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
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 · Makerpad.co
@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
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?
David Turner
David Turner@dturneresq · RSA Fellow
How is the startup ecosystem doing right now, in your opinion? Is it easy enough for good companies to thrive, or is it all full of hucksters and snake oil salesmen, or is it a mix? Has it gotten better or worse in the past few years?
jason
jason@jason · ceo, writer, event host & angel
@dturneresq 1. too many companies, 2. too many angel funded companies, 3. not enough VCs to do proper A rounds (the series A crunch is now very real) and 4. too many incubators accepting too many startups (YC at 100+ over two days is just insane IMO). We have too many babies... and not enough milk. It's gonna continue to get ugly... lots of dead companies out there right now that are literally on fumes. We need to do less, but do it better.
Elaine Lu
Elaine Lu@elaineluyi · Co-Founder & CEO, Visbit Inc.
@Jason Hi Jason, so great to see you here! Really like your #AskJason and @TWistartups. A lot of helpful advices! My questions to you: what are the traps (something looks right to do but actually not) you would suggest early stage startup (before A round) founders to pay attention and try to avoid. Thanks a lot!
jason
jason@jason · ceo, writer, event host & angel
@elaineluyi most folks are not focused enough on their customers; they don't use user testing, they don't do street teams, they don't do user intereviews, etc. get close to your customers, then get closer.
Jason Botello
Jason Botello@jasonbeee · Jidly LLC
Hey @jason - totally unrelated but as a fellow Jason, I'm just wondering what you think of our name in general. Also, do you know who decided on your name and if there's any specific reason they did so? For example, my dad named me because he loved "Jason and the Argonauts". Thanks!
jason
jason@jason · ceo, writer, event host & angel
@jasonbeee I'm Greek, it's a great Greek name as you point out. 'nuf said!
Rupert Cheek
Rupert Cheek@rupertcheek · Founder, Cheeky Promo
@jason I was named Rupert after the poet Rupert Brooke.
Emily Snowdon (née Hodgins)
Emily Snowdon (née Hodgins)@emilyjsnowdon · Operations @ Product Hunt
@jason thanks for being here today! What is one moment in your life and career you wish you could relive & why?
jason
jason@jason · ceo, writer, event host & angel
@ems_hodge My life is so fucking great I don't even think about my past mistakes.
Mark Daniel
Mark Daniel@markdaniel94 · CEO, Strut
@jason What was the scariest day of your career? What did you learn from it?
Erik Torenberg
Erik Torenberg@eriktorenberg · Former Product Hunt
@Jason You have so much to be proud of, but what's something you're _not_ proud of and what did you learn from it?
jason
jason@jason · ceo, writer, event host & angel
@eriktorenberg When I was younger I was combative and desperate to be successful so I would sometimes run over good people who worked for me. Sometimes those people deserved to be fired, sometimes they were idiots, but none of the time did I need to lay into those people -- and sometimes I did. I used to think it was my job to be brutally blunt and tell folks "that's stupid, only a stupid person would do that... and you did it twice--so you're a real idiot!" That's how my dad talked to me, and how people talked to each other in Brooklyn. I thought this was normal, but over the years I've learned that most folks do not talk like this. Now I think to myself "this person is a f@#$king idiot.... and they're working me... that's my fault!" Then I tell my chief of staff, "This person is not a fit for our company, give them some severance and let them know it's not fit and we'll give them a great reference." it's much cleaner this way!
Spotlight
Spotlight@_spotlighthq
@jason I probably learned more from your podcast than I did in 4 years of college. Are there any episodes coming up you are excited about? Or future guests you really want to have on the show?
jason
jason@jason · ceo, writer, event host & angel
@_spotlighthq fans really want to have Sheryl Sandberg, Zuckerberg and Elon Musk on the show. would love to have them all on, to be sure. for the show, I'd really like to get out in the real world with a video crew more often.... like visit a new power plant/nuclear reactor, the gigafactory, new telescopes,etc. I want to take on bigger topics on location... which takes massive budget. we'll get there soon
vinceromanelli
vinceromanelli@vinceromanelli · Owner, rePercussion
Do you think there's a way for a entertainment/music business to be treated like a tech startup with VC's/AI? Or do they usually need a tangible product?!
