Episode Summary
Executive Summary: Nick Tomaino traces his path from early Bitcoin curiosity and Coinbase to founding One Confirmation, arguing that crypto venture is being distorted by oversized funds, hype, and perception games. He defends a disciplined, early-stage strategy, praises NFTs as creator-aligned infrastructure, and warns that truthful outcomes in crypto, FTX, and venture fund performance only become clear over time.
Main Topics: Nick Tomaino’s origin story in crypto (Priority: 5/5): He explains how an internet-first mindset, early Bitcoin forum discovery, and belief in crypto’s social significance led him from Coinbase into venture investing. Founding One Confirmation and early fundraising (Priority: 5/5): After being pushed out of Coinbase, he used personal brand, writing, and event-building to raise his first fund and establish One Confirmation as a crypto-native seed firm. Crypto venture strategy and fund sizing (Priority: 5/5): He argues for staying small, early-stage, and disciplined, saying many crypto funds raised far too much capital and drifted into lower-quality strategies. Returns, liquidity, and transparency in venture (Priority: 4/5): He says venture investors should publish returns more regularly and should take liquidity off the table when winners emerge, rather than hiding behind fund-size prestige. FTX, perception, and accountability (Priority: 5/5): He frames FTX as not just financial fraud but a 'fraud of perception' involving media, politicians, regulators, and investors, and says the truth will emerge slowly. NFTs, OpenSea, and creator-owned brands (Priority: 5/5): He remains bullish on NFTs as an internet-native business model for creators and as a new asset class, using OpenSea and CryptoPunks as key examples. Contrarianism, dogma, and what he got wrong (Priority: 4/5): He describes his independence of thought as a strength while acknowledging it can become dogmatic, citing Solana and prediction markets as areas where he may be overly principled or early.
Key Arguments: A strong personal brand, timing, and credibility in a fast-moving niche can substitute for traditional venture pedigree when raising a first fund. Crypto funds should stay small and focused on early-stage investing; oversized funds encourage mediocre deployment and management-fee behavior. Publishing returns would make venture more honest by shifting attention from fund size and prestige to actual performance. Some crypto VCs exploit a token-creation and retail-hype cycle; FTX exemplified a broader 'fraud of perception,' not just a single bad actor. NFTs are valuable because they align incentives between creators and supporters and can create user-owned brands and new forms of fan participation. OpenSea remains strategically important because if NFTs expand, an on-ramp marketplace becomes valuable even if near-term volumes are weak. Conviction should be backed by capital allocation; in hindsight, he should have been more aggressive in OpenSea. Independent thinking and emotional grounding are competitive advantages, but dogmatism can cause missed opportunities, like Solana or prediction markets. Prediction markets could be one of crypto’s most important long-term applications because they turn information into global, tradable probabilities.
Data Points: First fund size: $26 million - One Confirmation’s inaugural fund launched in 2017 Second fund size: $50 million - One Confirmation fund two, 2019 vintage Third fund size: $130 million - One Confirmation fund three, 2021 vintage NFT fund size: $80 million - One Confirmation’s dedicated NFT fund Reported LP returns: 5.13x cash back to LPs - Nick’s first fund performance, cited from his tweet Time to returns measurement: 6 years - The 5.13x result was achieved in about six years Fund one investments: 22 investments - He said fund one had 22 portfolio companies Initial check size range: $500K to $1M - Target initial investment size for early-stage crypto deals Phishing loss: $50,000 - He lost all his Bitcoin in an early Coinbase phishing attack OpenSea initial investment: $500K - Initial One Confirmation investment in OpenSea OpenSea current position: Majority still owned - He said they still own most of their OpenSea position while taking some chips off the table OpenSea paper value change: Down significantly; roughly in the right ballpark of $1B–$5B lower than peak - He indicated the mark is materially below prior highs without giving an exact figure Liquidity taken in winners: 10% to 30% - He said they sold this amount of some big winners at later stages NFT resurgence horizon: 3 to 5 years - His estimated timeframe for a meaningful NFT comeback Consumer event size: 400 people - Token Summit attendance in one of his early brand-building efforts
Pivotal Quotes: "Way too much money was raised. People raised billion-dollar funds that just had no unique insights." — Harry Stebbings opening / framing Nick Tomaino's thesis: Sets up the core criticism of oversized crypto funds and institutional FOMO "The truth reveals itself in time." — Nick Tomaino: His recurring theme about FTX, venture performance, and market narratives "NFTs are an incredible business model for creators on the internet." — Nick Tomaino: His central bullish thesis on NFTs and creator monetization
Implications: The episode argues for smaller, more disciplined crypto funds, more transparent performance, and skepticism toward hype-driven narratives. It also suggests NFTs and prediction markets may matter more long term than their current market activity implies.