Going public and navigating tech cycles

Michael Saylor is the CEO of Strategy (formerly MicroStrategy), the first publicly traded company to convert a material portion of its balance sheet into bitcoin. In this conversation, we revisit the very first time Michael Saylor ever publicly talked about bitcoin — recorded in late 2020 when bitcoin was trading around $10,000. We discuss his background founding MicroStrategy at age 24, the macro conditions that led him to reject cash as a store of value, why he chose bitcoin over gold and real estate, how he acquired $425 million in bitcoin without moving the market, and why he believes bitcoin is on a path to rival or surpass gold's market cap.

========================

Consensus Miami is the largest crypto conference in the world — May 5-7, 2026 in Miami. 20,000 attendees. 72% director-level or above. The deals, partnerships, and investments that shape the next cycle get made here. Use code POMPLIANO for 25% off your pass → https://go.coindesk.com/c26pomp

========================

Arch Public is an agentic trading platform that automates the buying and selling of your preferred crypto strategies. Sign up today at https://www.archpublic.com and start your automated trading strategy for free. No catch. No hidden fees. Just smarter trading.

========================

Bitget (https://bitget.com/promotion/futures-tradfi?channelCode=regd&vipCode=nkew) is the world's largest Universal Exchange (UEX) (https://bitget.com/promotion/futures-tradfi?channelCode=regd&vipCode=nkew), serving over 125 million users with access to over 2M+ crypto tokens, and TradFi markets such as 100+ tokenized stocks, ETFs, commodities, FX and precious metal like Gold. At launch, users can trade 79 instruments with USDT directly with the App. Users can also enjoy high liquidity and low slippage, while trading these assets with up to 500x leverage. For more information on Bitget TradFi, visit this article (https://bitget.com/support/articles/12560603846859). For more information, visit: Website (https://bitget.com/) | Twitter (https://x.com/bitget) | Telegram (https://t.me/BitgetENOfficial) | LinkedIn (https://linkedin.com/company/bitget-global/) | Discord (https://discord.com/invite/bitget)
For media inquiries, please contact: media@bitget.com

========================

• 0:00 - Intro
• 1:25 - Michael Saylor's background & founding MicroStrategy 
• 29:40 - The 99% stock crash & lessons learned 
• 31:07 - How COVID changed MicroStrategy's business 
• 33:37 - The macro problem: cash melting & asset inflation 
• 40:45 - How Saylor discovered bitcoin 
• 45:23 - Why not real estate, equities, or gold? 
• 49:10 - Bitcoin's network dominance & why it already won
• 53:30 - Addressing the "someone can copy it" critique 
• 59:28 - Convincing the board: homework assignments & deliberations 
• 1:04:30 - How they acquired $425M in bitcoin without moving price 
• 1:09:45 - Reaction from other CEOs & breaking the mental block 
• 1:12:00 - The four-minute mile moment for corporate bitcoin 
• 1:17:00 - Addressing bitcoin's volatility 
• 1:21:39 - Bitcoin vs. gold market cap
• 1:23:10 - Rapid fire questions & closing