February 4, 2016

Major Blunders to Avoid When Pitching to Influencers (Especially at SXSW)


Having been to SXSW numerous times before, I was delighted to have had the opportunity to attend again last year — this time, with a company of my own. Having my own venture to promote made me feel both excited and strangely vulnerable. Amid all the meetings, on-camera interviews, and speaking engagement, I found myself keenly aware of certain individuals I should talk to and connect with — folks who could have been very powerful catalysts for my company.

I’d never before thought twice about how I approached people I wanted or needed to meet. So I decided — since I have the good fortune of knowing awesome and experienced tech figures — to ask for feedback on what not to do when pitching your company, thought, or idea. In the process, I gleaned some very useful and surprising insights that I hope will help other young entrepreneurs as they navigate upcoming tech conferences.

1. Don’t Throw Yourself at Strangers

I come from the entertainment world, where I was an actress, and not everyone receives me and my newfound coder-techiness with the warmth I desire. Indeed, to some, it is a baffling combo — the actress-turned-tech-girl thing — even though I now run a software company, Klickly, which I architected, and have all but left the big screen behind me.

During the conference, one of my well-respected friends went around SXSW introducing me as the “Queen of Silicon Beach,” which — while it rang vaguely reminiscent of silicone beach (L.A. has one of those, too!) — at least provided a pre-vetted stamp of approval – and that usually makes people want to know more.

The takeaway: Ask a mentor in the space to introduce you to someone you need to know. If you can’t find anyone to vouch for you, consider what else you might be doing wrong.

2. Don’t Start a Filibuster

I ran into a former L.A. tech guru, Sean Percival of 500 Startups, at a classy, late-night tech function on a rooftop in downtown Austin. I asked for his sage advice, and his response was, “It’s important to understand some investors get a lot of pitches at events. So the best thing you can do is respect their time and keep your pitch brief.”

Like the concept of having only 30 seconds to talk with the proverbial VC in the “elevator pitch scenario,” this is a good rule of thumb. In fact, given the height of the building we were on, and the length of the elevator ride, I figured Sean may have even encountered this scenario en route to the party.

JumpThe takeaway: Get to the point quickly and ask if you can follow up via email with more information and your investor presentation.

3. Don’t Pitch During a Rave

Lo Toney, partner at Comcast Ventures, had what might seem like obvious advice, but not everyone follows it. The end of the night — just when investors may think they’re safe to enjoy a great party, music, and dancing — is one of the worst times to be approached for a pitch. Not only are investors not in a work-related frame of mind at this point, but it’s just logistically hard to hear.

Lo told me, “The worst pitch that I got was when an entrepreneur wanted to pitch me during a party. It was after 10 p.m., he’d clearly had a few adult beverages, and he insisted on pitching me even with the music blasting.”

The takeaway: Telling VIPs info they might not want to hear, in a place they physically can’t hear you, is just bad business.

4. Don’t Cyberstalk

This tip was shared by serial entrepreneur Matt Galligan. As we strolled down Rainey St. in Austin, he uttered this gem: “Just because someone [you want to meet] tweets their breakfast tacos, Instagrams their drink, or checks in on Swarm, their check-ins do not mean it’s an invitation to find – okay, stalk – them.” This took me by surprise. Did fellow founders actively stalk VIPs by tracking them on social media? Apparently, yes.

The takeaway: Matt says instead of stalking VIPs with whom you want to meet, “consider posting a comment [in their feed] or sending a reply to see if it’s cool if you drop in and say hi.”

5. Don’t Probe for Info

The wonderful tech founder Ann Greenberg enlightened me on a pet peeve of hers. I’ll admit, it made me quake in my boots because I think I’ve done this. To her.

“An immediate turnoff for me is when a founder asks to ‘pick my brain,'” Anne said. “It says to me that you don’t respect my time, and worse, that your ideas aren’t yet gelled or original. Not a great way to pitch!”

The takeaway: Instead of asking a founder or investor to “pick their brain” and come up with ideas for you, develop a concise set of “asks” or “questions” you can intelligently ply.

6. Bonus: Don’t Wear an Elf Costume

ElfMy friend McKenna Walsh, partner emeritus of DreamVentures, likens getting an investment to getting married: “You’re trying to find a potential partner. Anything that you wouldn’t do on a first date, don’t do it when pitching a VC.”

Apparently, this lesson became especially pertinent when a startup CEO, who was fundraising, decided he simply had to pitch her. At 3 a.m. Dressed as an elf. It wasn’t the suspenders, thigh-highs, or speedo that were the deal breaker, though. It was his state of inebriation. Needless to say, if it were a first date, this elf’s charms would not be getting him a second.

The takeaway: Play the long game and avoid drinking too much. Chances are, in a quick meeting you cannot convince anyone to fund you, but you can certainly convince them to not fund you.

These tips seem pretty basic, but based on my conversations at SXSW, they need to be learned. Form a real relationship, an authentic connection. Be respectful and polite. And remember: you are approaching a stranger and asking them for money or advice. Get the follow-up meeting and move on.


A version of this article originally appeared on BusinessCollective.

Cooper Harris is the CEO and founder of Klickly, a pro-social donations software platform based in Santa Monica. 

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