So per Forbes for the first time there are over 3,000 Billionaires in the world.  Tech is heavy on the list, and #1 is Elon Musk. When I started in SaaS, it was tough to imagine many B2B billionaires, as most SaaS companies were lucky to IPO at a $1 Billion valuation.  So founders might...
Continue Reading

Dear SaaStr: One of Our Most Respected Team Members Quit and Folks Are Leaving. What Do I Do? Promote someone great that everyone respects into a leadership role.  Right now. This is really the only answer I’ve seen to this situation. We’ve all been in it at least to some extent, at some level. Sometimes,...
Continue Reading

So Harry Stebbings kicked off a new Live 20VC format: “The Daily Deal” and I was lucky enough to serve as co-host!   We did a great live deep dive, together with the CEOs of Moveworks (just acquired by SeviceNow for $2.8 Billion!) and Cerebvs (AI chips about to IPO): – Why B2B Revenue is...
Continue Reading

So if you are incredibly good at VC, you can make a lot of money.  More on the math here.  If you own 20% of a Decacorn ($10B), then the fund makes $2 Billion, and the partners typically keep 20% of that, or $400m.  And split it up.  The math isn’t quite that simple (at...
Continue Reading

Dear SaaStr: What Are Simple Hacks that Salespeople Use to Confuse Customers? Well I’m not sure confusing customers so that they buy works, but the one tactic that does is FUD. Fear, Uncertainty and Doubt It’s the process of finding weakness in your competitors, and exaggerating and maybe even a few lies about them to...
Continue Reading

So Freshworks started off as a low-end Zendesk competitor (Freshdesk), but relatively early expanded into a broader suite of related products for service and support, and most of its growth today is fueled by its lower-end competitor to ServiceNow, it’s “EX” products.  As you can see below, it went aggressively multiproduct by Year 4: The...
Continue Reading

Dear SaaStr: How Long Should You Give a New Sales Rep? The tough truth is from 0.5–1.5 sales cycles. Sales is tough. It’s a lot of Nos to get to a Yes. And while sales is pretty similar in SaaS at a given price point / ACV, different products are still different to sell. A rep...
Continue Reading

No one has a true crystal ball when it comes to Cloud spend in the coming years, but the leaders have a lot of data.  Thoma Bravo is one of them.  It’s the #1 Private Equity firm for B2B and SaaS companies and it surveyed 501 Cloud and SaaS buyers. Here’s what it found: Software...
Continue Reading

Sam Blond and Jason Lemkin joined together for a live SaaStr Workshop Wednesday looking at what has and what hasn’t changed in 2025 in GTM in general and in the age of AI. They did a deep dive looking at top learnings not just from their own ecosystems, but from the top CROs Sam has...
Continue Reading

Dear SaaStr: What Are The Top 5 Mistakes Founders Make With Their VC Investors? In rough order: #1. Hiding Important Things. VCs are wired to take bad news. But not for it to be thrown at them at the last minute: If Times Are Tough — Don’t Hide. Be Present. #2. Not Knowing the Zero...
Continue Reading