Starting Up (Is Hard To Do): Lessons Learned From My First Pitch

My partner and I formally pitched our startup for the very first time last week. We had a mix of apprehension, excitement and nerves. While there are others with more experience to talk about the nuts and bolts of a perfect pitch, I wanted to write about my experience; both the good and the bad.

Pitch The Problem

Dave McClure of 500 Startups wrote an interesting blog several years ago that changed my approach to pitching. In his post he said, “Your solution is not my problem.” If your audience isn’t intimately familiar or connected to the problem, how could they possibly know the value of your solution?

You have to remember that you are pitching to a diverse audience coming from different backgrounds, cultures and socio economic situations, and they might not have directly experienced or considered the problem you are solving. You must first sell that problem; once done, your solution will be that much more valuable.

Have Every Possible Video Adapter On Hand

VGA, HDMI, Mac, PC or coaxial cable — if you have a plug that can connect your monitor to a projector, you better have it on hand. If possible, scout out the presentation room beforehand and make sure you can connect your computer. The next best option is to ask the coordinator of the event to tell you what video hookups are on hand. Regardless, you never know what adapter will walk away in the middle of the night, so you should still come prepared.

When we arrived to the pitch, we had difficulties wiring up the computer to the projector. Nothing worked, and I got very nervous. My partner’s computer bag was chock-full with every video connection possible, so I was able to take a sigh of relief knowing that we would eventually get the display up and running. The next presenter wasn’t so lucky and had to copy all his files to a loaner laptop to display his presentation.

10-Minute Pitch? Have A Five-Minute Pitch In Your Back Pocket

Prior to event, you will probably know how long you will have to pitch. You will have late nights, crafting a pitch that maximizes every second of your allotted time. On the day of the pitch, you show up only to be told that you have half the time to do your pitch. Whether you misread the information, or a panel member has to leave early, you better be ready to pitch your idea with less time.

This happened to us, and we were caught completely by surprise. Upon hearing we had eight minutes to pitch instead of 12 minutes, we looked at each other with panic in our eyes.  On the spot, we had to cut, or speed up, most of our pitch without the benefit of getting to talk to one another. This was among the most stressful eight minutes I have ever been through.

That moment taught me the value of having different length pitches in your pocket. Moving forward, I will not only prepare for the length of time that I think I have, but will also walk through what will happen if I only have half the available time.

How Do You Get To Carnegie Hall?

Practice. Practice. Practice. Whether you are pitching for a local contest, or in front of a premier venture capitalist firm, you must practice your pitch extensively. When it is your turn to be in front of an audience, the last thing you want going through your mind before speaking is, “Man, I should have practiced this more!”

My startup offices out of Geekdom, the same place that houses the TechStars Cloud teams. I was talking with one of the guys there, and he told me about the rigorous TechStars pitch practice sessions. Almost every day he is pitching his business to different mentors, getting feedback and making tweaks. While this amount of practice might seem excessive, you will want to become familiar with your pitch inside and out.

Even if you aren’t looking for funding, or have an audience with a VC, you should work on your pitch. There is something magical that happens when you speak out loud what you have been only thinking in your head. Creating a pitch makes you clarify the problem you are solving, your key differentiators and even long-term strategies to make money. This is the true power of the pitch: it gives you a better insight into your own idea.

Starting Up (Is Hard to Do) is a weekly series published every Friday on the Rackspace Blog from a guy who is in the trenches of starting up a business while working a day job. Check out Garrett’s previous post that talked about getting marketing material on the cheap.

Garrett Heath develops content and supports customers on the Rackspace Social Media team. His previous experience includes technical project management in the cloud, content marketing and social media marketing. He enjoys writing about how the cloud is spurring innovation and telling stories about the people behind the tech. You can also read his work at In his free time, Garrett writes about food and local San Antonio culture at SA Flavor.


  1. My personal preference is to *create* the solution, build a customer base, *then* start doing my pitching. Too much vaporware out there. Everyone has ideas. It’s who JUST DOES IT, with whatever limited resources they have, that will win the day.

    • Jeremy – I agree with you, and in fact a successful entrepreneur, investor and mentor told me that VCs would rather see a demo than a slidedeck. I have actually a working piece of software that I am currently selling/pitching to clients. However, I think that when you are pitching your product it is far more compelling to let people know what the problem is (and the how big of a problem it is) so that you can then come in and show how effective your idea/software/service is at solving it. The pitch I am talking about is not pitching simply an idea/vaporware, but rather a tangible, working solution. Thank you for your comment!


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