Most data for today’s episode was provided by our partner Multiples.vc, your go-to source for verified M&A valuation multiples and public comps based on analyst estimates, at a fraction of the price of legacy data providers.

With this monthly format, we aim to unify market & valuation data into a single episode, so you don’t need to check various sources for a complete picture. Here’s what we’ll cover today:

We have a lot on the agenda, so let’s jump in👇

The dominant macro story of May is still the Iran war, further along and no closer to resolved.

As of today, Trump posted that a deal has been "largely negotiated," with terms expected to include reopening the Strait of Hormuz and Iran surrendering enriched uranium.

Nothing is signed.

Brent is trading around $103 per barrel, still more than 40% above pre-war levels, and the Strait remains functionally blocked. The S&P 500 hit a record 7,412 and the Nasdaq set all-time highs on May 11, even as Trump rejected Iran's latest proposal the same week.

The pattern from April held: markets price in resolution before the diplomacy delivers it. 84% of S&P 500 companies beat EPS estimates in Q1, which gives the market cover to look through the oil shock. Firm inflation and elevated energy prices are tempering Fed rate cut expectations, but equities are ignoring that too.

The other part is still AI. Against that backdrop, here is where the private mega-cap market stands.

The top of the table tells an AI concentration story that has only intensified since April.

SpaceX leads at #1 with $1.25T. On May 20 it formally filed its S-1 targeting a Nasdaq debut under SPCX as early as June 12, at a $1.75 to $2 trillion valuation target — the largest public offering in history if it prices. xAI appears separately at #6 at $230B, reclassified as a subsidiary post-merger.

OpenAI sits at #2 at $852B, up 13 positions after closing a $122B round on March 31, anchored by Amazon ($50B), Nvidia ($30B), and SoftBank ($30B). The company is generating $2.6B in monthly revenue with ChatGPT at 900M weekly active users.

Anthropic is the more interesting valuation story. Formal mark sits at $380B from the February Series G. Bloomberg reported in April that investors have offered $800B+ for a new round, which Anthropic has resisted. Annualized revenue reportedly hit $30B by end of March, up from $9B at end of 2025. Secondary markets are now pricing Anthropic at a premium to OpenAI for the first time.

ByteDance slips two to #5 at $330B. Ant Group (#7, $210B), Stripe (#8, $159B), Databricks (#9, $134B), and Waymo (#10, $126B) are stable. Five of the top six names are AI-first. The SpaceX S-1, OpenAI's $852B close, and Anthropic's resistance to $800B offers all landed within six weeks of each other. The private AI market is not waiting for public markets to catch up.

Here’s our 2026 IPO list based on rumours, plans, and status quo of their operations:

The 2026 IPO pipeline remains deep, with 50 named candidates spanning AI infrastructure, fintech, defense, healthcare, and consumer platforms. The list reflects both pent-up supply from years of subdued public market activity and a more selective investor base demanding clear paths to profitability before opening day.

The AI infrastructure cohort is the most watched: Anthropic, OpenAI, Perplexity AI, ElevenLabs, and Databricks collectively represent the largest concentration of potential market cap in any single IPO class in recent memory.

SpaceX (Starlink) is the most imminent listing on the list and the biggest story of the month. It formally filed its S-1 on May 20, targeting a Nasdaq debut under SPCX as early as June 12, at a valuation of $1.75 to $2 trillion. If it prices at the midpoint, it would be the largest IPO ever recorded, more than doubling Saudi Aramco's $29B raise. Most other names remain far from filing.

In light of very few public listings in the last few months, M&A has surged to become the more critical path for liquidity.

M&A activity remains robust.

2026 is tracking to become one of the most capital-intensive M&A years on record, even with deal volume YTD running well below the 2021 peak.

Average deal size has reached $260M in 2026 to date, the highest figure in the dataset going back to 2015, surpassing even the post-pandemic 2019 high of $208M.

Total volume for the year is approximately $1.7 trillion through May, with the full year on pace to approach or exceed the $3.2 trillion recorded in 2025.

The trend reinforces the bifurcation story playing out across private markets: fewer transactions, but meaningfully larger ones.

The era of broad-based deal activity has given way to concentrated, high-conviction consolidation in energy, infrastructure, and AI.

The largest deals of the past 30 days are dominated by two themes: energy infrastructure consolidation and AI capability acquisition.

Dominion Energy, acquired by NextEra Energy at $66.8B, is the standout transaction, priced at 3.8x revenue and 8.4x EBITDA. The deal signals that large-scale utility assets continue to attract strategic buyers willing to pay infrastructure-level multiples for regulated, long-duration cashflow. TK Elevator, acquired by KONE at $34.4B, is another capital-heavy industrial deal, clearing at 3.2x revenue and 18.4x EBITDA.

Cohere announced their planned merger with our portfolio company Aleph Alpha. Data in table above as per Multiples.vc. Unfortunately, due to my own involvement in Aleph Alpha, I can’t comment beyond the press announcements 🤐

Top 10 largest deals median: $14.5B EV at 3.6x revenue, versus April's $6.5B EV at 5.6x revenue. Deal sizes are larger but multiples are more disciplined.

The gap between blue-chip consolidation transactions and the broader market remains substantial.

Premium multiples in M&A are being paid selectively and primarily in two categories: unique assets and cybersecurity infrastructure.

Sachem Cap, acquired by Industrial Realty Group at a 72.3x revenue multiple, is a statistical outlier likely driven by asset-specific dynamics rather than sector-level pricing. Rajasthan Royals at 21.4x (Sports/E-Sports) and LayerX at 20.5x (Cybersecurity, acquired by Akamai) represent more interpretable premiums.

Strategic buyers are paying up for cybersecurity scarcity. LayerX and Astrix Security (16.0x, acquired by Cisco) both cleared above 15x revenue, consistent with the broader trend of enterprise security platforms commanding premiums unavailable in other software categories. Catalyst Pharmaceuticals, acquired by Angelini Pharma at 7.0x revenue and 13.9x EBITDA, anchors the biopharmaceuticals end of the table with more disciplined pricing.

The top 10 by EV/Revenue median is 14.8x, versus April's 6.7x showing a significant step-up driven by cybersecurity and unique asset premiums this month.

Compared to April, multiples are recovering at the top end while the overall market holds near its post-2022 floor.

The correction that began in late 2024 looks complete.

Let’s start with a snapshot of top companies based on EV / NTM Revenue multiples. For all analysis below, we exclude companies with market caps below $1B and non-meaningful multiples above 100x.

Top 10 average moves to 19.3x and median to 16.3x, up from 16.1x average and 13.8x median in April. In short: the floor held in April and multiples are re-rating upward in May.

Palantir leads at 35.3x, down from 38.3x in April but still commanding the widest premium, with 58% revenue growth, 86% gross margin, and 61% EBITDA margin.

CrowdStrike (26.1x, up from 15.8x) and Cloudflare (24.3x, up from 21.4x) both re-rated meaningfully. AppLovin (17.8x, up from 16.3x) stands out on efficiency: 85% EBITDA margin paired with 40% growth. SoundHound (12.7x, up from 10.9x) remains the only unprofitable name at -16% EBITDA margin.

At the index level, Top 10 average EBITDA margin holds at 38% (unchanged since April), with the overall market median ticking up to 2.3x from April's 2.2x.

Below is the EV/NTM Revenue trendline, the top 50 list, the multiples split by sector, and the efficiency benchmarks.

One metric just jumped 20% in a single month 👇