Always Have a Plan B and C Teed Up


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I spent 10 years living in Los Angeles, traveling up to the Bay Area every other week, sometimes weekly, to do angel investing.

During that time I learned that SFO is a complete disaster, with Karl the Fog creating all kinds of trouble. Also, I was frequently missing flights with insanely unpredictable traffic patterns in L.A. and the Bay.

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When I made a little cheddar, I started treating myself to the fully refundable Southwest Premier tickets, you know the ones, that let you board first and take the aisle seat in row two. The coveted seat that lets you put your bag under the seat in front of you which in turn lets you bolt past the row one customers who are fumbling for their overhead luggage.

So, I started having my EA book me three flights back Continue reading “Always Have a Plan B and C Teed Up”

Zuckerberg tries to buy off journalists with .3% of Facebook’s yearly revenue


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Yesterday I wrote the first piece in a three-part series about how Facebook could turn around their “WORST. YEAR. EVAR!!!”

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The basic premise: share revenue with publishers, Instagrammers/influencers, App developers and anyone else creating content on the platform, just like YouTube, Airbnb, Apple and Google’s App Stores and countless other partnership platforms do.

Right on cue, Facebook does the most misguided, heavy-handed and unsustainable version of sharing the wealth, by sharing $100m a year — .3% of their yearly revenue — in a series of grants.

The cynical take is that these kinds of one-time payoffs, to highly influential media organizations, are designed to silence and tamper criticism — they’re buying off influential people for a pittance.

The most gracious take is that Facebook feels bad for being such a horrible partner to the press and democracy.

Either

Continue reading “Zuckerberg tries to buy off journalists with .3% of Facebook’s yearly revenue”

Saving Facebook, a Three-Part Strategy for the New CEO


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Orson Welles Vintage GIF

Facebook’s self-inflicted wounds come from their founder’s obsession with growth, which at its core was based on three extraordinary tactics: removing friction, staying focused on global growth and stealing other people’s ideas.

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There is no debate over this.

If Zuckerberg had not set the tone of “move fast and break things,” the company would have been more thoughtful about their growth, and if they didn’t steal other people innovations so systematically — from Friendster to FriendFeed to Twitter to Snapchat — they would never have dominated the planet.

Of course, that obsession with speed and copying has resulted in — as Zuck himself instructed — the breaking of things, including our privacy and our democracy.

Well done!

In this three-part series, I’m going to outline what the new CEO of Facebook should do to reverse the massive ill will Continue reading “Saving Facebook, a Three-Part Strategy for the New CEO”

A carry comp kerfuffle in Micro VC land


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The SJW crowd piled on to a job posting for a part-time VC job at a micro VC yesterday. The job posting was for 20 hours a week and the compensation was based on a share of the carry.

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Here is how carry works, briefly: if the Fund invests $2m on behalf of investors and turns it into $22M (11x, cash on cash) the gain would be $20M. The carry would be 20-30% of that gain, depending on the deal with LPs (limited partners), which means $4-6M in gain.

[ Note: A 10x fund is the outlier goal. ]

If the Fund manager gives this “Chief of Staff” position 20% of the carry it would be $800-1.2m for a part-time job. Note: 20% would be very generous if the person had cash comp, but if the person takes Continue reading “A carry comp kerfuffle in Micro VC land”

Why aren’t VC firms focused on slow/modest growth startups?


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Yesterday’s post mocking the New York Times’ link-baiting story created a lot of debate on Twitter.

One thing that came up was, why don’t venture capitalists fund slower growth startups? Or, said another way, why don’t VCs invest in startups that grow at a normal pace?

[ Click to Tweet (can edit before sending): https://ctt.ac/sH8h8 ]

The number one job of a venture capitalist is to stay a venture capitalist.

This might sound cynical but, as a VC, if you don’t return enough money to your LPs (limited partners, a VC’s investors) you will not be able to raise your next fund. If you don’t raise your next fund, you’re not collecting management fees to pay yourself and your team, and you don’t have a chip stack to play in “the big game.”

If you want to STAY a venture capitalist you need to land these “dragon egg” Continue reading “Why aren’t VC firms focused on slow/modest growth startups?”

