New episode of Long Strange Trip with @bhorowitz of @a16z is now live. The first time I pitched Ben for @HubSpot, he passed on us. It stung. So naturally, it’s the first thing I brought up with him in this convo. He’s seen more founders up close over the last 20 years than most, so I wanted to ask him what separates good founders from great ones, what CEOs get wrong the most, and how they can fix it. He even names the best CEO he currently works with… Even at our Series D, when Ben passed, deep down I felt like I had no idea what I was doing. Turns out, that’s pretty common. The dangerous response is to start over-deferring to others to compensate, which is exactly when things go sideways. Here’s what else I got from this conversation: • On ‘Founder Mode’ going too far: The original insight from @bchesky is right: don't over-hire senior people and then over-defer to them. That creates fiefdoms and a political vacuum. But Ben thinks people have twisted it into "don't hire experienced people at all," which is dangerous. Founder mode means staying accountable to outcomes and having the confidence to manage people with more experience than you. • Decision debt: Ben calls decision debt "the worst debt" a company can carry because it paralyzes the entire organization. Founders who hesitate at 52/48 decisions, waiting for certainty that never comes, create a vacuum that breeds politics and dysfunction. The pile of decisions you're avoiding? A bad hire you are still trying to make work? A board member dynamic that's off and has been for awhile? A pricing model you know isn't scaling? I had this at HubSpot. Every 4-5 months I'd look up and realize everything had slowed down, and the only fix was to make a bunch of decisions I'd been dodging. The moment I made them, things started flowing again. • “Constructive confrontation”: Running away from the truth to spare feelings is dangerous. One of my bugs as CEO of HubSpot was that I’m pretty conflict averse. I think a lot of first-time founder CEOs are. But bad news has to travel fast inside fast growing companies, it’s a good thing if it reaches the CEO efficiently. And that only happens if people are willing to say the hard thing, and you’re willing to hear it. I probably should have leaned into that earlier. • Why founder-engineers suck at hiring salespeople: This is where most technical founders get wrecked. Engineers and salespeople are wired opposite: Ask an engineer a question, they try to find the correct answer. Ask a good salesperson the same question, their first instinct is: Why are you asking me that? If you're an engineer interviewing a sales candidate, their answers are going to feel evasive and it's going to annoy you: that's exactly why you'll reject the best ones and hire the worst ones. • His fix? Blind references. Call people who owe you a favor, not people who owe the candidate one. And ask who they can bring with them. Great sales leaders have a crew of followers. • What the best CEOs actually have in common: The greats can be introverts or extroverts, ivy-leaguers or dropouts. None of that stuff matters. The through-line he sees across Zuckerberg, Musk, Jensen Huang, Ali Ghodsi: they think for themselves (you can feel when someone's working from original thought vs. reading the room), they stay deeply curious, and they are blunt. This was a fun one. Enjoy.