“Someone’s always playing corporation games… we just want to dance here, someone stole the stage.” Starship’s iconic line from We Built This City could be an anthem for the travel industry, which has faced its own corporate games, disruptions, and rebirths over the last two decades.
The industry has evolved with a series of distinct entrepreneurial archetypes: from risk-taking “gamblers” to visionary “promoters” and now, to problem-solving “makers”. Each wave reflects the travel sector’s adaptation to new technological and economic landscapes.
Few people understand this evolution better than Chris Hemmeter, co-founder and managing director at Thayer Ventures, a venture capital firm specializing in the travel and hospitality sector. Speaking on stage at WiT Singapore last month, Hemmeter reflected on how the archetype of the travel entrepreneur has shifted with each generation.
“We went from gamblers to promoters to makers,” Hemmeter said. “The entrepreneurs that I see now are truly makers. They’re building stuff. They have insights into really unique problems that haven’t yet been solved.”
The Gambler Era: Risk-Taking Entrepreneurs in the Early Days of Travel Tech
In the early days of online travel, entrepreneurs were what Hemmeter calls “gamblers”. These pioneers took extreme risks to get their ideas off the ground. Lacking the support of a developed venture capital system, these founders often had no choice but to stake their personal assets on unproven business concepts. They went “all-in”, hoping to ride the first wave of digital transformation in travel.
“Entrepreneurs were gamblers,” Hemmeter explains. “They were all-in players. Venture capital hadn’t really developed yet, so these entrepreneurs would personally guarantee everything. It was all in with your personal net worth on every swing of the bat.”
Interestingly, he was being interviewed by fellow entrepreneur-turned-investor, Fritz Demopoulos who, with two co-founders, started Qunar as a meta search player in China in 2005 and made one of the most successful exits in the Asian online travel industry, when it sold to Baidu a few years after.
For these early players, launching a travel startup was a high-stakes game, often driven more by belief and ambition than by a structured strategy. Some succeeded spectacularly, like Demopoulos, but many more burned out, unable to keep pace with the costs and risks of scaling in an era when digital infrastructure was still taking shape.
The Promoter Phase: From Risk-Takers to Storytellers
As venture capital began to flow into the travel sector, the entrepreneurial archetype evolved from gambler to “promoter”. In this phase, it wasn’t enough just to be bold – you had to be persuasive. Promoters were charismatic visionaries who could tell a compelling story, attract investment, and inspire teams.
“Entrepreneurs were promoters,” Hemmeter notes. “They had to tell a story, sell a vision, build teams. The character of a fundable entrepreneur was someone who could truly promote.”
When prompted, Hemmeter called himself a “promoter”.
Asked why he chose to diverge from his family’s hotel legacy, instead focusing on entrepreneurship and investment in the travel sector, he said. “I have an insatiable appetite for curious new problems to solve. I’m the butterfly catcher. And so I love to sort of find those threads. I love to evangelize what I think is coming. I like to tell big stories.”
In the age of “promoters” and an era where ideas were valued as much as execution, entreprenerus’ primary skill was selling a vision that investors, employees, and customers could rally around. Promoters laid the groundwork for companies that would scale quickly, sometimes faster than their operational infrastructure could support. This phase produced several of the household names in travel tech, but also left behind a string of companies that couldn’t survive the pressures of rapid growth.
Chris Hemmeter: “I have an insatiable appetite for curious new problems to solve. I’m the butterfly catcher. And so, I love to sort of find those threads. I love to evangelize what I think is coming. I like to tell big stories.”
The Maker Era: Today’s Entrepreneurs as Builders of Solutions
Today, Hemmeter sees a new entrepreneurial archetype emerging: the “maker”. These modern entrepreneurs are not just focused on grand ideas or high-stakes risks; they are problem-solvers who prioritize building real, sustainable solutions. Makers are product-driven, leveraging technology to create more capital-efficient businesses that address specific pain points within the travel industry.
