Why start Pressbox in Chicago?

What if the best startup isn’t sexy at all? In 2013, Vijen Patel left private equity to pursue “the least-worst idea”: dry cleaning. No patents. No app wizardry. Just laundry lockers in high-rises, ruthless unit economics, and a $1.99-a-shirt price that was seared into America’s brain.

From bootstrapping routes at 5 a.m. to breaking even in 6 weeks, Vijen and co-founder Drew McKenna scaled Pressbox to hundreds of locations, stared down well-funded competitors, and ultimately sold to Procter & Gamble, where Pressbox became Tide Cleaners (now ~1,200 locations). After the exit, Vijen launched The 81 Collection, a VC fund backing “boring” businesses that quietly power the economy.

This episode is a masterclass in building profit first, creating user behavior (not changing it), and protecting customer retention like your life depends on it.

What you’ll learn:

• How the “least-worst idea” found product-market fit
• How sidestepping rent + labor can flip margins from 15% to ~40%
• The efficiency insight that beat “Uber-for-X” rivals
• The new-residence edge: creating customer habits with a welcome-kit
• Why Pressbox had to set crazy-high retention goals (98%!)
• How to keep competitors close—and turn a Goliath into your buyer
• The post-exit premise: “boring” businesses are engines of the middle class

Timestamps:

• Choosing dry cleaning with a private equity lens: don’t do it for passion–focus on practicality — 00:09:30
• The SMS “app”: low tech, high convenience — 00:14:14
• Unit economics breakthrough: lockers (26 transactions per hr) versus scheduled pickup (4-6) — 00:18:55
• The $1.99 insight: a price everyone expected — 00:24:58
• How getting into Chicago’s top high-rise was a game-changer — 00:31:11
• Margins that work: if you’re a high-rise “amenity,” you don’t pay rent — 00:33:08
• Competing with Washio: convenience wins — 00:39:07
• Vertical integration: building the plant, staffing via Spanish newspapers — 00:41:48
• P&G looms: head-to-head, then the acquisition dance — 00:51:25
• Burnout, trade-offs, and life after exit: launching a VC fund that specializes in boring businesses — 01:03:28

This episode was produced by Alex Cheng with music composed by Ramtin Arablouei. It was edited by Neva Grant with research help from Olivia Rockeman. Our engineers were Patrick Murray and Maggie Luthar.

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