When I think about AI IPOs, I can’t help recalling C3.ai’s debut. Back in late 2020, C3.ai went public at $42 a share and almost immediately became the poster child of AI hype. Within a few weeks, its stock shot up to about $177, which was a more than fourfold increase. 

I remember the frenzy on Reddit and trading forums. Everyone thought it was the next Nvidia. But the party didn’t last. By the end of 2022, C3.ai had tumbled to around $10 per share. If you bought at the peak, you were left holding the bag. However, the early investors obviously made a substantial amount of money.

The company’s growth didn’t keep up with the lofty expectations, and reality set in. This taught a harsh lesson that a hot IPO can turn ice-cold once the initial excitement fades. C3.ai wasn’t alone.

Early 2023 saw a mini-mania for anything labelled “AI.” One small-cap example was BigBear.ai (ticker BBAI). Its stock exploded by about 500% in a matter of weeks after OpenAI’s ChatGPT burst onto the scene and retail traders piled in. BigBear.ai was a relatively unknown analytics firm, but it suddenly gained recognition as the next big thing in AI. 

Of course, that spike was driven more by hype than fundamentals, and such spikes often retrace just as fast. By mid-2023, much of that initial gain had evaporated as reality (and short-sellers) caught up. These whiplash stories aren’t to scare you off. They’re to remind us that volatility is the norm for new technology stocks. As an investor, especially a retail investor, you have to be ready for wild ups and downs in the early days of an AI IPO.

On the other hand, some AI-related companies have managed to justify their hype over time. Palantir, which is not a pure AI company but is often lumped in with them, had a bumpy ride after its 2020 listing, only to see renewed interest when it pivoted hard into AI in 2023. Its shares climbed again as it rolled out new artificial intelligence products for its clients. The takeaway is that initial IPO pops (or drops) don’t necessarily predict a stock’s long-term path. But you need patience and strong nerves to ride out the stormy first year of an IPO.

Retail vs. Seasoned Tech Investors: Different Mindsets

It’s important to know who you are as an investor. A retail investor is simply a regular individual who puts their own money into the market (which is most of us reading this). A seasoned technology investor might be someone with years of experience trading tech stocks, or even a venture capitalist or industry insider. The difference in approach can be huge.

Retail beginners often get drawn in by the story or the brand. If you’re new to investing, you might buy a stock because everyone on social media is hyped about it or because you love the company’s product. I’ve seen friends invest money in an AI IPO simply because they believe “AI is the future”  with little understanding of the company’s actual finances or risks. Retail investors also tend to invest smaller amounts and often do not diversify their investments extensively. There’s no shame in being a newbie (we all start somewhere), but it means you have to be extra careful about doing homework and not getting swept up in meme-stock energy.

Seasoned technology investors (including savvy individuals and institutional players) take a more clinical approach. They’re the ones reading the SEC filings, scrutinizing the balance sheet, and comparing the company to its competitors. 

They will ask questions like “Does this startup actually make money?” What’s its growth rate? For example, after the IPO drought, many pros are insisting on seeing a path to profitability, not just big promises. In 2023, several tech IPOs (even outside AI) were chosen for their solid finances. These were companies like Arm and Instacart that were already profitable before going public. A seasoned investor will delve into those details, whereas a beginner might not even know where to look.

Another key difference is risk management. A professional investor may employ strategies such as setting stop-loss orders or hedging with options to mitigate downside risk. Retail investors often buy and hold or sell on emotion. I’ve personally learned (the hard way) that having an exit plan matters. During the C3.ai craze, a seasoned friend of mine sold part of his position when it doubled, locking in gains, while I rode my small stake up and down again. Lesson learned. 

That said, seasoned folks aren’t immune to mistakes. They can get caught in hype, too, just on a bigger scale. However, generally, incorporating seasoned investor thinking into your process (such as conducting due diligence and considering valuation metrics) can help keep your portfolio out of trouble. And if you’re somewhere in between, maybe you’ve traded stocks for a while but not specifically tech IPOs, you should balance the excitement of a new AI play with a sober look at the fundamentals. 