“The entrepreneurs I see now are truly makers,” Hemmeter says. “They’re building stuff. They have insights into unique problems that haven’t yet been solved. They sometimes will think, ‘Well, why hasn’t somebody tried it that way?’”
Unlike the gamblers and promoters before them, makers are often deeply involved in the technical aspects of their products. They are passionate about crafting solutions, and they focus on refining their offerings to address real customer needs.
However, Hemmeter cautions that while makers excel at product development, they can sometimes overlook the challenges of go-to-market strategy – a critical aspect for scaling.
The Importance of Balancing Product and Market Strategy
Hemmeter emphasizes that a strong product alone isn’t enough for a startup to succeed. While today’s makers are highly skilled at building, they must also develop a clear strategy for reaching their market.
“Makers are product-driven, and they sometimes overlook the go-to-market challenges,” he says. “Even if you’re a seed-stage company, you should have a clear view of what you think your go-to-market playbook is going to be.”
This insight reflects a shift in investor expectations. For venture capitalists, a promising product is only part of the equation; they also want to see early-stage startups with a comprehensive plan to engage their audience and drive growth.
Grit and Resilience: Essential Traits for Today’s Entrepreneurs
Building a successful startup is never easy, and Hemmeter believes that grit and resilience are qualities that set exceptional entrepreneurs apart. While previous generations may have been battle-hardened by necessity, Hemmeter worries that today’s young founders, particularly those from privileged backgrounds, may lack the resilience needed to weather the inevitable challenges.
“It always gets hard when you’re building a business,” Hemmeter says. “Grit is critical. There’s a way that this generation, especially privileged young entrepreneurs, don’t necessarily have the same grit and staying power.”
For investors, assessing an entrepreneur’s resilience can be difficult. Hemmeter shares that while background checks and past experiences can provide some insight, true grit only reveals itself under pressure.
“Identifying grit is hard,” he admits. “You can do background checks, talk to past colleagues, but sometimes you still don’t know if someone has the staying power until things get tough.”
The Evolution of Venture Capital in Travel
The rise of venture capital itself has fundamentally reshaped the entrepreneurial landscape. Unlike in the gambler days, founders today don’t have to risk their own personal finances to the same extent. However, Hemmeter acknowledges that launching a venture capital firm comes with its own set of hurdles, especially in the travel industry, which can be cyclical and challenging.
“Raising the first fund for a venture capital firm is incredibly hard,” he says. “We started with an $11 million fund, which isn’t enough to pay anyone. It’s about proving a thesis over years, sometimes with minimal financial reward.”
While venture capital has been a crucial force for innovation, it’s a competitive business that faces its own challenges, including the struggle to achieve successful exits and return capital to investors.
Post-Pandemic Innovation in Travel
The COVID-19 pandemic was a major disruptor for the travel industry, exposing its vulnerabilities but also accelerating technological adoption. Hemmeter sees a renewed commitment within the industry to become more agile, driven by the lessons of the pandemic.
“The pandemic caught travel supply flat-footed,” he reflects. “Now, there’s a real commitment across the industry to never let that happen again. This has unlocked a pace of experimentation that allows good ideas to percolate.”
This accelerated innovation has created new opportunities for startups to develop solutions that enhance flexibility and resilience, setting a stronger foundation for the future of travel.
The Next Frontier for Travel Entrepreneurs
Hemmeter believes that the travel industry’s size and ongoing transformation offer vast opportunities for today’s “makers’ to build billion-dollar businesses. The journey from gamblers to promoters to makers has brought the industry to a place where thoughtful, sustainable innovation can flourish.
“The travel landscape is big enough that building a billion-dollar business is not that big of a stretch,” Hemmeter concludes.
For today’s entrepreneurs, the path forward will require not just a great product, but also resilience, a strong market strategy, and a deep commitment to solving meaningful problems. As the travel industry continues to evolve, the makers who combine vision with grit are the ones who will define its future.
