The Man in the Room When Email Got Out of Control - and Fixed It
It is 1996 and free email is a wild idea. Hotmail just launched. Scott Weiss is employee number thirteen. He is not there for the prestige - there is no prestige yet - but for the strange specific instinct that this thing, this free web-based inbox, is going to rewrite how human beings communicate. Eighteen months later, 100 million people have accounts. Microsoft buys the company for around $400 million. Weiss is thirty-something and has just watched history get made from inside the room.
Then spam happened. The great plague of early email. By 2001, inboxes were drowning. Weiss, who by this point had survived the dot-com implosion at Idealab and taken exactly the lessons a crash teaches you, sat down with Scott Banister and decided to build the antidote. IronPort Systems. Hardware and software appliances that stood between senders and inboxes and made the gatekeeping decisions that were killing corporate IT departments. Not glamorous. Not consumer. Deeply, architecturally important.
"You have to know what it feels like for the boat to be sinking."
- Scott Weiss on the lessons of the dot-com crash
He started with two employees. He ended with 450 and a $200 million annual run rate. Cisco paid $830 million for IronPort in 2007. That is the version of the story that appears in press releases. The version Weiss would tell you involves a lot of travel, a canary-yellow Porsche Boxster parked outside a building where all-nighters happened, and the creeping recognition that he was good at his job and mediocre at being a father. He wrote about it later - a candid Medium essay called "Success at Work, Failure at Home" - with the kind of honesty that makes venture capitalists uncomfortable and founders feel briefly less alone.
After Cisco, after the obligatory stint as VP of the Security Technology Group, after watching a large company move the way large companies move - "bureaucratic, slow, can't make decisions" - Weiss took eighteen months off. Not to angel invest. Not to explore a thesis. He went dark. Recharged. Then Ben Horowitz called.
In April 2011, Scott Weiss became the fourth General Partner at Andreessen Horowitz. Marc and Ben had built a firm in their image: operator-first, founder-friendly, aggressively involved at the board level. Weiss fit. He was not a financial engineer who had learned to cosplay as a builder. He had built. He had sold. He had managed the aftermath of a sale. When he sat across from a founder, he was not performing empathy - he had the scar tissue.
Known for
Weiss introduced 360-degree feedback reviews for General Partners at a16z - evaluating each other the way companies evaluate their employees. In a culture where venture capitalists answer to nobody but their LPs, this was eccentric. In some firms it would have been career-ending. At a16z, it became part of the culture.
He led a16z's $60 million Series B in Lyft in 2013, when ridesharing was still being called a regulatory time bomb. He joined boards at Optimizely, Dwolla, Pindrop Security, Jumio. He wrote essays - about boards, about leadership, about authenticity - that circulated in Slack channels and Y Combinator batches in ways he probably did not intend. His essay "Never, Ever Promote From Within" became a canonical artifact of the era, not because it said what the title said, but because it spent 1,200 words complicating itself.
Then, in January 2016, he wrote one more essay. Short one. Called "An Update." He was stepping back from investing in a16z's new fund. Not leaving. Not launching a competitor. Just - stepping back. His kids were approaching college age. He had been gone for their childhoods building companies and sitting on boards and flying to meetings. He was not going to be gone for this part too.
