A catch phrase will go here soon.

An update on my angel investing & AngelList Syndicates


Angel investing is a brutally hard job …

… said no one ever!

[ 1,600 words on the topic below. Click to tweet: http://ctt.ec/_G49d ]

I’m absolutely loving being an angel investor. It’s a blast to meet smart folks with killer ideas who want to change the world — and then I get to write a check and give one out of every 250 of those ideas a try!

In the past year I’ve invested $1.95m in 30 startups from the LAUNCH Fund (from my $10m angel fund). We are now 19.5% invested in 13.5 months. We’ll invest another $4.05m in the next 24 months for a total of $6M/60% invested, keeping back the last $4m to keep our pro rata in the winners.

I’m told this is a savvy plan by my much, much savvier friends.

You may remember that I wrote a blog post 6 months ago about how excited I was to invest in Swell. [http://goo.gl/wwdEGL] Recently there were some reports in the news about Swell and that technology company we all love soooooo much in Cupertino. [ http://goo.gl/nlyYqE]

A company which, I might add, is performing at an absurdly high-level while evolving their strategy ( <—- shameless suck up).

Anyway, we got a “quick win” for my fund and I’m super happy for the founders of Swell. Great things to come from Apple+Swell combo I’m certain.

Syndicate Power

During the past four months we syndicated nine of the LAUNCH Fund’s deals to our AngelList Syndicate for a total of $3.18m invested. In those deals the LAUNCH Fund did a total of $550k, while the Syndicate came in for 4.78 times that amount for $2.63m.

Our average Syndicated deal was $353k, with $61k on average coming from the LAUNCH Fund and $292k come from our Syndicates.

Two out of nine deals are closing as I write this, so that $2.63m will be slightly higher if we continue to be vastly oversubscribed.

The LAUNCH Fund will do three deals a month and ~30 a year. If we syndicate 20 of those deals, we are on pace to put $7.67m a year to work.

This is the revolution and no one in the mainstream press seems to have caught on yet  (despite me telling them: “hey, you might want to look over here … something is brewing.”).

A couple of years ago my level of angel investing would be significant on a number-of-deals basis (two or three per month), but not very important or significant on a dollar basis.


Well, I’m able to lead a round of funding, set the price with the founder, and perhaps even take a board seat. (In most cases we get the option of a board seat, even though I really don’t have the time to sit on that many boards.)

Bottom line: when I wrote about AngelList 11 months ago, and said a bunch of ‘outlandish’ things [http://goo.gl/N7cDa8]; this was all very speculative. Most folks thought that AngelList wouldn’t be able to attract real fund managers, and that those fund managers wouldn’t be able to get access to A+ deals.

Those questions have been answered, and folks like Gil Penchina (serious angel), and Tim Ferriss (serious thinker, author and personality, and developing into a VERY SERIOUS angel investor), have proven that they can bring real deal flow to the platform.

What AngelList Syndicates has done for me most of all is to make me more helpful to founders. Instead of having to manage another dozen angels, they can just manage a relationship with me. Not only that, they get 99 folks on their team who have a literal, vested interest in their success (the members of the Syndicate).

That’s 100 folks for one mention on your cap table. One hundred affluent and connected folks who might tweet out a job posting, or hopefully refer someone to you. Or intro you to a partner or possible client. Or another investor. It’s a big deal.

Moreover, AngelList has given many ‘civilians’ (folks who don’t typically have access to these types of deals), the ability to put $1,000 to $10,000 into deals they would never even hear about until they were well-funded.

There is no guarantee of success, but this is a huge step in the right direction.

99 Limit Throttles Everything

The crazy thing about the massive performance to date of syndicates, is that it has all been done even though only 99 people can invest in a syndicate. This is an SEC limit, I believe intended to protect the rich (only accredited investors can participate in this type of deal flow), in some aggregate way.

Brad Feld talks about it here: http://goo.gl/xNqt7Z

I get that the SEC wants to throttle the potential fallout from a deal going belly up, but the entire point of angel investing — at least the way I do it — is for 7 out of 10 deals to go belly up! We want deals that are so risky that there’s only a 1-5% chance that the startup will have an absurdly big outcome.

For example, if you invest in 50 quality Silicon Valley startups (real deal flow, not second- or third-tier deal flow) you might have 30-40 return little to nothing. Big zero.

You might have 10-15 return a small amount and have one or two have 50x+ outcomes — with the lottery ticket chance that you catch a unicorn like Facebook, Uber, Twitter, Airbnb, Dropbox or Box that could return 100-3,000x.

[ Lottery ticket is the key phrase in that paragraph above. Expect one in every three or four lifetimes. ]

In truth, 500 folks investing $1,000 each is safer than 100 folks investing $5,000 each. For me, well, I think people should be able to invest and spend their hard-earned money however they want. I don’t think there should be a category of “accredited investors” vs. “non.” I think that is actually a very class-based system where the rich get richer and the “poor schlubs” (as which I spent 80% of my life being classified) need to be protected from investing in the next Facebook or Twitter.

