Feb 10, 2016 · 24m · 20vc
20VC: The First Online Venture Fund Built On AngelList with Dustin Dolginow @ Maiden Lane
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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 20 Minute VC, host Harry Stebbings speaks with Dustin Dolginow, General Partner at Maiden Lane, about how AngelList syndicates are unbundling traditional venture capital and modernizing startup investing.
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 24.4% of the talking time here. How this is scored →
Harry as informed peer 2.1 Guest teaching 1.7 Guest disagreement 0.9 Harry pushing back 0.6
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 16:19 Rejecting complete democratization
Dustin directly disagrees with Harry's premise about complete democratization, arguing that elite entrepreneurs will never want thousands of investors on their cap table.
Hardest push from Harry ▶ 12:21 Probing non-standard VC feesHarry interrogates Dustin on Maiden Lane's unusual 30% carry and zero management fee structure, asking if it is strange or trendsetting in the VC industry.
Biggest teaching moment ▶ 8:12 Explaining native apps vs platformsDustin educates Harry on how to think about Maiden Lane's relationship with AngelList by using the analogy of Uber operating on Apple's iOS.
Harry holds his own ▶ 12:21 Demonstrating specific fee structure knowledgeHarry demonstrates deep knowledge of venture capital fund economics by calling out Maiden Lane's precise 30% carry and zero management fee structure.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Handover and Podcast Welcome | 1 | 0 | 0 | 0 | Harry introduces the guest and asks standard background questions about Dustin's transition from finance to startup operations and VC. The interaction is welcoming and conversational without any challenge or expert probing. | |
| The Story and Philosophy Behind Maiden Lane | 1 | 2 | 0 | 0 | Dustin details the origin story of Maiden Lane and its connection to AngelList. Harry listens and lets the guest explain the fund's background and name backstory without pushing back. | |
| Unbundling Venture Capital and Funds as Containers | 3 | 3 | 1 | 1 | Harry clarifies that Maiden Lane is not an AngelList fund itself, prompting Dustin to offer an illuminating metaphor comparing Maiden Lane on AngelList to Uber on Apple's iOS platform and explaining funds as containers. | |
| Maiden Lane's Investment Mechanics and Economic Model | 5 | 2 | 0 | 2 | Harry shows specific knowledge of Maiden Lane's fund terms, citing their 30% carry model compared to standard 20% and zero management fee structure. He presses on whether this dynamic is unusual in VC. | |
| Modernizing Capital Allocation in Venture Capital | 2 | 2 | 2 | 0 | Dustin politely pushes back on Harry's premise that Maiden Lane has already established itself as a fantastic fund, noting they still need to return capital to LPs. | |
| The Long-Term Future of Venture Capital | 2 | 3 | 3 | 1 | When Harry asks if venture capital will see complete democratization, Dustin flatly disagrees, explaining that elite founders will not want thousands of people on their cap tables. | |
| Product-First Investing and Founder Insights | 1 | 0 | 0 | 0 | A standard quickfire segment covering product philosophy, favorite sectors, and personal recommendations. The dynamic is completely collaborative and rapid-fire. |
Statements from this episode (11)
Atlas Venture led AngelList's Series A and all subsequent rounds
“Atlas would end up leading the Series A for AngelList very quietly. And have invested in every round since, and I think just continue to drink the Kool-Aid around online investing.”
Maiden Lane raised a $25M fund to invest in AngelList syndicates
“And so we raised twenty-five million dollars. We named the fund Maiden Lane.”
Venture capital knowledge will become distributed rather than insider-only
“Maiden Lane is being built and AngelList is being built, you know, in the middle of a city center of a major city, and I think that's sort of the bigger trend of where venture is going. It is no longer going to be a skill set or knowledge of the very few. It's…”
Maiden Lane originally planned to make half its deals offline
“Initially, we didn't even think there would be enough deal flow on AngelList, and so we put it in our documents that we would do half the deals offline in a more traditional manner, and then half online, kind of waiting for the platform to scale.”
Maiden Lane deploys 95% of its investments through AngelList syndicates
“95% of the investments that we make are done through AngelList, and specifically through syndicates.”
Maiden Lane charges 30% carry to share economics with syndicate leads
“The reason we asked for 30% carried interest is because we share 15 to 20% of that carried interest with syndicate leads.”
Maiden Lane opened a live-work loft for part-time syndicate leads
“One of our first things that we did was we opened a live work loft so that people could do meetings and host dinners and just kind of a third space because most all the syndicate leads have a full-time job, right?”
Consensus VC decisions will decline as conviction investing and LP directs grow
“We're going to see three pretty basic models emerge for how decisions are made, all the way up from LPs down, down to small seed funds. And the three buckets are going to be consensus-based decision-making, and that's every fund that, you know, has pretty much…”
Top VC firms will be forced to adapt to new funding models
“Sequoia, Benchmark, Andreessen Horowitz, they're not going away anytime soon. This isn't like, we're out to beat them and kill them. Not in the same way Airbnb is not going to delete hotels overnight. It's going to change how hotels work. I think that's a bett…”
Prescription delivery is the most overhyped tech sector
“Probably prescription delivery is amazing. It went from like one company to six in three months. It was wild to watch.”
Canada's tech ecosystem is thriving due to a lower cost of living
“This probably is in the sector, but I think Canada for the last two years deserves full credit for just really slaying it. I think it's an indication of how important cost of living is to young companies getting their start. And Canada as a country is just fro…”