“Cynicism is the coward’s way out.”
Jason Calacanis
Last week, I thought, “Wouldn’t it be awesome to be on This Week in Startups some day? Maybe many years from now.”
A couple days later, it happened!
Jamming with JCal
Host and angel investor Jason Calacanis was doing a Q&A session with some rabid fans. I asked Jason something I’ve been struggling with for a while.
What’s the right balance between skepticism and enthusiasm when you look at a startup?
Jason’s answer surprised me.
“It’s really easy to be cynical. And what you wanna focus on is not all the things that could go wrong, it’s what could go right.”
JCal
I expected him to say you need X amount of enthusiasm and Y amount of skepticism. But instead, he basically said the skepticism takes care of itself.
It’s the enthusiasm that’s harder — and more important!
Looking back on my meetings with founders, Jason’s comments make a lot of sense. Pick any startup, and you could find 100 problems with it.
But the question is, if everything goes right, is it another Uber? Another Google?
If so, I want to make that bet.
“The Vision Thing”
I also love what Jason said about understanding the founder’s vision.
“One of the things we’ve added to our script…when I’m training my young associates and researchers how to interact with founders is just to say at the end of the conversation, ‘Hey, can I repeat your vision back to you to make sure I understand your vision.’”
JCal
I’ve already started using that in my meetings. I’ve forgotten a time or too, but I’m going to work on this!
Figuring out the founder’s vision is a great way to show respect. And if I do it right, I will truly understand the opportunity before me.
It would be a darn shame to miss Uber because I don’t understand what Travis is doing.
Building a Better Investment Process
Jason and I also talked about how to build a better process for making investments.
“In any discipline you get into, I think you eventually will start to look at systems and processes and really try to optimize those.”
JCal
We can’t control what happens after we make an investment. But we can control our process for finding startups and making those bets. What’s more, we can adapt the process to play to our strengths.
Jason is more extroverted than just about anyone. He loves doing as many meetings and podcasts as he can.
I like meeting founders too, but I’m not quite as much of a people person as Jason. I mean, who is? 🙂
But when I’m reading a deal memo, I’m really in my element.
It occurs to me that the company pages at YC are essentially deal memos. I can just read tons of them and contact the startups that interest me most. That’d be one great way to play to my strengths.
Wrap-Up
Since we had this conversation on Tuesday, Jason’s words have been on my mind.
I’ve tried to look at these little companies and imagine them as giants many years from now. And here I am on day one, meeting them when they’re still raw and full of potential.
Pretty great job, isn’t it? 😊
What do you think of our little Q&A session? Leave a comment and let me know!
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