Have you done TechCrunch Disrupt’s Startup Alley ($4,000?! Rip off!)– email me!

I’m looking for some candid — and confidential — information around the experience startups have had buying a table for TechCrunch Disrupt’s $4,000 Startup Alley (which is based off my ‘DEMO PIT’ innovation from nine years ago — except I don’t charge for it).

Email me directly: jason@launch.co

subject: Startup Alley

1. Which city, What year

2. How much did you pay

3. Did you meet investors?

4. Was it worth it?

5. How likely are you to recommend it to a friend? 1 to 10?

6. What was it like, candidly?

Email to jason@launch.co (.co not .com). 🙂

How to select your angel round valuation (aka “the $4m rule”)

“What should I set my valuation at?” countless founders have asked me. It’s not a perfect science, but since I invest in 30-40 startups a year personally, I probably have better data and first-hand experience than any single human being on the planet at this moment.

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Additionally, since 95% of my angel investments ask to me to syndicate their deals, my check size has gone from $25-250k to $50-$1m, making me the lead or co-lead in my deals.

For example, I recently syndicated five deals on AngelList at one time — something no one has ever tried. Four of the five deals were oversubscribed, and the final one is on track to close shortly. When you syndicate a deal people sometimes tell you why they passed, so I get massive information from the minds of angels on what they want to back, and more importantly, what they pass on — and why.

[ Note: if you want to angel invest alongside me, you can apply at jasonssyndicate.com ]

Twenty-seven startups have finished my incubator in the past year and I’ve introduced each to well over 50 investors, and I always ask those investors, “which two companies are your favorites and why?” Then I watch which ones they actually write checks to — if any.

Continue reading How to select your angel round valuation (aka “the $4m rule”)

For Sale: A Dozen YouTube Channels with 4M+ Subscribers

Now that Inside.com is 100% focused on our email newsletter, we’re looking for a new home for the following channels on YouTube. If you’re interested in discussing a deal, please ping me at this form.

My plan is to auction them off on May 1st if we don’t find a buyer by then.

It’s just amazing how much these channels have grown! My guess is that it would cost $1 to gain each subscriber we have on these channels (between content and marketing cost) — and three to five years.

The sale would include all of the videos and related IP.

100-day social media break

I’ve decided to take a 100-day break from social media in order to focus on some important projects I have brewing.

From March 21st until July 1st I’m going to attempt to focus on medium- and long-form content on my blog and Inside.com’s Daily Brief email. Oh yeah, Brockman sold my book, and I’m going to spend the next year writing it, so it’s time to get off the social media crack pipe.

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I love social media. It’s given me a huge megaphone, but I’ve found myself starting and ending my days on Twitter, Snapchat, Facebook, and Instagram for at least 20 minutes combined. Those minutes add up to around 1,200 a month and I need those hours back. Also, sometimes that 20 minutes at night turned into an hour, and it simply feels unhealthy to get wound up debating stuff at midnight.

Like many of you, I go into defensive mode during the day, constantly responding to notifications on my desktop, iPad, and iPhone — as well as important emails. I’ve turned all notifications off and I’m staying off social during the day unless it’s to share a medium- or long-form piece of writing.

No social during the day should save another hour — that’s about two hours saved per day.

Continue reading 100-day social media break

My Angel Syndicate After Two Years: 902 Accredited Investors, 42 deals

In March 2014 we launched a deal for Calm.com to raise $200,000 on AngelList. That deal was oversubscribed and we closed $328,104 across 95 investors who ranged from $1,000 to $25,000 each.

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Eighty-four of the investors put in $5,000 or less, an amount considered impossible at that time, when angel deals had $25,000 minimums.

Today, my syndicate accepted its 902nd accredited investor.


In 24 months we’ve done 42 deals, which is about one every two or three weeks.

We recently closed five deals in one month … we’re picking up the pace.

I wanted to say thank you to the AngelList team — especially founders Naval & Nivi — on creating this very unique platform that has helped so many founders to raise money and find employees over the past two years.

