Lesson 20a: Developing Offensibility

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Well, here we are, it's about 5-6 a.m. on a Saturday, and we're running into about three hours of conference calls, and then full day of work, some spreadsheet analysis, some market disruption risk for probably one of the most well-known investors you've ever heard of. Yeah, there's a lot going on these days, especially in the age of AI and disruption in the enterprise SaaS world. We're seeing a shift happen from classic vertical niche SaaS, these 30,000 SaaS companies or more, to agentic AI agent companies who are AI native, AI first.

Some are further ahead than others. They've rebuilt their platforms in the past to be AI first, or at least AI agent native capable, rather than sort of these old lumbering tech stacks with a lot of tech dead and the inability to move quickly. And so we're starting to see the great separation occur of the haves and the have-nots, and the did-its and did-nots, and the ones who are sort of behind the eight ball, thinking differently, and the ones who are out in front, sort of setting the pace.

And it got me thinking about this word because pretty much the first bullet point on every deal memo and every investment committee these days is AI disruption risk, AI displacement threats. Basically, is AI going to take this business to zero now, in the next five to seven years, by the early 2030s? Where is the world heading? What's happening? And so everyone is highly, highly focused on defensibility. And if you don't know what defensibility is, we should talk about that for a quick second.

We've touched on it in a couple other video spots. Defensibility said in different terms is a moat. So the classic example of a castle, right? You can't storm the castle as easily and take it over and take all the food and, you know, become the master of the castle if you dig a big old trench around the whole castle and then fill it with water.

That is by definition a moat. And then outside of the water, you put like barriers of fire and pungi sticks. And so it becomes very dangerous or difficult to get to.

So that in the business world, like Sun Tzu's Art of War, is a way to slow down potential attackers. You actually see this in cybersecurity. It's not that no system is infallible.

No system is completely immune to attack. But what you do is you create these barriers and these firewalls to give you time. So like a lock and a key, like it's going to take you an hour to get through the first one, 10 hours to get through the second one, 100 hours to get through the third one, and on and on and on, which gives you time to defend against those attackers because you can set up detection mechanisms and see what's happening and then start to build and defend and other things.

So like a sports analogy, there is defensive defense. There's also offense. And if you grew up in Iowa and you're an Iowa Hawkeyes fan like me, then you understand this on a deep level.

It's very hard to be a Hawkeye fan. I'll tell you why. It's hard to be a Hawkeye fan because we will have great teams and great people with great core values, and they'll do a lot of really cool stuff.

But come the fourth quarter in basketball, football, pretty much whatever, except for wrestling, where we've dominated for decades, hand-to-hand combat, there you go, right? We'll lose oftentimes in the fourth quarter. And the question is why? Well, it taught me something from a young age, which is you're playing not to lose. And the minute you go from playing to win to playing not to lose, you've already lost the game because you're fearful, you're pulling in, you're getting afraid of movement, like, right? You're trying to move the ball away from the offense and you stop attacking.

And when you stop attacking that offense, you lose the game. Sometimes you hear coaches and people say like defense wins games. Defense helps you win games, but you can't defend your way to victory.

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If all you are is defense, you put no points on the board and you don't win by definition. Something's going to slip through at some point. The best athletes in the world basically just come down to, I don't ever make a mistake.

That is the best in the world. And you continue to make a point. And the one who makes the point is the one who makes the mistake first.

But you still have to be a killer on offense. And a killer on offense can beat a good defense. Look at Michael Jordan, look at LeBron James, look at Kobe Bryant, right? Like the list goes on and on.

That's just basketball. So this idea of every analysis, every investment committee deal menu, all the discussions focusing on defensibility, on modes, you may be missing something. What about offensibility? What about that? And you're saying to yourself, well, Sean, that's just sales and marketing.

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Okay. Yeah. But what are you doing that's different in sales and marketing? And I would push you even further.

Product as growth. Product drives growth. Product is offense and defense simultaneously.

That's what the best product people in the world understand. That's what Steve Jobs understood with Apple. That's how the iPhone was made.

Offense, I'm a giant systems integration process with defensibility built in because we've had to invent new methodologies, capabilities, and we protected that in some ways, but we also built a brand and cornered resources and established partnerships and put something together in a unique way that had never been done before. And we attacked the market with that. And people thought we were crazy because we put a touch screen on a phone.