WARNING: Venture Capital is for founders who want to grow fast (duh)


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Once again, the press is here to remind poor, unsuspecting founders that venture capital can — GASP! — result in your startup trying to grow too fast. From today’s New York Times comes the link-baiting title: “More Start-Ups Have an Unfamiliar Message for Venture Capitalists: Get Lost:”

The V.C. business model, on which much of the modern tech industry was built, is simple: Start-ups raise piles of money from investors, and then use the cash to grow aggressively — faster than the competition, faster than regulators, faster than most normal businesses would consider sane. Larger and larger rounds of funding follow. The end goal is to sell or go public, producing astonishing returns for early investors. The setup has spawned household names like Facebook, Google and Uber, as well as hundreds of other so-called unicorn companies valued at more than $1 billion.

New York Times

[ Click to Tweet Continue reading “WARNING: Venture Capital is for founders who want to grow fast (duh)”

Podcast Recommendation: “Cafe Insider” & “Stay Tuned with Preet”


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Yesterday I shared my personal theory on what makes a great podcaster and recommended “The Bret Easton Ellis Podcast.”

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Today I’m recommending another person I think fits my three criteria, which are, as a refresher:

  1. They’re successful in their field, but not the most successful
  2. The have strong opinions and like to mix it up, but they know how to listen
  3. They don’t care what people think of them, but they want people to tune in

Preet Bharara was the former Attorney General for the Southern District of New York, was fired by Trump and is part of the composite that Brian Koppelman used for the brilliant and sharp-elbowed AG played by Paul Giamatti in the extraordinary “Billions”.

[It’s important to note the word composite in the previous paragraph, because as Preet hilariously told on an early podcast, Continue reading “Podcast Recommendation: “Cafe Insider” & “Stay Tuned with Preet””

Podcast Recommendation: Bret Easton Ellis


This post is by Jason Calacanis from Calacanis.com


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My theory of podcasting is that the best shows are hosted by iconoclasts who share three traits:

  1. They’re successful in their field, but not the most successful
  2. The have strong opinions and like to mix it up, but they know how to listen
  3. They don’t care what people think of them, but they want people to tune in

These people are unmanageable by the corporate entertainment complex, so you won’t find them on cable TV.  

[ Click to Tweet (can edit before sending): https://ctt.ac/bra99 ]

Sure, they would be great guests themselves, but only on a longer form talk show. If you run a network, you would never give them their own show, and if you did it would end in a barn fire.

One of my favorite podcasts is the Bret Easton Ellis Podcast, by the famous author of books like “Less Than Zero” and “American Continue reading “Podcast Recommendation: Bret Easton Ellis”

Lean Management: The Power of the EOD Report


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Wanted to talk to you today about a lightweight management technique I’ve developed over the years called “The EOD and EOW.”

When we hire someone, I tell them that we don’t have management at LAUNCH, that it’s a flat organization and our goal is to stay small but increase our efficiency.

[ Click to Tweet (can edit before sending): https://ctt.ac/Y3JIC

There isn’t a massive reporting structure and you have to manage yourself, and the primary way we do that is an end of day report called the EOD.

The implicit deal is that you’re not going to be micromanaged, or candidly, managed at all, but you will need to “put up numbers” and be accountable to the rest of the team.

The report format is simple and has the following characteristics:

  1. It’s a bullet point list of what you worked on today.
  2. It should take no longer than Continue reading “Lean Management: The Power of the EOD Report”

The Ultimate Outsider’s Hack: Read All The Biographies


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Something Like An Autobiography: Akira Kurosawa: 9780394714394: Amazon.com: Books

A waiter at Sugar Bowl this weekend recognized me from my podcast, and after a couple of meals in the dining room, got up the nerve to tell me he was a huge fan. This is, for the record, one of the most wonderful things a podcaster can hear.

If you see me out, even if I’m with my family, do not hesitate to say “hello,” give me a fist bump, take a selfie (if so inclined), and let me know what your favorite episode is. I like being a micro-celebrity and I love talking to people–don’t be shy!

[ Click to Tweet (can edit before sending): https://ctt.ac/3np2d ]

Anyway, he asked me for three book recommendations for a young person starting out.

