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  • Jacqui 22:21:34 on 2017-06-28 Permalink

    I wrote a book 


    I wrote a book about angel investing, starting companies and the future.

    It’s called ANGEL and it’s coming out July 18th.

    [ Click to Tweet (can edit before sending): ]

    They offered me a ghost writer, but I decided to write it myself. It took 19 long days, but I think it came out great. If you’re a founder, investor or in any way involved in technology you’re going to get a lot out of it.

    If you’re not in the industry, but you’re interested in breaking in and understanding how it works, well, ANGEL is a candid look at how it works and how you can break in.

    I wrote the book because I believe that the best way to generate outsized results is to own stock in high-growth, private, early-stage technology companies.

    If you’ve ever come to one of my events, or appreciate the podcast or my writing, a great way to show your support is to spend $10-20 bucks on the audio book (I read it), the hardcover or the ebook. If you’re a super fan, buy all three or give them as a gift.

    After you read it, please consider writing a review — if you loved it!

    Barnes and Noble:




    All the best, @jason calacanis

    PS – If you want to angel invest alongside me, or see my deal memos, sign up for

  • Jason Calacanis 18:50:07 on 2017-03-29 Permalink

    Billion Dollar Startup Ideas: The HBO of Podcasting 

    tl;dr: Someone is going to create the Netflix or HBO of podcasting, but it will take a legendary investor to put up $100 million to start a subscription-based network.

    This post was originally published in the Inside Podcasting newsletter. Subscribe here for free!

    Eight years ago I started a podcast called CalacanisCast. We quickly changed the name to This Week in Startups, and over the past seven years we’ve done over 700 episodes, twice a week, week after week.

    This year we will hit $1m in revenue, 95% from loyal advertisers who are thrilled with the performance of their advertisements and my spectacularly heartfelt “reads.”

    [ Note: We created something at the start called “white-listed advertising” which stated that I would never accept a sponsor unless I, or one of my team members, loved the product. We turned down things like LifeLock and e-cigarettes that would have been lucrative but that we personally didn’t use. ]

    We have four full-time employees on the show, not including me, and we are doing not only audio but also video. We do a dozen live events a year on average and “the show” is often the professional highlight of my week.

    The podcast was, in large part, the reason I signed a high-six figure deal for my first book, titled ANGEL, which is coming out on July 18th (pre-order from this link if you want to thank me for all the free content we’ve done live and on the show — I sure would appreciate it).

    My podcast is the best reflection of who I am, probably even better than these email missives because they include me interacting with the startup founders who are trying to change the world.

    The pod has also made me wicked smart, giving me the MBA and Psychology PhD I never had the time to complete.

    2017: The year of the Podcast

    I predict this year is the tipping point for podcasting, with “Serial” laying the groundwork two years ago for “Missing Richard Simmons,” as well as folks like Joe Rogan going supernova, podcasts which are taking the medium from the underground to the mainstream.

    Add to that the fact that Bill Simmons’ TV show on HBO flopped (I liked it) but his podcast is surging, a testament to the fact that talk shows are often awkward and gimmicky — severely so when compared to the authenticity of podcasting.

    I’m guessing Bill is way past $10 million a year in podcasting revenue, and my pal Leo Laporte (for whom I have had the privilege of sitting in as host from time to time) is also at that $10m mark after laying the groundwork for the rest of us.

    Reading advertising isn’t horrible, in fact it’s enjoyable for the right partners. I love reading ads, and have had my listeners yell “ohhh Audible!” and “I love Squarespace! Tommy John! MailChimp!” at me when they meet me — which is hilarious.

    Candidly, selling ads and living hand-to-mouth is hard, even for an established podcast like This Week in Startups, which sells out for three to six months in advance (thanks Luke!).

    On top of all this, podcasts are still hard to measure — something that is a “soft” issue because all the ROI-driven marketers use codes to get directional info on how they are doing.

    Most podcasters would jump at the chance to stop selling ads and start simply collecting a check from an HBO like Bill Maher and John Oliver do, or cash a check from Netflix to produce something pure and unadulterated.