You can join the Rebel Alliance — if you’re an accredited investor — at http://jasonssyndicate.com

Best regards, @jason

PS – You never know, I might figure out how to get all of you “non-accredited investors” into the angel investing game with this Title III stuff that the SEC approved.

PPS – I wrote about the “trench run” syndicate 20 months ago — interesting contrast.

Mullet Style: How we’re covering Trump at the Inside Daily Brief

trump grimace

How the media covers Trump is a big discussion at the moment, as insults and face-grimace memes have evolved into physical violence and the reality that Trump is going to win the Republican nomination. Covering Trump is a must for cable news because, in addition to being the frontrunner for the GOP, he’s transforming their wobbly businesses into ratings and revenue machines. Even if the networks protest, a Trump presidency increases their revenue. Print publications, which have lost more than half of their revenue base in the past two decades, are in a similar boat: he’s the frontrunner and he sells papers.

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The Inside.com Daily Brief isn’t subject to the revenue pressure of the mainstream media (more on that in a minute), so we’re covering the Trump campaign two ways. First, here’s what you need to know, which you will find in the top news section of the IDB. Second, from a 30,000 foot level, here’s the commentary and cultural take on what’s going down, which is in the second half of the email.

We’re rocking the mullet: business up top, party in the back (of the email).

If you feel we are biased please hit reply and call us out — the daily@inside.com email goes to the entire team.

By calling us out you’re calling out @lons who writes the IDB, and who, although he is a kind of a socialist, and living in Los Angeles, he has a long history of working in journalism, many of those years with me, and he works tirelessly to be fair and balanced. He works for what many have described as a “libertarian capitalist” (me) from Brooklyn, who wants the newsletter to grow and be steered by a guiding principle of links that are “important & fascinating.”

Some of you are probably wondering about the sustainability of the newsletter. With 17,000 subscribers already, and over half opening every single email, we can cover the ~$20,000 a month burn rate of the business by making $700 a day with either one or two advertisements, or by hitting 2,000 folks paying/donating $10 a month to keep the lights on. My guess is we try both and hit profitability by the summer.  


1. How do you think we’re doing with our coverage of Trump?

2. What do you think of our mullet?

Best @jason

Why I’m doing a reality show

As some of you might have read, I’m going to be doing a reality TV show starting this week at the LAUNCH Festival. I thought I would share with you why I’m doing it and what it’s going to be all about.

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My goal for the show is to inspire people to start companies that solve big problems in the world.

Reality TV is perhaps the most powerful medium today, and I hope to leverage every ounce of its power to inspire people to start companies — while taking 5% ownership in those same companies for myself. 🙂

The show is going to take an inside look at my weekly accelerator, the LAUNCH Incubator, which happens every Thursday night, for three hours, here in San Francisco. We’ve graduated 27 startups from the program so far. Fourteen of them are debuting on stage this Wednesday, March 2nd, at the LAUNCH Festival.

I can’t get too much into the format, and I can’t say which network bought the show, but I can tell you that it will be the most authentic show ever created about Silicon Valley and startups, because, well, I came up with the concept of the show myself. “Film my incubator!” (Very original, I know).

Continue reading Why I’m doing a reality show

LAUNCH Festival Speaker Line-Up: March 2-4, Fort Mason, SF

We’ve got an amazing line-up of founders and investors for the LAUNCH Festival this year and I wanted to share some of the crazy, awesome projects we’ll be showing and discussing:


How would you like to get from New York to California in 45 minutes? How about shipping containers full of electronics from Chinese factories to the port of Long Beach in two hours — instead of 14 days, and partly across an absurdly polluted frontier? Hyperloop is bringing us closer to that dream, thanks to co-founders Shervin Pishevar and Brogan BamBrogan.

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Keith Rabois has a fascinating new real estate startup, Opendoor, that will buy your home on the spot — truly a groundbreaking concept to create a fluid market for homes (which are one of the slowest assets you can move). He just raised $20 million in a new round of funding.


One of the legendary investors in Silicon Valley, George Zachary (CRV), and I will sit down and talk with one of the legendary creators in technology, Sebastian Thrun, who brought us Google Glass and now the surging Udacity (where anyone can take a course from Intro to Data Analysis, to Deep Learning, to Advanced Android App Development — for free).