When I was younger I wanted to be rich and powerful because I grew up poor and powerless. How anyone got rich and powerful was an

Continue reading “The Ultimate Outsider’s Hack: Read All The Biographies”

The Three Vendor Rule


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When I first started doing events in New York City in the 90s, the first one called “Ready. Set, Pitch,” I realized that vendors would give us wildly different quotes — often for the same exact thing.

That is when I came up with The Three Vendor Rule.

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I told my team to obtain three quotes for everything we did, from A/V to space to food to furniture rentals.

As anyone who has done any management will predict, I got pushback … but not from the vendors, from my own people!

Why do we have to do all this redundant work?

Why couldn’t we just use the same vendor as last year?

In my younger days I would simply say “do it” and walk away. Later on I would say “either you can do it or I Continue reading “The Three Vendor Rule”

Should I move my startup to Silicon Valley: the 2009 & 2019 answers compared


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Often the best advice is situational, and the situation here in the Bay Area has changed dramatically in the past decade. Today I wanted to detail the two answers a founder would receive to the question, “Should I move my startup to Silicon Valley?” depending on if they asked it in 2009 or 2019.  

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Should you move to Silicon Valley: The 2009 answer

It was easy to give advice 10 years ago when founders asked me if they should move to Silicon Valley. The answer was a wholehearted “yes!” Given without reservation or consternation because:

  1. The sheer number of investors here
  2. The density of talented people here

High-growth startups, defined as the ones trying to hit $100M in revenue in under a decade (what you need to attract the elite investors and to achieve unicorn status),

Continue reading “Should I move my startup to Silicon Valley: the 2009 & 2019 answers compared”

How can I do an MVP for a delivery service I want to start?


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ShaneRMTanner on Reddit asks: How can I do a MVP for a delivery service I want to start? The basic idea would is this: A delivery service for people who use Offerup and Letgo auction apps. I do and continue to get validation on this idea. It plagues me that I have thought and continue to think about a solution to this problem. Maybe it’s something I’m not seeing, but, I’m driven to find the answer or move on.

Shane: The concept of an MVP (minimum viable product) is to do the LEAST work to answer the HARDEST questions.

Click to Tweet (can edit before sending): https://ctt.ac/nc9bF

Before defining the MVP, you want to define the question(s) you’re trying to answer.

The questions I have about your business, as an investor, are:

  1. How much are people willing to pay for a delivery service, and can this amount Continue reading “How can I do an MVP for a delivery service I want to start?”

As an angel investor should I invest in a founder working on two projects (or working half time on one)?


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Peter Thiel (in crown), playing multiple Paypal employees at chess — including Sacks (the only winner) and Roelof Botha (to right of Sacks).

Just got asked this question on Quora.

If it’s Elon Musk or Jack Dorsey, sure, go ahead and invest in them.

If it’s anyone else, it’s likely not going to work out well as an investment.

[ Click to Tweet (can edit before sending): https://ctt.ac/c1U8m ]

There are some serial founders who specialize in starting and handing off startups to exceptional managers; Sky Dayton (who founded Boingo Wireless, EarthLink and other startups) comes to mind, but these individuals are rare.

You need to ask yourself as an angel investor the following two questions when looking at a founder with “founder ADD”:

  1. Has this person managed multiple projects before and how did that work out? I’m going to assume they haven’t done this before or you wouldn’t be Continue reading “As an angel investor should I invest in a founder working on two projects (or working half time on one)?”

Chrome OS is the ultimate productivity hack & will exceed Mac OS marketshare — but can it challenge Windows?


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The Acer Chromebox CXI3

I recently replaced all but three of the Macs in our office (the ones used for video editing), with ~$800 ACER Chromeboxes and the stunning, ~$900, USB-C powered Dell 38″ monitors (model: U3818DW).

Google’s Chrome OS is an absurdly fast, stable and distraction-free operating system. Over the past seven years of its short existence, it has become world-class.

Here’s why Google has nailed it:

  1. As the world has moved to cloud-based software, running inside of browsers, the need to download client software has disappeared for almost every task. This means software startups don’t have to build clients for every desktop operating system anymore (some do, most don’t).
  2. The Chrome Browser has become the standard for cloud-based apps to be built on — because it has massive market share.
  3. Chrome Extensions are available for everything you need to do, from password management, Grammarly and advanced email with Superhuman

    Continue reading “Chrome OS is the ultimate productivity hack & will exceed Mac OS marketshare — but can it challenge Windows?”

