Top 60 Aaron Levie Quotes (2025 Update)

1. “Better to be too early and have to try again, than be too late and have to catch up.”

— Aaron Levie

2. “The most customer-centric organizations can answer any question by deciding what’s best for the customer, without ever having to ask.”

— Aaron Levie

3. “You’ll learn more in a day talking to customers than a week of brainstorming, a month of watching competitors, or a year of market research.”

— Aaron Levie

4. “Execute like there’s no tomorrow, strategize like there will be.”

— Aaron Levie

5. “Start with the assumption that the best way to do something is not the way it’s being done right now.”

— Aaron Levie

6. “The best technology is aimed far enough in the future that it stands out, but close enough to the present that it blends in.”

— Aaron Levie

7. “The product that wins is the one that bridges customers to the future, not the one that requires a giant leap.”

— Aaron Levie

8. “Every single industry is going through a major business model and technology oriented disruption.”

— Aaron Levie

9. “There’s a lot of pride that business owners have. It’s actually really critical that pride and ownership extends to everyone in the organization. I think of everyone is in the same boat in driving the company forward.”

— Aaron Levie

10. “If people don’t think the odds are against you, you’re doing it wrong.”

— Aaron Levie

11. “I don’t use many apps. I use naps.”

— Aaron Levie

12. “Too little process and you can’t get good work done. Too much process and you can’t get any work done. Most companies never find the middle.”

— Aaron Levie

13. “I’m obsessed with speed. I’m always asking myself, ‘Why can’t we do things faster? Why can’t it happen more efficiently? Why is this requiring three meetings instead of one?’”

— Aaron Levie

14. “That’s already been tried before only means the first attempt got it wrong.”

— Aaron Levie

15. “Opportunity lives at the intersection of what people need tomorrow and can be just barely built today.”

— Aaron Levie

16. “I think I’m the kind of person who would be very difficult to employ – I’m pretty annoying, but driven.”

— Aaron Levie

17. “Modularize, don’t customize. Build a platform as opposed to building all of the custom technology and custom vertical experiences.”

— Aaron Levie

18. “Your product should sell itself, but that does not mean you don’t need salespeople.”

— Aaron Levie

19. “If there could’ve ever been a magical time to build an enterprise software company, now is absolutely that time.”

— Aaron Levie

20. “The chance of failure is almost always better than the guarantee of never knowing.”

— Aaron Levie

21. “Start with something simple and small, then expand over time. If people call it a ‘toy’ you’re definitely onto something.”

— Aaron Levie

22. “Startups live at the intersection of existential crisis and everything going perfectly great.”

— Aaron Levie

23. “I’m certainly not into money and prestige. For me there is simply nothing more exciting than people involved in the creation of great products. That is what drives me.”

— Aaron Levie

24. “Startups often win because it’s easier to see what comes next when you don’t have to worry about maintaining what came last.”

— Aaron Levie

25. “The only barrier to entry you can create is to consistently build a great product.”

— Aaron Levie

26. “I think people are always able to achieve more than they think they can. While that’s cliche, I don’t know if managers think about that enough. You have to set your sights extremely high.”

— Aaron Levie

27. “Entrepreneurship: 10% coach, 20% player, 30% cheerleader, 40% waterboy.”

— Aaron Levie

28. “When you’re doing something you’re passionate about, stress becomes a featurenot a bug.”

— Aaron Levie

29. “You can keep ‘consumer’ DNA at the center of your product. That will always mean that adoption is easier.”

— Aaron Levie

30. “Why we do what we do: that moment when you get to see the future on your computer screen before the rest of the world.”

— Aaron Levie

31. “The 10% between 90% done to 100% done takes most of the time, causes most of the stress, but is all of the value.”

— Aaron Levie

32. “Sometimes things are the way they are and can’t be changed, other times it’s because no one ever tried. Your job is to find the latter.”

— Aaron Levie

33. “My dad is a chemical engineer, and my mom was a teacher. They were pretty serious about education, but I always thought about things a little bit differently.”

— Aaron Levie

34. “My downtime tends to resemble my uptime. Weekends are workdays, but toned down. Over the whole weekend, I may have five meetings, as opposed to six on a weekday. I used to play piano for 30 minutes at night, but I had to pull that out of my schedule. I don’t have time for nonwork stuff.”

— Aaron Levie

35. “If you’re waiting for encouragement from others, you’re doing it wrong. By the time people think an idea is good, it’s probably too late.”

— Aaron Levie

36. “Jeff Bezos is opening a retail store and owns a newspaper. Turns out everything we thought about the Internet is wrong.”

— Aaron Levie

37. “Look for new enabling technologies that create a wide gap between how things have been done and how they can be done.”

— Aaron Levie

38. “A lot of being productive personally is determined by how you organize your entire business. You can’t separate those two things.”

— Aaron Levie

39. “If every customer is using your product “correctly”, you’ll never learn anything interesting about what to do next.”

— Aaron Levie

40. “I have a lot of faults. I often interrupt in meetings. I talk too loud. I talk too fast.”

— Aaron Levie

41. “It’s unfortunate biologically we have to sleep.”

— Aaron Levie

42. “We’re going from a world of customized software to standardized platforms.”

— Aaron Levie

43. “Better to be right about the trend and wrong about the implementation, than the other way around.”

— Aaron Levie

44. “The benefit to building a startup is that customers don’t have the same kind of friction when they adopt new technology.”

— Aaron Levie

45. “The only way to avoid disruption is to constantly do what you would if you were just starting out.”

— Aaron Levie

46. “If you don’t go to every level of your company, you distance yourself from the marketplace and from your people.”

— Aaron Levie

47. “Innovation in tech favors the naive and the stubborn. If you are too rational you won’t tackle problems that others once failed at.”

— Aaron Levie

48. “Focus too much on the near-term and you won’t get tomorrow’s customers, focus too much on the long-term and you won’t get today’s.”

— Aaron Levie

49. “We didn’t really start the company to go build an enterprise software company.”

— Aaron Levie

50. “Companies have never won. You’re always either fighting for survival, or fighting for relevance.”

— Aaron Levie