    Podcast fans are more than willing to pay, and we see many Patreons hitting thousands and tens of thousands of dollars per month. When we did our patronage effort (long before Patreon existed) we instantly hit $5,000 a month.

    However it’s hard for a large group of folks to pay for five or ten different podcasts they love, and that’s where I think the opportunity lies: a group subscription for podcasting’s top talents.

    This would remove the cognitive load on consumers looking to support their favorite shows, while allowing the talent to focus 100% of their effort building increasingly better content — not marketing or revenue.

    Simple Math: 100 podcasters, five million subscribers

    If you could grab 20% of the top 500 podcasts over the next two years for the “HBO of Podcasting” at a $4m payment each, you would be looking at a whopping $400 million content budget — or as Sirius XM would refer to it, “two Howard Sterns” and Netflix would call it four “House of Cards” or “three weeks” (of content).

    That’s a ton of money, but for 50 to 250 episodes per year depending on the cadence of each podcast, it would be $16,000 to $80,000 per episode — a HUGE budget for content creators.

    My guess is that every podcaster in the top 20% zone could deliver 10,000 to 100,000+ paid subscribers. Call it 50,000 on average, which means without overlap you would be looking at five million paid subs. With duplication call it three or four million people, each paying $10 a month.

    In other words, you would break even if you could convert 1–2% of Americans into a subscription.

    To put that in perspective take a look at this ranked list of paid subscribers:

    • New York Times: About 3 million (digital + print combined)
    • WSJ: 948,000 subscribers (digital only)
    • HBO App/Direct: 1 million
    • Pandora: 4.39 million (total)
    • The Podcast Company: five million in five years (projected)
    • Hulu: 12 million (launched in 2008)
    • HBO: 49 million (US)
    • SiriusXM: 31 million (US)
    • Netflix: 49 million (US)

    To execute on this business you would need to do a Series A investment of $100m for 1/3rd of the company, followed by three or four additional rounds of investment in the $100–200m range. After spending ~$600 million you would have a service that was self-sustaining and have a high-growth value of 10x top line revenue of $500m — or five billion. You would have an outside chance of becoming the next Spotify or Netflix, putting you in the decacorn club.

    At scale, you would integrate some modest advertising back into the product without having the subscribers get upset — SiriusXM did just that, and it’s barely noticeable when Howard does a quick ad read every hour or so.

    Venture capitalists don’t normally deal in this kind of $100m investment range, so it would take either a very bullish one or a later stage private equity fund to do this.

    There have been dozens of attempts at a podcasting network, but none of them have had the nine figures of funding it takes to get a true subscription flywheel going. A ten or twenty million dollar round of funding won’t get you to first base in a media landscape with Netflix and SiriusXM.

    Sure, SirisXM, Spotify, Audible or Netflix could take this on, but greats companies tend to be great at one thing — so it’s unlikely they would dip into podcasting.

    So, in the words of Kanye West, “Now who’s gonna be the Medici family and stand up and let me create more; or do you wanna marginalize me ’til I’m out of my moment?”



    PS — LAUNCH Festival is next week… join us: // use code JASON10 for 10% off any ticket.

    PPS — Angel Summit is on Wednesday: 40+ angels talk about what they are investing in and why.

    PPPS — My book comes out July 18th and it’s called ANGEL. Will be doing two weeks of media in New York city from the 17th until the 30th of July. If you want to host a book party at your startup or in your city, please hit reply and let me know. We are forming “ANGEL Squads” in various cities to setup Q&A and pitch sessions and I could use your help getting 100 folks to each one.

    PPPPS — We just finished our sixth syndicate at (no longer on AngelList). If you want to see the deals I’m investing in, and possible join us in funding these companies, you can signup to get my deal memos.

    PPPPPS — I’m having fun with, where I regularly share these emails BEFORE I publish them to get feedback. I send maybe five to ten txt messages a month. Nothing crazy, it’s just sort of a fun way to communicate with y’all.

    PPPPPPS — My startup,, publishes concise, compelling newsletters that round up everything you need to know in 20 different verticals.

