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Why I invested $250,000 in Swell

I thought you guys might be interested in hearing how I’m tackling the absurdly hard task of trying to pick winners as an angel investor. My goal in talking about my bets—uhhh, I mean investments—isn’t to promote myself or the startup, but rather get your insights into my process.

Also, writing is clarity of thought. If I set the benchmark that I’m going to write out my thinking on every investment I make, that should force me to think deeply about each one. Not that I don’t already do that, but there is something about the forcing function of writing that just works for me.

Swell is an App that my friend Josh from DFJ showed me at a poker game. When he handed me his phone and said ‘it’s Pandora for talk radio’ I got it immediately.

Get it -

Here are the signals that made write a check:

1. Trusted referral / respected early investors: my friend Josh showed me the product, and Google Ventures was also involved. I’ve got deep respect for Josh (early investor in Box), and for the GV team, which include my old friend Kevin Rose (who just did a fireside chat for the LAUNCH Hackathon: catch the podcast 12/10 - on Swell, too). I also have a bunch of other friends/people at those two firms including Tim Draper, Steve Jurvetson (who I had on the program recently, MG Siegler (who pisses off more people than me when he writes—always a good thing), Daniel Burka (who gave me solid advice on design) and Joe Kraus (who I always respected deeply on a product level).

2. Clarity of mission and a singular focus: Swell is doing something very simple, but very hard, getting people to the best talk radio out there. This could be a TED talk, a public radio show or a podcast.

3. My Knowledge of the Space: I’ve been podcasting for two decades, since before it was called podcasting in fact. I did the Silicon Alley Reporter radio show on Pseudo back in the ‘90s, CalacanisCast in 2007, This Week in Tech, Gillmor Gang and then This Week in Startups (just past 400 episodes!). I’ve done at least 600+ podcasts as a host or guest. The biggest problem in podcasting is discovery, as in getting the right people to your podcast. Apple has done some fine work in this space, but the fact is only 5% of the potential audience for Leo Laporte’s This Week in Tech actually know about the show—and he’s been doing it for almost a decade!

4. Stunning design and UX: Swell uses ‘cards’ as their user experience and it works brilliantly. Imagine playing cards on your phone in a stack that you can swipe through quickly and that’s how Swell works. Similar to Tinder, the dating app, but very different than a feed like Twitter and Facebook, where you scroll up and down a bunch of tiles (which you could call ‘cards’ but I won't for reasons of clarity).

5. Audible Addiction: I’ve been addicted to talk via podcasting for years, but before that I was a huge fan of a tiny startup in NJ called Audible. They eventually got bought by Amazon, and I’ve been a Platinum Subscriber for years. That means I spend ~$200 a year for 20 titles a year. I do this because I travel and drive a lot, and I feel like that time is wasted. If I listen to audiobooks I feel like I’m getting smarter and more worldly, whether it’s something in business, pop culture or a biography. I find myself splitting my time between Audible’s awesome titles and Swell’s excellent curation now. In fact, Swell helped me discover a bunch of new programs I didn’t know existed.

6. Great founder. When I met the founder I could tell he was capable of building a big, lasting company immediately because his concerns were around two important people in his ecosystem: the listeners and the content producers. Too often Silicon Valley companies are obsessed with the former and not the latter. Having been through a lot of struggles with Google, both the Search Group and YouTube, where I felt they were not supportive enough of me as a content producer, I found this refreshing and on point. Right now YouTubers feel like YouTube doesn’t care about them as much as they care about their own growth. I believe this is what will limit YouTube’s and Google’s future. Netflix, Amazon, Yahoo and AOL might have a small fraction of the usage of YouTube, but they care more for their creators.

Over time I think YouTube’s position will erode as someone like Twitter, Amazon or Yahoo makes a bold move to support the YouTube creators on a much deeper level. Swell has that potential for podcasters and talk products. Having a founder who groks this made me feel like their heart was in the right place.

