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E445: AngelList: Why Picking Winners Is the Wrong Way to Invest in Startups

How I Invest with David Weisburd

Hosted by David Weisburd

1h 1m
Transcript

Original podcast

Summary

Written by a model from the transcript; not yet reviewed.

This episode explores how venture capital has evolved into an access-driven market governed by power laws, moving away from the traditional view of picking winners through superior foresight. The guest explains why the best companies are priced efficiently at early stages and how top decile valuations often correlate with a higher probability of generating a 10x return. They discuss the two distinct models for winning in this environment: the cathedral model built by mega-firms and the bazaar model populated by specialized operators. Throughout the conversation, the discussion highlights the structural shift keeping companies private longer and the implications of this delay for both institutional and everyday investors.

  • Seed stage investing is an access game rather than a selection game because the best rounds are efficiently priced upfront. 2:26
  • Early stage rounds with higher initial valuations frequently produce the largest venture outcomes. 3:22
  • The vast majority of venture returns are concentrated in an extremely small percentage of companies per vintage. 14:26
  • Firms without elite brand equity or specialized networks face a challenging environment in the modern venture landscape. 21:15

Chapters

  1. 0:00
    Efficient Capital Market in Venture

    The host explains how efficient market theory applies to venture capital, challenging the belief that VC is purely idiosyncratic.

  2. 1:17
    AngelList Experience and VC Asset Classes

    The guest recounts his time at AngelList, revealing that venture capital splits into seed and later-stage asset classes with different dynamics.

  3. 2:32
    Access Over Selection in Seed Investing

    The discussion shifts to seed investing, emphasizing that success hinges on gaining access to the right tables rather than picking winners.

  4. 3:49
    Empirical Evidence of Valuation Power

    The guest presents data showing that higher early valuations correlate with higher probability of 10x returns, supporting the access thesis.

  5. 11:48
    Fund of Funds and LP Perspective

    The host discusses how LPs can diversify across cathedral and bizarre strategies via fund-of-funds to mitigate missing generational companies.

  6. 18:56
    Building Cathedrals vs. Bizarre Managers

    The conversation explores two strategies: building a cathedral firm for brand-driven access and selecting niche managers for bespoke value-add.

  7. 38:19
    Timing, Bubble, and Discipline in Venture

    The dialogue examines the impossibility of timing market cycles and the importance of disciplined, multi‑round investment strategies.

  8. 45:54
    Future of Retail Access to Private Markets

    The episode concludes with a vision for expanding retail investor access to private startups and the implications for wealth creation.

  9. 48:09
    Emerging Investment Vehicles for Retail

    Discussion of new financial products expanding retail access to venture and listed companies.

  10. 51:07
    AngelList’s Investor Base and Reach

    Analysis of AngelList’s accredited investor numbers and their impact on venture access.

  11. 52:23
    Retail Capital Flow into Private Markets

    Examination of the projected trillions of retail capital entering private markets over the next five years.

  12. 52:59
    AI’s Impact on Venture Growth and Distribution

    Discussion of AI accelerating company growth and the importance of venture capital underwriting.

Highlights

Quotes

  • “the top decile priced companies probability of generating a 10x return is kind of in the 50th decile.”
    Unnamed speaker · 0:12
  • “So if everyone knows the best companies, it's all about how do you access those companies, not who are the best companies?”
    David Weisburd · 0:28
  • “The best companies are, the rounds are oversubscribed. The signals are pretty, pretty clear typically.”
    Unnamed speaker · 3:00
  • “And where, you know, I very much applaud a host of new vehicles have been coming to market.”
    Unnamed speaker · 48:09
  • “Well, it's more than 100,000 because we have our data on how many investors are on Angel List.”
    Unnamed speaker · 49:16
  • “In terms of how much will, I do think there will be a sea change over the next, you know, call it five years.”
    Unnamed speaker · 52:34
  • “I have a simple, uh, way I can press it all down is just more investor freedom, right?”
    Unnamed speaker · 57:41
  • “and then we redeem out on a quarterly basis in tender offers that are not guaranteed.”
    Unnamed speaker · 1:00:29
  • Juniper Square 7:32–7:42
  • Juniper Square 23:50–25:27
  • Square 30:38–31:57

About this episode

What if the biggest advantage in venture capital isn't picking winners, but getting access to them? Erik Syvertsen is GM of Asset Management and Chief Legal Officer at AngelList and Chairman of USVC. Drawing on AngelList's extensive venture investment data, Erik explains why seed and growth investing operate like two different asset classes, why the best startups often command higher valuations from the beginning, and how access drives venture returns. We explore the power law, why doubling down on winners matters, the two strategies for building successful venture portfolios, and the challenges of selling investments in breakout companies. Erik also discusses how USVC aims to expand access to private markets as companies like OpenAI, Anthropic, and SpaceX create enormous value before going public.

Transcript

0:00
1:01:23

11,902 words · 2 speakers

Speaker names marked are inferred from speaking time and the show’s known hosts — they are not voice-verified.

Topics

  • Angel List
  • USVC
  • Angelus
  • Robinhood
  • SEC
  • iCapital
  • 40 Act
  • SPVs
  • Hive
  • Forge

Page updated · transcript and summary are machine-generated