3D printing has had a couple of stops and starts in its decade-long trek, but Joseph DeSimone’s Carbon3D promises to change all that. It’s basically the next big step to us all having a replicator from Star Trek, in my mind.


A new startup from my incubator will debut that will replace Starbucks with robots. I’m not kidding, it’s insane.

Continue reading LAUNCH Festival Speaker Line-Up: March 2-4, Fort Mason, SF

Knowing when, and how, to pivot (or, why didn’t news apps work?)

I’ve been beating my head against a wall for the last two years trying to make a news app experience work, and despite great reviews, I’ve failed.

So, we’re giving up on the Inside.com App and focusing 100% of our efforts on a medium that’s resulting in much better engagement — email!

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Why News Apps Failed

Very few people seem to want a dedicated news app, and while my team poured their heart and soul into building what I think was one of the two or three best news app experiences ever, we couldn’t get traction.

We got exceptional reviews, great press, featured by Apple, and tons of glorious feedback from users — but we didn’t have breakout success.

Neither did Circa, Zite, Trov, or Pulse.

Some readers that are part of big companies are still chugging along, like Facebook’s Paper and Yahoo News Digest, but even those well-constructed products are solid but not breakout hits.

News apps failed because social networks succeeded.

People want to get their news filtered through their social network. It’s just easier and more fun to click on news links your friends are sharing than to open a separate app.

Intellectually, you would think that people would have a unique app for each experience in their life: photo sharing, news, shopping, socializing, watching video, emailing, chatting, etc. It turns out that with these social platforms surging, many things are consolidating into them.

Lesson Learned: Social is eating the world. Photos, video, news, and messaging have folded into social, and we all know that Facebook and Twitter desperately want to pull ecommerce into their platforms (but have failed thus far, even though it has worked in Asia).   

Continue reading Knowing when, and how, to pivot (or, why didn’t news apps work?)

When your heroes disappoint you…

Screen Shot 2016-02-12 at 9.56.27 AM
Kimbal & Wolfgang after lunch in 2012 at Spago

For the past decade I’ve watched my good friend Kimbal tirelessly build his brand of “farm to table” restaurants, simply called “The Kitchen,” into a movement.

Like his slightly more famous brother, he focuses on the details relentlessly and the results are just stunning. The Kitchen has seven locations, and is one of the most recognizable brands in the food industry. People are literally begging Kimbal to bring his brand to their hotels and residential buildings around the world — it’s that special.

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Kimbal has moved slowly and methodically, which is exactly the advice that was given to him by one of his all-time culinary heroes, Wolfgang Puck, when they dined three years ago at Spago.

(Side note: Spago is one of my favorite restaurants in Los Angeles, the schnitzel is better than any I’ve had — including in Munich, Bavaria, and Berlin).

The WSJ today outlines Kimbal’s meeting with Wolfgang, who sadly has decided to steal not only Kimbal’s locally-sourced concepts, but also, this is where it gets just bizarre, the brand.

“The Kitchen… by Wolfgang Puck” is launching soon with recipes that use “only the freshest, locally sourced ingredients.”

In the technology industry we have a long tradition of people mentoring each other, and sure, people riff off each other’s ideas, but the wholesale stealing of a brand and concept like this is just disappointing and strange.

Wolfgang is such a creative force I’m certain he could come up with a dozen viable names that don’t confuse the public and impede Kimbal’s ability to build his business.

I would love to say there is some grand lesson here about entrepreneurship, but I can’t find it. Sometimes your heroes just disappoint you, I guess.

A simple change like calling your efforts “Wolfgang Puck’s Kitchen” would do wonders Wolfgang — and it would trade on your legendary career, not Kimbal’s budding one.

Incubator hopping: Should you go to more than one incubator?

My pal Sam Altman wrote a post about a growing trend I’ll call ‘incubator hopping,’ in which he explains that going to another incubator may actually DECREASE your chances of getting into YCombinator, rather than giving you a better shot.

