Bleeping Computer has the scoop -> Leak confirms OpenAI is preparing ads on ChatGPT for public roll out
Tibor on X spotted that ChatGPT’s latest Android App includes references to an Ads Feature, with
Reference -> x.com/btibor91/status/1994714152636690834
Microsoft & Open AI Deal Details – Executive Summary
Kakashii (Profile / X i.e. https://x.com/kakashiii111) has a really good write up and the key points are ->
It really does seem Microsoft was in a very strong position as this deal is heavily tilted in favor of Microsoft.
Microsoft & Open AI History I – Learning from its Mistake with investing in Facebook
When Microsoft invested $240 million in Facebook at a $15 billion valuation, they took a measly 1.9% equity.
This was a massive mistake. Taking a sizeable amount of equity would have been priceless. Satya Nadella obviously learned from that mistake.
For those who are older, Microsoft made the same mistake with Apple. IYKYK.
Microsoft & Open AI History II – The Right Approach with Investing in AI
The original Microsoft and Open AI deal is quite marvelous (for Microsoft)
This was a masterful deal and Microsoft and Mr. Satya Nadella should get a lot of credit for this.
Microsoft & Open AI Deal – Series A & Series B
Series A on July 22nd, 2019 -> $1 Billion invested by Microsoft and Matthew Brown Companies at an Unknown Valuation
Series B on Jan 23rd, 2023 -> $10 Billion invested by Microsoft and other investors at a $27 Billion Valuation.
These two investments meant that even after Series B Microsoft had 32.5% equity. More importantly, it means that even now, in Nov 2025, Microsoft still has 27% equity in Open AI and Open AI is wedded to Azure.
Microsoft & Open AI Deal – Current Deal Setup
Please see the first section of this post for more details. The key points are
It’s one heck of a deal for Microsoft.
From OpenAI’s perspective you could argue that Microsoft’s investments in 2019 and 2013 were key to Open AI becoming what it is.
Open AI Cap Table Executive Summary – 11/11/2025
Please Note: This is based on publicly available information and might be inaccurate.
Please Note: This is subject to change based on further fund raising by OpenAI and on sales by current investors and current employees.
Open AI Investments & Funding Rounds
You can also check Traxcn for a different take on OpenAI’s funding rounds -> OpenAI – 2025 Funding Rounds & List of Investors – Tracxn (https://tracxn.com/d/companies/openai/__kElhSG7uVGeFk1i71Co9-nwFtmtyMVT7f-YHMn4TFBg/funding-and-investors#funding-rounds).
Open AI Original Founding Details
OpenAI was originally founded as a Non Profit with $1 Billion of Grant Money from Peter Thiel, Elon Musk, Reid Hoffman, Infosys and others.
Open AI Seed Round Details
In 2016 OpenAI participated in YCombinator. The usual funding from YCombinator is $120K for 7% Equity.
It is not clear whether YCombinator took any equity. It is also not clear whether YCombinator invested any money in Open AI.
Open AI Series A Details
A master stroke by Microsoft where Microsoft invested $1 Billion in OpenAI on July 22nd, 2019 and got its foot in the door.
Open AI Series B Details
Microsoft invested $10 Billion at a $27 Billion valuation on Jan 23rd, 2023. This got Microsoft 32.5% equity.
Even now, after further rounds, Microsoft still has 27% equity in OpenAI.
Open AI Series C Details
This was a relatively small investment of $300 Million at an Unknown Valuation on April 28th, 2023.
As it is close after Microsoft’s $10 billion investment it would not be a surprise if the valuation was $27 or $30 Billion.
The investors included Tiger Global, Andreesen Horowitz, Founders Fund, Flat Capital etc. It almost seems like a ‘let the big players in Silicon Valley get a small piece’ round.
Open AI Series D Details
This was a $6.6 Billion investment at a $157 Billion valuation on Oct 2nd, 2024.
Investors were led by Thrive Capital and included Khosla Ventures, Microsoft, etc.
Debt Funding between Series D and Series E in October 2024
OpenAI took on $4 billion of conventional debt on Oct 7th, 2024 from Wells Fargo, UBS, HSBC, Goldman Sachs, etc. This was just a debt round and not VC funding.
