When to Stop Doing It All Yourself
Perhaps the biggest difference between most first-time founders and most second-time founders is how long they try to do it all themselves. This isn’t a criticism first time you usually sort of have to. You have less capital to hire a team, and less experience building teams. But then after that there are at least […]
One Simple Rule on When to Build a “Custom” Feature
“Custom” features … I feel this is perhaps the point founders get the worst advice of all. Especially from VCs, B2C folks, and folks that have never sold bigger deals and into the enterprise. One-off customization per se is bad. This is SaaS, not a services business. But Being paid a lot to build something […]
The Two Things to Do. When You Don’t Know What to Do.
There may come a time, or two, in your company when you just don’t know what to do. You aren’t growing fast enough. or The competition seems to be getting the best of you. or You can’t raise financing. or You just lost an important deal. Or maybe more than one. or That great new […]
One Tough (But Rewarding) Job: Being the First Sales Rep at a SaaS Startup
Ah, the first sales rep. Being the first salesperson into a start-up in a rewarding — but very tough job: Your Founder Boss likely will never have managed a salesperson before. She likely won’t know what you are supposed to do 40+ hours a week. Your Founder Boss may have strong views on what you […]
Last Minute Tips & Tricks for The SaaStr Annual!
It’s almost here. The 2017 SaaStr Annual. Just a few extra last minute tips: It Will Be Packed. We’ll have ~10,000 nominal attendees which realistically means about 5,000 on-site at any given time at the Bill Graham (not everyone will be there at all times, etc). The Bill Graham is a super fun venue, the […]
Why The Law of Large Numbers is Just an Excuse
Everyone has tough quarters, and usually, at least one tough year (more on that here). As we approach $10m, and then again as we approach $20m, and then again as we approach $X0m … we often blame a factor that I believe rarely is really real — The Law of Large Numbers. The Law of […]
The Top 10 Worst Pieces of SaaS Advice
Advice is very context sensitive, so take this post with a grain of salt. But for me, it’s “Blue Monday” … so I thought I’d take a stab at the Top 10 Pieces of Classic SaaS Advice … that in my experience at least are usually Just Plain Wrong. The advice and thinking that leads you […]
Time Doesn’t Kill All Deals. But It Puts Them At Risk.
There’s a little bit of death-by-a-hundred cuts that many SaaS companies box themselves into. As they scale, they get out of the hackey way they do contracts, NDAs, proposals, and other documents. They have their controller, then their VP of Finance, then their CFO review things, then hand off to the General Counsel. Which takes […]
My First Big Sales Deal
In my first start-up, I was mostly hunting whales — seven figure and eight figure deals. I had no experience doing any of this. For our First Big Customer, we’d been negotiating a $6m/year contract for quite some time (they always take time). We finally had the “all hands” meeting with all the C-level and […]
e-Staff Meetings and 1-on-1s: You Gotta Do Them
For the first time in my career, I’ve worked with amazing first-time managers as CEOs. Before I was a CEO, I was a mid-level manager, a director. And then a VP. Across a few start-ups. Before I was first a founder. Those management team weren’t perfect, and I wouldn’t copy everything they did. But at […]
4 Tips To Earn Respect as a Young CEO
While age ultimately doesn’t matter — results do — in SaaS, starting off as younger-than-average can create stress in a sales and customer-driven environment. But Aaron Levie started Box at 19, Mark Zuckerberg and Bill Gates dropped out at 19-ish, you know all this. Some some hacks: Start with SMBs. It’s easier to get taken seriously, […]
Why The LinkedIn Acquisition is So Important to SaaS
So, Microsoft bought LinkedIn for $25.6 billion dollars. That headline shocked all of us the other day. But if you step back, it’s not that impressive, the raw number itself. After all, as a public company, LinkedIn was worth $32 billion just a few months earlier, and had been on one heck of a run […]
The Easiest Ways to Get From $1M ARR to $10M ARR
The most important thing is not to chase the shiny penny, assuming you are growing at least 60% Year-over-Year. You’ve done the Impossible. You’ve gotten 50, 100, whatever # of businesses to pay you $1,000,000 a year. There are 10,000 new apps out there. It’s “impossible” to get to $1m. You did it. Now, the […]
How to Avoid Being Replaced as CEO by Your VCs
Worried about a bunch of VCs replacing you? You should be a little worried, probably. Just the other day, a CEO that I know fairly well was fired by a VC. Strange thing was, the VC didn’t talk to the rest of the board. Who didn’t agree. So he got un-fired. Awk. Ward. CEOs getting […]
The Difference Between Very, Very Good Founders. And Truly Great Founders.
I consider myself a “Magna Cum Laude Minus” founder. Nothing I’ve done has ever failed (although I’ve almost failed many times). I returned 5x to my investors — twice. Look, that’s pretty good. And I think I was a pretty good CEO. But not the very, very best. And I didn’t really know what […]
