
OpenAI’s $200B Losses Need Amazon‑style Discipline
I have been thinking about the news that Sam Altman wants to take OpenAI public by the end of 2026, while the company is still projected to lose more than $200 billion before it turns a profit. A lot of people will look at that number and say it's reckless. I don't think it's that simple. Amazon wasn't profitable for years. Jeff Bezos used to joke about it. But Amazon was never unfocused. Every dollar went toward building infrastructure that nobody else was building, at a scale nobody else was willing to fund. No gimmicks, no side projects for the sake of headlines. Just a relentless, boring commitment to the long game. When profitability came, it came decisively. OpenAI has a version of that ambition. The Stargate infrastructure bet, the chip deals, the data center build, these aren't vanity projects. They're bets on a future where AI is as essential to business as electricity. What OpenAI is missing is the discipline layer that made Amazon's losses defensible. Sarah Friar, the CFO who has reportedly raised concerns about IPO timing, is exactly the kind of executive who could provide that. So is Fidji Simo, who joined to lead the Applications side of the business. Together they remind me of what Ruth Porat did at Google in 2015, she came in from Wall Street, imposed financial accountability on a company that had been spending freely on moonshots, and the result was a stock that went on a run investors still talk about. Altman is a visionary. That's the easy part to see. What I'm watching is whether Friar and Simo get the room to do what Porat did not slow things down, but make the ambition legible and sustainable beyond one person's force of will. One more thing worth saying: ChatGPT is the most recognized AI brand in the world. That's a real asset. But consumer brand recognition and enterprise credibility are not the same thing. A hospital's procurement team, a bank's security committee, a government agency signing a multiyear contract , they're not buying based on name recognition. They need predictability, security, and someone to call when something goes wrong. Amazon understood the difference between what consumers see and what enterprise buyers need. OpenAI still has work to do on that front. The talent is there. The question is whether the structure lets it do its job. Wrote this post on my blog https://t.co/oG1wTph2MQ #OpenAI #EnterpriseTech #AIStrategy #TechLeadership #ArtificialIntelligence #CFO #SarahFriar #SamAltman

Acquire Competitors with SBA 7(a) for Cash Flow
The competitor acquisition is the one most existing business owners sleep on. SBA 7(a) covers it. You eliminate the competition and add cash flow at the same time. One of the cleanest deal theses we close. More operators should be looking at...
AI Unicorns Poised for $2 Trillion Valuations
What are my current valuation predictions for OpenAI and Anthropic? OpenAI was valued at $28B in April 2023. Its latest funding round puts it at $852B. Anthropic was valued at $4B in early 2023. Today, it’s worth $380B. In my...

Rising Private Credit Redemptions Signal Potential Trouble
My latest memo on the private credit market: Redemptions Are Climbing — Is That a Problem? https://t.co/QbeBHZNKir https://t.co/0CaMneVvAU
Fiat Money Can't Fill Oil Supply Gap
Since questions about private credit are so popular today, I had a segment with Danny about the topic:

Profitability Drives SaaS Premium Multiples Over Growth
SaaS valuations aren’t random — they cluster around growth + profitability Forward EV/Gross Profit vs NTM growth shows: • Higher growth → higher multiples (expected) • But operating margin is the real filter • Profitable names (green) consistently trade at premium $NET — 48x EV/GP...
Bigger IPOs, Bigger Whims: Underwriters Face Rock‑Star Demands
IPO company demands of their underwriters always remind me of rock star requests for Fiji Water and bowls of green M&Ms. The bigger the deal, the more outlandish and self-serving the demands.
OpenAI's TBPN Acquisition Rooted in 1902 Anti‑capitalist Precedent
If you are wondering why @openai bought @tbpn, then you have to go back to 1902 to get an answer, from an unlikely and the least capitalistic of sources. My short and sweet column from last evening (tip @techmeme). https://t.co/OUAfFSYMS6
Buy McCormick to Capture M&A Premium Amid Consumer
Q1 saw rare consumer megadeals as firms seek scale to counter slowing growth, tariffs and shifting tastes. Risks: integration and regulatory hurdles. Trade insight: buy McCormick for M&A premium capture. — Viktor Kopylov, PhD, CFA More insights: t.me/si14Kopylov
OpenAI and Anthropic Defy Trend, Pursue IPO
We know that OpenAI and Anthropic want to go public. The question is why, in an age of "stay private longer" https://t.co/6SiRk8bCTb

AI Secures $211B in 2025, Half of Global VC
ICYMI: The HumanX & Crunchbase AI Funding Report is out. In 2025, AI companies raised $211B, nearly half of global VC. See where capital is flowing now, & which companies presenting at HumanX may be poised for funding, acquisitions, or...
Inside the Real Work of Investment Bankers Daily
NEW ODD LOTS: This is what investment bankers actually do all day. @tracyalloway and I talk to Scott Bok, former longtime CEO of Greenhill & Co, to understand better what the industry does and why companies pay up for their services https://t.co/bLORIQJ8Oq

