Chuck Isgar (MBA ’25) talks travel with Roame, a points booking tool, and Getaway, a cabin provider that helps you discover the outdoors.
Summer – and perhaps some travel – is near. To provide some ideas for upcoming trips, there are two HBS alumni-founded companies ready to help. Have some miles or credit card points lying around? Roame is Google Flights, but for points, and is ready for you to search across different potential trip options to make best use of your points – and perhaps even score you a business class seat for cheaper than what an economy seat would have cost in cash. Craving a break from technology or looking for a setting to deeply connect with a loved one? Getaway provides calming, nature-filled experiences less than two hours from many major cities across the US.
Roame: Helping you make best use of your credit card points and airline miles
After spending over 20 hours searching across different airline’s websites, Tim Qin (MBA ’19) found the “holy grail” of points: a $15,000 Japan Airlines ticket for just 70,000 points. This experience convinced Qin to trade in his finance career and begin his company, Roame. At its core, Roame serves as a one-stop-shop to search for reward travel opportunities across airlines, dates, and cabin classes. Importantly, their website eradicates the need to go search for redemption flight options across each airline’s individual website. The company, which went through the famous Y Combinator in summer of 2023, has accumulated 300,000 users and has over 100,000 subscribers to its newsletter, which shares top points redemption opportunities.
While some people do not believe that points and miles are a big market, Qin shared that the market size is there – it is simply underserved. According to McKinsey, there are at least 30 trillion unused frequent flier miles. While many initially think just of their existing miles or points with airlines, a major stash is actually in credit card points, which can easily be transferred to airlines. While each credit card and airline have different point conversion values, American Express, Chase, CapitalOne, Citi, and more have partnerships with many airlines, which means there is great value in knowing where to get best use of your credit card points. However, as the number of credit cards and transfer partners increase, the process becomes exceedingly complicated and time-consuming, hence the need for a tool like Roame.
As to why he believes there continue to be so many points going unused, Qin shared an interesting phenomenon: nearly everyone has points, so they either think they know the intricacies of points or they know they do not. For the latter camp, some basic points knowledge may be helpful to better understand this company – and how you can best use your points in upcoming travel. While travel tools like The Points Guy help provide a points to cents ratio for each airline, a helpful benchmark is 1 point : 1 cent. In other words, you use 100,000 points to book a flight that would cost $1,000 if you paid with cash. Here’s the problem: while this ratio is often referenced, it is not the best way to use points. When Qin booked a $15,000 ticket for 70,000 points, his ratio was 1 point : 21 cents. Now, that ratio can be quite challenging to find. But with the right tools – Roame included – and a little bit of luck, a 1 point : 3-4 cent ratio is feasible to find. By booking with a ratio of that sort compared to a 1 : 1 conversion, you are effectively booking four trips for the price of one.
Finding these types of deals can be a very time-consuming process, which leads Roame to its ultimate goal: “provide one click booking across cash and points.” While most in the tech community seem to be abuzz about AI, Qin is open, but not focused, on where AI fits into the platform. “We don’t want to build a travel product that is AI first… we want to use AI to help people,” Qin explained. A bigger challenge for the company seems to lie in customer education. For example, most people do not know that they can transfer their major credit card program miles to a variety of airlines, such as AirFrance.
Roame initially launched on Reddit “to give back to the reward travel community.” The four person team is hard at work gearing up to launch a mobile app and hotel product. When asked whether people should use points on a “decent” conversion or hold out for a deal to write home about, Qin shared helpful advice: “points, at the end of the day, are for your travel aspirations. [Even] if you use points for a sub-optimal redemption, do it.”
Getaway: Cabins enabling outdoors access and human connection within two hours of major cities
Beautiful nature. About two hours away from where you live. “Everything you need and nothing you don’t.” This is the value proposition that Getaway provides, as shared by founder and CEO Jon Staff (MBA ’16). Getaway now operates almost 1,300 cabins in locations an hour or two from cities such as Boston, New York, Los Angeles, Austin and San Antonio, and more. Staff and the company believe that “free time should be a right and ritual for everybody.” In a day and age where our daily screen time continues to increase, Getaway intends to provide a tranquil environment that escapes the constant connectivity that permeates our everyday lives.
Staff describes the company, which has raised over $100 million to date, as “asset medium.” The company is not an online platform and nor are they “trying to pretend they are a tech business.” While they are in the business of buying land and building cabins, the cost of doing so is far less than that of, say, building a hotel in a downtown area. When asked about the pros and cons of being a company operating physical assets (as opposed to a digital platform or aggregator model, like many other travel startups), Staff shared that they benefit from owning physical assets where they can capture value. Perhaps most importantly, they create venues where “people truly [make] memories that last lifetimes,” an experience that Staff noted “doesn’t happen over an app.”
Relatedly, while Staff is proud of the great feedback they hear from customers, the commentary is less about their feelings on Getaway itself, and instead more centered on the life experiences Getaway unlocks, such as getting to better know their kid. Getaway prides itself on providing “consistent cabins and service” that lend themselves to these types of human experiences. To facilitate the simplicity that one experiences when arriving at a Getaway, much work goes into choosing site locations. When considering new locations, they visit the site and want to see what it looks like, smells like, and sounds like, along with understanding the regulations that govern the land. Staff shared that many properties fall out of consideration because of highway noise. This level of detail shows the commitment that Staff and the Getaway team have to ensuring that they are providing the “quiet” experience they promise every time someone visits one of their properties.
While so far the clientele has been primarily leisure travelers, Staff shared that the team is working on Getaway Groups in response to consistent customer requests over the last eight years. Initially fearing that groups would detract from others’ experience – hence why Getaways do not have lobbies or restaurants and instead provide fire pits – the company is thoughtfully providing group gathering spaces while ensuring the peaceful guest experience remains unaffected for all. Getaway Groups, which recently launched last year, is acting as a “startup within a startup.”
Despite the company’s success to date, Staff believes there are a “lot of people yet to reach.” Industry reports from banks such as Goldman Sachs support the growth of this space. With these tailwinds in mind, Getaway remains focused on serving the company’s ideal customer, a psychographic which Staff says “want less screen time… want to be more immersed in nature… as part of [their] wellness routine.” This group is seeking “a place to recover and rejuvenate, be that alone or with the people you most love.” And it sure seems like Getaway is providing just that experience.
Chuck Isgar (MBA ’25) loves all things startups. He created and runs Above Board, a weekly newsletter which features Q&A's about startup investment, board management, and corporate governance. Most recently, he served as the Chief of Staff at Scenery, a Series A-stage startup. Chuck previously co-founded and was the CEO of Intern From Home, a recruiting technology company that served students from over 600 colleges. Chuck was a Schwarzman Scholar at Tsinghua University and earned his bachelor’s from Brown University.