In this episode of The Orita Podcast, Aaron Schwartz sits down with Michael Epstein. Michael spent 25 years in ecommerce fixing what he calls nine-figure brands losing eight figures. The tool that kept working when nothing else did was the postcard.

• Why turnarounds taught him that most struggling brands do not need magic, they need blocking, tackling, and a culture where people actually understand the numbers

• The thesis behind PostPilot: every digital channel gets more crowded and expensive over time, while the mailbox gets emptier and postage stays capped

• Two years of people laughing at direct mail, and the iOS 14 moment that changed everything

• The acquisition AI story: an identity graph covering essentially every US household, and why data beats the old data-broker model

• The biggest testing mistake brands still make, and why Black Friday is the worst possible time to try a new channel

• Aaron on the subscriber fallacy: why being on your email list does not mean email is what moves someone to buy

👥 Meet the guest

Michael Epstein, Co-Founder and Co-CEO at PostPilot

🎙 Hosted by

Aaron Schwartz, Co-Founder and Co-CEO at Orita.ai

🎧 Chapters

[00:00] Michael Epstein: 25 Years in Ecommerce, Two Co-CEOs

[01:19] Nine-Figure Brands Losing Eight Figures: The Turnaround Years

[02:20] The Spreadsheet Problem That Sparked Klaviyo for Direct Mail

[03:55] Most Broken Brands Just Need Blocking and Tackling

[08:54] Walking Every Employee Through the P&L

[11:01] OKRs: Imperfect, Necessary, and Better Than Rowing in Circles

[12:47] What Michael Misses About the Brand Side and What He Does Not

[15:03] We Are the Customer: How Empathy Built PostPilot

[17:29] The Law of Shitty Click-Throughs and the Capped-Cost Mailbox

[19:31] Two Years of Being Laughed At, Then iOS 14 Hit

[21:24] Shopify and Klaviyo: The Integrations That Changed the Channel

[22:33] Do Not Test Direct Mail on Black Friday

[26:19] Why Brands Test Meta Seriously and Direct Mail With Pocket Change

[29:04] Acquisition AI: An Identity Graph of Every US Household

[32:08] What Is Next for Direct Mail

[35:43] The Subscriber Fallacy: Email Signup Does Not Mean Email Converts

[38:46] Take Off the Marketer Hat, Put On the Consumer Hat

🌐 Check out Orita.ai for more episodes of The Orita Podcast, where we sit down with the most interesting operators, marketers, and founders in e-commerce to talk about what’s working right now. Hosted by the Orita team. Orita uses machine learning to help brands send smarter, more profitable marketing, by figuring out who actually wants to hear from you and when.

🚀 Get your free email audit from Orita, turn segments into superpowers: https://orita.ai

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