Finding “Unicorns:” Questions to Ask Before You Invest in a Startup

Jason Calacanis (@jason) has actually made 125 early-stage startup financial investments and selected 6 “unicorns” (start-ups to go beyond $1B in assessment)– one out of every 21. Based on his AngelList profile, Calacanis financial investments consists of: Tumblr, Cozy, Thumbtack, Rapportive, Uber, Chartbeat, Groundcrew, Evernote,, Nimble, Crossfader, Signpost, Calm, numerous a lot more. Hes accelerating his implementation of capital and prepares to purchase an extra 150 start-ups over the next 30 months.

Im going to take you through the 4 most crucial questions I ask all creators. The goal of asking these questions is not just for you to comprehend the business however also so you yourself can respond to 4 critical financier questions:.

The following guest post is a special excerpt from his new book, Angel: How to Invest in Technology Startups– Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000. Using stories from his own angel investing profession, Jason wrote this book as a playbook for striving angel financiers.

In specific, this post focuses on questions to ask founders before you invest, but it also serves as a tutorial on how to ask much better concerns in life and in organisation.

Numerous individuals ask me about start-up investing and how to start.

Meeting founders for an hour is the most regular method for angels to decide who to buy, but certainly not the only one. There are some angels whose primary strategy for picking investments is to follow other smart financiers, preparing off of their conferences and offer flow.

The life of an angel is everything about handling a deal funnel, which includes three distinct steps: sourcing offers, assessing offers, and, finally, choosing which founders youre going to fund.

Another method is just to evaluate the core metrics and decide based upon those. This can be done by evaluating a deck or by checking public information sources, like the App Store rankings, and traffic monitoring services, like Alexa and Quantcast.

This post– while for informational purposes just and not investment recommendations– is meant to reveal you how one successful investor approached the early-stage game.

Some investors have a substantial Rolodex and merely purchase the founders they already understand, a method that worked incredibly well for financiers who knew Elon Musk (Zip2 and PayPal prior to Tesla and SpaceX), Evan Williams (Blogger prior to Twitter), and Mark Pincus (Freeloader and Tribe before Zynga).

Meetings are totally free and essential. 10 one-hour meetings a week is a great target for an expert angel.


When it comes to writing checks, my best recommendations to you as you begin dating is to be promiscuous with meetings– but a prude. Dont be a tramp like I was.

Enter Jason.

Naturally, the “invest in who you understand” approach would suggest you missed out on the most significant start-ups in history: Mark Zuckerberg, Bill Gates, Evan Spiegel, and Larry Page, who all struck the ball out of the park on their very first try– at the ages of nineteen, twenty, twenty-one, and twenty-five, respectively.

Why has this founder picked this service?


Your task in these conferences is to play Columbo, the simple and always undervalued investigator from the timeless TV show that started in the 70s and ran for more than 3 years. Your task is not to flaunt or demonstrate how clever you are by explaining to the creator what theyre doing wrong or by bragging about your heroics as a financier or, even worse, as a founder yourself.

This is why, when you speak to your therapist about your mommy, they say “hmm …” while tilting their head and taking a look at you with sympathy. They add, “Tell me more about your mother,” or “Unpack that some more,” or merely “Your mother …”.

How committed is this creator?
What are this founders possibilities of succeeding in this business– and in life?
What does winning look like in regards to revenue and my return?

Youll have more hits and fewer misses.

There are 6 words, four words, and two words in those responses. The last one is the most effective due to the fact that it simply hangs there, inviting you to construct on the topic.

If individuals think they are being deeply listened to, they will talk more.

Basically, if you shut your trap and listen like a therapist or a detective, youll have the ability to uncover the responses to those 4 questions better than other angel investors.

You desire to be Dr. Melfi, Tony Sopranos therapist, sitting patiently while the enthusiasm and discomfort pour out from the one in charge youre fulfilling with. If youre a terrific listener, you will be a great financier, in addition to an excellent good friend, an excellent moms and dad, and an excellent person.

You desire to have big ears and a little mouth in these meetings. You wish to ask concise questions that take no greater than a number of seconds and then listen deeply to the answers, considering them with every fiber of your consciousness as you write your notes on paper– similar to Columbo.

Second, if you are hyper-present in the meeting, thinking deeply about the founder and why they are taking on the unreasonable pursuit of starting a company, which includes a higher than 80 percent chance of failure and a 100 percent opportunity of suffering, then you will have the ability to make a better choice on whom to purchase.

Listening like this will serve two virtuous goals, the very first being that the founder will feel heard and comprehended by you.

When you are starting a creator conference, ask one icebreaker question to get your subject heated up.


