🔥 US-Iran Peace Deal, Anthropic… | Data Driven VC Summary

1. Key Themes

AI Lab Valuation Race: Anthropic Overtakes OpenAI at the Private Market Apex

Anthropic has surpassed OpenAI in private market valuation for the first time, reaching an estimated $965B versus OpenAI's $852B. Both have filed confidential IPO prospectuses, setting up what could be the largest software IPO in history.

"Anthropic is the highest valued private market company at an estimated $965B, overtaking OpenAI ($852B) for the first time. It also filed a confidential IPO prospectus. No timing given."

"At an estimated $965B secondary valuation, it would be the largest software IPO in history if it prices at that level."

AI Software Commands a Record Premium in M&A — Strategic Acquirers Paying 15x+ to Avoid Competing Later

The top 10 M&A deals by EV/Revenue posted a median of 18x in June (up from 14.8x in May), with AI software assets clearing at 15x–27x. The article frames this as preemptive capability acquisition, not traditional M&A logic.

"The top 10 by EV/Revenue median is 18x, up from 14.8x in May. AI software is commanding a higher premium month on month."

"Strategic acquirers are paying 15x-plus for AI capability rather than compete later."

The IPO Market Is Bifurcating: Mega Exits Now, Everyone Else Waits or Gets Acquired

SpaceX's $85.7B IPO — the largest in history — dominated the window. Meanwhile, Databricks, Canva, Revolut, and Stripe are all explicitly deferring to 2027 or later, leaving M&A as the realistic near-term exit for the broader pipeline.

"SpaceX went public on June 12 under SPCX, raised $85.7B in the largest IPO in history, and closed day one above $2.1T market cap."

"For everyone else on the list, M&A remains the more realistic near-term exit."

Geopolitics Drives Macro: Iran Deal Collapses Oil Premium, Lifts Equities

The US-Iran Islamabad Memorandum directly caused oil to drop ~$23/barrel and pushed equities to new highs, illustrating how a single geopolitical event can reorder macro conditions within weeks.

"On June 17, the US and Iranian presidents signed the Islamabad Memorandum at the Palace of Versailles during the G7 Summit, initiating a 60-day nuclear talks window. Brent collapsed to approximately $80, erasing nearly all of the war premium built since February."

"The S&P 500 reached approximately 7,500 and the Nasdaq topped 26,500."

Public Market Multiples: Top End Holds, Profitability Quietly Rises — Gap with Broad Market Widens

The top-10 software cohort is flat on revenue multiples (19.0x average) but meaningfully more profitable, with average EBITDA margins rising to 44% from 38% in May. The broad market median ticked down to 1.8x. The quality gap is compounding.

"The Top 10 average EBITDA margin rises to 44%, up from 38% in May."

"The top end is holding and getting more profitable. The gap with the broad market is not closing."

2. Contrarian Perspectives

Tether — a Stablecoin Issuer — Is Now the Third Most Valuable Private Company in the World, Ahead of ByteDance

The article flags this as a genuinely surprising data point, noting that a stablecoin infrastructure business has leapfrogged one of the world's largest consumer internet companies in private market valuation. This runs counter to the common assumption that AI and consumer tech dominate the value creation landscape.

"Tether followed OpenAI at $500B valuation. A stablecoin issuer now ranks above ByteDance. That is a sentence worth reading twice."

Databricks Is Actively Choosing Not to Go Public Despite Being the Most Profitable IPO Candidate

Despite $5.4B in annualized revenue growing 65% YoY and a $134B valuation, Databricks is explicitly deferring its IPO to at least 2027. This challenges the assumption that strong fundamentals create IPO urgency — in fact, the most profitable companies have the least pressure to access public markets.

"CEO Ali Ghodsi said in early June it would be a 'terrible year' to go public given the crowded IPO calendar, effectively deferring to 2027. It remains the most profitable name in the pipeline at a $134B valuation with $5.4B in annualised revenue growing 65% year on year."

OpenAI Pre-Announced Its Confidential S-1 Filing — Because It Assumed It Would Leak Anyway

Rather than the typical quiet-period secrecy of an S-1 filing, OpenAI announced it themselves, signaling a new norm where AI companies treat regulatory filings as PR events. No listing date was set, suggesting the filing is more about optionality than near-term execution.