Rupert Cheek
Rupert Cheek@rupertcheek · Founder, Cheeky Promo
@vinceromanelli Good question
Daniel Mirolli
Daniel Mirolli@ddmirolli · Lead Sales Manager at @Signpost
@vinceromanelli take a look at Sandwich Video and their partnership with Ludlow Ventures. Similar to what you're hinting at with this question http://www.forbes.com/sites/elle...
vinceromanelli
vinceromanelli@vinceromanelli · Owner, rePercussion
@ddmirolli Thanks Daniel!
Jack Dweck
Jack Dweck@jackdweck · Product Manager at Unroll.Me
@jason - I love that you're rating questions. How did you come up with your brilliant scoring system?
Kunal Tandon
Kunal Tandon@kunaltandon · kunaltandon.com
@jason From the outside there is no company hotter right now than Uber, besides regulatory hurdles, what do you think are the biggest threats to its business today and in the future?
jason
jason@jason · ceo, writer, event host & angel
@kunaltandon Uber is operating in the real world and they are only as good as their current wait time... it's a brutally hard business to run and without folks like Ryan, Emil, GMC, Travis and the rest of the team, it simply would not exist in the world. my hats are off to the entire team over there.... they really suffer over every tiny detail so that our lives are easy and smooth. Long way of saying EVERYTHING matters in a huge way when you are in such a real world business. if Product Hunt lets a lame product into the top 10 every now and then no one notices... if your Uber driver makes a wrong turn or is 2 minutes late many people explode in a rage on twitter! it's like that Luis CK bit where people don't appreciate how amazing some of these services are. I'm so proud of the team over there.... just great people.
Kate
Kate@katesegrin · Head of Social @ GitHub
@jason what is the most fun/zany thing you've done in the past year?
jason
jason@jason · ceo, writer, event host & angel
@katesegrin I almost went wing walking at my friend Elon Musk's birthday party. Right before they called my name they ran out of time!!! I was really disappointed, but it was amazing to see all my friends get up on the top of biplane!
Irina Jordan
Irina Jordan@irinajordan · Director of Inbound Marketing
@jason What is your forecast for the upcoming Launch Scale? Any front runners in your mind? Thanks.
jason
jason@jason · ceo, writer, event host & angel
@irinajordan we have like 40 of the 50 speakers selected (launchscale.net) and we've given 2,500 founders free tickets -- so it's going to be AWESOME. I won't know the best speakers until reherels which start right after I get off this AMA! Kyle from HomeHero, Sacks from Zenefits and Tony from Zappos all look promising. solid question: 8
Sara Tekula
Sara Tekula@spectekula
@jason Hi! I'm a friend of Tommy Russo here on Maui. Looking for your instant gut reaction here. My husband and I completed a 50-state native tree community planting tour, GPS marked all of the trees, and filmed the whole thing (and interviewed tons of great people) and are trying to figure out what to do next. What immediately comes to mind? We want to share the experience far and wide.
Sara Tekula
Sara Tekula@spectekula
@spectekula I should also mention that - the tour was crowdfunded...and while on the road between 2010 and 2011, we had a great social media campaign going with relatively good engagement....how do you tell good stories after the live action is over?
Mac Alnakari
Mac Alnakari@malnakari · Founder, Native
Hi @jason what is the deadline for application submissions for your @launchincubator?
jason
jason@jason · ceo, writer, event host & angel
@malnakari excellent question... 9 of 10 on my scoring system for questions. we accepted 2 of 7 already, so get your application in early and you will get reviewed early. Also, make friends with my friends and convince them to tell me why your product kicks ass--and why you'll never give up.
Goliath X
Goliath X@goliath_x
@jason Your scoring system is biased :)
Colin Masters
Colin Masters@colinpmasters · Freelance iOS Engineer
@Jason - What do you think about the business model of North Technologies and the idea that you can cycle through product ideas to see what gets traction?
jason
jason@jason · ceo, writer, event host & angel
@colinpmasters It worked for Kevin, but kevin rose is a legend who can easily raise $5-10m to pursue a vision like "we'll try things until something works... then we'll go all in." ... and he did it!