How do you understand Jane?

These are the precise 4 questions I ask every creator. The responses to these questions will offer you many of what you require to make your investment decision.

I have a video game where I attempt to say things with as couple of words as possible due to the fact that it reminds me that this conference is not about me, its about them. It likewise makes me sound smart, like Obi-Wan or a Toshiro Mifune character.

If you were presented to this creator by a mutual connection, you can rapidly develop commonalities by asking these five easy words. Listen to the answer you are provided and construct a follow-up concern based on their response. If the founder said that they worked with Jane, your next move is to state, “You worked with Jane? What was that like?”.

1. What are you working on?

The reason I phrase this concern as “What are you dealing with?,” versus something more company-specific, like “What does Google do?” or “Why should I invest in Google?” or the very awful “Why do you believe Google is going to be successful after eleven search engines have currently failed?,” is that it commemorates the creator (the “you”) and what founders do (the “work”). It reveals that you have deep empathy and you acknowledge that this isnt about what the thing does (Google assists you find things), however rather its about individuals (Larry and Sergey write software application that helps people discover information quicker).

2. Why are you doing this?

While there have actually been some effective start-ups constructed by running ahead of market leaders, in general, those sort of start-ups get crushed or bought for small dollar amounts. Summize was an online search engine for Twitter, back when Twitter was so technologically incompetent that they might barely keep the service online. They bought Summize to capture up, in addition to TweetDeck, an advanced client for checking out several feeds simultaneously, but the return to the financiers in Summize and TweetDeck for these acquisitions were minor when compared to the returns of the company that purchased them.

Much like Columbo, Im trying to find killers and Im attempting to get rid of suspects.

There are some truly, truly bad responses to the concern “Why are you doing this?” The worst 2 responses, which youll hear often, are “To generate income” and “Because INSERT-SUCCESSFUL-COMPANY-NAME-HERE does not do it.” They will eventually give up when they understand there are numerous better ways to make money faster and with more certainty if folks are building a start-up for cash. If you wish to make a lot of cash, youre much better off being a world-class programmer on a extremely esoteric and sought-after vertical and getting Google or Facebook to provide you $1 million-plus a year in stock and money for 10 years in a row. You have no disadvantage, you can work a number of hours a day, and you get endless totally free food.

Consider that for a second: Is there anything more vital than procreation? Not according to Darwin or Freud, so Zucks absence of game resulted in the fastest-growing consumer item in the history of mankind, mainly based upon individuals requiring to find a mate or to get in touch with previous lovers (as shown by the variety of divorces that point out Facebook in their filings).

Elon Musk didnt develop a battery pack: he built a vehicle and ultimately an energy option that included solar, home batteries, and, possibly when you read this, a ride-sharing service like Uber.

If youre developing something because another hugely successful business doesnt currently have that feature, well, youre extremely ignorant or, usually, plain old foolish. For several years people pitched me on start-ups that were allegedly going to be Google look for news, Google look for video, and Google look for books and magazines. We all understand how that ended up.

The huge problem with “founders” who build a function that a market leader will inevitably get to– and I use quotes here for a factor– is that they lack vision. The act of choosing a feature as their lifes work, as opposed to a full-blown product or an objective, disqualifies them from being a true creator.

More recently Ive been pitched hard on “Uber for food,” “Uber for helicopters,” and “Uber for shopping.”.

Its alright to start little, but its not okay to be a small thinker.

Once again, 5 simple words that are concentrated on the creator. When I ask these very first 2 concerns, I nearly universally see creators merge their chairs. They unwind, let their guard down, and seem like I appreciate them, which I do. Much like Columbo cares deeply about the suspects hes speaking with when he asks, “So, what do you do here?” when he walks into their office, rather than leading with “Where were you on the night of the murder?”.

Zuckerberg was awkward with the girls, so he constructed a social network that would reveal him their relationship statuses.

Travis Kalanick and Garrett Camp constructed Uber due to the fact that they couldnt get a cab in Paris at a technology conference. Elon Musk built SpaceX due to the fact that he desired a backup plan for mankind.

3. Why now?

He replied, “Youre going to do sixty stories at CES?”.

This question has actually been drifting around the Valley for a while, and the first time I heard it was from my friend, Sequoia Capitals Roelof Botha– the endeavor capitalist who convinced me to end up being a “Scout” for their company, which resulted in my two greatest financial investments to date: Uber and Thumbtack.

In some methods, “Why now?” is the most important question about the business you can ask because there are numerous folks continuously trying the very same concepts over and over once again in our business.

Its not who gets there. Its who gets there first when the markets prepared.

