The Two Mindsets That Can Kill Your Startup

**Dalton Caldwell** (0:00)
And you feel like you're strapped to this crazy person. You're like, oh no.
I'm like this, I'm in a car, and the driver of the car is completely insane, and it's going to take us all down. What have I done with my life?

**Michael Seibel** (0:19)
This is Michael Seibel with Dalton Caldwell. Today, we're going to talk about whether you are being too optimistic or too pessimistic about your startup.
Dalton, set this topic up. We certainly meet many founders who fall in either of these categories pretty regularly.

**Dalton Caldwell** (0:37)
Yeah. The fact is, you need to be both optimistic and pessimistic. If you're too far on either extreme, you are going to fail.
To start with, let's talk about the comical stereotype of someone that's too pessimistic, and we know these people. So paint me the picture, Michael. Who's the stereotypical too pessimistic founder? What are they like?

**Michael Seibel** (1:09)
It is like one painful experience causes them to want to either quit everything or change everything and fill in the blank on the painful experience. It's like bad customer call, bad investor pitch meeting, talk to a friend, whatever it is, talk to an advisor. But one negative experience is getting them to run away.

**Dalton Caldwell** (1:33)
Yeah, it's like Eeyore or something. I don't know if that's too weird of a reference, but woe is me.
Everything bad is happening to me. The world's out to get me.
Everything that could go wrong is going wrong, and everything's going to shit and they're screwed. Nothing good can happen to me. That is what talking to a too pessimistic founder is like. How about the comical stereotype of someone who's too optimistic? What's it like talking to them?

**Michael Seibel** (2:01)
So at first, you get really excited. You're like, there must be something here. But the longer they keep talking, the more you are extremely confused why it doesn't appear like anything has happened, like any value has been created or any insight has been found. And then at some point, you start asking questions because you're assumed that you're the idiot.
But by the end of the conversation, you are convinced the person actually has no idea what they're doing. That's never happened to us before, though. That's all theoretical.

**Dalton Caldwell** (2:34)
Yeah, it's like talking to someone that's had too much coffee or is medicated or something, where everything is great. Everything is wonderful. Everyone is out to help them. Like the planets are aligning.
Their startup is the best thing ever.
And then again, yeah, you ask questions, and you're like, wait, this sounds kind of bad. Aren't you concerned about some of this stuff? And they're like, no, no, this is all going according to plan. This is like, it's really good. And so again, at both extremes here, there are problems, okay?

**Michael Seibel** (3:09)
And not only that, they multiply when you have, God forbid you have employees, right? Like then it's even worse.

**Dalton Caldwell** (3:16)
I think it's helpful to do this self-diagnosis if you're too optimist, you're too pessimistic, to put yourself in the shoes of your employees and imagine who would you want to work for? Who would you think would be like a good leader? Because to answer this, I think a good leader is an optimist. They believe, if they don't believe, they're a horrible leader. Like right out of the gate, a pessimistic leader who doesn't believe that things can work, quit. Like that's a bad leader. So you're off the team, okay?
On the other hand, though, a too pessimistic, sorry, a too optimistic leader has horrible plans. Their plans involve magical things happening, rainbows and ponies and space time travel.
Like, if you listen, if you actually listen to the over optimistic person's plans, any reasonable employee would be like, wow, this person has lost their minds. They have no idea what's going on here.

**Michael Seibel** (4:15)
And it becomes a little scary when your leader sounds like that. Suddenly you're like, oh, God, are we even going to get the basics right when this person doesn't seem to be tethered to any landmass at all?

**Dalton Caldwell** (4:30)
The person said two months ago that our company was great and we were all going to be rich, and now they're saying the funding fell through, but they have a solution. Are we going to even make payroll?
You lose your credibility in two seconds.

**Michael Seibel** (4:45)
Yes. You make that perfect point. When you cross over being too optimist, your employees start questioning everything.
You lose all trust because they're like, oh crap, if the leader can't see this obvious thing right in front of their face, uh oh, what else have I not uncovered yet on what the leader can't see?