Jun 8, 2022 · 58m · news
Ian Lee: Why DAOs Will Replace Venture Capital; Biggest Threat to Web3 | 20VC #893 · 20VC with Harry Stebbings
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of the 20VC podcast, host Harry Stebbings interviews Ian Lee, co-founder of Syndicate, to discuss how decentralized autonomous organizations (DAOs) are transforming venture capital, the strategic failures of traditional VCs in Web3, and the cultural and structural shifts required for decentralized technologies to achieve mainstream adoption.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 10.2% of the talking time here. How this is scored →
Harry as informed peer 3.6 Guest teaching 3.0 Guest disagreement 0.9 Harry pushing back 3.1
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 28:20 Ian's critique of Web2 wealth centralization
Ian forcefully critiques traditional Web2 platforms like Uber, pointing out the stark unfairness of drivers sleeping in cars while value accrues exclusively to central founders and VCs.
Hardest push from Harry ▶ 13:01 Harry calling out DAO reinvention of traditional VCHarry bluntly rejects the hype around DAO governance by pointing out that delegating decisions to four admins is identical to Arthur Rock's 40-year-old venture fund model.
Biggest teaching moment ▶ 14:30 Ian explaining skeuomorphism in technology adoptionIan reframes Harry's critique of DAOs by explaining how new technological paradigms initially mimic old legal and organizational structures before evolving into novel forms.
Harry holds his own ▶ 30:32 Harry countering web3 optimism with Mark Carney quoteHarry demonstrates high macro-economic awareness by citing former Bank of England governor Mark Carney to challenge Ian's assertion that web3 will naturally create greater income equality.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Ian Lee's Journey from Builder to Investor | 1 | 1 | 0 | 1 | Harry opens with friendly background questions about Ian's path from engineering/consulting into VC. The dynamic is polite and conversational with no significant challenge or deep technical debate. | |
| The Genesis of Syndicate | 1 | 2 | 0 | 0 | Harry prompts Ian to explain how Syndicate originated. Ian shares how the flawed ICO boom of 2017 inspired software primitives for community-based investing without host interruption. | |
| Why DAOs are the Future of Venture Capital | 3 | 4 | 1 | 2 | Harry references prior guest conversations and admits feeling terrified by Ian's claim that DAOs are the future of VC. Ian systematically breaks down the multi-decade evolution from solo capitalists to angel collectives and DAOs. | |
| The Organizational Design and Skeuomorphism of DAOs | 6 | 5 | 2 | 7 | Harry presses Ian directly, pointing out that DAOs delegating decisions to four admins are simply reinventing 40-year-old venture fund structures. Ian accepts the premise and reframes it using the concept of skeuomorphism in tech adoption. | |
| Winners and Losers in Web3 Investing | 5 | 3 | 1 | 4 | Harry challenges whether smaller follower funds really need full web3 technical infrastructure to succeed. Ian agrees that co-investing alongside top leads remains viable while insisting native capabilities offer the real long-term edge. | |
| Web3 as the Next Era of the Internet | 7 | 4 | 2 | 6 | Harry challenges Ian's optimistic web3 vision by citing former Bank of England governor Mark Carney on how tech shifts historically increase inequality, and critiques terrible current crypto UX. Ian candidly concedes that technology is agnostic and can amplify inequality if poorly designed. | |
| Storytelling and Inclusivity in Web3 | 4 | 3 | 1 | 3 | Harry asks whether web3's main barrier is technical infrastructure or a failure in basic storytelling. Ian agrees and criticizes the insular 'us vs them' tribalism that currently deters mainstream participation. | |
| The Biggest Threats and the Hype Cycles of Web3 | 3 | 3 | 1 | 4 | Harry expresses cynical frustration at fair-weather VC tourists hosting web3 dinners. Ian shares perspective from surviving multiple boom-and-bust cycles, noting that time eventually filters out the tourists from true builders. | |
| Quick Fire Round | 2 | 2 | 0 | 1 | A relaxed quickfire round touching on book recommendations, NFT timing mistakes, cap table complexities, and capital deployment metrics. The dynamic is playful and warm. |
Statements from this episode (20)
Ian Lee: Investing Feels One or Two Derivatives Removed From Building
“When I got exposed to investing, it for me was very removed, I guess, from the process of building. It was like at least one or two derivatives off From the actual work that was happening.”
