Jason Calacanis

Outspoken serial entrepreneur, angel investor, podcaster and writer

THIS CHAT HAPPENED ON February 26, 2016


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!
Andrew Ettinger
Andrew Ettinger@ettinger · 👟 @wearAtoms // ex @Twitter @ProductHunt
If you could name your own beer, what would you name it? cc @mlefcort
Hey @jason, thanks for joining us today for the AMA. We know your time's very valuable. I work for a tech startup called LiveNinja here in Miami, and we do white-labeled, HD video chat. I heeded your advice on episode on TWiST and had my marketing team come up with a GIF for me to include in my cold emails. I've included it in many cold e-mails, but found limited success. I know this could be attributed to a variety of factors, but I wanted to get your opinion around selling via cold email + GIF: 1. You probably operate on introductions over everything else, but have you responded to a cold email pitch recently? 2. If there was no feasible way to get an introduction (I know it's almost always possible, but still), how would you advise more "obscure" startups to approach investors and influencers like yourself in a cold email format? 3. Last, do you have any tips on the best way to incorporate gifs in a cold e-mail? Thank you for everything that you do.
Sydney Liu
Sydney Liu@sydney_liu_sl · Co-Founder of Commaful.com
Hey Jason!! Thanks for doing another AMA :D You're a master of media and content, having been a player in that industry for many years now. More recently with Inside, Launch Ticker, your blog, podcast, the list goes on. If you were to give a media/content newbie some resources (readings, talks, books, etc.) so they would know just enough to have a running start at content creation (whether it's running a podcast or starting their blog), what would they resources be? Or what would you ask them to think about? Thanks! Was great seeing you last month and excited to see you at LAUNCH! Expect many Pencil posts! Sydney Liu https://usepencil.com
Ben Tossell
Ben Tossell@bentossell · Makerpad.co
Hey Jason, What are your favourite questions to ask founders?
Shaun Trennery
Shaun Trennery@shauntrennery · Founder X&Go
The Launch conference is an incredible platform for new startups to begin their journey. Post launch, the most difficult challenge is revenue and sourcing customers. Have you considered creating a platform that will encourage corporates to list needs? Almost like your request for startup concept. Needs would be vetted and startups, who quality, can bid for the work. I can imagine Tesla posting an employee benefits need or Starbucks posting a facial recognition need.
@jason @eriktorenberg If you were invited to do Shark Tank, would you consider doing an episode?
Rustin Rassoli
Rustin Rassoli@rustinrassoli · 16 Year Old Founder & CEO, Greetale
Hey Jason! Thanks so much for taking the time to do this AMA, and congrats on Launch Festival! So excited to watch the live stream as unfortunately I won't be able to make it. What is your advice for young entrepreneurs still in high school? Thank you again, Rustin
alexandremayol@alexandremayol · DayPass: hotel pools & fitness on demand
hi @rustinrassoli , where do you get the streams from?
Rustin Rassoli
Rustin Rassoli@rustinrassoli · 16 Year Old Founder & CEO, Greetale
@jackdiver hey! I'm not really sure what you mean by that.
alexandremayol@alexandremayol · DayPass: hotel pools & fitness on demand
@rustinrassoli sorry not english native here, just to know where are the Launch Festival Live Streams
Rustin Rassoli
Rustin Rassoli@rustinrassoli · 16 Year Old Founder & CEO, Greetale
@jackdiver oh! I think it's streamed on YouTube. Here's the link:
alexandremayol@alexandremayol · DayPass: hotel pools & fitness on demand
@rustinrassoli thanks, I could have searched a bit more ;-)
Lily Yeh
Lily Yeh@lilyyeh · CEO and Founder, Little Loving Hands
HI Jason, Thank you for your time today! Been a follower of all your posts and blogs and all the great advice you've given in the past. Currently, I'm funding everything myself. I'm confident in my product and service which focuses on teaching kids empathy and the importance of giving back. We are a monthly subscription business that delivers craft projects allowing kids to create items that are sent back to charity and handed out to those in need. Given the smaller budget, I've done limited marketing. Is it crazy to think that I can grow this without outside investments that would allow a significant amount of dollars to be put into marketing to expand reach? I really appreciate any guidance you may have. Lily https://littlelovinghands.com
alexandremayol@alexandremayol · DayPass: hotel pools & fitness on demand
Hi Jason, Thanks for being here & for the inspiration. Can you tell us / show us (not sure if you can put an image here) what apps are on your Phone Home Screen?
Danielle Newnham
Danielle Newnham@daniellenewnham · Founder, The Junto Network. Author
Hi Jason - where does your hustle and drive stem from?
Lejla Bajgoric
Lejla Bajgoric@lejlahunts · Intern, Product Hunt
Is there something new you've recently developed an interest or passion for?
Hey @jason, what's the best way to reach you?
Soroush Ghodsi
Soroush Ghodsi@soroushg_ · Founder Slik.
What do you want your legacy to be?
Levent Aşkan
Levent Aşkan@leventask
Hi Jason, it's great to see you in here. I have two questions. The first is - what is your biggest regret in your entrepreneurship life? The second is - which time management/productivity programs you use to be more effective?
Brian Kennish
Brian Kennish@oldestlivingboy · @rocketship, @callblockapp, @adblockfast
Which companies were you the most excited about over the years, before they launched at Launch? Have there been any companies that surprised you by taking off after the show? How about any that surprised you by not taking off afterwards?
Adam Marx
Adam Marx@adammarx13 · Freelance writer/editor and music addict
Hey @Jason, firstly, thanks for taking time today! I'm curious about how you see the journalism universe changing in the next ten years. After doing Inside and others, what do you as a journalist find the most intriguing set of dynamics happening in news right now?
Ronald Huang
Ronald Huang@rawnerd_huang
How can I promote my site and improve the user traffic?