When you want a puppy, start asking for a pony.

As one of the worst public speakers in the history of the world, I give mad props to anyone who can get on stage and talk to a random group of people.. let alone a room full of investors deciding whether or not they should give you their money. Every month, Chicago’s coolest developers, investors, and students pile into Rockit Bar where five, about-ready-to-launch entrepreneurs get 2 minutes to pitch their startups.

The only investor I’ve ever pitched to is Rick. I asked for advice; not $50K. So I admit I am no expert, I’ve heard my fair share of pitches and have been successfully persuading people for twenty one years. I think this is how you get people to do what you want (and end up making them like it, too)

1.  Be nice. 

2. Hypothetically speaking of course, if you’re doing a demonstration on how to make a smoothie, be prepared for your blender to freak out and splatter bananas all over your face. This way, when the class laughs at you, you’ll have a back up plan. Be prepared for everything to go horribly wrong, and always have something to fall back on.  If your wifi fails or your video loses sound, make sure you’ll be able to quickly recover. Sometimes a well-played catastrophe makes you stand out. Even just one well-rehearsed, crowd pleasing, one-liner, saved only for technical difficulties has the power to turn the mood around. Whatever it is, don’t just stand there with bananas on your face.

3. Talk to people who are interested in what you’re doing and becoming a part of it. Do research prior to talking to investors and find people who think your idea is great. Once you’ve got them window shopping: Be appealing. You’ll get life-long customers if the display is a good as what’s inside.

4. Once you’ve got someone’s attention, butter them up. I feel like sucking up has gotten a bad rep over the years, but, personally, I see no problem with it. If you’re an awesome person and are confident your idea is going to be mutually beneficial to all involved, what’s wrong with showing a little extra love? Prove you’re invested in them; they’ll invest in you. Convincing people takes hard work and creativity; no one is going to give you something if they feel it was effortless on your behalf.

5. When I was 7, my Uncle Hugh gave me a piece of advice: “When you want a puppy, start asking for a pony.” For a 7 year old girl, this meant: ask Dad to the point of being annoying; and if all else fails, ask Uncle Hugh. While asking is the first step in receiving, I’ve since learned that proving you’re deserving of something is much more effective. This isn’t to say that you should be asking for unrealistic things, but shows that success is driven by determination and persistence. You’ve got to know when to push forward and when to pull back. Be patient, getting what you want doesn’t happen right away and your 2 minute pitch is just the start. Eventually, you may even be able to work your way up to a point where even a pony is realistic.

(p.s. I never got a pony, I got a Vespa.)