Ian Lee: Traditional VC Centralizes Wealth and Control in Web3 Networks
“The traditional venture capital model was actually centralizing wealth and control and ownership of these networks.”
Ian Lee: ICOs Created a Democratic Model for Tech Investment
“One of the things that was really profound about ICOs was it was a completely open and democratic model to invest in technology.”
Ian Lee: Solo Capitalists Struggle to Support Portfolios Compared to Traditional VCs
“The angel investing model and the solo capitalist model doesn't do a great job of supporting portfolio companies, right? So in order to compete with traditional venture firms that have a lot more resources, And areas of support and areas of like business devel…”
Ian Lee: Web3 and DAOs Will Power the Future of Venture Capital
“And if you believe that, then the end state likely of this trend that's been happening for more than two decades is likely going to lead to some sort of model and system that will be powered by web three endowed technologies behind them. And that is the bet th…”
Ian Lee: DAOs With Explicit Mandates Are Vastly More Successful
“Purposeful DAOs, where they have explicit mandates and very specific ones. Tend to do much better. So if you have, like, a DAO that's just kind of very generic and doesn't really have a clear purpose, those ones have a much harder time sustaining themselves, w…”
Ian Lee: DAOs Will Spawn Novel Organizational Models Beyond Legacy Structures
“As it relates specifically to DAOs I, we do believe that DAOs are going to lead to fundamentally new organizations that don't easily or don't exist in today's world. A good example of this is like, you know, some of these DAOs that are popping up right now in …”
Ian Lee: Novel DAO Markets Will Surpass Legacy Entity Transformations
“Over the long run, when we're thinking about 10 to 20 year plus time spans, it's likely that the new to world markets are actually going to outsize the existing ones, and that's absolutely what we think Syndicate is going to do.”
Ian Lee: VCs Without Web3 Capabilities Will Lose Their Competitive Edge
“VC funds that don't build those capabilities, whether they are dedicated crypto funds or not, are going to not be able to maintain an edge and keep up with the pace of innovation and the, I guess, innovations that are coming out of web three.”
Ian Lee: Network-Participating Investors Will Win in Crypto Over 5-10 Years
“At a high level, if you project this out again, over five to 10 year plus timescale, the investors who are more participatory in these networks that can actively get involved natively with these technologies are going to be the ones that win.”
Ian Lee: Copy Trading Electric Capital Is a Top Crypto Investing Strategy
“I think copy trading of each and electric capital is probably one of the best strategies that anyone can have.”
Ian Lee: Kyle Samani and Chris Dixon Popularized 'Web3' Around 2017
“The people who originally talked about Web Three were people like Kyle Simani of Multicoin and also Chris Dixon at A-sixteen Z, probably around like, 2017, 20 18, and that was, I mean, that was way ahead of its time, but for people that were kind of following …”
Ian Lee: Web3 Can Centralize Wealth Just as Effectively as Decentralizing It
“So in the same way, like, you know, taking social media as an example, I think web three has that same potential, and you're, and you we've been seeing that, right, for the last decade since it's been around, which is that web three, like any technology, has t…”
Ian Lee: Early Web3 Startups Failed Due to Missing Infrastructure, Not Storytelling
“Cello is, is one that I have high hopes for, but there have been, you know, hundreds of startups that unfortunately were going after really important missions, and were actually telling very good narratives about how they were going to, for example, bank the u…”
Ian Lee: Mt. Gox Collapse Set the Crypto Industry Back Three Years
“Mt. Gox set the Bitcoin industry and the crypto industry back by, you know, at least two to three years.”
Ian Lee: Only 5% to 10% of Hype-Cycle Entrants Stay in Crypto
“Out of the 90, 95% of people that came and went within a matter of months, there were five to 10% of people that actually came in for the right reasons, and they're incredible”
Ian Lee: Incumbents Fail by Dismissing Tech That Disguises Business Model Shifts
“And my main takeaway from that book and all of my work over the last two decades is that it's because incumbents Fail to realize that a technological innovation often comes with a business model innovation behind it, and they get, they dismiss the technologica…”
Ian Lee: NFT-Powered Spotify and YouTube Alternatives Will Emerge by 2024
“So good example of this is that I think that like NFT powered commerce in Web three, NFT powered digital media and various kind of social media platforms. That I knew or believed were gonna happen in 10 years or so, I think are now possible in the next two to …”