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For the past 10 days I’ve sat through 200 company demos for the
TechCrunch50 conference. These demos are mostly done over the phone
for 10 minutes using the phone and web conferencing software like
WebEx or Adobe’s wonderful new “Connect” service.

After doing 2,500 minutes of demos (40 hours) this year and many more
last year for the conference, I’ve learned a lot about what makes for
a great demo and what makes for a horrible demo. Since demoing your
idea is a key to your success as an entrepreneur, I thought I would
share everything I know in a few simple bullet points.

These tips are applicable to presenting in front of an investor, a
partner as well as a demo style conference. Of course, every situation
is different so consider these loose guidelines.

Background: The TechCrunch50 conference is taking places on September
8-10th in San Francisco and you can find more information here:
www.techcrunch50.com. Mike Arrington of TechCrunch.com and I started
the event last year as a place where fifty startup companies could
launch their products without having to pay a fee (i.e. the incumbent
conference called DEMO charges $18,500 to launch a startup
company–that’s really low/absusive in my book). Google, Microsoft,
Yahoo, Sequoia Capital and a bunch of other fine partners have joined
us in hosting the event.

1. Show your product within the first 60 seconds
——————————————-
Most folks start their presentations with information like the size of
the market they are tackling (tens of billions, we only need 1%!),
their inflated corporate bios, the philosophical approach they’re
taking, and boring Powerpoint graphics explaining some convoluted
workflow of their product.

The longer it takes for you to show your product, the worse your
product is. Folks who have a kick-ass product don’t spend five or ten
minutes “setting the stage” or “giving the background.” Folks with
killer products CAN’T WAIT to show you their product. Their demos
start with their homepage and quickly jump into the users experience.
If a picture tells a thousand stories, then a product demo tells a
million.

Show your product immediately, and if you don’t have a product to show
don’t take the meeting.

2. The best products take less than five minutes to demo
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The greatest tech products over the past 10 years would take no more
than five minutes each to demo. For example:

a) Larry and Sergey could demo Google search in less than five
minutes. Here’s a box, type something in and you get a huge reward.

b) Steve Jobs could demo the iPod in less than five minutes. Plug it
in, put in your CDs and it syncs your music. Turn it on and use the
wheel to select what songs you want to listen to.

c) Chris DeWolfe could demo MySpace in less than five minutes. Sign
up, fill out your profile, and add your friends. For bonus points add
some widgets to your page.

I think you get the idea: the better the product the LESS time it
takes to demo. If your product demo takes more than five minutes to
demo, it probably sucks. All the tiny little features that matter to
you are of course important–God is in the details–however, when
presenting your company, you don’t have to show them. Larry and Sergey
wouldn’t open up the advanced search tab and the list of operators you
can use in Google during a demo.

Steve Jobs does take the demo details to a fairly detailed level, but
you and I are not Steve Jobs. There is only one Steve Jobs and there
is only one Apple. You’re never going to build something as cool as
Steve, and as such there is no need for you to talk about your product
for five or ten minutes.

3. Leave people wanting more.
——————————————-
If you take my advice in point two, then folks should be either blown
away or intrigued by your core product. If they are not somewhere in
that spectrum, you need to rebuild your core product.

When I pitched Mahalo to investors, I had five sheets of paper with
different search results on each. I put them on a table and said which
one is the best. Obviously I knew my result was the best, and that
simple demonstration lead to MASSIVE discussion: how was the page
built? how long did it take to build? what would it cost to make that
page? how often do you need to update it? how can you scale that
business? how many pages can you create before it breaks even?

It’s best for folks to discover the merits of your product for
themselves, and it’s up to you to make such a compelling core product
that they are intrigued enough to explore it.

4. Talk about what you’ve done, not what you’re going to do.
——————————————-
Weak startups and their leaders seem to immediately start talk about
“what’s next,” as opposed to focusing on the core product. Anyone can
say we’re going to add: a mobile version, collaborative filtering, an
advertising network, visualizations, a marketplace, a browser plugin,
a browser and a social network to their product. In fact, given the
amount of open source and off the shelf software out there, combined
with the large number of developers in the world, anyone can bolt
these things on to their service in a week or three.

Who cares what you’re going to bolt on to your startup? What really
matters is the core functionality of your startup.

Steve Jobs has become at once the world’s greatest salesman and
product developer because he only announces Apple’s achievements. He
doesn’t waste time on what Apple’s going to do: he talks about the
here and now. Microsoft’s old strategy was to talk about products that
were coming and that put them in the horrible position of having to
backpedal when they changed their mind about a product.

5. Understand your competitive landscape–current and historical.
——————————————-
This year I’ve had three companies show me group SMS messaging
products, and most of them did not know what UPOC.com was (Gordon
Gould’s group SMS messaging service that was five years ahead of its
time). I’ve had three or four companies over the past two years of
TechCrunch50 conferences pitch me on Third Voice–the controversial
“web annotation” service from Web 1.0. [ Side note: I loved the
concept of Third Voice so much I considered starting a company like it
and even bought the domain name annotated.com. ]

When I pitched the idea for Weblogs, Inc. to Mark Cuban, Yossi Vardi
and Jeff Bezos, I understood all the niche email marketing and
newsletter companies from the early and mid-nineties cold. I
researched why they worked and why they failed, and I knew which ones
were sold and bought and by whom. When I pitched Mahalo to Sequoia
Capital, I knew the history of human-powered search and directories
from DMOZ to Yahoo Directory to LookSmart.

If you don’t know the competitive landscape, and the shoulder’s you’re
standing on, folks are not going to be comfortable giving you their
money, time or attention.