Poor folk should be allowed to place a $1,000 bet on LinkedIn or Facebook if they think it’s the next big thing — just like they can place it on a roulette wheel in Vegas.

That being said, the 99 limit should be something like 500 so that we can keep the American economy moving. Rich people are simply NOT investing their money, and getting them to take it out of bonds, second homes, and JetSuite memberships — and into angel investing — is critical to our sustained growth as a nation.

Other countries have fewer rules and they will benefit from them. Let’s stop trying to protect the rich from investing their money in startups, and start trying to build more startups — because startups create jobs. Most of them, in fact.

Should you Angel Invest?

I get this question a lot. As far as I’m concerned if you keep angel investing down to 1-5% of your net worth, well, you’ve controlled the risk.

If you put that modest percentage to work in 50 deals, that means, in the most aggressive 5% model, each investment is 10 basis points of your net worth. If you were worth $5m in this example, 5% of your net worth would be $250k. In 50 deals that’s $5k per deal. If you did 2.5% of your net worth, it would be $2,500 in 50 deals.

Well, that’s sort of the sweet spot for angel investing through a syndicate on AngelList, or some of the emerging competitors. That list includes MicroVentures, Crowdfounder, FundersClub, and CircleUp, among a growing list of options.

Again, if you are not an “accredited investor” as defined by the government then you’re too simple or too irresponsible, I guess, to invest your own hard-earned money. #sarcasm

More to Come

I’m going to keep updating folks on my education as an angel investor and Syndicate. I’m in a unique station in life, in that I’ve put 25 years into being a journalist and entrepreneur in technology, so I’ve got a heck of a network and a ton of experience.

It’s making angel investing really pleasurable so far, but of course in a market this hot everyone looks like a genius. I’ve been through two brutal, brutal tech corrections in my career and I’m guessing there will be a third some day — perhaps in the middle of my first fund.

I can’t control that, but I can control the checks I write, and I’m writing them based on big, crazy ideas by passionate people who are executing at a very high level.

If that’s you, well, you know how to find me (and if you watch This Week in Startups, you’ll know what impresses me).

best @jason

P.S. – If you want to join the Syndicate, angel.co/jason

P.P.S. – This Week in Startups is my podcast: www.thisweekinstartups.com

P.P.P.S. – The LAUNCH Festival is March 2-4 at Fort Mason. 12,000 folks will be there, save the date.

P.P.P.P.S. – LAUNCH Scale is an intimate event taking place on October 23-24, more at LAUNCHSCALE.NET & read: Startups are about Scale [http://goo.gl/jhUC16]

Startups are about SCALE


Startups today are about one thing: scale.

As in getting big and doing it fast, like: Uber, Airbnb, Dropbox, Snapchat and a couple dozen others.

In this post I want to accomplish two things:

1. Explain why SCALE is so critical today.
2. Get ideas from you on topics and speakers for the LAUNCH SCALE event I’m hosting.

[ LAUNCH SCALE: Oct 23-24, San Francisco -- http://events.launch.co/scale ]

“But wait Jason,” I can hear one of you tweeting me, “didn’t you say just two years ago that we are living in the ‘age of excellence’ and all that matters is how good the product is?” [The Age of Excellence: http://blog.launch.co/blog/the-age-of-excellence.html ]

That was 27 months ago. Things have changed radically in that time, and what has changed most is that “startup alchemy” has given way to “startup science.” If you look at all the aspects of building your company, it has become productized:

– We have MailChimp teaching us — heck, forcing us — to do email perfectly. Ten years ago we had to spend entire days per month sending emails. Now it’s minutes.

– Amazon Web Services, Dyn, and Rackspace are letting folks build their infrastructure perfectly and quickly. Years ago it tooks months to get your stack up and running.

– InVision is letting us build flawless mock-ups, and HipChat is letting us communicate 24/7 across mobile and desktops.

– Marketing is as easy to implement as buying books from Amazon was ten years ago. Non-technical folks can launch campaigns on Twitter and Facebook’s marketplaces in hours, without ever needing to hire an agency. With AdStage it gets even easier.

– You can go on Dribbble or Behance and sort and surf through killer designs — made by people in South America, Asia, and Eastern Europe — that are indistinguishable from folks in the United States!

– Finally, the accelerators are filling in a ton of the gaps in building your product.

What’s left if every aspect of a startup is being perfected and productized?


The Questions to Ask Yourself

Given a year or so of capital/time you should be able to build a solid product that some group of users find value in. If you can’t, there are two reasons:

1. You’re probably trying to do something wildly complex or far out there in terms of even being possible (think an electric car, artificial intelligence).

