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10 Things You Didn't Know about Dan Preston

Dan Preston

Dan Preston is the CEO of Metromile, a leading digital insurance platform that's turning the traditional world of auto insurance on its head. By offering real-time, personalized auto insurance policies by the mile, Metromile promises consumers average savings of around 47% on what they'd otherwise pay.

Having enjoyed substantial growth over the past few years, Metromile is now entering a new phase as a publicly traded company. Learn more as we reveal ten things you didn't know about Dan Preston.

1. He studied at Stanford

In 2003, Preston enrolled in Brandeis University. Four years later, he graduated Summa Cum Laude with the highest honors in Computer Science, along with the Michtom Prize for Outstanding Achievement in Computer Science. In 2010, Preston returned to education when he joined the graduate program at Stanford University. He graduated in 2012 with an M.Sc in Computer Science with a specialization in artificial intelligence, machine learning, and computer vision.

2. He founded his first business in 2007

In 2007, Preston was fresh out of university and on the hunt for a job. Rather than wait for someone to offer him one, he decided to take the middle man out of the equation and launch his own business. The result was Photrade, an online business venture that Preston has described as specializing in 'providing photographers the ability to monetize their work in new ways, and to provide such photographers with exposure to larger audiences.' The business ultimately folded in 2008.

3. He spent 2 years as a research assistant

In November 2007, Preston took on a research assistant post at Harvard. Working in collaboration with the Time Series Center, part of the Initiative for Innovative Computing (IIC), Preston researched methods for the discovery of events in time series related to astronomy.

After concluding his research at Harvard in August 2008, he spent a further year at Tufts University researching the underlying true classes of the earth’s surface, in addition to examining gene sets to identify outliers as part of a joint collaboration with the Tufts University Medical School.

4. He worked briefly as a software engineer

In between graduating from Brandeis University in 2007 and returning to education in 2010 at Stanford University, Preston spent a brief time as a software engineer. He then spent 5 months at Inera Inc., where he focused on developing natural language and text processing applications for various features in academic journals. In 2010, he spent 4 months with Google as a software engineer intern.

5. He founded AisleBuyer LLC

In 2009, Preston founded AisleBuyer, a mobile shopping platform that leverages Smartphone technology to improve the shopping experience. The application, which serves as a virtual shopping assistant, can be used by both retailers and consumers. Retailers benefit from analytical insight into in-store shopping behavior, while customers are provided with product info, targeted offers, and a mobile self-checkout option. The startup was acquired by Intuit in 2012.

6. He joined Metromile in 2013

Preston joined Metromile in 2013, originally in the capacity of chief technology officer. A year later, he was promoted to the position of CEO. Under his stewardship, Metromile has enjoyed significant growth, widening its market foothold and establishing itself as an industry leader.

For those new to the company, Metromile offers insurance on a low, flat monthly fee along with an additional per mile charge. A dongle plugged into the car's diagnostic system records mileage, as well as tracking details of any accidents to expedite claims settlement. The system can also be used to schedule car repairs and even rent a car.

7. He thinks going public through a SPAC merger was beneficial

On February 10, 2021, Metromile began trading as a public company. As Tech Stuff writes, its exit from the private market was expedited by its decision to merge with a special purpose acquisition company (SPAC).

According to Preston, the decision to go public through a SPAC merger (a step that's grown in popularity in recent years), came with numerous benefits, including offering the company the ability to provide its investors with greater detail on its growth plans. Had the company gone public through a traditional IPO, Preston says, it would have needed to wait a further year and go through a further financing round as a result.

8. He's learned to embrace remote working

In February 2020, Metromile moved into its swanky new headquarters in San Francisco. A month later, the COVID pandemic broke, forcing the company to abandon its fancy new office for remote working. Although it took some adjustment, Metromile has now embraced a hybrid model of remote work.

As writes, prior to the pandemic, Metromile had a small handful of remote workers in four or five states. Today, it has more than 250 employees working remotely across 22 states. “There are a number of folks in the company who are closer to their families and loved ones. It’s pretty heartwarming,” Preston says.

“I’m happy to let people move where they want to and work remotely. They have a permanent place at Metromile." He doesn't, however, believe that remote working will ever replace office space entirely. “I would be surprised if creative spaces weren’t important for companies in the long-term,” he says. “Office space will be an important part of company culture, but it will look different than it ever did.”

9. He's just secured a massive investment deal

On February 2, Preston announced that Metromile had just pulled off a massive investment deal. As reports, the investment, which amounts to a very attractive $50 million, comes by way of former Uber CEO Ryan Graves and his investment firm Saltwater.

10. He believes the pandemic will accelerate Metromile's growth

Metromile has already enjoyed huge growth under Preston's leadership, but he believes the next few years will see even more of us move away from fixed-based pricing insurance in favor of pay-per-mile alternatives like Metromile's.

During an interview with, Preston explained how the COVID pandemic has worked to substantially increase the public's appetite for transportation-as-a-service. "Amid the pandemic, about 40 percent or more Americans are now working from home, which further validates our model.

We believe that the era of fixed-based pricing is coming to an end," he says. "With uncertainties like the pandemic, people want to have more control. Pay-per-mile auto insurance gives drivers more control over how much they want to pay and can save them 47 percent a year right away. This is meaningful, especially if you need more control over your finances."

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Allen Lee

Written by Allen Lee

Allen Lee is a Toronto-based freelance writer who studied business in school but has since turned to other pursuits. He spends more time than is perhaps wise with his eyes fixed on a screen either reading history books, keeping up with international news, or playing the latest releases on the Steam platform, which serve as the subject matter for much of his writing output. Currently, Lee is practicing the smidgen of Chinese that he picked up while visiting the Chinese mainland in hopes of someday being able to read certain historical texts in their original language.

Read more posts by Allen Lee

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