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.
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