
Adapting to the Great Reset
You would have to be hiding under a rock to have missed the shift in private tech investor sentiment that has become apparent over the past several weeks. Truth is, this shift has been underway for some time. The final stage – when the change in psychology fully reveals itself in the popular tech media – always arrives […]

All These Enterprise IPOs: Why It’s Just Getting Good. Why These are The Best of Times for SaaS.
Reading the tech press you might get the sense that The Enterprise is something they are sort of forced to write about because it’s having a good run. We had a great Consumer run, a nice set of Multi-Billion Dollar deals around Social Networking, a WhatsApp/Snapchat fad around mobile messaging, an Alibaba, Instacart, Fab-ulous e-commerce […]
SaaStr on NBC’s Press:Here on Box, DropBox, WhatsApp — And the Lack of Fear
NBC was kind enough to have us back on Press:Here (right after Meet-the-Press) to discuss DropBox’s almost-$1-billion in debt and equity raised this year, Box’s IPO, and beyond that, just what’s Going On in the Enterprise these days. My overall answer: there’s current a Lack of Fear, notwithstanding the (relatively modest) market correction in ’14. […]
The Simple Reason Why There Will be 10-20 Great CRM IPOs in the Next Few Years
I wrote a while back about Room at The Bottom, and how once a space gets big enough (~$100m) or so … the biggest guys end up abandoning many of the smallest customers and segments in their space. Which once a space is at, say $100m in market size, can open up a $10m hole […]

Why You’ll Want to Raise $100,000,000 for Your SaaS Start-Up: The Incremental Customer
With all the SaaS companies raising big, later-stage rounds these days you may wonder … why? I mean, just because you can raise $100m or whatever epic number … should you? Today, I think the answer is yes. Though perhaps not for the reasons you might think. There are a couple of standard reasons companies […]
The 10x Rule: What Raising $1 of Venture Capital Really Means
Recently, a good friend of mine asked me how much he should raise in his round. He was lucky enough to have a range of options. My simple advice was: assume you have to return a liquidity event (sale or IPO) of at least 10x the amount you raise. Valuations change from round to round. […]
The Pernicious Effect of Dilution in SaaS: The Cold, Hard, Bloody numbers
And there was my first real-world lesson in dilution. One founder. A decade of dedication. IPO. Yet just a percent or two in ownership. Not enough to even “make the table”.

A Real Life SaaS Case Study: Eloqua. Marketo. Pardot. There Are 3 Different Paths to Success, My Young Padwan.
I don’t know about you, but I really can’t stand case studies. They always seem either contrived (forcing contrasts in companies that aren’t really there) or else too hypothetical, because we know which way things really worked out in real life (Case Study: Company A had to decide whether to do action X or Y. […]
Workday is Growing 90% this Year. At $250m in ARR. So Wake Up: You Probably Need to Do A Lot, Lot Better.
The thing is, what you really have to ask yourself, if you are growing less than 100-150% YoY — all the way to $100m in ARR — is the market just too small? Or if not — am I just not well enough positioned in the market?
It Takes at Least 7 Years in SaaS: Can You Do The Time?
I was recently at a dinner with a founder of a pretty successful web company, and he asked how long I had worked on EchoSign, and he nodded his head, and he said “Yeah same for me. It takes about 7 years”. People know SaaS takes longer than consumer web to scale. But it’s not […]
The Workday IPO and ‘F You Money
The other day, a VC asked me about a founder he was thinking of investing in. He asked me if this founder had, quote, ‘F You Money. {I learned how this was spelled when a Businessweek article this week used the term, btw}. I wasn’t really sure if he meant this as a negative, but […]

Facebook, Part Deux
Nearly two years ago, I asked the question, “Did Peter Thiel Make The Single Best Investment In History?” Today, now that Thiel has sold most of his remaining stake in Facebook, it’s a good time to re-examine the math surrounding his investment. Two years ago, I wrote: In 2005, Peter Thiel paid $500,000 for a […]

NASDAQ CEO blames CIO over Facebook IPO
NASDAQ CEO, Robert Greifeld, blames staffers and IT for the Facebook IPO debacle. Where was his own accountability?

VC 2006-11: $136 Billion In, $146 Billion Out
There’s a lot of talk recently about a Kaufmann Foundation report on the venture capital industry that states: Over the past decade, public stock markets have outperformed the average venture capital fund and for 15 years, VC funds have failed to return to investors the significant amounts of cash invested, despite high-profile successes, including Google, […]

Wanted dead or alive: any Facebook user, $ 125 reward
With the upcoming IPO of Facebook this week, I got a little worried. I told a few people “Mark my words, this IPO is going to blow the Social Media bubble once and for all” and even “Wouldn’t be surprised if FB’s IPO is going to start the final leg of this crisis and finish […]