The landscaping biz that got a young Jake Stein in trouble with the local postmaster - Technical.ly Philly

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Mar. 3, 2017 11:59 am

The landscaping biz that got a young Jake Stein in trouble with the local postmaster

Welcome (back) to Lemonade Stand, our column about Philly entrepreneurs' first businesses.

Stein's new landscaping crew.

(Courtesy photo)

Every entrepreneur has to start somewhere. In Lemonade Stand, we profile a local entrepreneur’s first venture or job. Tell us about yours.


Though you may know Jake Stein as RJMetrics cofounder and Stitch CEO, there was once a time when he wasn’t leading what we called one of the region’s hottest startups.

“I started a landscaping company in high school,” Stein recalls. “I made up flyers with impressive taglines including: ‘Cheaper than people who overcharge’ and ‘Keeping teens off the street and in your yard.'”

Stein says he drove his mom’s minivan slowly along the side of the road while a friend stuffed said flyers into mailboxes. But there was something a bit shady about this marketing tactic.

“Turns out it’s illegal for anyone besides the postal service to put something in a mailbox. By the time I got home there was a message waiting for me from the local postmaster that if I didn’t cease and desist they would press charges,” Stein remembers in an email.

However, the 16-year-old had already generated enough leads to keep him mulching and weeding for the next two summers.

“It was totally worth it,” said Stein.

(Meanwhile, Stein’s cofounder Robert Moore also had an interesting teen venture going on. Spoiler alert: it involves cheeseteaks.)

To hear more about Stein’s business war stories, see him at #Failfest during Philly Tech Week 2017 presented by Comcast on May 4.

People: Jake Stein
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