Monetizing AI: OpenAI's $4B Strategy

26 May 2026 · 10 min · 4 chapters

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In short

OpenAI’s $4B strategy to monetize AI by creating an internal unit focused on corporate AI deployments, aiming to beat competitors (including Anthropic) and reduce rollout friction for enterprises.

Guest backgrounds

The episode is hosted by the show’s speakers (one mentions “Jayden” and a “Jamie”) and promotes their “AI Hustle School community” (200+ members, $19/month) where members share how they use AI to grow businesses.

Key claims

OpenAI is moving down the stack from model provider to deployment partner, using sales/prospecting, compliance, and support. It resembles Palantir-style “developers inside your org,” and parallels prior OpenAI PE/joint-venture approaches. Microsoft previously dominated enterprise distribution via Azure; Anthropic’s enterprise buzz is pressuring OpenAI. Once embedded, enterprise AI is “sticky” due to compliance/bureaucracy.

Notable examples

PE firms owning ~2,000 businesses for rollout; comparisons to Salesforce/HubSpot adding AI receptionist features; “Claude/Anthropic Claude CoPilot” style agents that can control computers and write code; OpenAI targeting large enterprises rather than SMB AI agencies.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

OpenAI's $4 Billion Strategy Overview

1:00 to 1:21

Explore OpenAI's new corporate AI deployment strategy and its implications.

AI School Community Insights

1:21 to 1:58

Learn about the benefits of joining the AI School community for insights on AI tools.

“school community yeah every single week we record a bonus piece of content that we post over on our school community.”

OpenAI's Business Model and Market Position

1:58 to 7:45

Understand OpenAI's approach to integrating AI into businesses and its competition.

“It's interesting because OpenAI, of course, they make the product, they make the underlying LLM model that can do a lot of things, but corporations and businesses don't always know how to roll it out.”

Selling AI Services to Small Businesses

7:45 to 9:02

Get tips on effectively selling AI solutions to small businesses amidst widespread misconceptions.

“And the thing about that is these are incredibly sticky.”
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Transcript

Automatic transcript. May contain errors.

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0:31Shop the Sherwin-Williams Memorial Day Sale and get 30 % off paints and stains May 15th through the 28th. Whether you're refreshing your interior or exterior, we've got the colors to bring your vision to life. And with delivery, getting everything to your door is easier than ever. Shop online to have it delivered or visit your neighborhood Sherwin-Williams store. Click the banner to learn more. Retail sales only. Some exclusions apply. See store for details. Delivery available on qualifying orders. open ai has recently committed four billion dollars to a new unit aimed at corporate ai deployments so they're really trying to beat out claude or just beat other companies out in getting their tools used by major corporations and this is their play at it we're going to get all into it today and talk all about it but before we do jayden why don't you tell them about our school community yeah every single week we record a bonus piece of content that we post over on our school community.

1:27We don't post it anywhere else. And we basically are breaking down how we're personally using AI tools to grow and scale our businesses. It's$19 a month. We have over 200 members, people all building things actively, people that are vibe coding or they're inside of an organization or they're upskilling their career with AI tools. It's where you get all the hacks. It's where we share all the insider info that we can't share publicly anywhere else. So we would love for you to go check it out. There is a link in the description to become a member to it. And we will hopefully see you there. Okay. So this story, I think is pretty fascinating with opening.

2:00I, the reason I wanted to cover it is because with this$4 billion that opening AI is putting in, this is essentially the business play that we've been telling a lot of people on the podcast and Jamie's doing some things in this area, but we've been talking to a lot of people on the podcast about just how much opportunity is in basically getting companies to integrate AI fully into what they're doing and getting all of the benefits out of AI. It's interesting because OpenAI, of course, they make the product, they make the underlying LLM model that can do a lot of things, but corporations and businesses don't always know how to roll it out.

2:34They don't know how to take advantage of everything. And so OpenAI, to try to basically remove that friction, is making a business that is deploying their own tool inside companies. Now, this isn't like a super novel idea. They're not the first people to kind of invent this or think about this. And actually for the last couple weeks and months, they've been doing some deals with a lot of PE firms. So the PE firms, they own 2000 businesses, and then they kind of partner with OpenAI and OpenAI rolls this out into all their 2000 businesses. But now they're doing this in a little bit more of a solo perspective where they have to do all the prospecting.

3:10They have the sales team. They're going to go call you. They're going to, you know, cold call companies and be like, Hey, we think that you could use OpenAI's services and tools, yada, yada. And they try to roll them in and they'll charge for the rollout. It's kind of like what Palantir has been doing for a long time where they'll send Palantir developers into your organization to help tie you into Palantir's technology. So OpenAI is doing the same thing here. I think this is a good move as far as getting distribution goes. It's a lot of work. There's other companies that do this type of stuff and now they're just kind of moving further down the stack from just making the technology to also helping with deployment.

3:43Yeah, so I think this is a really smart play and And it actually, to me as a hustler, makes me consider that the time clock is running out here a little bit for us who are a bit ahead of the game to come in as like AI consultants or to sell AI services to other businesses. Pretty soon, some of these big companies are going to come in and take over. For example, one of the things I'm currently trying to do is sell AI receptionists to local contractors, companies and things like that. Well, a lot of these companies are already using CRMs that are now like big CRMs, like think about Salesforce or HubSpot, things like that.

4:27They're now, HubSpot is getting their own AI receptionist that people can already integrate into their whole software suite. So as these big corporations integrate a lot of these AI tools, some of these opportunities for those of us who are hustling, trying to sell AI services are going to it's going to run out. So I think this is an important article to pay attention to. Four billion dollars is a lot of money. And it's a joint venture with OpenAI. So there's not really it's not its own company. It's all its own internal unit within OpenAI. They're trying to get companies to adopt their software.

