Ravi Gupta

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157 appearances 1 recordings 1 series first heard Feb 2025 last heard Feb 2025

Ravi Gupta’s voice in public audio — every appearance, attributed to the second.

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I just think that if you're a big company, you better be awfully paranoid about a startup because their ability to build distribution is way faster than it's ever been. And I think that if you're a startup, you better be really clear about who you're going up against. There is a massive difference in speed amongst the big companies at how quickly they are leveraging their distribution advantage.
You and I have talked about in the past this idea of enthusiastically rehiring somebody is the standard. If you could do it again, would you hire this person to do this job? I think you have to enthusiastically underwrite your business. And what do I mean by that specifically? You need to go and say, what is the purpose of your company for these customers?
What is the best, fastest, and cheapest way for us to go and deliver that? And is it what we're doing now or not? And you can hold nothing sacred. So what do I mean specifically? Let's take pricing. Today, a lot of companies have seat-based pricing models. I don't believe that that will be the future of the way that people buy software.
I think that there is something, we've heard this from different people, but maybe they're going to pay for the job to be done. Maybe they're just going to say, I want this piece of work done, and I want to pay just for that piece of work done. I don't want to pay for each person that uses your software. I want to pay only when something gets done.
Well, that is a massive and dramatic shift if you're a big company. to move away from the pricing model that got you there. But understanding that that might be the future of your pricing, that is a big realization that has a bunch of knock-on effects as to like, well, what do you go do then? And maybe it means you'll have 60% less revenue now if you move to that.
But in the future, you have the potential for 5X more revenue because you have a bigger customer base that you can go after, or you can do more jobs for somebody. But I think one thing with that, you can hold nothing dear. That's one thing, which is pricing model has to be evaluated.
all under this idea of enthusiastically re-underwrite the way that you're delivering the purpose of your company to its customers. That's why. Two, I think that you do have to go role by role and figure out what is this AI superpower version of each of these roles. Is it that it's replaced? Is it that it's augmented?
And I think that that is a big deal of like the specific role by role conversation. And I know people are like, well, we have 5,000 people. I don't want to do that. I'm like, can you tell me what's more important than that? What is more important than figuring out whether you have the right people doing the right jobs for your company? So that's that.
I think the third thing, Patrick, is this idea of what percentage of our time do we spend thinking about our customers? I really think that's valuable. You know this thing that Shopify does? Shopify will just kill meetings, end recurring meetings randomly.
I think doing the calendar audit of what percentage of our time as a company, as a leadership team, first as the CEO, then as a leadership team, then as the company, is spent on things that move the needle for our customer. What percentage of time do our engineers spend coding? All these things I would do. And it's easy for me to say, because I don't have the responsibility of doing this.
You asked, what would you suggest to somebody? It would be that. And then I think the last one, which is maybe the most optimistic is like, what have we dreamed about providing for our customers that was impossible before? And let's all use this idea of what is barely possible now and too expensive. Oh my God, that's going to be possible in six or 12 months. Let's go build that.
One of the things that you and I have been talking about separately is how much should we care about margins right now? Well, it actually means you should care a lot about margins in certain topics and not a lot about other topics. If something's like an AI first product, you probably shouldn't care that much about the margins of it because it's going to get so much cheaper to deliver that.
Whereas if something's not an AI first product, you should care a lot about the margins because that is the durable future. Those are a few things that I think I would do and I would suggest to people to do. And I also think anything that prevents me from being agile. I know I keep on coming back to this.
Anything that prevents me from making a change, I would try to like write down and figure out how I eliminate. And maybe that means you don't provide guidance anymore. Maybe it means that you tell people like there's going to be a negative and then there's long-term going to be a positive.
Maybe it means that you tell your team that we're in the midst of a big change and like some things are not going to be as predictable. You have to be able to make the changes you need in the company and it's hard to predict those changes right now. And so I think you need to like give yourself the ability to be very, very, very nimble.
It is so easy to say when you're not in the seat. I want to recognize that. My response to that is you can't outsource your conviction, which means don't do it because somebody tells you. I do think before you come to that conclusion, you owe it to yourself to spend weeks or a month really trying to convince yourself that you're wrong.
Because I think this is the point that I feel most strongly about. Go figure it out for yourself as to what's actually happening with a lens of trying to break your prior thought on it. It's convenient to think that you can just gradually get into this.
It is really convenient to think, I'll just figure it out later and I'll do it in a gradual way because that's just way easier for us to deal with as people. And I think anytime you have a convenient belief on something important, you should really examine it. And I think in this case, examine that convenient belief.
And if you really, after a month of being super open-minded and really trying to break it, you come up with that, great, do it. But do it affirmatively. Don't do it because it's the convenient path that allows you to not have to change very much. You and I are both NBA fans.
It is really hard for an NBA team to be like really good for a long time and never bottom out before they get to be good again. It's really hard to just keep it going and reloading and reloading and reloading. It usually has a really painful period afterwards. I'm a Bulls fan. Look at the Bulls. Like, geez, it's very convenient to think maybe I'll just be able to do it both ways.
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