  • Jason Calacanis 18:42:10 on 2017-03-14 Permalink

    Airpods are Apple’s Best Product Since the iPad 

    To say Apple’s product launches since the iPad have been underwhelming to Apple fans would be an understatement.

    [ Click to Tweet (can edit before sending): ]

    Apple Watch: everyone I know bought one, almost no one I know wears one. It’s confusing and not very useful.

    Siri: after a four-year lead, Apple’s most fascinating service has been embarrassed by the prowess and ubiquity of Amazon’s Alexa — which is finding its way into TVs and washing machines!

    Macbook Pro: After taking years to upgrade the standard laptop for developers and creatives, Apple released an underpowered and overpriced computer with all the important ports removed, creating a healthy market for used Macbook Pros.

    Let those three missteps sink in for a moment.

    Apple’s products used to be drool-worthy by default, now consumers expect to be let down by Tim Cook. In the words of POTUS… SAD!

    The iPhone 7 Plus was an OK release, with its exceptional camera and underwater functionality making up for an otherwise “meh” update.

    Despite all this, Apple is still a money-printing machine, leading folks like Warren Buffett to load up on it while the pundits wonder if Apple is losing its product edge.

    Their one notable exception is Airpods, the most gloriously elegant, addicting and game-changing product that Apple has produced since the iPad.

    Airpods are wireless headphones that look like hearing aids with a tiny stem attached to them. You look like an idiot wearing them right now, primarily because they only come in bright white, not in an array of darker colors that would make them elegantly disappear.

    These tiny wonders are designed to work instantly, as opposed to every other experience you’ve had with bluetooth devices, which constantly fail to connect or lose their connection so often that you ultimately stop using them.

    Here are the nine brilliant features of Airpods I love:

    1. When you tap the case to your iPhone for the first time, they connect with a square box that pops up on your phone. You don’t need to go to Settings > Bluetooth and connect.
    2. When you open the Tic Tac-sized box it tells you the battery life of each pod as well as the case itself.
    3. The case charges the pods, which is brilliant.
    4. When you put the pods in your ears they automatically turn on — brilliant!
    5. When you double tap on the side of the pods, they will either activate Siri or play/pause your audio (it’s your choice).
    6. You can use both of them or just one at a time, depending on your preference.
    7. They work brilliantly for calls thanks to noise canceling and their dual mic setup.
    8. They don’t fall out (at least for me and the majority of users).
    9. Airpods sync with all the devices on your iCloud, so theoretically they will pair with your iPad and Macbook or iMac automatically — this didn’t happen with my laptop for some reason. I had to manually pair them, which worked fine.

    When you put together this entire experience, it’s so delightful that you actually find yourself wanting to consume more audio and make more phone calls.

    The apex of product design is when it is so delightful that it drives more usage.

    It’s a similar phenomenon we see when people who buy a Tesla immediately start road-tripping to SuperCharger stations because the act of driving a Tesla and not paying for gas is so darn delightful!

    That’s Airpods — Apple’s best product in a decade.

    Airpods are the new Smartphone

    The big picture, however, is not that Airpods are the best way to consume podcasts and make phone calls, but what will happen in two years when the box they come in has a 4G connection and a processor, and you can leave your phone at home but still make phone calls, call an Uber or search the web.

    If Apple can get someone competent to run Siri, you can imagine a future in which you leave for work and pop your Airpods on, leave your iPhone at home and do things like this during your commute:

    1. Hey Siri, make a reservation for four at a great sushi bar in San Francisco for 7:30PM tonight, confirm with me which place you select and then email invites to Joe, Susan and Vanessa from work.
    2. Hey Siri, play the latest episode of Bill Simmons’ podcast at 1.35x speed, but fast forward through the commercials.
    3. Hey Siri, set Waze to take me to my office on the 280 unless it’s seven minutes more than the 101 and set my Tesla to 84 miles per hour, but slow down to 72 miles per hour if Waze reports the police are ahead.
    4. Hey Siri, read me my iMessages starting with the people I text the most.
    5. Hey Siri, send my wife a message that I will be home at six o’clock to put the kids to bed and send her my ETA every 10 minutes after I leave work.
    6. Hey Siri, order more coffee for me on Amazon.
    7. Hey Siri, read me the next 5 things on my To Do list.
    8. Hey Siri, please move my lunch back 30 minutes and confirm with all guests.
    9. Imagine someone walks up to you speaking Japanese, and it’s automatically translated for you.  

