“The Best Entrepreneurs Aren’t Afraid to Take Bets”
Daniel Kang is an entrepreneur backed by Y-Combinator and the author of The Super Upside Factor published by Wiley & Sons. Previously, Daniel was a growth equity investor at Softbank Vision Fund in both London and Silicon Valley, and formally sat on the board (observer) of Auto1, a publicly-traded company in Berlin. Daniel studied policy at the University of Oxford and finance at McGill University. In his downtime, Daniel enjoys spending time with family, drinking coffee, writing pop music, and flying as a pilot.
Q: What does it mean to be an entrepreneur?
Being an entrepreneur means thinking for yourself, making your own decisions, and living the consequences of your decisions - in other words, having skin in the game. The quality of a founder is dependent on speed and quality of decision making, while being 100% responsible for the outcomes. That can feel like getting punched in the face every day until you get it right. But the best founders don’t just take hits blindly—they learn, iterate, and optimize.
Daniel Kang
Founder, Y-Combinator
Daniel Kang is an entrepreneur backed by Y-Combinator and the author of The Super Upside Factor published by Wiley & Sons.
His mission is to create fair access to opportunities, which he is driving with both his company and his book. Specifically, in The Super Upside Factor, he distills strategies used by venture capitalists to create outsized returns despite being wrong 90% of the time - but applied to life decisions. He has taught at McGill University and Seoul National University, and has been invited as a speaker by organizations including Medium.com, Clinton Global Initiative University, and New Enterprise Associates.
Previously, Daniel was a growth equity investor at Softbank Vision Fund in both London and Silicon Valley, and formally sat on the board (observer) of Auto1, a publicly-traded company in Berlin. Daniel studied policy at the University of Oxford and finance at McGill University. In his downtime, Daniel enjoys spending time with family, drinking coffee, writing pop music, and flying as a pilot.
Link to the book: https://www.amazon.com/Super-Upside-Factor-Asymmetric-Principles/dp/1394254911/
That’s what I tried to share in The Super Upside Factor to find asymmetric bets so that you win even if you're wrong 90% of the time. Success isn’t about making the perfect call every time. It’s about structuring your decisions so that when you win, you win big—and when you lose, it barely matters. The best entrepreneurs aren’t afraid to take bets; they’re just exceptionally good at placing the right ones.
Q: How easy or difficult is it to approach investors?
I'll scope the questions to venture investors who need to create outsized wins. The primary job of a venture capital investor is to generate returns for their LPs, and they do that by investing in good companies. So the short answer for approaching investors is this: if you're building an exceptional company designed to grow quickly, solving the problem of "approaching investors" is not hard. If your company isn't growing and probably wouldn't do well without some core aspect changing (other than purely capital), then approaching investors becomes much more difficult. I'd separate the two problems.
Q: What do VC's look for?
Generally speaking, VCs try to invest in highly scalable companies in a timely manner while balancing Type I (investing in a company will die) and Type II (missing a company that will become a Unicorn) errors. At a minimum, VCs look for companies that are structurally positioned to grow big and grow rapidly.
Earlier stage investors have less data and greater upsides, weighing their decision on founders, market, and idea as predictors. They tend to care about valuations as they will be diluted in the future.
Later stage investors tend to have more data with less upsides, weighing growth rate in the context of time and capital efficiency. They are less valuation sensitive, care more about the potential outcome because a $100m outcome would be a waste of their resources even evaluating the investment.
Q: Can you give us your insights on the investment landscape in the US vs. other parts of the world e.g. Asia?
My view is that the US has a relatively mature venture capital and startup market with market efficiencies at play at every stage of funding for startups. In other words, with an abundance of different types of capital competing for the best startups, the power balance between investors and startups seems somewhat more balanced than other parts of the world. The abundance of risk capital is what attracts many founders to the US.
Q: This book is such a fantastic milestone in your career. What do you hope to accomplish through it?
My personal mission over the last decade has been to create fair access to opportunities. The book The Super Upside Factor published with Wiley is an extension of my mission, taking any frameworks I've seen and used as a former SoftBank investor and founder backed by Y-Combinator to create outsized returns. The key idea is Asymmetric Principles is to take opportunities that are structurally designed to grow really big, and they can be very minor.
For example, the start of the book was taking 15-minutes a day to write online on Medium, where anyone can get started. Writing in a platform that has big distribution compared to writing in my own physical journal is a minor difference, but the first has the opportunity to grow really big. In my case, I landed a book deal with Wiley & Sons, and had my books endorsed by the ex-President of SoftBank, ex-CEO of Kakao Corp, and Author of Hooked.
Q: What is your definition of success?
Living my life as it was designed to be lived.
Q: What is next? Give us your plan for the year ahead?
I recently talked about "borrowed" vs "owned" reputation. Borrowed reputation is unearned credibility from affiliation - like your school, company, etc. Owned reputation is one you've earned by consistently proving your value on objective metrics. Early in my career, I borrowed from names like BCG, SoftBank, and Oxford. But leaving to start my own company showed just how much "credibility" I was renting, instead of owning. Over the next few years, I'm focusing on objective metrics to create value for other people, through my book and through my career.
Q: Where would you like to see yourself in five years' time?
Most likely doubling down on a few areas where I think will have the greatest impact in creating fair access to opportunities for people. I'd also want to build my own family.
Q: Do you have a motto that you live by?
Live on the edge of possibility, and let God to the rest.
Link to the book: https://www.amazon.com/Super-Upside-Factor-Asymmetric-Principles/dp/1394254911/
Link to newsletter: https://itsdankang.beehiiv.com/subscribe
Published: 13/03/2025
