How Tim Evaluates Founders and Accepts Being Wrong

Before becoming one of the most influential venture capitalists in Silicon Valley, Tim Draper built a career defined by early conviction, independent thinking, and a willingness to back ideas long before they reached mainstream belief. Over decades, Tim has invested in and supported some of the most transformational companies of the modern era, shaping how the world communicates, moves money, explores space, and builds technology.

In this conversation, Tim reflects on backing category-defining companies, including Tesla, SpaceX, Skype, Hotmail, Twitch, and Robinhood, investments that went on to create hundreds of billions of dollars in enterprise value and permanently change global industries. He also shares the impact of Draper University, where thousands of founders have been trained, leading to thousands of companies launched and multiple billion-dollar outcomes.

The episode dives deep into Bitcoin and economic freedom, tracing Tim’s early belief in decentralized systems, his experience buying Bitcoin as early as 2011, and why he views it not as a trade but as a long-term technological shift with global implications, especially in a world of inflation, fragile banking systems, and unstable currencies.

Follow Tim - X (Twitter): https://x.com/TimDraper
Follow Derek - X (Twitter): https://twitter.com/derekjandersen

Episode Partners:
Delve
Delve uses AI agents to handle SOC 2, ISO 27001, GDPR, and more - Divot listeners get $1,500 credits to get started: https://delve.co/deals/divot

Timestamps:
1:50 — Making a Divot: Entrepreneurs, Impact & Building for the Future
4:14 — Entrepreneurs Are Superheroes From Day One
5:06 — Mindset Beats Talent: Why Entrepreneurship Can Be Taught
6:52 — Real Results: Founders Trained, Companies Built, Unicorns Created
8:05 — Risk as Identity: When “Crazy” Becomes Your Advantage
10:10 — Be Your Own Media Company: Turning Attention Into Power
11:56 — Failure Doesn’t Matter: Why Nobody Remembers Your Mistakes
13:30 — Boom and Bust: Who Actually Survives Tech Cycles
14:24 — The Cost of Inaction: Missing Facebook, Uber & Airbnb
17:21 — Buying Bitcoin at $4: Conviction Before Consensus
18:55 — Why Bitcoin Survived: The Unbanked, Remittances & Reality
20:54 — Predictions vs Regulation: When the Future Gets Delayed
25:43 — Bitcoin vs the Dollar: Inflation, Power & Store of Value
32:14 — The SVB Wake-Up Call: When Banks Aren’t Safe
36:26 — Independent Thinkers Win: Why the 1% Build Everything
41:09 — Fixing Broken Systems: Growth, Markets & California
48:24 — Raising Independent Humans, Not Followers
50:39 — The Core Belief: You Have Your Own Path
52:31 — Measuring a Life by Impact, Not Status

Follow Divot:
YouTube: https://www.youtube.com/@Divotpod
X (Twitter): https://twitter.com/divotdotorg
Instagram: https://www.instagram.com/divotpod
TikTok: https://www.tiktok.com/@divotpod
LinkedIn: https://www.linkedin.com/company/divotdotorg

Hashtags:
#TimDraper #VentureCapital #Entrepreneurship #Startups #Investing #BillionDollarCompanies #Bitcoin #EconomicFreedom #Innovation #Founders #Leadership #FutureOfTechnology #DivotPodcast