Don’t Fire Your “Worst” Customers. Hire Them a Psychiatrist Instead.
There’s a lot of Internet advice that makes a lot of sense, but not necessarily in SaaS. Somewhat bad advice that entrepreneurs share again and again, without having really tested the ideas behind that advice. One bit of advice you hear again and again, that I 93% disagree with, is “Fire The Customers That Don’t […]

The Authoritative Guide to Prorata Rights
Prorata rights are one of the most important rights of a private market technology investors and yet are seldom fully understood. They often create the biggest tensions between investors who are investing at different stages in the business. These tensions seep out in some angels or seed funds publicly or semi-privately deriding later-stage VCs for […]
Planning to Do a SaaS Startup? Don’t Forget the 20 Interview Rule.
Recently I spent some time with two seemingly similar SaaS start-ups. Both are at about $100k in MRR (congratulations!). Both have happy, enthusiastic customers. Both have really great products and are organically growing. Both have great founder CEOs. But even though both are now at $1m ARR … one is just so much better positioned […]
Come to the SaaStr Sessions at Dreamforce — And Win a Free Ticket to the SaaStr Annual in February (And Other Good Stuff)
We’ve got 2 great SaaStr sessions at Dreamforce on Wednesday, October 15 at 1pm and 3pm. Each has about 15 seats left so add them to your Dreamforce event planner now! To make it (even more) fun, we’ll give away 2 free tickets to the SaaStr Annual on Feb 5, 2015 in San Francisco (details […]

What is the Definition of a Seed Round or an A Round?
Marc Andreessen kicked off another great debate on Twitter last night, one that I’ve been talking about incessantly in private circles for the past 2-3 years – what actually IS the definition of a seed vs. A-round. This is something I think entrepreneurs don’t totally understand and it’s worthwhile they do. My view: “Spending […]
I Never Lost a Customer I Actually Visited
There’s a lot to talk about in customer success about churn, and about upsells. Together, they are one of the most critical topics in recurring revenue business models. To all that, I wanted to add one very tactical insight: of the 1000s of customers we closed when I was running EchoSign … while we lost a few […]

Three Words Entrepreneurs (and VC’s) Should Take to Heart
Note: this is a non-religious post. This weekend was Yom Kippur, holiest of the Jewish holidays and the day of atonement. It’s also the day when most Jewish minds are least focused since one needs to fast for 24 hours. I sat in schul listening to the rabbi’s sermon and given my mind is prone […]

What is the Right Burn Rate at a Startup Company?
I was reading Danielle Morrill’s blog post on whether one’s “Startup Burn Rate is Normal.” I highly recommend reading it. I love how transparently Danielle lives her startup (& encourages other to join in) because it provides much needed transparency to other startups. Danielle goes through some commentary from Bill Gurley, Fred Wilson and Marc […]
What to Do If Your Business Decelerates
A little while back, I did what turned out to be a very popular piece: If You Do Sell [Your Company] — Do it a Local Maximum. A wise friend of mine commented on it afterwards. “You’re absolutely right. Selling your company at a non-local maximum is incredibly frustrating. But you know what’s 100x […]
Come See 3 Epic Sessions at Dreamforce on Predictable Revenue, Benchmarking, and “The Best of SaaStr”
Salesforce has put together another pretty epic founder / entrepreneur track this year at Dreamforce. You can check out the schedule here. There are three sessions I wanted to highlight in particular, that I’ll either be at or leading. First, on Day One, Monday October 13 at 1:30pm, Aaron Ross, my good friend, colleague and […]

Why Recruiting Isn’t Over When an Employee Accepts Your Offer
Recruiting. It is the bane of every startups existence because it takes up so much time, it is so competitive to sign people and it feels like unproductive time because it’s not moving the ball forward on product, engineering, sales, marketing, biz dev, fund raising. It consumes time and energy and the payoff doesn’t come […]

When VCs Play Defense
Somehow the world seems to be spinning faster these days than just a few years ago. The frantic pace of technology cycles, the amount of tech news, the blogs, the conferences, the demo days, the announcements, the fundings, the IPOs. It’s exhausting. Perhaps unsustainable. It got me thinking about the advice that I often give […]

Bad Notes on Venture Capital
This week. On the phone … Me: So, you raised venture capital? Him: Yeah. We raised a seed round. About $1 million. Me: At what price? Him: It wasn’t priced. We raised a convertible note. Me: With a cap? Him: Yes, $8 million. Me: Ah. I see. So you did raise with a price. It’s […]
Money, Bonuses, “Customers That Waste My Time”, and Greed: You Get What You Pay For
There was one thing prospective sales reps would say in an interview that always chilled my spine. It would especially come from sales reps from larger companies in high-velocity in-bound environment (e.g., WebEx-type environments). They’d say this: “Those type of leads just Wasted My Time.” Sigh. Yes, I guess it’s technically true. If you’re a […]

Why We’re Looking to Fund Stuff With More Meaning
Venture Capital is a tricky industry. If you’re funding the same stuff as everybody else and if you started your activities when the clues were obvious you’re much less likely to drive enormous returns. When Fred Wilson funded Twitter I guarantee you it wasn’t obvious that it was a billion dollar+++ idea. Far from it. […]