2. You suck and shouldn’t be an entrepreneur.

If your problem is #1, well, then just pivot to the “next best manifestation of your vision based on what you learned.”

If your problem is #2, simply go work for someone brilliant for two to five years and take a LOT OF NOTES.

If you have built a great product, but it’s not growing, ask yourself the following:

I. “How much time and money are we spending in total as a company each month?”
II. “How much of that time and money is going directly toward the growth of this product?”
III. “Is our team aligned around the goal of growth or not?”

In my case, I told our team that we would build Inside.com to the point of having a core group of thousands of daily users who love the app, and if we succeeded then we would focus on growth.

We are in the process of looking at our budgets and time, and literally putting as much behind the SCALE of our product as we can.

There are two primary growth types:

a) Adding new users
b) Getting existing users to use your product more

So we are pursuing both of these with content, social, targeted ads, PR, and most importantly, product design.

It’s HARD to make a news product viral, but we’re trying!

Help Me Help You!

Now that I’m in the middle of trying to SCALE Inside.com, it’s the perfect time for me to bring 250 of y’all to learn together.

That’s LAUNCH SCALE, and I could use your help with the following:

– Speakers: We are looking for executives who specialize in growing startups, and have had great success in doing so. Think backwards from high-growth startups (Uber, Airbnb, Box, Dropbox, etc.), as well as from the function areas (PR, viral loops, UX, paid, social, street teams, community, content marketing, etc.).

– Join us: You can buy a ticket with the 30% FOJ discount code (“friend of Jason”) that is good for the next week.

– Diversity: All of our events, in addition to my podcast and investing, are working hard to present tremendous diversity on the stage and in the audience. Our team believes that our events and products benefit greatly from lots of different perspectives. With that in mind, please help us find speakers and submit them here: http://events.launch.co/speakerformscale. Also, if you know of anyone who would benefit from a scholarship, we reserve 10% of our seating for folks striving to take it to the next level (like many of us did in web 1.0!).

– Sponsor: We are doing two types of presentations at LAUNCH SCALE:
1. Startups that have scaled
2. Companies that provide tools that help startups scale. So if you are a company that makes money providing tools for companies to grow, well, you should sponsor the event and show your product/case study. Email partners@launch.co

We have the following presentations already lined up:

1. Steve Huffman, Co-Founder – reddit & Hipmunk
2. Marco Zappacosta, CEO – Thumbtack will explain how thumbtack got 70,000 paying customers without a salesforce, and raised $50M.
3. Andrew Johns, Head of Growth & Revenue – Wealthfront will talk about how they attracted $1B in assets under management with a tiny marketing budget.
4. Patrick Cheeseman, Head of Customer Experience – HotelTonight will discuss how to use support to drive product innovation.
5. Ryan Mannion, CTO – POLITICO will discuss how to grow from 0 to 100 Million monthly pageviews.
6. Christopher DePatria, VP of Revenue – SignPost will explain how he grew their sales team from 5 to 100 in 2 years, and signed up 93k SMB customers.
7. Aaron Magness, VP of Marketing – Betabrand will tell us how they use crowd-funded emails to never have unwanted inventory again.
8. Craig Zingerline, Sr. Director of Product – Red Tricycle will tell us how they grew to 750,000 emails without spending a dollar.
9. Arjun Naskar, Growth Manager – Homejoy will discuss how to expand into 31 markets in 2 years.


BRD’s slick electric motorcycles


Think electric motorcycles don’t sound badass? Definitely don’t tell Harley-Davidson; they’re testing one. And definitely don’t watch the video of BRD Motorcycles street racer in action. Founder Marc Fenigstein won’t tell us what the company name stands for, but it’s clearly all about speed, maneuverability and performance. Yes, electric vehicles are getting sexy.

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LAUNCH Beacon – Retail, location, & payment summit (June 16, NYC)


Every couple of years, folks like me say retail is dead, and the stats on malls seem to be proving that out — with 15% estimated to close in the next 10 years. The stunning pictures of malls in transition, including this strip mall parking lot converted to an urban farm, are the stuff of science fiction. Dystopian rebirth –– the street finding its own use for the past.

Yet we’re all still shopping like crazy. People still like to go out of their houses, despite the hype around the Oculus Rift that Zuck just bought for 1.3% of their stock.

As much as I love to set up “subscribe and save” on Amazon Prime, never having to think about coffee beans, soap and razors, I still like to get out of the house and take my four-year-old daughter somewhere on the weekends.

Folks are being pulled from their homes by the lure of 4D movie theaters in Los Angeles, open spaces like Tony Hsieh’s container park in downtown Vegas, and digital storefronts in shopping malls.

Retail, local and payments are all in massive transition.

