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Now is the best time to be an angel investor (let me show you how)

27 March, by Jason Calacanis[ —]

I’ve been getting a lot of questions about the impact the coronavirus will have on startups and angel investors, so I thought I would tackle the issue head-on in this essay. 

[ Click to Tweet (can edit before sending): https://ctt.ac/NBz9K ]

Giant disclaimer up top that (obviously) everyone’s safety and well-being is the most important thing right now. Full stop. However, everyone knows that the second and third-order effects of this pandemic will be the economy.

The economy means people’s jobs, and people’s jobs are how they provide food, shelter, medicine, education, and safety for their families. 

We lose jobs and some people will lose their safety, be it in the form of housing, food or medicine — let alone the mental health crisis that can come from being unable to provide for yourself and family.

With that disclaimer out of the way, I want to talk about investing in startups, which is what drives the economy through job creation. I’m sure some snowflakes out there will try and cancel me for talking about investing in startups right now, but those same snowflakes will attempt to cancel me on their iPhone while on Twitter and getting their food delivered from DoorDash (aka startups backed by angel investors).  

In this quick essay, I want to explain why I believe that NOW is the best time to start angel investing. I encourage you to do so intelligently, slowly and with a strategy, which I will also talk about here. 

Background: The most important thing I’ve learned about investing in startups over the past decade is that your results will vary radically depending on when you started investing. I was very lucky to have started angel investing in 2008 during the Great Recession as a Scout for Sequoia Capital. 

At that time the valuations for startups like Uber and Thumbtack were $10m — combined! 

For the past couple of years, startups run by founders who aren’t qualified enough to make a cup of coffee for Travis and Marco were demanding $15m valuations for copycat ideas with anemic performance. 

A hot market filled with easy money makes everyone think they should start a company — which is completely reasonable. 

I believe that we’re headed back to 2008-2010 valuations this year and it’s going to be fantastic for angel investors who are brave enough to place bets. 

Nothing is guaranteed, and you can insert a bunch of financial disclaimers here, but candidly I’m planning on being more active in the next 12 months than I have been in my 10-year history as an angel investor. 

If you’re rich and bored, or maybe even retired and regretting it, I would like to make the case for you to become a half-time or full-time angel investor. 

Now, I don’t think you should invest 100% of your capital in startups this year.

However, I think rich people (aka accredited investors who have capital available) who become full-time angel investors this year should build an intelligent plan to deploy a fraction (1-10%) of their net worth. 

Essentially, the amount they can afford to lose. 

In my book ANGEL I explain a way to do this intelligently that goes like this: 

  1. You want to make 30+ investments so you have a chance at an outlier. 
  2. You want to only invest in startups that have products in market and revenue already — and there are thousands of them. 
  3. You want to make very small bets when you start and then go 2-10x on the winners. 
  4. You want to make those 30+ investments over a three-year period. 

Here’s some basic math on the plan I recommend.

  1. You have a net worth of $10m. 
  2. You allocate $450,000 for angel investing. 
  3. You invest $10,000 into each of the 30 startups ($300,000). 
  4. You invest the final $150,000 into your top five startups ($30,000 each).

In this model, $200,000 of your $450,000 invested will go into the top five startups. 

You can assume in this hypothetical model that you will get $0 from the 25 you didn’t follow on with, and then if one of the other five pays off 25x on the initial investment ($10,000 * 25x = $250,000) and 10x on the second investment ($30,000 * 10 = $300,000) you are in the black already. 

This is not guaranteed, obviously, but if you talk to folks in Silicon Valley with over 30 angel investments you hear stories of outlier investments and power laws often.

In this example, if you lose it all, you lost 4.5% of your net worth, which is not fun but is survivable (heck, if you’re in the markets right now you’ve probably experienced “losing” 20% of your net worth in a week or two). 

You can strategize various scenarios for angel investing based on your time frame, goals, chip stack, age, dedication level and risk profile.  We discuss all of this in the Angel.University course. 

Just two examples from our investments:

  1. Calm is valued at 153x for us.
  2. Uber, an outlier of all outliers, is 2,000 to 4,000x+ (depending on when/if you sold).

If you want to learn how to become an angel investor, come to a virtual edition of Angel.University which we will host on April 7th. 

We have 100 slots for accredited investors, apply here: http://angel.university 

We are asking for a suggested donation of $100 per person for Angel.University: 100% of which will be donated to coronavirus-related causes like https://feedingamerica.org and https://covid19responsefund.org 

In short, based on my experience, the next six to 12 months could be the best time to start angel investing since the Great Recession. 

I could be wrong, this crisis could last a couple of years or as short as three months, but I know that angel investing is an amazing vocation if you’re passionate about entrepreneurship, technology, and innovation. 

Early-stage startups will be on sale as capital markets constrict and funding sources slow their pace of investing and lower their slug sizes.

Fortunes are made in the down market and collected in the upmarket. Let’s get to work. 

All the best, Jason

The post Now is the best time to be an angel investor (let me show you how) appeared first on Jason Calacanis.

