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Scott Kupor12 July 2019

Scott Kupor Discusses Technology Startups

4Frameworks
15Insights

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Frameworks in this episode

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Myth Buster· 1

Myth Buster12:22

The Average Venture Fund Is Not an Exceptional Investment

The episode challenges venture capital's glamorous reputation by noting that aggregate ten-year returns had trailed the Nasdaq. Performance varies enormously because access to a small number of winning companies separates elite funds from mediocre ones.

  • Aggregate venture returns can lag public equities
  • Performance dispersion between venture funds is extreme
  • Early access to a winner can determine fund-level outcomes
  • The asset class's average conceals a small set of exceptional managers

“venture capital is not an especially good investment.”

Barry Ritholtz · 12:22

“the variance between good performance and bad performance is really high”

Scott Kupor · 12:50
#venture returns#nasdaq#fund performance#private markets

Hot Take· 2

Hot Take28:27

A $100 Billion Fund Changes Investor Incentives

The SoftBank Vision Fund operated at unprecedented scale and gave its staff a clear incentive to deploy capital. Kupor notes that its lower return hurdle could rationally support higher purchase prices than a conventional venture fund could afford, even if the eventual results remained uncertain.

  • The Vision Fund was approximately $100 billion
  • Fund size creates strong deployment incentives
  • Different costs of capital support different acceptable prices
  • Traditional venture investors may need roughly three times invested capital per fund cycle

“people do what their incentives are, right”

Scott Kupor · 29:19

“they have a lower kind of return hurdle. So in theory, they could afford to pay more than maybe somebody like us could pay for…”

Scott Kupor · 29:37
#softbank#vision fund#incentives#cost of capital
Hot Take50:36

Why Manager Diversification Can Hurt Venture Returns

Kupor argues that limited partners can damage performance by spreading allocations across weaker venture managers. Because returns are highly concentrated and access to elite firms is limited, moving down successive tiers can cause results to converge toward the mediocre industry average.

  • Top venture managers are difficult for new limited partners to access
  • Performance is concentrated among a small set of firms
  • Adding lower-tier managers can dilute exposure to exceptional performers
  • Manager diversification differs from portfolio diversification inside a fund

“Diversification turns out to be a bad strategy in venture”

Scott Kupor · 50:43

“you want to probably double down your money on those folks as as to actually, you know, kind of diverse buying.”

Scott Kupor · 50:54
#limited partners#manager selection#diversification#venture returns

Explainer· 8

Explainer07:35

Why Founders and VCs Start With Unequal Information

Kupor explains that venture firms negotiate thousands of deals while even experienced founders may raise money only several times. His book aims to reduce this information asymmetry so founders can understand venture incentives, terms, and relationship dynamics.

  • VCs accumulate far more transaction experience than founders
  • Repeated founder questions reveal a persistent knowledge gap
  • The asymmetry can create fear of being exploited
  • Greater transparency can improve founder-investor relationships

“there's just not a level playing field from an information perspective”

Scott Kupor · 08:14

“if we could demystify that and hopefully level of playing field, then maybe it helps have a better relationship between entrepreneurs and vcs”

Scott Kupor · 08:32
#fundraising#information asymmetry#founders#venture capital
Explainer15:05

How Y Combinator and Cloud Computing Shifted Power to Founders

Two changes weakened venture capitalists' old role as gatekeepers: startups became dramatically cheaper to launch, and Y Combinator taught founders how the financing process worked. More seed firms then built founder relationships before traditional venture funds could reach them.

  • Cloud infrastructure reduced startup capital requirements
  • Y Combinator educated founders about a formerly opaque process
  • Hundreds of seed firms entered the market
  • Capital abundance increased competition among venture firms
  • Founder bargaining power rose as information and funding became more available

“capital was a scarce resource. The vcs had it”

Scott Kupor · 16:38

“you could now start companies for a lot less money.”

Scott Kupor · 17:42
#y combinator#cloud computing#seed funding#founders
Explainer21:35

Why Founders Increasingly Control Startup Boards

Kupor describes how venture firms still receive board seats and protective voting rights, but less often control a majority of the board. This changes the relationship and reduces investors' unilateral ability to remove founders or chief executives.

  • Major venture investors typically receive a board seat
  • Preferred-stock rights cover financing and company-sale decisions
  • VC-controlled boards were more common historically
  • Founder-controlled boards have become increasingly common
  • Board composition changes the balance of power

“vcs don't control boards anymore like they used to”

Scott Kupor · 21:53

“we see more and more boards where the founders kind of control them”

Scott Kupor · 22:48
#boards#founder control#governance#venture capital
Explainer23:23

Why Technology Companies Stay Private for Twice as Long

Kupor distinguishes the contemporary private-capital boom from the dot-com IPO bubble. Large pools of growth capital have moved into late-stage private rounds, allowing companies to postpone public listings from roughly six years after founding to ten or twelve years.

  • Dot-com companies often went public with very little revenue
  • Modern technology IPO candidates tend to have much greater revenue
  • Seed capital is abundant but remains a small share of total venture capital
  • The largest influx has occurred in late-stage private rounds
  • Public-market growth capital has migrated into private markets

“Today that's about ten to twelve years.”

Scott Kupor · 25:11

“you've pretty much basically doubled in the last decade the time it's taking for companies go public.”

Scott Kupor · 25:13
#ipos#late-stage funding#private markets#growth capital
Explainer33:37

Andreessen Horowitz's Unbundled Venture-Partner Model

Andreessen Horowitz separates investment judgment and board work from specialist operating support. General partners source deals, decide investments, and serve on boards, while dedicated teams help portfolio companies recruit executives, reach customers, and accelerate sales.

