The Super Upside Factor: The Art of Risking Little for Big Wins

When Daniel Shin Un Kang got access to broadband internet from the farm he lived on, he discovered how he could pursue a path beyond life as he knew it at the time

At eight-years-old, Kang and his family moved from South Korea to Otterburne, Manitoba—a rural town with around 3,000 people. Most of the residents he knew were either farmers, teachers, or policemen. He recognized early on that if he wanted a different future, he couldn’t just work hard and hope for the best or take high risks in pursuit of greater rewards. He had to take calculated bets—minimizing risk where he could while positioning himself for the biggest wins—because, as an immigrant in a low-income household, he couldn’t afford to gamble his future.

Kang went on to become a venture capitalist at SoftBank, one of the world’s largest investment firms. He also founded a startup that was accepted into Y Combinator (YC), the Silicon Valley accelerator known for producing billion-dollar tech giants like Airbnb, Stripe, and DoorDash. Then, he was offered a book deal by Wiley & Sons, a global leading publisher, to share how he "made the impossible possible" in his book, The Super Upside Factor.

Ahead of the publication’s release, Kang sat down with us to share the idea behind it. He opens up about his journey from having no money or network to achieving a highly successful career, offering a sneak peek at the clear frameworks his book teaches—backed by decision science research and personal experimentation.

Risking less to gain more

The Super Upside Factor is based on the idea of making decisions using asymmetric principles. It involves aiming for potential wins that significantly outweigh any losses and mitigating any risks to prevent severe consequences.

“There's a certain set of opportunities in life where there's a small probability of getting it,” Kang highlighted. “But if you do, the outcomes outsize every other possible thing.”

In finance, VCs spread their capital across multiple startups rather than betting on only one or two. They also invest only a small percentage of their fund into each company. So, even if most of them fail, the overall fund isn’t at risk. Additionally, one successful venture could generate enough returns to cover the losses and still make a substantial profit. 

Consider VC firm Sequoia Capital’s investment into the messaging and video calling app WhatsApp. They turned a $60 million investment into $3 billion after Meta acquired the messaging app for $19 billion. Or Softbank’s investment into the online marketplace-turned-tech giant Alibaba. A $20 million investment reaped over $60 billion after Alibaba’s record-breaking IPO that valued the company at $231 billion.

Similarly, in entrepreneurship, more founders are validating product-market fit before committing to building an idea. Instead, they might launch a minimum valuable product (MVP) or a waitlist to see if people are interested and willing to pay for their service. 

Before the delivery-turned-lifestyle app Fantuan built a product, they tested the demand for their services using the super app WeChat. They convinced mom-and-pop restaurants without delivery to work with them, then put up flyers with QR codes directing customers to their WeChat official account to order. WeChat made it easy and cost-effective to create an MVP, offering peer-to-peer and in-app transactions and letting businesses set up storefronts and acquire customers.

Small town to Silicon Valley

Turning to asymmetric principles to access opportunities that changed Kang's life started in his teens.

Studying became one of the ways he protected himself, he shares. Being 5’7”, Kang believed he had a better shot at excelling in academics than in sports. He also felt it might lessen his chances of being a target for bullying—or at the very least, be acknowledged beyond just being one of the few Asian kids in town.

Kang raised his grades and graduated with the highest marks in his high school. The only barrier standing in the way of making it beyond Otterburne was affording post-secondary. 

Fortunately, once he had broadband internet at home, he discovered many different scholarships that he could apply to online. 

This became Kang’s first asymmetric bet. While minimum wage in his province was around $10 per hour, a single scholarship could be worth as much as $10,000—equivalent to working 1,000 hours part-time. He received 100 rejections before being awarded around 20—enough to fund both his education and livelihood.

While studying commerce at McGill University in Montreal, Quebec, Kang felt pulled toward a variety of pursuits. Each explored ways where others could access opportunities with life-changing outcomes, like he did. He worked with one of his professors as a research assistant in micro-financing and crowdfunding; selected as a Li Ka Shing Scholar to study business in China; and launched a project to address the poverty rate among seniors in Korea—which led to receiving a project with the Clinton Global Initiative University.

Kang would continue to explore paths of democratizing access to capital following his graduation. After working as a management consultant at Oliver Wyman, he became a VC with SoftBank, working in San Francisco and later in London.

“I was lucky,” he admitted. His boss took a chance on him despite not having the traditional experience like attending an Ivy League school or working at Goldman Sachs or Morgan Stanley. He recognized that Kang’s story was unique and his potential to achieve more than the other candidates applying. 

