joey@iosg.vc
iosg.vc · Joined 2025-07-22 · Last active 2026-01-28
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I am a principal investor at IOSG Ventures, a crypto native firm. I want to present to the IC members, what we should prioritize when looking at secondary market deals and propose an example framework. The goal would be to show IC what would be useful, and what would be over complicating. Below l
Jan 28, 04:02 AM
# Secondary Market Deal Framework: The Critical Few Metrics for IOSG Ventures ## Executive Summary This framework establishes a disciplined approach to secondary market deal evaluation, focusing on the **"Critical Few" metrics** that drive institutional decision-making while avoiding analysis paralysis. The core philosophy centers on a **70/30 weighting** between **Fundamentals** (product strength, capital efficiency, supply health) and **Context** (narrative, market cycle), with clear quantit
I resonated with this framework as well, Don't give me such a detailed answer, just give me a basic structure of the piece I can write: 1. Market Regime & Macro Overlay I am a liquidity "maxi." First step is defining in what mode the market is: Risk-Off: I hunt for "alpha" in rare outliers. I sti
Jan 28, 04:13 AM
# Trading Framework for Liquidity "Maxi": The 5-Pillar Approach ## 1. Market Regime & Macro Overlay **Risk-Off Mode**: Hunt for rare outliers with high-conviction scalps featuring tight invalidations and asymmetric upside. Focus on quality over quantity. **Risk-On Mode**: Pivot to pure momentum trading, comfortable with zero-fundamental assets if framework permits. In mania phases, capturing velocity becomes the primary path to outsized returns. ## 2. Narrative Velocity & Sentiment Treat st
What do you think about this framework: ## Abstract The Alt markets have cooled down - What is the point - The critical few framework - Try to avoid analysis paralysis as much as possible - Figure out what is signal, and what is noise - Cycle **Risk-Off Mode**: Hunt for rare out
Jan 28, 04:44 PM
# Evaluating the Secondary Market Framework: A Practitioner's Perspective ## Framework Assessment This framework represents a sophisticated evolution from traditional VC diligence to crypto-native secondary market analysis. The structure effectively balances **rigorous fundamentals** with **market-aware flexibility**, creating a dynamic system that adapts to crypto's unique volatility while maintaining institutional discipline. ## Core Strengths **1. Critical Few Philosophy**: The emphasis o
What do you think about this so far: ## Abstract A lot of non-major tokens have been a result of ‘token plays’ from greedy venture-backed teams or launched from a graveyard of solutions looking for products. The good news is that **the general majority** of alt markets have cooled down significa
Jan 28, 10:12 PM
# Secondary Market Investment Framework Assessment: IOSG Ventures ## Executive Summary This framework represents a sophisticated evolution in crypto secondary market investing, moving beyond traditional VC diligence to embrace the unique advantages of liquid tokens. The core insight—that **secondary markets offer superior information transparency and flexibility** compared to primary rounds—is well-supported by the venture vs. secondary comparison table. The framework successfully balances ins
What are factors to consider when deciding how much size to put into projects
Jan 28, 11:57 PM
# Position Sizing Framework for Secondary Market Investments ## Executive Summary Position sizing in secondary market deals requires a disciplined approach that balances **conviction strength** with **risk management**. Based on the investment framework developed for IOSG Ventures, optimal sizing should be determined by a combination of fundamental strength, market context, and specific risk factors unique to each opportunity. The most critical considerations include the quality of fundamental
Should we make a venture bet on another prediction market with decent growth when we already have polymarkets, kalshi, and a million other prediction markets? Maybe take into account perps, sports betting, casinos, etc. to see if it's ever worth it to bet on a smaller player. I am trying to make a t
Jan 15, 09:10 PM
# XO Markets Venture Investment Thesis ## TL;DR XO Markets represents a **high-risk, asymmetric-upside bet** in an explosively growing but increasingly competitive prediction markets sector. With only $500k pre-seed funding vs. competitors' billions, XO's differentiated permissionless architecture and early traction ($30M volume in ~6 weeks) position it as a potential category disruptor—but faces severe liquidity and regulatory challenges. The prediction markets TAM is expanding rapidly (300%