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Software’s Top Winners and Losers
How has public software companies performed since peak 2021? How have IPOs performed?
Jun 20
47
6
3
From Unicorn to Zombiecorn to a $3.6B Acquisition
How Intercom went from a ~3x ARR multiple to a 36x ARR multiple
Jun 16
27
2
How I Cut Our AI Spend in Half | "Tokenmaxxing" is Dead
6 ways to cut your AI spend without cutting AI usage. Every CFO needs to understand these.
Jun 9
49
4
4
The "ARR" Guide for an AI World
What even is ARR in 2026? There is lots of ARR fraud/deception out there...
Jun 4
37
2
2
May 2026
Entrata S-1 | An Actual Software IPO?!
How do Entrata's financials stack up, and will it pave the way for more software IPOs?
May 31
42
2
Where AI Costs Belong on the P&L
AI token spend will soon be the largest vendor expense for most companies, and many of you are accounting for it wrong...
May 26
45
5
2
Deel's "Accelerate or Die" Moment
Accelerating in the age of AI + My discussion with their CFO on how they win
May 19
29
1
How I Built AI Agents to Close the Books
What I built to shave 1 day off our already fast close…
May 15
48
7
4
Anthropic's Warning to "Investors" | Your Shares Don't Exist
Fraud, grey areas, and investors who don't understand standard equity agreements. So what actually happens to all these Anthropic "investors"?
May 13
50
3
4
It's a Buyer's Market | And A Seller's Nightmare
My playbook for getting the best deals I have ever gotten in my career. The AI threat has made buyers scarily powerful...
May 8
40
3
2
Is My Team AI-Pilled?
The 5 levels of AI adoption and why a lot of AI advice is bad
May 6
56
3
3
Thoma Bravo's $5B Medallia Loss | The PE Reckoning is Coming...
Inside how Medallia broke and what it means for the rest of software
May 1
71
5
6
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