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Some incubator heads I spoke to read Sam’s post as a scare tactic designed to discourage founders from going to other programs. Let’s put that inside baseball stuff aside for now and focus on the actual question at hand:

Should you go to more than one incubator?

I’ll give you the correct answer, which is obvious, but dependent on your options. Specifically, it depends on a) how strong a reputation you have as founder, b) the overall strength of the business and c) how competitive a market there is for your equity (which is tied to points A & B above. At least in a rational market).

Here is exactly what you should do, in order of how strong you are (on a scale of “seemingly invincible” to “desperate”):

  1. (SEEMINGLY) INVINCIBLE: If you can raise an A-Round without ever going to an incubator, you should do that. You’re obviously awesome and don’t need help from an incubator. You can, and probably have, self-funded your MVP.
  2. VERY STRONG: If you can raise a seed round right now, you should only go to an incubator if you think it will increase your chances of getting an A-Round (which is very hard to do in 2016).
  3. STRONG: If you can’t raise a seed round, but you get into a high-quality incubator, do it quickly. Incubators are the way many angels and syndicates look for a signal that you’re worth a seed round — and they’re right! If you make it through a respected incubator, you should have been vetted to the point at which you have a working product, some customers and perhaps even revenue, which greatly improves the angel’s chances of getting a return.
  4. WEAK: If you can’t get into a ‘Tier One’ incubator, but can get into a second tier incubator in a second-tier market with second-tier mentors (i.e., folks without killer track records), well, that’s better than not starting a company in my book! Give it a shot, and if you fail, the only thing you’ve lost is six months of your life. You’ll have learned a ton and increased your chances of being part of the first three groups above!
  5. DESPERATE: If you went to an incubator and didn’t raise a seed round, or you did and you’re out of money, you’re going to want to take a deep look in the mirror and ask the following questions:

a) Does your product suck?
b) Does your team, ummm, suck?
c) Is your team awesome and you just picked a bad idea?
d) Is your team awesome and everyone else in the world is wrong about your idea?
e) Is your team awesome and you’re on the cusp of a breakthrough / pivot?

Continue reading Incubator hopping: Should you go to more than one incubator?

Build & fund a startup in 48 hours with this simple hack

Startups really need five things in their first year:

  1. Investment (or revenue!)
  2. Talent
  3. Feedback from investors
  4. An MVP
  5. Attention (press, buzz, users, etc.) 

What if I told you that you could spend 48 hours, over a single weekend, and make massive progress on, or even solve, all five of these challenges?

Might you be interested in that??!

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Well, I’ve seen startups form a team, build an MVP, get critical feedback from experts, raise money, get press, and get accepted into elite incubators using this one single hack.

What’s this amazing hack?


In fact, not only did I invest in the last two winners at the LAUNCH Hackathon, Interviewed.com and WizzyWig, but they were also BOTH accepted to YCombinator.

I. Why Hackathons Are Your Secret Weapon

The reason hackathons are so powerful is because they force small teams to make something specific that the judges — who are founders, technologists, and investors — can easily understand and appreciate. 

Constraints not only make for great art, they make great startups. By only having 48 hours and 3-4 team members, you have to focus on what’s important. You’re not going to build 10 features, you’re going to build the most important one or two that you need to demonstrate your value to the judges — and that you can build quickly.

Angel investors love hackathons because they signal who is a serious founder who deserves funding. If you’re willing to give up a weekend and compete against other founders to impress them, angels will — correctly — believe that you’ve got the grit and tenacity to be funded.

Continue reading Build & fund a startup in 48 hours with this simple hack

The Controlled Deflation of the Bubble is Almost Complete

For the past three years, everyone has been kvetching about this fakakta bubble and, frankly, it’s annoying.

Today, I announced on CNBC that the two major bubbles we’ve all been so worried about — the early- and late-stage private company bubbles — have been successfully deflated in a very controlled fashion.

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Early Stage Comes Back to Earth

In the early-stage space, I’ve seen the uncapped notes and “12-15m cap” notes for YCombinator companies with 10 weeks of growth go away completely — and that’s a good thing!