5:05Which is interesting because when they've done some of these PE joint ventures that are basically the same company, they like invest a billion dollars in. And so it's interesting because it's like those would technically be directly competing with them. So they have these like joint ventures, they have these spun out groups, and now they have their own internal. They're all doing the exact same thing. And technically, they're all kind of competing for the same clients. So that's kind of interesting to me. It's also pretty wild when you consider Microsoft's position, who is actively fighting for all of these same customers.

5:36And when OpenAI kind of first got on board with Microsoft and they got on Microsoft Azure, they kind of just let Microsoft run away with that segment. They're like, look, we're going to make this tool. Everyone in the world is using it. We have, you know, almost a trillion or sorry, almost a billion weekly active users on this thing by now. Right. And so they're like, you know, who really cares if we go hard after the enterprise? We'll let Microsoft kind of run that. But as they're seeing, Anthropic really hit the enterprise hard. They got massive adoption and it started actually eating into OpenAI because a lot of people that were just paying for the$20 a month of OpenAI are seeing that Anthropic is doing better.

6:11A lot of people are talking about it. It's got a lot of buzz and hype. And so people are actually shifting over to that instead. And I think OpenAI is kind of concerned and they realize that's a huge part of the market that they didn't, I don't think they like put enough time and energy into. So that's where all of these new spinoffs and joint ventures and now this whole new $4 billion unit is going to start trying to tackle. Now, in my opinion, product, you know, an incredible product kind of sells itself. I wouldn't be talking about, you know, Anthropic all day long if it was just because some open AI salesperson cold emailed me and told me like, hey, you got to try our tool and integrate it.

6:47Or if Anthropic had done that, I'd be like, whatever. The reason why Anthropic is amazing to me, and I think to so many people is with a lot of their pushes with things like Claude Cowork that can literally take control of your computer. They can write code. They can build things. They can just do everything. It's amazing. It's perfect. It's flawless. I think if OpenAI gets to that level and they put the investments in to do a lot of those features, they're just going to get the adoption, whether they have a$4 billion unit that rolls things out. But the one thing I will say, maybe even that is more for like vibe coders and people kind of on the cutting edge, maybe in startups where they have a little bit more autonomy.

7:24Inside of an enterprise, you don't have quite as much autonomy and you need a lot of regulations and approvals and things go very slowly. And so because of that, having an organization like what OpenAI is standing up where they have the salespeople, they have the compliance people, they have this huge team that can help support these rollouts is probably a a pretty big benefit. And the thing about that is these are incredibly sticky. Once you, you know, once OpenAI is the backbone to how, you know, Chase Bank does XYZ, Chase Bank is not changing that anytime soon because talk about, you know, the absolute slowest corporations in the world, they're slow to adopt, but they're also really slow to move off of something because there's just so much compliance and legal and paperwork and bureaucracy.

8:05So if OpenAI can spend$4 billion and really get itself entrenched in a lot of these organizations, it's pretty hard to pull out. So the last thing I wanted to bring up as kind of you talked about being a side hustler and how to make money off of all of this and kind of where we're seeing the whole industry in the future. You're 100 % right that OpenAI is going in this direction. They're going hard. They're spending$4 billion. I don't think this is going to be something that really directly competes with what a lot of people probably listen to the podcast are doing unless you're a salesperson at a massive organization targeting these companies.

8:34I think this is really OpenAI targeting big organizations, big enterprises. And there's a lot of companies that have, you know, 10, 15, 60 employees that something that, you know, something that a listener is just trying to spin up their own kind of AI agency could really do some massive benefit and could make some crazy money very quickly doing. So I don't think it's really probably competing too directly with this$4 billion opening. I think their target audience and their customers are going to be quite big, but definitely is something interesting to look at. Yeah. Part of what I'm realizing as I get further into this whole thing is that a lot of these small companies, like if you're trying to sell them an AI software as a service, there's a lot of lack of education there as far as they don't understand why they need the tool yet and how it can benefit them.

9:27So if you are one of these hustlers like us and you're trying to sell AI services to businesses, you need to get good at education and helping people understand why some of these tools could benefit them. And especially because there's a lot of negative press about AI right now. People don't want AI. AI. And so if you can reframe what the actual product is and how it can help their business, I think you're going to do a lot better when it comes to sales and things like that. Yeah, that's a great point. I think so often we think like, oh, let me just go tell someone, hey, let me implement AI in your business and show you how you can improve it.

10:06And they'll be like, I don't even know what that means. You have to sell them. I think a lot of times on the use cases when you're talking to SMBs, you're like, look, do you want a receptionist that can answer every call for you, even while you're, you know, a plumber on the job doing something, it will, it'll take the phone call so that they're not going to your next competitor and it will schedule an appointment or follow up. So like, I think explaining the use cases, explaining the value, then someone would be like, yeah, sure. That sounds great. Like that's a problem I legitimately have. So I think more of that and less of the kind of ambiguous, like, hey, like we can help you improve and do things faster and cheaper.

10:41Like no one even knows what that means. And so I think if you talk to specific companies about their specific problems and how you specifically solve them, that's probably where you'll see the most success in that. Yeah, absolutely. And stay away from the term AI. People, I found, don't like that. So anyways, hey, thanks for listening. If you got any value out of this episode, we would really appreciate a rating or review wherever you are listening. Those help us out a lot and help us reach more people. And don't forget to check out our AI Hustle School community if you want to actually learn how to take some of these tools and make money with them and grow your business.

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From the publisher

In this episode, we discuss OpenAI’s new corporate deployments unit and why the company is putting billions behind enterprise AI adoption. We also look at how this move could help OpenAI sell more AI tools to businesses and deepen its role in the future of work.

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