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
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
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
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
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
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
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
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
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
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
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
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
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
In this episode of The Orita Podcast, Jordan Shamir (Co-Founder & CEO of Yofi) and Malc Miller (Co-Founder & CEO of Wage) join Aaron Schwartz for a conversation that zig-zags from Ohio State vs. Michigan trash talk to the hardest truths about building DTC startups.Jordan breaks down how Yofi grew from sneaker resale frustrations into an AI-powered fraud and abuse prevention platform trusted by major brands. Malc shares lessons from neuroscience and his time at Lululemon, now channelled into Wage—a gamified finance app that rethinks how communities learn, play, and invest.They tackle:• 🛑 Fraud isn’t just lost revenue — it wrecks CX, trust, and downstream data.• 🎮 Gamification, neuroscience, and why sparring with peers beats theory every time.• 🛠 The founder toolkit: slowing down to speed up, modular product design, and why being wrong (a lot) is part of the job.Stick around for why losing a Lululemon contract turned into the best thing that ever happened to Yofi.👥 Meet the guestsJordan Shamir, Co-Founder & CEO, YofiMalc Miller, Co-Founder & CEO, WageHosted by Aaron Schwartz, Co-Founder & Co-CEO at Orita.ai🎧 Chapters[00:00] Buckeyes vs. Wolverines - setting the tone [01:46] Malc’s path - neuroscience, soccer, systems thinking [05:00] Jordan’s origin story - schemer to startup operator [06:48] Yofi’s pivot - from sneaker chaos to CX-first fraud defense [08:52] Enterprise reality check - when no one owns fraud [12:07] The Lulu loss that leveled up Yofi [17:02] Inside future experiences at Lululemon - spotting patterns early [18:54] Wage 101 - pickup-game finance and learning by doing [21:33] Gamification that matters - win, lose, learn [23:56] Data you can trust - stop learning from dirty signals [31:55] Founder truths - assume you’re wrong, move anyway [34:34] Slow down to speed up - modular product over platform pitch [36:35] Team cadence - three outcomes per meeting, always [39:54] Hiring for ownership - problem finders vs. problem solvers [42:47] Build it, don’t debate it - design first, align fast [48:31] Where to find Malc and Jordan (and Wage’s waitlist) [49:45] Parting shots - momentum is manufactured [50:45] Sign-off - don’t do startups alone 🌐 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
In this episode of The Orita Podcast, Aaron Schwartz chats with two retention heavyweights from New Standard Co., Marina Carroll and co-founder Eric Rausch, to find out how top brands prepare for BFCM and scale smarter with email, SMS, and push. From testing frameworks to “send less, earn more,” they share what works across fast-moving DTC and subscription brands alike.
They discuss:
• BFCM prep that pays – testing hero vs. long emails, pop-ups, welcome series, and frequency
• List strategy, not list “cleaning” – optimizing engagement tiers without torching revenue
• Flows that convert – cross-channel trigger logic for email, SMS, and push (and what to skip)
• Personalization, debunked – why “best product + best landing page” beats rabbit-hole segments
• Content calendars that move inventory – using click maps and product sell-through to plan
• KPI “love languages” – aligning goals (LTV, repurchase rate, churn) so teams row the same way
• Escaping the AM/PM treadmill – frequency tests that trade short-term blasts for durable growth
• Agency vs. in-house – when speed and bandwidth matter more than another standing meeting
Plus: Marina explains the “test fast, then go wide” BFCM play, Eric confesses his hatred of over-personalized welcome flows, and Aaron lobbies for inbox placement over deliverability vanity metrics. 📨
👥 Meet the guestsMarina Carroll, Retention & Lifecycle Lead at New StandardEric Rausch, Co-founder at New StandardHost: Aaron Schwartz — Co-founder & Co-CEO, Orita.ai
