Off the Block: fixing crypto fundraising with Matt O’Connor

February 20, 2026

Off the Block: fixing crypto fundraising with Matt O’Connor

Crypto fundraising and tokenomics are evolving, and Legion co-founder Matt O’Connor offers his insights into the changing landscape.

In the 10th episode of Off the Block, O’Connor discusses his transition from researcher to builder and explains how Legion is addressing flaws in modern token launches through merit-based, onchain fundraising.

The conversation explores why the industry is moving away from the “low float, high fully diluted valuation” trap, what differentiates Legion’s approach to investor selection, and how the blurring lines between equity and tokens are shaping the next phase of capital markets. The episode closes with a look at the future of tokenization, from the return of compliant public offerings to the need for sustainable, demand-driven token design.

A guide to the episode:

01:18 – Matt’s crypto origin story: Bitcoin and 2017 ICOs
05:39 – Token vs. equity: navigating founder incentives
07:12 – Tokenomics: the misunderstood "demand side"
11:57 – Sprint vs. marathon: building a project vs. launching a token
14:23 – The current state of fundraising: why it’s "fragile"
16:46 – Legion 101: solving compliance and distribution for retail
23:33 – The transparency advantage: using blockchain for capital raises
27:23 – Tokenized equity: merging utility with legal protections
33:33 – SEC precedents and the 2026 “experimentation era”
36:00 – Market brutality: why recent alts are down 80%
39:10 – Legion’s roadmap: matchmaking teams with real value-adders

▶️ Listen to the full episode of Off the Block with Matt O’Connor

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