The right news, written by the right people. Also known as the answer to fake news. currently runs highly produced topical newsletters for tastemakers and motivated professionals. Due to positioning as a premium brand, could have unique access to high quality contributors, news, and ad buyers. The promised land is a full newspaper in your email, curated to the topics you’re interested in. Jason Calacanis is a seasoned media entrepreneur, angel investor, and seems to be fighting this fight for religious reasons from having V1 of this business ravaged by Google and other walled garden platforms.


Minimum: $1000 Crowd Note, July 2018, 2 year term with 5% interest.



Why investing

Jason Calacanis: he invested in The New Tropic, wrote the Angel book that these notes are based off of, has sat on both sides of the table. Frankly, I’m surprised he’d still want to be on the operator side of the business. In addition, is 100% a media company just like Weblogs that he had before.

500 Startups, my experience in startups, all point me to the truth that the only non-proprietary and largest social network is email, which this business is built off of.

What the risks are

  1. Don’t know how many months of runway they have left (see the chapter in Angel about estimating burn)
  2. Email newsletters end up working like real estate — highly fragmented markets that don’t get network effects from going national (see Uber selling off Southeast Asia divisions)
Check Pass/Fail
1. A syndicate lead who has been investing for at least five years and has at least one notable, unicorn investment Pass: (Calacanis)
2. A startup that is based in Silicon Valley Fail: (Based in Culver City, CA, outside of LA, but team is distributed)
3. A start that has at least two founders (with two, you have a backup in case one quits) Pass: Calacanis, Austin, and Lon
4. A startup that has a product or service that is already in the market (you’re not qualified to invest in startups that haven’t released their products—and frankly you don’t need to take this risk.) Pass
A startup that has either (a) six months of continuous user growth or (b) six months of revenue. Pass:

“Over 667k subscriptions from 390k subscribers, averaged 50% growth for the past 9 quarters”

“We started monetizing our newsletters at the beginning of 2018 and grew revenue from $40K in January to $107K in May. Today, we publish 30 newsletters that span various topics including bitcoin, beer, general news, among others.”

A startup that has notable investors. Pass: Sequoia Capital, Mark Cuban, and Jason Calacanis
A startup that, post-funding, will have eighteen months of cash remaining, commonly referred to as runway (ask the founder and syndicate lead how many months of runway they will have post-funding) ???

What has to go right for the startup to return money on investment

Jason Calacanis’ core hypothesis about email newsletter (and therefore, is right—news is shared socially, and that creating a compelling product on non-proprietary networks is enough.


03/06/19 (update received by email):

Quick Stats

  • Q4 Revenue: $333,957
  • Q4 Net Income/(Loss): ($146,322)
  • Q4 Cash Balance: $2,410,000
  • Full-Time Employees: 9
  • Most Recent Valuation: $15mm Valuation Cap

Key Updates & Highlights

  • Generated $850K+ in revenue during FY 2018, representing nearly 4X year-over-year growth.
  • Added 125,000+ subscribers and 250,000+ subscriptions during FY 2018.
  • Built and deployed a new ad server enabling the company to serve different ads to different readers based on parameters such as profession, geographic location, and interests.
  • Total quarterly newsletter opens increased 50%+ year-over-year (8.96M in Q4 2018 vs. 5.87M in Q4 2017).

Challenges & Lowlights

  • Efforts to drive premium subscriptions have been ineffective with a net gain of only 12 paid subscribers during Q4 (equating to less than $200 in MRR).

12/01/21 Update

Invest in
Republic is a startup investing platform where you can invest as little as $10 in impactful startups
Inside raising a new round at a $25m valuation cap, up from $15m valuation cap I invested at 3-4 years ago.
Revenue hasn't grown meaningfully from 2019 to 2020. 
Our newsletter advertising business has been growing nicely, being profitable with $2,782,057 in revenue in the first nine months of 2021. That's up from $1,304,830 in the same period in 2020.

Review these deal memos every time the startup raises a new round

Test if original thesis still applies