A Glimpse Into the Most Awkward, Cringeworthy Business Meeting Ever

A Glimpse Into the Most Awkward, Cringeworthy Business Meeting Ever

How not to pitch, market, or sell your startup

A Glimpse Into the Most Awkward, Cringeworthy Business Meeting Ever
Photo by Braydon Anderson on Unsplash

On the totem pole of criteria for raising funding, exceeding sales quotas, or launching a killer startup to impressive traction, intelligence (or IQ) doesn’t rank in the top 10. Heck, it may not even make the top 100. As a firsthand example, I’m not that smart — not by a long shot. That didn’t prevent me from bagging one of the coveted spots in the most prestigious banking group at age 22, saving 6-figures by 24, and launching multiple profitable startups that can make 6-figures in a few hours of work per month. That has nothing to do with smarts; that’s strategy, effort, preparation, and a sprinkle of luck, no doubt. Those results were also peppered with failures, losses, and setbacks along the way, but a higher IQ wouldn’t have solved those either.

Point being, your entrepreneurial, sales, and fundraising success can’t be blamed on your intelligence or lack thereof, and I can offer proof in the form of a cringeworthy business meeting wrecked by the smartest guy in the room. No, he didn’t get funding for his brilliant idea, even though he may have the technical chops to execute it. No, he didn’t make a sale, despite pitching it to prospective customers, investors, and advisors alike. And no, he doesn’t have a clue what he did wrong — and that just may be the most tragic part.

Here’s how not to pitch, market, or sell your startup, fundraising opportunity, or new product or service, no matter how much of a self-proclaimed genius you may be.

You know that feeling when you’re so embarrassed for somebody else that your own cheeks flash red and your skin starts crawling with invisible shame-inducing spiders? That second-hand embarrassment is exactly what happened to me and most everyone else on this call (I have the behind-the-scenes attendee feedback to confirm) as the spontaneous pitcher opened his mouth to hawk his ingenuity with ten pats on the back.

He could barely get a word out of his mouth without congratulating himself on being heads and shoulders smarter than everyone else in attendance. He referred to himself as a “genius” and a “whiz”, dismissing the rest of us (including prospective investors) as less knowledgeable mere mortals.

The problem with talking down to your audience is multi-fold, but here are a few obvious consequences:

  • Prospective customers simply don’t relate to or like you
  • Potential advisors and investors perceive you as rigid and un-teachable
  • Some of both (customers, advisors, and investors) will tune you out from the jump, dismissing your attitude as rude and your subject matter as inaccessible to the layperson. If you can’t explain a complex subject in basic terms, you’re more likely to repel than impress, believe it or not.

But don’t worry — it gets worse.

I’m not referring to the entrepreneur’s GPA or the school he graduated from; I’m talking about educating your audience. If you want to sell anything or attract a colleague, advisor, customer, or peer to your side, you’re going to need to get them interested in your product, service, or business. Unfortunately, few people are interested in things they don’t understand; that’s why it’s your job to educate them. And yes, it’s entirely possible to educate a non-expert audience without talking down to or belittling them.

Along those lines, before you educate, you should probably take a moment to qualify. This founder didn’t pose a single question to the audience; instead, he dove into his complex ramble, losing people’s interest in milliseconds.

Ask first. Then craft your answers to cater to the qualified audience. Educate before you sell or else your pitch may fall on deaf ears.

As the entrepreneur, you’re unequivocally the least important person to please with your product, service, business, or sales pitch — unless you’re your one and only customer, I suppose. However, if you’re trying to build a business that will rely on sales (and possibly investment) from others, you’ll need to prioritize those others far above yourself.

Thus, an arrogant, self-aggrandizing, narcissistic attitude is unlikely to help you out. This entrepreneur spent over thirty minutes of a two-hour group call basking in his own brilliance, lauding his impressive competencies, and forgetting that the brilliant product he’d created was only valuable if others deemed it so. You can be the greatest technical whiz out there, but if you’re only building products for yourself to revel in, you may find the revenue and social proof lacking.

In the pecking order of importance, customers and investors come first and entrepreneurs and team members fall far behind. Why? Because without those investors and customers, you’re simply dabbling away at your fun technical hobby, creating inventions for the spiders in your closet to applaud.

I’ll be honest: I’m not the biggest people-pleaser out there. It’s probably one of my downsides, and it’s definitely something I’m well aware of in social and business interactions. On the flip side, I know admitted underperformers who’ve worked their way into enviable career, entrepreneurial, equity-holding, and financial situations simply by relying on their social skills — and these aren’t salespeople, either. That said, those of us lacking the gift of effortless social brilliance should still realize that facts, figures, achievements, credentials, and competence can’t offset poor social skills.

This entrepreneur made one of the biggest foibles repeatedly throughout his pitch, which likely dashed any remaining attempt he had at fundraising: He failed to read between the lines of audience questions.

When an audience member asked a question that revealed their comparative lack of knowledge or confusion, he inconsiderately glossed over it, neglecting to answer it compassionately and alienating the entire group in the process. Perhaps he figured the inquirer wasn’t his target audience and would never be a customer or investor. While that may be true, every public display of communication is an opportunity to make or break your and your company’s reputation and culture. You can guess which option he chose.

Once you’ve inked a deal, accepted an investor, or taken a job, you pretty much know who’s the boss, and the power dynamic shouldn’t be a surprise. Sometimes, however, as you’re in the stages of marketing, fundraising, job-hunting, or pitching, you may not realize that very powerful incognito bosses may be lurking in the shadows. This entrepreneur had no clue who wielded the true power amongst his audience of listeners and moderators, and that may have been his downfall.

The ideal investor may not have been sitting in the virtual room that day, but as someone with access to the guest list, I can assure they were definitely no more than a few degrees of separation away. Sadly, as this founder dismissed the moderator as “the help”, treating them like an irrelevant, incompetent, powerless paper-pusher at best, he had no clue that he disrespected the one person who holds the keys to exactly what and who he needs.

After all was said and done, once he realized the error of his ways, he shamelessly demanded they open up their rolodex and serve him a warm referral to that investor on a silver platter. I believe they may have accepted his request to some small degree, but let’s just say a “warm” introduction (or any positive one at all) is an unlikely outcome.

As much as some people would like to believe confidence, competence, intelligence, credentials, accomplishments, or effort are the keys to entrepreneurial success in sales and fundraising, they aren’t. The missing link that betrays some of the most brilliant minds and accomplished, driven, competent founders is failing to realize that at the end of the day, it’s people who make most of the buying and investing decisions.

If you can’t figure out how to make them happy, make them like you (or your product), and make them want to support you or your venture, even the most novel invention can lay dormant in your dark, dingy basement, with no sales, no investors, and no one willing to clue you into why that is. Don’t just make something people want; make them want it from you.

Go to Publisher:

Entrepreneur's Handbook – Medium

Author: Rachel Greenberg