CHAPTERS
Benchmark’s ‘MyStore’ idea collides with the ‘Oasis’ plan (Webvan’s origin story)
David Byrne arrives at Benchmark eager to make an impact and keeps circling an idea: an online ‘everything store’ starting with groceries. Bruce Dunlevie reveals Benchmark already has a business plan—‘Oasis’—that becomes Webvan, framing it as a bold idea the partners were hesitant to pursue.
Why Webvan is the exact kind of venture ‘swagger bet’
The hosts argue Webvan fits the venture model: asymmetric upside with capped downside and portfolio logic. They frame it as the type of risk that can define a top-tier early-stage firm, especially when executed early and cheaply.
What Webvan aimed to be: the ‘everything store’ delivered by van
Webvan’s ambition is described through founder Louis Borders’ lens: take another huge swing after Borders Books and build what Amazon would later become. Groceries are the wedge, but the endgame is broad everyday commerce delivered to your doorstep.
The last-mile advantage—instant gratification as Webvan’s starting line
Unlike early Amazon’s slower delivery expectations, Webvan launches with last-mile delivery as a core feature. The discussion highlights how ambitious this was and how it raised execution difficulty immediately.
Internal tension: ‘Just do food’ vs ‘compete with everything’
Even after investing, Benchmark partners push to narrow the plan to groceries rather than pursue the broader ‘everything’ vision. Byrne, however, is portrayed as captivated by Borders’ scale of ambition and more willing to back the full vision.
Byrne’s role: proving Benchmark can still make the scary bets
The conversation frames Byrne as the partner willing to do what others at the firm won’t, aligning with why he left a successful executive search career. Webvan becomes a vehicle for reinjecting risk-taking DNA into Benchmark.
Deal mechanics: a small early check with huge theoretical upside
Webvan’s initial financing is presented as a clean, classic early-stage venture bet: $7M split between Benchmark and Sequoia, with board seats and meaningful ownership. Importantly, Benchmark and Sequoia do not continue pouring money in pre-IPO.
The public-market peak and the ‘not actually that big’ crater
Webvan reaches an ~$8B market cap at its peak—turning a tiny early investment into massive paper gains in a few years. The hosts emphasize that, relative to modern blowups, Webvan’s dollar magnitude is less extreme than its reputation suggests.
Lockups, timing, and the dot-com crash: why the payoff didn’t materialize
Despite the enormous paper gains, the hosts note investors likely couldn’t fully exit before the crash due to lockups and timing. Webvan’s collapse becomes the enduring story, even if the initial venture decision was sound.
Venture philosophy takeaway: buy risk, diversify, and back missionaries
The discussion broadens into venture doctrine: investors should seek founders with massive, missionary ambition and accept that timing risk is part of the game. Portfolio construction (30 companies) is the mechanism that allows embracing maximal risk per bet.
Swagger goes public: Benchmark invites an insider to write eBoys
Benchmark’s renewed boldness expresses itself culturally: they allow author Randall Stross unprecedented access to the partnership and portfolio for the book eBoys. The move is framed as intentionally provocative—making ‘graybeards’ uncomfortable and signaling confidence.
Webvan secrecy and the author’s access: a final symbol of the moment
The hosts note Webvan’s operational secrecy—press weren’t allowed into facilities for fear of leaking trade secrets—making Stross’s access especially notable. This cements the theme: Benchmark’s appetite for bold moves extended beyond investing to narrative-making.
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