When I sense something like this, I do two things:

1. Start writing checks as an angel investor
2. Hold a conference: www.launchbeacon.co

With regard to number one, I’ve invested in seven local-ish plays to date (about 10% of my investments): Gowalla.com (sold to Facebook), Signpost.com (software for local businesses), MyTime.com (book any appointment), Thumbtack.com (find a service provider, like I just did for tennis), Uber.com (urban logistics, not just cabs now that they launched Uber Rush in NYC), Red Tricycle (what to do with your kids(redtri.com) and StyleSeat.com (software/services for salons and such). Links to each of these founders on This Week in Startups at the bottom of this announcement.

With regard to the conference, on June 16, I will host a one-day event in New York City (I’m coming home!) at the Metropolitan Pavilion on W. 18th Street (where I used to host Silicon Alley 99, 2000, etc).

Simple agenda: I will do demos with 10 startups that we hand select for awesomeness (not my investments FYI), two keynote/fireside chats and four partner presentations (keeping the lights on baby!). Then we will have an intimate dinner for 150.

This is a tiny event, but we hope it has great density of people who care about these issues.

How to be involved:

a) If you want to attend you can buy a ticket here: http://goo.gl/8g5h4S
b) If you work at a retailer in transition please ping us for an invite & feedback at contact@launch.co
c) If you want to speak at the event you can apply here: http://goo.gl/0s5aQI
d) If you are broke and a founder/technologist with passion, we have 15 scholarships available for pre-funding startups: http://goo.gl/3Zsa3v
e) If you want to help keep the lights on and be one of the four presenting partners email partners@launch.co
f) If you are working press — on assignment covering the event — apply here: http://goo.gl/ePjsDn
g) We will not be live streaming the event, but some content will be released as This Week in Startups episodes: www.thisweekinstartups.com

Thanks to my friends at Pivotal Labs for partnering with me on this awesome event.

best @Jason Calacanis & the LAUNCH team

Related founders on the show:
Gowalla 12/3/2010: http://youtu.be/SGVp7XoYRaU
Dwolla 9/17/2013: http://youtu.be/BFeSgN1cQhg
Uber (1) 8/16/2011: http://youtu.be/550X5OZVk7Y
Uber (2) 3/4/2014: http://youtu.be/u_Baur8sT_8
StyleSeat: not yet, but we’re booking Melody soon!

Disney to acquire Maker Studios? IPO watch & LAUNCH of the Week | This Week in Startups


Disney is in talks to acquire Maker Studios for $500m, according to Recode’s Peter Kafka. The entertainment giant’s recent acquisitions focused on IP: Marvel, Lucasfilm. Maker represents YouTube stars like PewDiePie and iJustine, which could dovetail nicely with Disney’s youth-focused TV programming. For Maker and its investors, the time is ripe for sale, with so much traffic reliant on YouTube and little distribution of its own outside of Google.

It’s going to be a big year for tech IPOs. Add to the list of companies expected to start public trading: Eventbrite, King Games (maker of Candy Crush), and China’s multibillion internet giant Alibaba, which could raise $15B. That will also be a big boon to Yahoo which has ~20% stake.

Bing LAUNCH of the Week: Imitone software turns your humming into electronic music, a Boston hospital built a Google Glass app to read patient data through QR codes, and Omaze wants to raise money by raffling off experiences with celebrities. This week: enter to win time with Arnold Schwarzenegger, crushing stuff in his tank.

Plus, are diversity problems specific to journalism and tech? And how valuable is the SXSW conference for techies?

Sarah Lacy of Pando Daily and Rafe Needleman of Yahoo Tech sat down with me for the This Week in Startups news roundtable.

