Pitchcrawl- Success, Failure, and Iteration

The Art of Investor Dating and Fail Points

Looking for investors is very similar to dating.  You run around in circles in hopes of finding the “one”.

Just like dating, it’s in your best interest to use your personal network to be introduced to the right people.  But, if you want to get more proactive about it, events are the way to go.

That’s why an event like Pitchcrawl is an awesome idea.  Just like a dating event, everyone is there for the same reason, meaning you have a higher chance of meeting “the one”.  And it’s less douchey than picking random people up at random times.

Events like Pitchcrawl have been inspired from Dave McClure’s Startup2Startup.  My desire for hosting Pitchcrawl came from that and a week of wasted time.

My week of wasted time: I decided I wanted to jumpstart my network and see what would come of going to events to find investor relationships.  Guess what?  There is a lack of investor/founder specific events.

I attended 4 “startup” events in 1 week, paid about $200 total for admissions, and met 3 investors.

Lame!  Cost of investor acquisition way too high and I don’t have enough time to wonder aimlessly.  I have a business to run.

If this was frustrating to me, I know it was frustrating my lot of founder friends.

So came the birth of Pitchcrawl.


Our startup Dishcrawl loves bringing people together over food, so creating experience for our extended startup family was natural.

The 3 Objectives of Pitchcrawl #1.

Objective 1. Event with only founders and investors present.  No random people.

We marketed Pitchcrawl as a founder/investor only event.

Objective 2. Encourage mingling and ensure founders are able to talk to as many investors as possible. (I always enourage fairness).

We came up with a 3 minute timer on pitching rounds so each entrepreneur could meet at least 4-5 investors.

Since we did the Pitchcrawl in the form of a Dishcrawl, we spend 45 minute at each venue, then walked to another location.  The very nature of this breaks up the flow and create new dynamics, which leads to more interesting relationships.

Objective 3. Add some stickiness to the event.

Food is the foundation of any strong relationship.  We made sure each stop had some noms to enjoy.

Successes and Failures of Pitchcrawl #1.

The energy was strong, vibrant, and very alpha that night.

95% of the folks attended were investors or founders.  There were a couple randoms that creeped in, but the ratio was satisfactory.


3 minute timers failed- massively.  By the 2nd stop, we said screw it and individually announced so investors could get the opportunity to talk to another startup if necessary.


People would eat easy handheld things, but eating anything involved was of no interest.

I was pleased to hear that most startups there were able to talk to everyone they wanted.  If we had just accomplished that that night, I was happy.


The energy of Downtown San Jose’s vibrant startup scene was captured that night.  Bright individuals connecting with each other in hopes of sparking the next technology revolution.

The vibrance of the night was captured by Content Magazine, San Jose Business Journal, San Jose Mercury News, San Jose Metblogs, and CJ Brasiel.

Pitchcrawl Iterations and the Birth of Pitchcrawl V2

We have decided to nix the 3 minute timers next time.  I’m a fan of fairness, but as a founder you better know how to hustle and make things happen yourself.

We’ll still do the Pitchcrawl in traditional Dishcrawl format (originally created to prevent having to sit next to the same person for the duration of a dinner) to make sure we keep the vibe dynamic, but the rest is up to you.

Focus- Pitchcrawl SF on Jan 10 will be focused around consumer software products, greentech and the like need not apply.

Passed appetizers and water for the food.  Less involved so you can focus on those awesome relationships.

Smaller groups- 40/50 people a time versus the mass of 85 people.

Screen the founders to ensure they are not randoms.

Make the vibe chiller and more fluid.  No structure.

Upping the genuinity- the goal of Pitchcrawl V2 is not to give 3 minute pitches, but be able to meet and build relationships with a variety of investors and founders.

Pitchcrawl SF January 10th

Join us for a Pitchcrawl through some startup hubs in SoMa on Jan 10th!

Founders, get your serendipity juices flowing.

Investors, come to mentor and give feedback to a burgeoning founder community.

Tickets can be purchased at and questions can be emailed to hi (at) dishcrawl (dot) com.

See you soon,

Tracy @ladyleet

  • suki

    Very interesting! :) Love that you found a need and filled it yourself, testing out what worked and what didn't. 

    Happy New Year's! Hope to see more of you in 2012.