Archives For November 30, 1999

TechCrunch 50 DemoPit FAQ

David Barrett —  August 20, 2009 — 2 Comments

Wow, quite a response on the “Expense Reports That Don’t Suck Is the TC50 DemoPit worth it?” blog post!  Here are some other questions I’ve received in followup emails; feel free to send more to

Do I really need a partner, or can I do it all myself?
Answer: Yes, one-man-shows are fine.  If you can arrange it, I do suggest bringing a partner to help demo.  But it’s not crucial.

Must I do a live demo, or can I show a video?
Answer: Definitely do not show a video.  People will assume your product doesn’t actually exist and will ignore you even more.  People go to conferences to see the real deal, live.  They can go to your website if they want to see a video.

Should I bring a big sign?
Answer: They’ll give you a sign with your company name.  Some people bring others, but I don’t think I’d recommend it.  The DemoPit is about startups.  Anybody who rolls in with fancy signs feels out of place — it seems a bit pretentious to have some big huge thing when you’re just one dude with a laptop bootstrapping a startup.  As an investor I’d really question your ability to spend wisely.  Same goes for fancy printouts and trinkets — people are overwhelmed with junk at conferences, I’m not convinced any of it really has lasting value, and I suspect all of it is more damaging than helpful.

After the conference, how do I actually go out and raise money?
Answer: In general, it works like this:

  1. Get a list of everybody you know who has money, or knows people who have money.  Ideally this list would be seeded with the contacts you meet at TC50.
  2. Pitch them all on the startup, focusing on three questions: “What do you think of the product?”, “How much would you be interested in investing?”, “Who else should I talk to? (Ask for an email introduction.)”
  3. Keep adding to your list until the sum of all the soft commitments exceeds the amount you want to raise by some healthy margin.
  4. Contact the person who is offering to put in the most money — this is the “lead investor”.  This is the person you’ll negotiate the terms with; everybody else will “follow” and just rubber-stamp those terms.
  5. Ask the lead which of the followers they want in.
  6. Ask those followers if they’re in for real.  Repeat 5-6 until you have a full set of investors.
  7. Finalize terms with the lead.
  8. Review terms with the followers.
  9. Ask everyone to sign.
  10. Get the money a bit later.
  11. Celebrate!  Then get back to work. 🙂

This one obviously has a lot more detail behind it; if you’re interested in more, please let me know.

David Barrett (, Twitter: @expensify

I’ve had a surprising number of people write me today asking if the TechCrunch 50 Demo Pit is worth it. I’m guessing this means they announced who did and didn’t make the cut to be on the big stage (don’t feel bad, we didn’t either!), and so there are a lot of people out there wondering if they should accept the consolation prize of demoing in the Demo Pit. Like anything, it is what you make of it, but if you go in with the right attitude and expectations, I’d have to say yes. It’s definitely worth it.

The Good

The DemoPit won’t make or break your company, it’ll just push you along whatever direction you’re already going.  If you’re doing good things, it’ll accelerate that.  If you’re not, it’ll reaffirm that.  Either way, you’ll get unbeatable, no-punches-pulled feedback from people who know what they’re talking about.  In Expensify’s case, we learned a hard lesson: yes our prepaid cards are cool, but the real excitement is around credit card import and expense reporting.  That’s a valuable lesson to learn, and worth every penny.

Similarly, everybody who’s anybody in the startup world is there, and that includes VCs. Expensify was in the lucky position of not needing to raise money when we were there, but we were still inundated by investors.  As such, when we actually did go out to raise a round, we already had a large set of initial contacts — a crucial starting point to what is essentially an iterative “who do you know” networking process.

The Bad

TechCrunch 50 doesn’t come with the promise of coverage, from TechCrunch or anyone else.  It’ll put you in contact with press and users, but it’s up to you to seal the deal.  (In our case, I chalk it up to the tireless efforts of one of our investors and advisors, Travis Kalanick.) Likewise, the real action is up on stage — the Demo Pit is very much a sideshow.  The best side show in town, but don’t go in with the expectation that you’re going to be center stage.

The Ugly

If you do decide to go to the demo pit, here are my top 10 suggestions for how to maximize the event:

1) Host locally. Conferences are notorious for having internet isssues, so don’t risk it: just host everything locally right off your demo computer.  It’ll go faster, it’ll be more reliable, and you’ll have so much less stress as a result.  Just be sure to edit your /etc/hosts file to map your domain (eg, to localhost ( so the domain looks right in the address bar!

2) Defend your turf. The table next to me had this huge standing sign that obscured the view of me. I asked them to move it behind their table, and they did.  Pretty much everyone there is cool and trying to make things happen; just be cool and ask those around you to return the favor.

