Pitching Posts

We’re teaching our first ever online workshop about “How to pitch investors” on eduFire — a platform for live video teaching online. Sign up here. I’ve taken classes on eduFire and it works really well; here are some recordings of their classes.

(Update: This class is full so I’ve opened up a second class. Sign up here.)

(Another update: The second class is also full. E-mail me to get on the waiting list for the next class. And if you want to buy a recording of the class, e-mail me or contact me on eduFire. We obviously won’t be able to work on your pitch with a recording, so it’s half the price ($49).)

What you’ll accomplish

You could be building the next Google — but investors won’t know it if your pitch doesn’t sing. You’re going to “walk” out the workshop with:

  • A great pitch for your startup.
  • A list of things your startup will need to accomplish before you can raise money.
  • An understanding of the fundamentals of pitching so you can revise your pitch anytime and teach your friends how to do it.
  • A copy of our Pitching Hacks e-book.

First we’ll cover the fundamentals:

What investors want to see
How to get intros to investors
High-concept pitches
Elevator pitches
Decks and presentations

Then we’ll work on your pitch as a group. You’ll get lots of hands-on advice from me and other students. I’ll also be sharing some of my latest pitching techniques which we haven’t published anywhere.

This is the first time we’ve ever done anything like this and I’m psyched.

Time and Cost

The workshop costs $98 (just like Wal-Mart) and there are only 3 2 slots left (uh, somebody signed up while I was writing this). It consists of 2 sessions on Tuesday Nov 3rd 5-6pm Pacific and Thursday Nov 5th 5-6pm Pacific. You go to both sessions. Sign up here.

(Update: This class is full so I’ve opened a second class on Wed Nov 4th 1-2pm Pacific and Friday Nov 6th 1-2pm Pacific. You go to both sessions. Sign up here.)

(Another update: The second class is also full. If you want to buy a recording of the class, e-mail me or contact me on eduFire. We obviously won’t be able to work on your pitch with a recording, so it’s half the price.)


We’ve helped startups raise tens of millions of dollars from investors like Sequoia, Benchmark, Bessemer, etc. See the reviews of our pitching advice from entrepreneurs like Adam Smith at Xobni and Jonathan Grubb from Get Satisfaction.


The only prerequisite is determination. You’ll be even better prepared if you read the fundamentals above.

Contact me on eduFire or email nivi@venturehacks.com if you have any questions and sign up here.

Pitching Hacks is here. The PDF is $29 and you can download it immediately. 83 pages. Buy it here. Fuck that, it’s free.


We’ve raised $100 million for startups like Epinions, invested another $20 million in companies like Twitter, and advised many others. Pitching Hacks shows you how to apply the simple lessons we’ve learned along the way. Check out these samples:

Table of Contents
Why do I need an introduction?
Can I get investors to sign an NDA?

Many successful investors and entrepreneurs like Marc Andreessen, David Cowan, and Brad Feld have generously contributed passages sprinkled throughout this weighty tome.

Many of the ideas in Pitching Hacks first appeared on this blog — that was our first draft. Thanks to your feedback, we’ve written this book — a second draft. Please send us more feedback — so the next revision is even better. You can always reach us at team@venturehacks.com.


Thanks to the beta testers who paid to give us amazing feedback (check your inbox for a revised copy!). They made the book much better. Here are some of their (unsolicited) testimonials:

“Your first stop if raising money!” – Adam Smith, Xobni

“Almost every sentence in Pitching Hacks is a valuable nugget. I thought the book was *awesome*, and definitely up to the high standard of quality that you’ve already established in your blog.” – Travis Leleu, Industrial Interface

“Pitching Hacks is amazing, just packed with great practical advice. A must-read if you’re even thinking of raising money.” – Luke Groesbeck, JobAlchemist

“I loved the book!  I suppose it should be no surprise that a book about articulating ideas clearly and concisely, has managed to clearly and concisely articulate its ideas.” – Aaron Iba, EtherPad

“I really truly liked the book. Entertaining and informative read. Can’t say that about a lot of business-related books.” – Yokum Taku, Wilson Sonsini

Raising money is like finding a black swan.

It seems like you will forever keep hearing “no”, “let’s keep talking”, or “find a lead.” Or worse, you sign a term sheet and it blows up before you can close it.

It seems like you’ll never raise money, until one day—boom—you meet the right investor, he says yes, you negotiate a deal, and suddenly there’s money in your bank account.

What’s a black swan?

A black swan is a highly improbable, high impact, and unpredictable event. Nassim Nicholas Taleb popularized the idea in his book, The Black Swan: The Impact of the Highly Improbable.

9/11 was a black swan. It was hard to predict, it was highly improbable, and it changed the world—black swans define the future.

Once you see enough white swans, you start assuming all swans are white—until you see a black one. Once you get enough nos, you start assuming every investor will say no—until you get a yes.