From VC to student and founder

At SoftBank, Kang focused on fintech and marketplace investments, analyzing successful models that reduce friction in providing access to capital.

"One of them was a company in Brazil called Creditas," he shared. "At the time, if you wanted to get a personal loan, the interest rate was anywhere from 100% to 200%. What Creditas was doing was collateralized lending, which brought that rate down to 15%, 20%, or 25%. Those are the types of companies I was super interested in."

Eventually, Kang decided to leave SoftBank to pursue a master’s in policy at Oxford. His research explored opportunities to scale access to capital, technology, and education. By his second semester, he began pursuing an idea that had always been in the back of his mind—but now felt more critical than ever to bring to life.

When COVID-19 hit, Kang recognized just how unprotected freelancers were financially. He also acknowledged how gig work impacted their chances of accessing financial products—especially when they typically had to wait 30, 60, or 90 days to be paid. It was a story he had heard many times long before the pandemic from friends who were creators.

The vulnerability inspired Kang to come up with an idea: a platform to provide better and fairer access to capital. So, from his dorm room, he started Flowbo: a marketplace that connects investors to revenue-generating creators. The vision was that it would offer an advance based on proven metrics and future earnings, like from a YouTube ad or brand deal—with the goal of helping creators focus on their creative process or growing their channel.

168 meetings, 3 wins

To turn his idea into reality, Kang leaned into asymmetric principles as he had done in the past—minimizing risk where he could while positioning himself for the biggest wins.

He started pitching to investors while completing his studies. He knew that if he didn’t secure funding by the time he graduated, he could explore new career paths opened up frompolicy background. After 168 meetings, Kang secured his first round of capital. Flowbo was then accepted into YC’s accelerator, where startups receive both investment and mentorship.

While Kang was heads down in building the product, he was handed an unexpected opportunity. Wiley & Sons approached him for a book deal that would become The Super Upside Factor.

At the time, Kang ran a Medium blog where he wrote about topics related to business and venture capital. He only blocked off one day a month to write articles, but overtime, it grew to having thousands of followers and hundreds of likes per article. It caught the attention of Medium’s team, which invited him to speak at an annual event where an acquisitions editor discovered him.

“This is one of those things where I can afford 15 minutes a day [and] do this a hundred times,” highlighted Kang. “And even if it doesn't work, I still enjoy the writing process of it and I still have content I can share with other people. 

But if it does well, opportunities like these arise and this has now led to me speaking at TEDxStanford and a bunch of other things I imagine will continue to happen. It doesn't take much, right? I think people can start taking a little bit of shots, but place themselves in a position that allows for the big upside.”

The Super Upside Factor takeaways

Kang’s book, The Super Upside Factor, is now available for purchase in retail stores and online—including Barnes & Noble and Indigo. 

Along with detailing how he applied asymmetric principles for his education, career, and book deal, he shares analogies like what he learned when recovering from a spiralling plane as a pilot. This occurs when an aircraft loses lift and begins to fall while rotating uncontrollably towards the ground. 

In the past, pilots didn’t have a clear recovery plan, but over time, they developed a method: reducing engine power, using the plane’s rudder to stabilize, and then applying the rudder to help level the plane. It took time to discover this method as it is counterintuitive. The natural reaction is often to steer the yoke, much like turning the steering wheel of a car during a crash, but doing so actually makes the situation worse.

“When we start doing asymmetric bets, there are foreseeable, really stressful situations that'll happen,” Kang explained. “You want to [prepare] to quit, stop, or move on, so you're not going to spin towards the ground and lose yourself completely. 

That’s sort of the big takeaway when you enter [situations] with downsides. Think about what the maneuvers will be to get out, and when it happens, get out quickly because you don’t want to be thinking while the plane is going down. Have a plan in place and escape in time.”

For anyone looking to make a change in their personal or professional life, Kang encourages reading his book when “you need to do more with less and make decisions under uncertainty.”

“I think my book offers a great framework to create outsized returns while being a little bit risk-averse and not betting your life. The last thing I’ll leave with is that there are many ways to play the game of life. I would consider what games you would do really well at [...] The game that’s worked really well for me is going after these really high-outcome events and trying them 100 times, getting better every time I try. I only need one or two of them to work out.

Other people in my life who’ve been successful said, ‘I only want this one thing, and I’m gonna relentlessly focus on that one thing, no matter what anybody says, and then achieve that one thing, and nothing else matters.’ See what works best for you, and I’m just giving you one of the games that you can play and how I thought about playing that.”

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