How to get an angel investor’s attention?


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Don’t say everything

Got asked this question on Quora. The answer for me, and for most angels, is easy: send a short email with a link to the product or a product video.

Protip: Do not email your life story or 3,000+ words on why you built your product. This will make you look deranged.

The goal of your email is to get the investor to a) understand what you’re doing and to b) respond.

You want to send just the most important thing, which is one of the following things 99% of the time:

  1. your product
  2. your traction
  3. your market
  4. your technology
  5. you

What you don’t want to do is send an angel EVERYTHING in the first email. Get them on the hook with the best thing (perhaps two things) and try and get them to ask you more questions.

As an example, Henry from Cafe X sent me Continue reading “How to get an angel investor’s attention?”

Defending self-driving cars in the face of tragedy


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Last month we reached the tragic, and long-dreaded, moment in the history of self-driving cars: the death of an individual who didn’t opt into using self-driving technology. (In this case, it was a pedestrian, but it could have been passengers in a non-self driving car).

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This follows the May 7, 2016 Florida death of a driver using Tesla’s driving-assist technologies (“autopilot”), which are often confused with self-driving technology.

Since that time, two other deaths have occurred while autopilot was engaged, including a driver in China on January 20, 2016, and the recent crash here in the Bay Area on March 23rd.

Four tragic deaths, in four separate instances, using two different flavors of self-driving tech (driver assist & fully automated), but one common thread which we must, as a society and industry, address candidly: user error and — most Continue reading “Defending self-driving cars in the face of tragedy”

“Why do you hate crypto, Jason?” (I don’t, but… )


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“If you are right, that 90% of crypto projects are scams or incompetent, what do you gain by taking that position publicly?” asked a close friend.

I took a moment to think it through.

[ Click to Tweet (can edit before sending): https://ctt.ec/3a1P0 ]

Why was I sounding the alarm on Twitter, my podcast, and CNBC, that civilians should be very careful investing in virtual currencies that are unregulated, anonymous, easily manipulated, phenomenally hackable, global, and often run by bad actors or the incompetent?  

“To protect people from losing their money?” I answered.

I’ve got a complicated relationship with crypto, having monitored early projects like Bitcoin with enthusiasm.

Six years ago I wrote a piece called “The Most Dangerous Project We’ve Ever Seen,” that introduced many in the investment community to Bitcoin.
http://www.launch.co/blog/l019-bitcoin-p2p-currency-the-most-dangerous-project-weve-ev.html

Full disclosure, while I don’t trade cryptocurrencies, I Continue reading ““Why do you hate crypto, Jason?” (I don’t, but… )”

The Seed Slowdown


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My pal Fred Wilson wrote about the “Seed Slowdown” today. The numbers show two clear trends:

1. 2015 was the peak of angel investing in technology startups in terms of dollars and number of deals.

2. 2017 is crashing in terms of the number of deals closed, with dollar amounts off significantly — but not as much.  

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Fred points out some of the reasons for the boom and bust, and I’m in agreement and expand a bit on what happened — since I lived it and recently wrote about it in my book (angelthebook.com).

There were two major trends contributing to the 2014/2015 boom:  

1. Facebook created a crazy number of new investors (e.g., Dave Morin, TWIST #216 and Chamath Palihapitiya TWIST #238 & #776), who were added to the legions Continue reading “The Seed Slowdown”

Should everyone be an angel investor? + some upcoming events


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The biggest question I was asked about angel investing during my New York book tour was, “Can anyone be an angel investor?”

Today I want to try and answer that question and let you know about some upcoming events.

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First, some upcoming events:

This Tuesday, August 15th, I will be in Los Angeles speaking at Google in Venice (Google employees only) from 11:30AM-1:00PM.

Tuesday night, August 15th, I will be speaking at a public event, “Live Talks Los Angeles: An Evening with Jason Calacanis” at 8:00PM, which you can register for here: http://bit.ly/eveningjcal

I’ll be going to Stockholm, New York and Los Angeles in the fall. Frequently updated schedule here: angelthebook.com/tour

Second, “Can/Should everyone angel invest?”

I wrote the book “Angel” in order to detail the risks involved in angel investing, and share

🙂

Continue reading “Should everyone be an angel investor? + some upcoming events”