3) Get a solid 3-5 minute pitch. We demoed about 100 times (we maintained a counter). Our pitch was good at the start, but it was absolutely rock solid at the end: there’s a very limited set of questions — by the end you learn them all and will have found the perfect answer to each. In fact, I’d say the #1 benefit to TC50 has nothing to do with press, investors, or anything. It’s the opportunity to practice your pitch in front of real people, again and again. This will pay off a thousandfold when you’re out raising money.

4) Work it. People will not come to you unprompted, you need to go get them. The second someone gets eye contact, make an introduction. Not with some clever cheeseball line, just with a “hi”. In my experience, the  typical pitch starts like this:

  • Me: I’m standing next to my 24″ diameter table with a laptop and a decent-size flatscreen monitor. People are milling about. I’m facing the traffic, smiling and attempting to make eye contact while patiently awaiting my next target.
  • Them: Someone is wandering around, glancing at the tables but making no real effort to approach any of them. They are probably there for some other startup and have no real interest in talking with you. But they might glance your way and see you standing there.
  • Me: Make eye contact, smile, and say “Hi!” Maybe “Enjoying the conference?” something disarming. Indicate you’re not a used-car salesman.
  • Them: They might take pity on you and walk over to where you are, because they’ve got time before the big stage starts again and nowhere else to be.
  • Them: “So, what do you do?”
  • Me: “We do expense reports… do you do expense reports?”
  • Them: (bored and sorta put off by the obvious question) “Um, yes.”
  • Me: “Do you love them?”
  • Them: “Heh, no I hate them.  (they give a story about why they hate them)”
  • Me: “Totally understand, everybody hates them. That’s why we do ‘expense reports that don’t suck.’ We do that by importing expenses and receipts from your credit card, submitting PDF expense reports through email, and reimbursing entirely online.” (wait for them to prompt you to continue)
  • Them: “Huh… what does that mean?”
  • Me: “Let me show you…”
  • Third person wanders by, mildly interested
  • Me: “One second… Hi there! Do you do expense reports?”
  • Third person: “Um, me? Yes, I do, why?”
  • Me: “We’re Expensify, and we do expense reports that don’t suck. I was just explaining how we import expenses and receipts straight from your credit card, submit PDF expense reports through email, and reimburse entirely online. Right now we’re creating an expense report…”
  • Finish the demo in record time. It’s got to be fast and visually compelling.
  • Me: “So, that’s the scoop: import receipts and expenses from your credit card, submit PDF expense reports through email, reimburse entirely online.” (keep repeating the key values)
  • Ask them about themselves, their business, their expense reporting habits, etc. Try to figure out if they’re a particularly good partner, customer, investor, news contact, etc.
  • They’ll have a series of very basic questions to which you’ll gradually figure out the perfect answers.
  • In the time you’ve given the demo, other people might have come by and are standing in the wings. You need to politely push away the first group so you can focus on the second. Accordingly, your partner should reset the demo immediately upon finishing so you’re ready for the next. Even better — when the crowd stacks up, have you and your partner each handle different groups.
  • Me, to first group: “Thanks, can I get a business card? Here’s mine. Incidentally, please keep us in mind for your chip! Oh, you don’t know what it’s for? Just put it in this bucket right here (hold it out) to vote for us as the demo pit audience pick; the startup with the most chips gets to present on the big stage at the end. (keep holding it out) Thanks, and please send your friends over! (To second group) Hi there! Are you enjoying the conference?”
  • Repeat 100 times.

5) Get a good business card that doesn’t look like a business card. The Expensify business card looks just like a credit card. So much so that every time I hand it out, people are taken aback. It creates a conversation every time. Write a quick summary of your business on the back so when they’re going through the stack of cards at the end, they have some way to remember what you do.

The best business card doesnt look like one.

6) Stay “on” at all times. When getting a coffee, position yourself in a vantage point next to the sugar and milk. People need to stop there to fix their coffee; chat them up. Hand out lots of business cards, tell them where your table is, and ask them to stop by. They probably won’t, but increases the odds they’ll recognize you and come over if they happen to walk past.

7) Skip the swag. Don’t bother with putting out fliers, nobody cares and the cleaning people throw them away minutes after they’re put down. I don’t see the value of giving out trinkets. They’re expensive and produce no lasting value.

8 ) 2 people at the booth, no more. More than that and you look both desperate and wasteful with your money. If you have others, have them circulate in the crowd and send people back to you.

9) Keep going to the very end. Toward the end of the day, just plant yourself at the big-stage exits and keep pitching for that almighty demopit chip. Many people  might have seen you and liked you but never gotten around to deciding. Furthermore, some really great conversations start with “Why should I give you my chip?”

