The Story Behind My Investment In Onfleet

Yes, the company name is Onfleet, not “On fleek,” though they are actually are “On fleek” when it comes to providing platform services and routing infrastructure to the on-demand economy. I could bore you with stats such as powering volume growth at a 30% month by month rate (40% scheduled, 60% on-demand), or how they’re growing B2B revenues by 35% per month, but that’s par for the course these days in SaaS.

The interesting part of the story is how I met Khaled, the CEO, and how I came to invest in the company. @Rafer, for those of you who know, is a friend and tireless supporter of the early-stage companies he fosters. Onfleet is one of those. Back then, in April 2014, the company was called “Trak,” and the founders had recently left Stanford and started their entrepreneurial journey.

At the time, I was writing about the on-demand economy and making a few investments in companies like Instacart and DoorDash. Rafer figured I should meet Khaled, and while I liked him initially as a person (we had a great first conversation), I wasn’t sure I wanted to invest because I didn’t feel a personal connection to the company. My first impression was Khaled was too reserved, but I came to learn letter, I misinterpreted that first meeting. We stayed in touch after I said “no,” and in fact, we discussed this very point. It’s not an easy conversation to have, and who I am to make such judgments.

To his credit, Khaled heard me out and, despite that, asked me very nicely for help in getting the story, pitch, and details together — and so I did, as a friend. He responded really well, and over the next few weeks, we traded a ton of emails, texts, calls. Three months in, Khaled was rolling in his round, and he called me up again — asking me to come on board. Now, looking back, I was lucky I got a second chance to invest, and I took it. Khaled has really grown and matured as a technology and operations CEO, building a team of 10 and providing critical platform services as part of the on-demand stack — right in the middle of one of the biggest trends in consumer behavior we’ve seen.

What Onfleet focuses on and where they’re going, you can read about that in all the news today as they launch into the public sphere. For me, what I’ll remember about this investment is that the frenetic pace of seed often doesn’t afford an investor the chance to get to know someone over a period of time. With Khaled, I had that luxury of time and no pressure other than our mutual respect for each other — and I had a second chance to learn that while he may be reserved in person, he’s relentless in his own quiet way. As I mature as an investor and begin to change my own style, I will look back on how I got to know Khaled over time as a potential model for how I operate as an investor in the future.

Haystack is written by Semil Shah, and is published under a Creative Commons BY-NC-SA license. Copyright © 2018 Semil Shah.

“I write this not for the many, but for you; each of us is enough of an audience for the other.”— Epicurus