The myth-busts, hot takes, explainers, and tools worth keeping.
⚡Myth Buster· 3
⚡Myth Buster55:00
Benchmark Almost Faded Away Before 1997
Corrects the myth that Benchmark was an instant success, revealing missed deals like Amazon and Yahoo, a founding-partner departure, and a genuinely bleak outlook heading into 1997.
Benchmark missed both Amazon and Yahoo in 1995-96.
Founding partner Val Vaden left the firm at the end of 1996 due to a style mismatch.
By early 1997 the odds looked bad for the fledgling firm.
#Val Vaden#early struggles#fund one
⚡Myth Buster2:09:00
Recruiting Bill Gurley: 'Balls and Brains,' Not Just Balls
Explores the internal debate about whether Bill Gurley was too analytical to fit Benchmark's culture, and how his data-driven style ultimately redefined the firm.
Some partners worried Gurley's intellectual, analytical style didn't fit a 'balls' business.
Gurley's approach shifted Benchmark from formation-stage bets to data-driven Series A investing.
Gurley went on to define Benchmark's marketplace investing era (Uber, OpenTable, Zillow, GrubHub).
“we all know that this is more a balls than brain's business”
#Bill Gurley#recruiting#investment style
⚡Myth Buster2:22:00
The Wandering Years: Google, Skype, and Facebook Slip Away
Covers Benchmark's costly detour into international expansion, corporate joint ventures, and a billion-dollar fund, which coincided with missing Google, Skype, and Facebook.
Benchmark expanded into Europe and Israel funds and raised a $1B main fund in the early 2000s.
They missed investing in Google despite early access, and lost Skype to eBay's own deal.
A Friendster board conflict blocked Benchmark from even evaluating Facebook's Series A.
“there are three examples all of which are sins of omission which are the biggest sins in Venture Capital none of the sins of commission…”
#Google#Facebook#Skype#strategic missteps
✶Explainer· 1
✶Explainer09:30
How John Doerr and Kleiner Perkins Ruled 1990s Venture Capital
Sets the stage by explaining John Doerr's total dominance of Silicon Valley VC before Benchmark existed, and the Kleiner Perkins 'karetsu' model of forced business-development partnerships among portfolio companies.
John Doerr was the single dominant force in 1990s VC, backing Netscape, Amazon, and Google.
Kleiner Perkins ran a 'karetsu' model that pressured portfolio companies into biz-dev deals with each other.
Any ambitious young VC needed a real answer for how to compete with Doerr.
“if you were an ambitious young venture capitalist in the 1990s in Silicon Valley and that was a big if you could do very well…”
#venture capital history#John Doerr#Kleiner Perkins
❝Story· 8
❝Story17:30
TVI: The Only VC Investor in Microsoft
Tells the story of Technology Venture Investors (TVI), the little-known firm that was the sole venture investor in Microsoft, owning 5% for $1M and holding until IPO.
TVI invested $1M for 5% of Microsoft and reportedly never invested again before IPO.
This single deal gave TVI outsized standing in the venture community.
Dave Marquardt's philosophy at TVI ('the CEO is responsible and accountable for everything') foreshadowed Benchmark's ethos.
“they were the only Venture Capital investor in Microsoft yep one million dollars to own five percent of the company”
#Microsoft#TVI#Dave Marquardt#venture capital history
❝Story22:30
Bob Kegel's Crusade for Equal Partnership at TVI
Chronicles Bob Kegel's working-class background and his growing conviction that unequal firm economics were morally wrong, setting up TVI's breakup.
A 1995 New York Times article revealed deep resentment among junior partners at old-guard VC firms.
Bob Kegel grew up in Flint, Michigan and rose through General Motors University and Stanford GSB.
TVI's senior partners ultimately 'declared victory' and dissolved rather than restructure economics.
#Bob Kegel#firm economics#venture capital history
❝Story40:30
Founding Benchmark: An Audacious Name and Premium Pricing
Describes how five founders named the firm Benchmark and priced fund one at 30% carry versus the industry-standard 20%, signaling premium positioning from day one.