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5:06 – Disney might acquire Maker Studios.
6:05 – RN: It shows how media is shifting. Smart move for Disney; I’m glad to see them do it. It’s great for independent media producers as well. A new outlet. You don’t have to be a major studio to build a major following.
7:10 – JC: Am I cynical to think this might be investors leaking?
7:25 – SL: If it were someone other than Kafka, I’d say maybe, but I think it’s just really good intel. It would be a good play for LA, Mark Suster. Machinima. I always like to see companies go long but this is a rare time where I think is great
8:36 – JC: Machinima laying of 25% of staff. When it comes to video, only one ecosystem at scale. When you build inside someone else’s ecosystem, there’s a conflict when that system decides that they want your business.
9:15 – SL: but what does it mean for Disney? They don’t have a great track record of buying tech companies. Is this where Maker goes to die?
9:32 – JC: I bet this is a deal for Disney where they want to learn a little. iJustine, etc. feels a lot like the Disney Channel, but if they learned how to create the next new star, it would probably be worth it. They’re interesting – they don’t seem to buy tech startups and build great stuff w/ 3rd parties, based on their original IP…Star Wars, Marvel, etc.
11:00 – SL: well Sheryl Sandberg is on their board and Facebook is buying up a ton.
11:38 – Thank you @Mailchimp for supporting the show!
13:35 – IPOs galore: now Eventbrite, King Games, Alibaba.
14:42 – SL: Why would anyone buy King in an IPO? They’re candy – you fly through them and then get bored of them.
15:54 – JC: why can’t someone put together a string of hits in the way that Disney et. al can create multiple hits?
16:15 – SL: Disney was born in a different era. They’ll always have that back catalog.
17:15 – RN: I don’t know what the secret sauce is, but when you upset the applecart, bad things happen. Draw Something, Zynga. Rovio has been able to exploit their catalog of characters and ideas. It works on XBox and Playstation games but on mobile games…when it collapses….stock is almost worthless
18:32 – JC: no one has played a casual mobile gaming company. Angry Birds, etc.
XX:XX – SL: …at some point, there are laws of gravity.
19:27 – JC: Eventbrite
1938 – SL: Eventbrite is an uninspiring IPO. It’s not a company I get super excited about. We use it all the time… it’s doing well but missed the boat to what it could be.
20:34 – RN: They’re building on the planning and building space. If they can successfully [do discovery], there’s value. It’s not sexy, but there’s value.
21:35 – JC: map tickets to your seats. You can actually make reserved seats in your auditorium. We’ve used Ticketleap, but to sell specific seats is disruptive.
22:22 – JC: Alibaba
24:00 – RN: I love Alibaba. Considering that I work here, that’s all I can say.
24:19 – JC: It must make everyone at Yahoo! feel a sense of security.
24:35 – SL: I did a show for Yahoo! Finance a few years ago, and I have to say, if you have worked in traditional journalism, it is a plush, great job.
25:05 – RN: I will say that I have never worked as many hours in my life.
25:20 – Thank you @ScottEdWalker for supporting entrepreneurs and the show!
XX: XX – Launch of the Week
XX:XX – Glass app for Boston doctors
28:22 – Imitone – turn your humming into song
29:00 – Omaze.
30:35 – JC: favorites?
31:02 – RN: As a business, the one that touches money is probably best. However, the latter two don’t excite me at all. The glass app may help save lives and help doctors do good work. Socially acceptable context. This is where this tech lives. I love that and if it could make doctors better, that’s the one I like.
31:50 – JC: Glass sucks for consumers but good for enterprise?
32:00 – RN: SXSW panels about how not to be a Glasshole. I want to punch people in the face when I talk to them trying to talk me.
32:25 – JC: Woman at bar. Everyone I know doesn’t want you talk to talk to them with it.
33:00 – RN: If I’m nearly dead, that’s what I want.
33:15 – SL: How does it make it any better? I think doctors aren’t going to do it.
33:35 – JC: I could see if you’re doing surgery, if you could see the metrics, that would be useful.
34:55 – JC: I told you that people were going to be punched in the face for wearing glass. I told a glass exec that he was killing the vibe on the dance floor.
36:05 – JC favorites?
36:40 – SL: I’m going to say Imitone. It’s not super exciting but I think the doctor thing is ridiculous – a gimmick no one will adopt. Omaze is interesting but any business that is predicated on celebrities is hard to sustain.
37:35 – JC: The glass app, as presented, is meaningless. Pick up the damn chart. An iPad would probably be better. I see the potential, but not in current application. I think Imitone could inspire people to pick up an instrument, but I hate music startups, they don’t go anywhere. But Omaze – there’s something there with crowdfunding and people love raffles. There you have it, first split decision.
39:08 – JC: Whistleblowers at SXSW. Everyone knows I hate panels: nothing occurs on them. I’m never going again. Boondoggle. They did have 3 pretty good keynotes: Lady Gaga, Snowden, Assange. The sad thing: auto accident.
40:55 – RN: The car event was a terrible tragedy. As far as overall, I was there 4 days, but I didn’t go to a single panel. Great event for Yahoo! The people who are there to meet other people and to party and learn, it’s a great event. If you can afford it, I love going.
42:19 – JC: SXSW so huge and spilling into streets, any connection to be made to the tragedy?
42:30 – SL: No, no connection. This is the first highly violent thing we’ve seen at SXSW. This is a bunch of drunk people. I’m glad that we haven’t seen this earlier. I hate the conference. This event has nothing to do w/ why it’s awful… it’s a good conference for people under the director level, and for people who want to be entrepreneurs. Mid-level people in the career to go make contacts. I would never go, it’s awful.
43:55 – RN: People could say that if you want to stay up with what’s happening there, go to SXSW.
45:45 – SL: I’ve seen more cool and up and coming stuff at Jason’s conference than I’ve ever heard at SxSW. Talking about privacy, etc., good for them. I don’t hear about any good companies. Up and comers are working their asses off, building shit. Not paying $600 / night. There’s huge business done at CES.
46:45 – JC: I go to CES for 48 hours, to go to one dinner.
47:20 – RL: You guys are elitist.
47:36 – JC: Guardian decries lack of diversity in journalism startups.
48:40 – SL: Diversity problem in any industry. This is reality, let’s stop being shocked by it. The point is that she’s complaining about it, but ignoring some of the bigger one. People expect better of Emily Bell. Not well thought-out.
50:40 – RN: Without running the numbers, I don’t think diversity has changed much, but not substantially greater number than when I started.
51:40 – JC: Do female founders hire more females?
51:54 – SL: Talent is talent. I don’t put extra care into hiring, but I do spend extra time mentoring. I wish we had more racial diversity. The biggest problem for us is that we’re all white.
52:37 – SL: [biggest hurdle] – if you get a scoop and someone doesn’t, people say “you got it because you’re a girl.” I think it’s hard if you’re a single girl. How do you date as a tech journalist in SF?
53:35 – JC: People disclose who they’re married to. What’s the best practice for dating?
53:50 – SL: yeah, where’s the line on this? Recusing yourself out of fashion. Making sure you’re not getting used, etc. It’s a harder world. I think it’s harder for women. Because it’s what your haters will say about you.
55:10 – JC: There’s a violence against women that’s not expressed toward men.
55:20 – SL: People are more likely to assume a woman is stupid and doesn’t know what she’s talking about.
56:00 – JC: Any rule about dating and reporting?
46:19 – Rafe close: Follow @rafe. http://Yahoo.com/tech! David Pogue’s reviews here. Send your mom to Yahoo.com/tech
58:22 – JC: Follow @sarahcuda. Feisty.
59:00 – JC: Be thoughtful. Don’t be cavalier with certain words.