Not that we combined an iPod, a music player, an internet navigator, maps, and a touch screen. It was, am I going to not want to use a keyboard? And what you find is that literally depressing a physical key takes more time and effort and energy on one thumb for one split second than it does to just tap quickly. You multiply that one movement, time that one human all throughout a day, times year, times decades, times 8 billion people.

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That's a lot of finger movement. You remove that finger movement and now I've made you attack the key so you can do things and get things done faster and you're on offense instead of defense. And then I put everything in the phone coming to you as a person.

Do you see the parallels I'm making to AI? If not, I'm shaking you right now and getting you to wake up. Offensibility. And so now with these AI agents, you hear these leaders talk about capability overhang, which is this fancy term and it's an interesting PR maneuver.

But I've been around the block. I know what you're saying. The PR maneuver is you're not using my product.

I built stuff that people didn't want or know how to use. And now I'm screwed because I built all this compute and capacity and I've got a ton of investment and I've got a valuation that I need to achieve. And so I just went and built a bunch of stuff.

And we're starting to see this now in the market with these leaders. They built a bunch of stuff and they lost sight of the customer, of the user, and they lost sight of keeping them up to speed with the product. At every point in time, your marketing, your product, and your users have to be in lockstep.

If one of those is too far out in front, you're fraudulent, you've built too fast, you've confused your users, etc. You can get them over a hump, but it does take time. However, there's something different.

There's another way to do this, which is the holy shit, gotta have it. Here's the test with gotta have it. I put something in front of you.

I don't talk. There's no demo or maybe the demo is silent. I just show you something and you go, holy shit, I gotta have that.

Fashion works this way. Guess what else works this way? Car design. Holy shit, look at that.

I gotta have that. Let's go test drive this puppy. I'm on the website.

I'm doing all the research. A song with a catchy melody, not just lyrics. The melody draws you in.

Look at Drake, one of arguably the best recording artists of all time who can continue to do it over and over and over and over and over. Do you think Drake was thinking about defense? No, he wasn't thinking about defensibility. He was thinking about offensibility.

He brought in other artists onto his songs, kept him fresh. He kept spitting verses and lyrics, kept him fresh. He went to battle against Kendrick.

Kendrick may have won a bunch of Grammys, but guess who lit up the coffers in the bank account? Drake was like running circles around that dude. It's not even close. He's laughing all the way to the bank.

He's got his own jet and he flies around it. Like, come on. It's turning into a catchphrase.

I'm just here to tell you, quote unquote, what really drives my gears. I'm just here to tell you that when everyone in the investment community, the product community, the tech community is all losing their minds about defensibility, defensibility, defensibility, guess what? You all think the same. You're all lemmings.

You're all stamp and repeat. How do you expect to win when everyone's doing the same, thinking the same, being the same, acting the same, doing the same analysis? How do you expect to win? Not once have we seen someone ask the question, offensibility. Oh, Sean, that's commercial.

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Is it? With this capability overhang? Is it a product question? Is it a mindset question? Yes, it is. It is. How is your product simultaneously attacking, defending, and protecting your user base and giving them superpowers? If I presented to you a safe jet pack that put on your back and then allowed you to fly and be as free as a bird, people would take that.

People would want that. When Jack GBT first launched, it grew like crazy. Why? Because like, that was offense.

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You got to do the same kind of thing. This new crazy stuff with like CloudBot, I don't care if you change the name, whatever, where you're basically giving an AI agent computer use and just talking to it like text message and saying, hey, can you just go do this thing for me? And like, it goes through all of your computers and acts as you. And then they'll just start recording how a user behaves and map all your stuff out.

So, you know, that's where this is all headed. And then the social networks where the agents are talking to each other. No shit.

How do you think we came up with WISP? W-H-I-I-S-P dot com. AI agents talking to other AI agents, communicating and having discussions and transacting in real time, making payments with one another, to interact with one another and get access to data, to workflows, to people, to products, to tools. And I'm paying and I'm doing a selection and a decision criteria in real time as new products, tools, capabilities come on market every step point in time, in real time, as rapidly as you can possibly do it with computation, energy and connectivity, assessing who is the best in the market, choosing that one for that exact task, pulling them in, paying them a microtransaction, passing that data in and out and on and on and on and on and on.

