Dan Kan: About 35 rejections and a unicorn

“Every time I thought I was being rejected from something good, I was actually being redirected to something better”-

Dan Kan is the co-founder of Cruise Automation, a startup that General Motors bought in March for $1 billion in a cash and stock deal. Seven years back Kan, then a senior in Claremont McKenna college was not even considered worthy of a plain finance job by almost 35 potential employers.

“I remember distinctly when I was graduating that I was going to go into finance. Like, ‘Oh! This is the path. Everyone goes into finance.’ You make a lot of money,” says Kan.

With only two options in hands: teach English in Korea or work at a startup in San Francisco called UserVoice, a platform which helps companies collect user feedback, Kan chose the latter. And rest, as they say, is history.

Kan’s story is a perfect mix of a bit of luck, right connections, a healthy appetite for risk and a remarkably unflappable demeanor.

Entrepreneurial Blood

Entrepreneurship runs in Kan’s family. His mother started her own real estate and mortgage broker business in San Francisco in the 1990s. Dan’s older brother, Justin, is also an entrepreneur. Justin moved to San Francisco after graduating college and started the online video platform Justin.tv in 2006, which later became Twitch.

Kan’s family has always been a source of inspiration and support to Dan. Even now that he is a co-founder of a unicorn that just inked a $1 billion deal, Dan still shares an apartment with one of his two brothers in an adjoining apartment with their third brother.

Dan says, quite modestly, that his connections helped him get his foot in the door of Silicon Valley. “I wouldn’t be here without my brother or the other guys at Twitch. That’s probably the most important thing,” he says. "Not just having an idea or executing on an idea -- it’s all about the connections that you have and the people you know and the people who support you.”

Spirit of Perseverance

But one cannot make it only by contacts and connections. Entrepreneurship is a spirit marked by perseverance and tenacity.

“Dan has a fearlessness that is such a critical component to a startup being successful. People think of startups as risky, but often inside of them there is a lot of fear of failure. Dan is that voice in the room that says, ‘What if?’ to challenge everyone to reach a little higher,” says Nabeel Hyatt, a partner at Spark Capital, which led Cruise’s series A investment.

But Dan is more than a dreamer. “Dan also just has amazing follow-through skills, he makes sure things get done, which is what enables him to be fearless with the team," Hyatt says. "He has the follow through to back up his ambitions for himself and the people he works with.”

On Road to Success

Dan tried his hands at two businesses before Cruise happened. First, in 2011, Dan launched Appetizely, a company that built iPhone apps for restaurants that pushed coupons to attract customers at periods of low traffic. After some 30 apps, Apple decided that all Appetizely apps be combined into one because of their similar functionality. Dan decided that if he couldn’t offer each restaurant its own app, it wasn’t going to be attractive to restaurants. Within a few months of launching, the startup was closed down.

Later that year, Dan launched Exec, an on-demand personal assistant service. Customers almost exclusively used the Exec app for house cleaning. Dan pivoted his San Francisco-based startup to focus on house-cleaning on-demand services. That was more successful, but Dan’s heart wasn’t in it- “For me, that wasn’t really what I was passionate about.” In 2014, he sold the startup to San Francisco-based on-demand service company Handy, which has since become a leader in the space.

“He's got the grit required for early stage startups,”says Tristan Zier, the current head of mapping operations at Cruise who also used to work with Dan at Exec. “At Exec, he was willing to scrub toilets for clients. At Cruise, he was willing to go out on mapping car runs in the middle of the night. He's a hard worker through and through.”

There are many others who have similar opinions about Dan including Amir Ghazvinian, a lifelong friend of Dan who was also part of the Exec founding team- “Daniel has always been a guy with a ton of bold ideas, and a lot of confidence in being able to execute on those ideas and bring them into existence. He's always thinking about ways to make products and experiences better than they already are.”

On Cruise

It was in 2014 that Dan began to work on Cruise Automation along with Kyle Vogt. He had known Kyle for years because Vogt was part of the founding team for Justin Kan's Justin.tv and Twitch. Dan interned with his brother and Vogt for a summer when he was still in college.

It was their association and Vogt’s passion for autonomous driving that set the Cruise sailing. And after some time GM deal happened. The $1 billion gets split between Dan, his better-known co-founder and the CEO of Cruise Automation, Kyle Vogt, the other 40 Cruise Automation employees working at the startup when it was acquired and the early investors.

Dan is a remarkably simple guy, unruffled by the spotlight. That’s because he’s exactingly practical. Throughout the exceptional highs and lows of Silicon Valley startup life, Dan stays rational. He says that stress just adds another problem. Dan’s combination of appetite for risk and built-in zen is the ideal business suit for Silicon Valley startup life.

“I would definitely say that I am risk seeking a lot of things,” says Dan. His surgical pragmatism is disarming in its simplicity: when he encounters a problem, he isn’t dissuaded. He just finds a solution. “The way that I approach it is that every problem, or every situation that can give you stress, is just another problem that you have to solve. So if you can think about it rationally, step back and say, ‘OK, what can I do to make this work?’ That is how we approach everything at Cruise and how I approach everything in my life.”

Strategically simple. Isn’t it?