Startup Pitching Tips and Tricks

Over the years I’ve spent a lot of time working with startups and entrepreneurs on the exciting and often daunting act of “pitching”. The pitch is at the heart of the start when it comes to getting your ass moving. Its the basis of hustle. You gotta move, you gotta connect, impress, engage, relate, convey, […]

Published on August 12, 2015 by Dan Rockwell

Over the years I’ve spent a lot of time working with startups and entrepreneurs on the exciting and often daunting act of “pitching”. The pitch is at the heart of the start when it comes to getting your ass moving. Its the basis of hustle. You gotta move, you gotta connect, impress, engage, relate, convey, and attract.

When I think about this dance of pitching there’s lots of things to consider. This morning, coming off yesterday’s Futurey Healthcare Startup Meetup in Columbus, and looking at my agenda for the day, I’m at the cancer center on campus waaaay early to talk what, startups, thats right, I’m juggling thoughts in my head around pitching.

Some things that I think are important to the art of pitching, tips and tricks, and likely thoughts in my head for this morning.

Awareness, you have to be aware of where to pitch, who to pitch, why you’re pitching. Awareness is really really important. Without it, you lose potential connects because you’re not adding up the pattern before you. Awareness and audacity kinda go together as well.

Audacity, one of my favorite words in the startup space and I’m likely to be only guy that thinks about it. Some call it confidence, others call it gusto, drive etc. To me its audacity, you have the gall to present, to change, to create with vigor!

Reach, you must reach into the orgs and centers and conference rooms you want to get into. Reach can be really hard at times but its 99% psychological, meaning its just you. Get over your inability to look like an idiot, what matters more pride or getting in the room and talking.

Resonate, this is the most important thing in starting up. Meaning. You need to resonate. Your pitch needs to connect, convey, and create that meaningful jelly of awesome between you and your would be pitch listeners. When a pitch fails its largely because of the lack of resonating, you didn’t quite connect.

Audience, often not an element we consider when pitching, I mean people are there, they must hear the pitch so be it. However understanding audience dynamics, understanding who that audience is, picking out the judge, the hero, the helper, the sway man, the heckler – all very important, especially if your mark, your target is in the middle of them. You always have a target in mind, you could think its “everyone”, but often its “you”, you pitch for yourself to strengthen yourself and thats powerful. For the longest time I’ve kinda pitched to myself, to resonate within and then oh yeah, people are here. I had to build confidence to talk to folks, it was a draw to do, it came naturally over time but I didn’t get real confidence at doing it unless I did it more and more and then studying people- that was really fun. Audience is key. Now I think when I hear pitches, who’s the target in the audience, the VC, the customers, the designer looking for a gig, a developer looking for a startup to join. There’s always a target. Plus the minute you let your pitch go, you have to control the audience, one heckler can take down an idea faster than your failing business model.

Connection, after you pitch, connect, meet and talk to the people you pitched to. Admittedly I suck at this. People may think I’m super connected and it appears that way at times but I often feel like an actor on the stage, the minute i’m done, I’m like ready to get out of that skin and go back to working at the coffee bar. There’s a part of me that wants to be forgotten, renewed, fresh. But if you’re looking to maximize the resonance of your pitch, you better be connecting. Connecting is what gets you another meeting, another opportunity to pitch, and helps connect you to the person you should be talking to next.

Commitment, you have to be doing this do be doing this. People often ask me how do I keep doing this- startups, pitching, working at the university, running Big Kitty Labs, etc? How? How??! I’m committed to the cause, and I insanely enjoy it and its not really work for me. But successful pitching is signing up for the endurance train, you gotta be there to get there and there’s no real way to skip over that. Effort is part of the game. Effort is the reason why you’re in the game. Effort is what you’re banking on. Return only nets from effort.

Now i’m sure I left some sauce on the table, there’s always more.  Things like, what’s in the pitch, how you deliver the pitch, whats the goal of the pitch, and then what happens after ya pitch- umm hello get back to doing what you do and or getting another moment to pitch.

A sign of a great pitch tho to me is just talking, thats it.  When you talk you are having connection, no more marketing bullshit, no more wondering if your graphics bewildered them, no ya see when ya just talk to people they sort you out and thats likely the more critical aspect of the whole game, the pitch worked and now you’re talking.