Nicolo S
Nicolo S@coconidodev · Founder/CEO - CryptoAnalyst.co
Hi Jason, I have been regularly listening to TWIST for a very long time now and you have really played a major part in inspiring me to do great things, start my own apps company and much more! My question to you is: 'What inspired you to start the show and how do you stay motivated to constantly come up with new and engaging content for the podcast whilst still managing all your other projects? Best regards, Nicolo S
jason
jason@jason · ceo, writer, event host & angel
@coconidodev I'm an extreme extrovert, which means that my energy level GOES UP after I talk to people. I get to talk to over 104 exceptional people every year.... which means for the 10 hours after the interview I'm super pumped up! That means for 1,000+ hours a year I'm carrying the energy boost of those interviews. for an introvert, from what they've told me, they need 10 hours to RECOVER from an hour of doing a podcast. exceptional question: 9.5 of 10
Kevin Strasser
Kevin Strasser@kjstrasser · CEO TribeBoost / Founder MoSquatch
Hi @jason. Been a big fan of your work going back to the Silicon Valley Reporter days. What is your take on Twitter Video? Do you think we will see mass exodus from YouTube to native Twitter video once the time limits are bumped up for everyone?
jason
jason@jason · ceo, writer, event host & angel
@kjstrasser If/when Twitter announces a 70/30 revenue split with creators, and makes a basic landing page for videos that feels like a YouTube page, they will become a significant competitor. Youtube is at 1b users a month, so they will not being going away for a decade or two... but Twitter could get to 1b video users easily.
Kunal Tandon
Kunal Tandon@kunaltandon · kunaltandon.com
Hey @jason, many people feel that with the continuing shift towards mobile, and an increasing reliance on apps vs. mobile web- that trouble might lay ahead for Google as traditional search becomes disintermediated? Do you agree with this assessment, and if so, what can Google do to position itself better for this emerging new normal?
Parker Agee
Parker Agee@parkeragee · Software Engineer
@jason do you think a box subscription business has the ability to become a billion dollar company? Or are they too much of a niche to reach that scale?
jason
jason@jason · ceo, writer, event host & angel
Ron Valderrama
Ron Valderrama@streamnowceo · CEO, Stream Now TV
@jason I am in the content space which I know you hate. What factors would play into you investing in a one off content company?
Ankit Minocha
Ankit Minocha@ankitminocha
@jason What's your opinion on startups being overvalued these days?
jason
jason@jason · ceo, writer, event host & angel
@ankitminocha investors can pass, and I do every day, based on valuation. I look at the top 10 Ycombinator companies every class -- literally do in-person meetings with them -- and I've passed on the last 20 or so in a row based on valuation in many cases. Why? Simple: I see almost all companies due to my reputation/deal flow/social following. If I can invest in 2-3 startups at $3m valuations for every $8-15m valuation from YC, well, that makes great sense for me. This doesn't mean other folks shouldn't invest in YC companies, but I can tell you the startups themselves are making a mistake by being 2-3x market rate--they're losing the elite investors by doing so. On the late stage the TPG and Fidelity type folks get their money out first... so they have little downside risk. So, the valuation thing is always fun to talk about, but in practice investors get to set the market -- and they are very bullish.
Varun Deshpande
Varun Deshpande@varund7 · N/A
@jason Hello Jason! I'd like to say well done on your recent weight-loss. Any particular services or strategies you used to get there?
jason
jason@jason · ceo, writer, event host & angel
@varund7 Lost 10 pounds in 30 days on keto diet. It's hard to give up sugar and pizza and bread, but I feel so good... and 2lbs a week is soooo noticeable. Went to the doctor today (do keto with a doctor, not on your own) and reupped to do another 10 pounds/30 days... so wish me luck. you can also do crossfit and just eat healthy and lose 10lbs of fat/add 5 lbs of muscle -- i did that before the keto. 213 was my peak fatness 195 when I started keto diet 185 today! goal = 176 (I'm 5'8")
Tys Bradford
Tys Bradford@tysbradford · App Developer & Founder of BlueTropical
@jason Big fan of the show. Thanks for making my daily commutes bearable. I am curious to know how an investor with a profile like yours deals with the (I imagine) constant stream of pitch decks coming at your from every which way. What filters/systems do you have in place to process these pitches without letting the next 100x opportunity slip through the net?
