In March of 2013, David Chait was a student at Columbia Business School, and his vacation-planning startup Travefy had been hatched the year before. Even so, what with juggling school with product development, Travefy had yet to earn its first dollar. Chait had recently pitched the startup to the head of Columbia’s entrepreneurship group, a young man named Rich Liang, who had informally agreed to try out the tool in planning a spring break trip for the group.
In the weeks before spring break, just about everyone else at Columbia camped out at Butler, the main campus library. Whatever the poet may have said, on a college campus March is the cruelest month, the month of midterm exams and pre-break papers. Many students had basically camped out. "I’ve literally seen pillows and sleeping bags," Chait recalls.
Chait had settled into his desk on the fourth floor, in what he describes as a Hogwarts-esque room with an atmosphere of "quiet and stress and working." Chait was himself hard at work when his iPhone started vibrating: an unknown number. Contrary to library protocol, Chait answered it—he had to.
"Hello, this is David," said Chait (who is the first to admit he is not the quietest talker).
"Hi David, this is Rich." Chait’s heart leapt.
But then Rich went on to explain that he was experiencing a problem with Travefy (which was then in what Chait calls "pre-beta"). Liang had been able to use the tool to organize a vote on where to go—SXSW, it was decided—and to execute a useful search of hotel options in Austin. But Travefy lacked a button to easily navigate back to the original search landing page, in order to compare prices. Was Liang missing something? Could this be fixed? "If not, then the product was great for voting," said Rich. "But I can’t book through it." Which would mean no revenue for Travefy on the deal.
"Thanks so much for using the product," gushed Chait. Around him, a few students had already lifted their heads to give what Chait recalls as "death stares." Chait went on: "Please bear with me. Let’s figure this out."
"We’d love to work with you," said Liang. "But we have to book this now."
By now the "death stares" had grown to a chorus of shushes, and finally someone urged Chait to get out of the room. Chait took a quick mental inventory of his options. From the fourth floor of Butler you'd have to get on an elevator to get outside in a timely manner, but he'd risk losing his cell phone connection in there. Chait and Liang weren't friendly enough for Chait to ask to call back in 10 minutes. "This was as institutional a sale as any other," recalls Chait. If he was going to make this sale, it had to be right there, in the library.
Chait walked out into the hallway, as he began to troubleshoot Liang’s problem. Chait knew his team had screwed up: they’d have to make a button to easily navigate back to the original search landing page. But that was a patch for future customers, not this one. In order to get Rich what he needed immediately, Chait had to get creative.
Suddenly, the idea came to him. "Rich, could you read me the full URL you’re looking at?" Chait asked.
Liang rattled off a long string of numbers and letters. Since Chait was intimately familiar with the structure of the URLs related to his site, he was able to identify Liang’s "trip ID" from the URL. That trip ID then became the code through which Chait was able to have Liang manually navigate back to the search landing page and any other pages Liang wanted to visit. "I was reciting URL hierarchies from memory," recalls Chait with a laugh. "I was literally explaining our domain structure."
There was just one problem: the library was so crowded this time of year that students had turned the hallways into workspaces, too. And no one was keen on hearing Chait recite those URL hierarchies when they were trying to solve a calculus problem or write that Kierkegaard paper. Chait thought that in leaving the quiet room, he had done his best, and students around him would cut him some slack. "But I quickly realized from the individuals around me that that wasn’t going to cut it." Those death stares and shushes started surfacing again.
"So at that point I got up and literally just started walking around." The way the library was structured, he had to cut through crowded room after crowded room. At least now, as he moved from room to room, he was conducting his continual escape from the people he was irritating. "My heart was about to explode, it was so stressful," recalls Chait.
Chait finally reached a dead-end: the far end of a hallway. Yet there, too, students began shushing him and demanding he get off the phone. "The funny part was that the noise they were making was impairing my ability to have the call," recalls Chait (who also affably admits "I may be the villain of this story.")
Then, Chait saw the doors to a stairwell. It would be an echo chamber, but it was his last hope.
Chait stepped into the stairwell to round out what he hoped would be the last, smooth minutes of the call. But at that point, Chait heard the worst thing he could possibly hear from Liang, who had settled on a hotel that interested him.
"He said, ‘I think I’ve seen this cheaper somewhere else.’"
If true, this was bad news indeed. If Travefy wasn’t serving up the best deals, then the product wasn't offering value to its users. Chait might have simply talked over Liang or insisted he was wrong. But Chait had faith in his own product.
"You may be right," he said. "But why don’t we click through to check?" Some sites might appear to have lower rates, he reasoned, but that’s just because they wind up tallying taxes at the last minute in checkout.
"There was a huge fear," Chait admits, as he decided to call his competitor's bluff.
Chait was right. The competing site that seemed to offer a lower price wound up gouging Rich with last-minute taxes and fees. Liang booked the Austin hotel, two rooms for seven nights. Chait thanked him and hung up.
Chait opened up an email notification on his phone: 14 room-nights (two rooms, seven nights) in Austin, Texas. $2,796.36.
"I was thrilled," Chait recalls. "I placed the two phone calls you make: one to my business partner and co-founder, Chris. And then to my other partner-in-crime: my now-wife, Amanda."
Chait looks back on the product he had a year ago and laughs. Since then, he and his team have relocated to Lincoln, Nebraska, "the Silicon Prairie," and have added feature upon feature, including an ability to manage any traveling group’s expenses. This month, Travefy adds vacation rentals on top of hotel listings, and launches a responsively designed mobile site equipped with a mobile expenses tool.
But the memory of that first sale, and other small milestones, keeps Chait going. "Building a company is five steps forward, three steps back," he says. That first sale was "a huge leap" and offered "a sense of complete joy."
And to think: that first sale was so perilously close to falling apart.
"Looking back now, that product was almost a joke compared to where we are now. But there are a lot of steps you have to take to build a great product. Those little victories are what sustain you."