Analyzing the Sysco‑Restaurant Depot Deal on Deeper Dive
I joined @jonathanmaze on his "Deeper Dive" podcast earlier this week to discuss the Sysco/Restaurant Depot deal. #restaurant #distribution #Sysco $SYY https://t.co/aJyWwsj04T
Trust Is the Only Question Clients Really Ask
19 written questions. That's what a client brought to our meeting. But they were all asking the same thing: Can I trust you? Here's what that revealed about financial advisory.
Q1 2026 Dim Sum Issuance Rises 14% to 400bn Yuan
Caixin: "For the first quarter of 2026, dim sum issuance totaled nearly 400 billion yuan, up 14% from a year earlier." https://t.co/yksX2koWPr
OpenAI, SpaceX Deals Echo Localized ZIRP Phenomenon
OpenAI buying a podcast for a few hundred million and SpaceX IPOing for a $2 trillion feels like a wierdly localized form of ZIRP. https://www.wired.com/story/openai-acquires-tbpn-buys-positive-news-coverage/

SpaceX's IPO Valuation Skyrockets at Astronomical Multiples
SpaceX trying to go public at 80x forward sales, 500x forward earnings, and 125x forward EV/EBITDA multiple https://t.co/rk6SKuODJy

Space Stocks Rally Ahead of Anticipated SpaceX IPO
Space sector seems to be heating up in anticipation of SpaceX IPO. Buy the rumor sell the news? https://t.co/sbYe78s3xY

Predictive AI Nailed 731 Deals, Beating the Market
Crunchbase called it. In March, our predictive intelligence confirmed 731 predictions. We flagged Granola’s $125M round months early and RIVR as an acquisition target before Amazon made it happen. Not guesswork. Powerful predictions that give you an edge. 🔮 https://t.co/ykNPWspQ8D

OCIC Redemption Spike Covered by Quarterly Tender Liquidity
Blue Owl's non traded BDC, OCIC, received redemption requests for 21.9% of the fund. Is it cooked? No, it'll be fine. Here's why: 1) Portfolio turnover and 5% quarterly tender - OCIC tenders for 5% of its fund each quarter (20% per annum),...
Essential First Steps Before Buying a Business
LIVE - Buying a Business? What You NEED to Know First with Chris Papin https://t.co/2ry1qMoroe

Medallia Loan Collapse Erases $5.1B Equity, Media Silent
Medallia loan value continues to decline, with latest marks at 69. With the term loan in distress, the $5.1 billion of equity has certainly been vaporized. This -100% private equity loss surpasses any private credit loss by an order of magnitude. Where's...

Deep Discounts Drive High Redemption Tenders in Blue Owl Funds
Blue Owl Credit Income (OCIC) with 21.9% tendering for redemption and Blue Owl Technology Income (OTIC) with 40.7% tendering for redemption makes sense as both have publicly-traded "sister" funds that trade at large discounts to NAV: Blue Owl Capital $OBDC trades...
600
She dropped a 600-word equity research note in 2007. It erased $369B in market cap, ousted a CEO, and made her a Wall Street legend.
UK Gilts Mirror Trump’s Spoof: Market Holds the Power
Gilts are to the sitting UK government what Spoos is to Trump; the game will continue until either market says no more.
OTH Acquires Bellhart, Expands Hubs to Cut Costs
Macro: coastal marine services consolidate. Key: OTH buys Bellhart, adds 3 NC hubs to cut third‑party costs. Risk: low margins, approvals. Trade: buy OTH on weakness. 🚤 — Viktor Kopylov, PhD, CFA. More insights: t.me/si14Kopylov

Oracle Data Center Debt Costs Surge to High‑Yield Levels
Wow, borrowing costs on Oracle data center projects have widened to as high as S+450 $ORCL is IG. The data centers being built for Oracle are pricing like high yield.
Nexchip Seeks Hong Kong IPO to Boost Chip Output
China’s No 3 foundry Nexchip files for Hong Kong listing to scale output Wave of Chinese tech listings builds in Hong Kong as semiconductor groups plan expansion to meet domestic demand... https://t.co/rcA6r9CkE2 via @scmpnews
Amazon Targets Globalstar Amid Apple Stake Complications
Macro: LEO consolidation accelerates as Amazon eyes Globalstar (GSAT +12%). Key: Apple’s 20% stake complicates talks; SpaceX competitive pressure. Risk: deal uncertainty, regulatory review. Trade: buy on confirmed deal. — Viktor Kopylov, PhD, CFA More insights: t.me/si14Kopylov

Amazon Eyes Globalstar Acquisition; 2028 Target Alerts Triggered
Wow, $AMZN in talks to buy $GSAT Been solid one all year, Jan 2028 calls hit my alerts 3/31 https://t.co/OvcOV5QTT1
Master the Game, Not the Grind: $200M Exit
my friend owned one radiology clinic then he acquired 23 more structured correctly zero personal capital exited the platform for $200M he didn't work harder he learned a different game

SpaceX IPO Could Valuate Firm Above $1.75T
Thoguhts? We discuss the historic announcement of SpaceX's IPO, which could raise 40 to 80 billion dollars and value the company at over 1.75 trillion. We explore how this would make SpaceX one of the top seven most valuable companies...

