Newsletter #37: Becoming an AI-First company? Ravi Gupta said "AI or Die," Fiverr CEO Micah Kaufman effectively said "we got this."

Starting in April with Tobias Lütke, high-profile CEOs are issuing direct, often public, mandates for their organizations to become “AI-first.”

This movement signals a strategic pivot far deeper than mere technological adoption.

It represents a fundamental re-evaluation of business models, operational efficiencies, and talent management as enterprise AI capabilities are being understood and absorbed into the fabric of how companies operate.

A growing cohort of influential companies are leading the charge towards an AI-first operational model.

Their CEOs are not merely encouraging AI exploration but are embedding AI proficiency and utilization as core tenets of their business strategy and employee expectations.

As Ravi Gupta put it in such a succinct manner, “AI or Die.”

Or as Brendon Geils, founder and CEO of Athena Intelligence said, after meeting the client in real life, the first job for one of their client-facing leaders is to “build a carbon copy of themselves in the product for the customer” which is about as AI-first as you could be...

While memos from Shopify, Fiverr, Duolingo, Box, Meta, Google, HubSpot and others can be found, we’re clearly too early to have a shared definition of what an AI-first company actually means.

But that doesn’t mean there aren’t leaders in the arena, doing everything they can to navigate this extraordinary time while doing so transparently so we can all benefit.

One of those leaders is founder and CEO of Fiverr, Micha Kaufman.

Kaufman stands out not just for the directness of his memo, but for the comprehensive philosophy he has described behind it. His approach is particularly valuable because it balances pragmatic implementation with forward-thinking strategy—all while maintaining Fiverr's position at the intersection of human creativity and technological advancement.

It’s also especially useful because of the parallels to the work being considered by CMOs and CROs within enterprises moving towards an AI-first approach.

In a two-hour interview on Cognitive Revolution, Kaufman provides one of the more detailed conversations I’ve heard about what becoming AI-first actually entails for a modern organization by a leader clearly in execution mode.

Two Hour Interview of Fiverr CEO Micha Kaufman on Cognitive Revolution

In an attempt to distill Micha’s message to its essence, below is the framework I took away from the interview.

While I think anyone looking to move in the direction of becoming an AI-first company can benefit from listening to the interview, Newsletter #37 will effectively try to give you the TLDR.

Needless to say, this is the first of several Newsletters, Podcasts and Micro Essays on this topic of becoming an AI-First company.

In the meantime, if you're looking for more, AI with Alec has a bunch of content in one centralized place (finally) so head over there.

1: The End of Easy Tasks

“And what I wrote in the email is what I said is that we need to understand that things that were considered easy tasks will no longer exist, and what was considered hard tasks will be the new easy, and what was considered to be impossible tasks are going to be the new hard.” (7:37)

“Any task that the human being should not do because it's repetitive and the computer can do better, we should stop doing.”

“I think orchestrating the most unique things that are going to be mind-blowing will always require this. You don't need to protect it. It's going to happen by itself.”

"It's going to be just new types of jobs that require human beings rather than just machines. Machines should do what machines are good at, period. That's it.” (1:27:49)

2: The 5X Rule + Optimizing For Velocity

“But I think that the overarching idea is really to take this AI-first approach of like, if—if you're still working like it's 2024, you're doing something wrong, because it's no longer the case. And it's evolving at a head-spinning speed.” (12:14)

“I think that the vast majority are going to do this full transformation, and it's going to be incredible because it will allow us to push, you know, either five times faster or five times the amount of things that we're pushing, you know?” “I'm seeing how the pace is picking up, and I'm—I'm always optimizing for velocity. This is, you know, it excites me more than anything else.” (1:42:13)

3: Enterprise AI Future Belongs To Hackers

“Yeah, look, I think, you know, scouting is one, but you can always claim that you can create an agent to scout for stuff and whatever. What I do think is that, at least in our space, I think that the future belongs to hackers.”

“That, to me, is like—I think that those who are going to be the most resource-proof people, and you know—you know one when you see one. It's very easy because: one, they're naturally born as scouters, which means that they always know what's the latest and greatest; two, it's not just that, but they took the latest and greatest to its boundaries and then broke it, and they know how to mesh things, they know how to connect different things and make them work together. They always find the use cases that the actual developers of the tech didn't think of.”

“I think that the future belongs to these guys, and, like, I have many of them, many, many of these people on the team. And it's like—I mean, these guys are not scared. They're—they're not even concerned. This email wasn't for them.”

“I think in any area, I mean, this, you know, having this hardcore hacker mentality is going to be in very high demand, and these are going to be the people that you pay for and you pay generously.” (33:39)

4: Taste And Domain Expertise Is A VERY BIG Deal

“AI is incredible, no doubt. It's giving all of us superpowers, but all of us. So it's basically ground zero. We don't have an advantage.” “Nathan, you don't have an advantage over me or over someone else just because you use AI, because everybody uses AI. And so it gives—oh, you can design yourself? Well, so can I.”