Benchmark's five founders: Bob Kegel, Bruce Dunlevy, Andy Rachleff, Kevin Harvey, and Val Vaden.
They charged 30% carry, above the market-standard 20%.
The firm's own prospectus declared 'there is always room at the top.'
“it was you haven't heard of us but we're already important”
#Benchmark founding#fund economics#branding
❝Story47:00
Stanford Blackballs Fund One
Describes the fierce LP backlash to Benchmark's premium carry, including Stanford's endowment organizing other university endowments against the fund.
Some LPs like Horsley Bridge loved the model and backed fund one heavily.
Stanford's endowment tried to organize other endowments to reject Benchmark entirely.
Stanford's team later completely turned over and became a major Benchmark LP decades later.
Covers hiring star executive recruiter David Byrne to reinject swagger into the firm, and the resulting high-risk, high-reward Webvan investment shared with Sequoia.
David Byrne left a lucrative executive search business to join Benchmark as its fifth partner.
Webvan was pitched to Byrne by Bruce Dunlevy as a bet the other partners lacked the nerve to make.
Despite Webvan's eventual collapse, the initial $3.5M bet by each of Benchmark and Sequoia was a smart, capped-downside, uncapped-upside venture wager.
“Dunleavy reached into a stack of papers and pulled out a business plan called Oasis he tossed it to burn explaining that he and the…”
#David Byrne#Webvan#risk-taking
❝Story1:23:30
The eBay Deal That Changed Everything
Details how Benchmark's whole partnership worked together to win, structure, and support the eBay investment, turning $6.7M into roughly $4B.
Bruce, Bob, David, Kevin and Andy each contributed relationship, marketing, recruiting, and consumer expertise to win the deal.
Pierre Omidyar and Jeff Skoll had a competing $50M acquisition offer from Knight Ridder.
Benchmark's $6.7M investment turned into roughly $4B in under two years.
“on an 85 million dollar fund a 6.7 million dollar investment turned into four billion dollars in a little over 18 months less than two…”
#eBay#defining investment#Pierre Omidyar
❝Story2:53:00
The Fab Four: Refounding Benchmark's Golden Era
Introduces Peter Fenton, Mitch Lasky, and Matt Kohler joining Bill Gurley to refocus Benchmark on early-stage investing, producing an extraordinary run of wins.
Benchmark pulled back from international and corporate distractions and refocused on core early-stage investing.
Peter Fenton, Mitch Lasky, and Matt Kohler each brought distinct expertise (enterprise, gaming, consumer social).
Fund VII (2011) reportedly returned roughly 25x before fees, driven by Uber, Snap, Discord, and more.
#Peter Fenton#Mitch Lasky#Matt Kohler#Bill Gurley
❝Story2:58:30
Uber: From Best Partners to Boardroom Lawsuit
Traces the Benchmark-Uber relationship from Bill Gurley's early conviction and the famous Series A chase down Sand Hill Road, to the eventual lawsuit that helped end the Fab Four era.
Travis Kalanick chose Benchmark for the Series A specifically because of Bill Gurley.
Escalating private valuations and governance scandals eventually pushed Benchmark to sue Kalanick alongside other shareholders.
The Uber conflict is framed as a key trigger for the end of the Fab Four partnership era.
“they're the best I went with them because they're the best I didn't want to work with anybody else”
The Current Benchmark Lineup and How to Become a GP
Summarizes the present-day Benchmark partnership (Peter Fenton, Eric Vishria, Sarah Tavel, Chetan Puttagunta, Miles Grimshaw) and the informal pattern of how new partners get recruited.
Every recent hire (Eric Vishria, Sarah Tavel, Chetan Puttagunta, Miles Grimshaw) was already a proven investor before joining.
Several new partners had prior board or deal overlap with existing Benchmark GPs before joining.
The firm continues to avoid junior hires, sticking to the equal-partnership recruiting spec.
“if you want to be a GP at Benchmark just uh be on boards with them that seems to be the takeaway”