Home Why Reddit’s Founder was “Terrified” to Launch New Startup, Hipmunk

Why Reddit’s Founder was “Terrified” to Launch New Startup, Hipmunk

Five years ago, Steve Huffman was another young entrepreneurial mind chomping at the bit to launch his very own startup. After taking a train from Virginia to Boston to see Paul Graham speak at Harvard in 2005, Huffman and his partner Alexis Ohanian eventually joined the very first class of Y Combinator. Later that summer, Reddit was born. Now, in 2010, Huffman is taking a stab at his second startup, Hipmunk, and today I had the chance to chat with him about what he has learned from the last five years and why launching his latest project “terrified” him.

Reddit wasn’t even Huffman and Ohanian’s original idea. In fact, their idea for ordering food from cell phones was rejected by Y Combinator. Graham liked the pair so much, however, that he invited them back to try again with a new idea – a testament to the value of people over ideas. Huffman says this is “a mantra of Y Combinator,” as many companies change their original ideas several times.

Huffman’s newest venture, Hipmunk, aims to eliminate the pain and headaches that are associated with online flight searches, he says. No fancy algorithms or bidding on tickets – Hipmunk is just a simplified user-friendly interface for finding the best flights to get from point A to point B. Sometimes the best startup ideas aren’t entirely revolutionary new concepts, but are as simple as cleaning up someone else’s mess.

While his reputation has helped the startup secure funding from both Y Combinator and a group of angels including Ron Conway, Huffman says being a second-time entrepreneur also has it’s drawbacks.

“I almost threw up just before we launched because I had a lot more to lose in terms of reputation. I was terrified,” Huffman told ReadWriteWeb. “If you’re coming out of college, you’ve got nothing to lose. Whether you succeed or fail, you’re going to learn a ton, and you can only improve.”

Having previous experience and notoriety has certainly helped the company get off the ground, but Huffman says lessons and skills learned from his Reddit days have given the startup its greatest boost.

Reddit was originally coded using Lisp and launched on just a single server, he says. Switching to Python and getting the service to run from multiple servers was no small task, he adds. This time around, Hipmunk is “like Reddit version 6,” as it was built using similar Python infrastructures and launched on 16 servers, says Huffman.

“This project has gone a lot more smoothly that Reddit did,” he says. “I’m playing the same role as lead developer and product guy, but I’m a lot better at it than I was then. The development and deployment have both been a lot smoother.”

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