“But what would make your design or mine stand out? What is the competitive advantage? And I think that people go to people, in many ways, for that.”

“So you go to someone who's actually, you know, who has better taste than you, who has better command over the fanciest and best tools. You do it because they've gained a tremendous amount of experience in things that you're not experiencing.”

“And what AI has done is just elevated the starting point where no one, none of us has a—has an advantage.” (39:09)

5: Self-Educate So You Don’t Work Like It’s 2024

“It's less about that, in my view, and it's more about how proficient you are with the new tech.” “We might be hiring for a legal position in our legal team, and if you're not versed in how not to work like it's 2024, then you're out.” “You can be god, but you're not—I mean, you're not going to get in because it's like, you're taking someone who you need to train now. And I don't want to train anyone.”

“And this is also because you don't need to. It's all available online. Just take a course. Do whatever hack and figure it out. There is no manual, and I don't need to feed you. No one—the world doesn't owe you. Learn it. There is no barrier to learn on your own. And so if you're unfamiliar with the latest technology and its capabilities and the latest products and solutions and whatever, then you're not going to pass.”

“This has changed, you know, materially in the past maybe two years.”

“There's going to be new professions. They're going to be very complex.” (1:44:25)

6: Train Your Own Model

“And what we've offered with Go is just a different approach of saying, you know what, we think—we love the technology. We think it's incredible. But we want to give—also experiment with giving this technology to our creators and saying, instead of, you know, giving away your creation to train this in infinite model, train your own model that is going to be Nathan's model for creation, and it's going to have your—its corpus is going to be your world of creation. It's going to be your body of work, and it's going to be very, very true to your unique signature and style.”

“And what's interesting about this is, for customers, it gives them a very predictable outcome. And for creators, it's your model. You do—you do with it as you please. You get the reward because, basically, I mean, sure, the model is doing regeneration, but it's regeneration just based on you.” “I mean, even Michelangelo had, like, nine or 10 people working in his workshop. It doesn't make his creations less Michelangelo-like, right? So essentially, this is how we experimented with it. And instead of like being, you know, being a threat, it—it becomes your tool to do more, to extend your capacity, and to, you know, turn one person into a production house, but also give instant gratification for the customers.” (54:20)

7: Don’t Answer The Same Questions Over And Over Again, Have An AI Personal Assistant Do That For You

“And the other portion is really to design this super powerful personal assistant which is not just assisting you by interacting with customers and answering the same questions over and over again, and, you know, giving—giving offers and getting—doing the intake of information and all of this, but it's also a business partner. It allows you to do all kinds of things that you had to manually do, like research on the platform to figure out, you know, how to reposition yourself or fine-tune your services, your offerings.” (56:11)

“Yeah, so the personal assistant was pretty obvious. And it's not like, I—I don't think it's just like customer service or customer care. It's your salesperson, and it allows our creators to actually spend less time doing the things that they like the least, is like, you know, responding to initial messages and collecting information about the customer. It's not that they don't love their customers, but this is like—this is just the intake. This is the filtering, is like and—in and—and answering—I mean, it's the same questions all over again, the fit to their skills, their availability, how to price things.”

“So it's much more than just being, like, you know, attending to customers in a very simplistic way. And it's super powerful. Like, the assistant knows when the freelancer is actually online. So sometimes the assistant would decide on their own to ping the freelancer, saying, you know, "Nathan, there's a really interesting customer, and I think you should join us." And they will ping you to join the conversation. So it's—and sometimes it's just allowing you to sleep and get—get recharge.”

“It's—it's really important, and it frees up more of your time to actually create, which is your—what you're passionate about.” “And look, this is a conversion machine. This is incredible. I mean, it—it converts so much better than the sellers themselves. And by the way, it's them, because it's—I mean, the personal assistant is trained on you, just on you. Your offerings, your profile, your entire—sometimes it's tens of thousands of conversations with customers, your orders, everything. It knows everything about you.” (1:04:11)

8: AI-Facilitated Commerce Without So Much Friction Is Coming

“That's an easy one. The answer is yes. It's just—I mean, it's a simple yes. I think and I've—I kind of alluded to it previously when I said that the experiences of how we consume stuff, how we find things, how we convert, how we get comfortable, how we create trust, how we make a decision are going to change.”

“And I mean, we're doing deep and extensive use of AI in—in the matchmaking. It's like, I'm not going to go into details here for obvious reasons, but it's—we're—we're doing deep stuff with it, and we're seeing the change. And I think that this is just going to become better and better over time. So definitely—definitely—I mean, improving liquidity, absolutely yes, without a doubt.” “You'll see Amazon doing experiments that are bolder, bigger. You're going to see other platforms doing the same. I think it's just a matter of time. We're—we're in the very early innings of it.” (1:33:48)

To Ravi Gupta's point,“winning in this new world requires a ‘full re-founding’ of your company” in order to “become an AI-first company.”

Are you in? You've got this?