Jason Calacanis
Outspoken serial entrepreneur, angel investor, podcaster and writer
Discussion
M
jason
@jason · ceo, writer, event host & angel
Hi, I'm Jason. I was the second Angel investor in Thumbtack and the 3rd investor in Uber. Ask me anything!
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Julien Jacques
@julienjacques
@jason Not a question, but a statement. This #askjason is probably the best piece of advise ever given to a startup. PERIOD.
Ryan Hoover
@rrhoover · Founder, Product Hunt
Jason! As you know, I've been watching your show, This Week in Startups, since episode 1. What's your most memorable moment in the 578 (!!!) shows you've recorded? #24 with @garyvee from 2009 is one of my favorites:
That's an great question.... I have so many amazing moments, from obvious ones like Sacca, GaryV and @DHH, but for me right now my favorite episode is the one I did with my friend Dave Goldberg who passed this year. I haven't been able to watch the whole thing, but I have watched a couple of minutes since his passing a couple of times to hear his voice again.
It's a great episode, with a great man... who I miss very much.
Daniel Mirolli
@ddmirolli · Strategy @SimFinOfficial
@rrhoover there's also a really authentic moment where you get to see @jason 's heart for his friend at the end of the episode of TWIStartups with Jeff Dachis, CEO of OneDrop. Thanks for the reminder to love and be loved, @jason http://calacanis.com/2015/06/04/...
Matt Silverman
@mattjsilverman · Product & Design
@rrhoover there are literally too many to name. I am also a huge long time fan of This Week In Startups and have watched just about every episode (I'm hoping I have, I really tried). My 10, 20, 30 favorites I have watched countless times to this day. @jason has been a gigantic influencer on my life personally and in tech.
Eric Willis
@erictwillis · Working on something new
@jason Hello Jason. Do you ever think that doing so many things negatively impacts your ability to get the full potential out of a project/startup like Inside or do you see all of those activities as a kind of synergy that makes everything go?
@erictwillis I do think of that, but I enjoy doing many things right now. Over time you will see me do less CEO-ing and more media/investing/hosting conversations -- because that's what i'm best at and what I enjoy most.
being a CEO is just brutal and i've done it for 25 years.... right now I want to be an angel and do media stuff (write, TV/podcasts, books, conferences, etc).
i highly recommend people do not follow my example; focus on one thing and one things only -- that you love.
great question: 9 of 10
Eric Willis
@erictwillis · Working on something new
@jason Thanks for the response. I've always wondered that about you since you do so much.
Paul Robert Cary
@prcary · CEO, Findie | www.findie.me
@jason you wrote a blog post in June 2013 entitled "I ain't gonna work on YouTube's farm no more" that was part of my inspiration to start my company. That post has since been removed / deleted. What has changed for you about premium online video since then?
@alfink92 i love audiobooks.... because my eyes strain when I read physical books. There are some epic performances in audiobooks like Shadow Divers, The Martian and 'All over but the shoutin' '
In bios:
Something like an Autobiography
https://en.wikipedia.org/wiki/So...
The autobiogrpahy of malcolm x
http://www.amazon.com/The-Autobi...
in business good to great, five dysfunctions of a team and the checklist manifesto
Ray Hernandez
@raydawg88 · Creative Director
Question: Since you have a young daughter, what do you think is missing from early education system, that tech/startups could fix?
@raydawg88 solid question... 9 of 10 in fact. :-)
I think experiences, leadership and problem solving are the key traits I want to see in my daughter as she grows up. I don't think the education system is designed to address these skills, so I'm just bringing my daughter to my incubator -- problem solved.
that being said, there are many schools who know they need to focus on grit and the issues I listed above... so I think we'll see some innovative concepts emerge in and outside of schools. The MAKER movement and MINECRAFT are certainly two educational powerhouses that are outside the system, but now coming back into the system.
OK... I give you a 10 of 10 for this question. I'm gonna blow this up into a blog post.
Ray Hernandez
@raydawg88 · Creative Director
@jason Thanks for the answer. I couldn't agree more. I just put my kids in Montessori, and 3 traits you mention are a big focus. I do still feel like there is too much separation between the school and the parents. And that the person/company who can get the teachers and parents working together seamlessly, can do big things in education. thanks again.
Daniel Mirolli
@ddmirolli · Strategy @SimFinOfficial
@jason so excited for this post! Perhaps could be the first calacanis.com collab post with your friend Elon and the school he made for his kids?
Dan Flanegan
@dflanegan · Co-Founder, Butter
@Jason, should founders blog, podcast and tweet storm? Is there a perception that those who do are unfocused? Or are they really more engaged and exhibiting leadership qualities?
@dflanegan Larry Page doesn't blog, tweet, etc. Elon Musk *didnt* tweet or blog and now he does. Steve Jobs didn't bother, until he had a bone to pick and started writing "letters" -- aka a blog.
communicating with your audience -- aka customers -- is critical today, but I think you should be careful not to spend all your time engaging with people. you have to produce a quality product like the Model S or This Week in Startups or YCombinator before you really get taken seriously anyway. So, have a kickass product and engage with the world authentically!
good question: 8.5
Eli Colner
@rivveting · Founder, Salience
What is @Ryan building and how much have you invested?
@ryanbed I ran into Travis at a party and he said "hey, want to see what I'm working on..... "
note: i have known travis for 15 years at that time, so we were very good friends at that time -- and still are. It wasn't a new relationship like, say, Marco from Thumbtack (where I was the 2nd investor after Marco's parents!).