He asked me how many individuals we had at the show and I said fifteen. His jaw dropped and he asked me how frequently they were submitting, and I said four times.

For Uber it was basic: smart phones were ending up being common and they had GPS. Another company had already attempted to help you buy a taxi by means of SMS messages a year prior to Uber came on the scene. Their “why now” was simply “text messaging,” however that, frankly, wasnt enough. Without sophisticated mobile CPUs (central processing units) to power huge lovely touch screens with military accuracy GPS (worldwide positioning system), there would be no Uber.

There were dozens of video business before YouTube, but they all charged people for bandwidth and storage, which indicated that if you wished to publish a video on the web, your benefit for going viral was a ten-thousand-dollar server bill. Instead, YouTube sends you a thousand-dollar check from the advertisements they operate on your hit video.

Founders tend to have these “Why now?” insights without acknowledging how profound they are. When I started my blogging business, Weblogs, Inc., in 2004, I had a very simple thesis: I thought that terrific brand-new authors releasing 5 brief, unfiltered posts a day would get more readers than recognized reporters composing one story, modified by a half dozen individuals, as soon as a week.

He stated they had three journalists at the show and they would do two or 3 pieces each over the next month. So, they were doing six stories and we were doing sixty a day for 5 days– 3 hundred overall.

If you unload this concern, youre really asking, “Why will this idea succeed now?”.

For YouTube, which had Roelof Botha as its first investor, the “Why now?” was a confluence of elements and breakout successes that tend to be born during these perfect storms. First, bandwidth costs plunged after the dot-com crash. Second, storage expenses were dropping due to this brand-new thing called cloud computing. Third, blogging was taking off. Countless folks were writing 10s of countless posts each week and YouTube used a smart way to embed their videos on other individualss sites– reaching a massive audience for totally free.

Dropbox, which introduced onstage at the very first year of my LAUNCH Festival and was also funded by Sequoia Capital, had the very same “Why now?” as YouTube: plummeting bandwidth and storage costs.

I stated, “Actually theyre posting 4 times a day. So sixty stories … daily. How often is your team filing?”.

4. Whats your unjust advantage?

Often, creators will not have an answer for this question. Whichs alright. This is one you frequently end up answering while looking in the rearview mirror.

Said another way, this concern is asking, in just four words, “What makes you uniquely qualified to pursue this service? What tricks do you understand that will help you beat both the incumbents and your quick fans?”.

Creators with breakout start-ups typically have an unreasonable advantage. Google had their Stanford connections, filled with gifted algorithm-writing engineering geniuses. Facebook released while Zuckerberg was still a trainee at Harvard, and they utilized their understanding of school culture and directories to find out the characteristics of constructing online social media networks that scale. Mark Pincus introduced Zynga with a multi-year cross-promotion offer with Facebook, which allowed Zynga to accompany with Facebook as it grew at an astounding rate. Mary Gates was on the board of United Way with the CEO of IBM, which led straight to IBM hiring her son Bills new company, Microsoft, to build the os for their very first desktop computer.


These four creator questions give you a great starting point for answering the 4 investor concerns every angel needs to ask themselves prior to investing. Remember, we wish to determine:.

After asking these 4 creator questions, which in overall are sixteen words, you need to have an excellent concept of what this person is constructing and why.

Why has this founder selected this service?

Associated and Recommended.

The Tim Ferriss Show is one of the most popular podcasts on the planet with more than 500 million downloads. It has been chosen for “Best of Apple Podcasts” three times, it is frequently the # 1 interview podcast across all of Apple Podcasts, and its been ranked # 1 out of 400,000+ podcasts on numerous occasions. To listen to any of the past episodes totally free, take a look at this page.

What you probably wont know are the tactical details of how they intend on performing on their vision, including their go-to-market technique, what type of team they have, the competitive landscape, and the subtleties of their organisation design.

After half an hour and four concerns, youre going to have a strong sense of why the founder picked this company, why it may work today, and, obviously, what they are developing.


If you were introduced to this creator by a shared connection, you can quickly establish common ground by asking these 5 simple words. These are the specific 4 concerns I ask every founder.,” is that it commemorates the creator (the “you”) and what creators do (the “work”). When I ask these first 2 questions, I almost generally see creators melt into their chairs. Sometimes, creators will not have a response for this concern.

You are going to discover the answers to those questions in the 2nd half of your meeting. This is the foundation.

For more information about Jasons method to investing, and the stories behind his greatest wins, inspect out Angel: How to Invest in Technology Startups– Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000


How committed is this creator?
What are this creators possibilities of prospering in this company– and in life?
What does winning appear like in terms of income and my return?


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