jason

Jason Calacanis

Outspoken serial entrepreneur, angel investor, podcaster and writer

THIS CHAT HAPPENED ON September 16, 2015

Discussion

jason
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!
Julien Jacques
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.
jason
jason@jason · ceo, writer, event host & angel
@julienjacques you have great taste
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:
jason
jason@jason · ceo, writer, event host & angel
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
Daniel Mirolli@ddmirolli · Lead Sales Manager at @Signpost
@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
Matt Silverman@mattjsilverman · Product Designer
@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.
Sean Wesley Smith
Sean Wesley Smith@seanwessmith · SAP Admin
@rrhoover @GaryVee called Shark Tank as cancelled at 26:00. That show turned around quickly with Chris Sacca showing up this season with a regular 11 M viewers.
Eric Willis
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?
jason
jason@jason · ceo, writer, event host & angel
@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
Eric Willis@erictwillis · Working on something new
@jason Thanks for the response. I've always wondered that about you since you do so much.
Ben Tossell
Ben Tossell@bentossell · newCo
@jason Hey Jason! - What is the craziest thing you've seen in a pitch that you can tell us about?
Paul Robert Cary
Paul Robert Cary@prcary · CEO, Findie | www.findie.me
@bentossell great question Ben! 😀
Paul Robert Cary
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?
jason
jason@jason · ceo, writer, event host & angel
@paulrobertcary post should still be online.... nothing has changed. YouTube is a great place to build a brand, but sucks for making money. The top guy makes like $5-10m a year.... and youtube makes $7b?! really?
Hey @jason what are your favorite books?
jason
jason@jason · ceo, writer, event host & angel
@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
Ray Hernandez@raydawg88 · Creative Director - Product Maker - Dad
Question: Since you have a young daughter, what do you think is missing from early education system, that tech/startups could fix?
jason
jason@jason · ceo, writer, event host & angel
@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
Ray Hernandez@raydawg88 · Creative Director - Product Maker - Dad
@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
Daniel Mirolli@ddmirolli · Lead Sales Manager at @Signpost
@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
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?
jason
jason@jason · ceo, writer, event host & angel
@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
Eli Colner@rivveting · Founder, Salience
What is @Ryan building and how much have you invested?
jason
jason@jason · ceo, writer, event host & angel
@rivveting I have no comment. :-p 10 of 10 question!
Veronica Belmont
Veronica Belmont@veronica · Destroyer of Worlds (and PM at Disco)
@jason I love that you ranked the questions.
Daniel Mirolli
Daniel Mirolli@ddmirolli · Lead Sales Manager at @Signpost
Hey @jason - If you could say one unfiltered thing to A) my generation, B) the government, and C) the generation to come - what would it be?
Ryan Bednar
Ryan Bednar@ryanbed · RankScience CEO
@jason How did your Uber investment come about?
jason
jason@jason · ceo, writer, event host & angel
@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!).
Mark Devlin
Mark Devlin@mark_devlin
@jason Given the demise of Mahalo.com at the hands of Google, do you think there's still room for a human-curated search engine?
jason
jason@jason · ceo, writer, event host & angel
@sparkzilla clearly human curation is still maturing. I probably took on too much doing search, but if you look at Product Hunt itself, it's curation of just one thing: tech products. so, Mahalo may have failed, but the concept of curation is just getting started.
Ryan Hoover@rrhoover · Founder, Product Hunt
Agreed. Google primarily uses algorithms combined with some editorial and social influence, but there are so many different ways to surface and add context to "stuff". 😉
Paul Robert Cary
Paul Robert Cary@prcary · CEO, Findie | www.findie.me
@jason @rrhoover Yes! 😀Knowing what people like about what they like is critical.
Timur Insepov
Timur Insepov@rightofbrain · Courage builder
@rrhoover ... and build APIs around that "stuff" so the next app can benefit from new context.
Sydney Liu
Sydney Liu@sydney_liu_sl · Co-Founder of Commaful.com
@jason Hi Jason, Huge fan of TWIST, #Jason, LAUNCH Ticker, and LAUNCH conference. I consume content every day while exercising or cooking. You have always said you love great design and you emphasize great products (talking about InVision and more). What company that isn’t main stream yet do you think does design really well and what do you think they do well in the product? Best, Sydney
jason
jason@jason · ceo, writer, event host & angel
@sydney_liu_sl Thumbtack, hands down. The product is super elegant and wildly effective.... and the mobile experience is just delightful. Beyond simple, but seriously complex on the backend. Butterfleye camera and Birdi air quality/smoke detectors are two hardwre products i loved enough to invest in... i'm hopeful there. Wrapify, Bento and Scout are among the many incubator graduates that have exceptional design (real world and virtual) that you should take a look at.
Erik Torenberg
Erik Torenberg@eriktorenberg · Former Product Hunt
@Jason Thanks for joining us! What advice would you give to your 25 year old self? Put differently, what would you do if you were 25 in 2015?
jason
jason@jason · ceo, writer, event host & angel
@eriktorenberg I would be a founder. :-)
Daniel Mirolli
Daniel Mirolli@ddmirolli · Lead Sales Manager at @Signpost
@jason - is it more important for entrepreneurs today to dream big dreams or attainable ones?
jason
jason@jason · ceo, writer, event host & angel
@ddmirolli solid question--an 8.5 of 10 on my scale! You have to have a huge, big vision but take small steps. So, for Uber you need to make sure that the first 100 riders in the system get a great ride and don't wait a long time.... while still imagining 1,000 riders an hour across 300 cities getting a great ride.... which is two very different challenges. The important thing to remember is that products are experienced, typically, one user at a time.... so, if you can't make the experience magically for one person don't focus on anything else but making that one person delighted.
Daniel Mirolli
Daniel Mirolli@ddmirolli · Lead Sales Manager at @Signpost
@jason Thanks for answering and for being available to do this! Greatly appreciated by all who listen
James Sowers
James Sowers@jrsowers_
@jason, what is the best thing that regularly pops up in your inbox (ex: newsletter, potential deals, introductions, etc.)? What has someone sent you recently that made you smile or otherwise struck a chord with you?
David Carroll
David Carroll@profcarroll · associate professor at parsons
Do you think #IStandWithAhmed will come up in tonight's GOP debate?
jason
jason@jason · ceo, writer, event host & angel
@profcarroll I had no idea the GOP debates were tonight.... pass the popcorn! Trump is going to crush it in the ratings I'm sure.... Ahmed will not come up.... I doubt it.
Timur Zhiyentayev
Timur Zhiyentayev@tima_zhi · Cofounder of Drizzle
@jason, I have read you started Mahalo. I've recently built a website where people share crowdsourced reviews for certain search categories. Would you let me know about possible pitfalls or problems for human-reviewed directories? Thanks!
Jesse Barkasy
Jesse Barkasy@jessebarkasy · owner www.mesa9.com
@jason How did you find Uber and decide to invest?