    All of this would occur without ever having a phone with you or having to take your eyes off the road. As you can see from the examples above, these are all second- and third-generation style requests, those that require some “if thens” and include some conditions (i.e., if Waze sees the cops!).

    We are three to five years away from Siri and Alexa being able to parse these type of requests. Whoever can do complex instruction sets by voice and across apps and connected devices (i.e., my Tesla and Waze) will be a huge winner in the post-smartphone era.

    In this example you would have a total of two ounces of computer on you.

    Two. Ounces.

    The Big Vision Airpods + Watch + Apple Glasses

    Clearly Apple will launch AR — augmented reality — glasses in the next year. Tim Cook has professed his love for it and Robert Scoble, who is often right about such things, has been talking about this incessantly.

    Apple’s bought a couple of companies, including Metaio, FaceShift, and PrimeSense, that would lead one to believe that Apple Glasses are a lock — but you never know with Apple. The physical TV and the car seemed well on their way to Apple Stores before Tim Cook pivoted those projects.

    Imagine a future where as you run the series of commands I mention above all of my examples were overlaid onto your view of the world.

    You would now have two ounces of Airpods (with their case), combined with two ounces of Apple Glasses, on your person.

    All of this will make the smartphone obsolete.

    Not in our generation, but certainly for our kids.

    Why on Earth would you crane your neck into a tiny screen and carry a brick with you? It makes no sense to do this when you have a more elegant solution, which includes projecting data and interfaces on to the real world with Apple Glasses and interacting via the Apple Airpods.

    You can add a watch if you want to the mix, but candidly, why would you care to look at your wrist for notifications or the time until your Uber arrives when it could be projected into your eye already?

    You wouldn’t.

    All of this requires Apple to fix the disastrously closed and deformed Siri, which is the linchpin of this vision.

    Airpods will be easy for Amazon and Google to knock off, and with Alexa and Google assistant being far better than Siri, I’m guessing we will see them both release similar products in the market in 12-18 months.

    The Augmented Audio Reality Wildcard

    Airpods represent a fascinating tool to mess with our reality by re-mixing our base reality with digital audio. Imagine having Siri lower, or eventually remove completely, the sound of cars while increasing the clarity of human voices around you. Walking down the avenue with a friend would become as quiet as talking in bed in the middle of the night.

    Imagine looking at a specific person in a crowd and having their conversation from across the room amplified while everything else is muted.

    Or perhaps while you’re walking down the deserted beach you could add playful dolphins squealing and splashing next to you, with their bodies and the splashes they create being added to your augmented world with video and audio.

    Heck, why not turn your mountain hike into a time-travel adventure back in the Jurassic age?  


    You’re going to shocked by this, but Apple Airpods are way too expensive at $159. They really need to be $50 or $75, but Apple knows their fans love to give them their money so don’t expect these to drop to $50 with an Apple logo. But it’s obvious that Google and Amazon will make $50-100 versions, as I mentioned above, in the coming years.

    Oh yeah, you’re going to lose these things, just like you do phone chargers. And it will suck because, well, they’re really expensive.

    Set up your Apple Airpod Implant Surgery

    Don’t be surprised when we eventually start embedding this technology directly into our bodies. Having implants inside your ears that gave you these features, as well as contact lenses as the new screen sounds like science fiction — but are we really that far off?

    What a time to be alive.

    We live in the future!

    Best, @jason

    PS – I shared this newsletter with members of last week and got some amazing feedback before publishing. Jason’s txt list is a little tool I built that lets you sign up for SMS messages from me. 1,400+ folks have signed up, only 30 people have unsubscribed and I’m using it as a “private twitter” of sorts. Not sure where I’m going with it, but it’s been fun.

