Having heroes is great, but let's be honest, looking at the great accomplishments of some the business leaders you most admire can also be pretty intimidating. While contemplating the likes of Elon Musk and Steve Jobs might remind you that it's possible to achieve great things, it might also inadvertently make you feel like you could never manage to travel from where you are now to anything nearly so impressive.

What's needed is a counterweight to those people's currently gold-plated résumés, a reminder that however mind-blowingly accomplished they may be today, they started out in some pretty humble circumstances.

That's why a recent Twitter conversation kicked off by Homebrew Ventures co-founder Hunter Walk is so valuable. The well-connected investor took to his account to solicit CEOs and other startup-scene notables to share their first jobs ever. What kind of responses did he get? Forget top-tier internships and impressive entry-level gigs. Some of the best-known names in startups had some pretty terrible first jobs.

  • LinkedIn CEO Jeff Weiner started his working life “shoveling snow off driveways” and “delivering newspapers.”
  • Square CFO Sarah Friar worked on her “Uncle Louis’s farm. Six a.m. wakeup ‘to pick stones off the mountain field.’” She has relatively fond memories of the gig, though. “I’d do it again!” she said.
  • Foundry Group partner Brad Feld began his career “knocking down wasps nests and throwing out the trash at my tennis club. I got fired within a month.”
  • Nest CEO Tony Fadell was apparently always entrepreneurial. He “started an egg-delivery business in third grade, then a paper route in sixth. Learned a ton ... ”
  • Etsy CEO Chad Dickerson was another childhood go-getter. He says he had a “good old-fashioned lawn-mowing biz with brother. I was 8, he was 12. Had 25-plus lawns. Had computerized billing. In the early '80s.”
  • Sarah Tavel, a partner at VC firm Greylock, “went door to door in NYC soliciting donations for NYPIRG. Pure commission based--made 28 percent of what I raised.”
  • Code for America founder Jennifer Pahlka was a “security guard at a med school!" She worked the nightshift from midnight to 8 a.m.

Besides simply satisfying our curiosity about the early lives of founders and investors, Walk's exercise in early-career nostalgia can probably teach aspiring entrepreneurs a few things. First, as Friar's and Fadell's responses make clear, every job is a learning opportunity, no matter how menial. Second, as Dickerson and Fadell demonstrate, it's never too early to start exercising your entrepreneurial muscles, and finally as Feld's experience shows, early failure need not predict your career trajectory (it just might be a sign you don't like stinging insects).

Published on: Sep 11, 2015
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