In fact, I was laughing out loud with a founder about the uncapped note in 2015 at the Golden Globes on Sunday night. (Event drop is the new Name Drop!) The only thing funnier than the fact that serious investors gave him a mountain of cash without knowing how much they paid for their shares was Ricky Gervais taking apart Mel Gibson.

In the past couple of months, I’ve seen the early-stage pull back in a major way. Here are some common events I’ve witnessed (with specific startup names/details anonymized):

  1. Startups that are doing well having to meet with over 50 investors to close a flat round.
  1. Startups doing bridge rounds with a 2-3x liquidation preferences (this means those recent investors get a guaranteed return of 2-3x their money before any other shareholders get paid).
  1. Early-stage investors telling me they are “taking a pause” on investing in new companies for the next six months. In fact, two non-traditional, authors-turned-angels, Tim Ferris and Tucker Max, have both announced they’re hanging it up.
  1. Startups coming out of elite incubators that can’t hit their target valuations or raise amounts coming back to me six months after graduation with “rebooted” valuations.

Continue reading The Controlled Deflation of the Bubble is Almost Complete

We asked 6,491 founders what they’re buying next year … here’s what they told us


We asked 6,491 (of the 15,000) people we plan on having at the Launch Festival this year what services they plan on buying in the NEXT YEAR.

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If you’re in the cloud computing, advertising, data analytics, legal, email, design, etc., space we’ve got thousands of folks who want to meet you.

In case you didn’t know, we run the event — which cost $1.5m+ to put on, at a break even (or sometimes slight loss), in order to support founders and inspire innovation.  

We can only make this happen because amazing partners like IBM, Sequoia Capital, Ludlow Ventures, WSGR, InVision, Localytics and SLACK help us throw the party.

You can join us as a partner by emailing me personally at jason@launch.co or filling out this form.

We really could use your support throwing the party … and hey, you’ll get a ton of customers for your product by helping us — that whole, win/win/win thing!

Snapchat is going to reach a billion users thanks to “Gen-S” — the smartphone generation


Snapchat is going to reach a billion users, challenging Facebook, YouTube, and mainstream media, for the attention of “Gen-S” — the smartphone generation.

I know this because this Christmas a bearded, chubby, and jolly fellow showed me the power of Snapchat.

No, not Santa Claus, the hip-hop version of Old Saint Nick — DJ Khaled.

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Every time this one-part Tony Robbins, two-parts Puff Daddy takes the screen, over three million views come pouring in. Yes, you read that correctly, three million views every time a DJ from Miami gets a massage, smokes a stogie, or shows you his shoes.


Kim Kardashian and her clan get just under two million viewers per episode now, down from 2.5 – 3 million they used to pull in.

These are not apples to apples, with Khaled sharing 5-second clips, but it’s fair to say the viewership is similar. Where things diverge is the cost, with the Kardashians signing up for four more years of documenting their lives for $100m — and that’s just their salaries.   

What makes Khaled so watchable is that he is not obsessed with his own success (and what it buys), but his message of hope — he wants you to be as successful as he is. It’s a classic device, but it works.

In another year Khaled will, if he keeps this up, grow his audience by 10x, and have 30 million folks watch him pour Apple Ciroc vodka, “bless up” his audience, and give all of us the “major keys” to success.

Continue reading Snapchat is going to reach a billion users thanks to “Gen-S” — the smartphone generation

From 2012: There is no Series A Crunch.

I wrote this piece back in December 2012, when folks were in a panic over the “series A Crunch.”

Does/did my argument hold up, three years later?

best @jason

From November, 2012: The “Series A Crunch” refers to the fact that while angel-funded startups (think: $750,000 invested by angels in two founders) have grown five times-plus in the past three years, the number of Series A fundings (think: $3 million invested by a venture capitalist in a 10-person startup) has stayed the same.

I’m telling you right now this is a complete non-issue.

Many folks are obsessing over the supposed “Series A Crunch” because, quite logically, if there is a fixed number of Series A investments to go around and a lot more folks fighting for them, well, many folks will not get one.

Parents fleeing a public school system increase the demand for the (relatively) fixed number of slots in private education, making those slots more and more valuable. In fact, it only takes a percentage of actors to “switch teams” to cause an imbalance.