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Techbrats Goldberg, Shih and Gopman Do Not Represent Technology


In 20 or 30 years, what will we look back on and say “That was the issue of our time?”

I ask hyper-intelligent people this question from time to time, and the answers are frequently similar: environment, equality, employment and wage disparity are common.

I believe employment and wage disparity are the critical issues of our time.

Nowhere can this be seen more clearly and glaringly than in San Francisco. Rents in the city have skyrocketed and social unrest between the haves and have-nots has reached a boiling point. (Most recently, we saw protesters throwing a rock through the window of one of Google’s luxurious private buses.)

It’s hard for people not to hate technologists when faced with the absolute loathsomeness of three now-infamous industry executives: Peter Shih, Greg Gopman and Bryan Goldberg.

In three separate blog posts over the past year, these spoiled techbrats have shown the absolute worst qualities of the elite: a lack of empathy and class, combined with horrible entitlement — and the absolute inability to write.

Peter Shih, a startup founder, wrote that San Francisco is a city with a “pathetic excuse for a public transportation system,” where ‘I pay 80% of my salary to live down the street from crackheads and meth addicts” and which is home to “some of the craziest homeless people I have ever seen in my life” (his solution: “just hand them a handle of vodka and a pack of cigarettes, it’ll save everyone some trouble.”)

Link: http://goo.gl/nT5yJC

His bile was followed by Gopman’s post which claimed:

“The difference [between SF and elsewhere] is in other cosmopolitan cities, the lower part of society keep to themselves. They sell small trinkets, beg coyly, stay quiet, and generally stay out of your way. They realize it’s a privilege to be in the civilized part of town and view themselves as guests. And that’s okay…

You can preach compassion, equality, and be the biggest lover in the world, but there is an area of town for degenerates and an area of town for the working class. There is nothing positive gained from having them so close to us. It’s a burden and a liability having them so close to us. Believe me, if they added the smallest iota of value I’d consider thinking different…”

Link: http://goo.gl/kEHAcj

Not to be outdone, millionaire Goldberg — the most successful of all these executives, having sold the widely-regarded-as-spam site Bleacher Report — did a ‘satirical piece’ that showed a complete lack of awareness, intelligence or ability to compose satire. Salon dubbed it “rock bottom” in “tech’s culture war.”

Link: http://goo.gl/j18NDq

Where to begin.

First, all three of these executives should be thankful they were born in a time when the ability to write code and understand technology was so absurdly rewarded as compared to the other crucial work of the world. Important things like teaching children to be productive citizens, running into burning buildings, protecting citizens from crime, doing CPR on people in cardiac arrest, and going to war and risking having your legs blown off by an IED.

In another age, say one where the ability to use a sword was the most in demand skill, these specimens wouldn’t have had the resolve to make it out of adolescence alive.

Second, if you are lucky enough to be absurdly rewarded as compared to the rest of society, a solid default position is to shut up and enjoy your epic rewards — not to taunt and abuse those less fortunate than yourself.

Third, if you have been delightfully rewarded for building websites — websites!!! — as opposed to digging ditches 10 hours a day, six days a week, perhaps you should look at those less fortunate than yourself with compassion and — gasp! — do something to help them?

Fourth, if your ability to write tops out at the Christmas card level, perhaps it would be wise for you to hone your skills before tackling the most sensitive and pressing issues of our time?

