What if the secret to happiness wasn't a grand epiphany, but a bad movie playing at 2AM? In this episode, Sean sits down with Ben Narasin, a veteran venture capitalist who has backed companies like LendingClub, Rippling, and Omada Health, to explore what decades of investing at the highest level teaches you about life, patience, and staying true to your standards. Ben reveals why lowering the bar in venture is the beginning of the end, and how he learned to sit with the discomfort of seeing 2,500 pitches in a year and funding just one, without letting that silence become a compromise. You'll also hear his counterintuitive advice to founders: stop optimizing your valuation pitch and start treating your investor relationships like a marriage, because you'll be living with that choice for ten years or more.
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📚 NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M)
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Get my brand new eBook free - https://welivetobuild.com/network
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📋 WORK WITH ME
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▶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebook
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🔗 CONNECT WITH SEAN
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▶ LinkedIn: https://linkedin.com/in/seanweisbrot
▶ Inquiries: [email protected]
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🕐 CHAPTERS
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00:00 - Happiness Is Wanting What You Have
00:35 - Why Ben Only Funded 1 of 2,500 Pitches
01:11 - LendingClub, Rippling, and the Fired Founder Pattern
03:11 - Game Theory Will Ruin Your Investor Relationship
06:44 - The ChatGPT Trick for Vetting Your VC
08:14 - No Skeletons: The Open LP Meeting Experiment
18:03 - Specifics Are Your Friend, Generalities Your Enemy
25:04 - Work Hard When There's a Reason To
31:28 - Sleep, REM, and the Brain-Cleaning Function
33:46 - Life Is Hard for Everybody. Get Over It.
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