There’s a familiar hum in the air these days — a kind of adrenaline-fueled, frenzied vibration you only hear when an industry collectively decides that the future has arrived early and that fortunes are there for the taking. In other words: There’s a gold rush going on in AI (actually more than one).
And I don’t just mean the frontier-model builders, hyperscalers, or the chip makers who can’t build fabs fast enough to satisfy the planet’s appetite for compute. No, this fever has spread downstream to what we politely call “smaller startups.” Of course, in AI, “small” is a relative term. Tens and hundreds of millions are now the new rounds, because why not? When the pitch deck has the word “agentic” in it and the founders once bumped into someone from OpenAI in a coffee shop, apparently, the checkbook levitates on its own. Like the song says, “defying gravity.”
If you don’t believe me, go read the recent New York Times piece on the topic because you need to see it for yourself. The article lays out, in living color, just how ridiculously frantic things have become. VCs are flying cross-country at a moment’s notice, showing up uninvited to founders’ apartments, offering term sheets before the first meeting ends — or, in some cases, before the meeting even begins. No diligence, no hesitation, no shame.
You read these anecdotes and instinctively chuckle — until you realize they’re real. This isn’t Silicon Valley satire or an HBO script. This is the AI investment climate of late 2025. Following the founders to their rock climbing sessions, as it’s the only time they have to talk to the VC. Flying founders to Vegas to drive Ferraris. If that is the stuff that made it into the article, imagine what the VCs are doing that “wasn’t fit to print”.
And as I read it, my internal native intelligence (see what I did there) toggled between two familiar refrains: “A fool and their money…” and “I’ve seen this movie before.” Actually, if I’m being honest, I’ve seen it more than once, and I know exactly how it ends.
Yes, I can already hear the protests: “Alan, you’re missing it. Shimmy, this is a whole new paradigm. The rules have changed. Gravity is suspended.” My friends, I have lived through enough of these hype cycles to assure you: Gravity always shows up. You can only defy it for so long. It may be fashionably late, but it gets here. And right now, there’s an awful lot of dry powder coming into play, desperately seeking AI nirvana.
Now, don’t misunderstand me. There will be winners — huge, generation-defining winners. There will be startups that genuinely do break free of the Earth’s pull, the kind that go from garage to galactic in what feels like a single funding round. The ones powered by the right combination of insight, timing, and a VC willing to outbid every other VC before the founders finish their iced lattes. There will be others that are living proof that sometimes it’s much better to be lucky than smart. Some of these companies will become pillars of the next decade.
But for every one of those, there will be a whole universe of others that end up as this era’s pets.com: the cautionary tales, the punchlines, the brands we reference years later with a knowing smirk. And here’s the thing, VCs already know this. Their models assume it. They aren’t ignorant of the bodies littering the path to their 10-baggers. Failure is baked into the business model like chocolate chips in a cookie. The casualties are a feature, not a bug.
And the founders? Oh, don’t worry about them. They’ll be just fine. Right now, they’re being pursued with all the subtlety of teenage boys in heat, begging the prettiest girl at the prom for a dance. They’re fielding inbound from every fund with an LP and a pulse. If they hit, they’ll be billionaires. If they don’t, well — there’s always the next startup. And since they’re playing with OPM — Other People’s Money — failure just becomes another line item in a very profitable education. A base salary in the mid-six figures doesn’t hurt either. The next batch of VCs? Many will come straight from these founders who took the ride, cashed in at the right moment, and now want to get a taste of the other side of the table.
But I’ll tell you who I do feel for: The workers.
These are the folks getting swept into the vortex like debris in a tornado. They’re being told that big-tech isn’t hiring anyway, so this is their shot, their chance to be part of something scrappy, something bold, something that — if everything goes right — might change the world. They’re asked to take less cash, more risk, more hours, more pressure, less stability, and less work-life balance (you remember that right?). But don’t worry, they’re told, you’re getting options. Vesting over 48 months, naturally. No need to ask what percentage of total equity those shares represent. Just trust us — the strike price is cheap too.
I wish I could say this ends well.
But I’ve seen this movie. Most of those options will make lovely wallpaper. Some will make better toilet paper — if they’re soft, at least. There will, of course, be the occasional Willy Wonka golden ticket, handed out to a handful of employees who were in the right place at the right time. Those folks aren’t bratty kids who fall into chocolate rivers; they’ll be rewarded handsomely and will probably go on to found their own startups eventually — likely with friends they met at the first one, and based on technology they built while employed there.
Hollywood Central Casting couldn’t write it better. Hollywood and tech share a lot of DNA, actually. They both love sequels. They both run on mythmaking. And they both recycle the same plot lines with new actors and slightly updated dialogue. The AI boom is no exception.
Yes, AI VC dealmaking is moving faster than anything we’ve seen before. The pace is reckless, the checks enormous, the due diligence thin enough to see daylight through. When term sheets move at the speed of a text message and verification of claims gets the level of scrutiny you apply to code you just vibed, you know FOMO is driving the train.
Mitch Ashley, VP & practice lead at Futurum Research, put it this way: “The pace of AI investing right now looks akin to acceleration without the normal controls. Capital is moving faster than the technology ROI, and valuations are rising on the promise of agentic systems that many teams are still learning how to build. We’ve seen versions of this cycle across multiple eras, and the pattern is very familiar. The industry will get the breakthroughs, but it will also get the correction that arrives when inflated expectations outpace discipline.”
Let me give you my take, the Shimmy take. And this one hits closer to home than usual Shimmy takes. How do I know all of this? Because it’s my own life story I am looking at on the screen. Yeah, this is the part where the guy who’s been around long enough to live through the web bubble, the mobile boom, the cloud explosion, the blockchain detour, and the SaaS supercycle pipes up. I have played most of the different parts in this script and know from experience how it goes. It’s like Groundhog Day or some Twilight Zone episode. At various times, I have been all of these players.
So look, I get it. I lived it. High risk, high reward. If this stuff is in your blood, it’s intoxicating. You can’t not play. I spent more than two decades living in this world and, truth be told, there is nothing quite like it. The thrill, the energy, the possibility — it’s a kind of addictive drug all its own. It pulls you in, and if you’re not careful, it will suck you dry and leave you burnt out and battered.
Hey, don’t feel sorry for me here. It has afforded my family and me a great life, and I have done things I never dreamed I would do. But I consider myself one of the lucky ones. Not widely lucky, but lucky to get out alive, with my skin and sanity intact, and enjoy the fruits of all that hard work. But not everyone does and remember that.
You see, here’s the thing about movies and business cycles: After you’ve seen the third or fourth version of the same storyline, you realize you don’t need to stay for the ending. You already know it. The names change, the technology changes, the valuations sure as hell change — but the arc? The arc is eternal.
And AI in 2025? It’s just the latest, biggest blockbuster in a long-running franchise.
Buckle up. Enjoy the spectacle. But don’t kid yourself: It’s still subject to gravity. You really can’t defy gravity (not even in the land of OZ). And the credits always roll.