6. Short answers are best.
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When taking questions about your product answer questions shortly.
This is a very challenging thing for many people–including myself–to
do. If you’re like me, you’ve probably thought out your startup’s
issues a thousand different ways. When I sit at the poker table I play
a game where I think out every possible scenario for not only my
hands, but the hands of my opponents (this is fairly standard among
advanced poker players from what I understand).

Say I have Ace King and I raised out of position and the button called
my raise pre-flop. Then they re-raised me on the flop, which had an
Ace. What does that tell me? They could have an ace, they could have
two aces and have slow played me, they could have a medium pocket pair
and they want to see if I have an ace, maybe they are on a flush or
straight draw or maybe they suck at poker. Who the hell knows?!?! You
can go insane trying to figure all these things out–that’s why poker
becomes very addictive.

The point is all that inner thinking is chaos when you try to explain
it to another person. It’s pure madness after 60 seconds of talking.
The best thing to do is answer the question with the most concise
answer. For example, when asked “what happens if Google enters your
market?” answer quickly and with confidence:

a) Google has entered many markets, but they are only #1 in search and
search advertising. They trail in social networking to MySpace and
Facebook, in classifieds to Craigslist, in news to Yahoo and AOL, in
email to Microsoft, AOL, and Yahoo, and in instant messaging to
Microsoft, AOL, and Yahoo.

b) We’re not sure if Google will enter our market, but hopefully we’ll
have developed our product enough that it will be a real sustainable
business by that time.

c) We think Google might enter our market at some point, and if they
do they and their competitors will certainly consider buying
us–creating a bidding war for our entrenched position.

d) Google is a very big company right now with a very big cash machine
that they have to focus on and protect–they will never do our
business with our level of focus. We will out execute them on all
fronts.

These are all amazing answers (I did, after all, come up with them),
and you can say them in around a minute. However, if you cram all four
of these sentences together you’ve spoken for five minutes.

7. PowerPoint bullet slides are death
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Do not make slide after slide explaining your business in bullet
points, because it’s really, really boring. Powerpoint/Keynote slides
that are not boring include charts, product shots, feature set tables
and the like. Things that explain big concepts with ease and grace are
great, but bullet points of obvious facts show that:

a) you don’t have the ability to create a compelling story with data
b) you don’t think that much of the person being presented the information

I’m not a huge fan of “funny slides” or lots of graphics for graphics
sake. You’re not pitching your company to get laughs–unless you’re on
stage–you’re doing it to raise capital, close a partnership or get on
stage at a conference. Keep it focused and to the point.

8. How to use this new device called the phone.
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When presenting over the phone use a handset and a land-line… only!

It’s amazing to me that any person doing a business call would conduct
it on their mobile phone. Mobile phones sound horrible 95% of the
time, and they frequently cut out. If you are presenting your company
take it seriously and get yourself to a landline. You have limited
time and don’t want folks to miss a single word.

Speakerphones are horrible, and putting the person receiving the demo
on speaker phone during a demo is just disrespectful. You can hear all
the rustling, side conversations and horrible echos when you’re on
speaker phone. When doing a demo pick up the handset and speak. If you
go to a Q&A session then use speaker phone. That’s why it exists.

Only use a headset if it is very, very high-fidelity and you have the
microphone right up to your mouth. Also, don’t eat, drink or breath
heavy into the microphone or you run the risk of sounding like an
animal. I use an amazing Plantronics headset, and I like me some Green
Matcha tea, but I hit the mute key when I sip!

I know it sounds crazy to have a discussion about how to use the
phone, but the majority of these young people actually think it’s
acceptable to have two or three drop offs in a call–it’s not. Grow up
and get a land line.

9. How to handle questions you don’t know the answer to
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After you do your concise presentation you’re hopefully going to get a
lot of questions. Here are some important tips to consider when you
don’t know the answer cold:

a) take a moment to think about the question. You can even say
“Hmmm… that’s a good question. Let me think about that for a
second.” Folks appreciate a little consideration when someone takes a
question.

b) if you don’t have an answer be honest and say you don’t. There are
many ways to say this including: “I’m not really sure, I’m going to
have to think about that for a bit and get back to you,” or “I’m not
sure to be honest. What do you think?”

c) feel free to think out loud and brainstorm with the person. You can
do this by saying “I’ve never really considered that. Perhaps you can
expand the question a little and we can explore it right now.”

d) if you’re not sure of the answer you can always say you’ll cross
that bridge when you come to it. “I’m not sure how we would deal with
a sudden spike in the cost of bandwidth, we would have to collect more
information and answer that question down the road. It is a manageable
risk factor I suppose. ”

The worst thing to do when you don’t have an answer is b.s. the
person. No one has an answer for everything, except a b.s. artists.
So, feel free to say you don’t know–folks find it refreshingly humble
and honest.

10. Always confirm the time of your meeting/call, and always be 15
minutes early.
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People are really busy and meetings get mixed up. Every meeting or
phone call I do is confirmed twice: once by email, and once on the day
before the meeting. Reconfirming meetings makes you look like a true
player and it costs you nothing. You do this by sending a simple email
saying “Looking forward to seeing you tomorrow at your offices at 123
Main Street at 3pm. If anything changes you can reach me on my mobile
at 310-555-1212.”

Also, be early. Come on. If you’re doing a meeting with someone who
might invest in your company, do a business deal with you, etc., you
can show a lot of respect by being in their lobby or on hold on the
conference call five to 15 minutes ahead of time. Don’t show up more
than 15 minutes ahead of time or you’ll look like a stalker. If you
get to your meeting 45 minutes ahead of time go to the Starbucks and
buy yourself a treat for being so on top of things.

What are your best tips for giving a proper demo of your company on
the phone or in person?

In your mind, what are the worst things folks have done during a presentation?