EPISODE · Apr 9, 2026 · 46 MIN
Brian Wong: I Solved the AI Investment Playbook
from The Rollup · host Where digital assets meet capital markets. Hosted by Robbie & Andy
Brian Wong joins this episode of AI Supercycles to break down his barbell investment strategy for the AI boom, why the real AI x digital assets trade is in stablecoin app layer companies, and much more.Brian Wong is a serial entrepreneur and co-founder of Ascii Ventures, a fund focused on behind-the-scenes infrastructure and boring tech that powers daily life. The Rollup is where the leaders of digital assets and finance converge. Live from the financial capital of the world.Timestamps:00:00 Intro01:05 Ascii Ventures Thesis03:32 Barbell Investment Strategy05:35 Secondary Markets Opportunity07:21 Digital Assets Stablecoin Focus09:28 Emerging Markets Adoption10:26 OpenAI & Anthropic Valuations15:09 AI Services Comeback18:51 Prompt-Less AI Explained20:45 Agents Buying Things For You24:29 From Prompting to Prompt-Less28:13 AI Trust Gap Problem31:23 AI as Amplifier Not Replacement33:22 AI Ethics & Bias Risk38:46 AI Psychosis & LLM Flattery42:12 Education System Is Broken45:34 How To Stay HumanWebsite: https://therollup.co/Spotify: https://open.spotify.com/show/1P6ZeYd...Podcast: https://therollup.co/category/podcastFollow us on X: https://www.x.com/therollupcoFollow Rob on X: https://www.x.com/robbiek__Follow Andy on X: https://www.x.com/ayyyeandyJoin our TG group: https://t.me/+TsM1CRpWFgk1NGZhThe Rollup Disclosures: https://goodidea.ventures𝗗𝗜𝗦𝗖𝗟𝗔𝗜𝗠𝗘𝗥: 𝘐𝘯𝘷𝘦𝘴𝘵𝘪𝘯𝘨 𝘪𝘯 𝘤𝘳𝘺𝘱𝘵𝘰𝘤𝘶𝘳𝘳𝘦𝘯𝘤𝘺 𝘢𝘯𝘥 𝘋𝘦𝘍𝘪 𝘱𝘭𝘢𝘵𝘧𝘰𝘳𝘮𝘴 𝘤𝘰𝘮𝘦𝘴 𝘸𝘪𝘵𝘩 𝘪𝘯𝘩𝘦𝘳𝘦𝘯𝘵 𝘳𝘪𝘴𝘬𝘴 𝘪𝘯𝘤𝘭𝘶𝘥𝘪𝘯𝘨 𝘵𝘦𝘤𝘩𝘯𝘪𝘤𝘢𝘭 𝘳𝘪𝘴𝘬, 𝘩𝘶𝘮𝘢𝘯 𝘦𝘳𝘳𝘰𝘳, 𝘱𝘭𝘢𝘵𝘧𝘰𝘳𝘮 𝘧𝘢𝘪𝘭𝘶𝘳𝘦 𝘢𝘯𝘥 𝘮𝘰𝘳𝘦. 𝘈𝘵 𝘤𝘦𝘳𝘵𝘢𝘪𝘯 𝘱𝘰𝘪𝘯𝘵𝘴 𝘵𝘩𝘳𝘰𝘶𝘨𝘩𝘰𝘶𝘵 𝘵𝘩𝘪𝘴 𝘤𝘩𝘢𝘯𝘯𝘦𝘭, 𝘸𝘦 𝘮𝘢𝘺 𝘦𝘢𝘳𝘯 𝘢 𝘤𝘰𝘮𝘮𝘪𝘴𝘴𝘪𝘰𝘯 𝘰𝘳 𝘧𝘦𝘦 𝘢𝘴 𝘢 𝘴𝘱𝘰𝘯𝘴𝘰𝘳𝘴𝘩𝘪𝘱, 𝘪𝘧 𝘵𝘩𝘪𝘴 𝘪𝘴 𝘵𝘩𝘦 𝘤𝘢𝘴𝘦 𝘸𝘦 𝘸𝘪𝘭𝘭 𝘢𝘭𝘸𝘢𝘺𝘴 𝘮𝘢𝘬𝘦 𝘴𝘶𝘳𝘦 𝘪𝘵 𝘪𝘴 𝘤𝘭𝘦𝘢𝘳. 𝘞𝘦 𝘢𝘳𝘦 𝘴𝘵𝘳𝘪𝘤𝘵𝘭𝘺 𝘢𝘯 𝘦𝘥𝘶𝘤𝘢𝘵𝘪𝘰𝘯𝘢𝘭 𝘤𝘰𝘯𝘵𝘦𝘯𝘵 𝘱𝘭𝘢𝘵𝘧𝘰𝘳𝘮, 𝘯𝘰𝘵𝘩𝘪𝘯𝘨 𝘸𝘦 𝘰𝘧𝘧𝘦𝘳 𝘪𝘴 𝘧𝘪𝘯𝘢𝘯𝘤𝘪𝘢𝘭 𝘢𝘥𝘷𝘪𝘤𝘦. 𝘞𝘦 𝘢𝘳𝘦 𝘯𝘰𝘵 𝘱𝘳𝘰𝘧𝘦𝘴𝘴𝘪𝘰𝘯𝘢𝘭𝘴 𝘰𝘳 𝘭𝘪𝘤𝘦𝘯𝘴𝘦𝘥 𝘢𝘥𝘷𝘪𝘴𝘰𝘳𝘴.
