In this Alumni Spotlight interview, we delve into the inspiring career journey of Daniel Kang, an alum who has navigated the intersection of finance and technology since his time at Oliver Wyman. Along the way, he documented his experiences, culminating in the release of his book, The Super Upside Factor, which explores the concept of taking asymmetric bets in life and career decisions. Join us as we explore Daniel's insights on risk management, the importance of mentorship, and the lessons learned from his dynamic career path.
Tell us about your career journey and what you've been doing since you left Oliver Wyman.
I joined Oliver Wyman in 2016 straight after leaving McGill University in Montreal and spent two years there. After gaining valuable work experience, I wanted to get involved in both finance and tech and found that hybrid in venture capital. I spent the next two years at SoftBank Vision Fund where I deployed about half a billion dollars in mostly fintech, mobility, and artificial intelligence (AI) companies. It was a great time to be there because 2018 to 2020 were the golden years of tech valuations and venture capital investments. I had the opportunity to formally sit on the board of a now publicly traded company that traded at $10 billion at its peak.
While I had an amazing time there, I wanted to start my own business in order to have a direct impact on my mission to create fair access to opportunities. I thought a great way to do that was to hedge my bets a bit while learning something new.
What was your journey to starting your own company?
I pursued master’s degree in public policy at the University of Oxford. For my first semester, I immersed myself in the school, taking up rowing and debate. As I started my second semester, I began to explore the entry point into launching my company. Within a few months, I raised a pre-seed round and got into Y-Combinator, an accelerator that incubated companies like Airbnb, Coinbase, and Instacart, among other category-defining tech companies.
The initial product of my company Flowbo, was providing financing to non-salaried employees like freelancers and content creators. My co-founder and I created a new credit model taking in financial and social data through APIs, and launched products like credit cards, early-payments, and workflow tools.
What were some notable challenges you faced and how did you overcome them?
I will say, it was a very turbulent time at first. We raised $3.4 million and interest rates spiked immediately. We tried moving to Asia to operate on a similar model and had to shutdown the year after. There were several pivots, but we're still alive and still building our company.
As I was going through these ups and downs, I documented my journey as it unfolded. I shared a little bit of my writing with fellow founders and investors in the space, and people seemed to like it. That led to speaking opportunities, including one at Medium. An acquisition editor at Wiley happened to be there and reached out before asking me to turn my experience into a book, The Super Upside Factor, which was just released.
Congratulations! Tell us a little more about the book.
The high-level view is about applying asymmetric bets in life decisions. There's a trillion-dollar industry that gets paid to be wrong. Venture capitalists, at least in the early stages, don't hit their target returns 90% of the time, but they still exist and make money because the few times they win the returns are 100x or 1000x.
The primary thesis of the book is that we can position our careers and life decisions to be exposed to such extraordinary outcomes by taking these asymmetric bets. Large outcomes rarely come from linear progression and often come from a few inflection points that give you 100x return elevation. The book presents a formulaic approach of how venture capitalists consistently identify these skewed bets where the upside is so great and the downside limited, thus generating great returns. My book applies that approach to life and career decisions.
How did your time at Oliver Wyman contribute to your entrepreneurial spirit?
Oliver Wyman gave me a foundation in both skillsets and financial stability. It is a place that allowed me to transition from risk restriction to a risk aversion mindset. When people want to take big swings, whether it's entrepreneurship or being an artist or whatever the case may be, not everyone is in a position to do it because if it doesn't work out the blow is so devastating they can't come back from it.
When I started my entrepreneurship, I had a lot of mechanisms where I hedged myself, like going to Oxford before and giving myself 10 months to raise capital before pulling the plug. Things that I put in place to make sure that whatever scenario did play out meant that the downside was tolerable for me.
Any advice for consultants starting their career now?
When starting a consulting career, it's important to understand the trade-offs between diversity and fast upward mobility. While working across diverse projects and locations can provide valuable experience — in my two years, I worked on telecom, finance, and retail in Germany, the US, and Korea — it may also hinder productivity due to the constant need to adjust to new environments and teams. In contrast, focusing on one area probably makes it easier to build expertise and foster stronger relationships for upward mobility. I’ve also learned that consulting is all about people. Following people whom you respect and who are willing to mentor you is an incredible gift and a cheat code to really learning the craft in any field.
This page was originally published on April 23, 2025.