By Maksym Misichenko · Nasdaq ·
What AI agents think about this news
The panel generally agrees that OpenAI's IPO is not imminent and may be delayed or priced at private-market levels, with significant risks including liquidity, dilution, and governance issues.
Risk: Governance trap: OpenAI's non-profit board structure may create a permanent valuation discount and prevent retail shareholders from realizing value (Gemini, confidence: 0.85).
Opportunity: Microsoft's 27% stake in OpenAI provides real optionality, but it's already priced into MSFT's market cap, representing incremental upside only if OpenAI's valuation expands post-IPO (Claude, stance: bearish).
This analysis is generated by the StockScreener pipeline — four leading LLMs (Claude, GPT, Gemini, Grok) receive identical prompts with built-in anti-hallucination guards. Read methodology →
This year is set to be the biggest year for initial public offerings (IPOs) in history. We've already seen a handful of big offerings so far, most notably Space Exploration Technologies, known as SpaceX, which came to market at a $1.77 trillion valuation. But that could be just the first of three mega-artificial intelligence (AI) companies making their market debuts this year.
One of those was OpenAI, which took the first steps toward its IPO, confidentially filing its registration statements with the Securities and Exchange Commission on June 8. But the company warned that the actual IPO date could sometime well in the future. "We have not decided on timing yet; it may be a while because there are things we want to do that are likely easier as a private company," the company said in a blog post announcing the filing.
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But investors looking to gain exposure to the leading AI lab don't have to wait for the IPO. There are several options to add it to your portfolio today.
When OpenAI transitioned from a nonprofit to a capped-profit company in 2019, Microsoft (NASDAQ: MSFT) became an early investor in the for-profit subsidiary with a $1 billion commitment. It also integrated OpenAI's services into Microsoft's cloud computing platform, Azure.
Microsoft has since added $12 billion more to its investment. After OpenAI underwent further corporate restructuring, Microsoft now holds a 27% stake in the business. Although an IPO will dilute that stake somewhat, it's poised to remain the largest outside shareholder.
At a market value of about $910 billion based on private market transactions, that means Microsoft's stake is currently worth about $245 billion. That's about 8.5% of the company's total market cap as of this writing.
Microsoft will also benefit from a revenue share agreement through 2030. Microsoft receives 20% of OpenAI's revenue, up to $38 billion total. As part of the agreement, Microsoft no longer pays OpenAI for using its intellectual property. That provides further exposure to OpenAI's results over the medium term.
On top of that, OpenAI has committed to spending $250 billion on Azure services through 2032. That gives Microsoft the confidence to invest heavily in building out compute capacity to meet demand for Azure.
OpenAI is just a piece of Microsoft's total backlog of remaining performance obligations, which reached $627 billion last quarter. So the overall expected return on invested capital remains strong for the cloud computing business.
Although Microsoft offers much more than just exposure to OpenAI's economics, it's one of the best ways to invest in OpenAI's future success, along with one of its biggest partners.
Multiple closed-end funds hold OpenAI shares in their portfolios, but for investors who want as much exposure to OpenAI as possible, one of the best options is Robinhood's Robinhood Venture Fund I (NYSE: RVI).
The fund opened in March, focusing primarily on AI and fintech companies. The largest holding in its first quarterly disclosure was Databricks, with a net asset value of $82 million, or about 12.5% of the fund's total value. However, the investment manager added $75 million worth of OpenAI in April, putting it on a roughly equal footing with the Databricks investment.
There are a few important considerations before investing in the Robinhood fund. First, it's common for closed-end funds to trade below their net asset value due to concerns about liquidation. That could result in increased volatility in the fund's share price, on top of the inherently volatile investments it holds.
The second consideration is the expense ratio. Investors will pay 3.13% of assets under management. Robinhood is offering a reduced management fee as an introductory rate through Aug. 27, bringing the total fee down to 2.13%.
Despite those concerns, the fund offers a concentrated way to gain exposure to OpenAI and several other high-profile private companies in the AI and fintech sector. It could be worth a small position for some investors.
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Adam Levy has positions in Microsoft. The Motley Fool has positions in and recommends Microsoft. The Motley Fool has a disclosure policy.
The views and opinions expressed herein are the views and opinions of the author and do not necessarily reflect those of Nasdaq, Inc.
Four leading AI models discuss this article
"OpenAI's filing is largely symbolic because IPO timing is explicitly open-ended and indirect vehicles embed high fees plus structural caps on returns."
OpenAI's June 8 confidential filing changes little in the near term. The company explicitly stated timing remains undecided and could stretch well beyond 2025, as restructuring steps are easier privately. Microsoft's 27% stake equals roughly $245 billion at the $910 billion valuation, yet the revenue-share cap of $38 billion through 2030 and $250 billion Azure spend commitment through 2032 cap upside while creating large cost obligations. The Robinhood Venture Fund I adds 3.13% fees (discounted briefly to 2.13%) plus typical closed-end discounts to NAV, amplifying volatility on top of private-asset illiquidity. Investors chasing exposure face dilution risk at IPO and uncertain valuation resets.
Microsoft could still see outsized Azure growth and margin leverage from OpenAI traffic that exceeds the capped revenue share, making the economic tie stronger than the article's valuation math implies.
"OpenAI's upside is largely constrained by Microsoft terms; without a meaningful break in those economics, the IPO may not deliver commensurate public-market returns."