What this episode covers
Brian Wong joins this episode of AI Supercycles to break down his barbell investment strategy for the AI boom, why the real AI x digital assets trade is in stablecoin app layer companies, and much more.Brian Wong is a serial entrepreneur and co-founder of Ascii Ventures, a fund focused on behind-the-scenes infrastructure and boring tech that powers daily life. The Rollup is where the leaders of digital assets and finance converge. Live from the financial capital of the world.Timestamps:00:00 Intro01:05 Ascii Ventures Thesis03:32 Barbell Investment Strategy05:35 Secondary Markets Opportunity07:21 Digital Assets Stablecoin Focus09:28 Emerging Markets Adoption10:26 OpenAI & Anthropic Valuations15:09 AI Services Comeback18:51 Prompt-Less AI Explained20:45 Agents Buying Things For You24:29 From Prompting to Prompt-Less28:13 AI Trust Gap Problem31:23 AI as Amplifier Not Replacement33:22 AI Ethics & Bias Risk38:46 AI Psychosis & LLM Flattery42:12 Education System Is Broken45:34 How To Stay HumanWebsite: https://therollup.co/Spotify: https://open.spotify.com/show/1P6ZeYd...Podcast: https://therollup.co/category/podcastFollow us on X: https://www.x.com/therollupcoFollow Rob on X: https://www.x.com/robbiek__Follow Andy on X: https://www.x.com/ayyyeandyJoin our TG group: https://t.me/+TsM1CRpWFgk1NGZhThe Rollup Disclosures: https://goodidea.ventures𝗗𝗜𝗦𝗖𝗟𝗔𝗜𝗠𝗘𝗥: 𝘐𝘯𝘷𝘦𝘴𝘵𝘪𝘯𝘨 𝘪𝘯 𝘤𝘳𝘺𝘱𝘵𝘰𝘤𝘶𝘳𝘳𝘦𝘯𝘤𝘺 𝘢𝘯𝘥 𝘋𝘦𝘍𝘪 𝘱𝘭𝘢𝘵𝘧𝘰𝘳𝘮𝘴 𝘤𝘰𝘮𝘦𝘴 𝘸𝘪𝘵𝘩 𝘪𝘯𝘩𝘦𝘳𝘦𝘯𝘵 𝘳𝘪𝘴𝘬𝘴 𝘪𝘯𝘤𝘭𝘶𝘥𝘪𝘯𝘨 𝘵𝘦𝘤𝘩𝘯𝘪𝘤𝘢𝘭 𝘳𝘪𝘴𝘬, 𝘩𝘶𝘮𝘢𝘯 𝘦𝘳𝘳𝘰𝘳, 𝘱𝘭𝘢𝘵𝘧𝘰𝘳𝘮 𝘧𝘢𝘪𝘭𝘶𝘳𝘦 𝘢𝘯𝘥 𝘮𝘰𝘳𝘦. 𝘈𝘵 𝘤𝘦𝘳𝘵𝘢𝘪𝘯 𝘱𝘰𝘪𝘯𝘵𝘴 𝘵𝘩𝘳𝘰𝘶𝘨𝘩𝘰𝘶𝘵 𝘵𝘩𝘪𝘴 𝘤𝘩𝘢𝘯𝘯𝘦𝘭, 𝘸𝘦 𝘮𝘢𝘺 𝘦𝘢𝘳𝘯 𝘢 𝘤𝘰𝘮𝘮𝘪𝘴𝘴𝘪𝘰𝘯 𝘰𝘳 𝘧𝘦𝘦 𝘢𝘴 𝘢 𝘴𝘱𝘰𝘯𝘴𝘰𝘳𝘴𝘩𝘪𝘱, 𝘪𝘧 𝘵𝘩𝘪𝘴 𝘪𝘴 𝘵𝘩𝘦 𝘤𝘢𝘴𝘦 𝘸𝘦 𝘸𝘪𝘭𝘭 𝘢𝘭𝘸𝘢𝘺𝘴 𝘮𝘢𝘬𝘦 𝘴𝘶𝘳𝘦 𝘪𝘵 𝘪𝘴 𝘤𝘭𝘦𝘢𝘳. 𝘞𝘦 𝘢𝘳𝘦 𝘴𝘵𝘳𝘪𝘤𝘵𝘭𝘺 𝘢𝘯 𝘦𝘥𝘶𝘤𝘢𝘵𝘪𝘰𝘯𝘢𝘭 𝘤𝘰𝘯𝘵𝘦𝘯𝘵 𝘱𝘭𝘢𝘵𝘧𝘰𝘳𝘮, 𝘯𝘰𝘵𝘩𝘪𝘯𝘨 𝘸𝘦 𝘰𝘧𝘧𝘦𝘳 𝘪𝘴 𝘧𝘪𝘯𝘢𝘯𝘤𝘪𝘢𝘭 𝘢𝘥𝘷𝘪𝘤𝘦. 𝘞𝘦 𝘢𝘳𝘦 𝘯𝘰𝘵 𝘱𝘳𝘰𝘧𝘦𝘴𝘴𝘪𝘰𝘯𝘢𝘭𝘴 𝘰𝘳 𝘭𝘪𝘤𝘦𝘯𝘴𝘦𝘥 𝘢𝘥𝘷𝘪𝘴𝘰𝘳𝘴.
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Brian Wong: I Solved the AI Investment Playbook
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