The nos don’t matter.

The chances of raising money are low. You don’t know when or if it will happen, who will invest, or how much you will raise.

(The exception to this rule are the chosen ones: “obviously” fundable companies that are founded by successful entrepreneurs, companies that are making money by the truck load, or have cured cancer, or whatever.)

There will be no precedent for a yes. If someone looks at your string of nos, they won’t suggest that you’ll get a yes tomorrow—they’ll predict more nos. But just because you’re getting a lot of nos today doesn’t mean you will get a no tomorrow. The past is an indicator of the future—up until the moment you find a black swan.

If you’re looking for a black swan, ignore the nos.

Searching for black swans can be a big waste of time.

I’ve seen an entrepreneur sleep on my couch for months while he tried to raise money. It seemed like he had no hope—until he suddenly raised money from Big Firm X.

Many entrepreneurs implicitly understand this. They know that raising money is rare, unpredictable, and important to their business. So they spend months and months searching for a black swan.

But perpetual fund-raising is a bad way to raise money. Investors like to invest in working businesses—which means you need to work on the business—not spend the next 6 months raising money.

The problem with black swan processes is that they don’t always yield black swans. Sometimes they just give you white swans until you or your company dies. Black swans aren’t guaranteed—they’re the opposite of guaranteed: low probability and unpredictable.

How to find black swans.

Here are a few ways to search for black swans:

  1. The Chosen One Strategy: Wait until you’re obviously fundable before you raise money. Keep building value until investors come to you.
  2. The Hobby Strategy: Keep working on the business while you raise money as a hobby. Spend less than 25% of your time fund-raising so you can focus on activities that have a greater chance of creating value.
  3. The Efficient Strategy: Raise money full-time and test the market very efficiently through focus, timeboxes, and lessons learned.

The Chosen One strategy is the best if you don’t need the money right now. Instead of trying to solve the black swan problem, this strategy dissolves it. If you do need the money right now, stop and seriously think about how to build the business without the money—remember, fund-raising is low probability and unpredictable if you’re not one of the chosen ones.

The Hobby strategy is awful. Don’t even bother—just work on the business instead. Raising money is a full-time job for at least one of the founders. If possible, also get your co-founder on the job part-time, so you can pair, like detectives trying to solve a crime.

The Efficient strategy is the best way to find black swans if you can’t or won’t execute the Chosen One strategy. There are three pieces to this approach: focus, timeboxes, and lessons learned.

1. Focus

Raise money full-time.

Pick up the phone and get introductions to investors from middlemen. Call in every favor you have and explain why the middleman will look good by making an introduction. Get the middleman to focus on making a single great introduction. Three weak email introductions won’t do anything but one strong phone call might.

This is a lot of work just to get 10 or 15 introductions. And you haven’t even met any investors yet. That’s why we say fund-raising is a full-time job.

2. Timebox

Put time limits on each step of the fund-raising process.

If you aren’t getting good introductions in 1-2 weeks, quit fund-raising and start executing Plan B. If you aren’t getting good meetings in 3-4 weeks, quit fund-raising and start executing Plan B. If you aren’t doing partner’s meetings in 5-6 weeks, quit fund-raising and start executing Plan B. If you aren’t signing a term sheet in 7-8 weeks—you know what to do.

And don’t start raising money until you have a Plan B—a Plan B is the simplest way to create a deadline and scarcity by fiat.

3. Lessons Learned

As you raise money, get honest, high-quality feedback from investors, advisors, etc. Once you get enough feedback and nos, stop raising money, fix your team, product, market, and traction, and try again.

It’s hard to get high-quality feedback from anyone period. Most people, even effective ones, don’t give good advice. Honest feedback from investors is particularly hard because they don’t like calling your baby ugly.

Try saying something like this when you get a no:

“Thanks. Yeah, I completely understand. We want to make this business work. What would we have to accomplish to make this business interesting to you?”


One more thing. Optimism: you can’t raise money without it. The most effective way to stay optimistic is to find the right wife for your startup (also known as a co-founder).

Fund-raising isn’t a part-time job. It’s a black swan that you should avoid entirely or chase efficiently with focus, timeboxes, and lessons learned.

What do you think?

Summary: Pitches usually fail because they answer the wrong questions. The right questions depend on the stage of your business—for example, some businesses are just getting started with an idea, while others are printing money. Focus your pitch on the key questions for your stage and if you keep getting non-key questions, something is wrong with your pitch. This post includes a hierarchy that you can use to classify your business and the key questions for each stage in the hierarchy.

[Ed: This is a guest post by Eric Ries, a founder of IMVU and an advisor to Kleiner Perkins. Eric also has a great blog called Startup Lessons Learned.]