What these folks, largely journalists, who have no experience in business, fail to realize is that “things” do not always stay the same in an equation — and that founders should be wickedly good at adapting to changing conditions.

Fact one: The number of Series A fundings could dramatically increase.

The number of slots for players in the NBA this year was 435 (29 teams times 15 players). However, when the NBA started 60 years ago, there were only 11 teams, so the number of slots totaled just 165 (assuming 15-man rosters back then).

In the coming years, the NBA will, mark my word, add a half-dozen teams in Europe and Asia. It’s safe to assume there will be a 40-team league some day.

Additionally, after the shortened NBA season last year, fans, players, and the league realized 82 games were not as much fun as a condensed 50 to 60 game season. I believe the NBA will go to two shorter seasons a year: one US-only and one international.

With two seasons and a dozen more teams, it’s possible the number of slots will grow to 500 or 600 — or more.

Bottom line: Capacity increases along with opportunity.

VCs are a greedy lot (and us founders and GPs love you for it), and the world has mountains of money sitting in bonds, gold, corporate stockpiles, and plain old devaluing C-Notes (aka cash).

If 10 companies with the metrics of Fab, Dropbox, Yammer, Uber, or AirBnb were to walk into a VC firm with only the money to fund five, you know what they would do? Raise more money!

Capacity expands all the time, and it could turn on a dime. Look how quickly Marc Andreessen and Ben Horowitz raised fund after fund in the last couple of years.

Television is another wonderful example of capacity increasing.

Just 30 years ago, your chances of being an actor in a TV show was something like 20 shows on each of three different networks with seven characters on each. That means there were 420 slots available (20 shows times three networks times seven characters = 420).

Since that time, the number of channels has grown and therefore the number of shows with slots for actors.

Additionally, shows now have numerous plot twists per shows, which means shows need many more characters. Compare shows like “All in the Family” or “Happy Days” to more recent series like “The Sopranos,” “Game of Thrones,” or “The Walking Dead.” Tons of new characters are introduced into every episode of those later shows. I think you could count on one hand the new characters introduced on “Happy Days”: Pinky Tuscadero, Mork, and Chachi.

TV has experienced a double expansion: more shows and more characters per show.

This would be like the NBA deciding to make the court 20 percent bigger and putting 14 players on the court at a time rather than 10. (Wonder what that would be like?)

Fact two: A Series A is not the only option to grow a business.

Most pre-Series A companies have under 5-10 people and no revenue. Therefore they “burn” about $50,000 to $75,000 a month in my experience (think five people times $75,000 a year equals $375,000 plus $100,000 in other costs).

Here’s an absolutely crazy idea for folks “facing” the Series A Crunch: Make $2,750 a day (about $1 million per year). If you’re burning two or three times that amount, well, cut one-third your costs. VCs will fund any company with a Series A if they are making $2,750 a day.

If you can’t hit breakeven, well, shut your company down and go work for a startup that can. If you can only hit $1,000 a day, merge your company with another one that is making $1,000 a day and cut the bottom one-third of the staff.

Not willing to do that?

Well, if you’re not willing to give up your diapers and put on your big-boy undies, then you need to stay in nursery school for another year. Series A is for folks who don’t make wee-wee in the bed.

Fact three: VCs are not the only source of funding.

If you have some combination of solid growth, decent revenue, a great team, and a sexy product, you can easily — yes, easily — raise money from strategic investors or rich people. Is this ideal? Some have argued strategic money is bad, but those folks are usually VCs who are in competition with the strategics.

VCs really hate strategic money, because it is valuation insensitive and can result in an early exit (e.g., if Home Away had invested in Airnbnb, perhaps they would have been talked into selling in the HomeAway IPO).

If you went to Mark Cuban with a company making $25,000 a month, no or low burn, a big vision and a reasonable valuation, he will put money into it. I know, he invested in my last company — and many others — with that profile. Rich folks are very, very smart and they know that businesses that have money in their bank accounts and customers paying for their product rarely go to zero.

Bottom line: You’re in control of your destiny, and obsessing on the blogger-manufactured “Series A crunch” will only distract you from the work you need to do survive the winter. And winter always comes. Always.