Even experienced investors can struggle to keep up with the latest trends. The key is to understand your investment type and make decisions accordingly. If you’re retail, maybe don’t go all-in on a single hot IPO. If you’re more seasoned, remember that sometimes gut feeling or user perspective (which retail folks often rely on) can complement the cold numbers.

The Caseway Rumour: Small Cap AI IPO?

Let’s talk about one specific AI startup that’s been generating whispers and rumours, which is Caseway. If you haven’t heard of it, Caseway is a legal technology company that leverages AI to accelerate legal research. However, it also offers other products, such as court-form AI and a bespoke agent that enables organizations to upload millions of documents into it.

It’s an AI system for sifting through court decisions and legal documents in seconds. It’s the kind of behind-the-scenes application that isn’t flashy like self-driving cars, but could be super helpful (lawyers spend hours on research without software like this). Word on the street (or rather, word in some investor circles I lurk in) is that Caseway might be considering a small-cap IPO soon, possibly in early 2026. 

This isn’t a headline you’ll find on Bloomberg yet. It’s more like startup community chatter. I actually reached out to Alistair Vigier, the CEO of Caseway, for comment. He very politely told me he “can’t confirm at this time” that any IPO is in the works. 

Classic CEO response. Reading between the lines, that’s neither a yes nor a no. They might be keeping things under wraps, or perhaps they haven’t decided yet. What we do know from public info is that Caseway has been fundraising in other ways. In early 2025, Caseway announced it was raising money via a SAFE (Simple Agreement for Future Equity) from accredited investors. That basically means private investors give funding now in exchange for a promise of shares later (usually when a priced round or IPO happens). 

The fact that they’re using a SAFE with a 20% discount on a future round suggests that they anticipate an event where that discount will become valuable. Often, that’s a big venture funding round or an IPO down the road. They’re likely using the funds to improve their AI and hire more engineers (legal AI is a tough nut to crack, after all). If Caseway does go for a small-cap IPO, it might list on a smaller exchange or aim for a modest raise. 

For example, they could try a Canadian exchange (since Caseway has Canadian roots) or NASDAQ if they want exposure in the United States, but not shoot for a multi-billion valuation. Small-cap IPOs don’t get the Wall Street spotlight like a Databricks or an Arm, but they can be interesting for retail investors who want to get in early on a niche player. 

Liquidity in Early IPOs for AI

Please note that small caps can indicate low liquidity. If only a few hundred thousand shares trade a day, you might have a hard time selling in a pinch (more on liquidity soon). And prices can swing wildly on any news, since a couple of enthusiastic (or pessimistic) traders can move a thinly traded stock a lot. It’s the classic high-risk, high-reward scenario. 

Big players like Westlaw or LexisNexis dominate the legal research market; can Caseway capture enough market share to grow rapidly? If they IPO, the prospectus should reveal their user counts and revenues (they noted 2,205 total users as of early 2025, which is small, but it’s early days). In any case, keep an eye out for an official announcement. 

Often, these “rumours” come true once the IPO window opens and a company sees an opportunity. And kudos to Alistair Vigier, he answered a random inquiry but stayed tight-lipped. I can respect that. He’s doing his job of not spilling the beans until the time is right.

Why Liquidity Matters (A Lot)

Whether you’re investing in a mega IPO or a tiny one, one concept you’ll hear about is liquidity. It’s a fancy term for how easily you can buy or sell an asset without dramatically affecting its price. For stocks, especially IPO stocks, liquidity is a big deal for a few reasons:

Liquidity for investors (you and me). If a stock is highly liquid, you can sell it quickly at or near the market price. If it’s illiquid, you might struggle to find a buyer, or you’ll have to drop your price a lot to attract one. Imagine you bought shares in a small AI company, and bad news comes out. If only a handful of people trade it, you could be stuck or face a steep price hit to exit. 

This is called liquidity risk, the risk that you can’t find a trading partner when you need to sell your stocks. Illiquid stocks often have big spreads between the bid and ask prices. I once invested in a micro-cap technology firm (not an AI company). When I wanted to exit, I received about 15% less than the last traded price because the market was so thin. I learned that you should always consider volume and float (i.e., how many shares are currently trading).