As my Tae Kwon Do teacher told me in me in my developing years, when I was prone to speak first and think second, “an empty can makes the most noise.”

These noisy individuals do not represent the technology industry within which I’ve built my career. No, the technologists of true success and merit develop and execute strategies to make society more just, fair and joyful for all.

Bill Gates gave up three or four delightful decades of working on building one of the great technology empires of all time to do things like eradicate malaria, provide clean drinking water and reinvent the condom so people would use them more often.

Mark Cuban dedicates his time to investing in startups that will never return even a small fraction of his wealth, while silently helping wounded soldiers and the poor (the details of which are largely unreported).

Elon Musk risked his entire fortune — and pushed himself personally to the brink — to get us off carbon and he’s still driving himself at an inhuman pace to “back up Earth” on another planet. (I’ve encouraged him to pace himself many times, but it’s just not how he is wired.)

Jeff Skoll has produced media — at great loss and risk at times — in order to expand people’s consciousness about important issues. Fast Food Nation, An Inconvenient Truth, Food Inc, Darfur Now, and his new TV network, Pivot, which aims to package up serious issues for millennials.

The list of technologists doing great things for humanity is endless, but the media is obsessing over these pathetic, visionless grandstanders– and I don’t blame them. This level of stupidity and vileness is editorial manna from above. How could the media not focus in on it?

A society can best be judged by how the most privileged regard and treat the most vulnerable and weak.

I have a challenge for these three individuals: invest in HandUp, a wonderful startup trying to actually help the homeless and distraught individuals in San francisco (and eventually beyond, I’m sure). If you each invest $10,000 in Handup I will match each of you. (Note: I’m already an investor, having invested on the spot during my talk with Rose: http://youtu.be/h9PSGHg2Vl0).

more: http://angel.co/handup

[ Sidenote: It’s a B (as in ‘benefit)’ corporation similar to stuff like Tom’s Shoes or Ben & Jerry’s, which aims to build a sustainable business by making a platform to help organizations focused on the homeless and poor. It’s “kickstarter for the homeless” and I say that with pride, not as a joke. Note: any profit I make from this investment I will donate to the homeless. ]

It takes only a cursory amount of reading — start with the mayor’s offices multiyear study on the cities ~6,000 homeless — to understand that a large percentage of the homeless are suffering from depression, mental illness, substance abuse and/or the elimination of their jobs.

And keep in mind that the “disruption” that is so lauded in our industry is largely one that removes inefficiencies, frequently defined as a “humans” working in “jobs.”

I’d argue that society’s issues around job loss are largely attributable to the massive change brought on by the technology we are building, and the wealth we are creating for a small subset of society.

This fact is indisputable and I believe it puts the responsibility for the weakest in our society on us — the technologists and investors — who not by happenstance are benefiting from this change.

On a strictly pragmatic basis, if you’re rich and privileged in our violently changing society, ask yourself if the last couple of bitcoins or homes you own are worth having a brick thrown through the window of bus you’re riding on.

It is completely possible that in the next 10 years, the streets of San Francisco and Manhattan will be filled with riots and protests by disenfranchised individuals–oh wait, that was the last three years: http://youtu.be/8yXSC0U9M6c

What is the point of this ever expanding “long boom” if we leave so many behind?

What a shallow victory we will have wrought if so many suffer so greatly while we benefit so exorbitantly.

all the best, @jason


PS – Sorry to have not written the followup piece to #googlewinseverything, but I felt that this piece needed to come now–before another ‘techbro’ decides the world needs to know how stupid and insensitive they are. Second, I’m on deadline for the Jan. 23rd launch of www.inside.com, as well as the LAUNCH Hackathon (Feb 21-23) & LAUNCH Festival on Feb. 24-26th (http://festival.launch.co).

PPS – If I get a moment I’ll follow up on this piece by expanding the final two points–or perhaps someone with the ability to write like @paulcarr, @lons, @jasonpontin, @karaswisher, @hblodget, etc. could take on these two concepts:

a) What responsibility does the Tech Industry specifically have to the people it has made redundant?

b) Wouldn’t it be a better world for everyone if we used just a small portion of the massive profits being made to ensure that everyone had a place to live and eat, so our cities weren’t overrun with poverty, hunger and desperation, making American cities like Los Angeles essentially Third World nations?


A gift to the industry (be my guest at LAUNCH Festival)


I’ve been hosting my Launch Festival for six years now, with the goal of making the most supportive and joyful startup event in the world for fellow founders.

We’ve had amazing startups launch, including Yammer, Powerset, Mint, Space Monkey, Dropbox, Docstoc, Brilliant.org, Boxbee, FitBit, RedBeacon, AdStage, Clicker and Swipe.

