Mike Maples, Jr. is a co-founding partner of Floodgate and a seasoned seed investor behind tech giants like Twitter and Twitch. In this discussion, he delves into the essence of transformative entrepreneurship, advocating for breaking free from societal norms. He highlights the need for founders to embrace disagreeableness and seek future-focused customers. Journaling emerges as a powerful tool for self-discovery, while Maples underscores the importance of authenticity over tribalism in fostering innovation and creating meaningful movements.
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insights INSIGHT
Jonathan Livingston Seagull Metaphor
Founders, like Jonathan Livingston Seagull, pursue perfect flight, departing from the consensus.
They embrace limits less, similar to how Jonathan Livingston Seagull was banished for wanting perfect flight.
insights INSIGHT
Asymmetric Warfare
Startup capitalists change the subject; they don't compound like traditional capitalists.
They wage asymmetric warfare on the present by creating radically different futures.
insights INSIGHT
Transcending Competition
Startups transcend competition; they don't beat it.
They create a different future, compelling early adopters to self-actualize by joining that future.
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The Classic Guide to the Best-Performing Investment Strategies of All Time
James P. O'Shaughnessy
In 'What Works on Wall Street', James P. O'Shaughnessy provides an in-depth analysis of over 90 years of stock market data to identify the most effective investment strategies. The book examines various factors such as price-to-earnings ratios, price-to-sales, price-to-book value, dividend yields, and more. It challenges conventional wisdom and offers multifactor strategies that have historically generated the best returns. The book is designed to help investors of all levels, from conservative to aggressive, in selecting the best strategies for their investment objectives.
The Beginning of Infinity
Explanations That Transform the World
David Deutsch
In this groundbreaking book, David Deutsch argues that explanations have a fundamental place in the universe and that improving them is the basic regulating principle of all successful human endeavor. The book takes readers on a journey through various fields of science, history of civilization, art, moral values, and the theory of political institutions. Deutsch explains how we form new explanations and drop bad ones, and discusses the conditions under which progress, which he argues is potentially boundless, can and cannot happen. He emphasizes the importance of good explanations, which he defines as those that are 'hard to vary' and have 'reach', and argues that these explanations are central to the Enlightenment way of thinking and to all scientific and philosophical progress.
Jonathan Livingston Seagull
Richard Bach
Russell Munson
The book tells the story of Jonathan Livingston Seagull, a seagull who is different from the others in his flock. While most seagulls focus on eating and survival, Jonathan is passionate about flying and constantly challenges himself to improve his flight skills. His nonconformity leads to his banishment from the flock, but he continues to pursue his dreams, eventually finding other like-minded seagulls and learning valuable lessons about love, kindness, and transcendence. The story is an allegory about seeking a higher purpose in life and not compromising one's vision, even in the face of societal pressure[2][4][5].
Genius of the Beast
Howard Bloom
In this book, Howard Bloom presents a compelling argument that capitalism, despite its imperfections, is a system that allows the best and brightest to emerge. He advocates for reviving businesses by injecting them with emotion, desire, and passion. Bloom draws on his diverse experiences, from his work in popular culture to his insights into human and mass behavior, to illustrate how all life, from bacteria to human beings, is programmed to flourish under the free market system. The book is filled with personal anecdotes and historical examples, making it both captivating and thought-provoking.
Pattern Breakers
Why Some Start-Ups Change the Future
Mike Maples Jr.
Peter Ziebelman
Pattern Breakers, written by Mike Maples Jr. and Peter Ziebelman, challenges traditional startup wisdom by revealing the hidden forces that drive extraordinary success. The book is based on extensive research and real-world examples from transformative startups like Twitter, Twitch, and Lyft. It emphasizes the importance of a different mindset and actions to harness developments that others might miss or initially see as crazy. The authors provide practical advice on how to transcend ordinary thinking, capitalize on market opportunities, and build a community of true believers to revolutionize industries.
Mike Maples, Jr., co-founding partner of the VC firm Floodgate, is the veteran seed investor behind some of the 21st-century’s great success stories, including Twitter, Twitch, and Applied Intuition.
His book, Pattern Breakers (co-authored with Peter Ziebelman), articulates a new model of foundership, one built on the simple premise that transformative startups upend rather than improve current practices.
My company, OSV, is built around my belief that the collapse of the old models presents enormous opportunities to those savvy enough to seize them, so I had a blast quizzing Mike on the nuts and bolts of pattern-breaking foundership, from finding true believers to waging asymmetric war on the status quo.
If Mike’s theory sounds as interesting to you as it did to me, check out our Substack, where we’ve distilled some pattern-breaking insights and shared the episode transcript. I also encourage you to buy Mike’s excellent book.
In the meantime, I hope you enjoy our conversation as much as I did!
Infinite Loops 