Liquidity for early backers and employees

From the company side, an IPO is a liquidity event. Venture capital funds and early angel investors have their money tied up in the startup. An IPO lets them finally sell some shares and return capital to their investors (the fund’s limited partners). Employees with stock options or founders can also cash in on years of work (buying houses, paying off loans, and living a better life than eating noodles all the time). There’s been a drought of IPOs for a while, and many VC funds were getting antsy because they couldn’t easily exit their positions. An interesting example is OpenAI, but it’s not publicly traded. 

Still, in 2023, it arranged a significant employee share sale at a valuation of approximately $86 billion, allowing employees and early backers to obtain liquidity without an IPO. That deal became shaky when their CEO was unexpectedly ousted, but it highlights the significant demand for an exit when a startup has been private for an extended period.

Liquidity and stock performance

A liquid stock tends to exhibit less drastic price swings in response to large orders. With a liquid large-cap (say Apple or Google), a single investor selling $5 million worth won’t move the needle. However, in a thinly traded AI startup, a sell order of that size could cause the price to plummet in minutes. 

Many artificial intelligence companies going public in 2025 may initially have moderate liquidity, not as low as a penny stock, but nowhere near that of a blue chip. Over time, if the company performs well and attracts more investors, liquidity improves. Until then, volatility can be higher. This is why you sometimes see IPO stocks jump or drop 20-30% in a day; there isn’t a massive pool of buyers and sellers yet, so any imbalance hits hard.

Investor psychology 

Liquidity also has a psychological aspect. For a retail investor, knowing you can quickly sell a stock if you need cash is comforting. If you feel stuck in an illiquid position, it can lead to panic or frustration. One of the golden rules is don’t put money into an IPO (especially a smaller one) that you might need back soon. Treat it as money locked up for a while, because in a crunch, you might not be able to access it without incurring a significant loss.

Liquidity is like the oil in the engine of the stock market. When it’s there, things run smoothly, and when it’s not, everything grinds and jerks. As an investor, you want to be aware of it. Check the trading volume, see how many shares are being offered in the IPO (a larger float usually means better liquidity), and consider the investor base. A stock that’s held mainly by a few insiders might not trade much. On the other hand, if an IPO is extremely popular with retail investors and has a robust daily trading volume, you have more flexibility to enter or exit.

The 2025–2026 AI IPO Pipeline: Who’s Coming to Market?

Which AI companies might hit the public markets in the next couple of years? It’s a mix of big and small names…

Databricks: 

This is a heavyweight in the data analytics and AI platform space. Every tech investor has been watching Databricks. They just raised a staggering $10 billion in late 2024, so they have cash. CEO Ali Ghodsi candidly said, “It’s dumb to IPO this year,” referring to 2024, citing economic uncertainty and even the United States election as factors. 

He indicated the earliest Databricks would go public is 2025, and it could slip to 2026. Why the wait? One reason he gave is related to employee liquidity. If they IPO’d in late 2024, employees would be subject to the lock-up period during a volatile time, which he wanted to avoid. In the meantime, Databricks let some early employees cash out part of their stakes through that massive funding round. 

By 2025 or 2026, if the market remains stable, I expect Databricks to be one of the largest tech IPOs in the market. They might be valued at over $ 40 billion easily. For investors, it’s attractive because Databricks is a leader in enabling AI for enterprises (think of all the companies that want to use AI on their data, wellDatabricks helps them do it). Just keep in mind that the valuation will likely be huge; the upside might already be partly “priced in” unless they continue to grow at a rapid pace.

CoreWeave:

This one is less well-known to the general public but is a darling in the AI infrastructure world. CoreWeave offers cloud services specifically designed for AI workloads. They rent out the type of GPU-packed servers that train AI models, competing with Amazon AWS and Microsoft Azure in this niche. According to Reuters, CoreWeave is aiming for a valuation of over $35 billion, with an IPO expected in 2025.

