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.
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