10) Follow up when it’s over. When done with the conference you’ll have a huge stack of the cards and no idea what to do with them. I’d suggest sending them to Shoeboxed to have them all scanned (even better – buy yourself a NeatCo business card scanner), add them to your mailing list, and then send a “Nice meeting you at TC50, I’ve added you to our mailing list” email.

So there you have it, those are my tips for how to make your DemoPit launch a success.  Will it lead to instant riches?  Doubtful.  Will it create a stack of good contacts?  Probably.  Will it be a good time?  Definitely.

Drop me a line if you have any additional questions.  But you’ve got to launch somewhere and you can only do it once: given the option, I think the TC50 is the clear choice.  If you have the opportunity, I’d suggest you take it.  If you do, please write me and let me know how it goes!

David Barrett (, Twitter: @expensify

Update: Check out my TechCrunch 50 DemoPit FAQ for more questions and answers about The Pit.

Update 2: Travis is generously offering up his enormous couch for free to two scrappy TC 50 presenters for the duration of the event.  Act fast!

Update 3: The man himself Michael Arrington tells you how to make an introduction (just don’t ask to shake his hand).

from everybody who’s anybody in the startup world

Well, the word is out: Expensify is live and taking orders for our one-click expense report service. I’ll have more to say in a bit, but for the moment I’ll let Travis Kalanick (our advisor) do the talking:

“Expensify is launching at TC50!

Who here has a bag of stale receipts sitting in their closet? Receipts that long, long ago should have made it into some expense report… of course to get there, you would have had to organize that big bag of receipts in chronological order, affixed and taped each of them to a separate blank sheet of paper, gotten some excel sheet or web-form and done a few hours of data entry. You’d also have to remember what was discussed at that steak dinner in Denver (it was with customers…yeah, I’m sure it was) and then list their full names and titles. The list of headaches stretches for miles…Taxi receipts not filled out, separating room charges from room service and hotel Internet, old faded receipts that are illegible… the list goes on and on.

So I think we all would agree that there is one word that is synonymous with doing expense reports… PAIN.

So much pain that it takes up to 45 minutes per $1000 of expense reporting. For employees with expense-prone job descriptions (there are 50 million of you in the US: salespeople, office managers, small-business owners) that comes to 30-40 hours a year. That’s a week’s worth of vacation, or a week more of actual selling to hit your quota.

The pain for many of the less expense-disciplined among us, hits us in our pocket book. Some estimates are that 5% or more of all legitimate expenses never get reimbursed because of receipts that get lost, and expense reports that don’t get filed (referring to that bag of wilting receipts above).

Expensify wants to change that.

Expensify’s mission is to empower small-business employees, independent contractors and sole proprietors with easy tools for PAINLESS expense reporting.

Expensify accomplishes this with three main Expensify components:

1) Expensify expense card – a card that you use to make expense purchases. You top-up Expensify card with your existing credit card. The card makes expense categorization a breeze and allows Expensify to automatically fill out expense reports.

2) Receipt capture and upload – take pictures of your receipts and upload with either Expensify’s iPhone application or with simple email attachments from your phone or PDA.

3) Expensify Dashboard – Expensify automatically associates the receipt images with the expense card entries. You’re only a few clicks away from a completed expense report. Submit digital expense reports to your boss or client (via email) or print out and send physical expense report.

So now you’re saying, this is all way too easy. Expense reports done with only a few clicks, submitted before I even get back to the office from a trip. No more lost receipts or expense report hell??!! How much does Expensify cost?

Identical to PayPal pricing on an existing credit card, Expensify charges 3% of transactions made to the Expensify expense card.

How can you justify Expensify cost?? If Expensify saves even one receipt in thirty from getting lost in the shuffle, the extra reimbursements means Expensify pays for itself! We also know that time is money, and the time you save not dealing with expense reports should add to your overall quality of life

And remember, Expensify charges ARE reimbursable expenses!!

So how do I get started?

Step 1 – Register at
– Enter email address and password
– Verification email sent to you
– Sign up for Expensify expense card

Step 2 – Set up iPhone/PDA for receipt image capture
– iPhone users: Install iPhone application for quick uploading of your receipt images
– Other phones/pda’s: Email photos to

Step 3 – Impatiently wait for your Expensify expense card to be mailed to you
– Should be delivered in one week

You’ve now been EXPENSIFY’D!! Enjoy easy no-hassle expense reporting!

Thanks for checking us out. Give Expensify a shot, let us know what you think, and don’t hold back. .. feedback for the product, venting over previous expense report nightmares, just sound off. .. . and thanks for getting EXPENSIFY’D!!

Travis Kalanick
Expensify Advisor and happy customer”

A great quote from Travis: “David thought it was a good idea, but when I started digging into the data, I determined it was a *great* idea.” Thanks for the intro Travis, I’ll follow up in a bit once I have some free time — the next flood of TechCrunchers are on their way!