Ben Horowitz On What Makes a Great Founder
In a Nutshell
Ben Horowitz identifies great founder CEOs as blunt truth-tellers who ask aggressive questions, think independently, inspire curiosity, and decisively tackle problems without hesitation or over-deference, exemplified by Zuckerberg, Elon Musk, and Ali Ghodsi. Common scaling pitfalls include lacking confidence (leading to decision debt and paralysis), botching executive hires like sales VPs (prioritize blind references, discipline over enthusiasm, playbook writers for complex products), and cultural mismatches between engineers and salespeople. Success demands constructive confrontation, clear behavioral rules for culture, and building confidence through reps to manage seniors effectively without micromanaging or pretending omniscience.
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Really good companies, the very best companies, tend to have founders and CEOs who ask pretty aggressive questions. Zuckerberg, Larry Page—those guys who have gotten all the way to the mountaintop—are pretty blunt. If you're running away from the truth to preserve feelings, that's a very dangerous thing in a tech company. The corollary is that bad news travels fast. As CEO, you need to find out if something's wrong.
Today's guest is Ben Horowitz of A16Z. Reasons he's fun: behind-the-scenes look on why Andre passed on HubSpot back in the day (funny story). He's seen so much, backed amazing CEOs and some that went down in dust. What do great ones have in common? Patterns? Same with failures. Read his book The Hard Thing About Hard Things (published 2014) when running HubSpot—really good. Wanted updated view on what's changed.
Ben is completely unfiltered and gets after it. Lots of nuggets.
You probably don't remember when we first met. HubSpot pitched you on the Series D. Three came in: newly hired COO JD Sherman, myself, co-founder Dharmesh (Dash). Walked in, nice welcome—your sales guy Mark Cranny was former colleague. Just written book Inbound Marketing, two of your marketers had it. Felt like hometown advantage.
Sat down: JD barely got a sentence out—“wait, you're the COO, tell me about your background.” Spent 15 minutes on JD, then 15 on me—“you're such a knucklehead, why did you hire a COO?” then Dharmesh. You guys passed, as did everyone. Two weeks later read your book, saw you're not a fan of hiring a COO. Put a ginormous chip on JD Sherman's shoulder—incredibly beneficial. Chips on the shoulder are really valuable.
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