7. TuneIn and Stitcher: I’m big fans of these other startups in the space, but I wasn’t able to invest in them (too late!). So, being able to bet on a new entrant who I think has the edge in the curation and interface space was a welcome opportunity for me.

8. I think I can be of service to the team: One of my big roles as an angel investor is helping with branding, marketing, positioning and product design—at least that’s what my fellow founders tell me. In this case, my domain expertise in talk radio as a creator and metaconsumer should help me act as a great resource to the founder.

There is a long way to go for Swell, but I’m really excited to be an early supporter. I think it’s a potential unicorn.

LAUNCH Fund is ~$9m in size, is ~8% invested and has eight investments.

Q1: What do you think of Swell?
Q2: What do you think of my investing signals?
Q3: What’s your big idea for Swell?
Q4: If Swell was offered as an AngelList Syndicate investment would you consider it? (accredited investors only can signup here:

best @jason

PS - LAUNCH Festival is in 80 days! Get a complimentary ‘builder’ ticket here, using the code LAUNCHTIME.  You can buy a conference pass, VIP pass or Super VIP (each has access to different events of note).

PPS - The LAUNCH Ticker is the easiest way to keep up with the technology industry. For $100 a year you can read the “daily briefing” my researchers create for me! It’s 12 hours of daily research in two short emails. Sign up here:

PPPS - In case you missed it we had Naval on This Week in Startups. It’s a fireside chat we did at the LAUNCH Hackathon (#2).

PPPPS - If you want to get updates on my podcast This Week in Startups sign up for the email here  

PPPPS - is in beta, signup here:


LAUNCH Hackathon Wrap-Up

Jason Calacanis with first-place winners, Ramen

LAUNCH Hackathon (November 8-10, The Metreon City View, San Francisco):

A big thank you to all who participated in the LAUNCH Hackathon this past weekend in San Francisco.  The projects we saw exceeded our expectations and we were inspired by your hard work and energy! With over 1600 registrants, $1.7M+ in prizes, and 2 days of nonstop coding, LAUNCH's second Hackathon was a big success!

See what people were saying about the LAUNCH Hackathon on Twitter all weekend long (#launchhack)

Photos from Fri, Nov. 8:
Photos from Sun, Nov. 10:

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Of the 147 submitted projects, the judging panel selected 5 winners, with $100k in investment prizes from The LAUNCH Fund, and more:

First Place
($40k optional investment prize from the LAUNCH Fund):

Project-funding site for software startups, with a focus on early adopters, and collaborations.
Technology: Heroku, Ruby on Rails | @ramenapp
LAUNCH Hackathon project page:

Second Place - TIE
($20k optional investment prize each, from the LAUNCH Fund):

Mobile app to find restaurant pop-ups and underground dining experiences
Technology: Amazon AWS, Amazon EC2, Amazon S3, CSS, HTML5, JavaScript, MongoDB, Node.js, Objective C, Redis | @prixfixeapp
LAUNCH Hackathon project page:

Modular software to control robotic gantry for scientific experiments: recording and executing automation routines, live camera feed, gesture-based control
Technology: Arduino, Bootstrap
LAUNCH Hackathon project page:

Fourth Place
($10k optional investment prize from the LAUNCH Fund):

Code review for design projects; improving workflow for designers, developers and project managers
Technology: Angular.js, Dropbox API, JavaScript, Python, Twilio
LAUNCH Hackathon project page:


Fifth Place
($10k optional investment prize):

Mobile app that allows users to choose clothes they like, push designs into production , and earn rewards for being trendsetters – first access to fashion

Technology: iOS, Kohl’s API, Parse
LAUNCH  Hackathon project page:

See all 147 projects here:



The 15 finalists were:

Ramen (1st place winners)
AutoBio (2nd place winners - tied)
PrixFixe (2nd place winners - tied)
FinalRev (4th place)
Vibrance (5th place)
Meeting Pulse
Under the Radar
Kohl's Scavenger Hunt

Congratulations to all 15 finalists!