In this, our seventh year, I’d like to offer a free pass to the event:

Sign up: http://launch.ticketleap.com/launch-festival-builder/dates
Details: http://festival.launch.co

When I started in the industry in my 20s, I didn’t have a pot to piss in and was a ‘little rough around the edges’ – I was so lucky to have folks like Esther Dyson, Kara Swisher, John Battelle, Tim O’Reilly and (most of all) John Brockman include me in their events.

These events led to me rubbing elbows with Evan Williams, Yossi Vardi, Larry Page, Jeff Bezos, Ted Leonsis, Steve Case, Mark Cuban and countless other luminaries. Some of them became good friends and/or critical business contacts.

Now I’m trying to pay it forward for the 40+ startups that will launch onstage, the 150 that will be at demo tables, and the thousands of founders and technologists who maybe don’t have the budget yet to come to a world-class conference.

LAUNCH Festival is my legacy and I want as many folks to experience it as possible.

We had 6,000 people sign up last year and this year we hope to have 8,000 (stretch goal FTW!). This makes us the largest startup conference in the world – by far.

How are we able to do this?
First, we have premium tickets for sale that we upsell folks on. Second, we have the massive support of so many friends in the industry who sponsor the $1M+ budget of the event.

Also, sometimes I lose money on the event.

We couldn’t do these sorts of crazy things without the support of our partners – whom I thank from the bottom of my heart:

* wsgr | SOMA (http://wsgr.com)
* Ludlow Ventures (http://ludlowventures.com)
* DFJ (http://dfj.com)
* MailChimp (http://mailchimp.com)
* Microsoft Ventures (http://microsoftventures.com)
* MicroVentures (http://microventures.com)
* Sequoia (http://sequoiacap.com)
* Yammer (http://yammer.com)
* Autodesk (http://autodesk.com)
* .CO (http://go.co)
* Expedia (http://expedia.com)
* Hotwire PR (http://hotwirepr.com)
* Instaradio (http://instaradio.com)
* Sourcebits (http://sourcebits.com)
* Ticketleap (http://ticketleap.com)
* Traklight (http://traklight.com)
* Zelkova Ventures (http://zelkovavc.com)

If you would like to add your name to the growing list of folks supporting the LAUNCH Festival, just email me at jason@launch.co.

We’re 35% of the way to budget, and with the support of the industry we’ll get there together.

It’s going to be an amazing week (three days for the Hackathon, three days for the Festival) – please join me.

Hacking funding with AngelList cofounder Naval Ravikant


If you’ve never heard of AngelList or my friend Naval Ravikant, you’ll never forget the man or the platform after this interview. The online community lets potential investors and startups mingle, meet, and get deals flowing. And now with the addition of syndicates, smaller investors can join in on the deals of angel investors they back. As Naval put it, “it’s like Kickstarter, but for equity.” When he sat down with me at LAUNCH Hackathon, we cut to some core questions early-stage entrepreneurs have. Should I join an accelerator? Which one? How do I get through my Series A crunch? When do I stay lean, and when do I try to scale? All these questions and more answered in this great episode.

Never miss an episode! Subscribe in iTunes: Audio (http://bit.ly/TwiStA) || Video (http://bit.ly/TwiStV)

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Wikipedia’s forgotten founder, Larry Sanger


No one needs an introduction to Wikipedia. It’s the 6th-most visited site worldwide, and 7th in the U.S. But when it comes to the company’s origin, the first name on your lips is probably not Larry Sanger. Larry was hired by Jimmy Wales to edit his online encyclopedia, then called Nupedia in 2000. Sanger developed the site’s ethos, started building the community — and crucially — adopted a little-known editing system that allowed for numerous contributors. Though rarely, if ever, recognized by Wales, it was Sanger who put the ‘wiki’ in Wikipedia. He coined the name, too. Today on the show, the little-known history of one of the most important innovations of our lifetimes. I sat down with Wikipedia cofounder Larry Sanger. Plus we talk about how if the site had stayed for-profit, Wales would have been richer than Larry Page.

Everybody who’s a fan of the show, tweet to Jimmy Wales: Please give @lsanger his credit as cofounder of @Wikipedia. Love, (your name). http://clicktotweet.com/N3W62

Never miss an episode! Subscribe in iTunes: Audio (http://bit.ly/TwiStA) || Video (http://bit.ly/TwiStV)

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English Bulldog

Hello, my name is Jason. Welcome to my blog on the interwebs. You can reach me on twitter @jason and by email at jason@inside.com. My Skype is jasoncalacanis, and my mobile phone is 310-456-4900.

I only pick up numbers I recognize, and in terms of emailing me, the best strategy is to write short, blunt and to the point requests. I can quickly respond to short messages, and many times I simply don't have the time to read five page pitches. In terms of taking meetings, I only do that after reviewing an actual product (not a business plan). So, the best time to ping me is when you have mockups or an alpha site. I don't read business plans, and I've never written one.

Other twitter accounts you can follow: Inside.com, Ticker, This Week in Startups and LAUNCH Festival