That is huge considering this company was valued at $2 billion just a couple of years ago. It reflects how demand for AI computing power has skyrocketed (everyone and their cat is training AI models now, and there’s a shortage of Nvidia chips to do it). 

CoreWeave’s backers include Magnetar and even Nvidia itself, so there’s confidence behind it. If it IPOs in Q2 2025 as rumoured, watch it closely. It could be one of those “picks and shovels” plays on the AI boom (selling the infrastructure to all the AI aspirants). High valuation, though, so as an investor, I’d scrutinize their revenue. Are they just burning cash to grow, or do they have steady contracts?

SymphonyAI: 

This is a company you might not have heard of unless you’re deep in enterprise AI. A tech veteran founded SymphonyAI, and it focuses on applying AI to different industries (from retail to finance). It’s reportedly profitable, with a $500 million revenue run-rate, which immediately sets it apart. Not many AI startups can claim that. 

In late 2024, news emerged that SymphonyAI had hired a CFO with IPO experience and was in discussions with banks about a potential public offering, possibly in the second half of 2025. A profitable, diversified AI company could attract significant interest because it checks the “financial stability” box that big investors like. Keep an eye out for this one; although it may not have the same buzz as an AI chatbot company, it has solid numbers to back it up.

Others in the wings: There are several more likely contenders. Hugging Face (an AI model-sharing platform beloved by developers) has been speculated as a future IPO, though nothing has been confirmed. Anthropic (maker of a ChatGPT rival) raised tons of money from Amazon and others; they might stay private longer or could surprise us if they need more capital. 

OpenAI itself, despite the share sale mentioned earlier, is unlikely to go IPO soon. Its structure is complex, with a nonprofit governing body and a profit-generating arm, and it also has Microsoft as a funding partner. They don’t need IPO cash right now, having recently raised around $40 billion, and Sam Altman (their CEO, who had a wild ride being fired and coming back) has downplayed near-term IPO plans.

Investing in IPOs in the artificial intelligence space is not for the faint of heart, but it’s hard to ignore if you’re excited about technology. For beginner retail investors, my advice is: enjoy the story and vision of these AI companies, but also ground yourself in some facts. Read summaries of the prospectus (you don’t have to slog through all 200 pages, but at least check revenue, losses, and growth rates). Be ready for volatility and don’t throw in money you can’t afford to have tied up for a while. 

Perhaps set some rules, such as “If it doubles, I take some profit” or “If it drops 50%, I re-check my thesis rather than just panic selling.” Basic risk management goes a long way. For more seasoned technology investors, this upcoming IPO wave presents an opportunity to potentially get in on the following big AI winners early; however, you are all familiar with the due diligence drill. Focus on the moat of these companies. Do they have proprietary technology, or are they just riding the AI trend? 

Examine their customer base and backlog, particularly for enterprise AI solutions like Databricks or SymphonyAI. Big recurring contracts are gold. And importantly, valuation does matter, even in an AI hype cycle. We learned that in 2021–22, when many high-flying tech stocks got brutally cut down to size. 

So, a great company at an overly high price can still be a bad investment. I’m planning a barbell approach. Perhaps consider investing in one or two of the “big fish” AI IPOs for the long term (those I believe have staying power), and a small speculative position in a smaller IPO, such as Caseway, if it materializes. This would essentially be my fun money for a potential high reward, knowing it comes with a high risk. And I’ll keep some cash on hand. 

IPO season can bring surprises, and having liquidity (there’s that word again) means I can jump on an opportunity or weather a downturn without selling stuff I don’t want to sell. Investing in AI IPOs combines two highly unpredictable elements: cutting-edge technology and the stock market. Both can surprise you. 

Do your homework, stay level-headed, and don’t let the allure of “the next NVIDIA” blind you to the basics of good investing. Whether you’re clicking buy from a Robinhood app in your living room or analyzing deals with an experienced eye, the goal is the same… Make thoughtful decisions and hopefully profit from the incredible innovations happening in AI. Good luck out there, and let’s see what 2025 brings!