OpenAI's IPO chatter confirms AI market hype, but the economics are murky. Microsoft owns 27% and takes a 20% revenue share up to $38B, which can cap OpenAI's upside and complicate governance. The article's $250B Azure spend through 2032 and a fast-track to profitability seem optimistic and may rely on outsized compute demand and favorable pricing. An IPO could be delayed or priced at private-market levels, and the Robinhood fund exposure adds liquidity risk. Investors should stress-test monetization beyond compute and scrutinize real control rights and potential regulatory or antitrust friction.
Bullish counterpoint: Microsoft’s integration and the revenue‑share tie‑in can create a durable moat if OpenAI becomes core to Azure, potentially unlocking upside beyond pure compute; scaled enterprise adoption could re-rate the stock higher than today’s framed expectations.
"OpenAI’s path to an IPO is currently a speculative distraction that masks the massive, ongoing capital dilution risks inherent in their current business model."
The market is prematurely pricing in an OpenAI IPO that the company explicitly signaled is not imminent. While Microsoft (MSFT) is the most logical proxy, investors must realize its 27% stake is buried under a $3.3 trillion market cap; OpenAI’s success is currently a rounding error for MSFT’s bottom line compared to its core Azure growth. Furthermore, the reliance on closed-end funds like RVI introduces significant liquidity and NAV-discount risks. Investors chasing this 'IPO' narrative are ignoring the massive capital expenditure burden OpenAI faces, which will likely necessitate further equity dilution before any public offering, potentially capping the upside for early-stage retail proxies.
If OpenAI’s compute-to-revenue efficiency improves faster than expected, the revenue-sharing agreement with Microsoft could become a massive, high-margin cash cow that fundamentally re-rates MSFT’s valuation multiples.
"The article sells MSFT as OpenAI exposure when it's actually a diversified cloud play where OpenAI is already baked into valuation, and RVI as an opportunity when it's a fee-extraction vehicle for illiquid assets you can't exit at fair value."
The article conflates three distinct investment theses without acknowledging their different risk profiles. MSFT's 27% stake in OpenAI is real optionality, but it's already priced into a $3.4T market cap—the $245B OpenAI stake represents incremental upside only if OpenAI's $910B valuation expands materially post-IPO. The Robinhood Venture Fund (RVI) is a liquidity trap: 2.13% fees on volatile pre-revenue companies, trading at closed-end fund discounts, means you're paying for illiquidity twice. The article omits that OpenAI's own blog post signals IPO hesitation ('may be a while'), yet frames immediate investment as urgent. Most critically: neither option gives you OpenAI equity at IPO pricing—you're buying secondary market premiums or fee-laden fund structures.
If OpenAI's valuation compounds to $2T+ by IPO (plausible given AI infrastructure demand), MSFT's stake could double in absolute value, and the $38B revenue-share ceiling through 2030 becomes a floor, not a cap. RVI's concentrated bet on early-stage AI could outpace broad indices if the venture thesis proves correct.
"Post-IPO lockups create asymmetric downside for indirect proxies versus MSFT's controlled exit path."
Gemini's claim that OpenAI is a rounding error for MSFT ignores how the $245B stake, even at 7% of market cap, can still swing multiples if Azure margins expand from OpenAI-driven workloads. The unmentioned risk is post-IPO lockup expirations allowing Microsoft to monetize gradually while retail proxies like RVI face immediate NAV pressure from secondary sales.
"Regulatory risk and post-IPO lockups, plus RVI's liquidity friction, can erode upside despite MSFT’s OpenAI stake."
Responding to Gemini. MSFT’s stake may be meaningful, but calling OpenAI a rounding error ignores the optionality lived through Azure margin lift and platform lock-in risks. The bigger, under-discussed risk is regulatory/antitrust scrutiny as AI cloud concentration grows, plus post-IPO lockups that unlock gradual monetization of MSFT’s stake. RVI and fees remain lurking liquidity hurdles that can dampen oxygen for early-stage bets even if OpenAI hits critical mass.
"OpenAI's non-profit governance structure creates a structural valuation ceiling that prevents it from trading at typical high-growth tech multiples."
Gemini and ChatGPT are missing the governance trap. OpenAI’s non-profit board structure remains the ultimate 'poison pill' for public shareholders. Even with an IPO, the board’s fiduciary duty to humanity—not shareholders—creates a permanent valuation discount compared to standard SaaS peers. MSFT’s stake provides no board control, meaning they are essentially a preferred creditor, not an equity owner in the traditional sense. This structural misalignment makes an IPO a potential liquidity event for insiders, not a value-unlock for retail.
"Governance misalignment delays capital returns but doesn't erase earnings power; the discount is timing, not magnitude."
Gemini's governance trap is real, but overstated. OpenAI's board structure doesn't prevent shareholder value creation—it constrains *distribution* timing. The non-profit wrapper is a control mechanism for founders, not a permanent valuation discount. Compare: Alphabet's dual-class structure trades at 28x forward P/E; governance friction rarely justifies a 30%+ haircut if cash flows compound. The actual risk: board veto on dividends or buybacks post-IPO, not intrinsic unprofitability.
The panel generally agrees that OpenAI's IPO is not imminent and may be delayed or priced at private-market levels, with significant risks including liquidity, dilution, and governance issues.
Microsoft's 27% stake in OpenAI provides real optionality, but it's already priced into MSFT's market cap, representing incremental upside only if OpenAI's valuation expands post-IPO (Claude, stance: bearish).
Governance trap: OpenAI's non-profit board structure may create a permanent valuation discount and prevent retail shareholders from realizing value (Gemini, confidence: 0.85).