Every VC has the one that got away—a company now worth billions that pitched him years ago when it was worth nothing.

For Ben Lerer, that company is Harry’s.

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Investor Ben Lerer shares which startup he passed up on at the early stage #startups #vc #founder #tech

Jackson sat down with Lerer-Hippeau’s managing partner, Ben Lerer, for a candid conversation about his enthusiasm for the future of AI in media startups, the deals he’s missed out on over the years, and the cautionary tale of Foxtrot, the venture-backed corner grocery store. Here’s what Jackson learned:

1. 🥱 AI isn’t supposed to be boring. Don’t treat it like it is.

a. When people think, “How can AI help my company?” they often imagine using generative AI to create content more cheaply or game SEO differently.

b. Instead, Ben encouraged me to use AI to, “deliver totally new content experiences to customers.”

c. His advice: Take your consumer-first brain, get pumped on the technological wave that is AI, and dream up experiences for your audience that weren’t possible before this new reality.

2. 💢 Lean into disruption.

a. If you lead a small company (like we do) it’s a lot easier to turn a motorcycle than it is to turn a battleship.

b. The big companies cannot adapt to the new technological landscape as quickly as your startup can—lean into it and make flexibility a central pillar of your work.

c. “Figuring out how to turn AI into your friend and not your enemy is going to be a requirement.”

3. 🕯️ Successful VCs back great founders, not just great ideas.

a. Ben shared about the companies that got away, the ones he wished he’d invested in, and the one that sticks out to him most is when his firm passed on investing in Harry’s, the shaving company.

b. He was then and is still today good friends with the founder, Jeff Raider. He thought he was a great founder at the time and shared that Jeff is, “exactly the kind of person we should be in business with.” And yet, Lerer-Hippeau passed on a very early opportunity to invest in Harry’s, a company now valued at $1.7 billion.

c. Ben recalls that his decision to pass was rooted in concerns about the “category” that the company was in, instead of trusting in a founder he knew was a winner. Ben says he learned a valuable lesson back then about choosing to back great founders, even when all the others details aren’t perfectly ironed out.

ICYMI:

Everything you missed last week in tech and startups.

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Everything you missed last week in tech and startups! #tech #startups #vc

WHO JUST GOT PAID?:

- EliseAI, an AI property management platform, raised $75 million in Series D funding led by Sapphire Ventures.

- AMD agreed to acquire ZT Systems, a server solutions provider for computing companies, for $4.9B.

- Bolt, a fintech company, is reportedly raising more than $450 million in Series F funding at a $14B+ valuation, according to The Information and Eric Newcomer.

- DEFCON AI, a military operations software company, raised $44 million in seed funding, led by Bessemer Venture Partners.

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