In A Pinch

Ep 6: Michael Rasile


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Michael Rasile — touring drummer turned fan-experience leader at Front Row and partner at Ceremony of Roses — joins Arthi and Jayan to talk about what really happens inside the war room when a major artist drop goes live. He walks through the Harry Styles drop that "looked like a roulette machine," the trade-off between blocking freight forwarders and protecting Billboard chart eligibility, why the line between a super-fan and a fraudster is razor-thin, and the under-discussed rise in chargeback abuse he believes is being fueled by AI cynicism toward the internet.
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SHOW NOTES
Guest: Michael Rasile Founder & Director of Customer Experience, Front Row Partner, Ceremony of Roses (Sony Music)
Hosts: Arthi Rajan Makhija & Jayan Tharayil, Cofounders, Pinch AI

In this episode we cover:

  • How a touring musician ended up running merch ops for some of the world's biggest artists
  • Why he calls his work a "fan experience" company, not a customer experience one
  • What a typical day in the life of artist merch ops actually looks like (spoiler: a lot of "hurry up and wait")
  • The Harry Styles drop that he says he'll "never forget as long as I live"
  • The "freight forwarder belt" (Florida, Delaware, Oregon) and the trade-off between blocking resellers and protecting Billboard chart position
  • Why the line between a super-fan and a fraudster is razor-thin — and the fiduciary duty Michael feels to get the call right
  • The chargeback feature he wishes Pinch would build next (and the alpha we're already cooking)
  • His craziest fraud story: 50,000 $10 t-shirt orders in five minutes, on the weekend of his mom's 60th birthday, during COVID
  • The behavior shift he's seeing in chargeback abuse and why he thinks AI cynicism is partly to blame
  • His three-pillar playbook for any ops lead taking over an artist e-commerce drop with no fraud tooling
  • If you operate, protect, or build for any high-velocity e-commerce business — not just music — this one is worth your 40 minutes.
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    CHAPTERS:
    00:00 Intro — meet Michael Rasile
  • 02:06 From touring drummer to merch ops: the pandemic pivot
  • 05:31 Both sides of the merch table — building a fan experience company
  • 08:11 A day in the life of artist merch operations
  • 10:49 Inside the war room when a drop goes live
  • 13:30 The Harry Styles drop: "like watching a roulette machine"
  • 15:09 Freight forwarders vs. Billboard chart eligibility — when to cancel, when to let it ride
  • 19:10 What "good" looks like with Pinch: protecting the super-fan
  • 22:41 Closing the loop — the chargeback feature Michael wants next
  • 25:28 Lightning round
  • 25:50 Craziest fraud story: the $10 tee Billboard fiasco
  • 30:11 What keeps him up at night — chargeback abuse and the AI trust gap
  • 34:09 Advice to a new ops lead with no fraud tooling
  • 38:36 About Front Row
  • 40:14 Wrap

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KEYWORDS
artist merch, music merch, e-commerce fraud, freight forwarders, chargeback abuse, fan experience, super-fan, bots at checkout, drop protection

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