Recently, I met with a good friend running a SaaS company doing about $4 million in ARR. A really good SaaS company. And he was beside himself.
First, he was just plain exhausted. He was in that zone from $1 to $10m in ARR when it all just gets so hard. Too much to do with too few people. We talked about how The Cavalry Was Coming. That the operational part would get harder before it got easier … but it would get easier once he doubled or so, when he’d finally have some redundancy and fat on the team and the model. (More on that here).
Second, he was almost overwhelmed with The Competition. “They’re in every deal now,” he told me. “And they have five times the headcount and have raised $25 million. They’re all over us.”
I asked how much would he…
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