Rob Hayes

Who they are

Rob Hayes is a Partner at First Round Capital — he was Uber's first institutional investor and backed Square before it was Square.

Person

Rob joined First Round Capital in July 2006, when the firm was barely a year old and seed investing was still a fringe idea. Before VC he spent the 1990s inside the hardware-meets-software wave at GO Corporation, Geoworks, and Palm Computing — each of them bets on pen-based or mobile computing that were too early, which probably gave him a fine-tuned sense of timing. He ran a corporate venture fund unit at Omidyar Network before making the move to First Round. His MBA from Columbia Business School (Class of 1995) sits on top of a BA from UC Berkeley. The through-line is a product-management sensibility — he came up evaluating what users actually do with technology, not just what it promises — which shows up in bets like Uber (first investor), Square, Mint, TaskRabbit, GOAT, eero, and Bowery Farming. He writes at Fast Company and has appeared on TWiST (This Week in Startups, Episode #249) talking venture and startups. Possibly — he has also started ProductShots.ai, a platform for improving product photography in online retail, and runs a Substack called Lunch Culture.

How they likely show up

Joined First Round in July 2006 and has stayed — long-tenure at a single firm signals deep institutional conviction, not a résumé-builder.
Came up through product management at Palm, GO, and Geoworks → likely evaluates startups through a product-user lens first, business model second.
Was Uber's first institutional investor and backed Square early → comfortable making high-conviction calls before market consensus forms.
Active public writing at Fast Company plus podcast appearances on TWiST → comfortable being visible and articulating a point of view, not just picking quietly.
Possibly — runs a Substack (Lunch Culture) and started a side project (ProductShots.ai) alongside a full-time investing role → high agency, probably doesn't sit still between deals.

Conversation tips

→ Reference a specific Fast Company piece he wrote — he'll know instantly whether you read it or just Googled his name.
→ Ask about the Palm/GO era specifically — those companies shaped how he thinks about timing, and it's a formative chapter most people skip.
→ He was Uber's first institutional check; asking what he saw that others didn't will get a real answer, not a rehearsed one.
→ Don't pitch abstractly — given his PM background, he'll want to know what the user problem is and why now, not just the market size.
→ If ProductShots.ai comes up, approach it as a genuine product conversation, not a curiosity — it signals he still builds, not just backs.

Toolbox

Openers

Open on the Uber first-check story — he was the first institutional investor before anyone thought ride-sharing would work; asking what the signal was in 2009 will get a substantive answer.
Mention his Palm Computing and GO Corporation years — both were early mobile/pen-computing bets that didn't pan out commercially, and that failure school almost certainly shapes how he thinks about timing risk today.
Possibly — bring up ProductShots.ai: a sitting VC who's also building a product for e-commerce photography is a specific, interesting bet worth asking about directly.

Discovery questions

You came up through product management at Palm and GO before moving to VC — how much does that PM lens actually change the diligence questions you ask?
You were Uber's first institutional investor. What does a company look like at that stage that makes you write the check when no one else will?
You've been at First Round since 2006 — two decades is a long time in seed investing. How has the job of picking companies actually changed, versus how people say it's changed?

Avoid

Don't lead with generic 'what's hot in AI' small talk — his public writing and portfolio show he engages with specific founder and product problems, not market-trend headlines.

Make it yours