Open AI Series E Details
This was SoftBank investing $40 Billion at a $300 Billion valuation on Mar 31st, 2025.
There were also other investors including Microsoft, Coatue, and Thrive Capital.
Some interesting details coming out on OpenAI & Anthropic’s Financial Projections.
OpenAI Financial Projections + OpenAI Path to Profits
Makes me a bit suspicious when all the numbers are such nice round figures ($20 billion, $100 billion, $200 billion). Are these projections or just wishful thinking?
Anthropic Financial Projections + Anthropic Path to Profits
Reference: https://www.wsj.com/tech/ai/openai-anthropic-profitability-e9f5bcd6
OpenAI vs Anthropic – Why is Anthropic projecting it will reach profits in 2028 itself? 2 years before OpenAI
Reference: https://www.theinformation.com/articles/anthropic-projects-cost-advantage-openai
These are three of the reasons postulated
What a strange world we live in. The great capitalists who were going to revolutionize the world and transform our lives now desparately need our tax dollars to survive.
Sam Altman of OpenAI was publicly claiming day before yesterday (Nov 6th, 2025) that OpenAI is not asking the US Government to backstop AI companies’ losses.
Behind the scenes, as far back as Oct 27th, OpenAI was asking the Trump government to expand the 35% Chips Act tax credit to all AI infrastructure.
A Comedy of Errors
Who would have guessed that a company with $20 billion a year in revenues (OpenAI), and which has made commitments to spend $1.4 Trillion over the next 8 years, might need Government assistance?
OpenAI is about to trigger an absolutely massive AI Bubble crash.
It might take 6 months to 2.5 years before things fall apart.
Why the delay? Because the US is desperate to not have its economy implode and will do everything it can to delay the inevitable. However, this is the triggering event, without a doubt.
All the people who had doubts. All the people on the fence. All the people who thought AI seemed to be too good to be true. All the people who were suspicious of 22 year olds becoming billionaires (on paper).
They all will think AI is the new big scam, not the new big revolution. Who knows – Perhaps it is both.
Everyone now knows that this is a new breed of Entrepreneur – The Government-Preneur.
Instead of Profits, the AI companies are looking for Government hand outs and Taxpayer Bailouts.
These are companies built not on great products and great business models. These are companies built on Privatization of Profits and Socialization of Losses. Regulatory Capture. Government Backstops. Taxpayer Bailouts and Taxpayer Bailins.
Marvels not of Engineering, but of Financial Engineering.
Now we know why we were suddenly seeing so many articles claiming ‘Bubble are a holy cleansing fire’ and ‘Bubbles have benefits’ and ‘Bubbles lay the groundwork for the Next Generation of Great Companies’.
Sadly, this is the day that AI’s reputation got destroyed. The industry is looking for Bailouts and Taxpayer money even before it has started kindergarten. Amazing. Simply Amazing.
That’s it. That’s the post
Reference 1 -> https://x.com/sama/status/1986514377470845007
Reference 2 -> https://the-decoder.com/openai-ceo-sam-altman-expects-to-hit-20-billion-in-annual-revenue-by-year-end/
Reference: 1 million business customers: the fastest-growing business platform in history | OpenAI
Data Points from OpenAI’s post on reaching 1 million business customers
Thoughts on OpenAI’s data points and claims
This is certainly an impressive update by OpenAI.
On Feb 16th, 2024, OpenAI raised money at a $80 Billion valuation, nearly tripling its valuation in 10 months -> OpenAI Completes Deal That Values the Company at $80 Billion – The New York Times (nytimes.com)
A few days ago, end of August 2024, we found out that OpenAI is raising money at a $100 Billion valuation -> OpenAI Eyes $100 Billion Valuation – The New York Times (nytimes.com)
OpenAI’s Latest Funding – The Details
Thanks to CNBC for these details -> OpenAI in talks to raise funding that would value it at more than $100 billion (cnbc.com)
11 Thoughts on OpenAI’s $100 Billion Valuation
We really do live in the most interesting timeline. There is never a dull day in AI.
Deal AI - Deals, Funding, Acquisitions & Mergers in AI 