Finding Hidden Gem: A Lesson from Craigslist

Hiring has always been my biggest challenge. Assessing fit for co-founders and early employees felt like a daunting task. However, there was one area where I found consistent success: hiring delivery drivers for my fruit business.

In those early days, I handled most of the morning delivery routes myself, hustling across downtown Chicago in my trusty 2004 Passat hatchback, confronting my anxiety about parking tickets one delivery at a time. As we expanded to three delivery days per week, I realized I needed reliable drivers who could not only deliver the fruit on time but also set up arrangements for social events and maneuver the tricky Lower Wacker Drive.

Finding candidates with that full skill set proved unexpectedly tricky. My expertise in hiring was frankly limited back then. So I did a series of trials and errors. Some memorable ones are listed below:

I explored the typical hiring channels. Online job boards and freelancer platforms yielded candidates who either ghosted interviews or quit midway through training routes. Ouch! Even on-campus postings had their quirks, like the day someone drove a luxurious Mercedes to the warehouse, mistaking the posting for a summer internship opportunity. Talk about a mix-up!

Referrals from other urban farming communities seemed promising at first until I realized that I could not meet their expectation of a 5-day-a-week schedule and the requirements on the company vehicles. We simply couldn’t afford it yet.

I tried recruiting independent Uber drivers, assuming their flexible gig schedules could align with our 3 days a week schedule. However, the rideshare crowd heavily preferred more flexible schedules (2 hours per day) and night shifts. No wonder my Uber ratings weren't exactly five stars.

In a bit of desperation, I even proposed a partnership with a local composting service, hoping they could help deliver fruits while wheeling in fresh, office-size compost bins for clients. But then I imagined our fresh produce sitting in a van filled with the compost bins they wheeled out from the office. I realized I'd be facing numerous food safety violations. That idea was dead on arrival.

Feeling stuck in a hiring rut, I made a big move: investing a hefty $50 to post on Craigslist. To my surprise, I immediately heard back from two candidates! They were nothing like what I expected, but they turned out to be more qualified than anyone else I’ve interviewed.

Two days later, we welcomed Patrick, who proved transformative for our small team. Not only did he boast years of delivery experience, dashing through upper/lower Wacker like a champ, but he also brought an incredible attitude. His passion for performance art helped him approach each route as a kind of "on-the-road show" aimed at delighting customers. He owned the role fully and even provided thorough transition notes as he eventually moved on to music full-time.

Tapping into channels like Craigslist opened the door to an overlooked pool of passionate, self-motivated hustlers who were truly stoked to contribute in unconventional ways. They appreciated small wins like the joy from our customers' reactions, and savouring the uninterrupted "flow state" of being on the road. I was glad that my proudest delivery moments - seeing customers' excited faces as fresh fruits arrived - became sources of motivation for them as well.

I hope this post can serve as a humble tribute to exceptional individuals like Patrick Connelly and Laura Mazzenett who embodied that craftsman spirit. It is their drive to genuinely enjoy the craft and process itself that made the early days of the venture possible. Thank you for having shared the journey with me.