Gale Wilberger
Gale Wilberger@cluelessnphx · Retired, invester, curious...
@jason many of our best and brightest appear to be creating stuff, crap, apps etc that isn't necessary. Is this a concern to you and your peers or just current culture...?
jason
jason@jason · ceo, writer, event host & angel
@cluelessnphx people want to build things.... that's fine, as long as they don't raise a bunch of money and blow it, no one is really harmed. If you want to buy a bunch of cameras and shoot a bunch of video, but you never get to Sundance or HBO, it's ok... you had fun, you lost $5,000 on your hobby... it's all good. if you take investor money that's when things change, and you can't look at it as just fucking around with your friends all day.
Craig Stanford
Craig Stanford@craigstanford · Co-Founder & VP of BizDev @ StageHound
Speaking of Mahalo, what are your least favorite letters of the Alphabet and why?
David Maliglowka
David Maliglowka@davidmaliglowka · Drops
@jason Hi Jason, I receive the launch ticker everyday and was wondering what your thoughts are for email in the future. Will email still be necessary in the next few years or with the rise of messaging apps will emails be a technology of the past?
jason
jason@jason · ceo, writer, event host & angel
@davidmaliglowka email ain't going anywhere... in fact, I'm an investor in a stealth company that is gonna make it REALLY awesome again
Taufiq Husain
Taufiq Husain@taufiqhusainca · Managing Director at Polar Hills.
Hey Jason, I love Uber & Thumbtack both so thank you for finding them so early and investing in them. I actually learned to play guitar this summer using Thumbtack! My question is this: How do you get access to early-stage founders? What would you say to me if I wanted to become an early-stage angel investor in 5 years? I'm asking because I've only invested publicly so far but I want to get into private-stage investments someday and I'd love some tips from you.
GG
GG@ggonweb · Connecting my thoughts ...
What do you think about future of eCommerce after amazon? Is the 'buy' buttons the social eCommerce we had been waiting for?
Ivan Raiklin
Ivan Raiklin@ivan_raiklin
@jason Thoughts on the new initiative by the Secretary of Defense, Ashton Carter to connect DOD with the Valley. Is there any interest on the part of Super Angels like yourself to diversify the angel portfolio into the National Security space DOD/IC/USG writ large? See you at Launch Scale & IoT!!! and Tech Crunch?
jason
jason@jason · ceo, writer, event host & angel
@raiklin I would love to help defend out country, or back companies that do. however, we have to remember that our country was built off of freedom, privacy and... ummm.... not torturing people. The USA has lost the high-ground and we need to get it back by showing we value privacy, human rights and justice ABOVE even our own short-term safety -- and that's not an easy thing to do.
Julien Jacques
Julien Jacques@julienjacques
@jason Do you have any good resources for proper SaaS pricing?
Julien Jacques
Julien Jacques@julienjacques
@jason that sass
Jisa
Jisa @jisagigi
@jason What do you think about the future of TVApps?
jason
jason@jason · ceo, writer, event host & angel
@jisagigi i love thetake.com and could see that working big time on the new apple TV or inside of Netflix/HBO Go
Mantalena Kaili
Mantalena Kaili@mantalenak · CEO,made
@jason hello, which do you think is the hottest trend and the biggest trap for startups ?
jason
jason@jason · ceo, writer, event host & angel
@mantalenak on demand, VR, AR and 'chat as an interface' (scout travel, magic, operator, etc)
Timur Insepov
Timur Insepov@rightofbrain · Courage builder
Really enjoy @TWiStartups. How do you stay productive and even throw in a periscope or two every once in a while?
jason
jason@jason · ceo, writer, event host & angel
@rightofbrain i have an emmy-award winning producer, a chief of staff and an EA. they do all the work, I show up and host.... makes things really easy.
Julien Jacques
Julien Jacques@julienjacques
@jason Your interview with Cambrian Genomics founder was amazing. Do you have any thoughts or anything regarding the founder and his death? I contemplated quitting everything and trying to just go and help them, but then found out the founder had committed suicide. That guy seemed so smart and they were building something amazing. If you can't comment on his death, can you comment ton that industry and specialized personal health using biotech?
