
Why Misunderstanding Startup Metrics Can Cost You Your Business
There has been a lot of public debate over the past several weeks about whether it’s a good thing to be “gross margin positive” or not and commentary always reminds me that some people at startups don’t quite understand financial metrics or even how to think about which ones are healthy. When I publicly Tweeted […]

The Top 8 Mistakes I Made In My First 18 Months As a VC Partner
So I’ve been investing “institutionally” as a VC for about 18 months now (maybe really only 12, counting from the first check that really mattered). A little bit before that as an angel, but not that much. ‘Cause I sort of needed to decompress for a little while after I sold my last company. At first, […]

Why Taking Some Risks in the Sales Process Can Improve Results
Many people are too cautious in sales processes and as a result when they present their solutions they end up sounding milquetoast and undifferentiated from anybody else in the market. In this post I advocate taking a harder stand on where your product or solution differentiates in the market – even if it means you […]

“My CEO Told Me To Stop Selling So Much”
Recently, I met with a sales leader I’ve known for years, and he told me The Most Curious Story. His SaaS CEO asked him to stop selling so much. Slow down. You are doing too good of a job, the CEO said. We can’t afford it. Now … how could this be? Well, it does […]

Gadi Shamia, COO of Talkdesk: “8 Things I Learned After Joining a Hyper-Growth SaaS Startup”
One of the things I want to do between the ’15 SaaStr Annual, the SaaStr blog, and the ’16 Annual is do true, longitudinal, hands-on SaaS case studies. Not just one-and-done podcasts, posts, and the like. But to go further, to check in repeatedly with (x) very successful, (y) soon-to-be very successful, and (z) pre-successful SaaS […]

I Hired My VP of Marketing at $20k MRR. It Wasn’t a Week Too Early.
One of the starkest differences I see between First Timers in SaaS and Second Timers is when they hire their VP of Marketing. At BoxDev the other week (our post here), the contrast was especially vivid. Second-timer Shan Sinha, now CEO of Highfive hired his first head of marketing a year before first revenue. A […]

Help Us Pick 1 or 2 of the SaaStr Annual ’16 Speakers!
We’ll start to roll out the SaaStr Annual ’16 speakers in the coming weeks. It will be tough to top the ’15 speakers — from Aaron Levie to Bob Tinker, from Stewart Butterfield to David Sacks, from David Ulevitch to Parker Conrad, etc. etc. But we will find a way! We’ll also have three full […]

Your VP Sales Has a Sales Quota. Your VP Marketing Needs a Lead Quota. Period.
A ways back, we did an extremely popular post entitled, Hire the Right Type of VP Marketing or You’ll Just End Up With a Bunch of Blue Pens with Your Logo On Them. The basic idea was to help folks who haven’t hired a VP or Director of Marketing hire the right one for a […]

5 Tips To Make The Journey More Fun
Really, there’s nothing I’ve done in my life that is harder than being a founder CEO. Nothing. It’s 100x harder than being a VP. Even if the actual work is easier. It’s 100x harder than being a VC. Even if delivering top returns as a VC is maybe even harder than as a founder. But I […]

It’s time to reconsider, Google
Almost a year ago, Google made an apparently small change to Google Calendar. They started automatically adding Google Hangout video links to every new appointment. And it was bad. I’m sure you’ve all seen appointments like this pop up in your calendar. How do you join the meeting? Do you dial the phone number, or […]

SaaStr Podcast on Time, Core Metrics and More on “Million Dollar Insights”
Do you podcast? If so, Cara Hogan of InsightSquared has kicked off a great SaaS podcast series of which I was fortune enough to participate. We talked quite a bit about the learnings on the SaaS Journey. Feel free to listen below or download on iTunes here. The draft notes and script I used (we went […]

5 Tips to Grow 10-20% Faster Than Plan in ’15
It’s time to do a series of posts on SaaSt to sort of … kick your arse a bit. What I mean by that, is that no matter how well you are doing post-Initial Traction in SaaS … you can almost always do at least 10-15% better. Pretty much almost always. Because there’s almost always more […]
If You’re Going to Do a SaaS Start-Up … You Have to Give it 24 Months
It seems like everyone wants to be a SaaS founder these days. I meet with great VPs of Sales and Product in particular who are Ready. It’s time. To go out on their own. Start their own SaaS company. Awesome. I get it. I’d like to recruit you to be a VP at one of […]

One Weird Trick to Build a Personal Brand
My long-time friend Jason Lemkin is on the verge of launching a spectacular SaaS conference called SaaStr this week. What Jason has achieved in no time flat in VC is astounding. Without inventing the browser he has single-handedly created a personal VC brand on a shoestring. And as I’ve written about before – building a […]

The Low Viral Coefficient of SaaS, And Why That’s Just Fine
We’ve talked a lot on SaaStr about how to get from $1m to $10m, $2m to $5m, $10m to $30m, etc. etc. One area we haven’t talked as much about is getting from say $100k in ARR to Initial Traction, or $1-$2m in ARR. A bit, but not as much. The reason is while I […]