🎧 Chapters[00:00] Meet New Standard: Who We Are & Why We Win[02:57] Retention, Reloaded: What’s Changed (and What Still Works)[05:49] Weird Roads to DTC Glory: How We All Got Here[08:27] The Gap We Saw—and Built New Standard To Fill[11:15] First 30 Minutes: Read the Room, Then Move[14:20] Hiring Killers: How We Build a Team That Ships[17:09] BFCM Warm-Up: What to Start Testing Now[20:12] Test Smarter: Subject Lines, Timing, and “Shorter Wins”[22:53] Send Wide, Not Wild: Engagement Tiers for BFCM[26:15] List “Cleaning”? Nah. List Optimization That Prints Money[30:37] The BFCM Playbook: Who Gets What, When[36:00] Flow State: Email + SMS (+ Push) That Actually Sync[40:10] KPIs as Love Languages: Align, Then Scale[47:04] Agency or In-House? Choose Speed, Not Ego
🌐 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
In this episode of The Orita Podcast, Aaron Schwartz sits down with two operators who’ve seen inside dozens of Shopify brands: Dov Quint (OpenStore, ran storefronts for ~50 brands) and Caleb Madsen (Fractional CMO). Together they cut through AI hype, agency roulette, and bloated tech stacks to show what really moves the needle.They discuss:• Founder obsession is better than shiny tools — why focus beats feature creep every time• Fractional done right — when to bring in help, when you just need a great media buyer• “Chaperoning” your stack — how to vet vendors, negotiate, and stop paying for apps you don’t use• Managed service vs. self-serve — why software still needs humans to unlock value• Practical AI wins — using fewer tools to 1.3x output without 10 new platformsPlus: Dov explains why you shouldn’t try to learn every AI tool at once, and Caleb makes the surprisingly profitable case for being “boringly excellent” at the basics.👥 Meet the guests• Dov Quint — E-commerce operator; Storefronts at OpenStore• Caleb Madsen — Fractional CMO, Madhouse Consulting• Host: Aaron Schwartz — Co-founder & CEO, Orita.ai🎧 Chapters[00:00] Meet the Operators: From Polaroid to 50 Shopify Brands[06:15] From Support Tickets to Ad Spend: Caleb’s Leap to Marketing[09:57] Founder Obsession: The One Moat You Can’t Outsource[15:45] Fractional CMO, Real Talk: When You Need One (and When You Don’t)[21:13] E-commerce Reality Check: What Actually Moves the Needle[26:44] Relationships are greater than Tactics: How “Chaperones” Save Your P&L[27:53] Tech Stack Triage: Cut the Bloat, Keep the Winners[29:22] Tool Picking 101: Vendor Vetting Without the Hype[31:47] Stack Optimization: Turn Subscriptions Into ROI[33:32] Stop the Agency Roulette: Finding Fits That Actually Perform[36:17] AI Without the Buzzwords: One Tool, 30% More Output[44:28] Dear Founders: Simple, Profitable, Boring (Why That Wins)[49:15] The Wrap: Where to Find Dov & Caleb🌐 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
In this episode of The Orita Podcast, Aaron Schwartz sits down with three leaders rewriting the playbook for direct mail: Ben Walter (CEO of PostPilot), Jess Chan (Founder of Longplay), and Ben Semmar (GM of Direct Mail at Orita). Together they unpack how brands can turn an “old-school” channel into a modern profit engine for BFCM and beyond.They discuss:• Direct mail myths – why it’s not just for lapsed customers, and how it lifts all channels• Precision beats spray – segmentation, timing, and why thoughtful targeting wins in a channel with higher stakes• Building the right process – testing cadence, creative learnings, and avoiding cookie-cutter playbooks• ROI you can’t ignore – 2–3x LTV lifts, inbox deliverability boosts, and how Direct Mail + email/SMS compoundPlus: Jess explains why “one segment, one offer, one test” beats template-chasing every time, and Aaron tries to convince everyone that snail mail is the original push notification. 📬👥 Meet the guestsBen Semmar, GM of Direct Mail at Orita.aiJess Chan, Founder of Longplay BrandsBen Walter, Partnerships at PostPilotHosted by Aaron Schwartz, Co-founder & Co-CEO at Orita.ai🎧 Chapters[02:31] Busting the Biggest Direct Mail Myths[15:52] Why LTV Is the Real KPI[21:36] Direct Mail: Your BFCM Cheat Code[25:01] Plays That Actually Win with Direct Mail[31:48] How to Test Without Burning Cash[41:16] From Postcards to Catalogs: Picking Your Weapon[46:03] Quick Wins to Nail Direct Mail Fast🌐 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 segmentation intel
In this episode of The Orita Podcast, Ovadia Labaton (co‑founder of The Perfect Jean) and Sammy Tran (founder of BMO Media) break down how they mix data discipline with a brand voice that never plays it safe. From cash‑flow math to irreverent copy, they show why great denim + great data still beats blitz‑scaling every time.