Javier Torrez
Javier Torrez@jactorrez
@jason Is there any piece of advice you've gotten early on in your career that you regret listening to/not listening to?
jason
jason@jason · ceo, writer, event host & angel
@jactorrez people keep telling me to be patient and good things would happen -- that's just bullshit. Dont wait, make it happen.
Anup Gosavi
Anup Gosavi@_anupg · Building Spext.co
Many a times, ideas that are revolutionary (AirBnb) and ideas that suck often look the same at pre-seed/ seed stage. What can founders do to assess? As a investor, what do you do to assess?
jason
jason@jason · ceo, writer, event host & angel
@_anupg I look in the founder's eyes and see if they have the eye of the tiger.
Heath W. Black
Heath W. Black@heathwblack
@Jason Two questions: 1. Zirtual... I've seen a million different responses, accusations, etc hurled... Can you succinctly state what you knew, what (if anything) you could have done a better job of communicating, and what you learned from the mess? 2. Despite looking somewhat competent, what record do the NY Knicks end this season with?
Vitor
Vitor@vit05 · tapan.ga
@jason What do you think is the best filter for general content ? Friends, Vector/Machine, Journalists, successful people ?
Soroush Ghodsi
Soroush Ghodsi@soroushg_ · Founder Slik.
Of all places you were invited why did you come to Waterloo for Hack the North? Was there something that intrigued you? Do you have any investments here?
Soroush Ghodsi
Soroush Ghodsi@soroushg_ · Founder Slik.
What do you think of the deal intelligent space? Mattermark, Datafox, etc I think you had something like that way back!
Sako
Sako@sarkisbuniatyan · Founder of Aztrana
Hi @Jason, superfan here, thank you for everything! Question: Would you invest in a company in Sweden if it inspired you?
Tripp Eckerline
Tripp Eckerline@eckerline · Investments
@jason what's your opinion on the future of Palantir?
jason
jason@jason · ceo, writer, event host & angel
@eckerline I don't know enough about what they actually do.
Craig Stanford
Craig Stanford@craigstanford · Co-Founder & VP of BizDev @ StageHound
@jason You don't really want to know and the good news is Plantir does not want you to know either.
Patrick M. Hodgdon
Patrick M. Hodgdon@patrickh · Storytelling & Go-To Market Strategy 💡🚀📈
What are your thoughts on the political engagement space that Brigade and Countable are going after? Do you think they can get enough people engaged to create real policy change?
jason
jason@jason · ceo, writer, event host & angel
@patrickh I think it's DOA until it's not... which is to say, no one has ever made it work and I don't think anyone will. Politics in this country is just so f@#$ked I'm not sure software will solve the problems (two party system, big money buying politicians). I'm willing to be proven wrong... but I'm not wrong that often. :-) solid quesiton: 8.5
Nicholas Sheriff
Nicholas Sheriff@nicholassheriff · Founder, Medic Ventures
@jason Hi Jason what are some of your criteria when deciding on investing in a startup. Given that you were one of the first investors in Uber what clicked be it metrics, market or team. Also do you personally do smaller seed investments...currently trying to raise a seed round for my startup at the moment. Here is our product - https://itunes.apple.com/app/app... currently being featured by Apple in two sections - 2 months old and we've already been contacted to be featured with a banner spot and we're seeing 150% growth weekly.
Paul Tomkinson
Paul Tomkinson@paultomkinson · Founder, Textras
@Jason What would it take to get you to the Nantucket Project? Big fan from day 1. 👊 (asymmetrical friendship).
jason
jason@jason · ceo, writer, event host & angel
@paultomkinson host the nantucket project in july or august and it would be easy!
Adam Qureshi
Adam Qureshi@adamqureshi · Qureshi MEDIA
hey @jason, im setting up a " UX design as a service" empowering recent grads in NYC. Would love your feedback! launching landing page next week, testing the idea. Would you mind if i send it to you for endorsement?
jason
jason@jason · ceo, writer, event host & angel
@adamqureshi my endorsements typically come in the form of AN INVESTMENT or when I use and love a product; make something I love... or that I love enough to investin, and I will never shut up about it!