How to Say “No”: Five Templates to Turn Down Opportunities Gracefully

https://calacanis.com/2019/10/21/how-to-say-no-five-templates-to-turn-down-opportunities-gracefully/play episode download
October 2019, by Jason Calacanis[ —]

Kevin Rose and Tim Ferris did an episode of The Random Show [https://overcast.fm/+RxHE2g-PI] where Tim Ferris confessed that he had cancelled his next book and refunded the advance. The book he said “no” to was about “how to say no,” which is ironic and something that any super router like Tim or Kevin has to deal with at an acute level.

[ Click to Tweet (can edit before sending): https://ctt.ac/7dEea ]

For kind folks who get famous, saying no is a non-stop burden, but saying no isn’t just critical for the mental health of famous authors or podcasters, it’s something that founders have to be ruthless about because the startups that succeed are, universally, the ones that scale a single product and business model (Google:Search, Uber:Rides, Facebook:Social Network, etc.) — at least in their first five to ten years. 

As an investor in over 200 startups, I’m constantly having founders text me their new, crazy ideas — after having just invested in their last one. Sometimes it’s great to pivot, hard or softly, into a new product, but saying no to distractions and new ideas is often how you have a big breakout success.

Here are the templates I use. Feel free to share and remix them. 

The “Not Right Now” List

In your own company, people will come to you with a ton of ideas, strategies and tactics, which are three very distinct things. Once in a while some folks will even want to change or edit your mission (the highest level structure in your startup). 

When they do, a great response is the sh@#$t sandwich structure: “Great idea. Let’s put it on the ‘not right now’ list so we don’t forget it — since it’s so good!”

Bread: “great idea” and “so we don’t forget it — since it’s so good”

Sh@#4t: Obviously, we’re not doing this right now. We need to stay focused. 

Defining Your Zone

People will want to engage you and your business to solve their problems. This is only natural, so it’s important to frame for people what you do and don’t do. In my life as a publisher I would tell folks who “wanted to get lunch” or “discuss how we might collaborate” with a simple email template:


Thanks for reaching out, really appreciate you thinking of us! There are three ways to get involved in Silicon Alley Reporter magazine:

  1. Subscribe here: URL
  2. Advertise in the publication: meet Jane, cced, who runs advertising.
  3. Be featured: We don’t take pitches from PR folks, but send updates on your business to the tip line here.

Don’t have time for lunch right now as I’m on deadline for the next issue, but happy to answer any other questions you might have over email. 

Editor & CEO, Silicon Alley Reporter” 

For my role as an investor, I have a similar email.


Thanks for reaching out! Please meet Jacqui Deegan, cced, the Managing Director of the LAUNCH Accelerator (launchaccelerator.co), which is where we engage with founders at the early stage.

Frequently asked questions here: https://launchaccelerator.co/faq

If you could send us your deck, traction (revenue by month since inception in a chart or table) as well as your funding history, that would be very helpful.


Some folks will of course say, “I’m not interested in coming to your accelerator, but would you have lunch with me and give me $1m in seed funding for my idea?” or “We are past the accelerator stage and have $10,000 a month in revenue.” 

To which I will explain: 


You’re a bit too early for us, but do keep us up to date by sending your monthly updates to investors to updates@launch.co

Our syndicate (http://thesyndicate.com) reviews seed-stage/Series A/Series B companies with $50,000+ a month in revenue, doubling every six months or less. Ashley is the MD of the Syndicate and can answer any questions.


Now, we will obviously invest in some startups that are pre-launch (i.e., Superhuman) or have very modest traction (Calm.com had $10,000 in total revenue when we invested, I think), but having some basic sorting guidelines frees us from wasting the founder’s time. We will review their product and deck before responding so if something looks wildly interesting we’ll take a deeper dive, but when things aren’t a fit for us, we will still make it really simple for incoming founders to engage with us.

Blank “On Deadline” Reply

We’re all working against some deadline, so being able to have a standard “on deadline” response is important for requests. I’ve used one that encourages any follow-up questions over email, and another one that puts a hard no on it.

“Thanks for reaching out. I’m on deadline for my next book and don’t have time to meet, but I’m happy to try and answer any questions you have over email. 



“Thanks for reaching out. I’m on deadline for my next book until April 15th 2020, and I won’t have time to meet or review this opportunity. Thanks for thinking of me. 


The “I Don’t Do” BLANK 

Knowing what you don’t do is critical. I often, for example, get asked to fund movies, restaurants, albums and non-profits. I have a simple response for that, too: 

“Thanks so much. While I do enjoy films/restaurants/music immensely — I do not invest in them! 


Use Superhuman Snippets 

I do all of this with Superhuman Snippets, which lets me reply and cc folks automatically when using these templates. Superhuman doesn’t let me share the templates with team members or label the emails yet, but those two features will be killer when they do arrive. 

Giving a quick “no” is compassionate to other folks because it lets them move on quickly. Also, taking the time to build your own “I don’t do… BLANK“ list is critical if you want to achieve greatness — which is often defined equally by what you don’t do as what you love doing.

Once again, listen to the podcast with Tim and Kevin here: https://overcast.fm/+RxHE2g-PI

The post How to Say “No”: Five Templates to Turn Down Opportunities Gracefully appeared first on Jason Calacanis.

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