Figma's IPO: Record Pop, Then Record Plunge
Figma holds two stock price records: 1. Biggest "IPO pop" of major IPOs (or any SaaS company) since 1999 2. Largest subsequent loss from the IPO pop after 6 months (see thread) https://t.co/Z7h6AnLHkI

SpaceX Preps IPO with Analyst Day, Data Center Tour
SpaceX is said to plan analyst day, data center tour amid IPO preparations @seekingalpha @wallsthorizon @christinelshort https://t.co/dgH1iq69mo

Private Credit Defense, IPO Rush, Misfortune as Content
🆓 Wednesday links: defending private credit, the rush to IPO, and turning misfortune into content. https://t.co/FjF6EvQcdR image: https://t.co/JLHc6phWc7 https://t.co/NpoUqeZdSW
Banks Play IPO Auditions as OpenAI Valuation Soars
"Don Corleone, I am honored and grateful that you have invited me to your daughter's wedding. And I pledge my ever-ending loyalty." — Luca Brasi The big story beneath the story of OpenAI's $122 billion at an $852 billion valuation is...
SpaceX IPO Defies $1B Revenue Ceiling, Aims Massive Scale
Pretty momentous day when SpaceX files for possibly the largest IPO ever. I remember when VC colleagues used to say this company had stalled at $1B or so of revenues, and that a space taxi company could only be *this* big,...

Acquire Smartly, Scale Fast: Boost Valuation Through Strategic Buying
In this episode, Jeremy breaks down the art of buying versus starting from scratch, teaching you how to identify the right businesses to acquire, mitigate risks, and exponentially increase your valuation through strategic scale and financial engineering. Tune in now: 📺 :...
Buy More SpaceX Shares As Valuation Drops
SpaceX IPO likely in June. Here is how I'm thinking about participation: 1)priced at $1.75T i'll buy zero shares 2)priced at $1.5T i'll buy 25% position 3)priced at $1.25T i'll buy 50% postion 4)priced at $1T i'll buy a full position

SpaceX Files Confidential IPO, Targeting June Listing
JUST IN: Elon Musk owned SpaceX has confidentially filed to go public through an IPO SpaceX submitted its draft IPO registration to the 🇺🇸 SEC. The filing puts it on track for a June listing
SpaceX Rumored to Acquire Globalstar at SatShow 2026
"Rumors that SpaceX will buy GlobalStar were the buzz at SatShow 2026 last week." https://t.co/YuUnHqkpoE “I think everyone’s convinced that there will be a sale of Globalstar,” @TMFAssociates , founder of the satellite research firm TMF Associates, told @malleven33

Crocs Paid Half Its Market Cap for Tiny HeyDude Sales
Last year, the Crocs brand sold ~129 million pairs of shoes - or nearly 6x greater than the ~22 million pairs that were sold under the HeyDude brand. In early 2022, Crocs paid ~$2.5 billion for HeyDude. The company's market cap is...

Founder Keeps 49% of $1B Exit via Smart Build, Funding
Julian Hearn just sold Huel to Danone for €1bn. he walked away with £420m personally. that is 49% of the exit. most DTC founders who raise that much end up with 15%. two things made the difference: how he built the business, and...
Remote Teams Can Depress Startup Acquisition Valuations
One impact of remote or partially remote teams - lower purchase price if startup goes for a smaller exit / M&A (or in some cases acquisition doesnt happen at all) Reason: fewer buyers want fully remote teams, or teams w key...
Cruz, Ruddy, Gomez Slam $6.7B Nexstar‑Tegna Merger
And @tedcruz & @ChrisRuddyNMX & @AGomezFCC have a problem with the @NXSTMediaGroup - @TEGNA merger at $6.7 billion. #pathetic
OpenAI's $122B Funding Lasts only 18 Months
JUST IN: OpenAI's $122,000,000,000.00 raise will cover operations for just 18 months before they need more funding.
SpaceX Assembles 21-Bank Syndicate for Massive IPO
JUST IN: SpaceX formed a 21-bank syndicate to handle its IPO, marking one of the largest private-to-public tech listings in years according to Reuters.
Record‑Breaking $10B+ Megadeals Kick Off Year
Megadeals are keeping the bankers and lawyers busy on Wall Street. It’s been the best start to the year ever for transactions valued at $10 billion or more. https://t.co/99uezBcTRB
Build a Deal Flow Engine for Successful Acquisitions
When acquiring a business, building a deal flow engine is key. Here are three things I've learned about building a deal flow engine:
OpenAI Secures $122B, Sets Record Funding Round
OpenAI completed the largest funding round in Silicon Valley history, raising $122 billion ahead of a blockbuster IPO expected by the end of the year https://t.co/jq6mF0qHvN via @WSJ