Mike Maples is an 8x Midas List investor and founding partner at Floodgate Fund. In our conversation, we dive into his latest book, "Pattern Breakers: Why Some Startups Change The Future." Mike shares his frameworks on how top startups beat incumbents by redefining categories, and he reflects on his worst and best decisions. We also discuss what the future of venture capital may look like over the next decade - here are a few favorite takeaways on what makes outstanding startups from one of the industry's most influential names.

(00:00) Intro

(01:12) Meet Mike Maples: Venture Capital Icon

(04:20) The Genesis of Twitch and Startup Pivots

(07:51) Understanding Inflections in Startups

(14:38) The Role of Insights and Ideas in Startup Success

(22:13) The Importance of Movements and Founder-Future Fit

(26:10) Case Studies: Quibi, Tesla, and More

(43:41) The Trap of Mundane Startup Ideas

(45:36) The Inflection Stress Test for Startups

(47:06) The Twitter Success Story

(52:40) The Rise of Seed Funding

(56:55) Traits of Successful Founders

(59:39) The Importance of Storytelling in Startups

(01:05:47) Navigating the Challenges of Disruptive Startups

(01:08:31) Reflections on Early Investment Decisions

(01:13:57) Entering the Venture Capital World

(01:20:25) The Evolution of the Tech Industry

(01:22:47) Reflecting on the Dot-Com Era

(01:23:06) The Evolution of Cognition and AI

(01:24:03) Investment Strategies and Market Trends

(01:25:56) The AI and Dot-Com Bubble Comparison

(01:33:46) The Rise of Bitcoin and Crypto

(01:37:02) Navigating Venture Capital Cycles

(01:49:57) Advice for Aspiring Investors

(01:54:09) The Importance of Authenticity and Specialization

(02:03:20) Closing Thoughts and Reflections

Executive Producer: Rashad Assir

Producer: Leah Clapper

Mixing and editing: Sam Dewees and JR Bohannon

Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA

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About the Show

Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode, Logan goes behind the scenes with world-class entrepreneurs and investors. If you're interested in the real inside baseball of tech, entrepreneurship, and start-up investing, tune in every Friday for new episodes.