Our Investment in CloudTrucks

kanyi maqubela
kindred ventures
Published in
3 min readDec 16, 2020

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I found myself getting emotional watching this video:

As I watched it, I thought, help is on the way. The pandemic has made the fanciful feel real. A sense of surreality shapes what has otherwise been mundane –– in this case, trucks pulling out of a warehouse to deliver goods. I found myself zooming in, wondering who those drivers were, historic in their role, delivering the first batch of the vaccine for the most fatal pandemic in a half century. Bonnie Brewer, of Boyle Transportation, was one of those drivers. She has spent thirty years driving trucks back and forth across the United States, specializing in pharmaceutical products including chemotherapy drugs, cold-chain products, and, now, the COVID-19 vaccine. Reuters reported her saying: “It feels amazing” as the fleet owner, Andrew Boyle, said “Today, we’re not hauling freight, we’re delivering hope”

More than 3.5 million people work as truck drivers in the United States: 1 in 40 working-age people in this country is a truck driver. Truck freight has grown into the capillaries of our economy, and is making steady gains toward becoming the arteries, as well. Truck freight is an $800B economy in the United States. It is, increasingly, how we get our stuff. And it is essential work. And during a pandemic, essential work is consecrated. It is heroic.

Many (and growing) truck drivers are independent truckers, known as owner-operators. This group are small business owners, who have to think about insurance, revenue optimization, taxes, cashflows, and technology vendors. To-date, their work has not been adequately considered by technology innovation. To go it alone in this work has meant to be alone. Enter Cloudtrucks. As the largest taxi company in the world has no taxis, the largest hotel chain has no hotels, the largest trucking company, they believe, will have no trucks. But it will have everything else.

What does this mean for the independent truck driver in this now increasingly software-driven network? In a few short months, the Cloudtrucks team developed best-in-class technology that collects real-time load data from UberFreight, Loadsmart, Convoy, and others, and allows an independent truck driver to optimize their loads on the basis of revenue, geography, and personal preferences.

A truck driver can spend more time with their family and drive more revenue per haul using this technology. Small fleet and owner-operators can compete with large fleets on optimized routes, can negotiate bulk rates on leasing and buying rigs, and can maintain the autonomy and independence that has proven to be a durable benefit. Since launch this spring, the company has grown at an incredible organic clip, demonstrating the latent need for technology in this critical small business market. With CT Cash, which they announce this week, a rider can can balance their books on the Cloudtrucks platform, spend with a CT debit card directly from their hauling revenue and can receive instant payments, which stands to change the workflows, and the lifestyles, of hundreds of thousands of truck drivers in the country. Everything is fintech, indeed.

Tobenna, Jin, and George, hailing from Opendoor, Zenefits and Intercom, have assembled a remarkable team, based in the California and Texas, and they continue to hire and ship product at one of the fastest rates I have ever seen. We were thrilled to be an investor in their seed round, and we are excited to continue to support them and welcome Caffeinated Capital with this new financing. I can’t help but think: help is on the way.

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