They tackle:
Unit‑economics first, always – breakeven ROAS, cash‑turn cycles, and building a “fortress” balance sheet
CX as a profit lever – refunds, radical honesty, and the small service touches that turn one‑timers into evangelists
Email that entertains and converts – pacing vs. batching, timing vs. templates, and why engagement is a curve, not a switch
Scaling past $10 M – team dynamics, profit targets, and resetting the goalposts from scale-at-all-costs to durable, cash‑flow growth
Stick around for when Aaron’s “Spanish castle” tour gets factchecked. 🏰🤔
👥 Meet the guests
Ovadia Labaton, Co-Founder, The Perfect Jean
Sammy Tran, Founder, BMO Media
Hosted by Aaron Schwartz, Co-founder & Co-CEO at Orita.ai
🎧 Chapters
[01:51] From BlackRock to Bootstrapped: a Wall‑Street escape plan
[06:43] Birth of The Perfect Jean: stretch denim meets savage copy
[09:16] Cash‑Flow or Bust: unit‑econ rules you never break
[11:14] CX That Sticks: turning one‑time buyers into brand lifers
[16:08] Inbox Stand‑Up: writing emails people want to open
[22:07] Right Message, Right Minute: timing beats discounting
[25:35] Let the Robots Segment: automations that print money
[29:07] Tech‑Stack Chess: picking partners, not plug‑ins
[30:40] Build‑With > Build‑For: inside a vendor love story
[34:58] Loyalty 2.0: memberships, points, and repeat magic
[37:36] Small Crew, Big Output: culture that keeps jeans flying
[40:16] Founder Playbook: three things to stop doing today
[42:54] Success That Counts: cash beats vanity metrics
[46:40] Fresh Eyes on Email: why diversity trumps “best practices”
🌐 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
When Tina Bou‑Saba talks consumer strategy, the smartest founders start taking notes.
In this episode of The Orita Podcast, we talk with Bou-Saba about how she helps founders navigate high-stakes decisions, from product pivots to capital strategy. We also dig into the biggest opportunities in consumer, the trends shaping where capital is flowing next, and the lessons she’s carried from Harvard to Wall Street to today’s boardrooms.
They tackle:
The one trait every breakout founder shares (spoiler: it’s not an MBA)
Brand versus product: why “cool” is useless without a value‑capture engine
A back‑of‑the‑napkin framework for knowing if your pricing (or fundraising) math actually works
If you’re building, funding, or obsessing over consumer brands, hit play and let the strategy session begin.
👀 Stick around to the end—Aaron gets some skincare advice.
👥 Meet the guest
Tina Henry Bou-Saba Consumer Investor | Founder at CXT Investments
Hosted by Aaron Schwartz, Co-founder & Co-CEO at Orita.ai
🎧 Chapters
[00:00] Intro & why Tina’s been stalking consumer behavior since the Abercrombie era
[04:43] Brand love vs. product lust—how to build both
[09:18] The one Harvard list every entrepreneur should tattoo on their laptop
[14:26] B2B vs. B2C founders: different planet, different playbook
[24:37] Credibility hacks: signals that make retailers (and investors) swipe right
[27:31] Public‑facing founders + ops pros = the modern power duo
[30:38] Saying “no” to the 500‑door rollout (and sleeping at night)
[35:57] Beauty’s knife fight: saturated, profitable, still worth it—if…
[39:48] Wellness, women’s health, longevity clinics: the next growth galaxy
[48:26] Tina’s north‑star advice: sell products or it’s just an art project
🌐 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
In this episode of The Orita Podcast, Aaron Schwartz sits down with Ben Parr—Mashable alum, best‑selling author of Captivology, co‑founder of Octane AI, and now investor at Theory Forge—for a founder‑to‑founder reality check on how commerce tech is moving (hint: faster than your Monday stand‑up).
Together, they unpack:
The $$$ unsubscribe—how to show the C‑suite that every send is either compounding value…or torching it
Zero‑party data, real‑party money—how quizzes became Octane AI’s unfair advantage
Investor X‑ray vision—the scoring prompts Ben runs through GPT‑4o before wiring a pre‑seed check
Founders, don’t die—Ben’s surprisingly simple rule for surviving platform cliffs, cash crunches, and chatbot scandals
Building 10M ARR in a weekend—and other tales from the AI frontier you can’t ignore
If you’re a DTC operator, tech founder, or anyone still calling ChatGPT “the robot,” this convo will either supercharge your roadmap or light it on fire. Either way, time to move.
👥 Meet the guest
Ben Parr, Co-founder at Octane AI
Hosted by Aaron Schwartz, Co-founder & Co-CEO at Orita.ai
🎧 Chapters
[03:55] Octane AI glow‑up: from chatbots to checkout mind‑readers
[07:48] Betting on silicon brains: how I pick AI winners
[12:37] Let the algorithms argue—then I sign the check
[16:24] Brand flex: real‑world AI wins you can steal
[20:27] Tomorrow’s checkout: voice, vision, zero‑friction everything
[24:18] Founder survival kit: grit, group chat, radical transparency
[27:51] Parting shot: build with empathy or get automated
🌐 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