"The company announced it themselves: 'We expect it to leak so we're just announcing it. We have not decided on timing yet; it may be a while.'"

3. Companies Identified

SpaceX Aerospace / Public Markets Completed the largest IPO in history at $85.7B, then immediately used public stock to acquire Cursor for $60B — the largest VC-backed acquisition ever — just four days later.

"SpaceX went public on June 12 under SPCX, raised $85.7B in the largest IPO in history, and closed day one above $2.1T market cap. Four days later, SpaceX agreed to acquire AI coding startup Cursor for $60B in an all-stock deal, the largest VC-backed acquisition ever recorded."

Anthropic AI Foundation Model / Private Now the highest-valued private company globally at ~$965B, overtaking OpenAI, with a confidential IPO prospectus filed.

"Anthropic is the highest valued private market company at an estimated $965B, overtaking OpenAI ($852B) for the first time."

OpenAI AI Foundation Model / Pre-IPO Filed confidential S-1 on June 8, valued at $852B, but with no listing date set.

"OpenAI (#31) filed its confidential S-1 on June 8, one week after Anthropic."

Cursor AI Coding Tool / Acquired Acquired by SpaceX for $60B (15x revenue) — the largest VC-backed acquisition on record, closing Q3 pending regulatory approval.

"Cursor, acquired by SpaceX at $60B (15x revenue), is the deal most of you reading this have a personal opinion on."

Databricks Data + AI Platform / Private Most profitable IPO candidate; $134B valuation, $5.4B annualized revenue at 65% growth. Explicitly deferring IPO to 2027.

"It remains the most profitable name in the pipeline at a $134B valuation with $5.4B in annualised revenue growing 65% year on year."

Tether Stablecoin Infrastructure / Private Valued at $500B, now the third-largest private company globally — ahead of ByteDance.

"Tether followed OpenAI at $500B valuation. A stablecoin issuer now ranks above ByteDance."

Palantir AI / Data Analytics / Public Leads the public top-10 cohort at 32.1x EV/NTM Revenue on 56% revenue growth, 87% gross margin, and 61% EBITDA margin.

"Palantir leads at 32.1x, down from 35.3x in May, on 56% revenue growth, 87% gross margin, and 61% EBITDA margin."

AppLovin AdTech / Public Described as "the most efficient business in the cohort" at 16.9x EV/NTM Revenue, 89% gross margin, and 85% EBITDA margin.

"AppLovin holds at 16.9x on 89% gross margin and 85% EBITDA margin, the most efficient business in the cohort."

MaintainX Industrial Operations Software / Acquired Acquired by Autodesk at 26.7x revenue ($3.6B) — the highest revenue multiple in the top M&A table.

"MaintainX, acquired by Autodesk at 26.7x ($3.6B)...lead the table."

StackAI AI Workflow Automation / Acquired Acquired by Asana at 25.0x revenue ($75M), second-highest multiple in the M&A table.

"StackAI, acquired by Asana at 25.0x ($75M)...lead the table."

Canva Design Platform / Pre-IPO Targeting 2027 IPO; COO cited the need to bed in its business model transition before facing public market scrutiny.

"COO Cliff Obrecht confirmed in April: 'We want to make sure the evolution of this business model is really bedded in so we're not having to explain ourselves to the market through a transitional period.'"

Revolut Fintech / Pre-IPO No S-1 filed; CEO pointing to 2028 at earliest.

"Revolut (#40) has not filed; CEO Storonsky pointed to 2028 at the earliest."

Stripe Payments / Private Remains profitable and liquid via secondaries — explicitly in no rush to go public.

"Stripe (#47) remains profitable, liquid via secondaries, and in no rush."

Equity Residential / AvalonBay Communities Residential Real Estate / M&A $69B deal at 11.2x revenue, 16.4x EBITDA — cited as evidence of large-scale residential assets clearing at infrastructure-tier multiples.

"A signal that large-scale residential assets are clearing at multiples historically reserved for regulated infrastructure."

