
Josh Stein, Partner @ DFJ: What Makes a Great SaaS CEO (Video + Transcript)
As a partner at Draper Fisher Jurvetson, Josh Stein has invested in some of the most well-known SaaS companies in the world like Box and Yammer and spent plenty of time with truly remarkable SaaS CEOs. In this session he and Jason Lemkin sit down and dive into what really makes a great CEO, and how that […]

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 […]

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, […]

At $50k in MRR, Running Out of Money Is No Longer an Excuse
We’ve talked a lot about SaaStr on the challenges in getting from nothing to that first $1m-$1.5m in ARR, “Initial Traction”. That is takes longer than you think. That if you get 10 customers, you can get another 10, 100, and so on. There’s a particular moment in time I want to focus on here […]