Adam Qureshi
Adam Qureshi@adamqureshi · Qureshi MEDIA
@jason #form of AN INVESTMENT. Legit! will send you link on launch.
Matt Zeltser
Matt Zeltser@mattbk718
Hey @jason from a fellow Brooklynite(bay ridge!). What was the hardest part in the very beginning (the very very beginning) of being an entrepreneur? What were the first and biggest hurdles you had to get over that you didn't know how to get over? Thanks
Javier Torrez
Javier Torrez@jactorrez
@jason I often see you tweet about your family, and so as someone who's an "insider" in tech and has the opportunity to get a glimpse of companies that may potentially shape the world they live in in the future, what worries you most about that future? And what are you most optimistic about?
jason
jason@jason · ceo, writer, event host & angel
@jactorrez I'm optimistic with the exception of radical Islam, which is growing and singular in it's vision: one nation! kill the apostates! Radical muslims are only 5-10% of muslims but they are so brutally violent and dangerous that they other 90% can't stand up to them (would you? get beheaded or burned alive on camera for your family to watch). Putin makes me very nervous because, like radial Islam, he wants to take over the world. So, I nervous about supervillians who want to take over the planet and kills folks... but energy, water and food startups can solve for. :-)
Anthony Miller
Anthony Miller@anthonyrmiller · CEO, millermedia7
@jason Hi! My company developed an MVP for a client and he is looking for funding, how much does geography play apart in getting funded? Should we just pitch any possible opportunity, anywhere?
jason
jason@jason · ceo, writer, event host & angel
@anthonyrmiller look at the top 10 cities for funding.... consider what life would be like for you and your startups in each.... then move to the #1 city. startups are hard enough, follow the money!
Ivan Raiklin
Ivan Raiklin@ivan_raiklin
@jason Thoughts on the new initiative by the Secretary of Defense, Ashton Carter to connect DOD with the Valley. Is there any interest on the part of Super Angels like yourself to diversify the angel portfolio into the National Security space DOD/IC/USG writ large? See you at Launch Scale & IoT!!! and Tech Crunch?
Javier Torrez
Javier Torrez@jactorrez
@jason To this day, your interview with Peter Thiel is still one of my favorite interviews that you've done. I recall you saying something a long the lines of it being the toughest interview you've done. What is it like to sit down and have a conversation with Peter Thiel on/off camera? Is he as intense as he appears to be when he's on stage?
Ondieki Obare Jr.
Ondieki Obare Jr.@ondiekijunior · CEO, Mteja
Now as a tech investor, what's your take on investing in the Africa tech space
jason
jason@jason · ceo, writer, event host & angel
@ondiekijunior investors need to focus on the startups they can meet with in an hour.... so, Africa and South America need their own, home grown, angels. I'm busy, can't get on a plane.
Conor O'Phelan
Conor O'Phelan@conorop · Co-Founder, Dojour
What is one "problem" that you face on a regular basis that no one appears to have solved yet?
jason
jason@jason · ceo, writer, event host & angel
@conorop getting old
Paresh Srivastava
Paresh Srivastava@2wity · Founder
@jason Hi, How do you pitch to an investor with an idea that is THE next big thing when you are constrained with technical knowledge, funds and people to build a demonstrable prototype?
jason
jason@jason · ceo, writer, event host & angel
@2wity you go to work for someone who can teach you and sharpen your skills. you're not ready to be a founder....
Jeff
Jeff@jefferysierra · Co-Owner, President
What are the top 3 things you tell entrepreneurs/founders to focus on every day?
jason
jason@jason · ceo, writer, event host & angel
@jefferysierra Product, Hiring and Raising money
Rupert Cheek
Rupert Cheek@rupertcheek · Founder, Cheeky Promo
@jason Why don't you fund music startups?
jason
jason@jason · ceo, writer, event host & angel
@cheekypromo because they always fail
Mark Jeffrey
Mark Jeffrey@markjeffrey · Author
What is the one highest order bit differentiator between successful companies and unsuccessful companies? Michael Moritz (when visiting Mahalo) said (paraphrasing): 'manic focus on being the best in the world at one thing only'. However, Bill Gross recently did an analysis of all of his companies over the years and concluded, 'timing', surprisingly, mattered more than anything: even more than team, more than execution. Where do you stand?
jason
jason@jason · ceo, writer, event host & angel
@markjeffrey timing and product focus are too sides of the same coin; being at the right place at the right time is great -- but not with the wrong product. I think culture matters after you get those two things right.. and by culture I mean the founder(s) saying "this is who we are, how we work and what's we're trying to accomplish," not here's free food and a keg on Friday's.