  • General-partner capacity is constrained by board seats
  • Specialist teams handle recruiting and commercial introductions
  • The model avoids asking investors to perform work outside their expertise
  • Post-investment support accounts for a large share of firm staffing

“can we disaggregate the general partner job and say what are the things that we really need the general partners to do?”

Scott Kupor · 35:31

“we want a general partner to look for great deals, build relationships, make investment decisions, and sit on boards and be valuable to those companies.”

Scott Kupor · 35:46
#operating model#portfolio support#venture firms#specialization
Explainer38:34

The Internet-Money Case for Facebook's Libra

Kupor presents Libra as an attempt to create stable, Internet-native money rather than replace every national currency. The proposed system could lower transaction costs enough to support micropayments that card networks make uneconomic, although its governance and feasibility remained experimental.

  • Traditional digital payments still depend on existing financial rails
  • Transaction fees make very small payments impractical
  • Stable digital money could help users in high-inflation countries
  • The proposed consortium was intended to decentralize governance
  • The project still faced major execution and trust questions

“They want to create Internet money”

Scott Kupor · 38:34

“You can even do like micro payments, which is very hard to do because of trains action costs.”

Scott Kupor · 39:54
#libra#cryptocurrency#micropayments#facebook
Explainer42:22

What Actually Happens During a Venture Fund's Ten-Year Life

A venture fund is nominally structured for ten years but may continue for twelve to fifteen. Most initial investments occur in the first three or four years, followed by later capital calls and follow-on investments in the existing portfolio.

  • Each fund is a separate legal entity
  • Ten-year funds often persist beyond their stated term
  • Primary investments cluster in the first three or four years
  • Roughly seventy percent of committed capital may be called early
  • Remaining capital supports later financing rounds
  • Successful managers raise a new fund every few years

“we raise funds and those funds typically have a tenure life.”

Scott Kupor · 42:35

“you do most of your investing typically in the first three or four years”

Scott Kupor · 43:43
#fund lifecycle#capital calls#limited partners#follow-on investing
Explainer47:41

How Brand Makes Venture Performance Persistent

Top venture performance can persist because a winning reputation attracts stronger founders, employees, and customers. Since early financing rounds are often exclusive, the brand advantage helps the same firms win scarce opportunities and prevents competitors from sharing those returns.

  • Academic research finds persistence among top-quartile venture firms
  • Prestigious investors provide signaling value beyond cash
  • Founders use investor brands to recruit employees and reassure customers
  • Exclusive early rounds create winner-take-most access
  • Past success can improve future deal flow

“Their money is more than just money”

Barry Ritholtz · 48:35

“if you've got the brand that gives you an unfair advantage in competing for the new deals.”

Scott Kupor · 49:12
#performance persistence#signaling#brand#deal flow

Story· 1

Story02:25

Taking Loudcloud Public During the Dot-Com Collapse

Kupor recounts taking Loudcloud public in 2001, when the IPO market had nearly disappeared. The company chose an IPO not because conditions were attractive, but because it was the best viable source of capital available.

  • Loudcloud entered the market at the height of the technology downturn
  • The company needed capital despite hostile conditions
  • Only a tiny number of US IPOs occurred in 2001
  • Financing choices depend on the alternatives available at the time

“We took it public in two thousand one, actually for the very honest reason, which was that was the best source of capital at the…”

Scott Kupor · 03:18
#loudcloud#ipo#dot-com bubble#capital

Takeaway· 3

Takeaway03:57

Why Employees Come Before Systems in an Acquisition

While integrating Opsware into HP, Kupor found that the acquirer's systems playbooks were strong but the human questions needed greater urgency. Employees first needed clarity about whether they had jobs, what those jobs were, and where they should report.

  • Integration is both operational and human
  • Job clarity is an immediate employee concern
  • Strong systems processes do not replace direct communication
  • Product, engineering, and sales employees largely had opportunities at HP

“The most important thing, though, is what are you going to tell the employees about who has jobs, what those jobs are going to be,…”

Scott Kupor · 04:36
#acquisitions#integration#employees#communication
Takeaway51:57

Software Is Reaching the Industries It Previously Missed

Kupor sees no near-term end to the software transformation thesis. The next opportunities increasingly lie in sectors that technology had touched less deeply, including education, healthcare, government services, energy, and oil and gas.

  • Software remains a long-term investment thesis
  • Historically resistant industries are beginning to change
  • Healthcare and education remain early in their transformation
  • Technology-first startups may attack problems differently from large incumbents

“software is still eating the world at least where we sit.”

Scott Kupor · 52:23

“we're still at the very very beating phass of it.”

Scott Kupor · 52:51
#software#digital transformation#healthcare#education
Takeaway54:54

Why Conventional Debt Can Be Dangerous for Startups

Debt must be repaid just when a young company may need to reinvest in product development and growth. Convertible debt can postpone valuation negotiations, but repeated notes can hide substantial dilution until they convert during an equity round.

  • Conventional debt is not permanent capital
  • Repayment can compete with research and growth spending
  • Convertible debt can be faster and defer valuation
  • Multiple notes make cumulative dilution difficult to see
  • Kupor prefers straightforward equity in many startup situations

“The problem with debt is at some point you have to pay it back”

Scott Kupor · 55:13

“they realize, oh, my gosh, I've sold a lot more of the company than realized.”

Scott Kupor · 56:37
#startup finance#debt#equity#dilution