Why I (we?) invested $378,000 in Calm.com 

My angel fund (LAUNCH Fund) & my AngelList Syndicate just funded a mobile, mindful meditation startup that VCs are (currently) too scared to fund.

jason
6 min readApr 23, 2014

Over the past year we’ve all read about the promise of AngelList’s Syndicate program. I’ve been shouting from the mountain tops that I think this is a revolution because an angel investor like myself could “jump the fence” and fully fund a founder.

Typically an angel like myself gives a founder $10-50,000 to a founder which serves to kick off their fundraising process and maybe build out or improve their MVP (minimum viable product).

Founders take a high-profile angels name and sell it to the VCs and other investors as their “social proof” that they are a serious concern. After this first Silicon Valley blessing things tend to go well for startups. Every week a couple of startups ping me to tell me “We got [insert Kevin Rose/Cyan Banister/Gary Vaynerchuk/Joanne Wilson/Tim Ferriss] to commit! Can we share with you our plans?”

Thus begins a three to six month journey in which the founders sell their vision and their early champion. If it’s one of the folks I mention above they will be able to close the rest of their round in 90%+ of cases. As the profile and track record of the angel goes down, so do the chances (obviously).

Jumping the Fence

Last month I decided to try the power of my fully-operational AngelList Syndicate, which has been brought up over and over again in the media due to its scale (currently the third largest): over $1m in commitments from over 250 individuals.

A company that I fell in love with, Calm.com, was to be my first test. I picked this startup for a number of reasons, including:

√ a passionate founder (a Brit named Alex Tew who loves mindful meditation & who created one of the most viral things ever: the Million Dollar Homepage)

√ exceptional branding (a four-letter domain name that’s in the dictionary!)

√ and solid metrics (many thousands of paying customers, and many hundreds of thousands of free users).

However, the real reason I picked this as my first Syndicate was because I believed this was a project that VCs wouldn’t fund—at least not today.

Mindful meditation is going to be as big—probably bigger—than Yoga. It’s a proven technique, that is being studied deeply by serious scientists at serious universities.

However, venture capitalists are scared of making a bet on something that’s so far left of center. Something that could get them made fun of when it fails (“How’s that meditation mumbo jumbo going? Oh it failed, right… you could have put that into the next enterprise messaging play you idiot!”).

However, it was clear to me that this will work. In 10 or 20 years, folks will look at it as brilliant as investing in a cafe that charged 5x more than average for a cup of coffee in 1987.

Or, it will fail like 6 or 7 of 10 startups we angels invest in. In fact, that’s the purity of angel investing: making very high risk bets in the hopes of finding (another) Uber.

[Plug for my next event: LAUNCH Beacon: Retail, Payments & Location
@launchbeacon, New York City, June 16th]

Syndicate Simplicity

The founder of Calm.com made a very fact-filled profile page for Calm.com on AngelList. I filled in some information about why I was doing the Calm.com deal.

Then we clicked the fire button.

Then a bunch of folks committed to fund our $200k allotment.

Then we were oversubscribed and increased the allotment to over $300k.

In two weeks or so, the money was all wired in and our founder was in business.

Along the way we learned some details, like currently syndicates can only accommodate 99 of the hundreds of members of my syndicate. And that I can pick who are my “starred” members, giving them preference to get into deals.

Obviously someone who has 25 investments and has followed through on 9 of their 10 syndicate deals is a better partner for me than someone who has zero investments and has passed on 9 of 10 syndicate deals they “committed” to via AngelList.

Calm.com can now hire three or four team members — early true believers who will get enormous stock options in the next Lululemon, Starbucks or Lumosity — with that almost $400k we’ve trusted Alex with.

He will not disappoint us, and I will fight hard to make sure he doesn’t.

[ Interesting rumor: AngelList will soon have an ‘autofund’ option. When/if this goes live when I syndicate something the most bold members of the syndicate will automatically have their $1-25k wired to the syndicate—without any work! You just get an email saying “You funded $1,500 in Calm.com. Sign here.’ Or something like that. This will make the process even more compelling and fast for founders because they will be able to understand that the syndicate is an instant funder—faster than a billionaire angel! ]

Here’s to the Crazy Ones

Although we can all afford to lose the investment in Calm.com or we wouldn’t be angel investors in the first place, I am taking massive personal pride in making sure that the AngelList syndicate model succeeds.

If it does, thousands of founders whose ideas VCs “can’t get their heads around” will get VC-level funding from single, risk taking maniacs—urrr… angels—like myself.

We’re jumping the fence, people. We’re going off the reservation. We’re rolling the dice. We’re going to chase it.

This is not going to be for those with a weak stomach.

We’re unicorn catchers, not potato farmers.

The crazy risk takers are the ones who will have the best chance at reaping the unfair rewards in my estimation. That’s my syndicate.

Do not join if you do not want to fail on six, seven or eight out of 10 startups because that’s our goal: to be the first money into the crazy, binary ideas that the VCs aren't ready for yet.

If you can easily understand why we’re investing in every company I post to my syndicate, then I’m not doing my job. My job is to challenge the syndicate with deals that are hard to get your head around. In fact, at least 10 people passed on this investment saying they didn’t see how it could work.

Excellent.

You don't get it and you're not willing to take the risk? Quit! Get out of my syndicate now, because the next couple of deals will, in all likelihood, also make you uncomfortable and perplexed.

You’re best bet is firing up a Wealthfront.com account where you’re safe and sound with absurdly low fees and easily predictable out comes (disclosure: I’m an advisor, not *yet* an investor in Wealthfront—I missed it! Might try and get the syndicate in next round).

For the crazy ones, or the ones who want to hang with the crazy ones, you can (intelligently) gamble with me: angel.co/jason

best @jason

Previously: Why I invested $250,000 in swell

More: Calm.com 1.0 in iTunes

Video: Alex from Calm.com on This Week in Startups

Twitter: Alex, Calm & Jason

Next event: LAUNCH Beacon: Retail, Payments & Location
@launchbeacon, New York City, June 16th

Epilogue

Someone did a bunch of analysis of the nascent AngelList Syndicate program and they seem to think — based on some Moneyball formulas — that I’m #1.

I doubt this because Gil and Cyan are so much more active and smarter than me, but fuck it… it’s nice that someone is taking the time to do this and thinks I’m even in the top 10 most important. The way I look at this is that I’m 1% of the angel Ron Conway and Chris Sacca are (were?), and I’ve got a decade of work in front of me to even have half their careers.

http://www.cbinsights.com/blog/angellist-syndicates-moneyball

someone thinks I’m #1 but I would ignore this and study the returns over time because right now I put Scott/Cyan, Tim and Gil over myself any day

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jason

I angel invest in awesome startups... and try to build them myself. Be excellent to each other.