Why I’m bringing back the Open Angel Forum


[ tl;dr: I’m bringing back my angel dinner, the same one Uber & Thumbtack pitched their seed rounds at, at my house on December 2nd, because startups really need help getting past their seed rounds. ]

Back in 2009, I started a dinner party called Open Angel Forum. The goal was to kill the Keiretsu Forum, which charged founders thousands of dollars to (supposedly) pitch angel investors.

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Using the term “supposedly” because many founders told me the only follow-up they got from these payola groups was from service providers who attend them pretending to be angels.

Open Angel Forum alumni include: Uber, Thumbtack, Backupify, Contently, Food52, Signpost, StyleSeat, and countless others. They all raised part of their first round of funding at this wonderful event.

Then AngelList came around and there were many more angels than startups. There was no reason to host Open Angel Forum, at least not in New York, LA, or San Francisco. (They kept doing it in Boulder, actually).

Now I see a need for the Open Angel Forum again, but not because there are predatory scumbags trying to trick unsuspecting founders into paying for access to angels.

The problem today is that there are some great angel-funded startups that are stuck between the angel-funded world and the VC world.

Continue reading Why I’m bringing back the Open Angel Forum

What I learned from passing on investing in Twitter & Zynga — & saying yes to Uber & Thumbtack


This week I was asked to speak to a dozen billionaires at a secret meeting about putting $100b to work. They wanted me to talk about what I’ve learned over the past five years as an angel investor.

Well, here it is.

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It took me five years, but I’ve learned what the two most important factors are in the success of an angel investor. It’s not being smart, it’s not being diligent, and it’s certainly not being a visionary.

After passing on Twitter and Zynga, I invested in Thumbtack and Uber. Looking back, I knew Ev and Mark were winners, but I didn’t think their ideas — for “updates” and “social poker” — were winners.

I was wrong about their ideas, but I was right about them.  

When Travis and Marco came along with their ideas, I didn’t even try to judge if “on-demand drivers” and “a better craigslist” were winners, because I knew the individuals were winners.

That’s enough information to make a bet.

Which leads me to “Jason’s Law of Angel Investing,” which states:

“You don’t need to know if the idea will succeed — just the person.”

Continue reading What I learned from passing on investing in Twitter & Zynga — & saying yes to Uber & Thumbtack

FIGHT! FIGHT! My response to the CEO of Outbrain

[ tldr: The CEO of Outbrain sent me a choice email regarding AdReplacer, which might — at some point in the future — impact his business in some minor way. Here is my response. I’ll leave it up to him if he wants to publish his email. ]

Thanks for reaching out. Let’s split this into three issues here. First, my support of startups; second, how consumers feel about advertising (and your product); and third, the morality of adblockers.

[ Click to Tweet (can edit before sending): http://ctt.ec/ia53d ]

In terms of my support of startups, it speaks for itself:

  1. 150 angel investments
  2. almost 600 episodes of This Week in Startups
  3. 20,000 free tickets distributed for my events, Launch Festival, SCALE, etc., this year alone

To the second point, consumers are fed up with overbearing advertising. This is a problem that has been caused by aggressive marketers and the publishers who enable them.

Advertising inventory has exploded, but at the same time, consumers have become much more savvy about avoiding tricky ads. Which then requires marketers to get even trickier and more misleading.

This has resulted in the wholesale destruction of journalism’s famed “Chinese Wall” between editorial and sales, with even the New York Times trying to trick their customers into clicking on “native advertising.” It’s disgusting to anyone who cares about journalism and keeping the public well-informed.

Native ads are perhaps “Peak Deception” in this war between marketers and readers, with Google’s confusing search ads being a close second. (Reports show that up to 40% of Google users don’t know they’re clicking on an ad — something that has caught the attention of even the FTC, which is handing out warnings.)

Publishers will do anything they need to in order to survive. Except, it seems, charge for their content. They’re probably right not to charge, because most consumers don’t want to pay. And so the Cold War continues!

Continue reading FIGHT! FIGHT! My response to the CEO of Outbrain