Bill Farrell
Bill Farrell@billfarrellpm · Director of Product at @HelloSign
@jason Are API businesses (Stripe, Twilio) the future or a fad right now?
Tripp Eckerline
Tripp Eckerline@eckerline · Investments
How much Uber have you taken off the table and if so at what valuation did you start trimming?
Javier Torrez
Javier Torrez@jactorrez
@jason Are there any qualities in entrepreneurs running successful companies you've seen over the years that made you go, "That's a quality every entrepreneur should have", or do you think most entrepreneurs are successful because of how different they are from the 'norm'? I.e seeing the world differently, going against the grain, etc.
Narek Khachatryan
Narek Khachatryan@narekk · Product Designer
Thanks for joining us, @jason. Do you think Silicon Beach will live up to its name?
Hi @jason do you think it could make sense to launch a new project in a less competitive market and consider switching to a bigger and more competitive market after if it catches high traction?
Jared Schnelle
Jared Schnelle@schnelle · Founder, Forge
@jason I've been trying to get in contact with Microsoft BizSpark Plus since I met with the vendors at the Launch Festival in March. They were promising attendees they would receive BizSpark Plus acceptance by just stopping by the booth and talking with the reps. We really need the 120k in Azure credits from Plus but I can't get anyone to reply to emails. Yesterday, I spoke with a Microsoft employee in charge of Azure on-boarding and she said that she's had many similar complaints (about lack of BizSpark Plus communication not Launch Festival vendors) and I don't know what to do other than to reach out to you and ask for some help since you probably have a higher up contact than I do. Want to help me get 120 dimes from Microsoft so we can focus on building our product and not worry so much about initial scaling? My Twitter is @schnelle and my email is schnelle@forge.us -- Thank you.
Jonathan Kingsley
Jonathan Kingsley@jfkingsley · Founder, Refractal
Hey @jason! As someone building a product in a relatively untapped area, I get the "you don't know what people want until you give them it" schtick a lot, but I was wondering if you had any tips on user experience and marketing when it comes to building things completely different to the status quo?
Reed Berglund
Reed Berglund@reedbfree · CEO, FullBottle
@jason Uber chose to focus on a niche market e.g. SF, Luxury Car service for their launch. Do you believe this is the most effective strategy to drive early conversions in a marketplace model?
Constantijn Seys
Constantijn Seys@seysconstantijn
Hi Jason, Can you talk about your friendship with Elon Musk? Must have been really scary to buy a car if you knew that Tesla was struggling. Thank you for This Week in Startups, learned a ton from the show. My favorite moment:
cedric deweeck
cedric deweeck@knoddecee · Co-founder Hivemind
How do you transfer your knowledge with your investments? Only through conversations, or did you create playbooks for certain things?
Craig Zingerline
Craig Zingerline@craigzingerline · Product, Growth, Entrepreneuer
Couldn't make this live but was great reading the transcript after. Thanks for doing this!
Mukesh lodhia
Mukesh lodhia@mlodhia1000 · Product Developer, UXC Eclipse
@Jason, Any interests in investment outside US?
Oscar Rundqvist
Oscar Rundqvist@oscarrundqvist · Swedish tech entrepreneur
Have you invested in Swedish startups yet? If not; hello, my name is Oscar. I am currently developing the next social network. How can I contact you further?
daniellevine
daniellevine@daniellevine · Fireside
Hey @Jason, what's the best thing you've come across in the last 30 days? Could be a product, article, quote, restaurant. Anything. And why?
Mark Michuda
Mark Michuda@markmichuda · CEO CallOnTheGo
I agree! @jason is great!