Startups regularly underestimate how difficult hiring gets, especially after an expensive Series B/C. 1. Mission matters more. The people who join you at Seed/A might want to build a sales intelligence tool because they like seeing 0 to 1. They know that once this gets big, they’ll take home a good chunk of change. After a B/C, they think “is this really what I want to be working on?” 2. Financial incentives are lower. You easily see a path for a $30M valued startup to 10x. Usually this means going from $0 to $10M in revenue. Seeing a path for a $1B valued startup to 10x is far harder. It can mean going from $10M to $200M+ in revenue. And given the incrementally lower equity employees get, they’re counting on that 10x. 3. You attract a very different persona. They’re usually more risk averse and riding on the coattails of the success and name your company has already built. Culture can easily dilute if you’re not careful. The builders get replaced by the certain kind of BigTech person who wants “startup experience” without taking on the risk. They might still be smart, so it’s tricky to catch in any sort of technical interviews. 4. Culture degrades with size. It’s almost by law. In the beginning, you’re under 50 people. You’re all working on a startup you stood up from nothing. This builds a strong sense of camaraderie. As you go to 200 people, your early builders become managers. You start seeing more and more unfamiliar faces in the offices. At some point, you don’t even know everyone in the company. Everyone is eager to do “new” things and leave their mark, but what needs to be done is quite straightforward. The sales team feels like a different kind of person that takes up half the office. You’re eagerly watching the revenue, and your emotions ride on the back of it now, not the joy of creating. Management is in disarray. Now, projects keep getting killed. People keep getting roped into a new “customer issue” and can’t do their main project. New employees feel like this isn’t the culture they signed up for. Old employees feel like they work as hard as they used to from day 1, but the new employees treat this like a “job”. You get your first set of departures. Morale is low. Lunch banter shifts to “what if we just went to instead?” Keeping the company from tearing apart at the seams seems like an insurmountable task. Growing past these rounds can be very challenging and many founders are left blindsided. The awesome company they once had can quickly become a shadow of its former self. And it’s a stage which often separates the elite founders from the great ones. The answer here is usually having a mission worth going the distance for or a culture worth fighting for.

startups, here's enterprise decoded ... 1. 'circle back' = dead 2. 'get it done asap' = 60-90 days 3. 'send me what I can share internally' = 3 bullets 4. 'this is exciting' = let me play a role where I can show how I helped shape this for us internally 5. 'send me your paper' = i will send you mine back OR be prepared for 4-6 iterations on your paper 6. 'how much time is needed' = 30min OR less 7. 'I will bring my boss, who's joining on your side' = I expect you to match seniority -- ie. your founder 8. 'No questions from my side" = I have no idea what just happened 9. 'This price seems fair' = this falls below what I had budgeted 10. 'Give me time' = stop following up mf-er, I'm on it

Startups, start your engines! We're proud to be the Founding Partner of IMSA Labs, a platform for innovation and collaboration across motorsports, automotive, and technology. As part of this partnership, we’re launching Oracle Cloud Innovation Studio—the first initiative within IMSA Labs designed to help startups by combining our cloud and AI technologies with @IMSA’s live race operations. Learn more:

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