Every company will need to pitch itself from time to time. Usually we think of pitches in the context of raising money, but that is only one of many pitch situations. We pitch to potential partners, vendors, publishers, conferences, employees, and even lawyers.

Pitching is different from selling a product, because it is not part of our regular business practice, it is not something that relates to our core competence, and it tends not to happen in a repeatable and scalable way. (I’ll exclude those non-lean startups who basically exist for the purpose of raising bigger and bigger sums of money. You’re not one of those are you?)

Pitches usually fail because they answer the wrong questions.

Most of the times I have seen pitches fail, it is not because they are poorly written, or that the entrepreneur lacks passion. It is because they don’t answer the right question.

My favorite example of all time comes from students in an entrepreneurship class. Their idea was to build a next-generation autonomous robot, that could be used by defense and security agencies around the world. The whole pitch was about how valuable robots could be in the future. They even included a slide with The Transformers on it.

Now there was nothing wrong with their analysis: anyone who invents a technology as sophisticated as The Transformers is definitely going to make a lot of money. But these students completely failed to address the one and only question on their audience’s mind: can you three guys really build the robots of the future? (Turns out, they were incredibly well-credentialed graduate students who had, in fact, developed some interesting new robotics technology. But you wouldn’t have known that from their pitch.)

The right questions depend on your business’ stage.

I have come to believe that there is a hierarchy of pitches, and that understanding where your pitch falls in this hierarchy can assist in making decisions about what information to highlight. Pitches that sit higher in the hierarchy tend to be more successful, and if you can fit your company into one of those categories, you can get better results or better terms.

Now, just because you can do a thing, doesn’t mean you should—there are plenty of other great resources, like Paul Graham’s essays, that can help you think through whether and when to raise money (or do other kinds of deals).

With that disclaimer out of the way, here’s the hierarchy of pitches:

  1. Printing money.
    Key questions:
    Are those numbers real? How big is the market? Can your team execute the growth plan?
    Most important slide: Valuation.
  2. Promising results.
    Key questions: Can you monetize that traffic (or drive traffic to that profitable destination?) Do you know why you’ve achieved those results?
    Most important slide: Hockey stick.
  3. Micro-scale results.
    Key questions: Who is the customer, and how do you know? What is the potential market size? What are the business economics?
    Most important slide: Lessons learned.
  4. Working product.
    Key questions: What does the product do? What’s the launch plan? Who’s on the marketing team?
    Most important slide: Live demo.
  5. Prototype product.
    Key questions: What will it take to ship a working product? How do you know anyone would want it? Who’s on the engineering team?
    Most important slide: Demo (if the product solves an obvious problem), engineering resumes (if the product is nearly impossible to build), or “a day in the life of a customer” (if neither of the above).
  6. Breakthrough technology.
    Key questions: Who owns the patents? Can we make a product out of this technology? Are there any good substitutes?
    Most important slide: Barriers to entry.
  7. All-star team.
    Key questions: Has the team made money for their investors in the past? Are they domain experts? Are they committed to an idea in their domain of expertise?
    Most important slide: Problem we are trying to solve.
  8. Good product idea.
    Key questions: What kinds of risk does this company need to mitigate (technology risk, market risk, team risk, funding risk)? Is it a revolutionary and novel idea? Is this team the one to back? Can the team bring the product to market? Who is the customer? Who is the competition? Will they fail fast?
    Most important slide: About the founders.

[Ed: Here’s another way to think about the key questions and most important slide. The key questions should describe how you will get to the next stage of the hierarchy. And the most important slide should prove that you’re at the stage you claim to be.]

Focus your pitch on the key questions.

In a pitch meeting, try to spend as much time as possible talking about the key questions for your pitch. If you find yourself getting asked non-key questions, try to use your answers to steer the conversation back to the key questions.

But here’s the most important part: if you keep getting non-key questions over and over again, something is wrong with your pitch. Either you misunderstand where your pitch fits into the hierarchy, or you are not using the early part of your pitch to establish it.

Don’t keep banging your head against the wall—if you can’t convince your potential partners that your startup is printing money, try to figure out why. Experiment with different narratives. If you still can’t do it, move one level down the hierarchy and see if you can make that story stick.

Don’t try to cram cogent arguments into the slides of your deck. Keep the slides simple, visual, and minimal. Put cogent arguments, talking points, and prose in the notes that accompany each slide.

How? Check out Dan Cook’s Laws of Productivity (pdf) for a great example:

(If you don’t see the embed above, see The Laws of Productivity on Scribd.)

You now have a deck that you can send in emails or present in person. An investor can read the slides and notes and imagine a presentation. And you can present the slides while you refer to the notes. Bon Appetit.

Watch the master pitch man, Steve Jobs, analyze the market for NeXT workstations in Part 1 of his Chalk Talk. He explains:

“Who is our target customer? Why are they selecting our products over our competiton’s? And what distribution channels are we going to use to reach these customers?”

