Ep. #50: Dhruv Gupta, CEO and Cofounder of Drumkit

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Jan 14, 2025

Dhruv Gupta, CEO and co-founder of Drumkit, an AI-driven workflow solution for logistics, shares insights from his journey studying transportation at Harvard. He candidly discusses his early business failures and the lessons learned. Dhruv emphasizes the importance of confidence in leadership, the intricacies of automating logistics processes, and the balance between technology and personal touch in customer relations. He also addresses the challenges of securing new business and the significance of transparency in building lasting client relationships.

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ANECDOTE

First Business Failure

Dhruv Gupta's first YC-backed venture was last-mile delivery optimization for bikes and scooters.
This venture ultimately failed due to the COVID-19 pandemic and internal disagreements.

INSIGHT

Learning from Failure

Dhruv learned that failure is a learning opportunity and not the end of the road.
His family's support encouraged him to try again after his first business failed.

ADVICE

Leading with Confidence

Lead with confidence and bring your team along, ensuring they feel involved and enthusiastic.
Acknowledge that big endeavors require resources and be willing to take risks if you have them.

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For the 50th episode of The Freight Pod, Andrew welcomes Dhruv Gupta, CEO and cofounder of Drumkit. Dhruv shares his journey from studying transportation planning at Harvard to founding Drumkit, an innovative AI-driven workflow solution for logistics companies.

In this episode, Andrew and Dhruv talk about:

Dhruv’s experience of dealing with failure — calling his first business a “faceplant” — and what he learned that he still carries with him today.
The importance of leading with confidence, especially through uncertain times.
How Dhruv and his team are building Drumkit to be a tool that “conforms” to customers’ processes — and with that, how he thinks about scaling his team internally to build faster and land more customers.
The biggest challenges the Drumkit team is having with securing new business and the unique qualities they’re bringing to the brokerage sales process.

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*** This episode is brought to you by Rapido Solutions Group. I had the pleasure of working with Danny Frisco and Roberto Icaza at Coyote, as well as being a client of theirs more recently at MoLo. Their team does a great job supplying nearshore talent to brokers, carriers, and technology providers to handle any role necessary, be it customer or carrier support, back office, or tech services. Visit gorapido.com to learn more.

A special thanks to our additional sponsors:

Cargado – Cargado is the first platform that connects logistics companies and trucking companies that move freight into and out of Mexico. Visit cargado.com to learn more.
Greenscreens.ai – Greenscreens.ai is the AI-powered pricing and market intelligence tool transforming how freight brokers price freight. Visit greenscreens.ai/freightpod today!
Metafora – Metafora is a technology consulting firm that has delivered value for over a decade to brokers, shippers, carriers, private equity firms, and freight tech companies. Check them out at metafora.net. ***