    PPS – Founder University is taking place on April 3-4 in San Francisco. It’s a free, two-day course for founders who are looking to sharpen their game. We are going to live stream it by invite only, so if you want to watch the class live visit (yeah, they have a .university domain name now, cool).

    PPPS – The Angel Summit is almost sold out. Forty angels & VCs talk about what they are investing in and why for 15-20 minutes each. Two tracks with lunch and an “Angel Dinner.” Sign up at Use the promo code JCAL10 for 10% off.

    PPPPS – I just finished my book on angel investing. It’s coming out on July 18th. I’m looking to do a book tour where we do readings/meetups around the country. If you think you can get 100 people/books sold, email who is setting up the stops on the tour.

    PPPPPS – I have no idea how to market my book. If you have ideas hit reply and tell me. Curious what you think will move books. I would like to make my publisher Harper Business really happy so I can write a second book! I really did enjoy writing this one.

  • Jason Calacanis 17:55:43 on 2017-02-16 Permalink

    The Syndicate 

    [ Tl;dr: We’re creating the world’s largest startup angel syndicate at the LAUNCH Festival on April 6th & 7th. –@Jason Calacanis ]

    For close to 100 years non-accredited investors — currently defined as those making less than $200,000 a year or with less than one million in net worth excluding their home — have not been able to invest in private companies.

    That all changed this past May when the SEC started allowing everyone in the United States access to what I believe is the greatest wealth creation vehicle in the world today: startups.

    [ Click to Tweet (can edit before sending): ]

    Over the past 10 years startups like Dropbox, Mint (sold to Intuit for $170m), Yammer (sold to Microsoft for $1.2b), Fitbit (went public in June 2015), PowerSet (sold to Microsoft for $100m), Clicker (sold to CNET for $100m), Trello (sold to Atlassian for $425m), TrueCar (raised $70m in its 2014 IPO), and Cafe X (raised $5m) have presented at our event — but 97% of the people at the event were not allowed to invest in them.

    This year we’re inviting all 120 startups at the LAUNCH Festival to accept investment from the 12,000 attendees, SeedInvest’s network of 150,000investors and the tens of thousands watching at home.

    We’ve known this was coming, so four years ago — back in 2013 — we created a “virtual investing” contest at the LAUNCH Festival where consumers could invest 10,000 “LAUNCH Dollars.”

    This year the investments will be real!

    We’re going to track actual investments (and investor interest) of the startups at the show and display the results in real time. If you’re interested in investing in a startup, for as little as $500 you will now be able to do that.

    I’m thrilled to announce that SeedInvest has partnered with us to provide the services required to run these equity crowdfunding campaigns.

    We are going to email the names of the startups crowdfunding at LAUNCH Festival two weeks before the event so that you can do your research. You can invest if you’re attending in person or watching on the live stream.

    Additionally, I will be investing in every company that runs a crowdfunding campaign at the event — so I have my skin in the game!*

    And one more thing.

    All of this will be recorded for a new, 30-minute show we’re launching, called “The Syndicate.”

    We will announce the participating companies on Monday, April 3rd.

    Tickets to the LAUNCH Festival can be purchased at – use the code BOOM to get 20% off.

    To join our angel syndicate visit TheSyndicate.Fund. For more information on SeedInvest, visit

    All the best, @jason & the LAUNCH Team

    * Pending due diligence & making sure they don’t directly compete with one of my existing companies (which is considered in poor taste in angel investing).

  • Jason Calacanis 17:04:18 on 2017-01-19 Permalink
    Tags: launches 14th newsletter 

    66UImi1 has launched its 14th newsletter: Our mission is “to make you smarter & better at your job.”

    We write every single newsletter with this in mind, and we’ve perfected a format that is wildly addicting to our readers. We read hundreds of stories in a vertical, and we summarize the top 12 of them perfectly so that you can quickly get up to speed.

    We respect our readers and don’t try to trick them into clicking on links to get more page views. In fact, we only want one page from you ever, and that’s on the signup form for the topic you care most about. (electric vehicles, autonomous driving, etc.) <– netflix, amazon, etc, <— AI, Machine Learning <— one great long read a day
    Some upcoming newsletters you can vote on:


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