Experience makes entrepreneurial tasks easier and faster, but founders must maintain urgency and avoid complacency, as ease often precedes difficulty.
Kalanick reflects on how his experience has made tasks like writing vision notes much faster, but warns that when things feel easy, it's often a sign that challenges are imminent, requiring founders to stay pushed. ✦ AI generated
Travis Kalanick · a16z Podcast · 2026-08-14 · original ↗
starts at this moment · 30:20
“How are you different as a founder building at Adams than you were building Uber in terms of what have you changed? What have you kept the same when you reflect back? What do you think you were successful because of what you did versus in spite of what you did?”
the other thing that's interesting and I think sometimes, you know, the the the new the the the young entrepreneurs that are just coming up right now, they don't totally get it is that when you get into your third and fourth, I don't know, this may be even my fifth at this point company, you get freaking really good at doing stuff. And so things that used to take me a day or three days, a lot of stress, anxiety, like I am going to do this take me like 45 minutes. And that's a beautiful thing... But being pissed off makes you good as an entrepreneur. So, like I got to make sure I'm still fired up... when you when it gets easy it's time to push hard. If I always used to say like uh if something if it's getting easy it's about to get really [__] hard and you don't want it to be that way. You want to make it hard versus hard make it hard on you... there's actual times when it's easy, but it's because you're not continuing to push. So it's one thing when you're just not winning, but you're pretending like you are. And there's another thing when you're winning but you're taking it easy and you're about to start losing.
verbatim transcript · starts at 30:20
30:20young entrepreneurs that are just coming up right now, they don't totally get it is that when you get into your third and fourth, I don't know, this may be even my fifth at this point company, you get freaking really good at doing stuff. [snorts] And so things that used to take me a day or three days, a lot of stress, anxiety, like I am going to do this take me like
30:4745 minutes. And that's a beautiful thing. There are things you don't get like like I'm like so used to adversity at this point that it's kind of normal. So I don't get as pissed off. But being pissed off makes you good as an entrepreneur. So, like I got to make sure I'm still fired up. Like, come on. >> That's that pissed off energy. >> You [ __ ] with me. I'm going to kick
31:10your ass. >> You know that it's easier when you're 25, I think. I don't know. I'm just not It's like a dude. Whatever. It's fine. You be you, dude. It's good. You get too used to adversity and that's kind of a problem. But, uh, yeah. So, I'd say those are some of the fun changes. Yeah. >> What's an example of something that used to take a long time, but is now just so
31:29much easier? Like a >> Look, I wrote a vision note. Um, when we rolled out Adams, it was a few months ago. It was like like, you know, look, I'm biased obviously, but like it was very, I think, a very well-ritten vision note. Uh, 10 years ago, 15 years ago, that would have taken me, I don't know, hundreds of hours. >> Yeah. >> And it just flowed.
31:58>> Yeah. Like, okay, I can't say I wasn't thinking about it a lot, but when I was doing the writing, it actually just flowed and just happened. I'm like, holy [ __ ] it just happened. Holy cow. Like, the one I just did for the for for this funding, >> like, okay, I procrastinated, but you know, that's a thing. But like once I did the right, I'm like, "Oh, dude, we
32:18got it." It took like 45 minutes. I'm like, "This is amazing." >> And it that's related to presentation, communication, >> strategy, this kind of thing. uh unsure at which is pretty awesome. >> Ben, how have you seen Travis evolve since you first got to know him and comment more broadly? We have a lot of repeat entrepreneurs in the room in terms of when like Travis you have a
32:41massive success that also has some mistakes along the way. You know, what lessons do you learn from the next time versus, you know, what do you make sure to keep and continue because that's what that's what got you there. Well, I I thought that was actually a really good way to characterize it, which was, you know, he thought he was in survival mode when he had 20,000
33:03people working for him. And that that that idea um is dangerous. Uh when you have such a big organization, it it's dangerous on two levels. one, it's dangerous because you're not, as he said, bringing enough people along with you, but it's also dangerous in that you've got all these people working for you. Um, and their interpretation of that idea could be a lot. You know, you kind of have to [laughter]