We're so far out in front, it's not even funny. We got there a year ago. Where is everybody? Where are you all? This is my question to you.

Where are you? Your way, I'll tell you where you are. You're miles back there. You're miles back there talking about defensibility from the old world, from the old business.

The old world got fucking demolished. It's done. The past is done.

It's gone. We're in a new future. You got to wake up.

We are in a new future. We are in the future. AI is here.

Autonomous robotics is here. Self-driving is here. Digital assets and currency is here.

Spatial computing is here. It's all around us. It's invisible so you can't see it.

It's happening over the airwaves. And you're worried about defensibility instead of getting in the game and attacking and attacking. And guess what? Big tech is running away with it.

The glasses, spatial computing, AI in here, they've got billions of dollars sunk into this stuff. And you're sitting around a conference room table talking about defensibility, talking about fear, talking about our products good enough. Like it's no big deal.

Like we can just rest on our laurels and you know we're out here doing this thing and it's going to be fine and it's not a big deal. Like I'm here to tell you, it's a giant deal. We've been in emerging tech our entire lives since we were 13 years old.

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I turned 45 this year. 45 minus 13. That's 32 years I've been in this thing.

I've seen this like do this like right like oh and then like the internet and then mobile right and then all this and then AI came. It's gone. AI is accelerating all of this stuff on a level that you can't even see.

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GitHub commits now that cloud code is out there went straight up and down. We've never experienced curves like this as a human species. You need to start thinking offensibility.

Otherwise you're going to be living in the past like my beloved Hawkeyes playing not to lose and losing your shirt in the fourth quarter. And make no mistake we're entering the fourth quarter. In some ways it's the fourth quarter of your legacy business.

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And there's going to be a great separator in the next year. 2026 is the great separator. Where you're there's a lot of people right here and there's going to be ones that go like this and then oh right and there's going to be ones that go oh and they go right and then there's going to be other ones that are just like going.

So is this shift from enterprise SaaS to AI? I think AI agents continues and the human race is lazy and they're on social all day and they just want to like type a text to their friends and family, listen to music, like go out to brunch and you know hang out with their family. And they want to shoot a text off to their robot that operates in cyberspace and then the one that operates around their house like you better be a part of it. You better be a part of it.

You better start creating something valuable in that new future, building it today, building for the future. Because that future is here, it's not evenly distributed at all. And you got to start playing with offensibility in mind.

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So is there time? Is there time? There's time. But not if you're sitting around a room like worried about defensibility. You're building this stuff.

I already know product teams that have already built like AI agent platforms. They're AI first. They're AI native.

They're already out in the world. Like startups are growing like crazy. Enterprise SaaS firms have already rebuilt their entire platform.

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They're ready to go. And that's making them go faster and faster. And they're still operating in a market, in the same market.

So the question is really like creative thinking and what your customers want. And what your customers want isn't more technology. After this whole conversation about where we are with technology, your customers don't want more technology.

They want invisible software. The very first post I wrote on Tumblr maybe 15 years ago now, it was called invisible software. What's invisible software? Invisible software and technology is the stuff that you don't even see running.

That's doing things on your behalf without you having to ask. That's the key. Without you having to ask.

Without you having to prompt. Because it already knows you. Who's best suited for that? Apple.

Privacy. All the devices. I'm staring at an iPod, an iPad, an iPhone, AirPods, Macs and Pros, MacBooks, Pros, TVs, speakers.

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The only thing they haven't made watches. The only thing they haven't made is water bottles. What's the highest adopted thing on planet earth? Oxygen, water, food.

Apple, you want to hit 8 billion people? Ding, ding, ding, brother and sister. You've been thinking about this all wrong. Hydration is one of the leading indicators.

Everyone's carrying around Stanley cups. Stanley ran away with it. I'm just here to tell you.

All right. Here's the thing, y'all. Um, what are you going to do? What are you going to do about it? I'll tell you what you're going to do.

You're going to pick up the phone. You're going to give me or someone like me a call. And you're going to ask them, how do I create invisible software for my customers that deliver value to them continuously without them having to do anything? And they continue to pay me a subscription fee.

That's your answer.