How Pitching Is Like A First Date

sales pitchPitching your startup is like going on a first date. Entrepreneurs should be confident without being cocky, approachable without seeming desperate, and passionate without being over the top. The goal is to build up enough intrigue to be asked on a second date (or a follow-up meeting) without scaring the listener off. But that’s no easy task.

Here are four common pitching turnoffs that are easy to make — and advice for avoiding each:

PUSHING RATHER THAN PULLING

Picture going on a first date with someone who immediately rattles off the reasons why you should marry them. Not only would it eliminate the thrill of the chase, but you’d wonder what’s wrong beneath the hood. However, if the same person were to casually mention the homemade meal he or she cooked for some old Harvard buddies the other night, they would earn some serious points in the ‘potential mate’ department. It’s a matter of creating intrigue rather than trying to force interest.

The same goes for a company pitch. If the audience feels that they’re being force-fed a value proposition that they can’t relate to, their walls will go up. However, by piquing the their curiosity in a less forward way — such as describing the excitement you felt in saving thousands of dollars for one of your client companies — the audience would be left wanting more. Present genuine accomplishments in a modest, matter-of-fact way, allowing the listeners to discover the value propositions that are most applicable to their own lives. They’ll appreciate your product a lot more if it is their idea to latch onto it.

USING BUZZWORDS AND INDUSTRY JARGON

Buzzwords are like corny pick-up lines — they make the listener question the authenticity, credibility, and even sanity of the person pitching. Sure, you may have a ‘rockstar team’ that is going to ‘massively disrupt’ an industry with ‘game-changing technology,’ but using these clichéd words make you sound naïve. The listener immediately places you in a bucket with the 50 other ‘rockstar’ entrepreneurs that they’ve heard make the same ‘disruptive’ claims.

Keep the pitch genuine and crisp, using proof points, metrics, and anecdotes that the audience can grasp in a meaningful way. Similarly, steer clear of using too much industry jargon. Understanding a pitch shouldn’t require a dictionary or a biomedical degree. Speak in layman’s terms so that the audience is actually listening to the description and not trying to figure out what was just said.

PITCHING AROUND A POWERPOINT

Trust in a relationship is crucial, so another dating red flag is a person who sounds too scripted (ex: “I didn’t know beauty until I saw you.”). Similarly, relying on a PowerPoint too heavily can make the entrepreneur sound canned and insincere. The audience should feel like your pitch is unique and heartfelt, not like you’ve fed these lines to thousands of other listeners.

Though it’s tempting to build a PowerPoint at the same time as a pitch, trying to force the pitch to be visual right away compromises the story arc. Instead, start offline with 20 notecards. Use the first 10 to answer the basic questions: problem, solution, market opportunity/size, team, unique IP/technology, competition, distribution strategy, business model, financials, funding status, etc.

Fill the remaining 10 notecards with good company bragging points (aka “power cards”). Examples would be impressive metrics (4 out of 5 users tell a friend about the product), high-quality partnerships (three Fortune 500 companies agreed to beta test the platform), or powerful quotes from customers (“ABC company increased our ROI by 5X”). Then arrange, combine, and re-arrange these 20 notecards until they fit into a story arc that flows, using relevant ‘power cards’ during transitions. Memorize the key facts, but keep in mind that no one wants to date someone who is following a script word-for-word.

CRAFTING THE PITCH ALONE

It’s not a bad idea to get a second opinion on your outfit before a date. Likewise, a little guidance, encouragement and even tough love from your friends can be crucial for polishing your message. The perfect pitch isn’t created in a vacuum.

Since entrepreneurs are self-starters by nature, few accept the fact that they can’t create a pitch alone. In reality, however, you’re often too close to your own company to know how to pitch it.

During my three months in the TechStars accelerator, each company was challenged to pitch every Wednesday night to a room of 35-50 peers. When the buzzer rang (three to five minutes later), the person pitching would have to be completely silent and accept criticism with a smile. No excuses. The trick was to truly listen, say “thank you,” and accept whatever challenge was given for the following week. If someone suggested that you pitch without slides the following week, or to use a fake character as an example, you’d do it for your own benefit.

But you don’t need to join an accelerator to get peer feedback. Start a weekly Meetup group with other entrepreneurs in the area. Not only will this be good practice for investor meetings, but the variations will prevent the pitch from becoming too scripted.

At the end of the day, you make the final decision about what feels right for your pitch, but the process gives you needed perspective, confidence and practice. Just like dating, at the end of the day, your demeanor is more important than the words you use.

Heidi Allstop is the founder of Spill, a confidential site for young adults to “spill” about hardships and share life advice with one another. She launched the company as a psychology student at University of Wisconsin-Madison and spread it to 150 college campuses in 15 countries. A TechStars alum and the winner of the Global Social Venture Competition, Allstop is on a mission to bring empathy online.  

The Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world’s most promising young entrepreneurs. In partnership with Citi, the YEC recently launched #StartupLab, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses via live video chats, an expert content library and email lessons. 

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