Click to read more ...


#googlewinseverything (part 1)


1. No company has as many smart people as Google.

2. No company is as ambitious as Google.

3. No company is working on as many hard problems as Google.

4. No company makes as many big bets as Google.

5. No company is willing to make as many crazy acquisitions as Google.

6. No company has more data than Google.

7. Few companies understand how to play the government better than Google.

8. No company has more global influence than Google.

9. No company is as ruthlessly efficient as Google.

10. Only one CEO is more ambitious than Google’s Larry Page.*

Google is going to win everything.




In truth, the 10 ‘facts’ I’ve outlined above are not mine; these are the opinions I’ve collected over the past year asking intelligent folks, ‘So what do you think about Google?’

These are the “facts” as the people see them. Although, I haven’t found anyone who disagrees with these 10 facts – do you?

The executives in technology, media, finance, journalism and government that I spend time with – typically at poker, dinner or bottle-service tables – have formed the general consensus above.

These brilliant degenerates I gamble, break bread and pop bottles with are more connected and intelligent than any of us – certainly me.

[ Side note: How great is my life that the kid with the 71 four-year average from Brooklyn gets to hang with the smartest kids in the class!? Love it! ]

They’re in awe of Google’s performance since Larry Page took over.

They’ve never seen anything like it in the history of not only technology, but humanity.

In this piece, I’m going to explore the following:

a) What are Google’s most ambitious projects?
b) What our world will look like in 10 and 20 years if Page & Co. execute at (just) their current level
c) What the ramifications are for startups, investors, the media, journalism, government, education, privacy, freedom and humanity

Click to read more ...


New Hackathon Keynote Speaker added: Naval Ravikant!


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We’re excited to announce that AngelList Founder and CEO @Naval Ravikant will join us at the LAUNCH Hackathon (Nov 8-10, San Francisco).  On the final day of coding, Naval and @Jason Calacanis will take to main stage for what’s sure to be an inspiring conversation!  See their previous “This Week in Startups” interview:

The Hackathon will open with a fireside conversation between @Jason and Kevin Rose (Digg, Google Ventures), and is poised to be the largest hackathon in the world with over 1k developers and designers competing for $1.7M+ in investment prizes.  

Spots are going quickly – there are only about 200 left – so register your team now!  All applicants will be screened, but participation is completely free, and includes breakfast, lunch, massages, workshops, and more.  

Learn more and reserve your team’s spot:



The Value of Starting from Zero (Divergent Thinking FTW)


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Yesterday I met with a savvy founder working on her first startup. She was looking for feedback and, of course wanted to mention that they happened to be closing out their angel round – there *might* be a little room left for me.

In all meetings, I like to get to the product as quickly as possible, so I asked:

“Can you show me your product?”  I’m a sucker for good product.

The founder proceeded to show me a site that looked exactly like Pinterest, but that was focused on a single vertical (which I will leave out).

“Pinterest clone!” was my immediate thought.

As the product was only 70% as refined as Pinterest, I quickly moved on:

“Uninspired founder!”

… and “Poor executer!”

At that point the meeting was basically over in my mind. Why?  

a) the projects and people I tend to invest in are ‘starting from zero’ and building up, and b) I only invest in folks who can build products that are as good or better than what’s in the market.

The LAUNCH Fund’s investments all have wickedly designed products:, and (and hey, two of three have .io domains – hmmmm).

These are my biases, and they’re largely based on my own reflection of when I’ve done great work and when I’ve done ‘menza menza’ work.

The Save
Interestingly, in the last five minutes I asked the founder why she wanted to build this product and she got a huge save. She explained her personal frustration trying to solve a problem in her life: the granular details of the problem and the potential solutions she tried after talking to her friends.

Click to read more ...

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