Attio CRM / Sponsor Mentioned as newsletter sponsor; positioned as "the AI CRM for modern businesses."

"Attio is the AI CRM that keeps you ten steps ahead."

CrowdStrike Cybersecurity / Public 26.5x EV/NTM Revenue, essentially flat month-on-month; part of the top-10 public comps cohort.

Cloudflare Network Security / Public 24.8x EV/NTM Revenue, essentially flat.

Palo Alto Networks Cybersecurity / Public Enters the top-10 at 17.3x on 21% growth, 76% gross margin.

4. People Identified

Ali Ghodsi CEO, Databricks Publicly stated it would be a "terrible year" to go public, effectively signaling a 2027 IPO at earliest despite industry-leading fundamentals.

"CEO Ali Ghodsi said in early June it would be a 'terrible year' to go public given the crowded IPO calendar."

Cliff Obrecht COO, Canva Confirmed Canva is targeting 2027 for its IPO, citing a need to complete its business model transition before going public.

"COO Cliff Obrecht confirmed in April: 'We want to make sure the evolution of this business model is really bedded in.'"

Nikolay Storonsky CEO, Revolut Pointed to 2028 as the earliest realistic IPO window for Revolut.

"CEO Storonsky pointed to 2028 at the earliest."

Kevin Warsh New Fed Chair Held rates at 3.50-3.75% in his first FOMC meeting; nine of 18 officials signaled at least one hike by end of 2026.

"New Fed Chair Kevin Warsh held rates at 3.50-3.75% in his first FOMC meeting, but nine of 18 officials signaled at least one rate hike by end of 2026."

Andre Retterath Author, Data Driven VC Newsletter author and VC focused on data-driven investment methodology.

"Hi, I'm Andre and welcome to my newsletter Data Driven VC which is all about becoming a better investor with data and AI."

5. Operating Insights

1. Use Public Stock as Acquisition Currency Immediately Post-IPO SpaceX's playbook — IPO, then immediately deploy freshly minted public stock to acquire a high-value AI asset — represents an emerging M&A strategy for newly public companies. The all-stock structure for Cursor meant SpaceX acquired $60B in AI capability without cash outlay, just four days after listing.

"It then used its freshly minted public stock to acquire Cursor for $60B four days later. Fastest IPO-to-acquisition window in recent memory."

2. Track EBITDA Margin Trajectory, Not Just Revenue Multiples, When Benchmarking Your Business The top-10 public software cohort saw revenue multiples stay flat while EBITDA margins jumped from 38% to 44% in a single month. This suggests the market is increasingly rewarding profitability expansion, not just growth — a signal for operators about where to focus to justify premium valuations.

"The Top 10 average EBITDA margin rises to 44%, up from 38% in May...The top end is holding and getting more profitable. The gap with the broad market is not closing."

3. If You're Highly Profitable and Private, Staying Private Is a Strategic Choice, Not a Limitation Databricks, Stripe, and Canva are all demonstrating that the most fundamentally strong companies are actively choosing to stay private longer, using secondaries for liquidity and avoiding public market scrutiny during business model transitions.

"Stripe remains profitable, liquid via secondaries, and in no rush." "It would be a 'terrible year' to go public given the crowded IPO calendar."

6. Overlooked Insights

1. M&A Deal Size Is at a Historical Peak — Fewer but Much Larger Deals Average M&A deal size hit $270M in June — the highest in the dataset going back to 2015 — while YTD deal value reached ~$2.1T. This "fewer transactions, materially larger sizes" trend is underemphasized relative to the headline acquisitions, but has significant implications for smaller companies' exit prospects.

"M&A average deal size rose to $270M in June, up from $260M in May and the highest in the dataset going back to 2015. The trend holds: fewer transactions, at materially larger sizes."

2. Hardware Is Having a Breakout Moment in Public Market Multiples The article teases that hardware "just posted its biggest month-on-month jump in this dataset" but gates the full sector breakdown behind a paywall. Given the AI infrastructure buildout narrative, this is a potentially significant signal for hardware-adjacent investment theses that goes largely undiscussed in the free portion.

"Hardware just posted its biggest month-on-month jump in this dataset."