4 Lessons I’ve Learned Working For Jason Calacanis

I’ve been hesitant to write this because I don’t want ya’ll, the lovely readers of this blog post, to think I’m kissing my boss’s ass. 

But hell, why not. What I’m about to share are killer lessons from a damn good entrepreneur and investor.

So Jason, if you read this – I’m not kissing your ass with this blog post. 

Alright, on with this good stuff.

As you might know, I’m the CMO at Inside.com – a media company founded and led by Jason Calacanis. 

You’ll probably recognize Jason as one of the co-hosts of the All-In Podcast, This Week In Startups, being the 3rd or 4th investor in Uber, plus investing in a slew of other companies that are just absolutely bananas to think about (Robinhood and Calm, for example).

But this isn’t about his glory. This is about 4 lessons I’ve learned working for someone that has reached levels a lot of us in tech aspire to obtain. 

Lesson 1: Don’t Be Afraid To Ask Questions

As I began to rise in my career, I felt more and more pressure to be the guy with all of the answers. I put way too much pressure on myself to be an expert in everything all of the time.

Looking back at it – that’s absolutely insane.

What I learned real quick from Jason is that no one knows all of the answers. What matters more than knowing it all, is being able to learn quickly and grow from there.

I remember the first time I was in a meeting with J and he didn’t know something. Without a beat, he asked for an explanation, learned what it was, then continued on the discussion in a productive way. 

If someone as successful as Jason can quickly admit when he doesn’t know something, so can I. 

Lesson 2: Remove Friction

Don’t make a user’s life harder. If something is 3 clicks, make it 2. If it’s 2 clicks, make it 1. Don’t stop the flow of life. Remove all friction points wherever they are, as often as possible. 

Lesson 3: Be The Samurai, Sharpen The Blade

If you find some gold, don’t stop there and make a new hole. Keep digging and grab all of the gold before you move onto a new spot.

Be like the samurai – master a craft and have incredible focus. 

As an ADD kid, like most, I get distracted by shiny object syndrome. Correction – I GOT distracted by shiny object syndrome. 

Jason taught me the importance of focus and mastering task. He taught me to be the samurai and sharpen the blade.

When I started doing this, my work output and success levels increased 5x. 

Lesson 4: Stop with the marketing bullshit

As a marketer, this is always tough to hear Jason say, but I get it. No one wants to be marketed to. The bright lights and annoying as hell fluff is, as he says, bullshit.

Get to the point. Talk like a human. Make life easy for those on the receiving end of your marketing.

The more human and simple you are, the better the results.


Alright, there you have it folks. 4 lessons I’ve learned working for Jason Calacanis.

Oh, and I can already hear it now… “Alex, why 4? Not 3 or 5 like most blog post formats.”

My answer is simple – because screw what everyone else is doing. I have 4 things to share and that’s what I did. 

Hope they help you like they’ve helped me. 

– AJM

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About Alex

Alex Medick is an entrepreneur and occasional investor from Las Vegas, Nevada.

If you want to jam about startups, growth, product, Bitcoin, punk rock, or surfing – he’s your guy.(more)

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