns & Leap Years: How We Landed in E-Comm05:28 — Remote, But Real: Culture, Burnout & Boundaries08:14 — Email Isn’t Dead: Why Flows Still Print Money10:44 — The 80/20 of Flows: Welcome, Browse, Abandon, Repeat13:47 — Retention = Everything: CX, Shipping, Loyalty (and sanity)16:22 — AI in DTC: Hype vs. Help19:14 — 10x Yourself: Using AI to Kill Busywork25:27 — The Practical AI Playbook: What to Use, What to Skip31:39 — BFCM Without the Burnout: Offers, Ops & List Health45:48 — Do Good or Do Deals? When Sustainability Meets Sales🌐 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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ABOUT THIS SHOW
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.
HOSTED BY
Aaron Schwartz
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