When Kashish Gupta declined a return offer from Bessemer Venture Partners in 2018, he had nothing more than an idea— a Slackbot for travel. But what he lacked in product clarity, he made up for in conviction. A year later, that early concept, then called Carry Travel, found its first backer in Dorm Room Fund.
At the time, Adele Li and Toni Oloko were student investment partners at DRF— and the point partners on Gupta’s deal. Li had studied with him at Wharton and remembered late-night study sessions that doubled as startup vision quests. “He’s been literally crashing on couches for three months while building this product,” she wrote in her notes at the time. “I think he’s incredibly strong technically and I don’t doubt his ability to execute.”
Oloko was similarly bullish. “A top 1% team,” he noted, citing their polish and drive. And while he had flagged concerns about Carry Travel’s unit economics— a caution that would prove prescient— the promise of the team outweighed the risk of the model. DRF wrote a $20,000 check.
Gupta used the money to buy a new MacBook and book a one-way flight to San Francisco.
There, he moved into a group house with Tejas Manohar and Josh Curl, both engineers at Segment, a leading customer data platform. Oloko later described Manohar as “one of the most prolific young engineers in Silicon Valley at the time.” Gupta recruited Manohar to join him full-time. Curl, also in the midst of pivoting his own startup, soon followed.
With the founding team in place, the group entered what Gupta would later call “pivot hell.” They cycled through six concepts— two travel ideas, a Slack-based customer service platform, and customer dashboards— before finally landing on reverse ETL as their wedge into the market. That final pivot became Hightouch.
“They were just super young and hungry,” Oloko recalled. “You could just feel the hunger.”
Today, Hightouch is a leader in the modern data stack, helping teams sync data directly from their warehouses into the tools their business teams use. The company is now one of the fastest-growing platforms in the composable CDP space— and a breakout DRF unicorn.
Kashish Gupta, Hightouch co-CEO, in conversation with Molly Fowler, Dorm Room Fund GP— February 2025.
Li, now on the business team at OpenAI, reflects on the original bet with confidence. She believes that if Gupta launched Carry Travel today, he would have been able to leverage artificial intelligence to “transform travel research, transparency, and end-to-end bookings— further enhancing a core element of Carry Travel’s initial value proposition.” But she never doubted the team’s potential. “They were determined from the start to create something that truly mattered to their customers. As their industry— and their stakeholders— evolved, so did they. That transformation required a willingness to evolve, even when things were going well.”
Oloko, now the co-founder CEO of his own unicorn, Dandy, shares that conviction. “I’m super happy for them,” he told DRF, “and I hope they continue to do great things.” He added, “Their success also gives me even more conviction that students at a young age can identify amazing outliers.”
At Dorm Room Fund, that’s exactly what we’re here to do: back extraordinary student and recent alumni founders— sometimes before you even see the full potential yourself. If you’re building something ambitious and early, we want to meet you.
He then underscored not only the outstanding caliber of the Hightouch team but also the strategic promise of investing in young talent. “They’re just great. Their success also gives me even more conviction that students at a young age can identify amazing outliers.”
Pitch Dorm Room Fund and let us be your first yes.
Written by Head of Editorial Aaron Anandji.
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