Gary Leland on Starting Early, From Wallpaper to BitBlockBoom
November 14, 2026
In this First Principles episode from Onramp Media, host Cam Stromme talks with Gary Leland, founder of the bitcoin conference BitBlockBoom. Gary recounts his early-web ventures, why he built a bitcoin-only event, and his thoughts on longevity.
Gary Leland has a habit of showing up before everyone else. He put a wallpaper store online in 1996, built the first website for girls' fastpitch softball, and launched Podcast Pickle in the early days of podcasting. He then found bitcoin and started BitBlockBoom, a bitcoin-only conference he kept running through COVID. Gary tells Cam Stromme why he thinks the real value of a conference is in the hallway, how he thinks about holding bitcoin and who should know about it, and why he stopped trying to orange pill friends and family. They close on the 200 Year Life Project, longevity escape velocity, and Gary's view of how a fixed-supply money relates to planning for a longer life.
Chapters
00:00 - Gary Leland, founder of BitBlockBoom 01:03 - Selling wallpaper online in 1996 06:08 - The first website for girls' fastpitch softball 08:50 - Podcast Pickle and the early days of podcasting 13:39 - Called crazy again: "made up internet money" 14:25 - Why BitBlockBoom went Bitcoin only 17:35 - How one conference changes careers 18:55 - Why the hallway beats the sessions 21:53 - Holding a Bitcoin conference through COVID 27:30 - What ten years of Bitcoin culture taught him 31:13 - Multisig, physical attacks and who should know you hold Bitcoin 36:08 - Wallet exploits and Bitcoin for the grandkids 40:05 - Why he stopped trying to orange pill people 45:37 - BitBlockBoom in the Fort Worth Stockyards 47:56 - The 200 Year Life Project 50:42 - Can Bitcoin fund a much longer life? 53:33 - Longevity escape velocity 58:05 - Gary's Parting Thoughts
Frequently Asked Questions
Who is Gary Leland?
Gary Leland is the founder of BitBlockBoom, a bitcoin-only conference. The episode opens with his background (00:00) and his early-web ventures, including an online wallpaper store in 1996 (01:03) and Podcast Pickle (08:50).
Why did BitBlockBoom focus only on bitcoin?
Gary explains his reasons for making BitBlockBoom a bitcoin-only event at 14:25 and why he thinks conferences change careers (17:35). He also describes running the event through COVID at 21:53.
What is the 200 Year Life Project?
Gary introduces the 200 Year Life Project at 47:56 and discusses longevity escape velocity at 53:33. These are Gary's own views and this is the guest's framing, not investment advice from Onramp.
What does Gary say about holding bitcoin and privacy?
At 31:13 Gary discusses multisig, physical attacks and who should know you hold bitcoin. At 40:05 he explains why he stopped trying to orange pill people. These are personal views, not recommendations from Onramp.
This episode is editorial and educational content. Onramp does not provide tax, legal, or investment advice. Bitcoin is volatile and may lose value. Past performance does not guarantee future results.