All Episodes

March 27, 2025 49 mins

Daniel Kang is the CEO & co-founder of Y-Combinator-backed startup Flowbo, a marketplace that provides financing to influencers and allows fans to share in their success. He is the author of his new book - The Super Upside Factor: Asymmetric Principles that Will 10x Your Life

In this episode, Daniel Kang, author of The Super Upside Factor, shares his journey from consulting at BCG to venture capital at SoftBank and ultimately founding Flowbo, a Y Combinator-backed marketplace that helps creators access capital. He discusses the challenges of building Flowbo during COVID-19, securing early customers, and the importance of asymmetric bets in life and business. Daniel also explains why writing led to his book The Super Upside Factor, how to think about quitting strategically, and why risk capital dynamics differ between the US and Europe, and much more!

Timestamps

00:02:30 – Daniel’s background

00:04:15 – Moving from consulting to venture capital

00:06:30 – Importance of building your own reputation rather than borrowing from prestigious companies.

00:10:20 – How Daniel identified the gap in financial access for freelancers and creators

00:12:10 – Challenges of raising funds during COVID-19.

00:14:50 – Early customer acquisition strategy and learning from Paul Graham’s "Do Things That Don’t Scale."

00:17:25 – Daniel's approach to connecting with creators by organizing exclusive events.

00:19:05 – Why writing became a powerful tool for Daniel to reflect on strategy and personal growth.

00:23:45 – Explanation of "asymmetric principles" and why VCs can afford to be wrong most of the time.

00:26:15 – Three key principles for asymmetric bets: Budget for failure, target high upsides, and use feedback loops.

00:28:40 – How these principles apply beyond investing to life and career decisions.

00:31:00 – Differences between US and European VC markets: Risk capital and founder dynamics.

00:34:45 – How AI is reshaping the startup ecosystem and reducing costs of launching companies.

00:37:15 – Why niche and distribution will matter more for future AI companies.

00:40:30 – Building a "life portfolio" and how Daniel manages risk in his personal and professional life.

00:43:20 – The correlation between household income and likelihood of pursuing creative careers.

00:45:55 – How asymmetric bets can help level the playing field for creatives from middle-class backgrounds.

00:49:00 – The art of quitting: Different types of quitting and when to walk away from a failing business.

00:52:10 – Why quitting isn’t necessarily a failure but a strategic decision.

00:54:45 – Advice for founders raising funds: Focus on creating value before raising money.

00:57:00 – Why founders should avoid private negotiations and aim for auction-like funding dynamics.

Daniel’s Links 

Mark as Played

Advertise With Us

Popular Podcasts

Stuff You Should Know
Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

The Breakfast Club

The Breakfast Club

The World's Most Dangerous Morning Show, The Breakfast Club, With DJ Envy, Jess Hilarious, And Charlamagne Tha God!

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.