Steve covers a handful of the slides that you see in a typical startup deck: Marketing, Sales, Competition, and a little bit of Problem and Solution. We should all strive to present with Steve’s clarity and simplicity.

Here’s part two of the video. Thanks to Daring Fireball for pointing me to this video.

Summary: If you’re having trouble writing an elevator pitch, try using bullets. And challenge yourself to keep the pitch under 100 words.

I received a cold call elevator pitch yesterday that was very effective. It was short (88 words not including the signature), the company had good traction, and the author used bullets to make his case (4 out of 5 bullets were about traction). Here it is (with the author’s permission):

Subject: Cold emai [sic]

A quick “cold email” to see if you would be interested in helping X raise money.

Our Story

  • We are the the X of Y
  • Over X Million registered users
  • Growing at X new users per day
  • Projecting growth at X new users per day in next X days
  • Zero cost per customer acquisition

If you are interested please contact me 🙂


The prose, spelling, and formatting could use a little work, but the pitch was brief and effective. I’m going to follow up with him.

Later that day, I was helping a client refine his elevator pitch. We were stuck on the prose so we decided to try bullets and it worked well. Here’s an example:

Subject: Introducing Ning to Blue Shirt Capital

Hi Nivi,

Thanks for offering to introduce us to Blue Shirt Capital. I’ve attached a short presentation about Ning. Here are some of the highlights:

  • Ning lets you create your own social network for anything. For free. In 2 minutes. It’s as easy as starting a blog. Try it at http://ning.com
  • We have over 115,000 user-created networks and our page views are growing 10% per week.
  • We previously raised $44M from Legg Mason and others, including myself.
  • Before Ning, I started Netscape (acquired by AOL for $4.2B) and Opsware (acquired by HP for $1.6B).

We’re building Ning to unlock the great ideas from people all over the world who want to use this amazing medium in their lives.

I’ve admired Blue Shirt’s investments from afar. We’re starting meetings with investors next week and I would love to show Blue Shirt what we’re building at Ning.


Marc Andreessen

Not bad. But at 158 words (not including the signature) it’s almost twice the size of the cold call I received today. Compare this Ning pitch to Ning’s pitch without bullets. Which one do you like better?

John Manoogian sent me this great trailer for The Player, a satire of the movie making system in Hollywood:

(Link: The Player)

Silicon Valley is the Hollywood of startups.

Business plans are scripts, entrepreneurs are writers, engineers are talent, VCs are studios, angels are independent financiers, recruiters are casting agents, lawyers are lawyers, advisors are agents, points are options, TechCrunch is Variety, and so on.

What analogies am I missing?

I want to give Pinch Media a shout-out for mentioning our post on high concept pitches in their funding announcement. Their pitch is,

“FeedBurner for iPhone developers.”

Can they shorten it even further? “FeedBurner for iPhones”?

I wonder if they used our other hacks too when they negotiated their deal with Union Square Ventures and First Round Capital. (Mobile analytics must be picking up steam; Motally just joined Venture Hacks—they “track and report usage statistics across mobile websites.”)

Some people think high concept pitches are too simple. I agree, they are too simple—that’s the point. They’re the beginning of a conversation, not the end of one.

There are too many startups vying for too little attention. You simply won’t have the opportunity to tell your whole story at once. A high concept pitch is a meme that you use to capture some attention, so you have the chance to tell the rest of your story.

Marc Hustvedt, an angel investor on Venture Hacks, calls the high concept pitch a “Hollywood pitch”. I like it. “Hollywood pitch” is shorter and more concrete. Which one do you prefer?

Anthony Stevens read our article on high concept pitches and decided to write a high concept pitch for his startup:

“So, let’s see: my startup is Crowdify, a tool for brand and reputation managers to discover new insights into consumers’ attitudes about their subjects and make better decisions about marketing and public relations strategy. We do this through semantic analysis applied to consumer-generated correlations among and between brands and reference data. Further, we utilize social-networking metaphors to keep interesting information flowing back and forth between branding people and the consuming public.”

Most elevator pitches look like this: long, boring, senseless, and ineffective. You probably stopped reading after the first sentence. Or the pitch looked so long you didn’t read it at all.


Fortunately, Anthony came to same conclusion:

“That’s a little wordy, especially for a business card, so let’s try a little high-concept pitch development. Hmm… relations that people will understand. “A for B”, where A is a known brand in my space, and B is the target audience… how about:

Facebook for Brands

“I think I like it! Not least of which is the rumor floating around today that Facebook is about to be acquired by Microsoft for something like 15 to 20 billion dollars.”

I like it too. Anthony started with a long paragraph that actually hurt him more than it helped. Then he turned it into a high concept pitch that opens the door to a conversation about his company.