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The Orita Podcast
Aaron Schwartz
47 episodes
1 day ago
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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Marketing
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All content for The Orita Podcast is the property of Aaron Schwartz and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
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.
Show more...
Marketing
Business
Episodes (20/47)
The Orita Podcast
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 guests

Kate 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

Show more...
2 weeks ago
49 minutes 20 seconds

The Orita Podcast
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 guest

Nikki 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

Show more...
2 weeks ago
25 minutes 7 seconds

The Orita Podcast
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 leverage

This 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 guests

Jason Anderson: COO at Andzen | CRM, personalization & loyalty expert | Klaviyo Elite Master Partner

David 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

Show more...
2 weeks ago
58 minutes 25 seconds

The Orita Podcast
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

Show more...
2 weeks ago
51 minutes 27 seconds

The Orita Podcast
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

Show more...
3 weeks ago
50 minutes 29 seconds

The Orita Podcast
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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4 weeks ago
50 minutes 8 seconds

The Orita Podcast
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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1 month ago
29 minutes 39 seconds

The Orita Podcast
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 guest

Lucas Ballasy, CEO, Barrel

🎙 Hosted by

Aaron 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

Show more...
1 month ago
28 minutes 22 seconds

The Orita Podcast
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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1 month ago
47 minutes 57 seconds

The Orita Podcast
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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1 month ago
45 minutes 42 seconds

The Orita Podcast
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 reviews

If you’ve ever wondered how great founders turn landmines into lessons, this one’s for you.

👥 Meet the guest

Bianca Gates, Co-Founder & CEO, Birdies

🎙 Hosted by

Aaron 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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1 month ago
44 minutes

The Orita Podcast
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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2 months ago
55 minutes 50 seconds

The Orita Podcast
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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2 months ago
35 minutes 58 seconds

The Orita Podcast
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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2 months ago
47 minutes 50 seconds

The Orita Podcast
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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2 months ago
41 minutes 50 seconds

The Orita Podcast
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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2 months ago
51 minutes 18 seconds

The Orita Podcast
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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2 months ago
51 minutes 15 seconds

The Orita Podcast
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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2 months ago
33 minutes 42 seconds

The Orita Podcast
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 Guests

Jordan Nathan, Founder & CEO at CarawayOren Charnoff, Co-Founder and General Partner at Sticker VenturesHosted by Aaron Schwartz, Co-CEO


🎧 Chapters

00:00 — Meet Jordan & Oren: From non-toxic cookware to no-nonsense investing

04:21 — Caraway’s breakout: pricing high, launching smart, owning the shelf

08:39 — Startup scars: what Jordan’s first venture got right (and wrong)

13:00 — Investor X-ray: POAS v ROAS and the “creative, convincing, relentless” founder

17:20 — Omnichannel, on purpose: DTC → retail → Amazon (without breaking the brand)

20:39 — ROI or bust: sequencing bets, measuring lift, killing distractions

21:23 — Channel moats: how timing + placement lock competitors out

22:49 — Focus v FOMO: why doing one thing cold-bloodedly well wins

24:05 — 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 moments

28:09 — AI at work: CX agents, self-serve data, and the “AI Jordan” twin

30:47 — 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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3 months ago
42 minutes 5 seconds

The Orita Podcast
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 guests

Stacy Strom: Director of CRM & Lifecycle Marketing, Domaine

Kim Samuelsen: Director of Delivery & Head of Studio, Domaine

Host: 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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3 months ago
49 minutes 21 seconds

The Orita Podcast
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.